Dean's handbook of organic chemistry [2nd ed] 9781591248620, 1591248620

Table of contents :
Dean Handbook of Organic Chemistry 2nd edition 1......Page 1
Front Matter......Page 2
Preface......Page 3
Table of Contents......Page 0
Table of Contents......Page 4
1. Organic Compounds......Page 16
Table 1.1 Names of Straight-Chain Alkanes......Page 17
Table 1.2 Fused Polycyclic Hydrocarbons......Page 23
Table 1.4 Suffixes for Specialist Nomenclature of Heterocyclic Systems......Page 27
Table 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names......Page 28
Table 1.6 Trivial Names for Heterocyclic Systems That Are Not Recommended for Use in Fusion Names......Page 31
Functionalized Compounds......Page 33
Table 1.7 Characteristic Groups for Substitutive Nomenclature......Page 34
Table 1.8 Characteristic Groups Cited Only as Prefixes in Substitutive Nomenclature......Page 36
Table 1.9 Functional Class Names Used in Radicofunctional Nomenclature......Page 39
Specific Functionalized Groups......Page 40
Table 1.10 Retained Trivial Names of Alcohols and Phenols with Structures......Page 41
Table 1.11 Names of Some Carboxylic Acids......Page 48
Table 1.12 Parent Structures of Phosphorus-Containing Compounds......Page 55
Table 1.13......Page 59
Stereochemistry......Page 62
Chemical Abstracts Indexing System......Page 75
Table 1.14 Empirical Formula Index for Organic Compounds......Page 76
Table 1.15 Physical Constants of Organic Compounds......Page 96
2. Inorganic and Organometallic Compounds......Page 411
Table 2.1 Physical Constants of Inorganic Compounds......Page 412
3. Properties of Atoms, Radicals, and Bonds......Page 444
Table 3.1 Table of Nuclides......Page 445
Electronegativity......Page 452
Table 3.2B Electronegativities of the Groups......Page 453
Table 3.3 Electron Affinities of Elements, Radicals, and Molecules......Page 454
Bond Lengths and Strengths......Page 456
Table 3.4A Bond Lengths between Carbon and Other Elements......Page 457
Table 3.4B Bond Lengths between Elements Other Than Carbon......Page 460
Table 3.5 Bond Strengths......Page 462
Table 3.6 Bond Dipole Moments......Page 473
Table 3.7 Group Dipole Moments......Page 474
4. Physical Properties......Page 476
Table 4.1 Solubility of Gases in Water......Page 477
Table 4.2 Vapor Pressure of Mercury......Page 483
Table 4.3 Vapor Pressure of Water for Temperatures from -10 to 120°C......Page 485
Table 4.5A Boiling Points for Common Organic Solvents......Page 487
Table 4.5B Boiling Points for Common Organic Solvents......Page 490
Table 4.5C Boiling Point for Common Organic Solvents......Page 492
Table 4.6 Molecular Elevation of the Boiling Point......Page 498
Table 4.7 Binary Azeotropic (Constant-Boiling) Mixtures......Page 500
Table 4.8 Ternary Azeotropic Mixtures......Page 521
Tables 4.9A and B Molecular Lowering of the Melting or Freezing Point......Page 527
Viscosity, Dielectric Constant, Dipole Moment, Surface Tension, and Refractive Index......Page 530
Table 4.10 Viscosity, Dielectric Constant, Dipole Moment and Surface Tension of Selected Organic Substances......Page 532
Table 4.11 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances......Page 569
Table 4.12 Refractive Index, Viscosity, Dielectric Constant, and Surface Tension of Water at Various Temperatures......Page 573
Table 4.13 Properties of Combustible Mixtures in Air......Page 574
5. Thermodynamic Properties......Page 578
Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities......Page 579
Table 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds......Page 580
Table 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds......Page 621
Table 5.3 Critical Properties......Page 652
Table 5.4 Group Contributions for the Estimation of Critical Properties......Page 665
6. Spectroscopy......Page 667
Ultraviolet-Visible Spectroscopy......Page 669
Table 6.1 Electronic Absorption Bands for Representative Chromophores......Page 671
Table 6.2 Ultraviolet Cutoffs of Spectrograde Solvents......Page 672
Table 6.4 Absorption Wavelength of Enones and Dienones......Page 673
Table 6.5 Solvent Correction for UV-VIS Spectroscopy......Page 674
Table 6.7 Wavelength Calculation of the Principal Band of Substituted Benzene Derivatives......Page 675
Photoluminescence......Page 676
Table 6.8 Fluorescence Spectroscopy Data of Some Organic Compounds......Page 677
Table 6.10 Phosphorescence Spectroscopy of Some Organic Compounds......Page 683
Table 6.11 Absorption Frequencies of Single Bonds to Hydrogen......Page 687
Table 6.12 Absorption Frequencies of Triple Bonds......Page 694
Table 6.13 Absorption Frequencies of Cumulated Double Bonds......Page 695
Table 6.14 Absorption Frequencies of Carbonyl Bonds......Page 697
Table 6.15 Absorption Frequencies of Other Double Bonds......Page 701
Table 6.16 Absorption Frequencies of Aromatic Bonds......Page 705
Table 6.17 Absorption Frequencies of Miscellaneous Bands......Page 706
Table 6.18 Absorption Frequencies in the Near Infrared......Page 713
Table 6.19 Infrared Transmitting Materials......Page 715
Table 6.20 Infrared Transmission Characteristics of Selected Solvents......Page 717
Table 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon......Page 720
Table 6.22 Raman Frequencies of Triple Bonds......Page 725
Table 6.23 Raman Frequencies of Cumulated Double Bonds......Page 726
Table 6.24 Raman Frequencies of Carbonyl Bonds......Page 727
Table 6.25 Raman Frequencies of Other Double Bonds......Page 729
Table 6.26 Raman Frequencies of Aromatic Compounds......Page 732
Table 6.27 Raman Frequencies of Sulfur Compounds......Page 733
Table 6.28 Raman Frequencies of Ethers......Page 735
Table 6.29 Raman Frequencies of Halogen Compounds......Page 736
Nuclear Magnetic Resonance Spectroscopy......Page 737
Table 6.31 Nuclear Properties of the Elements......Page 739
Table 6.32 Proton Chemical Shifts of Reference Compounds Relative to Tetramethylsilane......Page 740
Table 6.33 Common NMR Solvents......Page 741
Table 6.34 Proton Chemical Shifts......Page 742
Table 6.35 Estimation of Chemical Shift for Proton of -CH2- and >CH- Groups......Page 745
Table 6.36 Estimation of Chemical Shift of Proton Attached to a Double Bond......Page 746
Table 6.37 Chemical Shifts in Monosubstituted Benzene......Page 747
Table 6.38 Proton Spin Coupling Constants......Page 748
Table 6.39 Carbon-13 Chemical Shifts......Page 749
Table 6.40 Estimation of Chemical Shifts of Alkane Carbons......Page 752
Table 6.41 Effect of Substituent Groups on Alkyl Chemical Shifts......Page 753
Table 6.42 Estimation of Chemical Shift of Carbon Attached to a Double Bond......Page 754
Table 6.43 Carbon-13 Chemical Shifts in Substituted Benzenes......Page 755
Table 6.44 Carbon-13 Chemical Shifts in Substituted Pyridines......Page 756
Table 6.45 Carbon-13 Chemical Shifts of Carbonyl Group......Page 757
Table 6.46 One-Bond Carbon-Hydrogen Spin Coupling Constants......Page 758
Table 6.48 Carbon-Carbon Spin Coupling Constants......Page 759
Table 6.49 Carbon-Fluorine Spin Coupling Constants......Page 760
Table 6.50 Carbon-13 Chemical Shifts of Deuterated Solvents......Page 761
Table 6.52 Boron-11 Chemical Shifts......Page 762
Table 6.53 Nitrogen-15 (or Nitrogen-14) Chemical Shifts......Page 763
Table 6.54 Nitrogen-15 Chemical Shifts in Monosubstituted Pyridine......Page 766
Table 6.56 Nitrogen-15 to Hydrogen-1 Spin Coupling Constants......Page 767
Table 6.59 Fluorine-19 Chemical Shifts......Page 768
Table 6.62 Silicon-29 Chemical Shifts......Page 770
Table 6.63 Phosphorus-31 Chemical Shifts......Page 771
Table 6.64 Phosphorus-31 Spin Coupling Constants......Page 775
Electron Spin Resonance......Page 776
Table 6.65 Spin-Spin Coupling (Hyperfine Splitting Constants)......Page 777
Table 6.66A Ionization Potentials of Molecular Species......Page 780
Table 6.66B Alphabetical Listing of Ionization Potentials of Molecular Species......Page 786
X-Ray Diffraction......Page 788
7. Physiochemical Relationships......Page 791
Linear Free Energy Relationships......Page 792
Table 7.1 Hammett and Taft Substituent Constants......Page 793
Table 7.2 pKA and Rho (p) Values for the Hammett Equation......Page 798
Table 7.4 Special Hammett Sigma Constants......Page 800
8. Electrolytes, Electromotive Force, and Chemical Equilibrium......Page 802
Equilibrium Constants......Page 803
Table 8.1 pKA Values of Organic Materials in Water at 25°C......Page 804
Table 8.2 Proton-Transfer Reactions of Inorganic Materials in Water at 25°C......Page 862
Table 8.3 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures......Page 865
Table 8.4 Indicators for Aqueous Acid-Base Titrations......Page 873
Table 8.5 National Institute of Standards and Technology (Formerly National Bureau of (Standards U.S.)) Reference pH Buffer Solutions......Page 875
Table 8.6 Compositions of National Institute of Standards and Technology. Standard pH Buffer Solutions......Page 876
Table 8.7 pH Values of Buffer Solutions for Control Purposes......Page 877
Table 8.8 Potentials of Reference Electrodes (in Volts) as a Function of Temperature......Page 878
Table 8.9 Potentials of Reference Electrodes (in Volts) at 25°C for Water-Organic Solvent Mixtures......Page 880
Table 8.10 Potentials of Selected Half-Reactions at 25°C......Page 881
Table 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25°C......Page 883
9. Data Useful in Laboratory Manipulations and Analysis......Page 895
Humidification and Drying......Page 896
Table 9.4 Humidity (%) Maintained by Saturated Solutions of Common Salts at Specified Temperatures......Page 897
Table 9.5 Drying Agents......Page 898
Table 9.6 Solvents of Chromatographic Interest......Page 899
Table 9.7 Solvents Having the Same Refractive Index and the Same Density at 25°C......Page 901
Table 9.8 McReynolds' Constants for Stationary Phases in Gas Chromatography......Page 904
10. Polymers, Rubbers, Fats, Oils, and Waxes......Page 908
Polymers......Page 909
Table 10.1 Plastic Families......Page 914
Formulas and Key Properties of Plastic Materials......Page 916
Table 10.2 Properties of Commercial Plastics......Page 931
Formulas and Advantages of Rubbers......Page 967
Table 10.3 Properties of Natural and Synthetic Rubbers......Page 971
Table 10.4 Resistance of Selected Polymers and Rubbers to Various Chemicals at 20°C......Page 972
Table 10.5 Common Abbreviations Used in Polymer Chemistry......Page 974
Table 10.6 Gas Permeability Constants (1010P) at 25°C for Polymers and Rubbers......Page 977
Table 10.8 Constants of Fats and Oils......Page 980
Table 10.9 Constants of Waxes......Page 983
11. Abbreviations, Constants, and Conversion Factors......Page 985
Table 11.1 Fundamental Physical Constants......Page 986
Table 11.4 Numerical Prefixes......Page 989
Table 11.5 Conversion Formulas for Solutions Having Concentrations Expressed in Various Ways......Page 990
Table 11.6 Conversion Factors......Page 991
Table 11.7 Values of t......Page 998
A......Page 1000
B......Page 1004
C......Page 1007
D......Page 1012
E......Page 1013
F......Page 1016
H......Page 1018
I......Page 1021
K......Page 1023
M......Page 1024
N......Page 1026
P......Page 1028
R......Page 1033
S......Page 1035
T......Page 1039
U......Page 1040
V......Page 1041
Z......Page 1042

Citation preview

DEAN’S HANDBOOK OF ORGANIC CHEMISTRY George W. Gokel, Ph.D. Director, Program in Chemical Biology Professor, Department of Molecular Biology and Pharmacology Washington University School of Medicine Professor, Department of Chemistry Washington University St. Louis Missouri

Second Edition

MCGRAW-HILL New York Chicago San Francisco Lisbon London Madrid Mexico City Milan New Delhi San Juan Seoul Singapore Sydney Toronto

PREFACE

The first edition of the Handbook of Organic Chemistry was edited by Professor John A. Dean. It appeared in 1987 and has served as a widely used and convenient reference work for more than 15 years. When Professor Dean asked if I would work with him to develop a second edition, I was pleased to do so. I felt that as valuable as the first edition was, it would be more broadly useful if it contained discussions of the data, the means by which the data were acquired, and perhaps even how the data are applied in modern science. We thus began the revision with enhanced usability as the foremost goal. Sadly, just as we were beginning the effort, Professor Dean passed away. He will be sorely missed. In following the original plan, many figures, structures, discussions of the methods, and illustrations of the data have been incorporated. Some tables have been reorganized. In some cases tables have been printed twice; although they contain the same data, they are arranged by different criteria. The intent is to make the data easier for the researcher to access and use. Some Internet addresses that can serve as a supplementary resource are included. Despite the numerous additions, the volume remains compact and accessible. As Professor Dean was not involved in producing this edition, I take responsibility for errors of fact or omission. I hope the volume is error-free, but I would appreciate being informed of any mistakes that are found. Finally, I wish to express my thanks to Mrs. Jolanta Pajewska, who helped in improving the manuscript and the proofreading. GEORGE W. GOKEL

iv

Contents

Preface .............................................................................

iv

About the Author ...............................................................

v

1.

Organic Compounds ...............................................

1.1

Nomenclature of Organic Compounds .................................

1.2

Hydrocarbons and Heterocycles .................................. Table 1.1 Names of Straight-Chain Alkanes ............. Table 1.2 Fused Polycyclic Hydrocarbons ................. Table 1.3 Specialist Nomenclature for Heterocyclic Systems ......................................... Table 1.4 Suffixes for Specialist Nomenclature of Heterocyclic Systems ..................................... Table 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names ................................................................ Table 1.6 Trivial Names for Heterocyclic Systems That Are Not Recommended for Use in Fusion Names .........................................

1.2 1.2 1.8

Functionalized Compounds ......................................... Table 1.7 Characteristic Groups for Substitutive Nomenclature ..................................................... Table 1.8 Characteristic Groups Cited Only as Prefixes in Substitutive Nomenclature ................ Table 1.9 Functional Class Names Used in Radicofunctional Nomenclature .........................

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1.12 1.12

1.13

1.16 1.18 1.19 1.21 1.24

iii

iv

Contents Specific Functionalized Groups ................................... Table 1.10 Retained Trivial Names of Alcohols and Phenols with Structures ............................... Table 1.11 Names of Some Carboxylic Acids ........... Table 1.12 Parent Structures of PhosphorusContaining Compounds ...................................... Table 1.13 ..................................................................

1.25 1.26 1.33 1.40 1.44

Stereochemistry .......................................................... 1.47 Chemical Abstracts Indexing System .......................... 1.60 Physical Properties of Pure Substances ...............................

1.61

Table 1.14 Empirical Formula Index for Organic Compounds ........................................................... 1.61 Table 1.15 Physical Constants of Organic Compounds ........................................................... 1.80

2.

3.

Inorganic and Organometallic Compounds ..........

2.1

Table 2.1 Physical Constants of Inorganic Compounds .....................................................................

2.2

Properties of Atoms, Radicals, and Bonds ...........

3.1

Nuclides .................................................................................

3.2

Table 3.1 Table of Nuclides .........................................

3.2

Electronegativity ....................................................................

3.9

Table 3.2A Electronegativities of the Elements ........... 3.10 Table 3.2B Electronegativities of the Groups ............... 3.10 Electron Affinity ......................................................................

3.11

Table 3.3 Electron Affinities of Elements, Radicals, and Molecules ........................................ 3.11 Bond Lengths and Strengths ................................................

3.13

Table 3.4A Bond Lengths between Carbon and Other Elements ...................................................... 3.14

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Contents

v

Table 3.4B Bond Lengths between Elements Other Than Carbon ................................................ 3.17 Table 3.5 Bond Strengths ............................................ 3.19 Bond and Group Dipole Moments ........................................

3.30

Table 3.6 Bond Dipole Moments ................................. 3.30 Table 3.7 Group Dipole Moments ................................ 3.31

4.

Physical Properties .................................................

4.1

Solubilities .............................................................................

4.2

Table 4.1 Solubility of Gases in Water .........................

4.2

Vapor Pressures ....................................................................

4.8

Table 4.2 Vapor Pressure of Mercury ..........................

4.8

Table 4.3 Vapor Pressure of Water for Temperatures from –10 to 120°C .......................... 4.10 Table 4.4 Vapor Pressure of Deuterium Oxide ............ 4.12 Boiling Points .........................................................................

4.12

Table 4.5A Boiling Points for Common Organic Solvents ................................................................ 4.12 Table 4.5B Boiling Points for Common Organic Solvents ................................................................ 4.15 Table 4.5C Boiling Point for Common Organic Solvents ................................................................ 4.17 Table 4.6 Molecular Elevation of the Boiling Point ...................................................................... 4.23 Table 4.7 Binary Azeotropic (Constant-Boiling) Mixtures ................................................................. 4.25 Table 4.8 Ternary Azeotropic Mixtures ........................ 4.46 Freezing Points .....................................................................

4.52

Tables 4.9A and B Molecular Lowering of the Melting or Freezing Point ....................................... 4.52 Viscosity, Dielectric Constant, Dipole Moment, Surface Tension, and Refractive Index ........................................ This page has been reformatted by Knovel to provide easier navigation.

4.55

vi

Contents Table 4.10 Viscosity, Dielectric Constant, Dipole Moment and Surface Tension of Selected Organic Substances .............................................. 4.57 Table 4.11 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances ............................................ 4.94 Table 4.12 Refractive Index, Viscosity, Dielectric Constant, and Surface Tension of Water at Various Temperatures ........................................... 4.98 Combustible Mixtures ............................................................

4.99

Table 4.13 Properties of Combustible Mixtures in Air ...................................................................... 4.99

5.

Thermodynamic Properties ....................................

5.1

Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities ......................................

5.2

Table 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds ..........................................

5.3

Table 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds ................... 5.44 Critical Phenomena ...............................................................

5.75

Table 5.3 Critical Properties ........................................ 5.75 Table 5.4 Group Contributions for the Estimation of Critical Properties .............................................. 5.88

6.

Spectroscopy ...........................................................

6.1

Ultraviolet-Visible Spectroscopy ...........................................

6.3

Table 6.1 Electronic Absorption Bands for Representative Chromophores ..............................

6.5

Table 6.2 Ultraviolet Cutoffs of Spectrograde Solvents ................................................................

6.6

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vii

Table 6.3 Absorption Wavelength of Dienes ................

6.7

Table 6.4 Absorption Wavelength of Enones and Dienones ...............................................................

6.7

Table 6.5 Solvent Correction for UV–VIS Spectroscopy .........................................................

6.8

Table 6.6 Primary Band of Substituted Benzene and Heteroaromatics .............................................

6.9

Table 6.7 Wavelength Calculation of the Principal Band of Substituted Benzene Derivatives ..............

6.9

Photoluminescence ...............................................................

6.10

Table 6.8 Fluorescence Spectroscopy Data of Some Organic Compounds .................................... 6.11 Table 6.9 Fluorescence Quantum Yield Values ........... 6.17 Table 6.10 Phosphorescence Spectroscopy of Some Organic Compounds .................................... 6.17 Infrared Spectroscopy ...........................................................

6.21

Table 6.11 Absorption Frequencies of Single Bonds to Hydrogen ................................................ 6.21 Table 6.12 Absorption Frequencies of Triple Bonds .................................................................... 6.28 Table 6.13 Absorption Frequencies of Cumulated Double Bonds ........................................................ 6.29 Table 6.14 Absorption Frequencies of Carbonyl Bonds .................................................................... 6.31 Table 6.15 Absorption Frequencies of Other Double Bonds ........................................................ 6.35 Table 6.16 Absorption Frequencies of Aromatic Bonds .................................................................... 6.39 Table 6.17 Absorption Frequencies of Miscellaneous Bands ............................................. 6.40 Table 6.18 Absorption Frequencies in the Near Infrared .................................................................. 6.47

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viii

Contents Table 6.19 Infrared Transmitting Materials .................. 6.49 Table 6.20 Infrared Transmission Characteristics of Selected Solvents .............................................. 6.51 Raman Spectroscopy ............................................................

6.54

Table 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon ....................................... 6.54 Table 6.22 Raman Frequencies of Triple Bonds .......... 6.59 Table 6.23 Raman Frequencies of Cumulated Double Bonds ........................................................ 6.60 Table 6.24 Raman Frequencies of Carbonyl Bonds .................................................................... 6.61 Table 6.25 Raman Frequencies of Other Double Bonds .................................................................... 6.63 Table 6.26 Raman Frequencies of Aromatic Compounds ........................................................... 6.66 Table 6.27 Raman Frequencies of Sulfur Compounds ........................................................... 6.67 Table 6.28 Raman Frequencies of Ethers ................... 6.69 Table 6.29 Raman Frequencies of Halogen Compounds ........................................................... 6.70 Table 6.30 Raman Frequencies of Miscellaneous Compounds ........................................................... 6.71 Nuclear Magnetic Resonance Spectroscopy .......................

6.71

Table 6.31 Nuclear Properties of the Elements ........... 6.73 Table 6.32 Proton Chemical Shifts of Reference Compounds Relative to Tetramethylsilane ............. 6.74 Table 6.33 Common NMR Solvents ............................ 6.75 Table 6.34 Proton Chemical Shifts .............................. 6.76 Table 6.35 Estimation of Chemical Shift for Proton of —CH2— and >CH— Groups .................. 6.79 Table 6.36 Estimation of Chemical Shift of Proton Attached to a Double Bond .................................... 6.80

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Contents

ix

Table 6.37 Chemical Shifts in Monosubstituted Benzene ................................................................ 6.81 Table 6.38 Proton Spin Coupling Constants ................ 6.82 Table 6.39 Carbon-13 Chemical Shifts ........................ 6.83 Table 6.40 Estimation of Chemical Shifts of Alkane Carbons ..................................................... 6.86 Table 6.41 Effect of Substituent Groups on Alkyl Chemical Shifts ...................................................... 6.87 Table 6.42 Estimation of Chemical Shift of Carbon Attached to a Double Bond ....................... 6.88 Table 6.43 Carbon-13 Chemical Shifts in Substituted Benzenes ............................................ 6.89 Table 6.44 Carbon-13 Chemical Shifts in Substituted Pyridines ............................................. 6.90 Table 6.45 Carbon-13 Chemical Shifts of Carbonyl Group ..................................................... 6.91 Table 6.46 One-Bond Carbon–Hydrogen Spin Coupling Constants ............................................... 6.92 Table 6.47 Two-Bond Carbon–Hydrogen Spin Coupling Constants ............................................... 6.93 Table 6.48 Carbon–Carbon Spin Coupling Constants .............................................................. 6.93 Table 6.49 Carbon–Fluorine Spin Coupling Constants .............................................................. 6.94 Table 6.50 Carbon-13 Chemical Shifts of Deuterated Solvents .............................................. 6.95 Table 6.51 Carbon-13 Spin Coupling Constants with Various Nuclei ................................................ 6.96 Table 6.52 Boron-11 Chemical Shifts .......................... 6.96 Table 6.53 Nitrogen-15 (or Nitrogen-14) Chemical Shifts ..................................................................... 6.97

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x

Contents Table 6.54 Nitrogen-15 Chemical Shifts in Monosubstituted Pyridine ...................................... 6.100 Table 6.55 Nitrogen-15 Chemical Shifts for Standards .............................................................. 6.101 Table 6.56 Nitrogen-15 to Hydrogen-1 Spin Coupling Constants ............................................... 6.101 Table 6.57 Nitrogen-15 to Carbon-13 Spin Coupling Constants ............................................... 6.102 Table 6.58 Nitrogen-15 to Fluorine-19 Spin Coupling Constants ............................................... 6.102 Table 6.59 Fluorine-19 Chemical Shifts ....................... 6.102 Table 6.60 Fluorine-19 Chemical Shifts for Standards .............................................................. 6.104 Table 6.61 Fluorine-19 to Fluorine-19 Spin Coupling Constants ............................................... 6.104 Table 6.62 Silicon-29 Chemical Shifts ......................... 6.104 Table 6.63 Phosphorus-31 Chemical Shifts ..................................................................... 6.105 Table 6.64 Phosphorus-31 Spin Coupling Constants .............................................................. 6.109 Electron Spin Resonance ...................................................... 6.110 Table 6.65 Spin–Spin Coupling (Hyperfine Splitting Constants) ............................................... 6.111 Ionization Potentials .............................................................. 6.114 Table 6.66A Ionization Potentials of Molecular Species ................................................................. 6.114 Table 6.66B Alphabetical Listing of Ionization Potentials of Molecular Species ............................. 6.120 Table 6.67 Ionization Potentials of Radical Species ................................................................. 6.122 X-Ray Diffraction ................................................................... 6.122

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Contents 7.

xi

Physiochemical Relationships ...............................

7.1

Linear Free Energy Relationships .........................................

7.2

Table 7.1 Hammett and Taft Substituent Constants ..............................................................

7.3

Table 7.2 pKA and Rho (p) Values for the Hammett Equation .................................................

7.8

Table 7.3 pKA and Rho (p) Values for the Taft Equation ................................................................ 7.10 Table 7.4 Special Hammett Sigma Constants .............................................................. 7.10

8.

Electrolytes, Electromotive Force, and Chemical Equilibrium ..............................................

8.1

Equilibrium Constants ...........................................................

8.2

Table 8.1 pKA Values of Organic Materials in Water at 25°C ........................................................

8.3

Table 8.2 Proton-Transfer Reactions of Inorganic Materials in Water at 25°C ..................................... 8.61 Table 8.3 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures ........... 8.64 Table 8.4 Indicators for Aqueous Acid–Base Titrations ............................................................... 8.72 Buffer Solutions .....................................................................

8.74

Table 8.5 National Institute of Standards and Technology (Formerly National Bureau of (Standards U.S.)) Reference pH Buffer Solutions ................................................................ 8.74 Table 8.6 Compositions of National Institute of Standards and Technology. Standard pH Buffer Solutions ..................................................... 8.75 Table 8.7 pH Values of Buffer Solutions for Control Purposes ................................................... 8.76

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xii

Contents Reference Electrodes ............................................................

8.77

Table 8.8 Potentials of Reference Electrodes (in Volts) as a Function of Temperature ...................... 8.77 Table 8.9 Potentials of Reference Electrodes (in Volts) at 25°C for Water–Organic Solvent Mixtures ................................................................. 8.79 Electrode Potentials ..............................................................

8.80

Table 8.10 Potentials of Selected Half-Reactions at 25°C .................................................................. 8.80 Table 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25°C .................................................................. 8.82

9.

Data Useful in Laboratory Manipulations and Analysis ....................................................................

9.1

Cooling Mixtures ....................................................................

9.2

Table 9.1 Cooling Mixtures Made from Dry Ice and Salts ...............................................................

9.2

Table 9.2 Dry Ice or Liquid Nitrogen Slush Baths ........

9.2

Humidification and Drying .....................................................

9.2

Table 9.3 Humidity (%) Maintained by Saturated Solutions of Various Salts at Specified Temperatures ........................................................

9.3

Table 9.4 Humidity (%) Maintained by Saturated Solutions of Common Salts at Specified Temperatures ........................................................

9.3

Table 9.5 Drying Agents ..............................................

9.4

Separation Methods ..............................................................

9.5

Table 9.6 Solvents of Chromatographic Interest ..........

9.5

Table 9.7 Solvents Having the Same Refractive Index and the Same Density at 25°C .....................

9.7

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Contents

xiii

Table 9.8 McReynolds’ Constants for Stationary Phases in Gas Chromatography ............................ 9.10

10. Polymers, Rubbers, Fats, Oils, and Waxes ........... 10.1 Polymers ................................................................................

10.2

Table 10.1 Plastic Families ......................................... 10.7 Formulas and Key Properties of Plastic Materials ................

10.9

Table 10.2 Properties of Commercial Plastics ............. 10.24 Formulas and Advantages of Rubbers ................................. 10.60 Table 10.3 Properties of Natural and Synthetic Rubbers ................................................................. 10.64 Chemical Resistance ............................................................ 10.65 Table 10.4 Resistance of Selected Polymers and Rubbers to Various Chemicals at 20°C .................. 10.65 Table 10.5 Common Abbreviations Used in Polymer Chemistry ................................................ 10.67 Gas Permeability ................................................................... 10.70 Table 10.6 Gas Permeability Constants (1010P) at 25°C for Polymers and Rubbers ............................ 10.70 Table 10.7 Vapor Permeability Constants (1010P) at 35°C for Polymers ............................................. 10.73 Fats, Oils, and Waxes ........................................................... 10.73 Table 10.8 Constants of Fats and Oils ........................ 10.73 Table 10.9 Constants of Waxes .................................. 10.76

11. Abbreviations, Constants, and Conversion Factors ...................................................................... 11.1 Physical Constants ................................................................

11.2

Table 11.1 Fundamental Physical Constants ............... 11.2 Greek Alphabet .....................................................................

11.5

Table 11.2 Greek Alphabet .......................................... 11.5

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xiv

Contents Prefixes ..................................................................................

11.5

Table 11.3 Prefixes for Naming Multiples and Submultiples of Units ............................................. 11.5 Table 11.4 Numerical Prefixes .................................... 11.5 Transformations ....................................................................

11.6

Table 11.5 Conversion Formulas for Solutions Having Concentrations Expressed in Various Ways ..................................................................... 11.6 Table 11.6 Conversion Factors ................................... 11.7 Statistics ................................................................................ 11.14 Table 11.7 Values of t ................................................. 11.14

Index ................................................................................

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I.1

SECTION 1

ORGANIC COMPOUNDS

NOMENCLATURE OF ORGANIC COMPOUNDS . . . . . . . . Hydrocarbons and Heterocycles . . . . . . . . . . . . . . . . . Table 1.1 Names of Straight-Chain Alkanes . . . . . . . . Table 1.2 Fused Polycyclic Hydrocarbons . . . . . . . . . Table 1.3 Specialist Nomenclature for Heterocyclic Systems . . . . . . . . . . . . . . . . . . . . . . Table 1.4 Suffixes for Specialist Nomenclature of Heterocyclic Systems . . . . . . . . . . . . . . . Table 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names . . . . . . . . . . . . . Table 1.6 Trivial Names for Heterocyclic Systems that are Not Recommended for Use in Fusion Names . . Functionalized Compounds . . . . . . . . . . . . . . . . . . . Table 1.7 Characteristic Groups for Substitutive Nomenclature . . . . . . . . . . . . . . . . . . . Table 1.8 Characteristic Groups Cited Only as Prefixes in Substitutive Nomenclature . . . . . . . . . . . Table 1.9 Functional Class Names Used in Radicofunctional Nomenclature . . . . . . . . . . . . . . . . . . . Specific Functionalized Groups . . . . . . . . . . . . . . . . . Table 1.10 Retained Trivial Names of Alcohols and Phenols with Structures . . . . . . . . . . . . . . . . . . Table 1.11 Names of Some Carboxylic Acids . . . . . . . . Table 1.12 Parent Structures of Phosphorus-containing Compounds . . . . . . . . . . . . . . . . . . . . Table 1.13 . . . . . . . . . . . . . . . . . . . . . . . . . . . Stereochemistry . . . . . . . . . . . . . . . . . . . . . . . . . . Chemical Abstracts Indexing System . . . . . . . . . . . . . . PHYSICAL PROPERTIES OF PURE SUBSTANCES . . . . . . . Table 1.14 Empirical Formula Index for Organic Compounds . . . . . . . . . . . . . . . . . . . . Table 1.15 Physical Constants of Organic Compounds . . .

1.1

. . . .

. . . .

. . . .

1.2 1.2 1.2 1.8

. . .

1.12

. . .

1.12

. . .

1.13

. . . . . .

1.16 1.18

. . .

1.19

. . .

1.21

. . . . . .

1.24 1.25

. . . . . .

1.26 1.34

. . . . .

. . . . .

1.40 1.44 1.47 1.60 1.61

. . . . . .

1.61 1.80

. . . . .

1.2

SECTION 1

NOMENCLATURE OF ORGANIC COMPOUNDS The following synopsis of rules for naming organic compounds and the examples given in explanation are not intended to cover all the possible cases. For a more comprehensive and detailed description, see J. Rigaudy and S. P. Klesney, Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford, 1979. This publication contains the recommendations of the Commission on Nomenclature of Organic Chemistry and was prepared under the auspices of the International Union of Pure and Applied Chemistry (IUPAC). Hydrocarbons and Heterocycles Alkanes. The saturated open-chain (acyclic) hydrocarbons (CnH2n  2) have names ending in -ane. The first four members have the trivial names methane (CH4), ethane (CH3CH3 or C2H6), propane (C3H8), and butane (C4H10). For the remainder of the alkanes, the first portion of the name is derived from the Greek prefix (see Table 11.4) that cites the number of carbons in the alkane followed by -ane with elision of the terminal -a from the prefix, as shown in Table 1.1. TABLE 1.1 Names of Straight-Chain Alkanes n*

Name

n*

Name

n*

Name

1 2 3 4 5 6 7 8 9 10

Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane† Decane

11 12 13 14 15 16 17 18 19 20

Undecane‡ Dodecane Tridecane Tetradecane Pentadecane Hexadecane Heptadecane Octadecane Nonadecane Icosane§

21 22 23

Henicosane Docosane Tricosane

30 31 32

Triacontane Hentriacontane Dotriacontane

40 50

Tetracontane Pentacontane

n* 60 70 80 90 100 110 120 121

Name Hexacontane Heptacontane Octacontane Nonacontane Hectane Decahectane Icosahectane Henicosahectane

*n  total number of carbon atoms. † Formerly called enneane. ‡ Formerly called hendecane. § Formerly called eicosane.

For branching compounds, the parent structure is the longest continuous chain present in the compound. Consider the compound to have been derived from this structure by replacement of hydrogen by various alkyl groups. Arabic number prefixes indicate the carbon to which the alkyl group is attached. Start numbering at whichever end of the parent structure that results in the lowest-numbered locants. The arabic prefixes are listed in numerical sequence, separated from each other by commas and from the remainder of the name by a hyphen. If the same alkyl group occurs more than once as a side chain, this is indicated by the prefixes di-, tri-, tetra-, etc. Side chains are cited in alphabetical order (before insertion of any multiplying prefix). The name of a complex radical (side chain) is considered to begin with the first letter of its complete name. Where names of complex radicals are composed of identical words, priority for citation is given to that radical which contains the lowestnumbered locant at the first cited point of difference in the radical. If two or more side chains are in equivalent positions, the one to be assigned the lowest-numbered locant is that cited first in the name. The complete expression for the side chain may be enclosed in parentheses for clarity or the carbon atoms in side chains may be indicated by primed locants.

ORGANIC COMPOUNDS

1.3

H H H H H H H H H H H C C C C C C C C C C H H H H H H H H H H H H3C

CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3

FIGURE 1.1

Projections for n-decane

If hydrocarbon chains of equal length are competing for selection as the parent, the choice goes in descending order to (1) the chain that has the greatest number of side chains, (2) the chain whose side chains have the lowest-numbered locants, (3) the chain having the greatest number of carbon atoms in the smaller side chains, or (4) the chain having the leastbranched side chains. These trivial names may be used for the unsubstituted hydrocarbons only: Isobutane (CH3)2CHCH3 Isopentane (CH3)2CHCH2CH3

Neopentane (CH3)4C Isohexane (CH3)2CHCH2CH2CH3

Univalent radicals derived from saturated unbranched alkanes by removal of hydrogen from a terminal carbon atom are named by adding -yl in place of -ane to the stem name. Thus the alkane ethane becomes the radical ethyl. These exceptions are permitted for unsubstituted radicals only: Isopropyl (CH3)2CH— Isobutyl (CH3)2CHCH2 ˆ sec-Butyl CH3CH2CH(CH3) ˆ tert-Butyl (CH3)3C ˆ

Isopentyl (CH3)2CHCH2CH2ˆ Neopentyl (CH3)3CCH2 ˆ tert-Pentyl CH3CH2C(CH3)2 ˆ Isohexyl (CH3)2CHCH2CH2CH2 ˆ

Note the usage of the prefixes iso-, neo-, sec-, and tert-, and note when italics are employed. Italicized prefixes are never involved in alphabetization, except among themselves; thus sec-butyl would precede isobutyl, isohexyl would precede isopropyl, and sec-butyl would precede tert-butyl. Examples of alkane nomenclature are

1.4

SECTION 1

Bivalent radicals derived from saturated unbranched alkanes by removal of two hydrogen atoms are named as follows: (1) If both free bonds are on the same carbon atom, the ending -ane of the hydrocarbon is replaced with -ylidene. However, for the first member of the alkanes it is methylene rather than methylidene. Isopropylidene, sec-butylidene, and neopentylidene may be used for the unsubstituted group only. (2) If the two free bonds are on different carbon atoms, the straight-chain group terminating in these two carbon atoms is named by citing the number of methylene groups comprising the chain. Other carbons groups are named as substituents. Ethylene is used rather than dimethylene for the first member of the series, and propylene is retained for CH3 ˆ CH ˆ CH2 ˆ (but trimethylene is ˆ CH2 ˆ | CH2 ˆ CH2 ˆ ). Trivalent groups derived by the removal of three hydrogen atoms from the same carbon are named by replacing the ending -ane of the parent hydrocarbon with -ylidyne. Alkenes and Alkynes. Each name of the corresponding saturated hydrocarbon is converted to the corresponding alkene by changing the ending -ane to -ene. For alkynes the ending is -yne. With more than one double (or triple) bond, the endings are -adiene, -atriene, etc. (or -adiyne, -atriyne, etc.). The position of the double (or triple) bond in the parent chain is indicated by a locant obtained by numbering from the end of the chain nearest the double (or triple) bond; thus CH3CH2CH ¨ CH2 is 1-butene and CH3C ˜ CCH3 is 2-butyne. For multiple unsaturated bonds, the chain is so numbered as to give the lowest possible locants to the unsaturated bonds. When there is a choice in numbering, the double

ORGANIC COMPOUNDS

1.5

bonds are given the lowest locants, and the alkene is cited before the alkyne where both occur in the name. Examples: 1,3-Octadiene CH3CH2CH2CH2CH ¨ CH ˆ CH ¨ CH2 CH2 ¨ CHC ˜ CCH ¨ CH2 1,5-Hexadiene-3-yne CH3CH ¨ CHCH2C ˜ CH 4-Hexen-1-yne CH ˜ CCH2CH ¨ CH2 1-Penten-4-yne Unsaturated branched acyclic hydrocarbons are named as derivatives of the chain that contains the maximum number of double and/or triple bonds. When a choice exists, priority goes in sequence to (1) the chain with the greatest number of carbon atoms and (2) the chain containing the maximum number of double bonds. These nonsystematic names are retained: Ethylene CH2 ¨ CH2 Allene CH2 ¨ C ¨ CH2 Acetylene HC ˜ CH An example of nomenclature for alkenes and alkynes is

Univalent radicals have the endings -enyl, -ynyl, -dienyl, -diynyl, etc. When necessary, the positions of the double and triple bonds are indicated by locants, with the carbon atom with the free valence numbered as 1. Examples: 2-Propenyl CH2 ¨ CH ˆ CH2 ˆ CH3 ˆ C ˜ C ˆ 1-Propynyl CH3 ˆ C ˜ C ˆ CH2CH ¨ CH2 ˆ 1-Hexen-4-ynyl These names are retained: Vinyl (for ethenyl) CH2 ¨ CH ˆ Allyl (for 2-propenyl) CH2 ¨ CH ˆ CH2 ˆ Isopropenyl (for 1-methylvinyl but for unsubstituted radical only)

CH2 ¨ C(CH3) ˆ

Should there be a choice for the fundamental straight chain of a radical, that chain is selected which contains (1) the maximum number of double and triple bonds, (2) the largest number of carbon atoms, and (3) the largest number of double bonds. These are in descending priority. Bivalent radicals derived from unbranched alkenes, alkadienes, and alkynes by removing a hydrogen atom from each of the terminal carbon atoms are named by replacing the endings -ene, -diene, and -yne by -enylene, -dienylene, and -ynylene, respectively. Positions of double and triple bonds are indicated by numbers when necessary. The name vinylene instead of ethenylene is retained for ˆ CH ¨ CH ˆ . Monocyclic Aliphatic Hydrocarbons. Monocyclic aliphatic hydrocarbons (with no side chains) are named by prefixing cyclo- to the name of the corresponding open-chain hydrocarbon having the same number of carbon atoms as the ring. Radicals are formed as with the alkanes, alkenes, and alkynes. Examples:

1.6

SECTION 1

Cyclohexyl- (for the radical) 1-Cyclohexenyl- (for the radical with the free valence at carbon 1) Cyclohexadienyl- (the unsaturated carbons are given numbers as low as possible, numbering from the carbon atom with the free valence given the number 1) For convenience, aliphatic rings are often represented by simple geometric figures: a triangle for cyclopropane, a square for cyclobutane, a pentagon for cyclopentane, a hexagon (as illustrated) for cyclohexane, etc. It is understood that two hydrogen atoms are located at each corner of the figure unless some other group is indicated for one or both. Monocyclic Aromatic Compounds. Except for six retained names, all monocyclic substituted aromatic hydrocarbons are named systematically as derivatives of benzene. Moreover, if the substituent introduced into a compound with a retained trivial name is identical with one already present in that compound, the compound is named as a derivative of benzene. These names are retained:

The position of substituents is indicated by numbers, with the lowest locant possible given to substituents. When a name is based on a recognized trivial name, priority for lowest-numbered locants is given to substituents implied by the trivial name. When only two substituents are present on a benzene ring, their position may be indicated by o- (ortho-), m- (meta-), and p- (para-) (and alphabetized in the order given) used in place of 1,2-, 1,3-, and 1,4-, respectively. Radicals derived from monocyclic substituted aromatic hydrocarbons and having the free valence at a ring atom (numbered 1) are named phenyl (for benzene as parent, since benzyl is used for the radical C6H5CH2 ˆ ), cumenyl, mesityl, tolyl, and xylyl. All other radicals are named as substituted phenyl radicals. For radicals having a single free valence in the side chain, these trivial names are retained:

ORGANIC COMPOUNDS

Benzyl C6H5CH2 ˆ Benzhydryl (alternative to diphenylmethyl) (C6H5)2CH ˆ Cinnamyl C6H5CH ¨ CH ˆ CH2 ˆ

1.7

Phenethyl C6H5CH2CH2 ˆ Styryl C6H5CH ¨ CH ˆ Trityl (C6H5)3C ˆ

Otherwise, radicals having the free valence(s) in the side chain are named in accordance with the rules for alkanes, alkenes, or alkynes. The name phenylene (o-, m-, or p-) is retained for the radical ˆ C6H4 ˆ . Bivalent radicals formed from substituted benzene derivatives and having the free valences at ring atoms are named as substituted phenylene radicals, with the carbon atoms having the free valences being numbered 1,2-, 1,3-, or 1,4-, as appropriate. Radicals having three or more free valences are named by adding the suffixes -triyl, -tetrayl, etc. to the systematic name of the corresponding hydrocarbon. Fused Polycyclic Hydrocarbons. The names of polycyclic hydrocarbons containing the maximum number of conjugated double bonds end in -ene. Here the ending does not denote one double bond. Names of hydrocarbons containing five or more fixed benzene rings in a linear arrangement are formed from a numerical prefix (see Table 11.4) followed by -acene. A partial list of the names of polycyclic hydrocarbons is given in Table 1.2. Many names are trivial. Numbering of each ring system is fixed, as shown in Table 1.2, but it follows a systematic pattern. The individual rings of each system are oriented so that the greatest number of rings are (1) in a horizontal row and (2) the maximum number of rings are above and to the right (upper-right quadrant) of the horizontal row. When two orientations meet these requirements, the one is chosen that has the fewest rings in the lower-left quadrant. Numbering proceeds in a clockwise direction, commencing with the carbon atom not engaged in ring fusion that lies in the most counterclockwise position of the uppermost ring (upper-right quadrant); omit atoms common to two or more rings. Atoms common to two or more rings are designated by adding lowercase roman letters to the number of the position immediately preceding. Interior atoms follow the highest number, taking a clockwise sequence wherever there is a choice. Anthracene and phenanthrene are two exceptions to the rule on numbering. Two examples of numbering follow:

When a ring system with the maximum number of conjugated double bonds can exist in two or more forms differing only in the position of an “extra” hydrogen atom, the name can be made specific by indicating the position of the extra hydrogen(s). The compound name is modified with a locant followed by an italic capital H for each of these hydrogen atoms. Carbon atoms that carry an indicated hydrogen atom are numbered as low as possible. For example, 1H-indene is illustrated in Table 1.2; 2H-indene would be

Names of polycyclic hydrocarbons with less than the maximum number of noncumulative double bonds are formed from a prefix dihydro-, tetrahydro-, etc., followed by the

1.8

SECTION 1

name of the corresponding unreduced hydrocarbon. The prefix perhydro- signifies full hydrogenation. For example, 1,2-dihydronaphthalene is

TABLE 1.2 Fused Polycyclic Hydrocarbons Listed in order of increasing priority for selection as parent compound Asterisk after a compound denotes exception to systematic numbering.

ORGANIC COMPOUNDS

1.9

TABLE 1.2 Fused Polycyclic Hydrocarbons (continued ) Listed in order of increasing priority for selection as parent compound Asterisk after a compound denotes exception to systematic numbering.

Examples of retained names and their structures are as follows:

Polycyclic compounds in which two rings have two atoms in common or in which one ring contains two atoms in common with each of two or more rings of a contiguous series of rings and which contain at least two rings of five or more members with the maximum number of noncumulative double bonds and which have no accepted trivial name (Table 1.2) are named by prefixing to the name of the parent ring or ring system designations of the other components. The parent name should contain as many rings as possible (provided it has a trivial name) and should occur as far as possible from the beginning of the list in Table 1.2. Furthermore, the attached component(s) should be as simple as possible. For example, one writes dibenzo phenanthrene and not naphthophenanthrene because the attached component benzo- is simpler than naphtho-. Prefixes designating attached components are formed by changing the ending -ene into -eno-; for example, indeno- from

1.10

SECTION 1

indene. Multiple prefixes are arranged in alphabetical order. Several abbreviated prefixes are recognized; the parent is given in parentheses: Acenaphtho(acenaphthylene) Anthra(anthracene) Benzo(benzene)

Naphtho(naphthalene) Perylo(perylene) Phenanthro(phenanthrene)

For monocyclic prefixes other than benzo-, the following names are recognized, each to represent the form with the maximum number of noncumulative double bonds: cyclopenta-, cyclohepta-, cycloocta-, etc. Isomers are distinguished by lettering the peripheral sides of the parent beginning with a for the side 1,2-, and so on, lettering every side around the periphery. If necessary for clarity, the numbers of the attached position (1,2-, for example) of the substituent ring are also denoted. The prefixes are cited in alphabetical order. The numbers and letters are enclosed in square brackets and placed immediately after the designation of the attached component. Examples are

Bridged Hydrocarbons. Saturated alicyclic hydrocarbon systems consisting of two rings that have two or more atoms in common take the name of the open-chain hydrocarbon containing the same total number of carbon atoms and are preceded by the prefix bicyclo-. The system is numbered commencing with one of the bridgeheads, numbering proceeding by the longest possible path to the second bridgehead. Numbering is then continued from this atom by the longer remaining unnumbered path back to the first bridgehead and is completed by the shortest path from the atom next to the first bridgehead. When a choice in numbering exists, unsaturation is given the lowest numbers. The number of carbon atoms in each of the bridges connecting the bridgeheads is indicated in brackets in descending order. Examples are

Hydrocarbon Ring Assemblies. Assemblies are two or more cyclic systems, either single rings or fused systems, that are joined directly to each other by double or single bonds. For identical systems naming may proceed (1) by placing the prefix bi- before the name of the corresponding radical or (2) for systems joined through a single bond, by placing the prefix bi- before the name of the corresponding hydrocarbon. In each case, the numbering of the assembly is that of the corresponding radical or hydrocarbon, one system being assigned unprimed numbers and the other primed numbers. The points of attachment

ORGANIC COMPOUNDS

1.11

are indicated by placing the appropriate locants before the name; an unprimed number is considered lower than the same number primed. The name biphenyl is used for the assembly consisting of two benzene rings. Examples are

For nonidentical ring systems, one ring system is selected as the parent and the other systems are considered as substituents and are arranged in alphabetical order. The parent ring system is assigned unprimed numbers. The parent is chosen by considering the following characteristics in turn until a decision is reached: (1) the system containing the larger number of rings, (2) the system containing the larger ring, (3) the system in the lowest state of hydrogenation, and (4) the highest-order number of ring systems set forth in Table 1.2. Examples are given, with the deciding priority given in parentheses preceding the name: (1) 2-Phenylnaphthalene (2) and (4) 2-(2-Naphthyl)azulene (3) Cyclohexylbenzene Radicals from Ring Systems. Univalent substituent groups derived from polycyclic hydrocarbons are named by changing the final e of the hydrocarbon name to -yl. The carbon atoms having free valences are given locants as low as possible consistent with the fixed numbering of the hydrocarbon. Exceptions are naphthyl (instead of naphthalenyl), anthryl (for anthracenyl), and phenanthryl (for phenanthrenyl). However, these abbreviated forms are used only for the simple ring systems. Substituting groups derived from fused derivatives of these ring systems are named systematically. Substituting groups having two or more free bonds are named as described in Monocyclic Aliphatic Hydrocarbons on p. 1.5. Cyclic Hydrocarbons with Side Chains. Hydrocarbons composed of cyclic and aliphatic chains are named in a manner that is the simplest permissible or the most appropriate for the chemical intent. Hydrocarbons containing several chains attached to one cyclic nucleus are generally named as derivatives of the cyclic compound, and compounds containing several side chains and/or cyclic radicals attached to one chain are named as derivatives of the acyclic compound. Examples are 2-Ethyl-1-methylnaphthalene 1,5-Diphenylpentane

Diphenylmethane 2,3-Dimethyl-1-phenyl-1-hexene

Recognized trivial names for composite radicals are used if they lead to simplifications in naming. Examples are 1-Benzylnaphthalene

1,2,4-Tris(3-p-tolylpropyl)benzene

1.12

SECTION 1

Fulvene, for methylenecyclopentadiene, and stilbene, for 1,2-diphenylethylene, are trival names that are retained. Heterocyclic Systems. Heterocyclic compounds can be named by relating them to the corresponding carbocyclic ring systems by using replacement nomenclature. Heteroatoms are denoted by prefixes ending in -a, as shown in Table 1.3. If two or more replacement prefixes are required in a single name, they are cited in the order of their listing in the table. The lowest possible numbers consistent with the numbering of the corresponding carbocyclic system are assigned to the heteroatoms and then to carbon atoms bearing double

TABLE 1.3 Specialist Nomenclature for Heterocyclic Systems Heterocyclic atoms are listed in decreasing order of priority

Element Oxygen Sulfur Selenium Tellurium Nitrogen Phosphorus Arsenic

Valence

Prefix

Element

Valence

Prefix

2 2 2 2 3 3 3

OxaThiaSelenaTelluraAzaPhospha-* Arsa-*

Antimony Bismuth Silicon Germanium Tin Lead Boron Mercury

3 3 4 4 4 4 3 2

Stiba-* BismaSilaGermaStannaPlumbaBoraMercura-

* When immediately followed by -in or -ine, phospha- should be replaced by phosphor-, arsa- by arsen-, and stiba- by antimon-. The saturated six-membered rings corresponding to phosphorin and arsenin are named phosphorinane and arsenane. A further exception is the replacement of borin by borinane.

TABLE 1.4 Suffixes for Specialist Nomenclature of Heterocyclic Systems Number of ring members 3 4 5 6 7 8 9 10

Rings containing nitrogen Unsaturation* -irine -ete -ole -ine† -epine -ocine -onine -ecine

Rings containing no nitrogen

Saturation

Unsaturation*

-iridine -etidine -olidine ‡ ‡ ‡ ‡ ‡

-irene -ete -ole -in -epin -ocin -onin -ecin

Saturation -irane -etane -olane -ane§ -epane -ocane -onane -ecane

* Unsaturation corresponding to the maximum number of noncumulative double bonds. Heteroatoms have the normal valences given in Table 1.3. † For phosphorus, arsenic, antimony, and boron, see the special provisions in Table 1.3. ‡ Expressed by prefixing perhydro- to the name of the corresponding unsaturated compound. § Not applicable to silicon, germanium, tin, and lead; perhydro- is prefixed to the name of the corresponding unsaturated compound.

1.13

ORGANIC COMPOUNDS

TABLE 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names Listed in order of increasing priority as senior ring system Asterisk after a compound denotes exception to systematic numbering.

Structure

Parent name

Radical name

Structure

Parent name

Radical name

1.14

SECTION 1

TABLE 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names (continued ) Listed in order of increasing priority as senior ring system Asterisk after a compound denotes exception to systematic numbering.

Structure

Parent name Radical name

Structure

Parent name

Radical name

1.15

ORGANIC COMPOUNDS

TABLE 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names (continued ) Listed in order of increasing priority as senior ring system Asterisk after a compound denotes exception to systematic numbering.

Structure

Parent name

Radical name

Structure

Parent name

Radical name

or triple bonds. Locants are cited immediately preceding the prefixes or suffixes to which they refer. Multiplicity of the same heteroatom is indicated by the appropriate prefix in the series: di-, tri-, tetra-, penta-, hexa-, etc. If the corresponding carbocyclic system is partially or completely hydrogenated, the additional hydrogen is cited using the appropriate H- or hydro- prefixes. A trivial name from Tables 1.5 and 1.6, if available, along with the state of hydrogenation may be used. In the specialist nomenclature for heterocyclic systems, the prefix or prefixes from

1.16

SECTION 1

TABLE 1.6 Trivial Names for Heterocyclic Systems that are Not Recommended for Use in Fusion Names Listed in order of increasing priority

Structure

Parent name

Radical name

* Denotes position of double bond. † For 1-piperidyl, use piperidino. ‡ For 4-morpholinyl, use morpholino.

Structure

Parent name

Radical name

ORGANIC COMPOUNDS

1.17

Table 1.3 are combined with the appropriate stem from Table 1.4, eliding an -a where necessary. Examples of acceptable usage, including (1) replacement and (2) specialist nomenclature, are

Radicals derived from heterocyclic compounds by removal of hydrogen from a ring are named by adding -yl to the names of the parent compounds (with elision of the final e, if present). These exceptions are retained: Furyl (from furan) Pyridyl (from pyridine) Piperidyl (from piperidine) Quinolyl (from quinoline) Isoquinolyl Thenylidene (for thienylmethylene)

Furfuryl (for 2-furylmethyl) Furfurylidene (for 2-furylmethylene) Thienyl (from thiophene) Thenylidyne (for thienylmethylidyne) Furfurylidyne (for 2-furylmethylidyne) Thenyl (for thienylmethyl)

Also, piperidino- and morpholino- are preferred to 1-piperidyl- and 4-morpholinyl-, respectively. If there is a choice among heterocyclic systems, the parent compound is decided in the following order of preference: 1. A nitrogen-containing component 2. A component containing a heteroatom, in the absence of nitrogen, as high as possible in Table 1.3 3. A component containing the greatest number of rings 4. A component containing the largest possible individual ring 5. A component containing the greatest number of heteroatoms of any kind 6. A component containing the greatest variety of heteroatoms 7. A component containing the greatest number of heteroatoms first listed in Table 1.3 If there is a choice between components of the same size containing the same number and kind of heteroatoms, choose as the base component that one with the lower numbers for the heteroatoms before fusion. When a fusion position is occupied by a heteroatom, the names of the component rings to be fused are selected to contain the heteroatom. Common Names of Heterocycles Used Broadly in Biology. The naming of heterocycles by systematic methods is important but cumbersome for designating some of the most commonly occurring heterocycles. In particular, the bases that occur in ribonucleic acids (RNA) and deoxyribonucleic acids (DNA) have specific substitution patterns. Because they occur so commonly, they have been given trivial names that are invariably used when discussed or named in the biological literature.

1.18

SECTION 1 Base pairing is the most common (Watson-Crick) arrangement. H N H O N N N N N sugar O N sugar H N H cytosine:::guanine H3C

N sugar

O N H

H N

H N

N

N N

O

sugar

thymine::adenine The individual elements of RNA and DNA chains. O O N

NH N HO H

H

O 3'

H OH

O P O–

5'

HO

O H

N

O

5'

H

O–

O ribose

H

O 3'

H

P

N

NH2

O

H

O–

NH

H

O– deoxyribose

FIGURE 1.2 Base pairing in the most common (Watson–Crick) arrangement. The individual elements of RNA and DNA chains are shown in the lower panel of the figure. Hollow arrows indicate the points at which the 5-hydroxyl group is esterified to the 3-phosphate group to form the so-called “sugar–phosphate” backbone. Note the hydroxyl group (arrow) that is present on ribose but missing in deoxyribose.

The structural frameworks of DNA and RNA are organized by hydrogen bond formation between pairs of purine and pyrimidine bases. The pyrimidines are shown near the end of Table 1.5. Cytosine (C) and thymine (T) occur in DNA and form hydrogen-bonded pairs with the purines guanine (G) and adenine (A), respectively. The base pairs are abbreviated AT and GC, sometimes with dotted lines connecting them. The AT pair is held together by two hydrogen bonds and may be represented in shorthand as A::T. Three H-bonds hold together guanine and cytosine, giving G:::C. The so-called Watson–Crick base pairing is shown in Figure 1.2. In RNA, uracil replaces thymine but pairing still occurs with adenine to give A::U. An alternative form of hydrogen bonding between base pairs is designated “Hoogsteen.” This type of bonding cannot readily occur in nature because the purine and pyrimidine bases are constrained to long chains that must interact at numerous points. Functionalized Compounds There are several types of nomenclature systems that are recognized. Which type to use is sometimes obvious from the nature of the compound. Substitutive nomenclature, in general, is preferred because of its broad applicability, but radicofunctional, additive, and replacement nomenclature systems are convenient in certain situations.

1.19

ORGANIC COMPOUNDS

Substitutive Nomenclature. The first step is to determine the kind of characteristic (functional) group for use as the principal group of the parent compound. A characteristic group is a recognized combination of atoms that confers characteristic chemical properties on the molecule in which it occurs. Carbon-to-carbon unsaturation and heteroatoms in rings are considered nonfunctional for nomenclature purposes. Substitution means the replacement of one or more hydrogen atoms in a given compound by some other kind of atom or group of atoms, functional or nonfunctional. In substitutive nomenclature, each substituent is cited as either a prefix or a suffix to the name of the parent (or substituting radical) to which it is attached; the latter is denoted the parent compound (or parent group if a radical). In Table 1.7 are listed the general classes of compounds in descending order of preference for citation as suffixes, that is, as the parent or characteristic compound. When oxygen is TABLE 1.7 Characteristic Groups for Substitutive Nomenclature Listed in order of decreasing priority for citation as principal group or parent name

Class

Formula*

1. Cations H4N H3O H3S H3Se H2Cl H2Br H2I 2. Acids Carboxylic

Sulfonic Sulfinic Sulfenic Salts

3. Derivatives of acids Anhydrides Esters Acid halides Amides

ˆ COOH ˆ (C)OOH ˆ C( ¨ O)OOH ˆ (C ¨ O)OOH ˆ SO3H ˆ SO2H ˆ SOH ˆ COOM ˆ (C)OOM ˆ SO3M ˆ SO2M ˆ SOM

ˆ C( ¨ O)OC( ¨ O) ˆ ˆ (C ¨ O)O(C ¨ O) ˆ ˆ COOR ˆ C(OOR) ˆ CO ˆ halogen ˆ CO ˆ NH2 (C)O ˆ NH2

Prefix

Suffix

-onioAmmonioOxonioSulfonioSelenonioChloronioBromonioIodonio-

-onium -ammonium -oxonium -sulfonium -selenonium -chloronium -bromonium -iodonium

Carboxy-

-carboxylic acid -oic acid -peroxy · · · carboxylic acid -peroxy · · · oic acid -sulfonic acid -sulfinic acid -sulfenic acid Metal · · · carboxylate Metal · · · oate Metal · · · sulfonate Metal · · · sulfinate Metal · · · sulfenate

SulfoSulfinoSulfeno-

R-oxycarbonylHaloformyl Carbamoyl-

-carboxylic anhydride -oic anhydride R · · · carboxylate R · · · oate -carbonyl halide -carboxamide -amide

1.20

SECTION 1

TABLE 1.7 Characteristic Groups for Substitutive Nomenclature (continued) Listed in order of decreasing priority for citation as principal group or parent name

Class Hydrazides Imides Amidines

Formula*

Prefix

ˆ CO ˆ NHNH2 ˆ (CO) ˆ NHNH2 ˆ CO ˆ NH ˆ CO ˆ ˆ C( ¨ NH) ˆ NH2 ˆ (C ¨ NH) ˆ NH2

Carbonyl-hydrazinoR-imidoAmidinoCyano-

Suffix -carbohydrazide -ohydrazide -carboximide -carboxamidine -amidine

4. Nitrile (cyanide)

ˆ CN ˆ (C)N

-carbonitrile -nitrile

5. Aldehydes

ˆ CHO Formylˆ (C ¨ O)H Oxo(then their analogs and derivatives)

-carbaldehyde -al

6. Ketones

a(C ¨ O) Oxo(then their analogs and derivatives)

-one

7. Alcohols (and phenols) Thiols

ˆ OH

Hydroxy-

-ol

ˆ SH

Mercapto-

-thiol

8. Hydroperoxides

ˆ O ˆ OH

Hydroperoxy-

9. Amines Imines Hydrazines

ˆ NH2 ¨ NH ˆ NHNH2

AminoIminoHydrazino-

10. Ethers Sulfides

ˆ OR ˆ SR

R-oxyR-thio-

11. Peroxides

ˆ O ˆ OR

R-dioxy-

-amine -imine -hydrazine

* Carbon atoms enclosed in parentheses are included in the name of the parent compound and not in the suffix or prefix.

replaced by sulfur, selenium, or tellurium, the priority for these elements is in the descending order listed. The higher valence states of each element are listed before considering the successive lower valence states. Derivative groups have priority for citation as principal group after the respective parents of their general class. In Table 1.8 are listed characteristic groups that are cited only as prefixes (never as suffixes) in substitutive nomenclature. The order of listing has no significance for nomenclature purposes. Systematic names formed by applying the principles of substitutive nomenclature are single words except for compounds named as acids. First one selects the parent compound, and thus the suffix, from the characteristic group listed earliest in Table 1.7. All remaining functional groups are handled as prefixes that precede, in alphabetical order, the parent name. Two examples may be helpful:

1.21

ORGANIC COMPOUNDS

TABLE 1.8 Characteristic Groups Cited Only as Prefixes in Substitutive Nomenclature Characteristic group

Prefix

ˆ Br

Bromo-

ˆ Cl ˆ ClO ˆ ClO2 ˆ ClO3 ˆF ˆI ˆ IO

ChloroChlorosylChlorylPerchlorylFluoroIodoIodosyl-

ˆ IO2 ˆ I(OH)2

Iodyl* Dihydroxyiodo-

Characteristic group

Prefix

ˆ IX2

X may be halogen or a radical; dihalogenoiodoor diacetoxyiodo-, e.g., ˆ ICl2 is dichloroido-

¨ N ¨ N ˆ N3, ˆ N ¨ N ¨ N ˆN ¨ O O ˆ NO2, ˆ N O OH ¨ N ˆ OR O ˆ SR ˆ SeR ( ˆ TeR)

DiazoAzidoNitrosoNitroaci-NitroR-oxy-; alkoxy- or aryloxyR-thio-; alkylthio- or arylthioR-seleno- (R-telluro-)

* Formerly iodoxy-.

Structure 1 contains an ester group and an ether group. Since the ester group has higher priority, the name is ethyl 2-methoxy-6-methyl-3-cyclohexene-1-carboxylate. Structure 2 contains a carbonyl group, an hydroxy group, and a bromo group. The latter is never a suffix. Between the other two, the carbonyl group has higher priority, the parent has -one as suffix, and the name is 4-bromo-1-hydroxy-2-butanone. Selection of the principal alicyclic chain or ring system is governed by the following selection rules: 1. For purely alicyclic compounds, the selection process proceeds successively until a decision is reached: (a) the maximum number of substituents corresponding to the characteristic group cited earliest in Table 1.7, (b) the maximum number of double and triple bonds considered together, (c) the maximum length of the chain, and (d) the maximum number of double bonds. Additional criteria, if needed for complicated compounds, are given in the IUPAC nomenclature rules. 2. If the characteristic group occurs only in a chain that carries a cyclic substituent, the compound is named as an aliphatic compound into which the cyclic component is substituted; a radical prefix is used to denote the cyclic component. This chain need not be the longest chain. 3. If the characteristic group occurs in more than one carbon chain and the chains are not directly attached to one another, then the chain chosen as parent should carry the largest number of the characteristic group. If necessary, the selection is continued as in rule 1. 4. If the characteristic group occurs only in one cyclic system, that system is chosen as the parent. 5. If the characteristic group occurs in more than one cyclic system, that system is chosen as parent which (a) carries the largest number of the principal group or, failing to reach a decision, (b) is the senior ring system. 6. If the characteristic group occurs both in a chain and in a cyclic system, the parent is that portion in which the principal group occurs in largest number. If the numbers are the same, that portion is chosen which is considered to be the most important or is the senior ring system.

1.22

SECTION 1

7. When a substituent is itself substituted, all the subsidiary substituents are named as prefixes and the entire assembly is regarded as a parent radical. 8. The seniority of ring systems is ascertained by applying the following rules successively until a decision is reached: (a) all heterocycles are senior to all carbocycles, (b) for heterocycles, the preference follows the decision process described under “Heterocyclic Systems,” page 1–12, (c) the largest number of rings, (d ) the largest individual ring at the first point of difference, (e) the largest number of atoms in common among rings, ( f ) the lowest letters in the expression for ring functions, (g) the lowest numbers at the first point of difference in the expression for ring junctions, (h) the lowest state of hydrogenation, (i) the lowest-numbered locant for indicated hydrogen, ( j) the lowestnumbered locant for point of attachment (if a radical), (k) the lowest-numbered locant for an attached group expressed as a suffix, (l) the maximum number of substituents cited as prefixes, (m) the lowest-numbered locant for substituents named as prefixes, hydro prefixes, -ene, and -yne, all considered together in one series in ascending numerical order independent of their nature, and (n) the lowest-numbered locant for the substituent named as prefix which is cited first in the name. Numbering of Compounds. If the rules for aliphatic chains and ring systems leave a choice, the starting point and direction of numbering of a compound are chosen so as to give lowest-numbered locants to these structural factors, if present, considered successively in the order listed below until a decision is reached. Characteristic groups take precedence over multiple bonds. 1. Indicated hydrogen, whether cited in the name or omitted as being conventional. 2. Characteristic groups named as suffix following the ranking order of Table 1.7. 3. Multiple bonds in acyclic compounds; in bicycloalkanes, tricycloalkanes, and polycycloalkanes, double bonds having priority over triple bonds; and in heterocyclic systems whose names end in -etine, -oline, or -olene. 4. The lowest-numbered locant for substituents named as prefixes, hydro prefixes, -ene, and -yne, all considered together in one series in ascending numerical order. 5. The lowest locant for that substituent named as prefix which is cited first in the name. For cyclic radicals, indicated hydrogen and thereafter the point of attachment (free valency) have priority for the lowest available number. Prefixes and Affixes. Prefixes are arranged alphabetically and placed before the parent name; multiplying affixes, if necessary, are inserted and do not alter the alphabetical order already attained. The parent name includes any syllables denoting a change of ring member or relating to the structure of a carbon chain. Nondetachable parts of parent names include 1. 2. 3. 4. 5. 6. 7.

Forming rings: cyclo-, bicyclo-, spiro-; Fusing two or more rings: benzo-, naphtho-, imidazo-; Substituting one ring or chain member atom for another: oxa-, aza-, thia-; Changing positions of ring or chain members: iso-, sec-, tert-, neo-; Showing indicated hydrogen; Forming bridges: ethano-, epoxy- and; Hydro-.

ORGANIC COMPOUNDS

1.23

Prefixes that represent complete terminal characteristic groups are preferred to those representing only a portion of a given group. For example, for the group ˆ C( ¨ O)CH3, the prefix (formylmethyl-) is preferred to (oxoethyl-). The multiplying affixes di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca-, and so on are used to indicate a set of identical unsubstituted radicals or parent compounds. The forms bis-, tris-, tetrakis-, pentakis-, and so on are used to indicate a set of identical radicals or parent compounds each substituted in the same way. The affixes bi-, ter-, quater-, quinque-, sexi, septi-, octi-, novi-, deci-, and so on are used to indicate the number of identical rings joined together by a single or double bond. Although multiplying affixes may be omitted for very common compounds when no ambiguity is caused thereby, such affixes are generally included throughout this handbook in alphabetical listings. An example would be ethyl ether for diethyl ether. Conjunctive Nomenclature. Conjunctive nomenclature may be applied when a principal group is attached to an acyclic component that is directly attached by a carbon–carbon bond to a cyclic component. The name of the cyclic component is attached directly in front of the name of the acyclic component carrying the principal group. This nomenclature is not used when an unsaturated side chain is named systematically. When necessary, the position of the side chain is indicated by a locant placed before the name of the cyclic component. For substituents on the acyclic chain, carbon atoms of the side chain are indicated by Greek letters proceeding from the principal group to the cyclic component. The terminal carbon atom of acids, aldehydes, and nitriles is omitted when allocating Greek positional letters. Conjunctive nomenclature is not used when the side chain carries more than one of the principal group, except in the case of malonic and succinic acids. The side chain is considered to extend only from the principal group to the cyclic component. Any other chain members are named as substituents, with appropriate prefixes placed before the name of the cyclic component. When a cyclic component carries more than one identical side chain, the name of the cyclic component is followed by di-, tri-, etc., and then by the name of the acyclic component, and it is preceded by the locants for the side chains. Examples are

When side chains of two or more different kinds are attached to a cyclic component, only the senior side chain is named by the conjunctive method. The remaining side chains are named as prefixes. Likewise, when there is a choice of cyclic component, the senior is chosen. Benzene derivatives may be named by the conjunctive method only when two or more identical side chains are present. Trivial names for oxo carboxylic acids may be used for the acyclic component. If the cyclic and acyclic components are joined by a double bond, the locants of this bond are placed as superscripts to a Greek capital delta that is

1.24

SECTION 1

inserted between the two names. The locant for the cyclic component precedes that for the acyclic component, e.g., indene-1,-acetic acid. Radicofunctional Nomenclature. The procedures of radicofunctional nomenclature are identical with those of substitutive nomenclature except that suffixes are never used. Instead, the functional class name (Table 1.9) of the compound is expressed as one word and the remainder of the molecule as another that precedes the class name. When the functional class name refers to a characteristic group that is bivalent, the two radicals attached to it are each named, and when different, they are written as separate words arranged in alphabetical order. When a compound contains more than one kind of group listed in Table 1.9, that kind is cited as the functional group or class name that occurs higher in the table, all others being expressed as prefixes. Radicofunctional nomenclature finds some use in naming ethers, sulfides, sulfoxides, sulfones, selenium analogs of the preceding three sulfur compounds, and azides.

TABLE 1.9 Functional Class Names Used in Radicofunctional Nomenclature Groups are listed in order of decreasing priority

Group X in acid derivatives ˆ CN, ˆ NC aCO ˆ OH ˆ O ˆ OH aO aS, aSO, aSO2 aSe, aSeO, aSeO2 ˆ F, ˆ Cl, ˆ Br, ˆ I ˆ N3

Functional class names Name of X (in priority order: fluoride, chloride, bromide, iodide; cyanide, azide; then the sulfur and selenium analogs) Cyanide, isocyanide Ketone; then S and Se analogs Alcohol; then S and Se analogs Hydroperoxide Ether or oxide Sulfide, sulfoxide, sulfone Selenide, selenoxide, selenone Fluoride, chloride, bromide, iodide Azide

Replacement Nomenclature. Replacement nomenclature is intended for use only when other nomenclature systems are difficult to apply in the naming of chains containing heteroatoms. When no group is present that can be named as a principal group, the longest chain of carbon and heteroatoms terminating with carbon is chosen and named as though the entire chain were that of an acyclic hydrocarbon. The heteroatoms within this chain are identified by means of prefixes aza-, oxa-, thia-, etc., in the order of priority stated in Table 1.3. Locants indicate the positions of the heteroatoms in the chain. Lowest-numbered locants are assigned to the principal group when such is present. Otherwise, lowestnumbered locants are assigned to the heteroatoms considered together and, if there is a choice, to the heteroatoms cited earliest in Table 1.3. An example is

ORGANIC COMPOUNDS

1.25

Specific Functional Groups Characteristic groups will now be treated briefly in order to expand the terse outline of substitutive nomenclature presented in Table 1.7. Alternative nomenclature will be indicated whenever desirable. Acetals and Acylals. Acetals, which contain the group C(OR)2, where R may be different, are named (1) as dialkoxy compounds or (2) by the name of the corresponding aldehyde or ketone followed by the name of the hydrocarbon radical(s) followed by the word acetal. For example, CH3 ˆ CH(OCH3)2 is named either (1) 1,1-dimethoxyethane or (2) acetaldehyde dimethyl acetal. A cyclic acetal in which the two acetal oxygen atoms form part of a ring may be named (1) as a heterocyclic compound or (2) by use of the prefix methylenedioxy for the group ˆ O ˆ CH2 ˆ O ˆ as a substituent in the remainder of the molecule. For example,

-Hydroxy ketones, formerly called acyloins, had been named by changing the ending -ic acid or -oic acid of the corresponding acid to -oin. They are preferably named by substitutive nomenclature. For example, CH3 ˆ CH(OH3) ˆ CO ˆ CH3

3-Hydroxy-2-butanone (formerly acetoin)

Acid Anhydrides. Symmetrical anhydrides of monocarboxylic acids, when unsubstituted, are named by replacing the word acid by anhydride. Anhydrides of substituted monocarboxylic acids, if symmetrically substituted, are named by prefixing bis- to the name of the acid and replacing the word acid by anhydride. Mixed anhydrides are named by giving in alphabetical order the first part of the names of the two acids followed by the word anhydride, e.g., acetic propionic anhydride or acetic propanoic anhydride. Cyclic anhydrides of polycarboxylic acids, although possessing a heterocyclic structure, are preferably named as acid anhydrides. For example,

1.26

SECTION 1

Acyl Halides. Acyl halides, in which the hydroxyl portion of a carboxyl group is replaced by a halogen, are named by placing the name of the corresponding halide after that of the acyl radical. When another group is present that has priority for citation as principal group or when the acyl halide is attached to a side chain, the prefix haloformyl- is used as, for example, in fluoroformyl-. Alcohols and Phenols. The hydroxyl group is indicated by a suffix -ol when it is the principal group attached to the parent compound and by the prefix hydroxy- when another group with higher priority for citation is present or when the hydroxy group is present in a side chain. When confusion may arise in employing the suffix -ol, the hydroxy group is indicated as a prefix; this terminology is also used when the hydroxyl group is attached to a heterocycle, as, for example, in the name 3-hydroxythiophene to avoid confusion with thiophenol (C6H5SH). Designations such as isopropanol, sec-butanol, and tert-butanol are incorrect because no hydrocarbon exists to which the suffix can be added. Many trivial names are retained. These structures are shown in Table 1.10. The radicals (RO ˆ ) are named by adding -oxy as a suffix to the name of the R radical, e.g., pentyloxy for CH3CH2CH2CH2CH2O ˆ . These contractions are exceptions: methoxy (CH3O ˆ ), ethoxy (C2H5O ˆ ), propoxy (C3H7O ˆ ), butoxy (C4H9O ˆ ), and phenoxy (C6H5O ˆ ). For unsubstituted radicals only, one may use isopropoxy [(CH3)2CH ˆ O ˆ ], isobutoxy [(CH3)2CH2CH ˆ O ˆ ], sec-butoxy [CH3CH2CH(CH3) ˆ O ˆ ], and tert-butoxy [(CH3)3C ˆ O ˆ ].

TABLE 1.10 Retained Trivial Names of Alcohols and Phenols with Structures

ORGANIC COMPOUNDS

1.27

TABLE 1.10 Retained Trivial Names of Alcohols and Phenols with Structures (continued )

Bivalent radicals of the form O ˆ Y ˆ O are named by adding -dioxy to the name of the bivalent radicals except when forming part of a ring system. Examples are ˆ O ˆ CH2 ˆ O ˆ (methylenedioxy), ˆ O ˆ CO ˆ O ˆ (carbonyldioxy), and ˆ O ˆ SO2 ˆ O ˆ (sulfonyldioxy). Anions derived from alcohols or phenols are named by changing the final -ol to -olate.

1.28

SECTION 1

Salts composed of an anion, RO ˆ , and a cation, usually a metal, can be named by citing first the cation and then the RO anion (with its ending changed to -yl oxide), e.g., sodium benzyl oxide for C6H5CH2ONa. However, when the radical has an abbreviated name, such as methoxy, the ending -oxy is changed to -oxide. For example, CH3ONa is named sodium methoxide (not sodium methylate). Aldehydes. When the group ˆ C( ¨ O)H, usually written ˆ CHO, is attached to carbon at one (or both) end(s) of a linear acyclic chain the name is formed by adding the suffix -al (or -dial) to the name of the hydrocarbon containing the same number of carbon atoms. Examples are butanal for CH3CH2CH2CHO and propanedial for OHCCH2CHO. Naming an acyclic polyaldehyde can be handled in two ways. (1) When more than two aldehyde groups are attached to an unbranched chain, the proper affix is added to -carbaldehyde, which becomes the suffix to the name of the longest chain carrying the maximum number of aldehyde groups. The name and numbering of the main chain do not include the carbon atoms of the aldehyde groups. (2) The name is formed by adding the prefix formyl- to the name of the -dial that incorporates the principal chain. Any other chains carrying aldehyde groups are named by the use of formylalkyl- prefixes. Examples are

When the aldehyde group is directly attached to a carbon atom of a ring system, the suffix -carbaldehyde is added to the name of the ring system, e.g., 2-naphthalenecarbaldehyde. When the aldehyde group is separated from the ring by a chain of carbon atoms, the compound is named (1) as a derivative of the acyclic system or (2) by conjunctive nomenclature, for example, (1) (2-naphthyl)propionaldehyde or (2) 2-naphthalenepropionaldehyde. An aldehyde group is denoted by the prefix formyl- when it is attached to a nitrogen atom in a ring system or when a group having priority for citation as principal group is present and part of a cyclic system. When the corresponding monobasic acid has a trivial name, the name of the aldehyde may be formed by changing the ending -ic acid or -oic acid to -aldehyde. Examples are Formaldehyde Acetaldehyde Propionaldehyde Butyraldehyde

Acrylaldehyde (not acrolein) Benzaldehyde Cinnamaldehyde 2-Furaldehyde (not furfural)

ORGANIC COMPOUNDS

1.29

The same is true for polybasic acids, with the proviso that all the carboxyl groups must be changed to aldehyde; then it is not necessary to introduce affixes. Examples are Glyceraldehyde Glycolaldehyde Malonaldehyde

Succinaldehyde Phthalaldehyde (o-, m-, p-)

These trivial names may be retained: citral (3,7-dimethyl-2,6-octadienal), vanillin (4-hydroxy-3-methoxybenzaldehyde), and piperonal (3,4-methylenedioxybenzaldehyde). Amides. For primary amides the suffix -amide is added to the systematic name of the parent acid. For example, CH3 ˆ CO ˆ NH2 is acetamide. Oxamide is retained for H2N ˆ CO ˆ CO ˆ NH2. The name -carboxylic acid is replaced by -carboxamide. For amino acids having trivial names ending in -ine, the suffix -amide is added after the name of the acid (with elision of -e for monoamides). For example, H2N ˆ CH2 ˆ CO ˆ NH2 is glycinamide. In naming the radical R ˆ CO ˆ NH ˆ , either (1) the -yl ending of RCO ˆ is changed to -amido or (2) the radicals are named as acylamino radicals. For example,

The latter nomenclature is always used for amino acids with trivial names. N-substituted primary amides are named either (1) by citing the substituents as N prefixes or (2) by naming the acyl group as an N substituent of the parent compound. For example,

Amines. Amines are preferably named by adding the suffix -amine (and any multiplying affix) to the name of the parent radical. Examples are

Locants of substituents of symmetrically substituted derivatives of symmetrical amines are distinguished by primes or else the names of the complete substituted radicals are enclosed in parentheses. Unsymmetrically substituted derivatives are named similarly or as N-substituted products of a primary amine (after choosing the most senior of the radicals to be the parent amine). For example,

1.30

SECTION 1

Complex cyclic compounds may be named by adding the suffix -amine or the prefix amino- (or aminoalkyl-) to the name of the parent compound. Thus three names are permissible for

Complex linear polyamines are best designated by replacement nomenclature. These trivial names are retained: aniline, benzidene, phenetidine, toluidine, and xylidine. The bivalent radical ˆ NH ˆ linked to two identical radicals can be denoted by the prefix imino-, as well as when it forms a bridge between two carbon ring atoms. A trivalent nitrogen atom linked to three identical radicals is denoted by the prefix nitrilo-. Thus ethylenedi- aminetetraacetic acid (an allowed exception) should be named ethylenedinitrilotetraacetic acid. Ammonium Compounds. Salts and hydroxides containing quadricovalent nitrogen are named as a substituted ammonium salt or hydroxide. The names of the substituting radicals precede the word ammonium, and then the name of the anion is added as a separate word. For example, (CH3)4NI is tetramethylammonium iodide. When the compound can be considered as derived from a base whose name does not end in -amine, its quaternary nature is denoted by adding -ium to the name of that base (with elision of -e), substituent groups are cited as prefixes, and the name of the anion is added separately at the end. Examples are C6H5NH3HSO4 [(C6H5NH3)PtCl2 6

Anilinium hydrogen sulfate Dianilinium hexachloroplatinate

The names choline and betaine are retained for unsubstituted compounds. In complex cases, the prefixes amino- and imino- may be changed to ammonio- and iminio- and are followed by the name of the molecule representing the most complex group attached to this nitrogen atom and are preceded by the names of the other radicals attached to this nitrogen. Finally the name of the anion is added separately. For example, the name might be 1-trimethylammonioacridine chloride or 1-acridinyltrimethylammonium chloride. When the preceding rules lead to inconvenient names, then (1) the unaltered name of the base may be used followed by the name of the anion or (2) for salts of hydrohalogen acids only the unaltered name of the base is used followed by the name of the hydrohalide. An example of the latter would be 2-ethyl-p-phenylenediamine monohydrochloride. Azo Compounds. When the azo group ( ˆ N ¨ N ˆ ) connects radicals derived from identical unsubstituted molecules, the name is formed by adding the prefix azo- to the name of the parent unsubstituted molecules. Substituents are denoted by prefixes and suffixes. The azo group has priority for lowest-numbered locant. Examples are azobenzene for C6H5 ˆ N ¨ N ˆ C6H5, azobenzene-4- sulfonic acid for C6H5 ˆ N ¨ N ˆ C6H5SO3H, and 2,4-dichloroazobenzene-4-sulfonic acid for ClC6H4 ˆ N ¨ N ˆ C6H3ClSO3H. When the parent molecules connected by the azo group are different, azo is placed between the complete names of the parent molecules, substituted or unsubstituted. Locants

ORGANIC COMPOUNDS

1.31

are placed between the affix azo and the names of the molecules to which each refers. Preference is given to the more complex parent molecule for citation as the first component, e.g., 2-aminonaphthalene-1-azo-(4-chloro-2-methylbenzene). In an alternative method, the senior component is regarded as substituted by RN ¨ N ˆ , this group R being named as a radical. Thus 2-(7-phenylazo-2-naphthylazo)anthracene is the name by this alternative method for the compound named anthracene-2-azo2-naphthalene-7-azobenzene.

Azoxy Compounds. Where the position of the azoxy oxygen atom is unknown or immaterial, the compound is named in accordance with azo rules, with the affix azo replaced by azoxy. When the position of the azoxy oxygen atom in an unsymmetrical compound is designated, a prefix NNO- or ONN- is used. When both the groups attached to the azoxy radical are cited in the name of the compound, the prefix NNO- specifies that the second of these two groups is attached directly to ˆ N(O) ˆ ; the prefix ONN- specifies that the first of these two groups is attached directly to ˆ N(O) ˆ . When only one parent compound is cited in the name, the prefixed ONN- and NNO- specify that the group carrying the primed and unprimed substituents is connected, respectively, to the ˆ N(O) ˆ group. The prefix NON- signifies that the position of the oxygen atom is unknown; the azoxy group is then written as ˆ N2O ˆ . For example,

1⬘

N

N

1

2⬘

O Cl Cl

2

2,2⬘,4-Trichloro-NNO-azoxybenzene 4

Cl

Boron Compounds. Molecular hydrides of boron are called boranes. They are named by using a multiplying affix to designate the number of boron atoms and adding an Arabic numeral within parentheses as a suffix to denote the number of hydrogen atoms present. Examples are pentaborane(9) for B5H9 and pentaborane(11) for B5H11. Organic ring systems are named by replacement nomenclature. Three- to ten-membered monocyclic ring systems containing uncharged boron atoms may be named by the specialist nomenclature for heterocyclic systems. Organic derivatives are named as outlined for substitutive nomenclature. The complexity of boron nomenclature precludes additional details; the text by Rigaudy and Klesney should be consulted.

Carboxylic Acids. Carboxylic acids may be named in several ways. (1) ˆ COOH groups replacing CH3 ˆ at the end of the main chain of an acyclic hydrocarbon are denoted by adding -oic acid to the name of the hydrocarbon. (2) When the ˆ COOH group is the principal group, the suffix -carboxylic acid can be added to the name of the parent chain whose name and chain numbering does not include the carbon atom of the ˆ COOH group. The former nomenclature is preferred unless use of the ending -carboxylic acid leads to citation of a larger number of carboxyl groups as suffix. (3) Carboxyl groups are designated by the prefix carboxy- when attached to a group named as a substituent or when another group is present that has higher priority for citation as principal group. In all cases, the

1.32

SECTION 1

principal chain should be linked to as many carboxyl groups as possible even though it might not be the longest chain present. Examples are

Removal of the OH from the ˆ COOH group to form the acyl radical results in changing the ending -oic acid to -oyl or the ending -carboxylic acid to -carbonyl. Thus the radical CH3CH2CH2CH2CO ˆ is named either pentanoyl or butanecarbonyl. When the hydroxyl has not been removed from all carboxyl groups present in an acid, the remaining carboxyl groups are denoted by the prefix carboxy-. For example, HOOCCH2CH2CH2CH2CH2CO ˆ is named 6-carboxyhexanoyl. Many trivial names exist for acids: these are listed in Table 1.11. Generally, radicals are formed by replacing -ic acid by -oyl.* When a trivial name is given to an acyclic monoacid or diacid, the numeral 1 is always given as locant to the carbon atom of a carboxyl group in the acid or to the carbon atom with a free valence in the radical RCO ˆ . Ethers (R1 ˆ O ˆ R2). In substitutive nomenclature, one of the possible radicals, R ˆ O ˆ , is stated as the prefix to the parent compound that is senior from among R1 or R2. Examples are methoxyethane for CH3OCH2CH3 and butoxyethanol for C4H9OCH2CH2OH. When another principal group has precedence and oxygen is linking two identical parent compounds, the prefix oxy- may be used, as with 2,2-oxydiethanol for HOCH2CH2OCH2CH2OH. Compounds of the type RO ˆ Y ˆ OR, where the two parent compounds are identical and contain a group having priority over ethers for citation as suffix, are named as assemblies of identical units. For example, HOOC ˆ CH2 ˆ O ˆ CH2CH2 ˆ O ˆ CH2 ˆ COOH is named 2,2-(ethylenedioxy)diacetic acid. Linear polyethers derived from three or more molecules of aliphatic dihydroxy compounds, particularly when the chain length exceeds ten units, are most conveniently named by open-chain replacement nomenclature. For example, CH3CH2 ˆ O ˆ CH2CH2 ˆ O ˆ CH2CH3 could be 3,6-dioxaoctane or (2-ethoxy)ethoxyethane. An oxygen atom directly attached to two carbon atoms already forming part of a ring system or to two carbon atoms of a chain may be indicated by the prefix epoxy-. For example, is named 1-chloro-2,3,-epoxypropane. Symmetrical linear polyethers may be named (1) in terms of the central oxygen atom when there is an odd number of ether oxygen atoms or (2) in terms of the central hydrocarbon group when there is an even number of ether oxygen atoms. For example, C2H5 ˆ O ˆ C4H8 ˆ O ˆ C4H8 ˆ O ˆ C2H5 is bis-(4-ethoxybutyl)ether, and 3,6-dioxaoctane (earlier example) could be named 1,2-bis(ethoxy)ethane. Polyethers and Cyclic Polyethers. During the past several decades, linear and cyclic polyethers have gained considerable prominence. This is largely due to their remarkable ability to complex metallic and organic cations. The linear polyethers of the polyethylene *Exceptions: formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, oxalyl, malonyl, succinyl, glutaryl, furoyl, and thenoyl.

1.33

ORGANIC COMPOUNDS

TABLE 1.11 Names of Some Carboxylic Acids

Systematic name

Trivial name

Methanoic Ethanoic Propanoic Butanoic 2-Methylpropanoic Pentanoic 3-Methylbutanoic 2,2-Dimethylpropanoic Hexanoic Heptanoic Octanoic Decanoic Dodecanoic Tetradecanoic Hexadecanoic Octadecanoic

Formic Acetic Propionic Butyric Isobutyric* Valeric Isovaleric* Pivalic* (Caproic) (Enanthic) (Caprylic) (Capric) Lauric* Myristic* Palmitic* Stearic*

Ethanedioic Propanedioic Butanedioic Pentanedioic Hexanedioic Heptanedioic Octanedioic Nonanedioic Decanedioic Propenoic Propynoic 2-Methylpropenoic trans-2-Butenoic cis-2-Butenoic cis-9-Octadecenoic trans-9-Octadecenoic cis-Butenedioic trans-Butenedioic cis-Methylbutenedioic

Oxalic Malonic Succinic Glutaric Adipic Pimelic* Suberic* Azelaic* Sebacic* Acrylic Propiolic Methacrylic Crotonic Isocrotonic Oleic Elaidic Maleic Fumaric Citraconic*

Systematic name

Trivial name

trans-Methylbutenedioic

Mesaconic*

1,2,2-Trimethyl-1,3cyclopentanedicarboxylic acid Benzenecarboxylic 1,2-Benzenedicarboxylic 1,3-Benzenedicarboxylic 1,4-Benzenedicarboxylic Naphthalenecarboxylic Methylbenzenecarboxylic 2-Phenylpropanoic 2-Phenylpropenoic trans-3-Phenylpropenoic Furancarboxylic Thiophenecarboxylic 3-Pyridinecarboxylic 4-Pyridinecarboxylic

Camphoric

Benzoic Phthalic Isophthalic Terephthalic Naphthoic Toluic Hydratropic Atropic Cinnamic Furoic Thenoic Nicotinic Isonicotinic

Hydroxyethanoic 2-Hydroxypropanoic 2,3-Dihydroxypropanoic Hydroxypropanedioic Hydroxybutanedioic 2,3-Dihydroxybutanedioic 3-Hydroxy-2-phenylpropanoic 2-Hydroxy-2,2diphenylethanoic 2-Hydroxybenzoic Methoxybenzoic 4-Hydroxy-3-methoxybenzoic

Glycolic Lactic Glyceric Tartronic Malic Tartaric Tropic Benzilic

3,4-Dimethoxybenzoic 3,4-Methylenedioxybenzoic 3,4-Dihydroxybenzoic 3,4,5-Trihydroxybenzoic

Veratric Piperonylic Protocatechuic Gallic

Salicylic Anisic Vanillic

The names in parentheses are abandoned but are listed for reference to older literature. * Systematic names should be used in derivatives formed by substitution on a carbon atom.

glycol type are discussed in Section 10. The cyclic polyethers are called crown ethers if they are monocyclic and cryptands if they are di- or multi-cyclic compounds. Crown ethers are typically complicated structures and their names have evolved from the convenient, semi-systematic nomenclature developed by the pioneers in the field. The name “crown” was suggested because the cyclic polyethers “crown a cation” when they complex it. The most general naming system consists in identifying the largest cycle and then denoting the number and type of heteroatoms present. The most common repeating unit is ethyleneoxy or ˆ CH2CH2O ˆ , normally in the form 1,2-ethylenedioxy and this is

1.34

SECTION 1

presumed to be present unless otherwise noted. Ethylene oxide (oxirane) is the smallest cyclic compound containing this unit. Dioxane is formally its dimer. The trimer, called 9crown-3, is known but the smallest compound normally considered to be a crown ether is 12-crown-4. 18-Crown-6 has six repeating ethyleneoxy units and is systematically named 1,4,7,10,13,16-hexaoxacyclooctadecane. Examples of various crown ethers and cryptands are shown here. The top line of compounds may be named readily enough although the problem with this semi-systematic approach is obvious. If two methylenes were added to 18-crown-6, the compound could correctly be called 20-crown-6 but in the absence of unequivocal descriptors, the positions of the 3-carbon bridges would be unclear. The more cumbersome name 1,4,7,11,13,17-hexaoxacycloicosane tells clearly that the longer bridges are adjacent to each other. A similar problem is apparent in the last two entries of the second line. The designations dicyclohexano and dibenzo are clear as to the substituents but not their positions. The semi-systematic nomenclature is widely used, however, because it is so much less cumbersome for most purposes. O

O

O

O

O

O

O

O

O

O

O

O

O

O O

O O

O

dioxane

O

O

O

12-crown-4

O PhH2C-N

N-H O

O

N

OO

O

N

O O

O N

O

[1.1.1] cryptand

O

O O

O

[2.2.1] cryptand

O

24-crown-8

O

O

N,N'-dibenzyl-4,13diaza-18-crown-6

N

O O

18-crown-6

N-CH2Ph O

4,13-diaza-18-crown-6

O

15-crown-5

O

H-N

O

O

O

O

O

O

O O

O

O

dicyclohexano-18-crown-6

dibenzo-18-crown-6

O O

N

O O N

O

O

O

O

O O

N

N O

O

[2.2.2] cryptand benzo-[2.2.2] cryptand

S O

S O

O

O

N

N

dithia-[2.2.2] cryptand

An additional nuance in the nomenclature of these compounds concerns their complexes. The open-chained compounds are often referred to as podands and their complexes as podates. The cyclic ethers may also be called coronands and their complexes are therefore coronates. Complexed cryptands are cryptates. The even more complicated structures known as spherands, cavitands, or carcerands are called spherates, cavitates, or carcerates, respectively, when complexed. The combination of a macrocycle (crown ether or coronand) and a sidechain (podand) is typically called a lariat ether. An alternate nomenclature system based upon IUPAC principles polymer systems has also been developed but it has not been adopted broadly. Using this method, 15-crown-5 would be called cyclo[pentakis(oxyethylene)] instead of 1,4,7,10,13-pentaoxacyclopentadecane. In this case, substituents and other heteroatoms make the names more complex. Partial ethers of polyhydroxy compounds may be named (1) by substitutive nomenclature or (2) by stating the name of the polyhydroxy compound followed by the name of the etherifying radical(s) followed by the word ether. For example, CH2O HCOH CH2OH

C4H9

(1) 3-Butoxy-1,2-propanediol (2) Glycerol 1-buty ether; also, 1-O-butylglycerol

ORGANIC COMPOUNDS

1.35

Cyclic ethers are named either as heterocyclic compounds or by specialist rules of heterocyclic nomenclature. Radicofunctional names are formed by citing the names of the radicals R1 and R2 followed by the word ether. Thus methoxyethane becomes ethyl methyl ether and ethoxyethane becomes diethyl ether. Halogen Derivatives. Using substitutive nomenclature, names are formed by adding prefixes listed in Table 1.8 to the name of the parent compound. The prefix perhalo- implies the replacement of all hydrogen atoms by the particular halogen atoms. Cations of the type R1R2X are given names derived from the halonium ion, H2X, by substitution, e.g., diethyliodonium chloride for (C2H5)2ICl. These trivial names are retained: bromoform (CHBr3), chloroform (CHCl3), fluoroform (CHF3), iodoform (CHI3), phosgene (COCl2), thiophosgene (CSCl2), and dichlorocarbene radical (aCCl2). Inorganic nomenclature leads to such names as carbonyl and thiocarbonyl halides (COX2 and CSX2) and carbon tetrahalides (CX4). Hydroxylamines and Oximes. For RNH ˆ OH compounds, prefix the name of the radical R to hydroxylamine. If another substituent has priority as principal group, attach the prefix hydroxyamino- to the parent name. For example, C6H5NHOH would be named Nphenylhydroxylamine, but HOC6H4NHOH would be (hydroxyamino)phenol, with the point of attachment indicated by a locant preceding the parentheses. Compounds of the type R1NH ˆ OR2 are named (1) as alkoxyamino derivatives of compound R1H, (2) as N,O-substituted hydroxylamines, (3) as alkoxyamines (even if R1 is hydrogen), or (4) by the prefix aminooxy- when another substituent has priority for parent name. Examples of each type are as follows: 1. 2-(Methoxyamino)-8-naphthalenecarboxylic acid for CH3ONH ˆ C10H6COOH 2. O-phenylhydroxylamine for H2N ˆ O ˆ C6H5 or N-phenylhydroxylamine for C6H5NH ˆ OH 3. Phenoxyamine for H2N ˆ O ˆ C6H5 (not preferred to O-phenylhydroxylamine) 4. Ethyl (aminooxy)acetate for H2N ˆ O ˆ CH2CO ˆ OC2H5 Acyl derivatives, RCO ˆ NH ˆ OH and H2N ˆ O ˆ CO ˆ R, are named as N-hydroxy derivatives of amides and as O-acylhydroxylamines, respectively. The former may also be named as hydroxamic acids. Examples are N-hydroxyacetamide for CH3CO ˆ NH ˆ OH and O-acetylhydroxylamine for H2N ˆ O ˆ CO ˆ CH3. Further substituents are denoted by prefixes with O- and/or N-locants. For example, C6H5NH ˆ O ˆ C2H5 would be O-ethyl-N-phenylhydroxylamine or N-ethoxylaniline. For oximes, the word oxime is placed after the name of the aldehyde or ketone. If the carbonyl group is not the principal group, use the prefix hydroxyimino-. Compounds with the group aN ˆ OR are named by a prefix alkyloxyimino- as oxime O-ethers or as O-substituted oximes. Compounds with the group aC  N(O)R are named by adding Noxide after the name of the alkylideneamine compound. For amine oxides, add the word oxide after the name of the base, with locants. For example, C5H5N ˆ O is named pyridine N-oxide or pyridine 1-oxide. Imines. The group aC ¨ NH is named either by the suffix -imine or by citing the name of the bivalent radical R1R2Cb as a prefix to amine. For example, CH3CH2CH2CH ¨ NH

1.36

SECTION 1

could be named 1-butanimine or butylideneamine. When the nitrogen is substituted, as in CH2 ¨ N ˆ CH2CH3, the name is N-(methylidene) ethylamine. Quinones are exceptions. When one or more atoms of quinonoid oxygen have been replaced by aNH or aNR, they are named by using the name of the quinone followed by the word imine (and preceded by proper affixes). Substituents on the nitrogen atom are named as prefixes. Examples are

Ketenes. Derivatives of the compound ketene, CH2 ¨ C ¨ O, are named by substitutive nomenclature. For example, C4H9CH ¨ C ¨ O is butyl ketene. An acyl derivative, such as CH3CH2 ˆ CO ˆ CH2CH ¨ C ¨ O, may be named as a polyketone, 1-hexene-1,4-dione. Bis-ketene is used for two to avoid ambiguity with diketene (dimeric ketene).

Ketones. Acyclic ketones are named (1) by adding the suffix -one to the name of the hydrocarbon forming the principal chain or (2) by citing the names of the radicals R1 and R2 followed by the word ketone. In addition to the preceding nomenclature, acyclic monoacyl derivatives of cyclic compounds may be named (3) by prefixing the name of the acyl group to the name of the cyclic compound. For example,

When the cyclic component is benzene or naphthalene, the -ic acid or -oic acid of the acid corresponding to the acyl group is changed to -ophenone or -onaphthone, respectively. For example, C6H5 ˆ CO ˆ CH2CH2CH3 can be named either butyrophenone (or butanophenone) or phenyl propyl ketone. Radicofunctional nomenclature can be used when a carbonyl group is attached directly to carbon atoms in two ring systems and no other substituent is present having priority for citation. When the methylene group in polycarbocyclic and heterocyclic ketones is replaced by a keto group, the change may be denoted by attaching the suffix -one to the name of the ring system. However, when cCH in an unsaturated or aromatic system is replaced by a keto group, two alternative names become possible. (1) The maximum number of noncumulative double bonds is added after introduction of the carbonyl group(s), and any hydrogen that remains to be added is denoted as indicated hydrogen with the carbonyl group having priority over the indicated hydrogen for lower-numbered locant. (2) The prefix oxois used, with the hydrogenation indicated by hydro prefixes; hydrogenation is considered

ORGANIC COMPOUNDS

1.37

to have occurred before the introduction of the carbonyl group. For example,

When another group having higher priority for citation as principal group is also present, the ketonic oxygen may be expressed by the prefix oxo-, or one can use the name of the carbonyl-containing radical, as, for example, acyl radicals and oxo-substituted radicals. Examples are

Diketones and tetraketones derived from aromatic compounds by conversion of two or four cCH groups into keto groups, with any necessary rearrangement of double bonds to a quinonoid structure, are named by adding the suffix -quinone and any necessary affixes. Polyketones in which two or more contiguous carbonyl groups have rings attached at each end may be named (1) by the radicofunctional method or (2) by substitutive nomenclature. For example,

Some trivial names are retained: acetone (2-propanone), biacetyl (2,3-butanedione), propiophenone (C6H5 ˆ CO ˆ CH2CH3), chalcone (C6H5 ˆ CH ¨ CH ˆ CO ˆ C6H5), and deoxybenzoin (C6H5 ˆ CH2 ˆ CO ˆ C6H5). These contracted names of heterocyclic nitrogen compounds are retained as alternatives for systematic names, sometimes with indicated hydrogen. In addition, names of oxo derivatives of fully saturated nitrogen heterocycles that systematically end in -idinone are often contracted to end in -idone when no ambiguity might result. For example,

1.38

SECTION 1

Lactones, Lactides, Lactams, and Lactims. When the hydroxy acid from which water may be considered to have been eliminated has a trivial name, the lactone is designated by substituting -olactone for -ic acid. Locants for a carbonyl group are numbered as low as possible, even before that of a hydroxyl group. Lactones formed from aliphatic acids are named by adding -olide to the name of the nonhydroxylated hydrocarbon with the same number of carbon atoms. The suffix -olide signifies the change of aCH · · · CH3 into aC· · ·C¨ O QOR Structures in which one or more (but not all) rings of an aggregate are lactone rings are named by placing -carbolactone (denoting the ˆ O ˆ CO ˆ bridge) after the names of the structures that remain when each bridge is replaced by two hydrogen atoms. The locant for ˆ CO ˆ is cited before that for the ester oxygen atom. An additional carbon atom is incorporated into this structure as compared to the -olide. These trivial names are permitted: -butyrolactone, -valerolactone, and -valerolactone. Names based on heterocycles may be used for all lactones. Thus, -butyrolactone is also tetrahydro-2-furanone or dihydro-2(3H)-furanone. Lactides, intermolecular cyclic esters, are named as heterocycles. Lactams and lactims, containing a ˆ CO ˆ NH ˆ and ˆ C(OH) ¨ N ˆ group, respectively, are named as heterocycles, but they may also be named with -lactam or -lactim in place of -olide. For example,

Nitriles and Related Compounds. For acids whose systematic names end in -carboxylic acid, nitriles are named by adding the suffix -carbonitrile when the ˆ CN group replaces the ˆ COOH group. The carbon atom of the ˆ CN group is excluded from the numbering of a chain to which it is attached. However, when the triple-bonded nitrogen atom is considered to replace three hydrogen atoms at the end of the main chain of an acyclic hydrocarbon, the suffix -nitrile is added to the name of the hydrocarbon. Numbering begins with the carbon attached to the nitrogen. For example, CH3CH2CH2CH2CH2CN is named (1) pentanecarbonitrile or (2) hexanenitrile.

1.39

ORGANIC COMPOUNDS

Trivial acid names are formed by changing the endings -oic acid or -ic acid to -onitrile. For example, CH3CN is acetonitrile. When the ˆ CN group is not the highest priority group, the ˆ CN group is denoted by the prefix cyano-. In order of decreasing priority for citation of a functional class name, and the prefix for substitutive nomenclature, are the following related compounds: Functional group ˆ NC ˆ OCN ˆ NCO ˆ ONC ˆ SCN ˆ NCS ˆ SeCN ˆ NCSe

Prefix IsocyanoCyanatoIsocyanato— ThiocyanatoIsothiocyanatoSelenocyanatoIsoselenocyanato-

Radicofunctional ending Isocyanide Cyanate Isocyanate Fulminate Thiocyanate Isothiocyanate Selenocyanate Isoselenocyanate

Peroxides. Compounds of the type R ˆ O ˆ OH are named (1) by placing the name of the radical R before the word hydroperoxide or (2) by use of the prefix hydroperoxy- when another parent name has higher priority. For example, C2H5OOH is ethyl hydroperoxide. Compounds of the type R1O ˆ OR2 are named (1) by placing the names of the radicals in alphabetical order before the word peroxide when the group ˆ O ˆ O ˆ links two chains, two rings, or a ring and a chain, (2) by use of the affix dioxy to denote the bivalent group ˆ O ˆ O ˆ for naming assemblies of identical units or to form part of a prefix, or (3) by use of the prefix epidioxy- when the peroxide group forms a bridge between two carbon atoms, a ring, or a ring system. Examples are methyl propyl peroxide for CH3 ˆ O ˆ O ˆ C3H7 and 2,2- dioxydiacetic acid for HOOC ˆ CH2 ˆ O ˆ O ˆ CH2 ˆ COOH. Phosphorus Compounds. Acyclic phosphorus compounds containing only one phosphorus atom, as well as compounds in which only a single phosphorus atom is in each of several functional groups, are named as derivatives of the parent structures listed in Table 1.12. Often these are purely hypothetical parent structures. When hydrogen attached to phosphorus is replaced by a hydrocarbon group, the derivative is named by substitution nomenclature. When hydrogen of an ˆ OH group is replaced, the derivative is named by radicofunctional nomenclature. For example, C2H5PH2 is ethylphosphine; (C2H5)2PH, diethylphosphine; CH3P(OH)2, dihydroxy-methyl-phosphine or methylphosphonous acid; C2H5 ˆ PO(Cl)(OH), ethylchlorophosphonic acid or ethylphosphonochoridic acid or hydrogen chlorodioxoethylphosphate(V); CH3CH(PH2)COOH, 2-phosphinopropionic acid; HP(CH2COOH)2, phosphinediyldiacetic acid; (CH3)HP(O)OH, methylphosphinic acid or hydrogen hydridomethyldioxophosphate(V); (CH3O)3PO, trimethyl phosphate; and (CH3O)3P, trimethyl phosphite. Salts and Esters of Acids. Neutral salts of acids are named by citing the cation(s) and then the anion, whose ending is changed from -oic to -oate or from -ic to -ate. When different acidic residues are present in one structure, prefixes are formed by changing the anion ending -ate to -ato- or -ide to -ido-. The prefix carboxylato- denotes the ionic group ˆ COO. The phrase: (metal) salt of (the acid) is permissible when the carboxyl groups are not all named as affixes. Acid salts include the word hydrogen (with affixes, if appropriate) inserted between the name of the cation and the name of the anion (or word salt).

1.40

SECTION 1

TABLE 1.12 Parent Structures of Phosphorus-containing Compounds

Formula

Parent name

H3P H5P

Phosphine Phosphorane

H3PO H3PS H3PNH P(OH)3 HP(OH)2 H2POH P(O)(OH)3 HP(O)(OH)2

Phosphine oxide Phosphine sulfide Phosphine imide Phosphorous acid Phosphonous acid Phosphinous acid Phosphoric acid Phosphonic acid

H2P(O)OH

Phosphinic acid

Substitutive prefix H2P ˆ PhosphinoH4P ˆ PhosphoranylH3Pb PhosphoroanediylH2Pd Phosphoranetriyl— — — — — — P(O)d PhosphorylHP(O)b Phosphonoylˆ P(O)OH2 PhosphinoylH2P(O) ˆ PhosphinoylaP(O)OH PhosphinocoPhosphinato-

Radicofunctional ending Phosphide — — — — — — Phosphite Phosphonite Phosphinite Phosphate(V) Phosphonate — Phosphinate — —

Esters are named similarly, with the name of the alkyl or aryl radical replacing the name of the cation. Acid esters of acids and their salts are named as neutral esters, but the components are cited in the order: cation, alkyl or aryl radical, hydrogen, and anion. Locants are added if necessary. For example,

Ester groups in R1 ˆ CO ˆ OR2 compounds are named (1) by the prefix alkoxycarbonylor aryloxycabonyl- for ˆ CO ˆ OR2 when the radical R1 contains a substituent with priority for citation as principal group or (2) by the prefix acyloxy- for R1 ˆ CO ˆ O ˆ when the radical R2 contains a substituent with priority for citation as principal group. Examples are

The trivial name acetoxy is retained for the CH3 ˆ CO ˆ O ˆ group. Compounds of the type R2C(OR2)3 are named as R2 esters of the hypothetical ortho acids. For example, CH3C(OCH3)3 is trimethyl orthoacetate.

ORGANIC COMPOUNDS

1.41

Silicon Compounds. SiH4 is called silane; its acyclic homologs are called disilane, trisilane, and so on, according to the number of silicon atoms present. The chain is numbered from one end to the other so as to give the lowest-numbered locant in radicals to the free valence or to substituents on a chain. The abbreviated form silyl is used for the radical SiH3 ˆ . Numbering and citation of side chains proceed according to the principles set forth for hydrocarbon chains. Cyclic nonaromatic structures are designated by the prefix cyclo-. When a chain or ring system is composed entirely of alternating silicon and oxygen atoms, the parent name siloxane is used with a multiplying affix to denote the number of silicon atoms present. The parent name silazane implies alternating silicon and nitrogen atoms; multiplying affixes denote the number of silicon atoms present. The prefix sila- designates replacement of carbon by silicon in replacement nomenclature. Prefix names for radicals are formed analogously to those for the corresponding carboncontaining compounds. Thus silyl is used for SiH3 ˆ , silyene for ˆ SiH2 ˆ , silylidyne for ˆ SiH. Sulfur Compounds Bivalent Sulfur. The prefix thio-, placed before an affix that denotes the oxygencontaining group or an oxygen atom, implies the replacement of that oxygen by sulfur. Thus the suffix -thiol denotes ˆ SH, -thione denotes ˆ (C) ¨ S and implies the presence of an ¨ S at a nonterminal carbon atom, -thioic acid denotes [(C) ¨ S]OH 7 [(C) ¨ O]SH (that is, the O-substituted acid and the S-substituted acid, respectively), -dithioic acid denotes [ ˆ C(S)]SH, and -thial denotes ˆ (C)HS (or -carbothialdehyde denotes ˆ CHS). When -carboxylic acid has been used for acids, the sulfur analog is named -carbothioic acid or -carbodithioic acid. Prefixes for the groups HS ˆ and RS ˆ are mercapto- and alkylthio-, respectively; this latter name may require parentheses for distinction from the use of thio- for replacement of oxygen in a trivially named acid. Examples of this problem are 4-C2H5 ˆ C6H4 ˆ CSOH named p-ethyl(thio)benzoic acid and 4-C2H5 ˆ S ˆ C6H4 ˆ COOH named p-(ethylthio) benzoic acid. When ˆ SH is not the principal group, the prefix mercapto- is placed before the name of the parent compound to denote an unsubstituted ˆ SH group. The prefix thioxo- is used for naming ¨ S in a thioketone. Sulfur analogs of acetals are named as alkylthio- or arylthio-. For example, CH3CH(SCH3)OCH3 is 1-methoxy-1(methylthio)ethane. Prefix forms for -carbothioic acids are hydroxy(thiocarbonyl)- when referring to the O-substituted acid and mercapto(carbonyl)- for the S-substituted acid. Salts are formed as with oxygen-containing compounds. For example, C2H5 ˆ S ˆ Na is named either sodium ethanethiolate or sodium ethyl sulfide. If mercapto- has been used as a prefix, the salt is named by use of the prefix sulfido- for ˆ S. Compounds of the type R1 ˆ S ˆ R2 are named alkylthio- (or arylthio-) as a prefix to the name of R1 or R2, whichever is the senior. Sulfonium Compounds. Sulfonium compounds of the type R1R2R3SX are named by citing in alphabetical order the radical names followed by -sulfonium and the name of the anion. For heterocyclic compounds, -ium is added to the name of the ring system. Replacement of aCH by sulfonium sulfur is denoted by the prefix thionia-, and the name of the anion is added at the end. Organosulfur Halides. When sulfur is directly linked only to an organic radical and to a halogen atom, the radical name is attached to the word sulfur and the name(s) and number of the halide(s) are stated as a separate word. Alternatively, the name can be formed from R ˆ SOH, a sulfenic acid whose radical prefix is sulfenyl-. For example, CH3CH2 ˆ S ˆ Br would be named either ethylsulfur monobromide or ethanesulfenyl bromide. When another principal group is present, a composite prefix is formed from the number and substitutive name(s) of the halogen atoms in front of the syllable thio. For example, BrS ˆ COOH is (bromothio)formic acid.

1.42

SECTION 1

Sulfoxides. Sulfoxides, R1 ˆ SO ˆ R2, are named by placing the names of the radicals in alphabetical order before the word sulfoxide. Alternatively, the less senior radical is named followed by sulfinyl- and concluded by the name of the senior group. For example, CH3CH2 ˆ SO ˆ CH2CH2CH3 is named either ethyl propyl sulfoxide or 1-(ethylsulfinyl)propane. When an aSO group is incorporated in a ring, the compound is named an oxide. Sulfones. Sulfones, R1 ˆ SO2 ˆ R2, are named in an analogous manner to sulfoxides, using the word sulfone in place of sulfoxide. In prefixes, the less senior radical is followed by -sulfonyl-. When the aSO2 group is incorporated in a ring, the compound is named as a dioxide. Sulfur Acids. Organic oxy acids of sulfur, that is, ˆ SO3H, ˆ SO2H, and ˆ SOH, are named sulfonic acid, sulfinic acid, and sulfenic acid, respectively. In subordinate use, the respective prefixes are sulfo-, sulfino, and sulfeno-. The grouping ˆ SO2 ˆ O ˆ SO2 ˆ or ˆ SO ˆ O ˆ SO is named sulfonic or sulfinic anhydride, respectively. Inorganic nomenclature is employed in naming sulfur acids and their derivatives in which sulfur is linked only through oxygen to the organic radical. For example, (C2H5O)2SO2 is diethyl sulfate and C2H5O ˆ SO2 ˆ OH is ethyl hydrogen sulfate. Prefixes O- and S- are used where necessary to denote attachment to oxygen and to sulfur, respectively, in sulfur replacement compounds. For example, CH3 ˆ S ˆ SO2 ˆ ONa is sodium S-methyl thiosulfate. When sulfur is linked only through nitrogen, or through nitrogen and oxygen, to the organic radical, naming is as follows: (1) N-substituted amides are designated as N-substituted derivatives of the sulfur amides and (2) compounds of the type R ˆ NH ˆ SO3H may be named as N-substituted sulfamic acids or by the prefix sulfoamino- to denote the group HO3S ˆ NH ˆ . The groups ˆ N ¨ SO and ˆ N ¨ SO2 are named sulfinylamines and sulfonylamines, respectively. Sultones and Sultams. Compounds containing the group ˆ SO2ˆO ˆ as part of the ring are called -sultone. The ˆ SO2 ˆ group has priority over the ˆ O ˆ group for lowestnumbered locant. Similarly, the ˆ SO2 ˆ N ¨ group as part of a ring is named by adding -sultam to the name of the hydrocarbon with the same number of carbon atoms. The ˆ SO2 ˆ has priority over ˆ N ¨ for lowest-numbered locant. Steroids. Steroids are important natural products that have a special nomenclature. They typically consist of three fused 6-membered rings and a four fused 5-membered ring. The 12

11 19 1 2 A 3

9 10

8 7

B

18

17 13

C

5

4 H3C H3C

18 19

D 16 3

5

6 H3C H3C H

CH3

H3C

H3C

H

H3C

H H

H

CH3 H3C

H

H3C

Ergosterol OH H

H

Androsterone

H

HO

H3C OH H H

H3C

H

H H

CH3 H3C

H

HO H

H3C O

H

CH3 H

H3C

Cholesterol

Lanosterol

H OH H

H3C H3C

H

HO H

HO H H H3C CH3

H3C

17

9

14 15

H

H

O Estradiol

Testosterone

1.43

ORGANIC COMPOUNDS

rings are designated A, B, C, and D as shown here. The most common, all trans ring fusion is illustrated in the right hand structure. Most steroids that occur naturally possess the two methyl groups (“bridgehead” or angular methyl groups) shown as carbons 18 and 19 at positions 10 and 13, respectively. Cholesterol is the most common steroid of mammalian membranes. It is formed biologically from lanosterol, as shown. Ergosterol is the most common steroid of fungal membranes. It differs from cholesterol by the presence of two additional double bonds that affect its three dimensional structure. Also shown are three so-called steroid hormones, androsterone, estradiol, and testosterone. Note the presence of an aromatic A-ring in estradiol. Vitamins. The vitamins are natural organic compounds of considerable diversity that occur widely. The name derives from the Latin vita (life) and “amin,” a shortened form of amine. The name reflects the historical discovery of these substances, not all of which are amines. They are all of relatively low molecular weight, especially compared to peptides but in a range comparable to steroids. These substances are uniformly active and play various roles in biosynthesis and metabolism. The vitamins are too numerous to detail here but the most common examples are illustrated. They are classed using the common system, that is, water or fat soluble, depending on their approximate level of hydrophobicity or hydrophilicity. Their names are typically nonsystematic but the diversity of their structures requires that the trivial names be used. H3C CH3

Fat-soluble vitamins CH3

H3C CH3

CH3 CH3

CH3 H3C

CH2OH Vitamin A

CH3

Vitamin D CH2 HO

CH3 HO

H CH3

H3C

O CH3

H

O R

CH3

CH3

CH3 O Vitamin K

CH3

CH3

Vitamin E

Water-soluble vitamins O

R OH

HO

N Niacin

H3C

HO

CH2OH O O

CH2OH N Vitamin B6

HO

OH

Vitamin C

OH OH

HO

O

H3C

N

H3C

N

N

N N

CH3 Panthenoic acid

S

O

OH

O

Biotin

NH

Riboflavin

H3C

HO H3C

NH

HO

HO

OH H N

O

HN

O

NH2 S

O

OH

N H O

OH

+N

HN N

N H2N

Thiamine

O

N H

N

O

O NH

HO Folate HO

O

O

1.44

SECTION 1

Biological Nomenclature The names assigned to compounds by organic chemists and biologists sometimes differ. Moreover, biological structures are made up of repeating components and rapidly become large and complex molecules. Thus, special terminology has been developed to assist in describing these compounds. Amino Acids. An amino acid is any organic compound that possesses both amine ( ˆ NH2) and carboxyl ( ˆ COOH) groups within the same organic framework. When both functional groups are attached to the same carbon atom, they are designated -amino acids. These are of special significance in biology as they form the diverse monomer set from which peptides and proteins are built. Aminoacetic acid is the simplest example of an -amino acid. Among the 20 biologically most important amino acids, its structure is unique in two ways. First, it possesses no “sidechain” attached to the methylene carbon. Second, the lack of any substituent (other than hydrogen) means that aminoacetic acid, more commonly called glycine, is achiral. The other 19 “essential” or “common” amino acids possess sidechains attached in a stereochemically identical fashion. The other 19 common -amino acids have side chains attached at the position represented by R. Among these 19, proline is unique because its sidechain is attached at the other end to the amino nitrogen, which is therefore secondary rather than primary. The twenty common -amino acids may be named systematically. For example, when R is methyl, the compound may be called 2-methylaminoacetic acid. It may also correctly be called 2-aminopropanoic acid. By far, however, it is most commonly called alanine.

TABLE 1.13 Common

IUPAC

IUB

ˆpKCOOH

Alanine

Ala

A

2.34

ˆ pKNH3 9.69

pKSide chain —

IpH 6.01

O H 3C OH H NH 2

Arginine

Arg

R

2.17

9.04

12.84

10.76

NH

O N H

H2N

OH H NH

2

Asparagine

Asn

N

2.02

8.60

—

5.41

O H2N

OH O

H NH2

1.45

ORGANIC COMPOUNDS

TABLE 1.13 (continued ) Common

IUPAC

IUB

Aspartic acid

Asp

D

ˆ pKCOOH 1.88

ˆpK NH3 9.60

pKSide chain

IpH

3.65

2.77

O HO OH O

Cystine

Cys

C

1.71

8.18

10.28

H NH2

O

5.02 HS

OH H NH2

Glutamic acid

Glu

E

2.16

9.67

4.32

3.24

O

O

OH

HO H NH2

Glutamine

Gln

Q

2.17

9.13

—

O

O

5.65 H2N

OH H NH

2

Glycine

Gly

G

2.34

9.60

—

O

5.97 H2N

Histidine

His

H

1.82

9.17

6.00

7.59

OH O

H N OH H NH2

N

Isoleucine

Ile

I

2.36

9.68

—

CH3

6.02

O

H3C OH H NH2

Leucine

Leu

L

2.36

9.60

—

O

5.98 H3C

OH CH3 H NH2

Lysine

Lys

K

2.18

9.12

10.53

9.82

O H2N

OH H NH2

Methionine

Met

M

2.28

9.21

—

O

5.74 S H3C

OH H NH2

Phenylalanine

Phe

F

1.83

9.13

—

O

5.84

OH H NH2

Proline

Pro

P

1.99

10.6

—

O

6.30

OH NH H

Serine

Ser

S

2.21

9.15

—

O

5.68 HO

OH H NH 2

1.46

SECTION 1

TABLE 1.13 (continued ) Common

IUPAC

IUB ˆpKCOOH

Threonine

Thr

T

2.71

ˆ pKNH 9.62

 3

pK Side chain

IpH

—

6.16

OH

O

H3C

OH H NH 2

Tryptophan

Trp

W

2.38

9.39

—

5.89

O HN

OH H NH 2

Tyrosine

Tyr

Y

2.20

9.11

10.07

5.66

O OH H NH 2

HO

Valine

Val

V

2.32

9.62

—

5.96

CH3 H3C

O

OH H NH 2

The names and structures of the twenty natural amino acids are given in Table 1.13. The International Union of Pure and Applied Chemistry (IUPAC) uses the three-letter abbreviations shown in the second column of Table 1.13 to describe amino acids. These are widely used in biological circles as well but are inappropriate when long peptide or protein sequences need to be described. For example, when proinsulin is cleaved, it forms the biologically important peptide insulin and another peptide usually called C-peptide. The human peptide consists of a linear chain of 31 amino acids that have the sequence, from amino to carboxyl, H2N-Glu-Ala-Glu-Asp-Leu-Gln-Val-Glu-Gln-Glu-Leu-Gly-Gly-GlyPro-Gly-Ala-Gly-Ser-Leu-Gln-Pro-Leu-Ala-Leu-Glu-Gly-Ser-Leu-Gln-OH. This is readily comprehensible to most chemists because the abbreviations are typically the first three letters of the amino acid. Thus, alanine is Ala and arginine is Arg. Aspartic acid and asparagine cannot both be named Asp so the latter is distinguished as Asn. Biologists often must compare peptides or proteins from different species. If the IUPAC nomenclature was used, the descriptor for this peptide would be about four-fold longer than if the International Union of Biology’s (IUB) single-letter codes are used. Where possible, the first letter of the amino acid’s name is used. As with the three-letter abbreviations, this is not always possible. Alanine is A and aspartic acid is arbitrarily assigned the letter D. Asparagine is called N. Glycine is G so glutamic acid is designated E. Although arbitrary, the name is logical for the homologue of aspartic acid. Glutamine is called Q. Arginine cannot use “A,” which is taken by alanine, but the letter “R” is suggestive and serves as a mnemonic. When the single-letter abbreviations are used, the human C-peptide sequence reduces to EAEDLQVGQVELGGGPGAGSLQPLALEGSLQ, often written in groups of five letters as EAEDL QVGQV ELGGG PGAGS LQPLA LEGSL Q so that the sequence can be more conveniently read and compared with other sequences. Most of three-letter abbreviations are taken from the first three letters of the name of the corresponding amino acid and are pronounced as written (alanine–Ala, cysteine–Cys). The one-letter symbol for the amino acids is usually the first letter of the amino acid’s name and is often used when comparing the amino acids sequences of several similar proteins.

ORGANIC COMPOUNDS

1.47

Note that the single-letter abbreviations permit a fast comparison of the sequences so that their differences and similarities can quickly be discerned. The sequences for C-peptides from humans and from rats are compared below (differences are highlighted):

Ten of the amino acids in each sequence differ. Thus, 21 of the 31 amino acids are identical within the sequence. The sequence homology is said to be (21/31 100 )68%. It would have been much more difficult to make this comparison using the longer three-letter abbreviations. For a protein having 200 or 300 amino acids, the problem becomes correspondingly greater. Despite the greater economy of using single letter amino acid abbreviations, it is the three-letter abbreviations that have become shortened names for the essential amino acids. For example, practicing scientists would identify the sequence GPAGW as “Gly-Pro-AlaGly-Try.” A sequence containing both aspartic acid and asparagine such as GAGE would be referred to in conversation as “Gly-Asp-Gly-Asparagine.” Formally, however, the amino acids contained either in peptides or proteins are named in a fashion related to that used for alkanes. The “-ine” suffix is replaced by “-yl” to give, for GAG, glycyl-alanyl-glycine. Peptide and protein sequences are always written and named from the N-terminus to the C-terminus. The C-terminal amino acid retains its full name.

Stereochemistry Concepts in stereochemistry, that is, chemistry in three-dimensional space, are in the process of rapid expansion. This section will deal with only the main principles. The compounds discussed will be those that have identical molecular formulas but differ in the arrangement of their atoms in space. Stereoisomers is the name applied to these compounds. Stereoisomers can be grouped into three categories: (1) Conformational isomers differ from each other only in the way their atoms are oriented in space, but can be converted into one another by rotation about sigma bonds. (2) Geometric isomers are compounds in which rotation about a double bond is restricted. (3) Configurational isomers differ from one another only in configuration about a chiral center, axis, or plane. In subsequent structural representations, a broken line denotes a bond projecting behind the plane of the paper and a wedge denotes a bond projecting in front of the plane of the paper. A line of normal thickness denotes a bond lying essentially in the plane of the paper. Conformational Isomers. A molecule in a conformation into which its atoms return spontaneously after small displacements is termed a conformer. Different arrangements of atoms that can be converted into one another by rotation about single bonds are called conformational isomers (see Figure 1.3). A pair of conformational isomers can be but do not have to be mirror images of each other. When they are not mirror images, they are called diastereomers.

1.48

SECTION 1

H H

C

H

H C

H

H

H H

C

H

eclipsed

H H

C

H staggered

FIGURE 1.3 Eclipsed (left) and staggered (right) conformations of ethane. The ball and stick model is in the staggered conformation.

Acyclic Compounds. Different conformations of acyclic compounds are best viewed by construction of ball-and-stick molecules or by use of Newman projections. Both types of representations are shown for ethane. Atoms or groups that are attached at opposite ends of a single bond should be viewed along the bond axis. If two atoms or groups attached at opposite ends of the bond appear directly one behind the other, these atoms or groups are described as eclipsed. That portion of the molecule is described as being in the eclipsed conformation. If not eclipsed, the atoms or groups and the conformation may be described as staggered. Newman projections show these conformations clearly. Certain physical properties show that rotation about the single bond is not quite free. For ethane there is an energy barrier of about 3 kcal · mol1 (12 kJ · mol1). The potential energy of the molecule is at a minimum for the staggered conformation, increases with rotation, and reaches a maximum at the eclipsed conformation. The energy required to rotate the atoms or groups about the carbon–carbon bond is called torsional energy. Torsional strain is the cause of the relative instability of the eclipsed conformation or any intermediate skew conformations.

FIGURE 1.4 Conformations of butane. (a) Anti-staggered; (b) eclipsed; (c) gauche-staggered; (d) eclipsed; (e) gauche-staggered; (f ) eclipsed. (Eclipsed conformations are slightly staggered for convenience in drawing; actually they are superimposed.)

ORGANIC COMPOUNDS

1.49

In butane, with a methyl group replacing one hydrogen on each carbon of ethane, there are several different staggered conformations (see Figure 1.4). There is the anti conformation in which the methyl groups are as far apart as they can be (dihedral angle of 180 ). There are two gauche conformations in which the methyl groups are only 60 apart; these are two nonsuperimposable mirror images of each other. The anti conformation is more stable than the gauche by about 0.9 kcal · mol1 (4 kJ · mol1). Both are free of torsional strain. However, in a gauche conformation the methyl groups are closer together than the sum of their van der Waals’ radii. Under these conditions van der Waals’ forces are repulsive and raise the energy of conformation. This strain can affect not only the relative stabilities of various staggered conformations but also the heights of the energy barriers between them. The energy maximum (estimated at 4.8–6.1 kcal · mol1 or 20–25 kJ · mol1) is reached when two methyl groups swing past each other (the eclipsed conformation) rather than past hydrogen atoms. Cyclic Compounds. Although cyclic aliphatic compounds are often drawn as if they were planar geometric figures (a triangle for cyclopropane, a square for cyclobutane, and so on), their structures are not that simple. Cyclopropane does possess the maximum angle strain if one considers the difference between a tetrahedral angle (109.5 ) and the 60 angle of the cyclopropane structure. Nevertheless the cyclopropane structure is thermally quite stable. The highest electron density of the carbon–carbon bonds does not lie along the lines connecting the carbon atoms. Bonding electrons lie principally outside the triangular internuclear lines and result in what are known as bent bonds (see Figure 1.5). Cyclobutane has less angle strain than cyclopropane (only 19.5 ). It is also believed to have some bent-bond character associated with the carbon–carbon bonds. The molecule exists in a nonplanar conformation in order to minimize hydrogen–hydrogen eclipsing strain.

FIGURE 1.5

The bent bonds (“tear drops”) of cyclopropane.

FIGURE 1.6

The conformations of cyclopentane.

1.50

SECTION 1

H

H3C

H3C

H

FIGURE 1.7 The two chair conformations of cyclohexane: a  axial hydrogen atom and e  equatorial hydrogen atom. The middle and bottom panels show methylcyclohexane in the chair form with the methyl group equatorial (middle) and axial (bottom).

Cyclopentane is nonplanar, with a structure that resembles an envelope (see Figure 1.6). Four of the carbon atoms are in one plane, and the fifth is out of that plane. The molecule is in continual motion so that the out-of-plane carbon moves rapidly around the ring. The 12 hydrogen atoms of cyclohexane do not occupy equivalent positions. In the chair conformation six hydrogen atoms are perpendicular to the average plane of the molecule and six are directed outward from the ring, slightly above or below the molecular plane (see Figure 1.7). Bonds which are perpendicular to the molecular plane are known as axial bonds, and those which extend outward from the ring are known as equatorial bonds. The three axial bonds directed upward originate from alternate carbon atoms and are parallel with each other; a similar situation exists for the three axial bonds directed downward. Each equatorial bond is drawn so as to be parallel with the ring carbon–carbon bond once removed from the point of attachment to that equatorial bond. At room temperature, cyclohexane is interconverting rapidly between two chair conformations. As one chair form converts to the other, all the equatorial hydrogen atoms become axial and all the axial hydrogens become equatorial. The interconversion is so rapid that all hydrogen atoms on cyclohexane can be considered equivalent. Interconversion is believed to take place by movement of one side of the chair structure to produce the twist boat, and then movement of the other side of the twist boat to give the other chair form. The chair conformation is the most favored structure for cyclohexane. No angle strain is encountered since all bond angles remain tetrahedral. Torsional strain is minimal because all groups are staggered. In the boat conformation of cyclohexane (Figure 1.8) eclipsing torsional strain is significant, although no angle strain is encountered. Nonbonded interaction between the two hydrogen atoms across the ring from each other (the “flagpole” hydrogens) is unfavorable. The boat conformation is about 6.5 kcal · mol1 (27 kJ · mol1) higher in energy than the chair form at 25 C.

ORGANIC COMPOUNDS

1.51

FIGURE 1.8 The boat conformation of cyclohexane. a  axial hydrogen atom and e  equatorial hydrogen atom.

FIGURE 1.9

FIGURE 1.10

Twist-boat conformation of cyclohexane.

Two isomers of 1,4-dimethylcyclohexane. (a) Trans isomer; (b) cis isomer.

A modified boat conformation of cyclohexane, known as the twist boat (Figure 1.9), or skew boat, has been suggested to minimize torsional and nonbonded interactions. This particular conformation is estimated to be about 1.5 kcal · mol1 (6 kJ mol1) lower in energy than the boat form at room temperature. The medium-size rings (7–12 ring atoms) are relatively free of angle strain and can easily take a variety of spatial arrangements. They are not large enough to avoid all nonbonded interactions between atoms. Disubstituted cyclohexanes can exist as cis–trans isomers as well as axial–equatorial conformers. Two isomers are predicted for 1,4-dimethylcyclohexane (see Figure 1.10). For the trans isomer the diequatorial conformer is the energetically favorable form. Only one cis isomer is observed, since the two conformers of the cis compound are identical. Interconversion takes place between the conformational (equatorial-axial) isomers but not configurational (cis–trans) isomers. The bicyclic compound decahydronaphthalene, or bicyclo[4.4.0]decane, has two fused six-membered rings. It exists in cis and trans forms (see Figure 1.11), as determined by the configurations at the bridgehead carbon atoms. Both cis- and trans-decahydronaphthalene can be constructed with two chair conformations.

1.52

FIGURE 1.11 (b) cis isomer.

SECTION 1

Two isomers of decahydronaphthalene, or bicyclo[4.4.0]decane. (a) Trans isomer;

FIGURE 1.12 Two isomers of 2-butene. (a) Cis isomer, bp 3.8 C, mp 138.9 C, dipole moment 0.33 D; (b) trans isomer, bp 0.88 C, mp 105.6 C, dipole moment 0 D.

Geometrical Isomerism. Rotation about a carbon–carbon double bond is restricted because of interaction between the p orbitals which make up the pi bond. Isomerism due to such restricted rotation about a bond is known as geometric isomerism. Parallel overlap of the p orbitals of each carbon atom of the double bond forms the molecular orbital of the pi bond. The relatively large barrier to rotation about the pi bond is estimated to be nearly 63 kcal · mol1 (263 kJ · mol1). When two different substituents are attached to each carbon atom of the double bond, cis–trans isomers can exist. In the case of cis-2-butene (Figure 1.12a), both methyl groups are on the same side of the double bond. The other isomer has the methyl groups on opposite sides and is designated as trans-2-butene (Figure 1.12b). Their physical properties are quite different. Geometric isomerism can also exist in ring systems; examples were cited in the previous discussion on conformational isomers. For compounds containing only double-bonded atoms, the reference plane contains the double-bonded atoms and is perpendicular to the plane containing these atoms and those directly attached to them. It is customary to draw the formulas so that the reference plane is perpendicular to that of the paper. For cyclic compounds the reference plane is that in which the ring skeleton lies or to which it approximates. Cyclic structures are commonly drawn with the ring atoms in the plane of the paper. Sequence Rules for Geometric Isomers and Chiral Compounds. Although cis and trans designations have been used for many years, this approach becomes useless in complex systems. To eliminate confusion when each carbon of a double bond or a chiral center is

ORGANIC COMPOUNDS

FIGURE 1.13

1.53

Configurations designated by priority groups. (a) Z (cis); (b) E (trans).

connected to different groups, the Cahn, Ingold, and Prelog system for designating configuration about a double bond or a chiral center has been adopted by IUPAC. Groups on each carbon atom of the double bond are assigned a first (1) or second (2) priority. Priority is then compared at one carbon relative to the other. When both first priority groups are on the same side of the double bond, the configuration is designated as Z (from the German zusammen, “together”), which was formerly cis. If the first priority groups are on opposite sides of the double bond, the designation is E (from the German entgegen, “in opposition to”), which was formerly trans. (See Figure 1.13.) When a molecule contains more than one double bond, each E or Z prefix has associated with it the lower-numbered locant of the double bond concerned. Thus (see also the rules that follow) O

O H2N

OH

H H aminoacetic acid or glycine

H2N R

OH H

an α-amino acid

When the sequence rules permit alternatives, preference for lower-numbered locants and for inclusion in the principal chain is allotted as follows in the order stated: Z over E groups and cis over trans cyclic groups. If a choice is still not attained, then the lowernumbered locant for such a preferred group at the first point of difference is the determining factor. For example,

RULE 1. Priority is assigned to atoms on the basis of atomic number. Higher priority is assigned to atoms of higher atomic number. If two atoms are isotopes of the same element, the atom of higher mass number has the higher priority. For example, in 2-butene, the carbon atom of each methyl group receives first priority over the hydrogen atom connected to the same carbon atom. Around the asymmetric carbon atom in chloroiodomethanesulfonic acid, the priority sequence is I, Cl, S, H. In 1-bromo-1deuteroethane, the priority sequence is Cl, C, D, H. RULE 2. When atoms attached directly to a double-bonded carbon have the same priority, the second atoms are considered and so on, if necessary, working outward once again from the double bond or chiral center. For example, in 1-chloro-2-methylbutene, in CH3 the second atoms are H, H, H and in CH2CH3 they are C, H, H. Since carbon has a higher atomic number than hydrogen, the ethyl group has the next highest priority after the chlorine atom.

1.54

SECTION 1

RULE 3. When groups under consideration have double or triple bonds, the multiplebonded atom is replaced conceptually by two or three single bonds to that same kind of

atoms themselves are duplicated, not the atoms or groups attached to them. The duplicated atoms (or phantom atoms) may be considered as carrying atomic number zero. For example, among the groups OH, CHO, CH2OH, and H, the OH group has the highest priority, and the C(O, O, H) of CHO takes priority over the C(O, H, H) of CH2OH. Chirality and Optical Activity. A compound is chiral (the term dissymmetric was formerly used) if it is not superimposable on its mirror image. A chiral compound does not have a plane of symmetry. Each chiral compound possesses one (or more) of three types of chiral element, namely, a chiral center, a chiral axis, or a chiral plane. Chiral Center. The chiral center, which is the chiral element most commonly met, is exemplified by an asymmetric carbon with a tetrahedral arrangement of ligands about the carbon. The ligands comprise four different atoms or groups. One “ligand” may be a lone pair of electrons; another, a phantom atom of atomic number zero. This situation is encountered in sulfoxides or with a nitrogen atom. Lactic acid is an example of a molecule with an asymmetric (chiral) carbon. (See Figure 1.14.) A simpler representation of molecules containing asymmetric carbon atoms is the Fischer projection, which is shown here for the same lactic acid configurations. A Fischer

FIGURE 1.14A

Stereo drawing of the lactic acid molecule.

ORGANIC COMPOUNDS

FIGURE 1.14B

1.55

Fischer projection of the lactic acid molecule.

projection involves drawing a cross and attaching to the four ends the four groups that are attached to the asymmetric carbon atom. The asymmetric carbon atom is understood to be located where the lines cross. The horizontal lines are understood to represent bonds coming toward the viewer out of the plane of the paper. The vertical lines represent bonds going away from the viewer behind the plane of the paper as if the vertical line were the side of a circle. The principal chain is depicted in the vertical direction; the lowestnumbered (locant) chain member is placed at the top position. These formulas may be moved sideways or rotated through 180 in the plane of the paper, but they may not be removed from the plane of the paper (i.e., rotated through 90 ). In the latter orientation it is essential to use thickened lines (for bonds coming toward the viewer) and dashed lines (for bonds receding from the viewer) to avoid confusion. Enantiomers. Two nonsuperimposable structures that are mirror images of each other are known as enantiomers. Enantiomers are related to each other in the same way that a right hand is related to a left hand. Except for the direction in which they rotate the plane of polarized light, enantiomers are identical in all physical properties. Enantiomers have identical chemical properties except in their reactivity toward optically active reagents. Enantiomers rotate the plane of polarized light in opposite directions but with equal magnitude. If the light is rotated in a clockwise direction, the sample is said to be dextrorotatory and is designed as (). When a sample rotates the plane of polarized light in a counterclockwise direction, it is said to be levorotatory and is designed as (). Use of the designations d and l is discouraged. Specific Rotation. Optical rotation is caused by individual molecules of the optically active compound. The amount of rotation depends upon how many molecules the light beam encounters in passing through the tube. When allowances are made for the length of the tube that contains the sample and the sample concentration, it is found that the amount of rotation, as well as its direction, is a characteristic of each individual optically active compound. Specific rotation is the number of degrees of rotation observed if a 1-dm tube is used and the compound being examined is present to the extent of 1 g per 100 mL. The density for a pure liquid replaces the solution concentration.

Specific rotation [] 

observed rotation (degrees) length (dm) (g/100 mL)

The temperature of the measurement is indicated by a superscript and the wavelength of the light employed by a subscript written after the bracket; for example, []20 590 implies that the measurement was made at 20 C using 590 nm radiation. Optically Inactive Chiral Compounds. Although chirality is a necessary prerequisite for optical activity, chiral compounds are not necessarily optically active. With an equal mixture of two enantiomers, no net optical rotation is observed. Such a mixture of enantiomers is said to be racemic and is designated as () and not as dl. Racemic mixtures usually have melting points higher than the melting point of either pure enantiomer.

1.56

SECTION 1

A second type of optically inactive chiral compounds, meso compounds, will be discussed next. Multiple Chiral Centers. The number of stereoisomers increases rapidly with an increase in the number of chiral centers in a molecule. A molecule possessing two chiral atoms should have four optical isomers, that is, four structures consisting of two pairs of enantiomers. However, if a compound has two chiral centers but both centers have the same four substituents attached, the total number of isomers is three rather than four. One isomer of such a compound is not chiral because it is identical with its mirror image; it has an internal mirror plane. This is an example of a diastereomer. The achiral structure is denoted as a meso compound. Diastereomers have different physical and chemical properties from the optically active enantiomers. Recognition of a plane of symmetry is usually the easiest way to detect a meso compound. The stereoisomers of tartaric acid are examples of compounds with multiple chiral centers (see Figure 1.15), and one of its isomers is a meso compound. Stereochemistry is sometimes harder to discern in ring systems than in open-chained compounds. The smallest ring, cyclopropane, has six equivalent hydrogens, each of which may be substituted. When a substituent such as a methyl group replaces a hydrogen, the molecule remains achiral because a mirror plane is present that bisects the substituted carbon (and its substituent) and the opposite bond. One side of the cyclopropane therefore reflects the other. The presence of a substituent makes the other cyclopropane positions nonequivalent. Thus a second methyl group may be added on the same carbon (opposite side of the ring) or on one of the adjacent carbons on either the same or opposite sides of the ring. Figure 1.16 shows some of these possibilities. E-1,2-Dicarboxycyclopropane (a) exists in two distinct forms. They are nonsuperimposable mirror images; Z-1,2Dicarboxycyclopropane (b) has an internal mirror plane and is therefore superimposable on its mirror image. Structure (d) in Figure 1.16 shows a molecular model of this compound. The carboxyl substituents do not appear to reflect each other but recall that they can rotate freely about the single bond. A cyclic compound that has two differently substituted asymmetric carbons will have 22  4 optical isomers. These will consist of pairs of cis and trans enantiomers. When the asymmetric centers have identical substituents, the cis isomer will have an internal reflection plane and is called a meso form. The meso forms of cis-1,2-dicarboxycyclopropane are shown in panels (b) and (d) of Figure 1.16 in a line angle drawing and as a molecular model. Torsional Asymmetry. Rotation about single bonds of most acyclic compounds is relatively free at ordinary temperatures. There are, however, some examples of compounds in which nonbonded interactions between large substituent groups inhibit free rotation about a sigma bond. In some cases these compounds can be separated into pairs of enantiomers.

FIGURE 1.15

Isomers of tartaric acid.

1.57

ORGANIC COMPOUNDS

(c)

(d)

FIGURE 1.16 Isomers of cyclopropane-1,2-dicarboxylic acid. (a) E-1,2-Dicarboxycyclopropane (trans isomers); (b) Z-1,2-Dicarboxycyclopropane isomer. (meso isomer); (c) Molecular models of E- (trans-) 1,2-dimethylcyclopropane shown in the tube representation. Rotation of the right hand structure about a vertical axis through the center of the cyclopropane will superimpose the two methyl groups. The methylene of the rotated structure will be in the back, rather than the front, and not superimposed. (d ) A mirror plane through the methylene and the back carbon– carbon bond is a plane of symmetry. The two carboxyl groups appear not to reflect each other in the model shown but they can rotate freely and will reflect each other on an instantaneous basis.

A chiral axis is present in chiral biaryl derivatives. When bulky groups are located at the ortho positions of each aromatic ring in biphenyl, free rotation about the single bond connecting the two rings is inhibited because of torsional strain associated with twisting rotation about the central single bond. Interconversion of enantiomers is prevented (see Figure 1.17). CH3

H3C

HOOC

COOH

H3C

CH3 HOOC

COOH Mirror plane

FIGURE 1.17

Isomers of biphenyl compounds with bulky groups attached at the ortho positions.

1.58

SECTION 1

For compounds possessing a chiral axis, the structure can be regarded as an elongated tetrahedron to be viewed along the axis. In deciding upon the absolute configuration it does not matter from which end it is viewed; the nearer pair of ligands receives the first two positions in the order of precedence (see Figure 1.18). For the meaning of (S), see the discussion under “Absolute Configuration”. A chiral plane is exemplified by the plane containing the benzene ring and the bromine and oxygen atoms in the chiral compound shown in Figure 1.19. Rotation of the benzene ring around the oxygen-to-ring single bonds is inhibited when x is small (although no critical size can be reasonably established).

FIGURE 1.18

Example of a chiral axis.

FIGURE 1.19

Example of a chiral plane.

Absolute Configuration. The terms absolute stereochemistry and absolute configuration are used to describe the three-dimensional arrangement of substituents around a chiral element. A general system for designating absolute configuration is based upon the priority system and sequence rules. Each group attached to a chiral center is assigned a number, with number one the highest-priority group. For example, the groups attached to the chiral center of 2-butanol (see Figure 1.20) are assigned these priorities: 1 for OH, 2 for CH2CH3, 3 for CH3, and 4 for H. The molecule is then viewed from the side opposite the group of lowest priority (the hydrogen atom), and the arrangement of the remaining groups are noted. If, in proceeding from the group of highest priority to the group of second priority and

FIGURE 1.20 Viewing angle as a means of designating the absolute configuration of compounds with a chiral axis. (a) (R)-2-butanol (sequence clockwise); (b) (S)-2-butanol (sequence counterclockwise).

1.59

ORGANIC COMPOUNDS

thence to the third, the eye travels in a clockwise direction, the configuration is specified R (from the Latin rectus, “right”); if the eye travels in a counterclockwise direction, the configuration is specified S (from the Latin sinister, “left”). The complete name includes both configuration and direction of optical rotation, as for example, (S)-()-2-butanol. The relative configurations around the chiral centers of many compounds have been established. One optically active compound is converted to another by a sequence of chemical reactions which are stereospecific; that is, each reaction is known to proceed spatially in a specific way. The configuration of one chiral compound can then be related to the configuration of the next in sequence. In order to establish absolute configuration, one must carry out sufficient stereospecific reactions to relate a new compound to another of known absolute configuration. Historically the configuration of D-()-2,3-dihydroxypropanal has served as the standard to which all configuration has been compared. The absolute configuration assigned to this compound has been confirmed by an X-ray crystallographic technique. Stereochemistry in Biological Systems. Amino acids occur naturally in both D and L (R and S) enantiomeric configurations. Amino acids that occur in proteins almost always have the L configuration although amino acids that occur in bacterial peptides may have the enantiomeric D configuration. The two configurations are shown in Figure 1.21 for alanine. The description of -amino acids as D or L is a holdover from an older nomenclature system. In this system (S)-alanine is called L-alanine. The enantiomer would be D- or (R)-serine. The L (laevo, turned to the left; D dextro, turned to the right) designation refers to the -carbon in the essential amino acids. In alanine, there is a single -carbon that is asymmetric. When two asymmetric centers are present as in L-threonine, the stereochemistry of both carbons must be considered. The common form of L-threonine is the 2S,3R stereoisomer. Threonine (center) is shown in Figure 1.22 along with the simplest chiral amino acid, alanine. The only cyclic amino acid, proline, is pictured as well in the common L-configuration. Extended Arrangements of Peptides and Proteins. Amino acids are linked from the carboxyl to the amine with formation of an amide bond, often referred to as the peptide link. The repeating ( ˆ N ˆ C ˆ CO ˆ ) unit is called the peptide or protein backbone. Peptides and proteins differ only in the number of amino acids present in the biopolymer chain. The cutoff is arbitrarily set. Often, but not always, a peptide is designated as having fewer than 100 amino acids and the protein possesses more. Backbone amide groups have been found to play a role in enzyme catalysis.

H

H

O

N

C

R OH

N H2

C H

R H

H CO O H

CO O H R

NH2 L-amino acid (S configuration)

FIGURE 1.21

H

H

O

N

C

OH

H R D-amino acid (R configuration)

Stereochemistry of -amino acids. The most common, L configuration is shown at the left.

H

H

O

H

O

N

C

N

C

OH

H 3C H

H H

HO L-alanine (S configuration)

FIGURE 1.22

OH

H

H

O

N

C

OH

H

CH3

L-threonine (2S,3R configuration)

L-proline (S configuration)

Structures of alanine, threonine, and proline.

1.60

SECTION 1

The extended chains, that is, the backbones, may further organize into assemblies that have characteristic properties. The two most important of these are the - helix and the -sheet. The latter is illustrated in Figure 1.23. Panel (a) shows the extensive hydrogen bond organization of peptide chains that are oriented in opposite directions. The arrows indicate the nitrogen to carbonyl (arrowhead) direction. The lower panel (b) shows an alternate Hbond organization when the two peptide chains are parallel rather than antiparallel. R N

CH

H R C

CH

O

C

H

N

O

O N

H C

N

R

C

R

H CH

O CH

H

CH

H

R C

R N

O

N

C

H

N

O

O

CH

C

N

R

C

R

H CH

O CH

H

R C

CH

O

R CH

N

O

N

CH

O

O N

H C

R

H

C

CH

H

N

R

C

O

CH

H

R CH

C

R N

C

H

N

O

O N

H C

O CH

C

R

H CH

N

R

(a)

H N

O CH

C

R R N H

CH

H C O

N

R N H

O CH R

C

H

CH

C O

R N

N

CH

H

O CH R

H C

C

N

O

R N H

O CH

CH

C

R

H C

CH

O R

N

O

N

CH

H

R H

C

C

R N

CH

H

CH

O

C

R

R N

N

O

O

N

H C

O CH R

H

CH

H

C O

C

N

R N H

CH

C O

O CH

C

R

(b)

FIGURE 1.23 Hydrogen bonded interactions of peptide chains to form -sheets. The chains are arranged antiparallel in panel (a) and parallel in panel (b).

An alternate organization for peptide chains is the -helix. It is essentially a coil in which a carbonyl group H-bonds an amide nitrogen between every fourth residue. The resulting structure exhibits one full turn for each 3.6 amino acids, which spans 5.4 Å per turn. The resulting -helix is a tight coil that lacks any significant interior space. A schematic representation of the H-bonded coil is shown in Figure 1.24. C

C O C

C H

H

N

C

C

O

H N

C

C O H N

O H

N C O

C

N

H

C

O N

H C

N

C

O

C

FIGURE 1.24

A number of other arrangements are possible for peptide or protein chains. A discussion of them is beyond the scope of this Handbook. Chemical Abstracts Indexing System When compounds of complex structure are considered, the number of name possibilities grows rapidly. To avoid having index entries for all possible names, Chemical Abstracts Service has developed what might be called the principle of inversion. The indexing system employs inverted entries to bring together related compounds in an alphabetically arranged index. The index heading parent from the Chemical Substance Index appears in the Formula Index in lightface before the “comma of inversion.” The substituents follow the “comma of

1.61

ORGANIC COMPOUNDS

inversion” in alphabetical order. Any name modification appears on a separate line. If necessary, the chemical description is completed by citation of an associated ion, a functional derivative, a “salt with” or “compound with” terms and/or a stereochemical descriptor. Quite naturally there is a certain amount of arbitrariness in this system, although the IUPAC nomenclature is followed. The preferred Chemical Abstracts index names for chemical substances have been, with very few exceptions, continued unchanged (since 1972) as set forth in the Ninth Collective Index Guide and in a journal article.* Any revisions appear in the updated Index Guide; new editions appear at 18-month intervals. Appendix VI is of particular interest to chemists. Reprints of the Appendix may be purchased from Chemical Abstracts Service, Marketing Division, P.O. Box 3012, Columbus, Ohio 43210.

PHYSICAL PROPERTIES OF PURE SUBSTANCES TABLE 1.14 Empirical Formula Index for Organic Compounds The alphanumeric designations are keyed to Table 1.15

Cl2H2Si: d226 Cl3HSi: t247 Cl6OSi2: h28 C1 CBrClF2: b255 CBrCl3: b358 CBrF3: b360 CBr2F2: d75 CClF3: c253 CClNO3S: c240 CCl2F2: d170 CCl3D: c127 CCl3F: t232 CCl3NO2: t239 CCl4O2S: t236 CCl4S: t235 CD4O: m36 CHBrCl2: b266 CHBr2Cl: d71 CHBr3: t206 CHClF2: c85 CHCl2F: d183 CHCl3: c126 CHF3: t295 CHF3O3S: t296 CHI3: i36 CHN3O6: t385 CH2BrCl: b256 CH2Br2: d88

CH2Cl2: d190 CH2Cl4Si: c165 CH2I2: d404 CH2N2: c285, d47 CH2N4: t136 CH2O: f27 (CH2O)x: p1 CH2O2: f32 CH2S3: t434 CH3Br: b300 CH3Br3Ge: m254 CH3Cl: c137 CH3ClHg: m295 CH3ClO2S: m32 CH3Cl3Ge: m437 CH3Cl3Si: t238 CH3DO: m35 CH3F: f18 CH3I: i40 CH3NO: f28 CH3NO2: m314, n56 CH3NO3: m313 CH3N5: a289 CH4: m29 CH4Cl2Si: d199, m222 CH4N2O: f34, u12 CH4N2O2S: f30 CH4N2S: t163 CH4N4O2: n54 CH4O: m34 CH4O2: m275 CH4O3S: m30

* J. Chem. Doc., 14(1): 3–15 (1974).

CH4S: m33 CH5AsO3: m125 CH5N: m115 CH5NO3S: a205 CH5N3: g29 CH5N3O: s3 CH5N3S: t162 CH6N2: m270 CH6N4: a180, a181 CH6N4O: c11 CN4O8: t126a C2 C2Br2ClF3: d72 C2Br2Cl4: d99 C2Br2F4: d100 C2Br2O2: o50 C2ClF3: c252 C2Cl2F3I: d188 C2Cl2F4: d227 C2Cl2O2: o51 C2Cl3F3: t251 C2Cl3N: t217 C2Cl4: t29 C2Cl4F2: d347, d348, t26 C2Cl4O: t218 C2Cl6: h29 C2D3N: a30 C2D4O2: a21 C2D6OS: d615

1.62

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to table 1.15

C2F4: t63 C2F6: h44 C2F6O5S2: t297 C2HBrClF3: b258 C2HBr2F3: d103 C2HBr2N: d63 C2HBr3: t205 C2HBr3O: t201 C2HBr3O2: t202 C2HClF2O2: c83 C2HCl2F3: d232 C2HCl3: t230 C2HCl3O: d141 C2HCl3O2: t216 C2HCl5: p9 C2HF3O2: t287 C2H2: a41 C2H2BrClO: b224 C2H2Br2: d80, d81 C2H2Br2F2: d74 C2H2Br2O: b223 C2H2Br2O2: d62 C2H2Br4: t9 C2H2ClF3: c251 C2H2ClN: c27 C2H2Cl2: d178, d179, d180 C2H2Cl2O: c31 C2H2Cl2O2: d138 C2H2Cl4: t27, t28 C2H2F3NO: t286 C2H2O: k1 C2H2O2: g27 C2H2O3: g28 C2H2O4: o48, o49 C2H3Br: b284 C2H3BrO: a35 C2H3BrO2: b220 C2H3Br2Cl3Si: d82 C2H3Br3O: t204 C2H3Cl: c109 C2H3ClF2: c84 C2H3ClO: a37 C2H3ClO2: c24, m187 C2H3Cl3: t226, t227 C2H3Cl3O: t228 C2H3Cl3Si: t252

C2H3Cl5Si: d182 C2H3DO2: a20 C2H3FO: a43 C2H3FO2: f6 C2H3F3: t291 C2H3F3O: t292 C2H3IO: a48 C2H3IO2: i25 C2H3N: a29 C2H3NO: m287 C2H3NS: m289, m426 C2H3N3: t199 C2H3N3S2: a290 C2H4BrCl: b254 C2H4BrNO: b218 C2H4Br2: d77, d78 C2H4ClNO: c22 C2H4Cl2: d176, d177 C2H4Cl2O: d197 C2H4Cl6Si2: b204 C2H4FNO: f5 C2H4F2: d346 C2H4INO: i24 C2H4I2: d403 C2H4N2: a106 C2H4N2O2: o54 C2H4N2O4: d632 C2H4N2O6: e126 C2H4N2S2: d710 C2H4N4: a295, d235 C2H4N4O2: a324 C2H4O: a4, e129 C2H4OS: t142 C2H4O2: a19, h86, m250 C2H4O2S: m14 C2H4O3: h87, p59 C2H4O5S: s23 C2H4S: e130 C2H5AlCl2: e57 C2H5Br: b277 C2H5BrNaO2S: b278 C2H5BrO: b279, b308 C2H5Cl: c102 C2H5ClHg: e165 C2H5ClO: c103, c155 C2H5ClO2S: e19

C2H5ClS: c156 C2H5Cl2OPS: e117 C2H5Cl2O2P: e116 C2H5Cl3Si: c153, t231 C2H5DO: e22 C2H5F: f17 C2H5FO3S: e134 C2H5I: i34 C2H5IO: i35 C2H5N: e131 C2H5NO: a5, a6, m248 C2H5NO2: e186, g25, m181, n53 C2H5NO3: e185 C2H5NS: t141 C2H5N3O2: b215, o53 C2H6: e14 C2H6BrN: b281 C2H6Cd: d501 C2H6ClN: c106 C2H6ClNO2S: d609 C2H6ClO2PS: d504 C2H6Cl2Si: d174 C2H6Hg: d546 C2H6N2: a7 C2H6N2O: a25, m444, n79 C2H6N2O2: m271 C2H6N2O4S: a107 C2H6N2S: m431 C2H6N4O2: o52 C2H6O: d518, e21 C2H6OS: d614, m18 C2H6O2: e16, e128 C2H6O2S: d613 C2H6O3S: d612, m297 C2H6O4S: d610, h114 C2H6O5S2: m31 C2H6S: d611, e20 C2H6S2: d516, e18 C2H6Te: d617 C2H6Zn: d624 C2H7AsO2: d484 C2H7ClSi: c92 C2H7N: d461, e58 C2H7NO: a163, a164 C2H7NO3S: a161

1.63

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C2H7NO4S: a169 C2H7NS: a162 C2H7N5: b133 C2H7O3P: d541 C2H8N2: d539, d540, e15 C2H8N2O: h120 C3 C3Br2F6: d85 C3Cl3NO2: t219 C3Cl3N3: t250 C3Cl3N3O3: t234 C3Cl6: h31 C3Cl6O: h23 C3D6O: a27 C3HCl5O: p7 C3H2ClN: c32 C3H2Cl2O2: m6 C3H2Cl4: t33 C3H2Cl4O: t21 C3H2Cl4O2: t229 C3H2F6O: h45 C3H2N2: m5 C3H2N2O3: i6 C3H2O2: p241 C3H3Br: b344 C3H3Cl: c232 C3H3ClO: a65 C3H3Cl3O: e13 C3H3N: a64 C3H3NOS2: r3 C3H3NO2: c287 C3H3NS: t140 C3H3N3O2S: a249 C3H3N3O3: c299 C3H4: a78, p240 C3H4BrClO: b340, b341 C3H4BrN: b339 C3H4Br2: d95 C3H4Br2O2: d96 C3H4ClN: c220 C3H4Cl2: d221, d222 C3H4Cl2O: c221, c222, d139

C3H4Cl2O2: m219 C3H4Cl3NO: m436 C3H4F4O: t64 C3H4N2: i4, p245 C3H4N2O: c286 C3H4N2OS: t152 C3H4N2O2: h84 C3H4N2S: a291 C3H4O: p204, p242 C3H4O2: a63, o59, p210 C3H4O3: e124, o60 C3H4O4: m3 C3H5Br: a85, b225, b335, b336 C3H5BrO: b276 C3H5BrO2: b337, b338, m143 C3H5Br3: t208 C3H5Cl: c216 C3H5ClO: c101, c215, p216 C3H5ClOS: e101 C3H5ClO2: c218, c219, e98, m182 C3H5Cl3: t244 C3H5Cl3O: t245 C3H5Cl3Si: a102 C3H5FO: f7 C3H5F3O3S: m438 C3H5I: a92, i50 C3H5N: p215 C3H5NO: a62, c290, h168, h169 C3H5NO2: o55 C3H5NS: e161, m421 C3H5N3O: c288 C3H5N3O9: g21 C3H5N3S: c292 C3H6: c364, p205 C3H6BrCl: b257 C3H6BrNO4: b316 C3H6Br2: d92, d93 C3H6Br2O: d94 C3H6ClNO: d502 C3H6Cl2: d218, d219 C3H6Cl2O: d220 C3H6Cl2Si: d200

C3H6Cl4Si: c229 C3H6I2: d405 C3H6N2: a274, d505 C3H6N2O: i7 C3H6N2O2: m4, m269 C3H6N2S: a292, i5 C3H6N2OS: a58 C3H6N6: t198 C3H6O: a26, a81, e10, m446, p211, p227, t345 C3H6OS: m420, t161 C3H6O2: d647, e11, e135, h89, m111, p213 C3H6O2S: m21, m293 C3H6O3: d397, d398, d503, L1, L2, m38, m259, t388 C3H6O3S: p198 C3H6S: p206, p228, t345a C3H6S3: t431 C3H7Br: b332, b333 C3H7BrO: b334 C3H7Cl: c210, c211 C3H7ClO: c111, c152, c213, c214 C3H7ClOS: c136 C3H7ClO2: c212 C3H7ClO2S: p197 C3H7Cl2OP: p236 C3H7Cl3Si: d194, p237 C3H7I: i48, i49 C3H7N: a82, p226 C3H7NO: a28, d522, m110, p212 C3H7NO2: a73, a74, a75, a76, e91, m258, n73, n74 C3H7NO2S: c370 C3H7NO3: i105, n75, p233, s4 C3H7NO5S: a288 C3H7NS: d620 C3H7NS2: d517 C3H7O5P: c17 C3H8: p191 C3H8ClN: c224 C3H8Cl2Si: c75, c150

1.64

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C3H8IN: d549 C3H8N2O: d623, e230 C3H8N2O2: e92, f29 C3H8N2S: d621 C3H8O: e171, p202, p203 C3H8OS2: d425, m305 C3H8O2: d441, m65, p194, p195 C3H8O2S: m20 C3H8O3: g16 C3H8S: e182, p199, p200 C3H8S2: p196 C3H9Al: t327 C3H8BO3: t319 C3H9B3O6: t320 C3H9BrGe: b363 C3H9BrSi: b364 C3H9ClGe: c254 C3H9ClSi: c255 C3H9IOS: t378 C3H9IS: t377 C3H9ISi: i55 C3H9N: i88, m246, p220, t328 C3H9NO: a269, a270, a271, a272, m69, m119, t329 C3H9NO2: a268 C3H9N3Si: a319 C3H9O3P: d551, t364 C3H9O4P: t363 C3H10N2: m247, p192, p193 C3H10N2O: d43 C3H11Br2N3S: a171 C4 C4Cl2F6: d185 C4Cl2F8: d206 C4Cl2O3: d189 C4Cl3F7: h3 C4Cl6: h25 C4D6O3: a23 C4F6O3: t288

C4HBrO3: b299 C4HCl3N2: t246 C4HF7O2: h2 C4H2: b376 C4H2Br2S: d101 C4H2Cl2N2: d223 C4H2Cl2O2: f38 C4H2Cl2O3: d208 C4H2Cl2S: d228 C4H2F6O2: t294 C4H2O3: m2 C4H2O4: a42 C4H3BrS: b353 C4H3ClS: c242 C4H3Cl2N3O: d193 C4H3IS: i52 C4H4: b407 C4H4BrNO2: b351 C4H4Br2O2: d69 C4H4Br2O4: d98 C4H4ClNO2: c239 C4H4Cl2: d168 C4H4Cl2O2: s19 C4H4Cl2O3: c25 C4H4N2: b380, p244, p247, p267, s18 C4H4N2O2: d400, p268 C4H4N2O2S: d388 C4H4N2O3: b1 C4H4N2O5: a79 C4H4N4: d40 C4H4O: f40 C4H4O2: d422 C4H4O3: s16 C4H4O4: f37, ml C4H4S: t154 C4H5BrO4: b350 C4H5Cl: c63, c70 C4H5ClO: c283, c366, m28 C4H5ClO2: a87 C4H5ClO3: e191 C4H5Cl3O2: e226 C4H5F3O2: e227 C4H5N: b400, c365, m27, p269 C4H5NO: m290

C4H5NO2: e106, m193, s17 C4H5NO2S: e32 C4H5NO3: h182 C4H5NS: a93 C4H5N3: a284, i11 C4H5N3O: a198 C4H5N3OS: a191 C4H5N3O2: a154, a155, c289, m322 C4H6: b373, b374, b490, b491 C4H6Br2O2: d70 C4H6ClN: c73 C4H6Cl2: d165, d166, d167 C4H6Cl2O: c74 C4H6Cl2O2: m220 C4H6Cl3NSi: c294 C4H6N2: a151, m280, m281, m282 C4H6N2O2: e114 C4H6N2S: a229 C4H6N4O: d39 C4H6N4O3: a77 C4H6O: b406, c282, d356, d545a, m24, m396 C4H6O2: b386, b401, b402, b403, b492, b497, b498, c367, m26, m114, v2 C4H6O2S: d368 C4H6O3: a22, a24, m334, o56, p225 C4H6O4: d566, s14 C4H6O4S: m23, t148 C4H6O5: h180, h181, o61 C4H6O6: t1, t2 C4H7Br: b240, b241, b242 C4H7BrO2: b244, b280, b307, e75, m146 C4H7Cl: c68, c69, c163, c164 C4H7ClO: b501, c67, c115, i78 C4H7ClO2: c71, c72, e94, m189 C4H7Cl2NSi: c291 C4H7Cl3O: t237

1.65

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C4H7Cl3O2Si: c13 C4H7FO2: e133 C4H7N: b499, i76 C4H7NO: h145, i98, m25, m334, p231, p275 C4H7NO2: m331 C4H7NO3: a46, e192, p12 C4H7NO4: a314, i10 C4H7NS: m419 C4H7N3O: c278 C4H8: b395, b396, b397, c300, m383 C4H8BrCl: b251 C4H8Br2: d67, d68 C4H8Br2O: b149 C4H8Cl2: d162, d163, d164 C4H8Cl2O: b158, d181 C4H8Cl2Si: a89 C4H8N2O: a105, a150 C4H8N2O2: d526, s13 C4H8N2O3: a313, g26 C4H8N2S: a101, t79 C4H8O: b393, b404, b405, b493, e3, e232, i73, m96, m377, m385, t66 C4H8OS: e220, t107, t164 C4H8O2: b398, b399, b495, d646, e51, h106, i75, m389, m390, p229 C4H8O2S: e164, m294, t106 C4H8O3: e23, e150, h116, h127, m64, m291, m298 C4H8O3S: m384 C4H8S: a95, t81 C4H8S2: d707 C4H9Br: b238, b239, b310, b311 C4H9BrO: b285 C4H9Cl: c64, c65, c161, c162 C4H9ClO: c66, c110 C4H9ClO2: c89, c104, m67 C4H9ClSi: c93 C4H9Cl3Si: b483, c225 C4H9Cl3Sn: b481

C4H9F: f20 C4H9I: i30, i31, i43, i44 C4H9Li: b457, b458 C4H9N: p270 C4H9NO: a321, b394, b494, d458, e52, i74, m388, m448 C4H9NO2: a138, a139, a222, b464, b465, h115, i71, n50 C4H9NO2S: a204 C4H9NO3: a187, a188, a189, a190, i70, n51 C4H9NSi: c298 C4H9N3O2: c277 C4H10: b378, m375 C4H10ClN: d467 C4H10ClO2PS: d292 C4H10ClO3P: d291 C4H10Cl2Si: b160, m392 C4H10N2: p179 C4H10N2O: a231 C4H10N2O4S: a8 C4H10O: b391, b392, d300, m381, m382, m393 C4H10OS: e153 C4H10OS2: b186 C4H10O2: b381, b382, b383, b384, b385, b453, d438, d439, e34, m95 C4H10O2S: m430, t149 C4H10O2S2: d424, h118 C4H10O3: b181, b390, t351 C4H10O3S: d338 C4H10O4S: d336 C4H10S: b388, b389, d337, i104, m378, m379, m380, m395 C4H10S2: b387, d294a C4H10S3: b187 C4H10Zn: d344 C4H11ClSi: c166 C4H11N: b377, b417, b418, d267, d268, d520, i63 C4H11NO: a136, a137, a221, d315, d465, e38, e62

C4H11NO2: a165, a220, d245, d440 C4H11NO3: t423 C4H11O2PS2: d296 C4H11O3P: d314 C4H12BrN: t93 C4H12ClN: t94 C4H12Ge: t109 C4H12IN: t95 C4H12N2: b379, b452, d521, m376, m377 C4H12N2O: a166 C4H12N2S2: c369 C4H12OSi: m108 C4H12O3Si: t326a C4H12O4Si: t92 C4H12Pb: t112 C4H12Si: t120 C4H12Sn: t123 C4H13N3: d298 C4H14OSi2: t105 C4H16O4Si4: t103 C5 C5Cl5N: p12 C5Cl6: h27 C5D5N: p249 C5H3Br2N: d97 C5H3ClO2: f48 C5H3Cl2N: d224 C5H4BrN: b345, b346 C5H4ClN: c233 C5H4FN: f23 C5H4F8O: o18 C5H4N2O3: n76 C5H4N4O: h186 C5H4N4O3: u13 C5H4OS: t156 C5H4O2: f39 C5H4O2S: t157 C5H4O3: c271, f42 C5H5ClN2: a149 C5H5ClN2O2: c167 C5H5F3O2: t293

1.66

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C5H5N: p248 C5H5NO: h173, h174, h175, p262 C5H5NO2: d401, h177 C5H5NO3S: p263 C5H5N3O2: a248 C5H5N3O4: a160 C5H5N5: a69 C5H6: m166 C5H6Br2N2O2: d76 C5H6Cl2N2O2: d173 C5H6Cl2O2: d195, g15 C5H6Cl4O2: t225 C5H6N2: a281, a282, a283, g14, m397, v7 C5H6N2O: a47, a197 C5H6N2OS: h128 C5H6N2O2: d391 C5H6N2O2: e107 C5H6O: m59, m252 C5H6OS: f44 C5H6O2: f46 C5H6O3: g12 C5H6O4: c270, m245 C5H6O4S3: b155 C5H6S: m427 C5H7BrO2: m145 C5H7BrO3: e79 C5H7ClO3: m183, m188 C5H7N: m404 C5H7NO: f47 C5H7NO2: e105 C5H7NS: t158 C5H7N3: a228, d44 C5H7N3O: a192 C5H8: c358, m147, m148, m171, p16, p17, p18, p19, p57 C5H8Br2O2: e115 C5H8Br4: p21 C5H8F4O: m414 C5H8N2: d542, d603, e159, p272 C5H8N2O: m449 C5H8N2O2: d538 C5H8N4O12: p22

C5H8O: c356, c368, d363, e8, m172, p51 C5H8O2: a80, e56, g13, i84, m58, m161, m162, m163, m192, m217, m296, p31, p32, p40, p40a, p50, p208 C5H8O3: e196, m112, o58 C5H8O4: d545, g11, m274, m412 C5H9Br: b263 C5H9BrO2: e81, e82, m144 C5H9Cl: c79 C5H9ClO: c192, d600, m179, p44 C5H9ClOS: b437, c229 C5H9ClO2: b436, e99, e100, i65, m186 C5H9F3O2Si: t376 C5H9N: d602, m178, p33, t78 C5H9NO: b455, b456, c357, e193, m406 C5H9NO2: m118, p273 C5H9NO4: g9 C5H9N3: i8 C5H10 c352, m158, m159, m160, p47, p48, p49 C5H10Br2: d91 C5H10ClNO: d288 C5H10Cl2: d209 C5H10Cl2O2Si: c12 C5H10Cl2Si: c351 C5H10N2: d293, d474 C5H10N2O: d543, p180 C5H10N2O3: g10 C5H10O: a91, c355, d596, i108, m157, m164, m165, m173, m174, m415, p27, p41, p42, t76 C5H10OS: m425 C5H10O2: d454, d598, e208, h139, h156, h157, i66, i87, m102, m175, m176, m177, m286, p36, p219, t68

C5H10O2S: e183, m306, m417 C5H10O3: d289, d451, e162, m68, m278 C5H10O4: b184 C5H10O5: a310, r5, x8 C5H11Br: b305, b322, b323 C5H11BrO2: b269 C5H11BrO2Si: t370 C5H11Cl: c91, c148, c149, c191 C5H11ClSi: a86 C5H11Cl2N: b159 C5H11I: i42, i47 C5H11N: a90, m405, p183 C5H11NO: d304, d597, h167, m307, t69 C5H11NO2: a253, a254, b128, e231, i81, v1 C5H11NO2S: m37 C5H11NO3: n58 C5H11NS2: d295 C5H11O5P: t365 C5H12: d592, m149, p28 C5H12ClN: d475 C5H12Cl2O2Si: b157 C5H12N2: a267, m368, m369 C5H12N2O: b487, t124 C5H12N2O2: b430, o46 C5H12N2S: t122 C5H12N2S2: p271 C5H12O: b460, d452, d595, e209, m153, m154, m155, m156, p37, p38, p39 C5H12OSi: t379 C5H12O2: d594, m57, p30 C5H12O2S: e221 C5H12O3: h141, m66, t352, t425 C5H12O3S: p34 C5H12O4: p20, t114 C5H12O5: x7 C5H12S: b463, e210, m150, m151, m152, p35

1.67

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C5H12Si: t380 C5H13N: a251, a252, d601, m167, m168, m169, p53 C5H13NO: a213, a214, a255, d472, d473, e47, i89, p221 C5H12NOSi: t368 C5H13NO2: a176, d442, d471, d523, m223 C5H13N3: t110 C5H14N2: d593, p29, t113 C5H14OSi: e50, t372 C5H14O2Si: d255 C5H15N3: a175 C6 C6BrD5: b230 C6BrF5: b321 C6Cl4O2: t24, t25 C6Cl5NO2: p10 C6Cl6: h24 C6D6: b10 C6D12: c313 C6F6: h43 C6HBr5O: p6 C6HCl4NO2: t30 C5HCl5: p8 C6HCl5O: p11 C6H2BrFN2O4: b272 C6H2Cl2O4: d172 C6H2Cl3NO2: t242a C6H2Cl4: t22, t23 C6H3Br2F: d84 C6H3Br2NO2: d90 C6H3Br3O, t207 C6H3ClFNO2: c121 C6H3ClN2O4: c94, c95 C6H3ClN2O4S: d627 C6H3Cl2NO2: d203, d204, d205 C6H3Cl3: t222, t223, t224 C6H3Cl3O: t240, t241 C6H3Cl3O2S: d155 C6H3FN2O4: d633

C6H3N3O6: t382, t383 C6H3N3O7: p173 C6H4BrCl: b247, b248, b249 C6H4BrClO2S: b231 C6H4BrF: b288, b289, b290 C6H4BrNO2: b314 C6H4BrN3O4: b271 C6H4Br2: d65 C6H4Br2N2O2: d89 C6H4Br3N: t203 C6H4ClF: c116, c117, c118 C6H4ClFO: c122 C6H4ClI: c135 C6H4ClNO2: c175, c176, c177, c234, c235 C6H4ClNO3: c186 C6H4ClNO4S: n35 C6H4ClO2P: p110 C6H4Cl2: d152, d153, d154 C6H4Cl2N2O2: d202 C6H4Cl2O: d210, d211, d212, d213 C6H4Cl2O2: d171 C6H4Cl2O2S: c43 C6H4Cl3N: t220, t221 C6H4Cl4Si: c208 C6H4FNO2: f21 C6H4F2: d345 C6H4INO2: i45 C6H4I2: d402 C6H4N2: c295, c296, c297 C6H4N2O2: b43 C6H4N2O4: d626 C6H4N2O5: d635 C6H4N4: a273 C6H4N4O6: t381 C6H4O2: b59 C6H5BO2: c21 C6H5Br: b229 C6H5BrO: b325, b326 C6H5BrS: b354 C6H5Cl: c41 C6H5ClHg: p126 C6H5ClN2O2: c172, c173a, c173, c174

C6H5ClO: c194, c195, c196 C6H5ClO2: c87, c88 C6H5ClO2S: b23 C6H5ClS: c243 C6H5ClSe: p151 C6H5Cl2N: d142, d143, d144, d145, d146, d147 C6H5Cl2OP: p137 C6H5Cl2O2P: p105 C6H5Cl2P: d216 C6H5Cl2PS: p138 C6H5Cl3Si: p155 C6H5D: b9 C6H5F: f11 C6H5FO: f22 C6H5FO2S: b24 C6H5F7O2: e137 C6H5I: i27 C6H5NO: n78, p251, p252, p253 C6H5NOS: t153 C6H5NO2: n30, n83, p255, p256, p257 C6H5NO3: h176, n60, n61 C6H5NO4: c272 C6H5N3: b62 C6H5N3O: h103 C6H5N3O4: d625 C6H6: b8a C6H6AsNO6: h153 C6H6BrN: b225, b226, b227 C6H6ClN: c33, c34, c35 C6H6ClNO: a148, c141 C6H6ClNO2S: c42 C6H6Cl2N2: d215 C6H6Cl6: h26 C6H6FN: f9 C6H6HgO: p127 C6H6IN: i26 C6H6N2O: e43, p250, p254 C6H6N2O2: n24, n25, n26 C6H6N2O3: a244, a245, m84

1.68

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C6H6N4O4: d637 C6H6O: p64 C6H6OS: a57, m428 C6H6O2: a44, d377, d378, d379, m251 C6H6O2S: b20, t155 C6H6O3: h146, m253, t304, t305 C6H6O3S: b22 C6H6O4: d460 C6H6O5S: d382 C6H6O6: p207 C6H6O8S2: d381 C6H6S: t159 C6H7AsO3: b11 C6H7BO2: b12 C6H7ClN2: c202, c203, c204, c205 C6H7N: a298, a299, m398, m399, m400 C6H7NO: a257, a258, a259, m101, m403, p264, p265 C6H7NO2S: b21 C6H7NO3S: a118, a119, a120, s23 C6H7NO6S2: a117 C6H7NS: a293 C6H7N3O: p258 C6H7N3O2: n67, n68, n69 C6H7O2P: p135 C6H7O3P: p136 C6H8AsNO3: a115, a116 C6H8Cl2O2: h62, m221 C6H8N2: a223, a224, a225, a226, a227, d238, m121, m257, p107, p108, p109, p118 C6H8N2O: a208, o63 C6H8N2O2S: b25, s22 C6H8N2O3S: d32 C6H8N4: p181 C6H8O: c331, d525, h40, m216 C6H8O2: b375, c322, d364, h42, m214, v4

C6H8O3: a36, d365, f43, h183 C6H8O4: d524, d544 C6H8O6: a312, g8, i59 C6H8O7: c273 C6H9Br: b262 C6H9ClO: c78 C6H9ClO3: e95, e96 C6H9F3O2: b484 C6H9NO: v11 C6H9NOS: m418 C6H9NO2: b438 C6H9NO6: n21 C6H9N3: a158 C6H9N3O2: a159, c284, h83 C6H10: c330, d488, h41, h82, m351 C6H10N2: e172, p184 C6H10N2O2: c323 C6H10N2O4: d279 C6H10N2O5: a14 C6H10N4: p26 C6H10O: c328, d26, d361, e5, e6, h78, m215, m350, m352 C6H10O2: a96, c353, d359, e40, e104, e112, e166, h61, h71, h76, m349 C6H10O3: d436, e53, e54, h121, p214 C6H10O4: d325, d608, e17, h57, m272 C6H10O4S: t151 C6H10O4S2: d709 C6H10O5: d326 C6H10O6: d616 C6H10O8: t84 C6H10S: d27 C6H11Br: b261 C6H11BrO2: b295, e76, e77, e78 C6H11Cl: c77 C6H11ClO: h73 C6H11ClO2: b433, c151, e97

C6H11Cl3Si: c344 C6H11I: i32 C6H11N: d25, h63, m339, m416 C6H11NO: c329, e217, f35, m376, o57, t352 C6H11NO2: e61 C6H12: c312, d498, d499, e84, h75, m213, m347, m348 C6H12Br2: d86 C6H12ClN: c160 C6H12ClNO: c112 C6H12Cl2: d187 C6H12Cl2O: b161 C6H12Cl2O2: b156, d169 C6H12Cl3O3P: t417 C6H12Cl3O4P: t416 C6H12F3NOSi: m440 C6H12NO3P: d293a C6H12N2: d45, t269 C6H12N2O3: s15 C6H12N2O4S2: c371 C6H12N2S4: b174 C6H12N2Si: t373 C6H12N4: h52 C6H12O: a100, b488, c327, d497, d618, e87, h54, h72, h77, i72, m346, o47 C6H12O2: b412, b413, b414, d500, e49, e88, e89, h66, h142, i62, m227, m302, m340, m341, m342, t77 C6H12O3: d435, d457, d515, e37, e152, e154, i99, p2, p232, t67 C6H12O4Si: d23 C6H12O6: f36, g1, g6, i23, m11, s6 C6H12O7: g4 C6H12S: c326 C6H13Br: b294 C6H13BrO2: b267 C6H13Cl: c129 C6H13ClO: c130

1.69

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C6H13ClO2: c81 C6H13ClO3: c105 C6H13Cl3O3Si: t415 C6H13I: i39 C6H13N: c334, h51, m371, m372, m373, m374 C6H13NO: d260, d553, e184, h144, p187 C6H13NO2: a183, a184, h122, i79, L4, L5 C6H13NO4: b182 C6H13NO4S: m451 C6H13NO5: g5, t428 C6H14: d489, d490, h55, m336, m337 C6H14ClN: d272 C6H14Cl4OSi2: b168 C6H14N2: a182, a219, c318, c319 C6H14N2O: a172, h123 C6H14N2O2: L12 C6H14N4O2: a311 C6H14O: b449, d417, d492, d492, d494, d495, d496, d701, e83, h68, h69, h70, m343, m344, m345 C6H14OSi: a97, e33, t374 C6H14O2: b410, d251, d252, d491, e179, h58, h59, h60, i86, m338 C6H14O2S: d704 C6H14O3: b191, d253, e35, e156, h65, h172, t322 C6H14O4: e127, t270 C6H14O4S: d703 C6H14O6: d738, m10, s5 C6H14O6S2: b188 C6H14S: b451, h64 C6H14Si: a104 C6H15Al: t263 C6H15As: t266 C6H15B: t268 C6H15Bi: t267 C6H15ClO2Si: c154 C6H15ClO3Si: c231 C6H15ClSi: b446

C6H15Ga: t274 C6H15In: t276 C6H15N: d411, d696, e85, e86, h80, m353a, t264 C6H15NO: a185, a216, a217, b419, b448, d270 C6H15NOSi: m439 C6H15NO2: d254, e118 C6H15NO3: t264 C6H15NO6S: t424 C6H15N3: a174 C6H15O3B: t260 C6H15O3P: d420, t282 C6H15O3PS: t285 C6H15O4P: t280 C6H15P: t281 C6H15Sb: t265 C6H16Cl2Si2: t104 C6H16N2: d302, h56, t108 C6H16OSi: p218 C6H16Br2OSi2: b150 C6H16O2Si: d249 C6H16O3SSi: m22 C6H16O3Si: t266b C6H16Si: t284 C6H17NO3Si: a280 C6H17NO5S: b180 C6H17N3: i9 C6H18LiNSi2: L11 C6H18N2Si: b172 C6H18N3ClSi: c257a C6H18N3OP: h53 C6H18N4: t272 C6H18OSi2: h50 C6H18O3Si3: h48 C6H19NOSi2: b210 C6H19NSi2: h49 C6N4: t37

C7 C7F5N: p23 C7H3BrClF3: b250 C7H3BrF3NO2: b315

C7H3ClF3NO2: c182, c183, c184 Cl7H3ClN2O5: d630 C7H3ClN2O6: c96 C7H3Cl3O: d160, d161 C7H4BrF3: b233, b234 C7H4ClFO: f14 C7H4ClF3: c51, c52, c53 C7H4ClN: c47, c48 C7H4ClNO: c206 C7H4ClNO3: n41, n42 C7H4ClNO4: c178, c179, c180, n66 C7H4Cl2O: c55, c56, d150 C7H4Cl2O2: d156, d157, d158 C7H4Cl3F: t233 C7H4Cl4S: t34 C7H4F3NO2: n88, n89 C7H4F12O: d718 C7H4I2O3: h111 C7H4N2O2: n40 C7H4N2O6: d628, d629 C7H4N2O7: d638 C7H4O3S: h104 C7H4O4S: s24 C7H5BrO: b66, b228 C7H5BrO2; b232 C7H5BrO3: b348 C7H5ClF3N: a144, a145, a146 C7H5ClN2: a141 C7H5ClO: b67, c38, c39 C7H5ClOS: p103 C7H5ClO2: c45, c46, c46a, c237, c238, p102 C7H5ClO3: c193 C7H5Cl2F: c119 C7H5Cl2N: d196 C7H5Cl2NO: d151 C7H5Cl3: t248, t249 C7H5FO: b69, f10 C7H5FO2: f12, f13 C7H5F3: t300 C7H5F3N2O2: a241, a242 C7H5F3O: t290

1.70

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C7H5F4N: a179 C7H5IO2: i29 C7H5IO3: i51 C7H5I2NO2: a156 C7H5N: b51 C7H5NO: b63, p121 C7H5NO3: n27, n28 C7H5NO3S: s1 C7H5NO4: n37, n38, n39, p259, p260, p261 C7H5NO5: h154 C7H5NS: b60, p122 C7H5NS2: m17 C7H5N3O2: a238, n36, n55 C7H5N3O2S: a240 C7H5N3O6: t386 C7H6BrClO: b252 C7H6BrNO2: n46 C7H6BrNO3: h155 C7H6Br2: b236, d102 C7H6ClF: c123, c124, c125, f16 C7H6ClNO: c40 C7H6ClNO2: a140, c187, c188, c189, n47 C7H6ClNO3: c140 C7H6Cl2: c59, c60, d229, d230, d231 C7H6Cl2O: d191, d192 C7H6F3N: a129, a130, a131 C7H6INO2: a203 C7H6N2: a124, a125, a126, b38 C7H6N2O3: n29 C7H6N2O4: a237, d639, d640, d641 C7H6N2O5: d631, d33a C7H6N2S: a128, m15 C7H6O: b3 C7H6OS: t143 C7H6O2: b44, h94, h95, h96, m240 C7H6O2S: m16 C7H6O3: d375, d376, f41, h99, h100, h101

C7H6O4: d383, d384, d385 C7H6O5: t306 C7H6O6S: s28 C7H7Br: b85, b355, b356, b357 C7H7BrO: b235, b301, b302, b303 C7H7Cl: b89, c244, c245, c246 C7H7ClN4O2: c241 C7H7ClO: c57, c139, c158, c159 C7H7ClO2S: t177 C7H7ClO3S: m49 C7H7ClS: c248 C7H7Cl3Si: b123, t192 C7H7F: f24, f25, f26 C7H7FO: f15, f19 C7H7FO2S: t178 C7H7I: i53, i54 C7H7IO: i41 C7H7N: v9, v10 C7H7NO: a53, a54, a55, b4, f31 C7H7NO2: a121, a122, a123, h97, h98, m401, m402, n85, n86, n87 C7H7NO3: a286, a287, m81, m82, m323, m324, n44, n45 C7H7NO4S: c16 C7H7N3: a201, a202, m136 C7H8: b129, c310, t167 C7H8BrN: b304 C7H8ClN: c58, c142, c143, c144, c145, c146 C7H8ClNO: c138a, c138 C7H8ClNO2S: c247 C7H8Cl2Si: d198, m358 C7H8N2O: a114, b72, p165 C7H8N2O2: d33, h165, m315, m316, m317 C7H8N2O3: m78, m79, m80 C7H8N2S: p154 C7H8N4O2: t138

C7H8O: b78, c279, c280, c281, m48 C7H8OS: m429 C7H8O2: d389, d390, h105, m87, m88, m89, m276 C7H8O2S: t173 C7H8O3: e136, f45, m304 C7H8O3S: m127, t176 C7H8S: m367, p128, t147 C7H9ClSi: m357 C7H9N: b79, d604, d605, d606, d607, e211, e212, e213, m122, t180, t181, t182 C7H9NO: a218, b98, h126, m42, m43, m44 C7H9NO2: d456 C7H9NO2S: t174 C7H9NO3S: a294 C7H9NS: m422, m423 C7H9N3O: a133 C7H10: b130 C7H10N2: a157, a177, a178, d476, m360, t168, t169, t170, t171 C7H10N2O: m94 C7H10N2OS: h129 C7H10N2O2: e173, m232 C7H10N2O2S: a210, t175 C7H10O: m61, m62, n108, t65 C7H10O2: a40, c359 C7H10O3: e12, h158, m333, t341 C7H10O4: d550 C7H10O5: d459 C7H10Si: m366 C7H11Br: b318 C7H11BrO4: d286 C7H11ClO: c316 C7H11ClO4: d290 C7H11NO: c340, h110 C3H11NO2: a52 C7H11NO3: m335 C7H11NO5: a45 C7H11NS: c341

1.71

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C7H12: c311, h22, m207, m208, n107 C7H12O: c309, c315, m204, m205, m206, m268 C7H12O2: b417, c317, d355, e121 C7H12O3: e168, e195 C7H12O4: d317, d318, d552, d574, d575, d576, h8, m273, t126 C7H12O5: g17, g18 C7H12O6Si: m435 C7H12O7: g3 C7H13Br: b260, b306 C7H13BrO2: e80 C7H13ClO: h18 C7H13N: a250, d333, q5 C7H13NO: a317, c339 C7H13NO2: a152 C7H14: c306, h19, m194 C7H14ClN: c113 C7H14N2: d416 C7H14N2O: a278 C7H14N2O2: e201 C7H14O: c308, c342, d569, d578, h5, h15, h16, h17, m197, m198, m199, m200, m201, m202, m203, m267 C7H14O2: b479, c307, d258, e123, e170, e198, h10, i80, m75, m265, p52 C7H14O3: i68 C7H14O6: m256 C7H15Br: b291, b292 C7H15Cl: c128 C7H15ClO2: c82 C7H15Cl3Si: h21 C7H15I: i37 C7H15N: c324, d591, e202, e203, m209, m211, m211 C7H15NO: d469, e157, h125, m375, p185, p186 C7H15NO2: p276 C7H15NO3: c18, m452 C7H15O5P: e119

C7H16: d570, d571, d572, d573, e197, h6, m264, t337 C7H16BrNO2: a38 C7H16ClNO2: a39 C7H16N2: a215, m301, t366 C7H16N2O: a277 C7H16N2O2: p182 C7H16O: d577, h12, h13, h14, m266, t338 C7H16O2: d257, d331, m394 C7H16O2Si: d256, e228 C7H16O3: d700, t278, t321 C7H16O4: t91 C7H16S: h9 C7H17N: h20, m269a C7H17NO: d275 C7H17NO2: b420, d274 C7H17NO5: m255 C7H17NO6S: t427 C7H17NO7S: t426 C7H18N2: d330, h7, i103, t118 C7H18N2O: b173 C7H18N2O2: a276 C7H18O2Si: b486 C7H18O3Si: b485, t266a C7H19NOSi2: b209 C7H19NSi: d343, t371 C7H19N3: d42, t419 C7H21N3Si: t420 C8 C8Br4O3: t10 C8Cl4O3: t31 C8D10: e67 C8HCl4NO2: t32 C8H3NO5: n72 C8H4BrNO2: b296 C8H4Cl2O2: b14, b15, p171 C8H4Cl2O4: d217 C8H4Cl6: b202 C8H4F3N: t298 C8H4F6: b206 C8H4N2: d236, d237 C8H4O3: p168

C8H5Br5: p5 C8H5ClO4: c209 C8H5Cl3O3: t242 C8H5F3O: t289 C8H5F3O2S: t137 C8H5F6N: b205 C8H5NO: b68 C8H5NO2: i21, p170 C8H5NO3: h166, i58 C8H5NO6: n31, n32, n33, n34 C8H6: p82 C8H6BrClO: b246 C8H6BrN: b329 C8H6Br2O: d64 C8H6Br4: t11, t12 C8H6ClF3: t299 C8H6ClN: c201 C8H6ClNO3: c171 C8H6Cl2O: d140 C8H6Cl2O3: d214 C8H6Cl4: t35 C8H6N2: q4 C8H6N2O2: a266, n65 C8H6N2O6: d636, m228 C8H6O: b42 C8H6O2: b13, p169 C8H6O3: b70, c14, f33, m239 C8H6O4: b16, b17, m241, p167 C8H6S: b61 C8H7Br: b349 C8H7BrO: b221, b222 C8H7BrO2: b327, b328 C8H7ClO: c28, c29, c30, p81, t187, t188, t189 C8H7ClOS: b91 C8H7ClO2: b90, c200, m53, p69 C8H7ClO3: c86, c197, m184, m185 C8H7ClO4: c133 C8H7FO: f8 C8H7N: i18, p80, t184, t185, t186

1.72

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C8H7NO: m9, m137, t190 C8H7NO2: h133, n84 C8H7NO3: n22, n23 C8H7NO3S: t179 C8H7NO4: a116a, m318, m319, m320, m321, n62, n63, n64 C8H7NO5: m83 C8H7NS: b121, m135 C8H7N3O2: a153 C8H8: s11 C8H8BrNO: b219 C8H8Br2: d79, d104, d105 C8H8ClNO: c23 C8H8ClNO3S: a10 C8H8Cl2: d233, d234 C8H8Cl2Si: p166 C8H8HgO2: p125 C8H8N2: a260, m128 C8H8N2OS: a207 C8H8O: a31, e9, m126, p76a C8H8OS: m424, p153 C8H8O2: b41, b97, h90, h91, h92, m45, m46, m129, m130, m131, m132, p78, p79 C8H8O2S: t160 C8H8O3: d370, d380, h130, h131, h137, h138, h160, m8, m50, m51, m52, m242, m277, m410, p68, t74 C8H8O4: d21, h132 C8H8O4S: a33 C8H9Br: b282, b283, b368, b369, b370, b371 C8H9BrO: b270, b286 C8H9BrO2: b268 C8H9Cl: c107, c108, c258, c259, c260, c261 C8H9ClO: c90 C8H9N: b100, c360, i22, m447

C8H9NO: a18, a108, a109, a110, b96, m249 C8H9NO2: a15, a16, a17, a211, a212, b88, d556, d557, d558, d559, e187, e214, e215, e216, m47, m116, m117, p115, t75 C8H9NO3: a206, h163, h164, m85, n59 C8H9NO4: d444 C8H10: e68, m244, x4, x5, x6 C8H10N2O: d560 C8H10N4O2: c1, d240 C8H10O: b131, d579, d580, d581, d582, d583, d584, e28, e199, m105, m106, m107, m138, m139, m140, p112, p113 C8H10O2: b18, d431, d432, d433, m54, p72, p111 C8H10O3: c320, d446, h135, h159 C8H10O3S: m434 C8H10O4: d263 C8H10S: b105 C8H11ClSi: d585 C8H11N: b103, d477, d478, d479, d480, d481, d482, d483, e63, e64, e65, e180, e181, m141, m142, p114, t367 C8H11NO: a173, a256, a261, a262, a300, d470, e24, h117, m55, m71, m72, m73, p266 C8H11NO2: d427, d428, d429 C8H11NO2S: m433 C8H11NO3: e132 C8H11NO3S: d463 C8H11N5: p93 C8H12: c345, v6 C8H12N2: d239, d586, t119, x9 C8H12N2O2: d410 C8H12N2O3: d280 C8H12N4: a323

C8H12O: e234 C8H12O2: d508, e219, h185, n111 C8H12O3: e194 C8H12O4: d305, d316 C8H12O6Si: t195 C8H12Si: d587 C8H13N: e235 C8H14: c349, d532, o17, o44, v5 C8H14N2: p188 C8H14O: c348, d510, e7a, m262, o45 C8H14O2: b459, c333, c363, d537, i69, m195 C8H14O3: b415, b496, d712, e90 C8H14O4: b447, d320, d335, d536a, e149, o24 C8H14O4S: d619 C8H14O4S2: d708 C8H14O6: d339, d340 C8H14O6Si: t194 C8H15ClO: e145, o37 C8H15N: o27 C8H15NO: d367 C8H15NO2: d468, e204, e205, e206 C8H16: c346, d506, d507, e108, o39, t357 C8H16ClN: c227 C8H16O: c347, d509, e109, e110, o34, o35, o36, o40 C8H16O2: b431, c321, e142, e143, h79, i67, m261, o29, p234 C8H16O4: e36, t125 C8H17Br: b320 C8H17Cl: c190 C8H17Cl3Si: o43 C8H17I: i46 C8H17N: c350, d511 C8H17NO2: p189 C8H17NO3S: c335 C8H17O5P: t283

1.73

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C8H18: d533, e140, e174, e175, m260, o22, t100, t353, t354, t355 C8H18ClNO2: a49 C8H18Cl2O2Si3: d186 C8H18Cl2Si: d184 C8H18Cl2Sn: d136a C8H18F3NOSi2: b212 C8H18N2: c314 C8H18N2O: m224, m367 C8H18N2O4S: h124 C8H18O: d115, d407, e144, o30, o31, o32, o33 C8H18OSi2: d713 C8H18OSn: d137 C8H18O2: d122, d535, e141, o25, o26, t356 C8H18O2S: d135 C8H18O3: b176, b411, d698, t277 C8H18O3S: d134 C8H18O3Si: t262 C8H18O4: b189 C8H18O4S: d131 C8H18O5: t51 C8H18S: d132, d133, o28 C8H18S2: b153, b154, d113, d114 C8H18Si2: b208 C8H19N: d107, d406, d418, d536, e147, o41, t102 C8H19NO: d412 C8H19NO2: b444, d247, d248 C8H19NO5: b183 C8H19O3P: d127 C8H20BrN: t48 C8H20ClN: t49 C8H20Ge: t56 C8H20N2: d534, o23, t101, t273 C8H20O3SSi: m19 C8H20O3Si: t261 C8H20O4Si: t47 C8H20O5P2: t59 C8H20O7P2: t58

C8H20Pb: t57 C8H20Si: t60 C8H20Sn: t62 C8H21NO: t50 C8H21NOSi2: b207 C8H21NO2Si: a275 C8H22N2O3Si: a167a, t324 C8H22N4: b145 C8H22O2Si2: b211 C8H23N5: t54 C8H24Cl2O3Si4: d207 C8H24O2Si3: o21 C8H24O4Si4: o20 C8H28N4Si4: o19 C9 C9F15N3: t432 C9H2Cl6O3: h30 C9H3Cl3O3: b32 C9H4O5: b31, c15 C9H5BrClNO: b255 C9H5Br2NO: d87 C9H5ClINO: c132 C9H5Cl2N: d225 C9H6BrN: b347 C9H6ClN: c236 C9H6ClNO: c134 C9H6N2O2: n77, t172 C9H6O2: b56, c276 C9H6O3: h108, h109 C9H6O4: i16 C9H6O6: b28, b29, b30 C9H7BrO: b259 C9H7ClO: c268 C9H7ClO2: c76 C9H7Cl3O3: t243 C9H7N: i110, q3 C9H7NO: h178, i20 C9H7NO3: h143, m285 C9H7NO4S: h179 C9H7N3O4S2: a247 C9H8: i17 C9H8Cl2O2: n109 C9H8N2: m409

C9H8N2O5: n43 C9H8O: c266, i15 C9H8O2: c267, d353 C9H8O3: h107 C9H8O4: a56, p124 C9H9BrO: b342 C9H9Cl: c217 C9H9ClO: c223 C9H9ClO3: c199, c249 C9H9N: d486, m283, m284 C9H9NO: m93 C9H9NO2: a9 C9H9NO2S: t191 C9H9NO3: a11, a12, b71 C9H9N3O: a265 C9H10: a84, i13, m411, v3 C9H10F3NO2: m123 C9H10N2: a301, p119a C9H10N2O: p147 C9H10N2O2: p83 C9H10N2O3: a132 C9H10O: a98, a99, c269, d360, i14, m113, p144, p145, p209, p217 C9H10O2: b77, d485, e9a, e25, e26, e69, h170, h171, m39, m40, m41, m356, p74, p146 C9H10O2S: b120 C9H10O3: d430, e29, e30, e39, e48, e151, e218, m91, m279, m292, p75 C9H10O4: d434, m288, m445 C9H10O8: c354 C9H11Br: b297, b331, b361, b362 C9H11BrO: b343 C9H11ClO3S: c114 C9H11Cl3Si: c226, m354 C9H11N: a83, a199, a200, c332, t71, t80 C9H11NO: d462, m355, m432 C9H11NO2: d464, e27, e59, e60, p84

1.74

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C9H11NO3: t437 C9H12: e158, i91, n91, p222, t333, t334, t335, v8 C9H12Cl2Si: m353 C9H12N2O4: a246 C9H12N2O6: u14 C9H12O: b95, d547, d548, i106, i107, p142, p143, p235, t358, t359, t362 C9H12O2: b110, e31, i85, n110, p73, p140, t348 C9H12O3: m196, t315 C9H12O3S: e222 C9H12S: p141 C9H13N: b480, d487, d622, e72, e169, e223, e224, i90, t330 C9H13NO: a264, b80, m86, n112 C9H13NO2: a263 C9H13N3O2: t438 C9H14BrN: p159 C9H14Br3N: p162 C9H14ClN: p160 C9H14IN: p161 C9H14N2: n94 C9H14O: d527, d529, i82, t340 C9H14OSi: t375 C9H14O2Si: d443 C9H14O3: b192 C9H14O3Si: p158 C9H14O5: d262, d321 C9H14O6: p201 C9H14Si: p163 C9H15NO: c361 C9H15NO2: d568 C9H15NO5: d261 C9H15NSi: t369 C9H16: h46 C9H16Cl2Si: c333a C9H16N2: d46 C9H16O: d528 C9H16O2: c325 C9H16O3: b467

C9H16O4: d303, d307, d322, d530, n95 C9H17ClO: n101 C9H17N: a88, n97 C9H17NO: m180 C9H17NO2: e177, e178 C9H18: i94, n102, p224, t339 C9H18NO: t117 C9H18N2O3Si: t325 C9H18O: d531, n100, n103 C9H18O2: e138, m329, n98 C9H18O3: d111 C9H19Br: b317 C9H19N: i95, t332 C9H19NO: d116 C9H19NO2: e120 C9H19NO3S: c337 C9H20: n92, t346 C9H20Cl2Si: m330 C9H20N2: a296 C9H20N2S: d136 C9H20O: n99, t347 C9H20O2: b450, n96 C9H20O3: d699, t279 C9H20O3Si: a103 C9H20O4: t408 C9H20O5: t53 C9H21BO3: t406 C9H21ClO3Si: c230 C9H21ClSi: c257 C9H21N: n104, t407 C9H21NO3: t309 C9H21N3: t275 C9H21O3B: t310 C9H21O3P: t313 C9H22N2: d327, n93 C9H22O3Si: p238 C9H23NO3Si: a279 C9H24N4: b147 C10 C10H2O6: b27 C10H4Cl2O2: d201

C10H6N2: b99 C10H6N2O4: d634 C10H6N2O4S: d48 C10H6O2: n11 C10H6O3: h152 C10H6O8: b26 C10H7Br: b312 C10H7BrO: b313 C10H7Cl: c168, c169 C10H7NO2: n57, n81, p123 C10H7NO8S2: n82 C10H8: a326, n2 C10H8BrNO2: b287 C10H8N2: d705 C10H8O: n9, n10 C10H8O2: d392, d393, d394, d395, m191 C10H8O3: h140 C10H8O3S: n18 C10H8O7S2: h150, h151 C10H8O8S2: d396 C10H9ClCrN2O3: b143 C10H9N: m407, m408, n17 C10H9NO: a51, a236 C10H9NO2: i19 C10H9NO3S: a234 C10H9NO4S: a193, a194, a195, a196 C10H9NO6: d561 C10H9NO6S2: a232, a233 C10H9N3: d706 C10H10ClFO: c120 C10H10ClNO2: c26 C10H10N2: a285, n4, n5 C10H10N2O: m365 C10H10O: d362, m190, p96, p98 C10H10O2: b64, s2 C10H10O3: b73, m60 C10H10O4: d588, d589, d590, h136, p152 C10H11BrO: b312a C10H11ClO3: c198 C10H11ClO4: t317 C10H11IO4: i28 C10H11N: p101

1.75

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C10H11NO2: a32, d448 C10H11NO4: c10 C10H11NO6: m226 C10H12: d244, t73 C10H12NO: b408 C10H12N2: a170, b81, b102 C10H12N2O2: p77 C10H12O: a94, b500, e55, i77, m97, m386, m387, m391, p94, p95 C10H12O2: e200, h112, h162, m70, m92, m98, m99, m100, p99, p100, p223 C10H12O3: d426, e41, e163, m300, p71, p230 C10H12O4: d447, m225, t314 C10H12O5: d306, p239, t316 C10H12O6: d514 C10H13Br: b298 C10H13BrO: b243 C10H13Cl: b434 C10H13NO: p129 C10H13NO2: e45 C10H13NO2S: b92 C10H13N5O4: a70 C10H14: b423, b424, b425, d282, d283, d284, i64, i100, i101, i102, t97, t98, t99 C10H14NO5PS: p3 C10H14N2: n20, p139 C10H14N2O: d323, d334 C10H14N4O4: d399 C10H14N5O7P: a72 C10H14O: b469, b470, b471, b472, b473, b477, c20, c362, i92, i102a, p58, t116, t254 C10H14O2: b432, b454, d450 C10H14O3: c6, c9 C10H14O4: m90, t318 C10H15BrO: b245

C10H15N: b421, d277, d278, d564, e233, i93, p97, t96 C10H15NO: d273, e1, e2 C10H15NO2: d451, p106 C10H15N5O10P2: a71 C10H16: a67, c2, d649, L6, L7, m453, p25, p175, p176, t5, t6, t253 C10H16ClN: b126 C10H16Cl2O2: d11 C10H16N2O8: e125 C10H16O: c3, c4, d352, d562, d563, L8, p177, p178, p243, t351 C10H16OSi: d519 C10H16O4: c5, d266 C10H16O4S: c7 C10H16O5: d265, d301 C10H16Si: b127 C10H17N: a66, p274 C10H17NO: c343, m450 C10H18: d1, d2, p174 C10H18N2O7: h119 C10H18O: b216, b441, b442, c265, d3, g2, i60, i83, i109, L9, m13, p190, t7, t350 C10H18O2: e112 C10H18O3: d599, t70 C10H18O4: b175, d9, d121, d332, d565 C10H18O4S: d341 C10H18O6: d421 C10H19ClO: d17 C10H19N: d12, t331 C10H19NO2: e207 C10H20: c301, d18 C10H20Br2: d73 C10H20N2S4: t61 C10H20O: b439, b440, c274, d6, d16, d357, d366, e148, m12, m303 C10H20O2: d14, e146, e190, m63, m170 C10H20O5: p45

C10H20O5Si: t326 C10H21Br: b265 C10H21Cl: c80 C10H21I: i33 C10H21N: d294 C10H21NO: a230 C10H22: d7 C10H22N2: d41 C10H22O: d15, d651, t72 C10H22O2: d10, d106 C10H22O3: d697, t413 C10H22O3S: d13 C10H22O4: t412 C10H22O5: b190 C10H22O7: d648 C10H23N: d19, d650 C10H23NO: d108 C10H23NO2: d259 C10H24N2: d8, t55, t111 C10H24N2O2: d645 C10H24N4: b146 C10H24OSi: m109 C10H24O3Si: m441 C10H24O6Si: t429 C10H27O3N3Si: t323 C10H30O3Si4: d5 C10H30O5Si5: d4 C11 C11H4F20O: i1 C11H7N: c293 C11H8O: n1 C11H8O2: h147, m310, n3 C11H8O3: h148, h149 C11H9Br: b309 C11H9Cl: c157 C11H9N: p148 C11H10: m308, m309 C11H10N2S: n19 C11H10O: m76, m77 C11H11N: n6 C11H12N2O: a309 C11H12N2O2: t436 C11H12O2: d358, e103, m104

1.76

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C11H12O3: e70 C11H13ClO: b428 C11H13ClO3: c250 C11H13NO: b119 C11H13NO2: t183 C11H13NO3: a302, a303 C11H13N3O: a113 C11H13N3O3S: d567 C11H14O: m103, p43 C11H14O2: b426, b427, d455, e46 C11H14O3: b409, b468, b476, e167 C11H14O4: e155 C11H14O4Si: d24 C11H15NO: d269 C11H15NO2: d276, d466, e122 C11H16: b482, p24, p54 C11H16N2: b114 C11H16O: b86, b461, b462, p56 C11H16O2: a68 C11H16O3: m299 C11H16O4: d714 C11H17N: b429, e160 C11H17NO: e225 C11H17NO2: b104 C11H17O3P: b93 C11H18O: d308, n105, p4 C11H18O5: d264 C11H19ClO: u11 C11H19N: a209 C11H20O: p55, u7 C11H20O2: u9 C11H20O4: d119, d287, d309 C11H21BrO2: b367 C11H22: u8 C11H22N2: d695 C11H22O: u1, u5, u6, u10 C11H22O2: m218, u3 C11H22O4Si: e7 C11H23NO2: a297 C11H24: u2 C11H24O: d310, u4 C11H24O3Si: t311

C11H24O4: t410 C11H24O6: p46 C11H24O6Si: t430 C11H26N2: d129 C11H26N2O6: b214 C12 C12Br10O: b197 C12H4Cl6S2: b203 C12H5ClO3: c170 C12H6Br4O4S: s25 C12H6O3: n7 C12H6O12: b19 C12H7NO2: n8 C12H8: a3 C12H8Br2: d66 C12H8Cl2OS: b166 C12H8Cl2O2S: b165 C12H8N2: p63 C12H8N2O2: a235 C12H8N2O4S2: b194, b195 C12H8O: d50 C12H8O6: b132 C12H8S: d52 C12H9Br: b237 C12H9BrO: b330 C12H9ClO2S: c207 C12H9N: c8, d665, n16 C12H9NO: b74, b75, b76 C12H9NO2: n48, n49 C12H9NO3: n70, n71 C12H9NS: p66 C12H10: a2, b134 C12H10ClN: c61, c62 C12H10ClO3P: d662 C12H10ClP: c99 C12H10Cl2Si: d175 C12H10Hg: d675 C12H10N2: a322 C12H10N2O: n80, p89 C12H10N2O2: n52 C12H10N2O2S: a243 C12H10N3O3P: d682

C12H10O: d667, m311, m312, p131, p132 C12H10OS: d690 C12H10O2: d387, h88, n14, n15 C12H10O2S: d689, t150 C12H10O3: n12 C12H10O3S: b139 C12H10O4: q1 C12H10O4S: s27, t145 C12H10S: d688 C12H10S2: d664 C12H10Se2: d663 C12H11ClNO2P: p134 C12H11N: a134, a135, b117, b118, d655 C12H11NO: n13, p70 C12H11N3: p87 C12H11O3P: d681 C12H12: d554, d555 C12H12N2: b136, d673, p131 C12H12N2O: o62 C12H12N2O2: b40 C12H12N2O2S: d36, d37 C12H12N4: d31 C12H12O: e44 C12H12O2Si: d687 C12H12O3: t196 C12H12O6: t193, t336 C12H13N3: d34 C12H14N2O3S: a167 C12H14N4O2S: s21 C12H14O3: e176 C12H14O4: d329 C12H15N: d369 C12H15NO: b116 C12H15N3O3: t197 C12H16: c338, m212, p104 C12H16O2: m364 C12H16O3: d246 C12H17N: b115, c337 C12H17NO: d319, d342 C12H18: b489, c304, d414, d415, h47, p117, t435 C12H18Cl2N4OS: t139

1.77

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C12H18O: d419, d513 C12H18O2: b474, b475 C12H18O4: b445 C12H19N: d413, h81 C12H20O2: b185, b217, e102, L10 C12H20O3Si: p157 C12H20O4: d118 C12H20O4Si: t8 C12H21N: t431 C12H21N3: t422 C12H22: c305, d241 C12H22O: c303, e4 C12H22O3: h67 C12H22O4: d130, d324, d512, d702, d721 C12H22O11: L3, m7, s20 C12H23ClO: d728 C12H23N: d242, d724 C12H23NO: a318 C12H24: d729 C12H24N2: d694 C12H24O: c302, d731, m443, t349 C12H24O2: d726, e113 C12H24O6: h74 C12H25Br: b275 C12H25Cl: c100 C12H25Cl3Si: d736 C12H26: d719 C12H26O: d350, d727, t354a C12H26O2: d722, d723 C12H26O3: b151 C12H26O4: t411 C12H26O4S: d735 C12H26S: d725 C12H27Al: t307 C12H27BO3: t209 C12H27ClSn: t215 C12H27N: d349, d732, t210 C12H27O3P: t214 C12H27O4P: t212 C12H27P: t213 C12H28BrN: t135 C12H28N2: d720

C12H28O4Si: t88, t134 C12H28O4Ti: t166 C12H28O8Si: t89 C12H36O4Si4Ti: t90 C13 C13H5N3O7: t384 C13H8ClNO3: c181 C13H8ClNOS: p67 C13H8Cl2O: d159 C13H8N2O7: b193 C13H8O: f3 C13H8OS: t165 C13H8O2: x3 C13H9BrO: b232 C13H9ClO: c49, c50 C13H9ClO2: c131 C13H9N: a61 C13H10: f2 C13H10ClNO: a142, a143, d659 C13H10Cl2O2: m233 C13H10N2: p90 C13H10N2O3: a239 C13H10O: b53, x1 C13H10O2: b135, h102, p91 C13H10O3: d386, d661, p150 C13H10O5: t83 C13H11Br: b274 C13H11Cl: c97 C13H11ClO: c44 C13H11NO: a127, b5 C13H11NO2: h161, p85 C13H11NO3: p86 C13H12: d676 C13H12N2: b54, d38, d670 C13H12N2O: d693 C13H12N2S: d692, t146 C13H12N4O: p88 C13H12N4S: d691 C13H12O: b138, d677, h113, m56, p76 C13H12S: b113

C13H13ClSi: c98 C13H13N: d678, m230, m93 C13H13NO: b106 C13H13N3: d671 C13H14N2: d35, m238, t344 C13H14N2O3: a59 C13H14N4O: d660 C13H14Si: m231 C13H16O2: m74 C13H16O3: e71 C13H16O4: d328 C13H17NO2: e74 C13H20: p116 C13H20N2O2: d271 C13H20O: i56, i57 C13H22ClN: b125 C13H22N2: d243 C13H22O2: n106 C13H22O3Si: b124 C13H26: t258 C13H26N2: m236, t343 C13H26O2: e229, t257 C13H27Br: b359 C13H28: t256 C13H28O4: t409 C13H29NO4: b169 C14 C14H6Cl2O2: d148, d149 C14H7ClO2: c36, c37 C14H8ClNO5: c185 C14H8O2: a305, p62 C14H8O3: h93 C14H8O4: d371, d372, d373, d374 C14H8O5S: a308 C14H8O8: a306, d312 C14H9Br: b324 C14H9ClO3: c54 C14H9Cl5: b167 C14H9NO2: a111, a112 C14H9NO3: a186

1.78

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C14H10: a304, d654, p61 C14H10Br2O: b273 C14H10ClNO3: a147 C14H10Cl2O4: b162 C14H10Cl4: b163 C14H10N2O2: d28, d29, d30 C14H10O2: b34 C14H10O3: b45, b65, x2 C14H10O4: b137, d54, t82 C14H11N: d653, p120 C14H11NOS: a50 C14H12: d351, s9 C14H12Cl2O: b164 C14H12N2O: b37 C14H12N2O2: b35 C14H12O: a34, d22, m133, m134 C14H12O2: b46, b83, b84, b107, b108, d652 C14H12O3: b36, h35 C14H13ClO: c147 C14H13N: e93, i12 C14H13NO: b82 C14H13NO2: b50 C14H14: d666 C14H14N2: a168 C14H14N2O3: a325 C14H14O: d58 C14H14OS: b200 C14H14O2: b109 C14H14S2: b199, d57 C14H15N: d56, d668 C14H15O3P: d61 C14H16N2: d669 C14H16O2Si: d437 C14H16O4: d281 C14H18O4: d285 C14H20N2O6S: m120 C14H20O5: b39 C14H22: p130a C14H22O: d123, d124, d125, d126 C14H22O2: d112 C14H23N: d109, o42 C14H23N3O10: d299 C14H26O3: h11 C14H26O4: d408

C14H27ClO: t41 C14H28: t42, t43 C14H28O2: t39 C14H29Br: b352 C14H29Cl3Si: t46 C14H30: t38 C14H30O: t40 C14H31N: t44 C14H32N2O4: t87 C15 C15H10O2: b101, m124 C15H11NO: d679 C15H12N2O2: d672 C15H12O: d354, d685 C15H12O2: d53 C15H13NO: a13 C15H14O: d684 C15H14O2: b49, b141, d686 C15H14O3: b111 C15H16O: m359 C15H16O2: i97 C15H17N3: d711 C15H18OSi: e42 C15H22O3: d117 C15H24: t312 C15H24O: d120 C15H26O: h184 C15H26O6: g19 C15H30N2: t342 C15H30N3OP: t405 C15H30O: p14 C15H30O2: m413 C15H32: p13 C15H32O3Si4: p164 C15H32O10: t389 C16 C16H10: b52, fl, p246 C16H11NO2: p149 C16H12N2O5S: a60 C16H12N4O9S2: t3

C16H13N: p130 C16H14: d656, d657, e66 C16H14O: d658 C16H14O6S: s26 C16H15NO4: d445 C16H16O2: b47, b112 C16H16O3: d449 C16H18ClN3S: m237 C16H19ClSi: b435 C16H20N2: d59 C16H20O2Si: d250 C16H22O4: d128, d409 C16H22O11: g7 C16H26O3: d730 C16H26O7: t52 C16H32: h37 C16H32O2: h35 C16H33Br: b293 C16H33I: i38 C16H33NO: d297 C16H34: h4, h32 C16H34O: h36 C16H34O2: h33 C16H34S: d644, h34 C16H35N: d643, h38 C16H35O4P: b178 C16H36BF4N: t19 C16H36BrN: t14 C16H36ClN: t15 C16H36FN: t16 C16H36IN: t18 C16H36O4Si: t13 C16H36Sn: t20 C16H37NO4S: t17 C17 C17H6O7: b55 C17H10O: b8 C17H12O3: p119 C17H13N3O5S2: p172 C17H16O4: d60 C17H18O3: b478 C17H20N2O: b171 C17H20N4O6: r4

1.79

ORGANIC COMPOUNDS

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C17H21NO4: c275 C17H22N2: m234 C17H23NO3: a315 C17H34O2: m263 C17H36: h1 C17H37N: m229

C18H38S: o4 C18H39ClSi: t302 C18H39N: o13, t301 C18H39O7P: t414 C18H40Si: t303 C19

C18 C18H9Cl6O4P: t418 C18H10O6: h85 C18H12: b6, b7, t396 C18H12N5O6: d683 C18H14: t4 C18H14O: d680 C18H14O8: d55 C18H15As: t394 C18H15N: t392 C18H15N3Si: a320 C18H15O3P: t403 C18H15O4P: t399 C18H15P: t400 C18H15PS: t402 C18H15PSe: t401 C18H15Sb: t393 C18H16O2: b422 C18H16Si: t404 C18H18O3: e73 C18H20O2: b48 C18H25NO3: i61 C18H30O: t211 C18H30O2: o7 C18H31N: d733 C18H32O2: o1 C18H32O16: r1 C18H34O2: o10, o11 C18H34O4: d110 C18H36: d734, o8 C18H36O: o12 C18H36O2: e139, o5 C18H37Br: b319 C18H37Cl3Si: o15 C18H37N: o9 C18H37NO: o2 C18H38: o3 C18H38O: o6

C19H15Br: b366 C19H15Cl: c256 C19H16: t397 C19H16O: t398 C19H18BrP: m442 C19H20Br4O4: i96 C19H20O4: b87 C19H22N2O: c264 C19H30O5: m243 C19H32: p156 C19H34ClN: b122 C19H34O2: m325 C19H36O2: m327 C19H37NO: o14 C19H38O2: m326 C19H40: n90, t115 C19H40Cl2Si: m328 C20 C20H10Br2O5: d83 C20H12: b57, b58, d49 C20H12O5: f4 C20H14O4: p65 C20H15Br: b365 C20H18O3Si: t391 C20H19N3: b2 C20H22O6: t271 C20H24N2O2: q2 C20H24O6: d51 C20H28O2P: d674 C20H30O2: a1 C20H31N: d20 C20H35N: t45 C20H36O2: e188 C20H38O2: e189 C20H40: i3

C20H40O: o16 C20H42: i2 C21 C21H15NO: b142 C21H15N3O3: t390 C21H21N: t200 C21H22N2O2: s10 C21H24O2: b144 C21H28N2O: b170 C21H36O: p15 C21H39N3: t255 C22 C22H23N3O9: a316 C22H30O2S: t144 C22H34O4: b443 C22H39N: h39 C22H42O4: d312 C22H44O2: b466, d716 C22H46: d715 C22H46O: d717 C23 C23H16O6: m235 C23H26N2O4: b372 C24 C24H16N2O2: b198 C24H18: t395 C24H20BNa: t128 C24H20O4Si: t127 C24H20Si: t132 C24H20Sn: t133 C24H22N2O: b140 C24H38O4: b179, d313 C24H40O5: c263 C24H46O4: d643a C24H50: t36 C24H51N: t387

1.80

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SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C24H51O3P: d423, t421 C24H52O4Si: t85 C24H54OSn2: b201

C27H46O: c262 C27H50ClN: b94 C28

C26 C26H20: t131 C26H26N2O2S: b152 C26H26OSi2: t130 C26H50O4: b177, d311 C27 C27H19NO: b148 C27H42ClNO2: b33

C28H22: t129 C28H31ClN2O3: r2 C28H32O2Si3: t121 C30 to C40 C30H50: s8 C30H62: s7 C30H63O3P: t308 C32H66: d737

C32H68O4Si: t86 C36H75O3P: d642 C38H30NiO2P2: b213 C39H74O6: g20 C40H56: c19 C40H82O6P2: b196 C45 to C57 C45H86O6: g24 C48H40O4Si4: o38 C51H98O6: g23 C57H104O6: g22

TABLE 1.15 Physical Constants of Organic Compounds See also the special tables of fats, oils, and waxes. Names of the compounds in the table starting on p. 1.82 are arranged alphabetically. Usually substitutive nomenclature is employed; exceptions generally involve ethers, sulfides, sulfones, and sulfoxides. Each compound is given a number within its letter classification; thus compound c195 is 3-chlorophenol. The section “Nomenclature of Organic Compounds” should be consulted to familiarize oneself with present nomenclature systems. Synonyms or Alternate Names are found at the bottom of each spread in their alphabetical listing; the number following the name refers to the numerical place of this compound in the table. For example, epichlorohydrin, c101, indicates that this compound is found listed under the name 1-chloro-2,3-epoxypropane. Formulas are presented in a semistructural form when no ambiguity is possible. Complicated systems are drawn in complete structural form and located at the bottom of each page and keyed to the number of the entry. Beilstein Reference. In the column so headed is found the reference to the volume and page numbers of the fourth edition of Beilstein: (Handbuch der Organischen Chemie) (Springer-Verlag, New York). Thus the entry 9, 202 refers to an entry in volume 9 appearing on page 202. When the volume number has a superscript attached, reference is made to the appropriate supplementary volume. For example, 122, 404 indicates that the compound will be found listed in the second supplement to volume 12 on page 404. The earliest Beilstein entry is listed. Supplementary information may be found in the supplements to the basic series; such coordinating references (series number, volume number, and page number of the main edition) along with the system number are found at the top of each odd-numbered page. Similarly, a back reference such as H 93; E II 64; E III 190 in a volume of Supplementary Series IV means that previous items on

1.80

Previous Page

SECTION 1

TABLE 1.14 Empirical Formula Index for Organic Compounds (continued ) The alphanumeric designations are keyed to Table 1.15

C24H51O3P: d423, t421 C24H52O4Si: t85 C24H54OSn2: b201

C27H46O: c262 C27H50ClN: b94 C28

C26 C26H20: t131 C26H26N2O2S: b152 C26H26OSi2: t130 C26H50O4: b177, d311 C27 C27H19NO: b148 C27H42ClNO2: b33

C28H22: t129 C28H31ClN2O3: r2 C28H32O2Si3: t121 C30 to C40 C30H50: s8 C30H62: s7 C30H63O3P: t308 C32H66: d737

C32H68O4Si: t86 C36H75O3P: d642 C38H30NiO2P2: b213 C39H74O6: g20 C40H56: c19 C40H82O6P2: b196 C45 to C57 C45H86O6: g24 C48H40O4Si4: o38 C51H98O6: g23 C57H104O6: g22

TABLE 1.15 Physical Constants of Organic Compounds See also the special tables of fats, oils, and waxes. Names of the compounds in the table starting on p. 1.82 are arranged alphabetically. Usually substitutive nomenclature is employed; exceptions generally involve ethers, sulfides, sulfones, and sulfoxides. Each compound is given a number within its letter classification; thus compound c195 is 3-chlorophenol. The section “Nomenclature of Organic Compounds” should be consulted to familiarize oneself with present nomenclature systems. Synonyms or Alternate Names are found at the bottom of each spread in their alphabetical listing; the number following the name refers to the numerical place of this compound in the table. For example, epichlorohydrin, c101, indicates that this compound is found listed under the name 1-chloro-2,3-epoxypropane. Formulas are presented in a semistructural form when no ambiguity is possible. Complicated systems are drawn in complete structural form and located at the bottom of each page and keyed to the number of the entry. Beilstein Reference. In the column so headed is found the reference to the volume and page numbers of the fourth edition of Beilstein: (Handbuch der Organischen Chemie) (Springer-Verlag, New York). Thus the entry 9, 202 refers to an entry in volume 9 appearing on page 202. When the volume number has a superscript attached, reference is made to the appropriate supplementary volume. For example, 122, 404 indicates that the compound will be found listed in the second supplement to volume 12 on page 404. The earliest Beilstein entry is listed. Supplementary information may be found in the supplements to the basic series; such coordinating references (series number, volume number, and page number of the main edition) along with the system number are found at the top of each odd-numbered page. Similarly, a back reference such as H 93; E II 64; E III 190 in a volume of Supplementary Series IV means that previous items on

1.81

ORGANIC COMPOUNDS

this compound are found in the same volume of the Basic Series on page 93, of Supplementary Series II on page 64, and of Supplementary Series III on page 190. The absence of a back reference implies that the compound involved is described for the first time in the series concerned. Formula Weights are based on the International Atomic Weights of 1973 and are computed to the nearest hundredth. Density values are given at room temperature unless otherwise indicated by the superscript figure; thus 0.9711112 indicates a density of 0.9711 for the substance at 112 C. A densityof 0.89916 4 indicates a density of 0.899 for the substance at 16 C relative to water at 4 C. Refractive Index, unless otherwise specified, is given for the sodium line at 589.6 nm. The temperature at which the measurement was made is indicated by the superscript figure; otherwise it is assumed to be room temperature. Melting Point is recorded in certain cases as 250 d and in some other cases as d 250, the distinction being made in this manner to indicate that the former is a melting point with decomposition at 250 °C, while the latter decomposition occurs only at 250 C and higher temperatures. Where a value such as 2H2O, 120 is given, it indicates a loss of 2 mol of water per formula weight of the compound at a temperature of 120 C. Boiling Point is given at atmospheric pressure (760 mmHg) unless otherwise indicated; thus 8215 mm indicates that the boiling point is 82 C when the pressure is 15 mmHg. Also, subl 550 indicates that the compound sublimes at 550 C. Flash Point is given in degrees Celsius, usually closed up. Because values will vary with the specific procedure employed, and sometimes the method was not stated, the values listed for the flash point should be considered only as indicative. See also Table 4.13, Properties of Combustible Mixtures in Air. Solubility is given in parts by weight (of the formula weight) per 100 parts by weight of the solvent and at room temperature. Other temperatures are indicated by the superscript. In the case of gases, the solubility is often expressed as 510 mL, which indicates that at 10 C, 5 mL of the gas is soluble in 100 g of the solvent. Abbreviations Used in the Table abs, absolute

EtOH, ethanol, 95%

s, soluble

acet, acetone

expl, explodes

sec, secondary

alc, ethanol

glyc, glycerol

sl, slight or slightly

alk, alkali (i.e., aqueous NaOH

h, hot

soln, solution

HOAc, acetic acid

solv, solvent

or KOH) anhyd, anhydrous

hyd, hydrolysis

subl, sublimes

aq, aqueous; water

hygr, hygroscopic

s, symmetrical

as, asymmetrical

i, insoluble

sym, symmetrical

atm, atmosphere

ign, ignites

tert, tertiary

BuOH, butanol

i-PrOH, isopropanol

v, very

bz, benzene

l (), levorotatory

v s, very soluble

c, cold

L, designates configuration

v sl s, very slightly soluble

chl, chloroform, CHCl3

m, meta position

vac, vacuo or vacuum

conc, concentrated

Me, methyl

vols, volumes

d, decomposes or decomposed

MeEtKe, methyl ethyl ketone

, greater than

d (), dextrorotatory

MeOH, methanol

, less than

dn, deuterium substitution

misc, miscible; soluble in all

D, designates configuration deliq, deliquescent dil, dilute

proportions NaOH, aqueous sodium hydroxide

~, approximately , alpha position , beta position , gamma position , delta position

diox, dioxane

o, ortho position

DL (or dl), inactive (i.e., 50% D

org, organic

, epsilon position

p, para position

, omega position (farthest

and 50% L) DMF, dimethylformamide

PE, petroleum ether

EtAc, ethyl acetate

pyr, pyridine

eth, diethyl ether

from parent functional group)

1.82

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

a1

()-Abietic acid

302.44

92, 424

—

172–175

a2 a3 a4 a5 a6

Acenaphthene Acenaphthlyene Acetaldehyde Acetaldoxime Acetamide

CH3CHO CH3CH ¨ NOH CH3CONH2

154.21 152.20 44.05 59.07 59.07

5, 586 5, 625 1, 594 1, 608 22, 177

1.06995 95 0.89916 4 0.805304 1.331120 0.966 1.41520 0.9711112 1.4158110

93.45 80–83 123.5 46.5 80.1

a7

Acetamidine HCl

CH3(¨NH)NH2 · HCl

94.54

2, 185

a8

N-(2-Acetamido)2-aminoethanesulfonic acid 4-Acetamidobenzaldehyde 4-Acetamidobenzenesulfonyl chloride 2-Acetamidobenzoic acid 4-Acetamidobenzoic acid 2-Acetamidofluorene N-(2-Acetamido)iminodiacetic acid 2-Acetamidophenol 3-Acetamidophenol 4-Acetamidophenol

H2N(CO)CH2NHCH2CH2SO3H

182.20

CH3CONHC6H4CHO

163.18

14, 38

154–156

s aq, bz; sl s alc

CH3CONHC6H4SO2Cl

233.67

14, 439

149

d aq; v s alc, eth

CH3CONHC6H4COOH

179.18

14, 337

185–187

CH3CONHC6H4COOH

179.18

14, 432

260–262

sl s aq; v s alc, bz, eth, acet i aq; s alc; sl s eth

223.28 190.16

12, 1331

H2NCOCH2N(CH2COOH)2

194 219 d

CH3CONHC6H4OH CH3CONHC6H4OH CH3CONHC6H4OH

151.17 151.17 151.17

13, 370 13, 415 13, 460

207–209 146–149 170

a9 a10 a11 a12 a13 a14 a15 a16 a17

170–172

279 280 20.2 114.5 221.15

27 38

i aq; s alc, bz, chl, eth, acet, dil alk i aq; 3.2 alc; 20 bz i aq; v s alc, eth misc aq, alc v s aq, alc; eth 70 aq; 50 alc; s chl, hot bz v s aq, alc; i acet, eth

 220 d

1.29321 4

i aq; s alc, glycols

s alc, acet

a18

Acetanilide

CH3CONHC6H5

a19

Acetic acid

CH3COOH

60.65

a20

Acetic acid-d

CH3COOD

61.05

a21 a22 a23 a24

Acetic-d3, acid-d Acetic anhydride Acetic anhydride-d6 Acetoacetic acid

CD3COOD (CH3CO)2O (CD3CO)2O CH3COCH2COOH

a25 a26 a27 a28

Acetohydrazide Acetone Acetone-d6 Acetone oxime

CH3CONHNH2 CH3COCH3 CD3COCD3 (CH3)2C ¨ NOH

ACES, a8 Acetal, d251 Acetaldehyde ammonia, a163 Acetaldehyde diethyl acetal, d251 Acetaldehyde dimethyl acetal, d438 Acetamidoacetic acid, a46 2-Acetamidopentanedioic acid, a45

135.17

64.08 102.09 108.14 102.09 74.08 58.08 64.13 73.10

Acethydrazide, a25 Acetic acid hydrazide, a25 Acetoacetanilide, a32 2-Acetoacetanisidide, a302 4-Acetoacetanisidide, a303 Acetoacetic esters, e53, e54 Acetoin, h106

12, 237

1.21915 4

2, 96

1.049220 4

1.371620

1.07

1.371520

1.11 1.08215 4

1.370920 1.390420 1.387520

2, 166 3, 630 2, 191 1, 635 1, 649

114.2

304

173

16.63

117.90

40

115.5

40

⫺73.1 36–37

0.790820 4 0.88 0.901

1.358820 1.355420

⫺95.35 60–63

115.5 40 140.0 130 6565mm 54 d violently 100 12918mm 56.24 ⫺20 55.5 ⫺17 135

Acetonaphthones, m311, m312 Acetonecarboxylic acid, a24 Acetone cyanohydrin, h145 Acetone dimethyl acetal, d452 Acetone dimethyl acetal, d452 Acetone ketal of glycerine, d515

0.56 aq25; 29 alc; 2bz; 27 chl; 25 acet; 5 eth misc aq, alc, eth, CCl4 misc aq, alc, eth, CCl4 misc aq, alc, eth 13 aq; s chl, eth d aq, alc misc aq, alc, eth

misc aq, alc, chl, v s aq, alc, eth

1.83

1.84

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference 2, 183

Density

Refractive index

Melting point

0.785720 0.84 1.023825

1.344120 1.342020 1.532225

43.8

a29 a30 a31 a32

Acetonitrile Acetonitrile-d3 Acetophenone 2-Acetylacetanilide

CH3CN CD3CN C6H5COCH3 C6H5NHCOCH2COCH3

41.05 44.08 120.15 177.20

7, 271 12, 518

a33

CH3COC6H4SO3Na

222.02

112, 186

a34 a35

4-Acetylbenzenesulfonic acid, Na salt 4-Acetylbiphenyl Acetyl bromide

C6H5C6H4COCH3 CH3COBr

196.25 122.95

72, 337 2, 174

1.66316 4

a36 a37

2-Acetylbutyrolactone Acetyl chloride

CH3COCl

128.13 78.50

2, 173

1.184620 4 1.10420 4

a38

Acetylcholine bromide Acetylcholine chloride 2-Acetylcyclopentanone Acetylene

(CH3)3NBrCH2CH2 ˆ OCOCH3 (CH3)3NClCH2CH2 ˆ OCOCH3

226.14

41, 428

114–116

181.66

4, 281

150–152

126.16

7, 558

1.043

HC ˜ CH

26.02

1, 228

0.90(g)

Acetylenedicarboxylic acid Acetyl fluoride

HOOCC ˜ CCOOH

114.06

2, 801

CH3COF

62.04

2, 172

a39 a40 a41

a42 a43

19.62 85

Boiling point 81.60 80.7 202.08

Flash point 5 5 82

Solubility in 100 parts solvent misc aq, alc, chl misc aq, alc, chl 0.55 aq; s alc, eth sl s aq; s alc, hot bz, chl, eth, acids, alk

300

116–118 325–327 96 75–77 1.458520 1.388620

112.9

1.490520

1075mm 50.8

4

i aq; v s alc, acet d aq, alc; misc bz, chl, eth 21 aq d aq, alc; misc bz, chl, eth v s aq (d hot aq); s alc; i eth v s aq; alc; d hot aq; i eth

72–7580mm 72 81891mm 83.95 subl

180 d 1.032

1

60

20

90 aq; 14 alc; v s bz, eth; acet dissolves 25 acet15° v s aq, alc, eth 5 aq(d); misc alc, bz, eth

a44 a45 a46 a47 a48 a49 a50 a51 a52

2-Acetylfuran N-Acetyl-Lglutamic acid N-Acetylglycine N-Acetylimidazole Acetyl iodide Acetyl-2-methylcholine chloride 2-Acetylphenothiazine 2-Acetylphenylacetonitrile N-Acetyl4-piperidone

Acetonylacetone, h61 Acetophenetidin, e45 Acetophenetidide, e45 p-Acetotoluide, m355 Acetoxime, a28 2-Acetoxybenzoic acid, a56 1-Acetoxy-1,3-butadiene, b375

HOOCCH2CH2CHˆ (NHCOCH3)COOH CH3CONHCH2COOH

CH3COI CH3COOCH(CH3)CH2 NC1(CH3)3 C6H5CH(CN)COCH3

110.11 189.17

17, 286 42, 908

117.10

4, 354

110.12 169.96 195.69

2, 174

241.31 159.19

1.098

1.506520

29–30 6710mm 200–201

71

2.7 aq15; s alc; i eth

207–209 93–96 2.067420 4

1.549120

108

d aq, alc; s bz, eth v s aq, alc, chl; i eth

171–173 180–185 89–92

10, 699

141.17

Aceturic acid, a46 Acetylacetaldehyde dimethyl acetal, d435 Acetylacetone, p31 N-Acetylanthranilic acid, a11 Acetylbenzene, a31 Acetylcyclopropane, c368 Acetylene dichlorides, d179, d180

1.146

1.502620

218

⬎ 112

Acetylene tetrabromide, t9 Acetylene tetrachloride, t28 N-Acetylethanolamine, h115 3-Acetyl-6-methyl-2H-pyran-2,4-(3H)-dione, d21 2-(Acetyloxy)benzoic acid, a56 3-Acetyl-1-propanol, h157

1.85

1.86

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

188–189 220

112 150

212

112

a53 a54

2-Acetylpyridine 3-Acetylpyridine

(C5H4N)COCH3 (C5H4N)COCH3

121.14 131.14

21, 279 21, 279

1.080 1.102

1.520320 1.533620

a55 a56

4-Acetylpyridine Acetylsalicyclic acid

(C5H4N)COCH3 HOOCC6H4OOCCH3

121.14 180.16

21, 279 10, 67

1.095 1.35

1.529020

a57

2-Acetylthiophene

(C4H3S)COCH3

126.18

17, 287

1.16822 4

1.556420

a58

N-Acetylthiourea

CH3CONHC(S)NH2

118.16

3, 191

165–169

a59

246.27

222, 469

204–206

366.33

162, 127

a61

N-Acetyl-DLtryptophan Acid alizarin violet N Acridine

179.22

20, 459

a62

Acrylamide

H2C ¨ CHCONH2

71.08

2, 400

1.12230 4

a63

Acrylic acid

H2C ¨ CHCOOH

72.06

2, 397

1.051120

1.422420

13

140–141

54

a64

Acrylonitrile

H2C ¨ CHCN

53.06

2, 400

0.806020 4

1.391120

83.7

77.4

0

a65 a66 a67

Acryloyl chloride 1-Adamantanamine Adamantane

H2C ¨ CHCOCI

90.51 151.25 136.24

2, 400

1.114

1.435020

1.09

1.568

72–76 206–208 268 subl 205 sealed tube

a60

v s alc, eth v s acids, alc, eth; s aq 0.33 aq25; 20 alc; 5.9 chl; 5 eth; sl s bz sl s aq; misc alc, eth s hot aq, alc; sl s eth s aq, alc; v s eth

135

10–11

Solubility in 100 parts solvent

214

107–110 346 subl 110 84.5 12525mm

s alc, eth, CS2, PE

16

215 aq30; 86 alc30; 63 acet; 2.7 chl; v s eth misc aq, alc, bz, eth, chl, acet 7.3 aq; misc org solv d aq; v s chl sl s aq

a68 a69

1-Adamantanecarboxylic acid Adenine

135.13

26, 420

⬎360 d

a70

Adenosine

267.25

31, 27

234–236

N-Acetylsulfanilyl chloride, a10 Aconitic acid, p207 Acrolein, p204

180.25

Acrolein diethyl acetal, d258 Acrolein dimethyl acetal, d454 Acrylaldehyde, p207

174–175 subl 220

1-Adamantanemethylamine, a209 Adenosine monophosphate, a72

0.05 aq; sl s alc; i chl, eth s aq; i alc

1.87

1.88

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a71

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

a73 a74

Adenosine-5-diphosphoric acid Adenosine-5phosphoric acid D--Alanine DL--Alanine

CH3CH(NH2)COOH CH3CH(NH2)COOH

89.09 89.09

4, 385 4, 387

a75

L--Alanine

CH3CH(NH2)COOH

89.09

4, 381

a76 a77 a78 a79

-Alanine Allantoin Allene Alloxan monohydrate

H2NCH2CH2COOH

89.09 158.12 40.06 160.09

4, 401 25, 474 1, 248 24, 500

a80 a81

Allyl acetate Allyl alcohol

H2C ¨ CHCH2OCOCH3 H2C ¨ CHCH2OH

100.12 58.08

2, 136 2, 436

1.404020 0.9280.928 4 1.412720 0.854020 4

a82

Allylamine

H2C ¨ CHCH2NH2

57.10

4, 205

0.76020 20

1.420520

a83 a84 a85 a86

N-Allylaniline Allylbenzene Allyl bromide Allylchlorodimethylsilane Allyl chloroformate

C6H5NHCH2CH ¨ CH2 C6H5CH2CH ¨ CH2 H2C ¨ CHCH2Br H2C ¨ CHCH2Si(CH3)2C1 H2C ¨ CHCH2OOCC1

133.19 118.18 120.98 134.7

12, 170 5, 484 1, 201

0.98225 0.89220 0 1.45125 25 0.89642

1.563020 1.512220 1.46525 1.419520

1.13

1.423

a72

a87

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

427.22 347.22

H2C ¨ C ¨ CH2

120.54

200 d

v s hot aq, HC1

291–293 d 289 d subl

1.402

16.7 aq25; 8.7 alc25; i eth 16.7 aq25; 8.7 alc25; i eth v s aq; sl s alc; i eth 0.45 aq; 0.2 alc

315–316 1.4375 1.787

1.4168

197–198 d 238 136.2 34.5 253 d

50 glass 88.2

50

104 97.1

6 22

53.3

28

218–220 156–157 70 110–112

89 33 7

27

31

s alc, acet, HOAc; sl s chl, PE, EtAc i aq; misc alc, eth misc aq, alc, chl, eth misc aq, alc, chl, eth i aq; s alc, eth i aq; s alc, eth i aq; misc org solv

a88 a89 a90 a91 a92

Allylcyclohexylamine Allyldichloromethylsilane N-Allyl-N,Ndimethylamine Allyl ethyl ether Allyl iodide

C6H11NHCH2CH ¨ CH2 H2C ¨ CHCH2Si(CH3)Cl2 H2C ¨ CHCH2N(CH3)2 H2C ¨ CHCH2OCH2CH3 H2C ¨ CHCH2I

Adenosine 5⬘-(trihydrogen diphosphate), a71 5⬘-Adenylic acid, a72 Adipic acid, h57 Adipic acid monoethyl ester, e149 Adiponitrile, d238 Adipolyl chloride, h62 ADP, a71

139.24 155.1

0.962 1.075820

85.0 86.13 167.98

Alaninols, a271, a272 Alizarin, d371 Allylacetic acid, p50 Allylacetone, h78 4-Allylanisole, a94 Allyl carbamide, a105 Allyl chloride, c216

1, 438 1, 202

0.765120 4 1.84620 4

1.466420 1.441920

6612mm 119–120

1.401020

63–64

1.388120 ⫺99.3

53

64–66 103.1

Allyl cyanide, b400 Allyldimethylchlorosilane, a86 Allyl glycidyl ether, a96 1-Allyl-2-hydroxybenzene, a98 Allyl iodide, i50

i aq; misc alc, eth i aq; misc alc, eth

1.89

1.90

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

99.16

4, 214

1.01320 4

1.530020

80

Boiling point

a93

Allyl isothiocyanate

H2C ¨ CHCH2NCS

a94

H2C ¨ CHCH2C6H4OCH3

148.21

6, 571

0.964521 4

1.519520

215–216

H2C ¨ CHCH2SCH3 H2C ˆCHCH2OCH2 O CH ¨ CH2 H2C ¨ CHCH2OSi(CH3)3

88.17 114.14

1, 440

0.803 0.962

1.471420 1.433220

91–93 154

130.3

0.7830

1.407525

100–101

a98 a99

1-Allyl-4methoxybenzene Allyl methyl sulfide 1-Allyloxy2,3-epoxypropane Allyloxytrimethylsilane 2-Allylphenol Allyl phenyl ether

H2C ¨ CHCH2C6H4OH H2C ¨ CHCH2OC6H5

134.18 134.18

6, 572 6, 144

1.025515 15 0.98315 4

1.545520 1.520020

a100 a101

Allyl propyl ether 1-Allyl-2-thiourea

H2C ¨ CHCH2OC3H7 H2C ¨ CHCH2NHC(S)NH2

100.16 116.18

13, 1882 4, 211

0.767020 4 1.21920 20

1.391920

a102 a103

Allyltrichlorosilane Allyltriethoxysilane

175.5 204.3

1.201120 4 0.903020

1.446020 1.407220

a104 a105 a106 a107

Allyltrimethylsilane Allylurea Aminoacetonitrile Aminoacetonitrile hydrogen sulphate 2-Aminoacetophenone 3-Aminoacetophenone 4-Aminoacetophenone

H2C ¨ CHCH2SiCl3 H2C ¨ CHCH2Si(OC2H5)3 H2C ¨ CHCH2Si(CH3)3 H2C ¨ CHCH2NHCONH2 H2NCH2CN H2NCH2CN · H2SO4

114.27 100.12 56.07 154.14

0.719320 4

1.407420

4, 209 4, 344 4, 344

H2NC6H4COCH3

135.17

14, 41

H2NC6H4COCH3

135.17

14, 45

98–99

289–290

H2NC6H4COCH3

135.17

14, 46

106

293–295

a95 a96 a97

a108 a109 a110

6

150

Flash point 46

Solubility in 100 parts solvent 0.2 aq; misc org solv a slc, chl

18 57

220 192

88 62

90–92

38

78

s alc, eth i aq; s alc; misc eth s alc; misc eth 3.3 aq; s alc; i bz; v sl s eth

117.5 176740mm 85–86 78 101

7

5815mm d d 165

v s aq, alc; v sl s eth s acids, alc v s aq; sl s alc; i eth

703mm

v sl s aq; s alc, eth

s hot aq, alc, eth, HOAc; sl s bz

a111

1-Aminoanthraquinone

223.23

14, 177

253–255 subl

a112

223.23

14, 191

295 d

a113

2-Aminoanthraquinone 4-Aminoantipyrine

203.25

24, 273

109

a114

2-Aminobenzamide

H2NC6H4CONH2

136.15

14, 320

110

H2NC6H4AsO(OH)2

217.06

161, 463

153

H2NC6H4AsO(OH)2

217.06

16, 878

⬎ 300

H2NC6H3(COOH)2

181.15

141, 636

⬎ 300

H2NC6H3(SO3H)2

253.24

H2NC6H4SO3H

173.19

14, 681

d 325

a115

2-Aminobenzenearsonic acid a116 4-Aminobenzenearsonic acid a116a 5-Aminobenzene-1,3dicarboxylic acid a117 2-Aminobenzene-1,4disulfonic acid a118 2-Aminobenzenesulfonic acid Allyl mercaptan, p206 4-Allyl-2-methoxyphenol, m99 2-Allyl-4-methylphenol, m387 2-Allyl-6-methylphenol, m386

Allyl sulfide, d27 Aluminon, a316 N-Amidinosarcosine, c277 Aminoacetaldehyde diethyl acetal, d254

subl

300 sl d

i aq; v s alc, bz, chl, eth, HOAc, HCl i aq, eth; s alc, bz s aq, alc, bz; sl s eth v s hot aq, alc; i bz; sl s eth

s hot aq, alk CO3, mineral acids

1.5 aq15; v sl s alc, eth

Aminoacetaldehyde dimethyl acetal, d440 1-Aminoadamantane, a66 Aminoanisoles, m42, m43, m44 p-Aminoazobenzene, p87

1.91

1.92

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a119

Name

a121 a122

3-Aminobenzenesulfonic acid 4-Aminobenzenesulfonic acid 2-Aminobenzoic acid 3-Aminobenzoic acid

a123 a124 a125 a126 a127

a120

a128 a129 a130 a131 a132 a133 a134 a135 a136

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

2 aq15; sl s alc

H2NC6H4SO3H

173.19

1.69

H2NC6H4SO3H

173.19

14, 695

H2NC6H4COOH H2NC6H4COOH

137.14 137.14

14, 310 14, 383

4-Aminobenzoic acid 2-Aminobenzonitrile 3-Aminobenzonitrile

H2NC6H4COOH H2NC6H4CN H2NC6H4CN

137.14 118.14 118.14

14, 418 14, 322 14, 391

4-Aminobenzonitrile 2-Aminobenzophenone 2-Aminobenzothiazole 2-Aminobenzotrifluoride 3-Aminobenzotrifluoride 4-Aminobenzotrifluoride N-(p-Aminobenzoyl)glycine 4-Aminobenzoyl hydrazide 2-Aminobiphenyl 4-Aminobiphenyl D-()-2-Amino-1butanol

H2NC6H4CN H2NC6H4COC6H5

118.14 197.24

14, 425 14, 76

H2NC6H4CF3

150.20 161.13

27, 182 122, 453

1.29025

H2NC6H4CF3

161.13

12, 870

H2NC6H4CF3

161.13

123, 2151

H2NC6H4CONHCH2COOH

194.19

142, 258

198–199

H2NC6H4CONHNH2

151.17

141, 570

227

H2NC6H4C6H5 H2NC6H4C6H5 CH3CH2CH(NH2)CH2OH

169.23 169.23 89.14

12, 1317 12, 1318 4, 291

53 54 2

1 aq20; sl s hot MeOH v s hot aq, alc, eth sl s aq; v s alc; s eth 0.59 aq; 5.6 alc s alc, eth s hot aq; v s alc, eth v s hot aq, alc, eth sl s aq; s alc, eth

d 288 144–146 subl 172–174

1.5114 1.374

187 49 53

268 288–290

85 108

d 223–226

1.478525

132 34

d 175

55

1.290

1.480020

6

187

85

1.28327

1.481525

38

10739mm

85

0.94720

Solubility in 100 parts solvent

1.452120

v s alc, chl, eth

i aq; s alc, bz, chl

299 19115mm 174

79

sl s aq; s alc s hot aq, alc, eth misc aq; s alc

a137 a138 a139 a140 a141 a142 a143 a144 a145 a146

L-(⫺)-2-Amino-1-

butanol DL-2-Aminobutyric acid 4-Aminobutyric acid 2-Amino-4-chlorobenzoic acid 2-Amino-5-chlorobenzonitrile 2-Amino-4⬘-chlorobenzophenone 2-Amino-5-chlorobenzophenone 2-Amino-5-chlorobenzotrifluoride 3-Amino-4-chlorobenzotrifluoride 5-Amino-2-chlorobenzotrifluoride

⫺2

174

4, 408

304

subl 300

4, 413 14, 365

195.d 233

0.94720

1.452520

CH3CH2CH(NH2)CH2OH

89.14

4, 291

CH3CH2CH(NH2)COOH

103.12

H2NCH2CH2CH2COOH H2N(Cl)C6H3COOH

103.12 171.58

H2N(Cl)C6H3CN

152.58

H2NC6H4COC6H4Cl

231.68

141, 389

104

H2N(Cl)C6H3COC6H5

231.68

14, 79

100

H2N(Cl)C6H3CF3

195.57

123, 1921

H2N(Cl)C6H3CF3

195.57

H2N(Cl)C6H3CF3

195.57

Aminobenzenethiol, a293 Aminobenzoic acid hydrazide, a133 Aminobenzyl cyanide, a260 1-Aminobutane, b417

99

misc aq; s alc 21 aq; 0.2 hot alc v s aq; i alc, eth

1320.5mm

1.386

1.506920

66–673mm

1.428

1.497525

82–839mm

2-Aminobutane, b377 Aminobutanoic acids, a138, a139 3-Amino-2-butenamide, a150 4-Aminobutyraldehyde diethyl acetal, d247

82

⬎112

none

36

␣-Aminocaproic acid, a183 ␧-Aminocaproic acid, a184

1.93

1.94

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a147

a148 a149 a150 a151 a152

a153

a154 a155 a156 a157 a158 a159 a160

Name 2-(3-Amino-4-chlorobenzoyl)benzoic acid 2-Amino-4-chlorophenol 2-Amino-5-chloropyridine 3-Aminocrotamide 3-Aminocrotononitrile 1-Amino-1-cyclohexanecarboxylic acid 5-Amino-2,3-dihydro1,4-phthalazinedione 2-Amino-4,6-dihydroxypyrimidine 4-Amino-2,6-dihydroxypyrimidine 4-Amino-3,5-diiodobenzoic acid 2-Amino-4,6-dimethylpyridine 4-Amino-2,6-dimethylpyridimide 6-Amino-1,3-dimethyluracil 5-Amino-2,6-dioxo1,2,3,6-tetrahydro4-pyrimidinecarboxylic acid

Formula weight

Beilstein reference

H2N(Cl)C6H3COC6H4COOH

275.69

14, 661

171–173

H2N(Cl)C6H3OH

143.57

13, 383

138

H2N(Cl)C5H3N

128.56

222, 332

138

CH3C(NH2) ¨ CHCONH2 CH3C(NH2) ¨ CHCN C6H10(NH2)COOH

100.12 82.11 143.19

3, 660 14, 299

300

177.16

251, 698

319–320

127.10

24, 468

300

127.10

24, 469

300

I2(NH2)C6H2COOH

388.93

14, 439

300

(CH3)2(NH2)(C5H2N)

122.17

22, 435

64

123.16

242, 45

181

155.16

24, 471

295 d

171.11

25, 264

300

Formula

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

12811mm

102

i aq, alc 235 156 aq; 18.9 alc

a161

2-Aminoethanesulfonic acid a162 2-Aminoethanethiol a163 1-Aminoethanol a164 2-Aminoethanol a165 2-(2-Aminoethoxy)ethanol a166 2-(2-Aminoethylamino)ethanol a167 5-(2-Aminoethylamino)-1-naphthalenesulfonic acid a167a 3-(2-Aminoethylamino)propyltrimethoxysilane

H2NCH2CH2SO3H

125.15

4, 528

d ⬎ 300

HSCH2CH2NH2 CH3CH(OH)NH2 H2NCH2CH2OH H2NCH2CH2OCH2CH2OH

77.14 61.08 61.08 105.14

4, 286 4, 274 43, 642

1.015820 1.460

1.453920

99–100 97 10.52

H2NCH2CH2NHCH2CH2OH H2NCH2CH2NHC10H6SO3H

104.15

4, 286

1.030

1.486120

H2NCH2CH2NHCH2CH2CH2Si(OCH3)3

222.1

4-Amino-m-cresol, a218 Aminocyclohexane, c334 Aminodecane, d19 2-Amino-2-deoxyglucose, g5 2-Amino-5-diethylaminopentane, d327

6.45 aq12; i abs alc

110 d 171 218–224

93

v s aq; s alc s aq; sl s eth misc aq, org solv

241

129

v s aq, alc; sl s eth

14015mm

150

⬎300

266.32 1.0125 4

2-Amino-1,5-dihydro-1-methyl-4 H-imidazol-4one, c278 2-Aminodiphenylamine, p131 1-Amino-1,2-diphenylethane, d668 Aminodiphenylmethane, d678

1.441825

Aminoethane, e58 1-(2-Aminoethyl)amino-2-[(2-aminoethyl)aminoethyl]aminoethane, t54

1.95

1.96

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a168 a169

a170 a171

a172 a173 a174 a175 a176 a177 a178 a179

a180

Name 3-Amino-9-ethylcarbazole 2-Aminoethyl hydrogen sulfate 3-(2-Aminoethyl)indole S-2-Aminoethylisothiouronium bromide HBr N-(2-Aminoethyl)morpholine p-(2-Aminoethyl)phenol N-(2-Aminoethyl)piperazine N-(2-Aminoethyl)1,3-propanediamine 2-Amino-2-ethyl-1,3propanediol 2-(2-Aminoethyl)pyridine 4-(2-Aminoethyl)pyridine 3-Amino-4fluorobenzotrifluoride Aminoguanidine H2CO3

Formula

H2NCH2CH2OSO3H

Formula weight

Beilstein reference

210.28

221, 642

98–100

141.15

4, 276

280 d

160.22

221, 636

118

Density

Refractive index

281.02

137.18

Boiling point

0.992

1.475520

1370.15mm

Solubility in 100 parts solvent

i aq, bz, chl, eth; s alc, acet

25.6

205

0.985

1.498320

26

222

H2NCH2CH2CH2NHCH2CH2NH2 HOCH2C(NH2) (C2H5)CH2OH H2NCH2CH2(C5H4N)

117.20

0.928

1.481520

119.16

1.09920 20

1.49020

1.021

1.535720

9312mm

H2NCH2CH2(C5H4N)

122.17

1.012

1.540320

1049mm

H2N(F)C6H3CF3

179.0

1.460820

8120mm

H2NNHC( ¨ NH) NH2 · H2CO3

136.11

22, 434

3, 117

175

161–163 1758mm

13, 625

129.21

122.17

Flash point

194–195

130.19 HOC6H4CH2CH2NH2

Melting point

93 96

38

172 d

15210mm

74

misc aq; s alc

i aq; d hot aq

a181 a182 a183 a184 a185 a186 a187

Aminoguanidine nitrate N-Aminohexamethyleneimine 2-Aminohexanoic acid 6-Aminohexanoic acid 6-Amino-1-hexanol 1-Amino-4-hydroxyanthraquinone L-2-Amino-3-hydroxybutyric acid

H2NNHC( ¨ NH)NH2 · HNO3 C6H12NˆNH2 CH3(CH2)3CH(NH2)COOH H2N(CH2)4CH2COOH H2N(CH2)5CH2OH

CH3CH(OH)CH(NH2)COOH

Aminoethylbenzenes, e64, e65 2-(2-Aminoethyl)-2-thiopseudourea, a171 1-Aminoheptane, h20

137.11

3, 117

114.19

0.984

1.485020

165

56

d 327

1.15 aq25; 0.42 alc

4, 434 42, 748 14, 268

204–206 56–58 13530mm 207–209

v s aq; i alc

4, 514

d 255– 257

v s aq; i alc, eth, chl

131.18

4, 433

131.18 117.19 239.23 119.12

2-Aminoheptane, m269a 1-Aminohexane, h80 2-Aminohexane, m353a

137

1.172

s eth

p-Aminohippuric acid, a132 Aminohydroxybenzoic acids, a286, a287

1.97

1.98

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

a188

DL-2-Amino-4-

a189 a190

a191

a192 a193

a194

a195

a196

a197 a198

Formula

HOCH2CH2CHhydroxy(NH2)COOH butyric acid L-2-Amino-4-hydroxyHOCH2CH2CHbutyric acid (NH2)COOH DL-4-Amino-3H2NCH2CH(OH)hydroxyCH2COOH butyric acid 4-Amino-6-hydroxy-2mercaptopyrimidine hydrate 2-Amino-4-hydroxy-6methylpyrimidine 4-Amino-3-hydroxy-1naphthalenesulfonic acid 4-Amino-5-hydroxyl-1naphthalenesulfonic acid 5-Amino-6-hydroxy-2naphthalenesulfonic acid 6-Amino-7-hydroxy-2naphthalenesulfonic acid 2-Amino-3-hydroxyH2N(HO)(C5H3N) pyridine 4-Amino-2-hydroxypyrimidine

Formula weight

Beilstein reference

119.12

4, 514

188–189

119.12

43, 1636

203 d

119.12

42, 938

202 d

161.18

24, 476

300

125.13

24, 343

300

239.25

14, 846

295 d

239.25

14, 835

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent s alc

s aq; sl s alc, eth

i aq, alc, bz, eth

sl s aq; i alc, eth

239.25

sl s hot aq; i eth

239.25

14, 849

300

110.12

222, 408

172–174

111.10

24, 314

 300

0.77 aq; sl s alc

a199 a200 a201 a202 a203 a204 a205

1-Aminoindan 5-Aminoindan 5-Aminoindazole 6-Aminoindazole 2-Amino-5-iodobenzoic acid DL-2-Amino-4-mercaptobutyric acid Aminomethanesulfonic acid

H2N(I)C6H3COOH HSCH2CH2CH(NH2)COOH H2NCH2SO3H

2-Amino-2-(hydroxymethyl)-1,3-propanediol, t423 -Amino-4-imidazolepropanoic acid, h83

1.03815 4

1.561320

133.19 133.19 133.15 133.15 263.03

12, 1191 121, 511 252, 308 25, 317 14, 373

135.19

43, 1647

232–233

111.12

1, 583

185 d

Aminoiminomethanesulfinic acid, f30 N-(Aminoiminomethyl)-N-methylglycine, c277 2-Aminoisobutyric acid, a222

1.5 36 178 206 d 221 d

978mm 249745mm

94

sl s aq sl s aq

sl s aq, PE; s alc

v s aq

5-Aminoisophthalic acid, a116a 6-Amino-2,4-lutidine, a157 2-Amino-3-mercaptopropanoic acid, c370

1.99

1.100

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a206 a207 a208 a209 a210 a211 a212 a213 a214 a215 a216 a217 a218 a219 a220

Name 3-Amino-4-methoxybenzoic acid 2-Amino-6-methoxybenzothiazole 5-Amino-2-methoxypyridine 1-(Aminomethyl)adamantane 4-(Aminomethyl)benzenesulfonamide 2-Amino-5-methylbenzoic acid 3-Amino-4-methylbenzoic acid DL-2-Amino-3-methyl1-butanol L-2-Amino-3-methyl1-butanol 2-(Aminomethyl)1-ethylpyrrolidine 2-Amino-3-methyl1-pentanol 2-Amino-4-methyl1-pentanol 4-Amino-3-methylphenol 4-(Aminomethyl)piperidine 2-Amino-2-methyl1,3-propanediol

Formula CH3O(NH2)C6H3COOH

CH3O(NH2)C5H3N

Formula weight

Beilstein reference

167.16

141, 657

241

180.23

272, 334

165–167

124.14

222, 408

165.28 H2NCH2C6H4SO2NH2

186.25

H2N(CH3)C6H3COOH

151.17

H2N(CH3)C6H3COOH

151.17

(CH3)2CHCH(NH2)CH2OH (CH3)2CHCH(NH2)CH2OH

103.17

CH3CH2CH(CH3)CH(NH2)CH2OH CH3CH(CH3)CH2CH(NH2)CH2OH H2N(CH3)C6H3OH

Refractive index

1.574520 0.933

Melting point

31

1.513720

Boiling point

Solubility in 100 parts solvent

901mm 83–850.3 mm 92 s dil alk, dil acid

14, 481

177 d

sl s aq; s alc, eth

14, 487

166

a aq

1.454320

778mm

83 78

103.17

0.926

1.454820

818mm

128.22

0.887

1.466520

6016mm

1.458920

117.19 117.19

4, 298

123.16

13, 593

105.14

Flash point

151–152

0.917

4, 303

30

1.451120

9714mm 200

90

25

200

78

110

15110mm

179 1.490020

114.19 HOCH2C(CH3)(NH2)CH2OH

Density

250 aq20; s alc

a221 a222

a223 a224 a225 a226 a227 a228 a229 a230

2-Amino-2-methyl1-propanol 2-Amino-2-methylpropionic acid 2-(Aminomethyl)pyridine 3-(Aminomethyl)pyridine 2-Amino-3-methylpyridine 2-Amino-4-methylpyridine 2-Amino-6-methylpyridine 2-Amino-4-methylpyrimidine 2-Amino-4-methylthiazole 2-Aminomethyl-3,5,5trimethylcyclohexanol

0.93420 20

1.448020

30–31

1.049

1.544520

335 280 subl sealed tube 8512mm

1.062

1.551020

21

741mm

1.578220

34

222

v s aq; s alc

222, 342

100

230

v s aq, alc, DMF

108.14

221, 633

45

209

v s aq

109.13

24, 84

160

subl

s hot aq; s alc

114.17

27, 159

45

232

v s aq, alc, eth

43–48

265

(CH3)2C(NH2)CH2OH

89.14

(CH3)2C(NH2)COOH

103.12

H2NCH2(C5H4N)

108.14

H2NCH2(C5H4N)

108.14

H2N(CH3)(C5H3N)

108.14

222, 342

H2N(CH3)(C5H3N)

108.14

H2N(CH3)(C5H3N)

1-Amino-2-methoxyethane, m69 -(Aminomethyl)benzyl alcohol, a262

171.29

4, 414

0.969

3-Amino--methylbenzyl alcohol, a261 2-Amino-3-methylpentanoic acid, i79

1.490420

165

67

misc aq; s alc, org solv v s aq

100

 112

2-Aminomethylthiophene, t158

1.101

1.102

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a231 a232

a233

a234

a235 a236 a237 a238 a239 a240 a241 a242 a243 a244

Name N-Aminomorpholine 2-Amino-1, 5-naphthalenedisulfonic acid 7-Amino-1,3-naphthalenedisulfonic acid 4-Amino-1-naphthalenesulfonic acid 4-Amino-1,8-naphthalimide 3-Amino-2-naphthol 2-Amino-4-nitrobenzoic acid 2-Amino-5-nitrobenzonitrile 2-Amino-5-nitrobenzophenone 2-Amino-6-nitrobenzothiazole 2-Amino-5-nitrobenzotrifluoride 4-Amino-3-nitrobenzotrifluoride 4-Amino-4-nitrodiphenylsulfide 2-Amino-4-nitrophenol

Formula

H2NC10H6SO3H

Formula weight

Beilstein reference

102.14 303.31

27, 8 14, 786

303.31

14, 784

Density

Refractive index

1.059

1.477220

Boiling point 168

Flash point

Solubility in 100 parts solvent

58

300 300 1.67025 4

223.26

Melting point

d

212.21

222, 452

360

H2NC10H6OH H2N(NO2)C6H3COOH

159.19 182.14

13, 685 14, 374

207 270 d

H2N(NO2)C6H3CN

163.14

142, 234

200–207

C6H5COC6H3(NH2)NO2

242.23

14, 79

166–168

195.20

272, 232

247–249

H2N(NO2)C6H3CF3

206.12

90–92

H2N(NO2)C6H3CF3

206.12

105–106

O2NC6H4SC6H4NH2

246.29

13, 534

142

O2N(NH2)C6H3OH

154.13

132, 192

145

0.031 aq; s dil alk

i aq; v s alc, eth

a245 a246

a247

a248 a249 a250

4-Amino-2-nitrophenol D-()-threo-2-Amino1-(p-nitrophenyl)1,3-propanediol 2-Amino-5-( p-nitrophenylsulfonyl)thiazole 2-Amino-5-nitropyridine 2-Amino-5-nitrothiazole exo-2-Aminonorbornane

1-Aminonaphthalene, n17

O2N(NH2)C6H3OH

154.13

HOCH2CH(NH2)CH(OH)C6H4NO2

212.21

163–165 163–165

285.30

222–226

H2N(C5H3N)NO2

139.11

13, 520

127

221, 631

145.14 111.19

0.938

1-Amino-2-naphthol-4-sulfonic acid, a193

1.480720

188

sl s aq, bz, eth

202 d

v sl s aq; 0.7 alc; 0.4 eth 4910mm

35

1-Amino-2-naphthol-6-sulfonic acid, a195

1.103

1.104

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a251 a252 a253 a254 a255 a256 a257 a258 a259 a260 a261 a262 a263

a264 a265 a266 a267 a268

Name 2-Aminopentane 3-Aminopentane DL-2-Aminopentanoic acid 5-Aminopentanoic acid 5-Amino-1-pentanol 2-Aminophenethyl alcohol 2-Aminophenol 3-Aminophenol 4-Aminophenol 4-Aminophenylacetonitrile 1-(3-Aminophenyl)ethanol 2-Amino-1-phenylethanol 1S,2S-()-2-Amino1-phenyl-1,3-propanediol L-2-Amino-3-phenyl1-propanol 3-Amino-1-phenyl2-pyrazolin-5-one N-Aminophthalimide N-Aminopiperidine 3-Amino-1,2-propanediol

Formula weight

Beilstein reference

H(CH2)3CH(NH2)CH3 C2H5CH(NH2)C2H5 H(CH2)3CH(NH2)COOH

87.17 87.17 117.15

4, 177 4, 178 4, 416

H2N(CH2)4COOH

117.15

4, 418

H2N(CH2)5OH H2NC6H4CH2CH2OH

103.17 137.18

41, 441 133, 1679

H2NC6H4OH

109.13

13, 354

170–174

H2NC6H4OH H2NC6H4OH H2NC6H4CH2CN

109.13 109.13 132.17

13, 401 13, 427 14, 457

122–123 16411mm 190 284 d 44 312

H2NC6H4CH(CH3)OH

137.18

133, 1654

68–71

C6H5CH(CH2NH2)OH

137.18

132, 361

56–57

C6H5CH(OH)CH(NH2)CH2OH

167.21

C6H5CH2CH(NH2)CH2OH

151.21

Formula

Density

Refractive index

0.73920 0.74920 4

1.404720 1.405520 303

H2NCH2CH(OH)CH2OH

Boiling point

Flash point

91–92 91 320 subl

1

12216mm 1484mm

65 112

158–161

1.045

1.461520 1.584920

37

133, 1757

16017mm

92–94

200–202 0.928 1.175

1.475020 1.492020

146730mm 265739mm

s aq, alc, eth, PE misc aq, alc, eth 5.5 aq18; v sl s alc, chl, eth, PE v s aq; sl s alc; i eth

v s aq; s alc

210–215

20, 89 4, 301

Solubility in 100 parts solvent

2 aq; 4.3 alc; v s eth; sl s bz 2.5 aq; v s alc, eth 0.65 aq; s alc, eth sl s hot aq; s alc

109–113

175.19 162.15 100.17 91.11

Melting point

36 112

a269 a270 a271 a272 a273 a274 a275

a276 a277 a278

DL-1-Amino-2-

propanol DL-2-Amino-1propanol L-2-Amino-1-propanol 3-Amino-1-propanol 2-Amino-1-propene1,1,3-tricarbonitrile 3-Aminopropionitrile 3-Aminopropyl(diethoxy)methylsilane N-(3-Aminopropyl)iminodiethanol N-(3-Aminopropyl)morpholine N-(3-Aminopropyl)-2pyrrolidinone

5-Aminoorotic acid, a160 1-Aminopentane, p53 4-Aminophenyl phenyl ether, p70 Aminophenyl sulfones, d36, d37

2

CH3CH(OH)CH2NH2

75.11

4, 289

0.973

1.448320

CH3CH(NH2)CH2OH

75.11

41, 432

0.943

1.449520

CH3CH(NH2)CH2OH H2NCH2CH2CH2OH NCC(CN) ¨ C(NH2)CH2CN H2NCH2CH2CN H2N(CH2)3Si(CH3)(OCH2CH3)2

75.11 75.11 132.13

41, 432 4, 288

0.965 0.982

1.449520 1.459820

70.09 191.4

0.91620 4

1.42720

185 85–888mm

162.23

0.1071

1.498020

1702mm

137

144.22

0.987220 20

1.476120

224

98

142.20

1.014

1.500020

120– 1231mm

112

H2N(CH2)3N(CH2CH2OH)2

3-Aminophthalhydrazide, a153 Aminopicolines, a225, a226, a227 1-Aminopropane, p220 2-Aminopropane, i88

160

73

173–176 176 12 188 171–173

15

s aq, alc; i eth v s aq, alc, eth

62 79

v s aq, alc, eth s aq, alc s aq

misc aq, alc, bz

3-Amino-1-propene, a82 N-(3-Aminopropyl)diethanolamine, a276

1.105

1.106

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a279

Name

a281 a282 a283

3-Aminopropyltriethoxysilane 3-Aminopropyltrimethoxysilane 2-Aminopyridine 3-Aminopyridine 4-Aminopyridine

a284 a285

2-Aminopyrimidine 4-Aminoquinaldine

a286

4-Aminosalicyclic acid

a287 a288

5-Aminosalicyclic acid 2-Amino-3-sulfopropionic acid 5-Amino-1,2,3,4-tetrazole hydrate 5-Amino-1,3,4-thiadiazole-2-thiol 2-Aminothiazole 2-Amino-2-thiazole 2-Aminothiophenol 6-Amino-3-toluenesulfonic acid 3-Amino-1,2,4triazole

a280

a289 a290 a291 a292 a293 a294 a295

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

H2N(CH2)3Si(OC2H5)3

221.37

0.950620 4

1.422520

217

96

H2N(CH2)3Si(OCH3)3

179.2

1.0125 4

1.42025

808mm

104

(C5H4N)NH2 (C5H4N)NH2 (C5H4N)NH2

94.12 94.12 94.12

22, 428 22, 431 22, 433

58.1 210.6 64 248 155–158 273

95.11 158.20

24, 80 22, 453

123–126 subl 169 333

H2NC6H3(OH)COOH

153.14

14, 579

147 d

H2NC6H3(OH)COOH HOOCCH(NH2)CH2SO3H

153.14 187.17

14, 579 4, 533

280 d 260 d

103.08

26, 403

204 d

133.20

27, 674

235 d

100.14 100.14 125.19 187.22

27, 155 27, 136 13, 397 14, 723

93 91–93 26 300

84.08

26, 137

H2NC6H4SH H2NC6H3(CH3)SO3H

1.640520

159

92

Solubility in 100 parts solvent

s aq, alc, bz, eth s aq, alc, bz, eth s aq, alc; sl s bz, eth v s aq sl s aq; v s alc, eth, acet; s hot bz 0.2 aq; 4.8 alc; s dil acid, alk sl s aq, alc; s acid v s aq

sl s aq, alc, eth 234

79 1 aq12; v s hot aq s aq, alc, chl

a296

a298

5-Amino-2,2,4-trimethyl-1-cyclopentanemethylamine 11-Aminoundecanoic acid Aniline

a299 a300

Aniline hydrochloride 2-Anilinoethanol

a301

3-Anilinopropionitrile

a297

156.27

H2N(CH2)10COOH

0.901

1.473320

201.31 12, 59

1.021720

1.585520

C6H4NH2 · HCl C6H5NHCH2CH2OH

129.59 137.18

12, 182

1.222 1.085

1.579320

C6H5NHCH2CH2CN

146.19

6-Aminopurine, a69 2-Amino-3-pyridinol, a197 Aminopyrimidinediols, a154, a155 2-Aminosuccinamic acid, a313 Aminosuccinic acid, a314 6-Amino-2-thiouracil, a191 -Amino-p-toluenesulfonamide, a210 2-Amino-1,1,3-tricyanopropene, a273 1-Aminotricyclo[3.3.1.13,7]decane, a66

97

5.98

184.40

70

198

193 150– 112 15210mm

190–192

93.13

C6H5NH2

221

Aminouracil, a155 2-Aminovaleric acid, a253 5-Aminovaleric acid, a254 Amyl compounds, see Pentyl Amyl alcohol, p37 act-Amyl alcohol, m153 sec-Amyl alcohol, p38 tert-Amyl alcohol, m154 tert-Amylamine, d601

3.5 aq25; s alc, CCl4, eth, acids 100 aq; v s alc sl s aq; v s alc, chl, eth

52–53

Amyl bromides, b322, b323 Amyl chloride, c191 Amyl iodide, i47 Amyl mercaptan, p35 Amyl methyl ketone, h15 Anethole, m97 Angelic acid, m162 Anilinesulfonic acids, a118, a119, a120 Aniline-2,5-disulfonic acid, a117

1.107

1.108

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a302 a303 a304

Name 1-(o-Anisidino)-1,3butanedione 1-(p-Anisidino)-1,3butanedione Anthracene

Formula CH3OC6H4NHCOCH2COCH3 CH3OC6H4NHCOCH2COCH3

Formula weight

Beilstein reference

207.23

131, 117

84–85

207.23

131, 177

115–117

178.23

5, 657

1.2527 4

216.3

340

1.4320 4

286

377

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

a305

9,10-Anthracenedione

208.22

7, 781

a306

9,10-Anthraquinone1,5-disulfonic acid disodium salt 9,10-Anthraquinone2,6-disulfonic acid disodium salt 9,10-Anthraquinone2-sulfonic acid Na salt Antipyrine

412.31

11, 340

300

i aq; 1.5 alc; 1.6 bz; 1.2 chl; 3.1 CS2 i aq; 0.44 alc; 0.26 bz; 0.61 chl; 0.11 eth s aq

412.31

11, 342

325

s aq

a307

a308

a309 a310 a311

L-()-Arabinose

a312

L-()-Ascorbic acid

a313

L-()-Asparagine

L-()-Arginine

hydrate

185

310.26

H2NC( ¨ NH)NH(CH2)3CH(NH2)COOH

24, 27

150.13 174.20

31, 32 4, 420

160–163 223 d

4, 484

190– 192 d 233–235

176.12 H2NCOCH2CH(NH2)COOH · H2O

1.088113 4

188.23

150.14

114

319174mm

100 aq; 77 alc; 100 chl; 2.3 eth 100 aq 17.6 aq; sl s alc 100 aq; 3.3 alc 3.6 aq28; s alk acids; i alc, bz, eth

a314

L-()-Aspartic acid

a315

Atropine

Anisaldehydes, m45, m46 Anisamide, m47 Anisic acids, m50, m51, m52 Anisidines, m42, m43, m44 Anisole, m48 p-Anisoyl chloride, m53

HOOCCH2CH(NH2)COOH

133.10

4, 472

289.38

21, 27

p-Anisyl alcohol, m54 Anthraflavic acid, d374 Anthranilamide, a114 Anthranilic acid, a121 Anthranionitrile, a124 9,10-Anthraquinone, a305

270 sealed tube 114–116

APDC, p271 Araboascorbic acid, i59 Aspirin, a56 Arsanilic acids, a115, a116

0.45 aq; i alc, eth

0.22 aq; s bz, dil acid

1.109

1.110

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. a316

Name

Formula

Formula weight

Beilstein reference

473.44

102, 775

225 d

127.19 197.32

21, 242

35–38 14810mm 150–153

Density

Refractive index

Melting point

Boiling point

Aurintricarboxylic acid, triammonium salt 2-Azacyclooctanone 2-Azacyclotridecanone Azidotrimethylsilane Azidotriphenylsilane 1-Aziridineethanol cis-Azobenzene

(CH3)3SiN3 (C6H5)3SiN3 (CH2)2 ¨ NCH2CH2OH C6H5N ¨ NC6H5

115.21 301.4 87.12 182.23

16, 8

a323

2,2-Azobis(2-methyl)propionitrile

(CH3)2C(CN)N ¨ NC(CN)(CH3)2

164.21

4, 563

a324 a325

Azodicarbonamide 4,4-Azoxydianisole

H2NCON ¨ NCONH2 CH3OC6H4N ¨ N(lO)C6H4OCH3

116.08 258.28

3, 123 16, 637

225 d 120

a326

Azulene

128.17

52, 432

100.5

b1

Barbituric acid

128.09

24, 467

b2 b3

Basic fuchsin Benzaldehyde

C6H5CHO

337.86 106.12

13, 765 7, 174

1.22 1.044720

248– 252 d d 186 26

178.9

b4

Benzamide

C6H5CONH2

121.14

9, 195

1.3414

127.2

288

b5

Benzanilide

C6H5CONHC6H5

197.24

12, 262

1.315

163.1

11710mm

b6

1,2-Benzanthracene

228.29

5, 718

a317 a318 a319 a320 a321 a322

0.868

1.414220

1.088 1.20

1.456020

95 83–84 68.3

Flash point

v s aq

95–96 1000.01mm 168 293

23 67 i aq; s alc, eth, HOAc 2 EtOH; 5 MeOH; can explode in acetone

107 d

1.545520

Solubility in 100 parts solvent

250 s hot aq, dil acid

155–157 437.6

62

0.3 aq; s alc, acids 0.3 aq; misc alc, eth 1.3 aq; 17 alc; 30 pyr i aq; 1.7 alc; sl s eth sl s hot alc; s most other org solv

b7 b8 b8a

2,3-Benzanthracene 7 H-Benz[de]anthracen-7-one Benzene

b9 b10

Benzene-d Benzene-d6

Azacyclopropane, e131 Azelaic acid, n95 Azelonitrile, n94 Aziridine, e131 Azobis(isobutyronitrile), a323

228.29 230.27

52, 628 7, 518

1.35

C6H6

78.11

5, 179

0.873725

1.497925

C6H5D C6D6

79.12 84.16

0.95

1.498020 1.497820

4,4-Azoxyanisole, a325 Barbitol, d280 Behenic acid, d716 Behenyl alcohol, d717 Benzalacetone, p96

341 170

subl

sl s most org solv 1.6 bz; 0.5 HOAc

5.53

80.10

11

80 79.1

11 11

Benzal bromide, d102 Benzalphthalide, b101 Benzanthrone, b8 Benzeneacetaldehyde, p76a

0.17 aq; s most org solv

1.111

1.112

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

b11 b12

Benzenearsonic acid Benzeneboronic acid

C6H5AsO(OH)2 C6H5B(OH)2

202.04 121.93

16, 868 16, 920

b13

1,4-Benzenedicarbaldehyde

C6H4(CHO)2

134.13

b14

1,3-Benzendicarbonyl dichloride 1,4-Benzenedicarbonyl dichloride 1,3-Benzenedicarboxylic acid 1,4-Benzendicarboxylic acid

C6H4(COCl)2

b15 b16 b17

b18 b19 b20 b21 b22 b23 b24

1,4-Benzenedimethanol Benzenehexacarboxylic acid Benzenesulfinic acid Benzenesulfonamide Benzenesulfonic acid Benzenesulfonyl chloride Benzenesulfonyl fluoride

Density

Refractive index

1.76025

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

7, 675

163 d 217 to the anhydride 114

248

203.02

9, 834

43–44

276

180

i aq; 6 bz; 17 acet; 2 eth; 14 diox; 46 MeOH 73 bz; 62 CCl4

C6H4(COCl)2

203.02

9, 844

81

266

180

37 bz; 9 CCl4

C6H4(COOH)2

166.13

9, 832

345–348 subl

C6H4(COOH)2

166.13

9, 841

C6H4(CH2OH)2

138.17

6, 919

subl without melting 115 1431mm

C6(COOH)6

342.17

9, 1008

286 d

C6H5S( ¨ O)OH

142.16

11, 2

85

100 d

C6H5SO2NH2 C6H5SO2OH C6H5SO2Cl

157.19 158.18 176.62

11, 39 11, 26 11, 34

1.384215 15

1.5518

152 50–51 14.5

177100mm

C6H5SO2F

160.16

112, 23

1.328620 4

1.493218

1.10017

2.5 aq; 2 alc 2.6 aq; 1.8 alc; 43 eth; s bz

H2O on standing in air

0.012 aq; v s alc, HOAc; i bz, PE v sl s aq, chl, eth; sl s alc; s alk 188

v s aq, alc, eth v s aq, alc

203–204

112

sl s aq; s alc, bz, eth i aq; sl s alc; s eth v s aq, alc; sl s bz i aq; s alc, eth s alc, eth

b25 b26 b27

b28

b29 b30 b31

Benzenesulfonyl hydrazide 1,2,4,5-Benzenetetracarboxylic acid 1,2,4,5-Benzenetetracarboxylic anhydride 1,2,3-Benzenetricarboxylic acid dihydrate 1,2,4-Benzenetricarboxylic acid 1,3,5-Benzenetricarboxylic acid 1,2,4-Benzenetricarboxylic anhydride

Benzeneazobenzene, a322 Benzenecarbonitrile, b51

C6H5SO2NHNH2

172.21

11, 52

101–103

flammable solid

C6H2(COOH)4

254.15

9, 997

276

1.5 aq; v s alc

218.12

19, 196

283–286 397–400

C6H3(COOH)3·2H2O

246.18

9, 976

192 d

sl s aq; v s eth

C6H3(COOH)3

210.14

9, 977

321 d

C6H3(COOH)3

210.14

9, 978

330

192.13

18, 468

161–164 24514mm

2.1 aq; 25.3 alc; 7.9 acet; v s eth sl s aq; v s alc; s eth 50 acet; 22 EtAc

Benzene-1,2-dicarboxylic acid, p167 Benzenemethanol, b78

Benzenethiol, t159

1.113

1.114

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b32

Name

b33

1,3,5-Benzenetricarboxylic trichloride Benzethonium chloride

b34 b35

Benzil Benzil--dioxime

b36 b37 b38 b39 b40

b41 b42

Benzilic acid Benzil monohydrazone Benzimidazole Benzo-15-crown-5 7,8-Benzo-1,3-diazaspiro-[4,5]decane2,4-dione 1,4-Benzodioxan 2,3-Benzofuran

b43 b44

Benzofurazan-1-oxide Benzoic acid

b45 b46 b47

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

C6H3(COCl)3

265.48

35–36

(CH3)3CCH2C(CH3)2C6H4OCH2CH2OCH2CH2N(CH3)2CH2C6H5Cl C6H5COCOC6H5 C6H5C( ¨ NOH)C( ¨ NOH)C6H5 (C6H5)2C(OH)COOH C6H5C( ¨ NNH2)COC6H5

448.10

164–166

210.23

7, 747

228.25 224.26 118.14 268.3 216.24

10, 342 71, 394 23, 131

1.2315 4

94.9

Boiling point

Flash point

v s aq; s alc, acet

346

i aq; s alc, eth s alk sl s aq; v s alc, eth

153 150–152 170.5 360 76–78 268–270

1036mm 175

1.080

69–71 122.4

132.510mm 121

9, 164

1.199

39–40

360

8, 165 8, 174

1.310020 4 1.101617 4

17, 54

1.142 1.072

C6H5COOH

136.11 122.13

271, 740 9, 92

Benzoic anhydride

(C6H5CO)2O

226.23

DL-Benzoin Benzoin ethyl ether

C6H5COCHOHC6H5 C6H5CH(OC2H5)COC6H5

212.25 240.30

1.548520 1.566020

sl s aq, eth; v s alc

18

136.15 118.14

1.572717

Solubility in 100 parts solvent

134–136 344 61 19520mm

87 i aq; misc bz, eth, PE 0.29 aq; 43 alc; 10 bz; 22 chl; 33 eth; 33 acet i aq; s alc, acet, chl, bz, HOAc s acet; 20 pyr s alc, bz, eth

b48 b49 b50

Benzoin isobutyl ether Benzoin methyl ether -Benzoinoxime

b51

Benzonitrile

b52

Benzo[def]phenanthrene Benzophenone

b53 b54

Benzophenone hydrazone

Benzhydrazide, b72 Benzhydrol, d677 Benzhydrylamine, d678 Benzhydryl bromide, b274 Benzidine, b136

C6H5CH[OCH2CH(CH3)2]COC6H5 C6H5CH(OCH3)COC6H5 C6H5CH(OH)C( ¨ NOH)C6H5 C6H5CN

268.36

0.985

226.28 227.26

8, 174 8, 175

1.127814 4

103.12

9, 275

1.000625

202.26

5, 693

1.27123

C6H5COC6H5

182.22

7, 411

1.110815 4

C6H5C( ¨ NNH2)C6H5

196.25

7, 417

2-Benzimidazolethiol, m15 1,3-Benzodiazole, b38 1,3,2-Benzodioxaborole, c21 1,3-Benzodioxole, m240 Benzofuroxan, b43

1.548520

1330.5mm

85

48 18915mm 151–152 1.525725

12.75

191.1

71

156

404

48.1

305

98

23055mm

Benzoglyoxaline, b38 Benzoic acid hydrazide, b72 o-Benzoic sulfimide, s1

v s alc, bz, eth sl s aq; s alc, NH4OH 0.2 aq; misc alc, bz, chl, eth i aq; s alc, eth i aq; 13.3 alc; 17 eth

1.115

1.116

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b55

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Boiling point

b57 b58 b59

3,3,4,4-Benzophenonetetracarboxylic dianhydride 1-Benzopyran-4(4H ) -one 1,2-Benzo[a]pyrene 4,5-Benzo[e]pyrene 1,4-Benzoquinone

b60 b61 b62

Benzothiazole Benzo[b]thiophene 1,2,3-Benzotriazole

b63 b64 b65 b66 b67

Benzoxazole 1-Benzoylacetone 2-Benzoylbenzoic acid Benzoyl bromide Benzoyl chloride

C6H5COCH2COCH3 C6H5COC6H4COOH C6H5COBr C6H5COCl

119.12 162.19 226.23 185.03 140.57

27, 42 7, 680 10, 747 9, 195 9, 182

1.546720 1.21120 4

1.552520

1.0

182 260 sl d 265 218–219 197.2

b68 b69

Benzoyl cyanide Benzoyl fluoride

C6H5COCN C6H5COF

131.13 124.11

10, 659 9, 181

1.140

1.496020

32 28

206 161

b70 b71

Benzoylformic acid N-Benzoylglycine

C6H5COCOOH C6H5CONHCH2COOH

150.13 179.18

10, 654 9, 225

69 178–179

b72

Benzoylhydrazine

C6H5CONHNH2

136.15

9, 319

117

b56

322.23

Melting point

146.15

O ¨ C6H4 ¨ O

Flash point

Solubility in 100 parts solvent

215–217

17, 327

55–57

252.32 252.32 108.10

495

7, 609

1.31820 4

179.3 182 115.7

135.19 134.20 119.13

1.24620 4 1.193740 1.238

1.637920 1.630240 1.642020

2 31.32 98.5

231 221 20415mm

112

17, 59 26, 38

1.5594

30 60 129

58

90 68

48

1.09060 60

i aq; s bz; sl s alc i aq sl s aq; s alc, eth, hot bz, alk (with d) sl s aq; v s alc, CS2 s alc, bz, chl, eth sl s aq; s alc, bz, chl sl s aq sl s aq; v s alc, eth sl s aq; v s alc, eth d aq, alc; misc eth d aq, alc; misc bz, CS2, eth i aq d hot aq; v s alc, eth 0.4 aq; 0.1 chl; 0.25 eth; sl s alc; i bz, PE

b73

C6H5COCH2CH2COOH

178.19

10, 696

116

b74 b75 b76 b77

3-Benzoylpropionic acid 2-Benzoylpyridine 3-Benzoylpyridine 4-Benzoylpyridine Benzyl acetate

C6H5CO(C5H4N) C6H5CO(C5H4N) C6H5CO(C5H4N) CH3COOCH2C6H5

183.21 183.21 183.21 150.18

21, 330 21, 331 21, 331 6, 435

1.051525

1.523220

44 40 71 51.5

317 307 315 215.5

150 150 150 102

b78

Benzyl alcohol

C6H5CH2OH

108.13

6, 428

1.041325

1.537125

15.3

205.45

100

b79 b80 b81

Benzylamine 2-Benzylaminoethanol (3-Benzylamino)propionitrile

C6H5CH2NH2 C6H5CH2NHCH2CH2OH C6H5CH2NHCH2CH2CN

107.16 151.21 160.22

12, 1013 12, 1040

0.98119 4 1.065

1.542420 1.543520 1.530820

10

185 15612mm

60 112

Benzoresorcinol, d386 2-Benzothiazolethiol, m17 Benzotrichloride, t248

Benzotrifluoride, t300 Benzoylamide, b4 Benzoylbenzene, b53

sl s aq; s alc

Benzoyl peroxide, d54 1,2-Benzphenanthrene, b6 Benzylaniline, p92

s alc, bz, eth s alc, bz, eth sl s aq; misc alc, eth 0.08 aq; misc alc, eth misc aq, alc, eth

1.117

1.118

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

1.11825 4

1.568121

106 19.4

b82 b83

N-Benzylbenzamide Benzyl benzoate

C6H5CONHCH2C6H5 C6H5COOCH2C6H5

211.26 212.25

9, 121

b84

2-Benzylbenzoic acid

C6H5CH2C6H4COOH

212.24

92, 471

b85 b86

Benzyl bromide Benzyl-tert-butanol

171.04 164.25

5, 306 6, 548

b87

Benzyl butyl1,2-phthalate Benzyl carbamate Benzyl chloride

C6H5CH2Br C6H5CH2CH2C(CH3)2OH C6H5CH2OOCC6H4COOC4H9 C6H5CH2OCONH2 C6H5CH2Cl

312.37 151.17 126.59

6, 437 5, 292

C6H5CH2OC(O)Cl C6H5CH2S(COCl)

170.60 186.5

6, 437

C6H5CH2SCH2CH(NH2)COOH C6H5CH2P(O)(OC2H5)2

211.28

6, 465

C6H5CH2N[(CH2)17CH3](CH3)2Cl·H2O

442.18

C6H5CH2OC2H5 C6H5CH2NHCHO C6H5CH2OOCH

136.20 135.17 136.15

12, 1043

C6H5CH2ONH2

123.16

6, 440

b88 b89 b90 b91 b92 b93 b94

b95 b96 b97 b98

Benzyl chloroformate Benzyl chlorothiol formate S-Benzyl-L-cysteine Benzyl diethyl phosphite Benzyldimethylstearylammonium chloride Benzyl ethyl ether N-Benzylformamide Benzyl formate O-Benzylhydroxylamine

Boiling point 323.5

147

198–199 14485mm

86 112

110–113 1.43822 0

1.575220 1.509020

3.9 33

1.11925 25

228.23

Flash point

Solubility in 100 parts solvent i aq; misc alc, chl, eth sl s aq; s alc, bz, chl, eth sl d aq

218

1.099320

1.539120

1.195 1.23730 4

1.519020 1.571130

87–89 43 to 48

220 d 179

73

10320mm 800.13mm

91 118

1102mm

112

i aq; v s alc; sl s eth i aq; misc alc, chl, eth d aq; s eth

214 d 1.076

1.493020

123, 2212

67–69

0.947820

1.495820

185.0

i aq; misc alc, eth

203

i aq; s alc; misc eth

60–61 1.08120 4

11930mm

b99 b100 b101 b102 b103 b104

b105 b106 b107 b108

Benzylidenemalononitrile N-Benzylidenemethylamine 3-Benzylidenephthalide 2-Benzyl-2-imidazoline HCl Benzylmethylamine 3-(N-Benzyl-Nmethylamino)-1,2propanediol Benzyl methyl sulfide 3-Benzyloxyaniline 3-Benzyloxybenzaldehyde 4-Benzyloxybenzaldehyde

Benzyl cyanide, p80 Benzyl disulfide, d57 N-Benzylethanolamine, b80

C6H5CH ¨ C(CN)2

154.17

9, 895

C6H5CH ¨ NCH3

119.17

7, 213

222.24

17, 376

83–85 0.967

1.552620

8018mm

112

102

196.68

174

C6H5CH2NHCH3 C6H5CH2N(CH3)CH2CH(OH)CH2OH

138.23 195.26

12, 1019

0.939 1.084

1.522420 1.534120

C6H5CH2SCH3 C6H5CH2OC6H4NH2 C6H5CH2OC6H4CHO

138.23 199.25 212.25

6, 453 13, 404 8, 73

1.015

1.562020

C6H5CH2OC6H4CHO

212.25

8, 73

Benzyl ether, d58 Benzylideneacetone, p96 Benzylideneacetophenone, d686

v s aq, alc; s chl; v sl s eth, EtAc 184.189 20630mm

77 112

195–198

73

63–67 56–58 73–74

Benzyl mercaptan, p128 Benzyl methyl ketone, p144 Benzyloxyamine, b98

1.119

1.120

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b109

Name

Formula

Formula weight

b123

4-Benzyloxybenzyl alcohol 2-Benzyloxyethanol 4-Benzyloxy-3-methoxybenzaldehyde 4-Benzyloxypropiophenone Benzyl phenyl sulfide 1-Benzylpiperazine 4-Benzylpiperidine 1-Benzyl-4-piperidone 2-Benzylpyridine 4-Benzylpyridine 1-Benzyl-2-pyrrolidinone (Benzylthio)acetic acid Benzyl thiocyanate Benzyltributylammonium chloride Benzyltrichlorosilane

b124

Benzyltriethoxysilane

C6H5CH2Si(OC2H5)3

254.40

b125

Benzyltriethylammonium chloride Benzyltrimethylammonium chloride

 C6H5CH2N(C2H5) 3 Cl

227.78

 C6H5CH2N(CH3) 3 Cl

185.70

b110 b111 b112 b113 b114 b115 b116 b117 b118 b119 b120 b121 b122

b126

C6H5CH2OC6H4CH2OH

214.26

C6H5CH2OCH2CH2OH C6H5CH2OC6H3(OCH3)CHO C6H5CH2OC6H4COC2H5

152.19 242.27

C6H5CH2SC6H5

200.30 176.26 175.28 189.26 169.23 169.23 175.23

C6H5CH2(C5H4N) C6H5CH2(C5H4N)

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

86–87 1.0720 20

255.9

129

0.4 aq

63–65

240.30

100–102 6, 454 20, 296 20, 425 20, 426

43 1.014 0.997 1.021 1.054 1.06120 0 1.095

C6H5CH2SCH2COOH

182.24

C6H5CH2SCN  C6H5CH2N(C4H9) 3 Cl

149.22 312.94

C6H5CH2SiCl3

225.57

1.28820 4 0.98620 4

19727mm

20

1.5467 1.537920 1.539920 1.578520 1.581820 1.552520

7 10

279 1347mm 276 287

112 112 112 125 115 112

i aq; sl s alc; s eth s aq, alc, eth

i aq; v s alc, eth s alc; v s eth

59–63 6, 460

43 155 d 1.52620

140– 142100mm 170– 17570mm 185 d

12, 1020

235

i aq; s alc; v s eth

b127 b128 b129 b130 b131

Benzyltrimethylsilane Betaine Bicyclo[2.2.1]hepta2,5-diene Bicyclo[2.2.1]-2heptene Bicyclo[2.2.1]-5heptene-2-carbaldehyde

Benzylphenol, h113 BES, b180 Betahistine, m121

C6H5CH2Si(CH3)3 

(CH3)3N CH2COO

0.893320

164.32 117.15

1.494120 d  310

4, 347

92.14

0.90920

1.470720

94.16 122.16

o,o-Bibenzoic acid, b137 Bibenzyl, d666 Bicine, b182

190–191

1.018

1.488320

20

89

21

160 aq; 55 MeOH; 6 alc i aq; s PE

46

96

15

s eth

67– 7012mm

51

Bicyclo[4.4.0]decane, d1, d2

1.121

1.122

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b132

b133 b134 b135 b136 b137 b138 b139 b140

b141 b142 b143 b144

Name Bicyclo[2.2.2]oct-7ene-2,3,5,6-tetracarboxylic-2,3,5,6-dianhydride Biguanide Biphenyl 4-Biphenylcarboxylic acid (1,1-Biphenyl)-4,4diamine (1,1-Biphenyl)-2,2dicarboxylic acid 4-Biphenylmethanol 4-Biphenylsulfonic acid 2-(4-Biphenylyl)5-(4-tertbutylphenyl)1,3,4-oxadiazole o-Biphenylyl glycidyl ether 2-(4-Biphenylyl)-5phenyloxazole 2,2-Bipyridinium chlorochromate 2,2-Bis[ p-(allyloxy)phenyl]propane

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

300

248.19

H2NC( ¨ NH)NHC( ¨ NH)NH2 C6H5 ˆ C6H5 C6H5C6H4COOH

101.11

3, 93

130

d 142

s aq, alc; i bz, eth

154.20 198.22

5, 578 9, 671

68.8 226

255.0 subl

13, 214

128

400740mm

242.23

9, 922

228–229

i aq; s alc, eth i aq; v s alc, eth; s bz 0.04 aq; s alc; 2 eth 0.06 aq; s org solv

H2NC6H4C6H4NH2

184.23

HOOCC6H4C6H4COOH C6H5C6H4CH2OH C6H5C6H4SO3H

184.24 234.26

62, 636

101 138

0.993970

1.58877

354.46

138

226.28

30–32

197.36

118

C5H4N ˆ C5H4NHCrClO3

292.64

H2C ¨ CHCH2OC6H4C(CH3)2C6H4OCH2CH ¨ CH2

308.42

1.022

1.563620

1200.1mm

112

b145

b146 b147

b148

N,N-Bis(3-aminopropyl)-ethylenediamine N,N-Bis(3-aminopropyl)piperazine N,N-Bis(3-aminopropyl)-1,3propanediamine 2,5-Bis(4-biphenylyl)oxazole

Bicyclo[4.3.0]nonane, h46 Biphenol, d387 Biphenylamines, a134, a135

H2N(CH2)3NHCH2CH2NH(CH2)3NH2

200.33 H2N(CH2)3NHCH2CH2CH2NH(CH2)3NH2

1180.2mm

174.29

232, 12

0.973

1.501520

15

98–1031mm

188.32

373.46

3-(o-Biphenylyloxy)-1,2-epoxypropane, b142 2,2-Bipyridine, d705 Bis(4-aminophenyl)ether, o61

1522mm

240

1,3-Bis(aminomethyl)cyclohexane, c314 1,2-Bis(benzylamino)ethane, d59

1.123

1.124

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b149 b150

b151

b152

b153 b154 b155 b156 b157 b158 b159 b160

Name Bis(2-bromoethyl) ether 1,3-Bis(bromoethyl)tetramethyldisiloxane Bis(2-butoxyethyl) ether 2,5-Bis(5-tert-butyl2-benzoxazolyl)thiophene Bis(sec-butyl) disulfide Bis(tert-butyl) disulfide Bis(carboxymethyl) trithiocarbonate 1,2-Bis(2-chloroethoxy)ethane Bis(2-chloroethoxy)methylsilane Bis(2-chloroethyl) ether Bis(2-chloroethyl)N-methylamine Bis(chloromethyl)dimethylsilane

Formula

Formula weight

Beilstein reference

Density

Refractive index

BrCH2CH2OCH2CH2Br

231.92

[BrCH2Si(CH3)2]2O

320.17

1.391820 4

1.471920

(C4H9OCH2CH2)2O

218.33

0.885320 20

1.423320

430.57

Melting point

Boiling point

Flash point

103– 10720 103– 10415mm 60.2

254.6

47

178.36

13, 1549

0.957

1.492020

164739mm

112

(CH3)3CSSC(CH3)3

178.36

1, 379

0.909

1.493020

204

79

HOOCCH2SC( ¨ S)SCH2COOH (ClCH2CH2OCH2 ˆ )2

226.29

3, 252

172–175

187.07

1.19720 4

1.4617

1088mm

203.1

1.164320 4

1.443120

95–9718mm

1.219220

1.457520

143.01

CH3N(CH2CH2Cl)2

156.07

(CH3)2Si(CH2Cl)2

157.12

0.3 aq; misc alc, eth, ketones, esters, CCl4

201

[CH3CH2CH(CH3)]2S2

H(CH3)Si(OCH2CH2Cl)2 ClCH2CH2OCH2CH2Cl

Solubility in 100 parts solvent

12, 335

1.11825 4 43, 1845

1.07520 4

1.460020

51.7

178.8

60

7510mm 160

55

i aq; s most org solv v sl s aq; misc most org solv

b161 b162

b163

b164 b165 b166 b167

b168

b169

Bis(2-chloro-1methyl)ethyl ether Bis(4-chlorophenoxy)acetic acid 2,2-Bis( p-chlorophenyl)-1,1-dichloroethane 1,1-Bis(4-chlorophenyl)ethanol Bis(4-chlorophenyl) sulfone Bis(4-chlorophenyl) sulfoxide 1,1-Bis( p-chlorophenyl)-2,2,2-trichloroethane 1,3-Bis(dichloromethyl)tetramethyldisiloxane N,N-Bis(2,2-diethoxyethyl)methylamine

1.112220 20

ClCH2CH(CH3)OCH(CH3)CH2Cl (ClC6H4O)2CHCOOH

171.07 313.14

142

(ClC6H4)2CHCHCl2

320.05

111

(ClC6H4)2C(OH)CH3

267.16

63, 3396

ClC6H4SO2C6H4Cl

287.16

6, 327

ClC6H4S(O)C6H4Cl

271.17

61, 149

(ClC6H4)2CHCCl3

354.49

[Cl2CH(CH3)2Si]2O

300.16

[(C2H5O)2CHCH2]2NCH3

263.38

Bis(3-tert-butyl-4-hydroxy-5-methylphenyl) sulfide, t144

187.3

85

69

v sl s aq; s org solv 25010mm

144 109

4, 311

Bis(2-cyanoethyl) ether, o63

i aq; 58 acet; 78 bz; 45 CCl4; v s pyr, diox

1.221320 4

1.466020

14940mm

0.945

1.425920

222244mm

60

1.125

1.126

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b170

b171

b172 b173 b174 b175

b176 b177

b178 b179 b180

b181

Formula weight

Beilstein reference

[(C2H5)2NC6H4]2C ¨ O

324.47

14, 98

95

[(CH3)2)NC6H4]2C( ¨ O)

268.36

14, 89

172–176 d 360

[(CH3)2N]2Si(CH3)2

146.3

[(CH3)2NCH2]2CHOH

146.23

[(CH3)2NC( ¨ S)S ˆ ]2

240.43

H 2C

202.25

Name 4,4-Bis(diethylamino)benzophenone 4,4-Bis(dimethylamino)benzophenone Bis(dimethylamino)dimethylsilane 1,3-Bis(dimethylamino)-2-propanol Bis(dimethylthiocarbamyl) disulfide 1,4-Bis(2,3-epoxypropoxy)butane Bis(2-ethoxyethyl) ether Bis(2-ethylhexyl) decanedioate Bis(2-ethylhexyl) hydrogen phosphate Bis(2-ethylhexyl) o-phthalate N,N-Bis(2-hydroxyethyl)-2-aminoethanesulfonic acid Bis(2-hydroxyethyl) ether

Formula

CHCH2O OCH2CH2 ˆ ]2 (C2H5OCH2CH2)2O CH3(CH2)3CH(C2H5)CH2OOC(CH2)8COOCH2CH(C2H5)(CH2)3CH3 [CH3(CH2)3CH(C2H5)CH2O]2P(O)OH [CH3(CH2)3CH(C2H5)CH2OOC]2C6H4 (HOC2H5)2NCH2CH2SO3H HOCH2CH2OCH2CH2OH

162.23

Refractive index

0.81022

1.43222

4, 290

0.897

1.442220

4, 76

1.29

12, 519

426.66

322.43

Density

14, 1786

390.57

98

Boiling point

Flash point

Solubility in 100 parts solvent

i aq; s alc, warm bz

128–129 112

155–156

s alc, eth; sl s bz, acet; i aq 16011mm

112

44.3

188.4

54

v s aq, alc, org solv

1.445020

60

20910mm

1.485920

50

384

207

0.01 aq

245

143

misc aq, alc, acet, eth

1.049

1.453520

0.90720 4

1.411020

1.911925 25

1.449625

0.965 0.984320

213.25

106.12

Melting point

152–154

1, 468

1.11820 20

1.446020

10.45

b182 b183

b184

b185

b186 b187 b188 b189 b190 b191

N,N-Bis(2-hydroxyethyl)glycine Bis(2-hydroxyethyl)iminotris(hydroxymethyl)methane 2,2-Bis(hydroxymethyl)propionic acid 4,8-Bis(hydroxymethyl)tricyclo[5.2.02,6]decane Bis(2-mercaptoethyl) ether Bis(2-mercaptoethyl) sulfide 1,4-Bis(methanesulfonoxy)butane 1,2-Bis(methoxyethoxy)ethane Bis[2,(2-methoxyethoxy)ethyl] ether Bis(2-methoxyethyl) ether

Bis(2-ethylhexyl) sebacate, b177 Bis(2-hydroxyethyl) sulfide, t149

(HOCH2CH2)2NCH2COOH

163.17

192 sl d

(HOCH2CH2)2NC(CH2OH)3

209.24

104

(HOCH2)2C(CH3)COOH

134.13

3, 401

189–191 112

1.528020

196.29

(HSCH2CH2)2O

138.25

1.114

(HSCH2CH2)2S

154.32

1.183

(CH3SO2OCH2CH2 ˆ )2

246.30

(CH3OCH2CH2OCH2 ˆ )2

178.23

(CH3OCH2CH2OCH2CH2 ˆ )2O (CH3OCH2CH2 ˆ )2O

222.28 134.18

sl s aq

80 1.598220

217 13610mm

90

115–117

13, 2107

0.99020 4

1.422420

45

216

110

sl hyd aq; 0.1 alc; 1.4 acet misc aq

1.008720 4

1.433020

27

275.3

140

s aq

0.944025

1.404325

68

162

70

misc aq

2,2-Bis(hydroxymethyl)-2,2,2 -nitrilotriethanol, b183

Bis(4-hydroxyphenyl) sulfide, t150

1.127

1.128

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b192 b193 b194 b195 b196

b197 b198 b199 b200 b201 b202

b203 b204 b205

Name Bis(2-methylallyl) carbonate Bis(4-nitrophenyl) carbonate Bis(3-nitrophenyl) disulfide Bis(4-nitrophenyl) disulfide Bis(octadecyl)pentaerythritol diphosphite Bis(pentabromophenyl) ether 1,4-Bis(5-phenyloxazol-2-yl)benzene Bis(p-tolyl) disulfide Bis(p-tolyl) sulfoxide Bis(tributyltin) oxide 1,4-Bis(trichloromethyl)benzene Bis(2,4,5-trichlorophenyl) disulfide 1,2-Bis(trichlorosilyl)ethane 3,5-Bis(trifluoromethyl)aniline

Formula

Formula weight

Beilstein reference

Density

Refractive index

0.94320

1.4371

Melting point

Boiling point

Solubility in 100 parts solvent

[H2C ¨ C(CH3)CH2O]2C( ¨ O) (O2NC6H4O)2C( ¨ O)

170.21 304.21

61, 120

141

O2NC6H4SSC6H4NO2

308.22

6, 339

83

i aq; s alc, eth

O2NC6H4SSC6H4NO2

308.33

6, 340

181

sl s alc

[C18H37OP(OCH2)2]2

721.01

C6Br5OC6Br5

969.22

0.925

1.457

202

Flash point

40

72

261

300

61, 108

364.40

244

CH3C6H4SSC6H4CH3

246.39

6, 425

43–46

i aq; s alc; v s eth

CH3C6H4S(O)C6H4CH3

230.33

6, 419

94–96

v s alc, bz, chl, eth

(C4H9)3SnOSn(C4H9)3

596.08

Cl3CC6H4CCl3

312.84

Cl3C6H4SSC6H4Cl3

425.01

Cl3SiCH2CH2SiCl3

296.64

1.48320 4

1.47320

(F3C)2C6H3NH2

229.13

1.467

1.433520

1.170

1.486420

5, 385

1802mm

112

108–110

i aq; 26 acet; 38 bz; 22 CCl4; 33 eth; 3 MeOH

140–144 24.5

201–202 8515mm

83

b206 b207

b208 b209

b210

b211 b212

b213

1,3-Bis(trifluoromethyl)benzene N,O-Bis(trimethylsilyl)acetamide Bis(trimethylsilyl)acetylene Bis(trimethylsilyl)formamide N,O-Bis(trimethylsilyl)hydroxylamine 1,2-Bis(trimethylsilyloxy)ethane N,O-Bis(trimethylsilyl)trifluoroacetamide Bis(triphenylphosphine)dicarbonylnickel

Bis(phenylmethyl) disulfide, d57

F3CC6H4CF3

214.0

1.379025

1.391625

116

CH3C ¨ N ˆ Si(CH3)3 ı O ˆ Si(CH3)3 (CH3)3SiC ˜ CSi(CH3)3

203.43

0.83220 4

1.417020

7335mm

11

170.41

0.77020 4

1.41320

137

2

HC ¨ NSi(CH3)3 ı O ˆ Si(CH3)3 (CH3)3SiONHSi(CH3)3

189.41

0.885

1.438120

54– 5513mm

177.40

0.830

1.411220

78– 28 80100mm

(CH3)3SiOCH2CH2OSi(CH3)3 CF3C[¨NSi(CH3)3]OSi(CH3)3

206.43

0.842

1.403420

165–166

46

257.40

0.969

1.393920

5014mm

23

[(C6H5)3P]2Ni(CO)2

639.32

“Bis-tris,” b183

10

209

“Bis-tris” propane, b214

1.129

1.130

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b214

Name

b215 b216

1,3-Bis[tris(hydroxymethyl)methylamino]propane Biuret 1-Borneol

b217 b218 b219

1-Bornyl acetate N-Bromoacetamide p-Bromoacetanilide

b220 b221

Bromoacetic acid -Bromoacetophenone p-Bromoacetophenone Bromoacetyl bromide Bromoacetyl chloride 2-Bromoaniline 3-Bromoaniline 4-Bromoaniline 3-Bromobenzaldehyde Bromobenzene

b222 b223 b224 b225 b226 b227 b228 b229

b230 b231 b232

Bromobenzene-d5 4-Bromobenzenesulfonyl chloride 4-Bromobenzophenone

Formula weight

Beilstein reference

CH2[CH2NHC (CH2OH)3]2

282.34

43, 859

H2NCONHCONH2

103.08 154.25

3, 70 6, 72

1.4675 4 1.01120 4

196.29 137.97 214.07

6, 82 2, 181 12, 642

0.982

CH3CONBrH BrC6H4NHCOCH3 BrCH2COOH C6H5COCH2Br

138.95 199.05

2, 213 7, 283

1.93450 4 1.64720 4

BrC6H4COCH3

199.05

7, 283

1.647

BrCH2COBr BrCH2COCl BrC6H4NH2 BrC6H4NH2 BrC6H4NH2 BrC6H4CHO C6H5Br

201.86 157.40 172.03 172.03 172.03 185.03 157.02

2, 215 2, 215 12, 631 12, 633 12, 636 7, 238 5, 206

2.31722 22 1.908 1.57820 4 1.58020 4 1.4970100 4 1.587 1.495220 4

C6D5Br BrC6H4SO2Cl

162.06 255.52

11, 57

BrC6H4COC6H5

261.12

7, 422

Formula

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

170

110 204

d 190 212

1.4626

27 224 102–105 168

1.480450

50 50

208 13518mm

54

255

1.717

1.548020 1.496020 1.611320 1.625020 1.593520 1.558020

65 84

150 128 229 251

none none

30.72

230 156.2

96 51

5323mm 15315mm

65

74.5

82

350

31 16.8 66.3

112

v s alc; 2 aq i aq; 176 alc; s eth, bz, PE sl s aq; s alc, eth sl s aq; v s eth i aq; s bz, chl, EtAc v s aq, alc, eth i aq; v s alc, bz, chl, eth s alc, bz, eth, HOAc d aq, alc d aq, alc i aq; s alc, eth sl s aq; s alc, eth i aq; v s alc, eth i aq; v s alc, eth 0.044 aq; 10.4 alc; misc bz, chl, PE; 71.6 eth i aq; d alc; v s eth i alc; sl s bz, eth

b233

b237 b238 b239

2-Bromobenzotrifluoride 3-Bromobenzotrifluoride 2-Bromobenzyl alcohol 2-Bromobenzyl bromide 4-Bromobiphenyl 1-Bromobutane 2-Bromobutane

b240 b241 b242

1-Bromo-2-butene 2-Bromo-2-butene 4-Bromo-1-butene

b234 b235 b236

BrC6H4CF3

225.01

1.65220

1.481720

168

51

BrC6H4CF3

225.01

1.613

1.474920

152

43

BrC6H4CH2OH

187.04

6, 445

BrC6H4CH2Br

249.94

5, 308

BrC6H4C6H5 CH3CH2CH2CH2Br CH3CH2CHBrCH3

233.11 137.02 137.03

5, 580 1, 119 1, 119

CH3CH ¨ CHCH2Br CH3CH ¨ C(Br)CH3 BrCH2CH2CH ¨ CH2

135.01 135.01 135.01

1, 205 1, 205 11, 84

2-Bornanone, c3 Bromal, t201 Bromoacetaldehyde diethyl acetal, b267

82

s hot aq; v s alc, eth d hot aq; s alc, eth

1.619320

31

12919mm

9.932725 4 1.268625 4 1.253025 4

1.437425 1.436020

87 112.4 112.4

310 101.6 21

23

1.312 1.328 1.323020 4

1.476520 1.461320 1.460830

99 90740mm 100

11 1 1

Bromoanisoles, b301, b302, b303 p-Bromobenzenethiol, b354 4-Bromobenzyl cyanide, b329

i aq; s alc, bz, eth i aq; s alc, bz, eth 0.1 aq; v s alc, eth

i aq; s alc, eth

exo-2-Bromobicyclo[2.2.1]heptane, b318 Bromobutanedioic acid, b350

1.131

1.132

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b243 b244 b245 b246 b247 b248 b249 b250 b251 b252 b253 b254 b255 b256

Formula weight

Beilstein reference

C6H5OCH2CH2CH2CH2Br

229.12

62, 82

CH3CH2CH(Br)COOH

167.01 231.14

2, 281 72, 101

ClC6H4COCH2Br

233.50

7, 285

BrC6H4Cl

191.46

5, 209

1.638225 4

1.578925

BrC6H4Cl

191.46

5, 209

1.630220 4

1.577120

BrC6H4Cl

191.46

5, 209

1.57671 4

Br(Cl)C6H3CF3

259.47

ClCH2CH2CH2CH2Br

171.47

53, 294

Br(Cl)C6H2(OH)CH3

221.49

6, 360

Br(Cl)CF2

165.4

ClCH2CH2Br

143.43

1, 89

258.51

211, 222

129.39

1, 67

Name 4-Bromobutyl phenyl ether 2-Bromobutyric acid endo-3-Bromo-Dcamphor -Bromo-p-chloroacetophenone 2-Bromochlorobenzene 3-Bromochlorobenzene 4-Bromochlorobenzene 3-Bromo-4-chlorobenzotrifluoride 1-Bromo-4-chlorobutane 4-Bromo-6-chloro-ocresol Bromochlorodifluoromethane 1-Bromo-2-chloroethane 7-Bromo-5-chloro-8hydroxyquinoline Bromochloromethane

Formula

ClCH2Br

Density

Refractive index

Melting point 41–42

1.566920 20 1.449

1.472020

4 76–78

Boiling point

Flash point

153– 15618mm 10310mm 112 244

Solubility in 100 parts solvent

6.7 aq; s alc, eth i aq; 15 alc; 200 chl; 62 eth

96.5 204

79

i aq; v s bz

21

196

80

i aq; v s alc, eth

1.553170

64.5

196

1.74325

1.497325

22

191–192

1.488

1.487520

8230mm

0.1 aq; misc MeOH, eth

60

i aq; s alc, chl, eth

47 1.8321 1.739220 4

1.491720

160.5

4.01

18.4

106.6

none

0.7 aq; misc org solv

67.8

none

0.9 aq; misc MeOH, eth

177–179 1.92325 4

1.48025

88

b257 b258

b259 b260 b261 b262 b263 b264 b265 b266 b267

1-Bromo-3-chloropropane 2-Bromo-2-chloro1,1,1-trifluoroethane -Bromocinnamaldehyde Bromocycloheptane Bromocyclohexane 3-Bromocyclohexene Bromocyclopentane Bromocyclopropane 1-Bromodecane Bromodichloromethane 2-Bromo-1,1-diethoxyethane

2-Bromo-p-cumene, b298 -Bromocumene, b297

1, 109

1.472

1.48620

1.863625

1.373825

ClCH2CH2CH2Br

157.44

HC(Br)ClCF3

197.4

C6H5CH ¨ C(Br)CHO

211.06

7, 358

BrC7H13 BrC6H11

177.09 163.06

5, 29 5, 24

1.288722 4 1.326415 4

1.505220 1.495615

BrC5H9 BrC3H5 CH3(CH2)9Br HCBrCl2

161.04 149.04 120.98 221.19 163.83

52, 40 5, 19

1.389020 4 1.390020 4

12, 130 1, 67

1.065820 4 1.98020

1.529220 1.488120 1.460520 1.456020 1.496420

BrCH2CH(OC2H5)2

197.08

1, 625

1.310

1.438520

50

143.5

none

0.1 aq; misc org solv

7210mm 165.8

68 62

i aq; v s chl, eth 0.1 aq; 10 MeOH; 71 eth

64–6515mm 137–139 69 238 89.2

35 2 94 none

50

66–68

4-Bromodiphenyl ether, b330

30 55

6718mm 180 d

51

Bromoethene, b284

i aq; v s chl, eth sl s aq; misc org solv s hot alc

1.133

1.134

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b268 b269 b270 b271 b272 b273

b274 b275 b276 b277 b278

b279 b280 b281

Name 4-Bromo-1,2-dimethoxybenzene 1-Bromo-2,2-dimethoxypropane 4-Bromo-2,6-dimethylphenol 2-Bromo-4,6-dinitroaniline 3-Bromo-4,6-dinitrofluorobenzene 2-Bromo-2,2-diphenylacetyl bromide -Bromodiphenylmethane 1-Bromododecane 1-Bromo-2,3-epoxypropane Bromoethane 2-Bromoethanesulfonic acid, sodium salt 2-Bromoethanol 2-Bromoethyl acetate 2-Bromoethylamine HBr

Formula weight

Beilstein reference

Density

Refractive index

BrC6H3(OCH3)2

217.07

6, 784

1.702

1.574320

256

109

CH3C(OCH3)2CH2Br

183.05

1.355

1.447520

8780mm

40

BrC6H2(CH3)2OH

201.07

6, 485

78

BrC6H2(NO2)2NH2

262.02

12, 761

154

BrC6H2(NO2)2F

264.9

BrC(C6H5)2COBr

354.05

91, 283

63–65

C6H5CH(Br)C6H5

247.14

5, 592

40

18420mm

CH3(CH2)11Br H2C ˆ CHCH2Br O CH3CH2Br BrCH2CH2SO3Na

249.24 136.98

12, 133 17, 9

1.038 1.60120

1.458020 1.482020

9 40

1356mm 134–136

110 56

0.1 aq; s alc, eth i aq; sl s alc; s eth

108.97 211.02

1, 88 4, 7

1.470815

1.427615

118.6 283– 285 d

38.4

none

0.91 aq

BrCH2CH2OH CH3COOCH2CH2Br

124.97 167.01

1, 338 21, 57

1.762920 4 1.51420 4

1.492020 1.454720

150 159

40 71

BrCH2CH2NH2·HBr

204.90

4, 134

misc aq; s org solv v s aq; misc alc, eth v s aq, alc

Formula

Melting point

Boiling point

Flash point

subl

Solubility in 100 parts solvent

v s hot alc, hot acet

90–91

13.8 172–174

b282 b283 b284 b285 b286 b287 b288 b289 b290 b291 b292 b293 b294

o-Bromo(ethyl)benzene (2-Bromoethyl)benzene Bromoethylene 2-Bromoethyl ethyl ether 2-Bromoethyl phenyl ether N-(2-Bromoethyl)phthalimide 2-Bromofluorobenzene 3-Bromofluorobenzene 4-Bromofluorobenzene 1-Bromoheptane 2-Bromoheptane 1-Bromohexadecane 1-Bromohexane

(Bromomethyl)benzene, b85

CH3CH2C6H4Br

185.07

5, 355

1.356625 25

1.560320

199

C6H5CH2CH2Br

185.07

5, 356

1.355

1.556320

221

89

H2C ¨ CHBr BrCH2CH2OCH2CH3

106.96 153.02

1, 188 1, 338

1.49320 1.357220 4

1.435020 1.445020

15.8 150

21

BrCH2CH2OC6H5

201.07

6, 142

34

14440mm

65

254.09

21, 461

81–84

139.5

175.01

1.601

1.533720

156

43

BrC6H4F

175.01

1.567

1.525720

150

38

BrC6H4F

175.01

5, 209

1.59315

1.531015

17.4

151–152

60

H(CH2)7Br H(CH2)5CH(Br)CH3 H(CH2)16Br H(CH2)6Br

179.11 179.11 305.35 165.08

1, 155 1, 155 12, 138 1, 144

1.138420 4 1.142 0.9991 1.176320 4

1.450520 1.447020 1.4618 1.4475

58

180 6621mm 336 154–158

60 47 177 57

Bromoform, t206

i aq; misc alc, eth sl s aq; misc alc, eth i aq; v s alc, eth s hot aq; v s eth

BrC6H4F

17.8 85

0.1 aq; misc org solv i aq; s bz, eth

i aq; v s alc, eth i aq; misc org solv i aq; misc alc, eth

1.135

1.136

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b295 b296 b297 b298 b299 b300 b301 b302 b303 b304 b305 b306 b307 b308

Formula weight

Beilstein reference

Density

Refractive index

CH3(CH2)3CH(Br) COOH

195.06

2, 325

1.370

1.472020

C6H5CH(CH3)CH2Br

226.03 199.10

21, 453 51, 191

1.316

1.548020

CH3(Br)C6H3CH(CH3)2

213.0

1.25325 25

1.53525

17, 435

1.905

1.540020

94.94

1, 67

1.73200

1.423410

BrC6H4OCH3

187.04

6, 197

1.501825 4

BrC6H4OCH3

187.04

6, 198

BrC6H4OCH3

187.04

6, 199

CH3(Br)C6H3NH2

186.06

12, 838

(CH3)2CHCH2CH2Br

151.05

1, 136

1.21015 4

1.440920

C6H11CH2Br

177.09

52, 18

1.269

1.490720

76–7726mm 57

167.01

192, 8

1.613

1.481720

80–8227mm 62

124.97

1, 582

1.531

1.455020

87

Name DL-2-Bromohexanoic

acid 5-Bromoisatin (2-Bromoisopropyl)benzene 2-Bromo-4-isopropyl1-methylbenzene Bromomaleic anhydride Bromomethane 2-Bromo-1-methoxybenzene 3-Bromo-1-methoxybenzene 4-Bromo-1-methoxybenzene 4-Bromo-2-methylaniline 1-Bromo-3-methylbutane (Bromomethyl)cyclohexane 2-Bromomethyl-1,3dioxalane Bromomethyl methyl ether

Formula

176.96 CH3Br

BrCH2OCH3

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

136– 13818mm 251–253 10818mm 20

91

120

i aq; 50 MeOH; misc org solv

215

112

84

3.56

none

1.573720

2

223

96

1.477

1.563520

211

93

1.456420 4

1.563020

10

223

56

240

112

119.7

0.1 aq; s alc, chl, eth i aq; v s alc, eth i aq; s alc, eth

94

sl s aq; v s alc, eth sl s aq; v s alc

32

26

0.02 aq; misc alc, eth

b309

1-Bromo-2-methylnaphthalene b310 1-Bromo-2-methylpropane b311 2-Bromo-2-methylpropane b311a -Bromo--methylpropiophenone b312 1-Bromonaphthalene

b313 b314 b315 b316 b317 b318 b319

1-Bromo-1-naphthol 1-Bromo-2-nitrobenzene 5-Bromo-2-nitrobenzotrifluoride 2-Bromo-2-nitro-1,3propanediol 1-Bromononane exo-2-Bromonorbornane 1-Bromooctadecane

-Bromoisobutyrophenone, b311a 2-Bromomesitylene, b362

BrC10H6CH3

221.10

5, 568

1.418

1.648420

(CH3)2CHCH2Br

137.03

1, 126

1.264120

1.436220

(CH3)3CBr

137.03

1, 127

1.21525 25

1.42525

C6H5COC(CH3)2Br

227.11

7, 316

1.350

1.556120

C10H7Br

207.08

5, 547

1.483420 4

1.658020

BrC10H6OH BrC6H4NO2

223.07 202.01

6, 650 51, 247

09.932725 4

O2N(Br)C6H3CF3

270.02

(HOCH2)2C(Br)NO2

199.99

1, 476

H(CH2)9Br

207.16 175.07

11, 63

H(CH2)18Br

333.41

11, 69

1.799225

1.518025

296

112

119

91.5

18

16.2

73.1

18

14830mm

112

1

281.1

112

78 43

130 d 261

misc alc, bz, chl, eth i aq; s alc, bz, eth v s alc; s bz, eth

40–44

99–100

51 60

i aq; s chl, eth

0.06 aq; misc alc, eth i aq; misc org solv

133 1.084 1.363

-Bromo-4-nitro-o-cresol, h155

1.454020 1.514820

201 8229mm 23

21612mm

-Bromo-p-nitrotoluene, n46

i aq; s alc, eth

1.137

1.138

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b320 b321 b322 b323 b324 b325 b326 b327 b328 b329 b330 b331 b332 b333 b334 b335 b336 b337 b338

Name 1-Bromooctane Bromopentafluorobenzene 1-Bromopentane 2-Bromopentane 9-Bromophenanthrene 2-Bromophenol 4-Bromophenol 2-Bromo-2-phenylacetic acid p-Bromophenylacetic acid p-Bromophenylacetonitrile 4-Bromophenyl phenyl ether 1-Bromo-3-phenylpropane 1-Bromopropane 2-Bromopropane 3-Bromo-1-propanol 1-Bromo-1-propene 2-Bromo-1-propene 2-Bromopropionic acid 3-Bromopropionic acid

Formula weight

Beilstein reference

Density

Refractive index

Melting point

H(CH2)8Br BrC6F5

193.13 246.97

1, 160

1.10825 4 1.94720

1.450325 1.449020

55 31

201 137

78 87

i aq; misc alc, eth

H(CH2)5)Br

151.05

1, 131

1.233715 4

1.444420

88

129.6

31

i aq; s alc; misc eth

CH3CH2CH2CH(Br)CH3

1, 131 5, 671 6, 197 6, 198 9, 451

1.203920 4 1.409101 4 1.492 1.587580

1.440320

117 1902mm 194 238

20

BrC6H4OH BrC6H4OH C6H5CH(Br)COOH

151.05 257.14 173.01 173.01 215.05

BrC6H4CH2COOH

215.05

9, 451

119

sl s aq; v s alc, eth

BrC6H4CH2CN

196.05

9, 451

47–49

i aq; sl s alc; v s bz

BrC6H4OC6H5

249.11

61, 105

1.423

1.607020

C6H5CH2CH2CH2Br

199.10

5, 391

1.310

1.545020

CH3CH2CH2Br CH3CH(Br)CH3

123.00 123.00

1, 108 1, 108

1.359715 1.322215

1.437015 1.428515

BrCH2CH2CH2OH CH3CH ¨ CHBr CH3C(Br) ¨ CH2 CH3CH(Br)COOH

139.00 120.98 120.98 152.98

1, 356 1, 200 1, 200 2, 254

1.537420 4 1.413320 4 20 1.3624 1.700020

1.485820 1.453820 1.442520 1.475020

BrCH2CH2COOH

152.98

2, 256

1.480

Formula

1.589220

54 –58 6 68 83

Boiling point

Flash point

42

305

112

220

101

110.1 89.0

71.0 59.5

25 19

116 125 25.7

625mm 63 49 203

4 4 100

18

62.5

65

Solubility in 100 parts solvent

i aq; s alc, eth s aq; misc chl, eth 14 aq; v s alc, chl

0.23 aq30; misc alc 0.3 aq18; misc alc, bz, chl, eth s aq; misc alc, eth i aq v s aq, alc, eth s aq, alc, bz, chl, eth

b339 b340 b341 b342 b343 b344 b345 b346 b347 b348 b349 b350

3-Bromopropionitrile 2-Bromopropionyl chloride 3-Bromopropionyl chloride -Bromopropiophenone 3-Bromopropyl phenyl ether 3-Bromopropyne 2-Brompyridine 3-Bromopyridine 3-Bromoquinoline 5-Bromosalicylic acid -Bromostyrene Bromosuccinic acid

-Bromophenetole, b286 3-Bromopropene, a85

BrCH2CH2CN CH3CH(Br)COCl

133.98 171.43

22, 231 2, 256

1.615220 4 1.70011

1.480020 1.480020

7810mm 133

98 51

BrCH2CH2COCl

171.43

22, 231

1.701

1.496820

5717mm

79

C6H5COCHBrCH3

213.08

7, 302

1.43020 4

1.571520

250

112

C6H5OCH2CH2CH2Br

215.10

6, 142

1.365

1.546420

BrCH2C ˜ CH BrC5H4N BrC5H4N

1, 248 20, 233 20, 233 20, 363 10, 107

1.335 1.65718 1.64504 1.533

1.490520 1.572020 1.569520 1.664020

Br(HO)C6H3COOH

118.97 158.00 158.00 208.06 217.02

C6H5CH ¨ CHBr HOOCCH2CH(Br)COOH

183.05 196.99

5, 477 2, 621

1.42220 4 2.073

1.606620

3-(Bromopropyl)benzene, b330

10–11

130– 13414mm 88–90 194 142–143 173 15 276 166 7 172 d

11220mm

v s alc, eth d aq; s chl, eth

s alc, bz, eth, acet

96 18 54 51 112

79

5-Bromopseudocumene, b361

i aq; s org solv s aq; v s alc, eth s HOAc 0.3 aq80; 85 alc25; 70 eth25 i aq; misc alc, eth 18 aq; s alc

1.139

1.140

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

177.99

21, 380

2.098

Refractive index

b351

N-Bromosuccinimide

b352

1-Bromotetradecane

H(CH2)14Br

277.30

12, 136

1.012425 4

1.460020

b353 b354 b355

2-Bromothiophene 4-Bromothiophenol 2-Bromotoluene

Br(C4H3S) BrC6H4SH BrC6H4CH3

163.04 189.08 171.04

17, 33 6, 330 5, 304

1.68420 4

1.586020

1.42225 25

b356 b357 b358

3-Bromotoluene 4-Bromotoluene Bromotrichloromethane 1-Bromotridecane Bromotrifluoromethane 5-Bromo-1,2,4-trimethylbenzene 2-Bromo-1,3,5-trimethylbenzene Bromotrimethylgermane Bromotrimethylsilane Bromotriphenylethylene Bromotriphenylmethane 11-Bromoundecanoic acid

BrC6H4CH3 BrC6H4CH3 BrCCl3

171.04 171.04 198.28

5, 305 5, 305 1, 67

H(CH2)13Br BrCF3

263.27 148.92

12, 134 13, 83

BrC6H2(CH3)3

199.10

5, 403

BrC6H2(CH3)3

199.10

5, 408

(CH3)3GeBr

b359 b360 b361 b362 b363 b364 b365 b366 b367

Melting point

Boiling point

Flash point

173 sl d

6

17820mm

112

1.55225

151 239 181

60

76 26

1.409920 4 1.395935 35 1.99725 25

1.551720 1.5490 1.5063

39.8 28.5 21

183.7 184.5 103.8

60 85 none

1.026220 4 1.580020 4

1.459220

7

15010mm 57.8

112

73

235

1.301

1.551120

2

225

197.60

1.54418

1.470520

25

113.7

(CH3)3SiBr (C6H5)2C ¨ C(Br)C6H5

153.10 335.22

1.160

1.414520

(C6H5)3CBr

323.24

5, 704

152–154 23015mm

Br(CH2)10COOH

265.20

22, 315

51

79

78

Solubility in 100 parts solvent 1.5 aq; 14.4 acet; 3.1 HOAc; 0.02 CCl4 s alc; v s chl; misc bz, acet v s acet, eth 0.1 aq; misc alc, bz, chl, eth s alc, bz, eth s alc, bz, eth misc org solv v s chl v s chl i aq; s alc

96

i aq; s bz; v s eth

1

114–115

1742mm

i aq; v s alc

b376 b377 b378 b379 b380

-Bromo-o-xylene -Bromo-m-xylene 2-Bromo-p-xylene 4-Bromo-o-xylene Brucine 1,2-Butadiene 1,3-Butadiene 1,3-Butadienyl acetate 1,3-Butadiyne 2-Butanamine Butane 1,4-Butanediamine Butanedinitrile

CH3CH ¨ C ¨ CH2 CH2 ¨ CHCH ¨ CH2 CH3C( ¨ O)OCH ¨ CHCH ¨ CH2 HC ˜ CC ˜ CH CH3CH2CH(NH2)CH3 CH3CH2CH2CH3 H2NCH2CH2CH2CH2NH2 NCCH2CH2CN

b381 b382

1,2-Butanediol 1,3-Butanediol

CH3CH2CH(OH)CH2OH CH3CH(OH)CH2CH2OH

b368 b369 b370 b371 b372 b373 b374 b375

BrCH2C6H4CH3 BrCH2C6H4CH3 BrC6H3(CH3)2 BrC6H3(CH3)2

-Bromotoluene, b85 Bromo-,,-trifluorotoluenes, b233, b234 3-Bromo-1,7,7-trimethylbicyclo[2.2.1]heptane-2one, b245 4-Bromoveratrole, b268

185.07 185.07 185.07 185.07 394.45 54.09 54.09 112.13

5, 365 5, 374 5, 385 5, 365 272, 797 1, 249 1, 249 23, 295

1.38123 1.37023 1.340 1.37015 15

0.945

1.42051 1.429325 1.469020

50.06 73.14 58.12 88.15 80.09

13, 1056 4, 160 4, 264 2, 615

0.736404 0.730815 4 0.60110 25 0.8774 0.986760 4

1.41895 1.396315 1.356213 1.456920 1.417360

36 104.5 138.3 27–28 57.9

10.3 66 0.50 158–160 265–267

90.12 90.12

1, 477 1, 477

1.00618 0 1.005320 20

1.438020 1.44120

50

207.5 207.5

0.67610 4 0.6506 4

4-Bromo-2,6-xylenol, b270 BSA, b207 BSTFA, b212 BTMSA, b208 Busulfan, b188

1.574220 1.556020 1.550520 1.556020

21 9–10 178 136.2 108.9

223–224 185340mm 199–201 215

82 82 79 80

10.9 4.4 6040mm

33 19 51

93 121

s alc, eth s alc, eth v s alc, eth 77 alc; 1 bz; 20 chl misc alc, eth misc alc, eth

v s eth; s bz, acet misc aq, alc s aq 11.5 aq; s acet, chl, diox; sl s bz, eth s aq, alc, acet s aq, alc, acet; 9 eth

-Butadiene sulfone, d368 Butanedioic acid, s14 1,4-Butanediol diglycidyl ether, b175 1,4-Butanediol dimethanesulfonate, b188

1.141

1.142

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

b383

1,4-Butanediol

HOCH2CH2CH2CH2OH

b384 b385 b386

meso-2,3-Butanediol D-()-2,3-Butanediol

2,3-Butanedione

CH3CH(OH)CH(OH)CH3 CH3CH(OH)CH(OH)CH3 CH3C(O)C(O)CH3

b387 b388 b389 b390

1,4-Butanedithiol 1-Butanethiol 2-Butanethiol 1,2,4-Butanetriol

b391 b392

1-Butanol 2-Butanol

HSCH2CH2CH2CH2SH CH3CH2CH2CH2SH CH3CH2CH(SH)CH3 HOCH2CH2CH(OH)CH2OH CH3CH2CH2CH2OH CH3CH2CH(OH)CH3

b393

2-Butanone

CH3CH2COCH3

Formula weight

Beilstein reference

Density

Refractive index

Melting point

90.12

1, 478

1.01625 4

1.445220

120.9

90.12 90.12 86.09

1, 479 12, 546 1, 769

0.993925 4 0.986925 4 0.99015 15

1.432435 1.431525 1.395120

34.4 19.7

122.25 90.19 90.19 106.12

1, 479 1, 370 1, 373 1, 519

1.042 0.836725 4 0.824625 4 1.01820

1.529020 1.440325 1.433825 1.474820

74.12 74.12

1, 367 1, 371

0.809720 4 0.806920 4

72.11

12, 726

Boiling point

Flash point

Solubility in 100 parts solvent

230

112

182 180715mm 88

85 85 26

115.7 165

10630mm 98.5 85.0 19118mm

70 12 21 167

misc aq, alc, acet; 0.3 bz; 3.1 eth; 0.9 PE misc aq, alc misc aq, alc; s eth 25 aq; misc alc, eth i aq; v s alc 0.06 aq; v s alc, eth sl s aq; v s alc, eth v s aq, alc

1.399320 1.397220

88.6 114.7

117.7 99.5

35 26

0.804920 4

1.378820

86.7

79.6

3

1.4428 1.396220 1.393125 1.384825 1.479320 1.477920

29.5 185.3 138.9 105.6 12.5 27.3

7225mm 6.3 3.7 0.88 234 132

CH3CH2C ( ¨ NOH)CH3 CH3CH2CH ¨ CH2 CH3CH ¨ CHCH3 CH3CH ¨ CHCH3 HOCH2CH ¨ CHCH2OH HOCH2CH ¨ CHCH2OH

87.12 56.10 56.10 56.10 88.11 88.11

12, 730 13, 715 13, 728 13, 730 12, 567 13, 2252

b400

2-Butanone oxime 1-Butene cis-2-Butene trans-2-Butene cis-2-Butene-1,4-diol trans-2-Butene-1,4diol 3-Butenenitrile

0.923220 4 0.6255185 4 0.621320 4 0.604120 4 0.070020 4 20 0.0704

H2C ¨ CHCH2CN

67.09

2, 408

0.834120 4

1.406020

87

119

b401

cis-2-Butenoic acid

CH3CH ¨ CHCOOH

86.09

2, 412

1.026720 4

1.448214

14

168–169

b394 b395 b396 b397 b398 b399

128

21

7.4 aq; misc alc, eth 12.5 aq; misc alc, eth 24 aq; misc alc, bz, eth s aq; misc alc, eth i aq; v s alc, eth i aq; v s alc, eth i aq; v s alc, eth s aq; v s alc v s aq, alc sl s aq; misc alc, eth v s aq; s alc

b402

trans-2-Butenoic acid

CH3CH ¨ CHCOOH

86.09

2, 408

0.96480 4

1.422877

71.4

185.0

87

b403 b404 b405 b406

3-Butenoic acid cis-2-Buten-1-ol trans-2-Buten-1-ol 3-Buten-2-one

H2C ¨ CHCH2COOH CH3CH ¨ CHCH2OH CH3CH ¨ CHCH2OH H2C ¨ CHCOCH3

86.09 72.11 72.11 70.09

2, 407 1, 442 1, 442 1, 728

1.009120 4 0.866220 4 0.845420 4 0.863620 4

1.424920 1.434220 1.428920 1.408620

39 89.4

163 123.6 121.2 81.4

65 56 56 6

b407 b408

1-Buten-3-yne 4-Butoxyaniline

HC ˜ CCH ¨ CH2 CH3(CH2)3OC6H4NH2

52.07 165.24

13, 1032 132, 226

0.709514 0.992

1.41611 1.534320

b409 b410

4-Butoxybenzoic acid 2-Butoxyethanol

CH3(CH2)3OC6H4COOH CH3(CH2)3OCH2CH2OH

194.23 118.18

102, 93 12, 519

0.901220 4

1.419820

150 40

170.2

60

b411

2-(2-Butoxyethoxy)ethanol Butyl acetate

HOCH2CH2OCH2CH2OC4H9 C4H9OOCCH3

162.23

12, 521

0.953620 20

1.430620

68.1

230.4

110

116.16

2, 130

0.881320 4

1.394120

73.5

126.1

37

DL-sec-Butyl acetate

CH3COOCH(CH3)C2H5 (CH3)3COOCCH3 (CH3)3COC( ¨ O)CH2C( ¨ O)CH3 H2C ¨ CHCOOC4H9 CH3CH2CH2CH2NH2

116.16 116.16 158.20

22, 141 2, 131

0.86525 4 0.866520 4 0.954

1.384025 1.385320 1.418020

112.3 97.8

32 15 60

128.17 73.14

22, 388 4, 156

0.89425 16 0.732725 4

1.4160 1.399225

50.5

148 77.9

38 1

(CH3)3CNH2 (CH3)3CNHCH2CH2OH

73.14 117.19

4, 173

0.695120 4

1.378820

67.5 42–45

44.4 8 90–9225mm 68

b412

b413 b414 b415 b416 b417 b418 b419

tert-Butyl acetate tert-Butyl acetoacetate Butyl acrylate Butylamine tert-Butylamine 2-(tert-Butylamino)ethanol

1.143

(E)-2-Butenal, c282 Buten-4-carboxylic acid, p50 Butopyronoxyl, b445

Butoxybenzene, b477 1-Butoxybutane, d115 Butyl alcohols, b393, b392, m382

54.6 aq; v s EtOH, bz, acet s aq; misc alc, eth 16.6 aq; misc alc 16.6 aq; misc alc v s aq, alc, acet, eth

5.1 148– 14913mm

sec-Butylamine, b377

5 aq; s most org solv misc aq, alc, bz, acet, PE, CCl4 0.43 aq; misc alc, eth; s most org solv 0.62 aq; s alc, eth i aq; misc alc, eth

i aq; s alc, eth misc aq, alc, eth, PE misc aq, alc

1.144

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b420 b421 b422 b423 b424 b425 b426 b427 b428 b429 b430 b431 b432

b433 b434 b435 b436

Name 3-(tert-Butylamino)1,2-propanediol 4-Butylaniline 2-tert-Butylanthraquinone Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl benzoate 4-tert-Butylbenzoic acid 4-tert-Butylbenzoyl chloride N-(tert-Butyl)benzylamine Butyl butyrate tert-Butyl carbazate 4-tert-Butylcatechol

tert-Butyl chloroacetate 4-tert-Butyl-1-chlorobenzene tert-Butylchlorodiphenylsilane Butyl chloroformate

Formula (CH3)3CNHCH2CH(OH)CH2OH CH3CH2CH2CH2C6H4NH2

Formula weight

Beilstein reference

Density

Refractive index

147.22 149.24

Melting point 70

121, 503

0.945

1.535020

264.32

Boiling point

Flash point

Solubility in 100 parts solvent

921mm 12015mm

101

183.3 173.3 169.1 250

59 45 34

100 88 82.7 57.9 22 167

0.860420 4 0.860820 4 0.866920 4 20 1.000

1.489820 1.490220 1.492720 1.496

1.007

1.536420

13520mm

87

12, 1022

0.881

1.496820

805mm

80

144.21 132.16 166.22

2, 271

0.871720 20

1.4035

156.9 650.03mm 285

51

i aq; misc alc, eth

151

0.2 aq80; 240 eth25; s alc; v s acet

ClCH2COOC(CH3)3

150.61

23, 444

1.053

1.423020

(CH3)3CC6H4Cl

168.67

5, 416

1.006

1.510820

(CH3)3CSi(C6H5)2Cl

274.87

1.057

1.567520

900.02mm

112

ClCOOC4H9

136.58

1.07425 4

1.411420

142

25

CH3CH2CH2CH2C6H5 CH3CH2CH(CH3)C6H5 (CH3)3CC6H5 C6H5COOC4H9 (CH3)3CC6H4COOH

134.22 134.22 134.22 178.23 178.23

(CH3)3CC6H4COCl

196.68

C6H5CH2NHC(CH3)3

163.27

CH3CH2CH2COOC4H9 H2NNHCOOC(CH3)3 (CH3)3CC6H3(OH)2

5, 413 5, 414 5, 415 9, 112 9, 560

42 55

1.04960 25

32, 11

misc alc, bz, eth misc alc, bz, eth misc alc, bz, eth i aq; s alc, eth i aq; v s alc, bz

48–4911mm 41 23–25

217

d aq, alc; misc eth

b437 b438 b439 b440 b441 b442 b443 b444 b445

S-tert-Butyl chlorothioformate tert-Butyl cyanoacetate 2-tert-Butylcyclohexanol 4-tert-Butylcyclohexanol 2-tert-Butylcyclohexanone 4-tert-Butylcyclohexanone Butyl decylo-phthalate N-Butyldiethanolamine Butyl 3,4-dihydro-2,2dimethyl-4-oxo-2Hpyran-6-carboxylate

Butyl bromides, b238, b239, b311 N-Butyl-1-butanamine, d107 Butyl carbitol, b411

1.08130 4

ClC( ¨ O)SC(CH3)3

152.6

NCCOOC(CH3)3

141.17

(CH3)3CC6H10OH

156.27

(CH3)3CC6H10OH

156.27

61, 18

(CH3)3CC6H9( ¨ O)

154.25

73, 143

(CH3)3CC6H9( ¨ O)

154.25

71, 29

C4H9OOCC6H4COOC10H21 C4H9N(CH2CH2OH)2

362.51 161.25 226.27

1.469130

42.010mm

1.420020

108

0.902

46 70

0.896

1.456520

i aq 11515mm

50

i aq

11620mm

96

i aq

202

0.98620 20

1.462520

1.05425 25

1.476720

Butyl Cellosolve, b410 Butyl chlorides, c64, c65, c162 2-tert-Butyl-o-cresol, b462

105

62.54mm

0.99425 25 4, 285

46

70

276

126

256–270

112

misc alc, chl, eth

2-tert-Butyl-p-cresol, b461 tert-Butyldihydroxybenzene, b432

1.145

1.146

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. b446

Name

Formula

Formula weight

b455 b456 b457

tert-Butyldimethylchlorosilane 1,3-Butylene diacetate N-Butylethanolamine Butyl ethyl ether 2-Butyl-2-ethyl-1,3propanediol Butyl ethyl sulfide tert-Butylhydrazine HCl tert-Butylhydroperoxide tert-Butylhydroquinone Butyl isocyanate tert-Butyl isocyanate Butyllithium

CH3CH2CH2CH2NCO (CH3)3CNCO CH3CH2CH2CH2Li

99.13 99.13 64.06

b458

tert-Butyllithium

(CH3)3CLi

64.06

b459 b460

Butyl methacrylate tert-Butyl methyl ether 2-tert-Butyl-4methylphenol

H2C ¨ C(CH3)COOC4H9 (CH3)3COCH3

142.19 88.15

(CH3)3CC6H3(CH3)OH

164.25

b447 b448 b449 b450 b451 b452 b453 b454

b461

Beilstein reference

Density

Refractive index

Melting point

(CH3)3CSi(CH3)2Cl

150.7

CH3CH(OOCCH3)CH2CH2OOCCH3 HOCH2CH2NHC4H9 C4H9OC2H5 HOCH2C(C2H5)(C4H9)CH2OH C4H9SC2H5 (CH3)3CNHNH2 HCl

174.20

2, 143

1.028

1.419920

117.19 102.18 160.25

13, 1502

0.8920 0.749520 4 0.93150 20

1.44420 1.381820 1.458725

3.5 103 41.4

118.24 124.61

13, 1522 43, 1734

0.837620 4

1.449120

95.1 144.2 191–174

0.89620 4

1.400720

4–5

(CH3)3C ˆ O ˆ OH

90.12

(CH3)3CC6H3(OH)2

166.22

91.5

Boiling point

Flash point

Solubility in 100 parts solvent

124–126 998mm

85

192 92.5 195100mm

77

v s aq; s alc

i aq; misc alc, eth 0.8 aq s chl

33–417mm

62

115 86 800.0001mm

26 26 pyrophoric pyrophoric 49 i aq; misc alc, eth 10 s aq; v s alc, eth

s aq, alc, chl, eth

129

4, 175

0.880 0.868

1.406120 1.386520

subl 700.1mm

1, 381

0.88925 15 0.758

1.422025 1.368520

109

170 56

0.924775 4

1.496975

51.7

237

i aq; s org solv

b462 b463 b464 b465 b466 b467 b468 b469

2-tert-Butyl-6methylphenol Butyl methyl sulfide Butyl nitrite tert-Butyl nitrite Butyl octadecanoate Butyl 4-oxopentanoate tert-Butyl peroxybenzoate 2-sec-Butylphenol

b470 b471 b472

2-tert-Butylphenol 3-tert-Butylphenol 4-sec-Butylphenol

b473 b474

4-tert-Butylphenol 2-(4-sec-Butylphenoxy)ethanol 2-(4-tert-Butylphenoxy)ethanol tert-Butyl phenyl carbonate Butyl phenyl ether

b475 b476 b477

1.519520

32

230

107

0.842620 4 0.911404 0.867120 4

1.447720 1.3768 1.368720

97.8

123.4 78 63

4

0.855120 4 0.973520 4

1.442225 1.427020

26.3

343 1076mm

160 91

194.23

1.021

1.499020

760.2mm

93

150.22

0.982

1.522220

12

228

112

150.22 150.22 150.22

62, 489

0.978320 4

1.522820

0.96920 4

1.5150

221–224 240 13625mm

110

6, 522

7 40–41 62

150.22 194.2

6, 524

0.908114 4 1.00825

1.4787114

(CH3)3CC6H3(CH3)OH

164.25

C4H9SCH3 C4H9ONO (CH3)3CONO

104.21 103.12 103.12

13, 1521 1, 369 12, 415

CH3(CH2)16COOC4H9 CH3C( ¨ O)CH2CH2COOC4H9 C6H5( ¨ O)O ˆ OC(CH3)3

340.60 172.22

22, 352

CH3CH2CH(CH3)C6H4OH (CH3)3CC6H4OH (CH3)3CC6H4OH CH3CH2CH(CH3)C6H4OH (CH3)3CC6H4OH CH3CH2CH(CH3)C6H4OCH2CH2OH (CH3)3CC6H4OCH2CH2OH C6H5OC( ¨ O)OC(CH3)3

194.3

1.01625

194.23

1.047

1.480520

CH3CH2CH2CH2OC6H5

150.22

0.935120 4

1.497020

Butyl disulfides, d113, d114 1,4-Butylene bis(2,3-epoxypropyl) ether, b175 1,3-Butylene glycol methyl ether, m57 1,2-Butylene oxide, e3 Butyl ether, d115

6, 143

Butyl ethyl ketone, h16 tert-Butyl fluoride, f20 Butyl glycol, b410 2,2-(Butylimino)diethanol, b444 Butyl iodides, i30, i31, i44

v s alc misc alc, eth sl s aq; v s alc, chl, eth, CS2 s alc, v s acet s alc, eth, acet

i aq; s alc; v s eth

115

s hot aq, alc, eth

100–101 237 20 15810mm

149

i aq; s alc, eth 0.1 aq

16710mm

157

0.1 aq

54

790.8mm 19

210.3

82

Butyl levulinate, b467 Butyl mercaptans, b388, m378, m379, m380 Butyl methyl ketone, d497 tert-Butyl perbenzoate, b468

1.147

1.148

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

b478

4-tert-Butylphenyl salicylate

HOC6H4COOC6H4C(CH3)3

270.31

b479 b480 b481 b482 b483 b484

CH3CH2COOC4H9 (CH3)3C(C5H4N) C4H9SnCl3 (CH3)3CC6H4CH3 C4H9SiCl3 CF3COOC4H9

130.19 135.21 282.17 148.25 191.5 170.1

C4H9Si(OCH3)3 (CH3)3C ˆ O ˆ O ˆ Si(CH3)3

178.3 162.3

C4H9NHCONH2 C4H9OCH ¨ CH2 (CH3)3CC6H3(CH3)2

116.16 100.16 162.28

41, 371

b490 b491 b492

Butyl propionate 4-tert-Butylpyridine Butyltin chloride 4-tert-Butyltoluene Butyltrichlorosilane Butyl trifluoroacetate Butyltrimethoxysilane tert-Butyl trimethylsilyl peroxide Butyl urea Butyl vinyl ether 5-tert-Butyl-mxylene 1-Butyne 2-Butyne 2-Butyne-1,4-diol

CH3CH2C ˜ CH CH3C ˜ CCH3 HOCH2C ˜ CCH2OH

b493

Butyraldehyde

CH3CH2CH2CHO

b494 b495 b496

Butyramide Butyric acid Butyric anhydride

CH3CH2CH2CONH2 CH3CH2CH2COOH [CH3CH2CH2C(O) ]2O

b485 b486

b487 b488 b489

Density

Refractive index

Melting point

Boiling point

Flash point

62–64 89.6

0.1 aq; 79 alc; 153 EtAc; 158 toluene misc alc, eth

0.881815 0.915 1.693 0.853 1.16120 4 1.026822

1.398225 1.495220 1.522920 1.489720 1.43620 1.35322

0.931220 4 0.821920 4

1.397920 1.393525

5, 447

0.779220 0.867

1.400720 1.494620

54.09 54.09 86.09

1, 249 1, 249 11, 261

0.711031 1.396220 4 0.691020 1.392020 4 1.45025

125.7 32.3 54–58

8.1 17.0 238

152

72.11

1, 662

0.801620 4

1.379120

96.4

74.8

6.7

87.12 88.11 158.20

2, 275 2, 264 2, 274

0.958220 4 0.966820 4

1.398020 1.413020

116 5.3 65.7

216 163.3 199.5

77 87

2, 241 20, 252 5, 439 41, 582

d 135

93–95 112.7

145.5 197 9310mm 192 142–143 100.2

Solubility in 100 parts solvent

63 81 54 d aq, hot alc; s eth

164–165 4141mm

94.2 205–206

9 72

s aq, alc, eth 0.3 aq

i aq; s alc, eth i aq; s alc, eth 374 aq; 83 alc; 0.04 bz; 2.6 eth; 70 acet 7.1 aq; misc alc, eth, acet, EtAc 16 aq; s alc misc aq, alc, eth s aq, alc(d), eth

86.09 86.09

171, 130 17, 234

1.056 1.12425 4

1.4109 1.434825

20 43.5

7329mm 204

60 98

69.11

22, 252

0.795415 4

1.386015

111.9

117.9

16

148.21 106.55

7, 313 2, 274

1.021 1.026321 4

1.519520 1.412220

13 89

222 102

88 21

Caffeine

194.19

26, 461

1.2318 4

238

subl 178

c2 c3

DL-Camphene

136.24 152.23

5, 156 7, 101

0.842254 4 0.992025 4

51–52 178.8

159 207.4

c4 c5

DL-Camphor

152.24 200.23

7, 135 9, 745

1.18620 4

b497 b498

3-Butyrolactone 4-Butyrolactone

b499

Butyronitrile

CH3CH2CH2CN

b500 b501

Butyrophenone Butyryl chloride

C6H5C(O)C3H7 CH3CH2CH2COCl

c1

D-()-Camphor

D-Camphoric acid

Butyl o-phthalate, d128 Butyl propyl ketone, 036 Butyl stearate, b466 Butyl sulfate, d131

Butyl sulfides, d132, d133 Butyl sulfite, d134 Butyl sulfone, d135 Butyrolactam, p275

1.455154

177 204 186–188

36

misc aq, alc, acet, bz, eth, CCl4 3.3 aq; misc alc, eth s aq, alc(d); misc eth 2.1 aq; 1.5 alc; 18 chl; 0.19 eth; 1 bz i aq; s alc, chl, eth 100 alc; 100 eth; 200 chl; 250 acet

64 4 aq; 100 alc; s chl, eth Cadaverine, p29 2-Camphanone, c3

1.149

1.150

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c6 c7

c8 c9

c10 c11 c12

c13 c14 c15

c16 c17 c18

Name

Formula

DL-Camphoric

anhydride D-10-Camphorsulfonic acid hydrate Carbazole 4-Carbethoxy-3methyl-3-cyclohexen-1-one Carbobenzyloxyglycine Carbohydrazide 2-(Carbomethoxy)ethylmethyldichlorosilane 2-Carbomethoxyethyltrichlorosilane 2-Carboxybenzaldehyde 4-Carboxy-1,2-benzenedicarboxylic anhydride 4-Carboxybenzenesulfonamide 2-Carboxyethylphosphonic acid DL-Carnitine HCl

Formula weight

Beilstein reference

Density

182.22

17, 455

1.19420 4

250.32

11, 316

167.21 182.22

20, 433 10, 631

C6H5CH2OC( ¨ O)NHCH2COOH H2NNHC( ¨ O)NHNH2 CH3OC( ¨ O)CH2CH2Si(CH3)Cl2

209.20

CH3OC( ¨ O)CH2CH2SiCl3 HC( ¨ O)C6H4COOH

221.6

90.09 201.1

Refractive index

Melting point 225

Boiling point

Flash point

270

s bz; sl s aq, alc, eth deliq moist air; sl s HOAc, EtAc; i eth

194 d

1.078

1.488020

245–246 355 268–272

Solubility in 100 parts solvent

112

122 3, 121

d 153

v s aq; i alc, bz, eth

1.18725 4

1.443925

98–9925mm

1.32520 4

1.44820

88–892mm

150.13

10, 666

96–98

192.13

18, 468

161–164 240– 24514mm

15.5 DMF; 49.6 acet; 21.6 EtAc

HOOCC6H4SO2NH2

201.20

11, 390

d 280

i aq, bz, eth; v s alc

HOOCCH2CH2P(O)(OH)2 (CH3)3NCH2CHOHCH2COOHHCl

154.06

42, 976 197 d

v s aq; i acet, eth

197.66

c19 c20 c21

trans--Carotene D-()-Carvone Catecholborane

Capric acid, d14 Caproaldehyde, h54 Caproic acid, h66 Caproic anhydride, h67 -Caprolactam, o57 -Caprolactone, h71 Capronitrile, h63 Caproyl chloride, h73 Caprylic acid, o29 Capryl alcohol, o30 Caprylaldehyde, o40

536.89 150.22 119.92

30, 87 7, 153

1.00020 20 0.96520 4

Caprylonitrile, o27 Capryloyl chloride, o37 CAPS, c337 N-(Carbamoylmethyl)iminodiacetic acid, a14 Carbamylurea, b215 Carbanilide, d693 Carbazole, d665 Carbitol, e35 Carbitol acetate, e36 Carbobenzoxy chloride, b90 4,4-Carboxyldiphthalic anhydride, b55

183 1.498920 1.507020

12

230 5050mm

88

i aq; s bz, chl, CS2 i aq; misc alc

N-Carbonylsulfamyl chloride, c240 Carboxybenzaldehyde, f33 (3-Carboxy-2-hydroxypropyl) trimethylammonium hydroxide, c18 3-Carbomethoxypropionyl chloride, m188 (Carboxymethylimino)bis(ethylenenitrilo)tetraacetic acid, d299 (Carboxylmethyl)trimethylammonium hydroxide, b128 3-Carboxypropyl disulfide, d708

1.151

1.152

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

c22

2-Chloroacetamide

ClCH2CONH2

c23

p-Chloroacetanilide

ClC6H4NHCOCH3

c24

Chloroacetic acid

ClCH2COOH

c25

c33

Chloroacetic anhydride p-Chloroacetoacetanilide Chloroacetonitrile -Chloroacetophenone o-Chloroacetophenone p-Chloroacetophenone Chloroacetyl chloride 2-Chloroacrylonitrile 2-Chloroaniline

ClC6H4NH2

127.57

c34 c35

3-Choroaniline p-Chloroaniline

ClC6H4NH2 ClC6H4NH2

c36

1-Chloroanthraquinone 2-Chloroanthraquinone

c26 c27 c28 c29 c30 c31 c32

c37

Beilstein reference

Density

Refractive index

93.51

2, 199

169.61

12, 611

1.38520 4

94.50

2, 194

1.580(c)

[ClCH2C(O) ]2O

170.98

2, 199

1.549420 4

CH3COCH2CONHC6H4Cl

211.65

ClCH2CN C6H5COCH2Cl

75.50 154.60

2, 201 7, 282

1.193 1.32415

1.422520

ClC6H4COCH3

154.60

71, 151

1.188

1.543820

ClC6H4COCH3

154.60

7, 281

1.19220 4

1.5549

ClCH2COCl

112.94

2, 199

1.41825 25

H2C ¨ C(Cl)CN

Melting point 118

Boiling point

Flash point

225 d

10 aq; 10 alc; sl s eth i aq; v s alc, eth, CS2 v s aq; s alc, bz, eth d aq; v s chl, eth

179 1.429765

63()

189

46

203

Solubility in 100 parts solvent

134 126 245

47

228738mm

88

sl s aq; s eth

20–21

237

90

i aq; misc alc, eth

1.453020

22.5

106

none

d aq, MeOH

1.096

1.429020

65

89

6

12, 597

1.212520 4

1.588120

1.94

208.8

97

127.57 127.57

12, 602 12, 607

1.215022 4 1.16977 4

1.593120 1.554685

10.4 72.5

230.5 232

123

242.66

7, 787

160

subl

242.66

7, 787

211

subl

87.51

54

i aq; v s alc, bz, eth

0.88 aq; s alc, bz, eth i aq; s alc, bz, eth s hot aq; v s alc, acet, eth, CS2 sl s alc; misc eth; s hot bz sl s alc, bz; i eth

c38 c39 c40 c41 c42 c43 c44 c45

2-Chlorobenzaldehyde 4-Chlorobenzaldehyde 2-Chlorobenzamide Chlorobenzene

ClC6H4CHO

140.57

7, 233

1.248320 4

1.5658

11

215

87

ClC6H4CHO

140.57

7, 235

1.19661 4

1.55261

47

214

87

ClC6H4CONH2 C6H5Cl

155.58 112.56

9, 336 5, 199

1.106320

1.524820

142–144 45.3 131.7

4-Chlorobenzenesulfonamide 4-Chlorobenzenesulfonyl chloride 4-Chlorobenzhydrol 2-Chlorobenzoic acid

ClC6H4SO2NH2

191.64

11, 55

146

ClC6H4SO2Cl

211.07

11, 55

55

ClC6H4CH(OH)C6H5 ClC6H4COOH

218.68 156.57

6, 680 9, 334

Cellosolve, e34 Cellosolve acetate, e37 Cetyl alcohol, h36 Cetyl bromide, b294 Chalcone, d686 CHES, c335

1.54425 4

Chloramine T, c247 Chloranils, t24, t25 Chloranilic acid, d172 Chlorendic anhydride, h30 Chloroacetaldehyde diethyl acetal, c81 Chloroacetaldehyde dimethyl acetal, c89

23

14115mm

58–60 142

Chloroacetone, c215 4-(Chloroacetyl)catechol, c86 Chloroanthranilic acid, a140 5-Chloroanthranilonitrile, a141 p-Chlorobenzenethiol, c243

sl s aq; s alc, bz, eth s aq; v s alc, bz, eth 0.049 aq30; v s alc, bz, chl, eth s hot aq, hot alc, hot eth d aq, alc; v s bz, eth 0.11 aq; v s alc, eth

1.153

1.154

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c46 c46a c47 c48 c49 c50 c51 c52 c53 c54 c55 c56 c57 c58 c59 c60

Name 3-Chlorobenzoic acid 4-Chlorobenzoic acid 2-Chlorobenzonitrile 4-Chlorobenzonitrile 2-Chlorobenzophenone 4-Chlorobenzophenone 2-Chlorobenzotrifluoride 3-Chlorobenzotrifluoride 4-Chlorobenzotrifluoride 2-(4-Chlorobenzoyl)benzoic acid 2-Chlorobenzoyl chloride 4-Chlorobenzoyl chloride 4-Chlorobenzyl alcohol 4-Chlorobenzylamine 2-Chlorobenzyl chloride 4-Chlorobenzyl chloride

Formula weight

Beilstein reference

Density

ClC6H4COOH

156.57

9, 337

1.49625 4

ClC6H4COOH ClC6H4CN ClC6H4CN ClC6H4COC6H5

156.57 137.57 137.57 216.67

ClC6H4COC6H5

216.67

ClC6H4CF3

180.56

1.354025

ClC6H4CF3

180.56

ClC6H4CF3

180.56

ClC6H4COC6H4COCH

260.68

10, 750

ClC6H4COCl

175.01

9, 336

1.382

1.571820

3

238

110

d aq, alc

ClC6H4COCl

175.01

9, 341

1.377

1.578020

14

222

105

d aq, alc

ClC6H4CH2OH

142.59

6, 444

72

234

ClC6H4CH2NH2 ClC6H4CH2Cl

141.60 161.03

12, 1074 5, 297

17

215 214

90 82

ClC6H4CH2Cl

161.03

5, 308

30

214

97

Formula

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

157–158

0.04 aq; v s alc, eth

9, 340 9, 336 9, 341 7, 419

241–243 46 232 93 22 44–47 300

0.02 aq; v s alc, eth s alc, eth s alc, bz, chl, eth

7, 419

77

19617mm

1.451325

6.4

152.3

1.331125

1.443825

56.7

137.7

36

1.35320

1.4463

33.2

138.7

47

s alc, acet, bz, eth

150

1.164 1.274

1.558620 1.559120

s alc, bz, eth

v s alc, eth

s alc; v s eth

c61

ClC6H4CH2 ˆC5H4N

203.67

1.390

1.586820

ClC6H4CH2 ˆ C5H4N

203.67

1.167

1.590020

c64

2( p-Chlorobenzyl)pyridine 4-(p-Chlorobenzyl)pyridine 1-Chloro-1,3-butadiene 1-Chlorobutane

c65

2-Chlorobutane

CH3CH2CH(Cl)CH3

c66 c67 c68

4-Chloro-1-butanol 3-Chloro-2-butanone cis-1-Chloro-2butene 3-Chloro-1-butene 3-Chloro-1-butyne 3-Chlorobutyric acid 4-Chlorobutyric acid 4-Chlorobutyronitrile 4-Chlorobutyryl chloride Chloro(chloromethyl)dimethylsilane trans-p-Chlorocinnamic acid Chlorocyclohexane 2-Chlorocyclohexanone

ClCH2CH2CH2CH2OH CH3CH(Cl)COCH3 CH3CH ¨ CHCH2Cl

108.56 106.55 90.55

12, 398 1, 669 12, 176

1.088320 4 1.055 0.942620 4

CH3CH(Cl)CH ¨ CH2 CH3CH(Cl)C ˜ CH CH3CH(Cl)CH2COOH

90.55 88.54 122.55

12, 174 14, 970 2, 277

20 0.9000120 4 1.4155 0.961 1.428020 1.442120 1.18620 4

ClCH2CH2CH2COOH ClCH2CH2CH2CN

122.55 103.55

2, 278 2, 278

1.233620 4 1.158

1.451020 1.441320

ClCH2CH2CH2COCl

141.00

2, 278

1.258

ClCH2Si(CH3)2Cl

143.09

1.086

ClC6H4CH ¨ CHCOOH

182.61

9, 594

ClC6H11 ClC6H9( ¨ O)

118.61 132.59

5, 21 7, 10

c62 c63

c69 c70 c71 c72 c73 c74 c75 c76 c77 c78

1.155

4-Chlorobenzyl mercaptan, c248

18320mm

112 112

H2C ¨ CHCH ¨ CHCl

88.54

13, 949

0.960120 4

1.471220

CH3CH2CH2CH2Cl

92.57

1, 118

0.886420 4

1.402120

123.1

78.44

6

92.57

1, 119

0.873220 4

1.397120

113.3

68.25

15

1.451820 1.417220 1.439020

68

v s chl

86–8920mm 32 117 21 84.1 15

0.11 aq; misc alc, eth 0.1 aq; misc alc, eth s alc, eth v s alc, eth s alc, acet

62–65 68–70 10917mm

20 1

19622mm 197

112 85

sl s aq; v s eth s alc, eth

1.460920

174

72

d aq, alc; s eth

1.437320

114752mm

21

142 8310mm

28 82

16.3 12–16

v s acet s alc, eth

248–250 1.00020 4 1.161

Chlorocresols, c158, c159

1.462020 1.483520

44 23

i aq; s alc, eth s bz, eth, diox

1.156

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c79 c80 c81 c82 c83 c84 c85 c86

c87 c88 c89 c90 c91 c92 c93

Formula weight

Beilstein reference

Density

Refractive index

ClC5H9

104.58

5, 19

1.005120 4

1.451220

CH3(CH2)9Cl ClCH2CH(OC2H5)2

176.73 152.62

1, 168 1, 611

0.868 1.018

1.436220 1.415720

ClCH2CH2CH(OC2H5)2

166.65

1, 632

0.995

1.424020

F2C(Cl)COOH

130.48

2, 201

CH3C(Cl)F2

100.50 86.47

Name Chlorocyclopentane 1-Chlorodecane 2-Chloro-1,1-diethoxyethane 3-Chloro-1,1-diethoxypropane Chlorodifluoroacetic acid 1-Chloro-1,1-difluoroethane Chlorodifluoromethane -Chloro-3,4-dihydroxyacetophenone 1-Chloro-2,4-dihydroxybenzene 2-Chloro-1,4-dihydroxybenzene 2-Chloro-1,1-dimethoxyethane 4-Chloro-3,5-dimethylphenol 1-Chloro-2,2-dimethylpropane Chlorodimethylsilane Chlorodimethylvinylsilane

Formula

HCClF2

1.355920

Melting point

34

Boiling point

Flash point

Solubility in 100 parts solvent

114

15

i aq

223 157

83 29

i aq

8425mm

36

22.9

121.5

1.11821

131

9

0.19 aq

1.20921

160

40.8

0.30 aq

14718mm

v s aq, alc, chl, eth

(HO)2C6H3C( ¨ O)CH2Cl

186.59

8, 273

176

ClC6H3(OH)2

144.56

62, 818

107

ClC6H3(OH)2

144.56

6, 849

101–102 263

ClCH2CH(OCH3)2

124.57

Cl(CH3)2C6H2OH

156.61

(CH3)3CCH2Cl

106.59

0.86620 4

(CH3)2Si(Cl)H (CH3)2Si(Cl)CH ¨ CH2

94.62 120.7

0.85220 4 0.88425 4

1.09420 20

1.414820

62, 463

130 115.5

246

1.404220

20

84.4

1.382720 1.41425

111

36 82.5

v s aq; i alc; s eth 28 0.1 aq; 1 alc; s bz, eth, alk 28

c94 c95 c96 c97 c98 c99 c100 c101 c102 c103 c104 c105 c106 c107 c108

1-Chloro-2,4-dinitrobenzene 1-Chloro-3,4-dinitrobenzene 2-Chloro-3,5-dinitrobenzoic acid -Chlorodiphenylmethane Chlorodiphenylmethylsilane Chlorodiphenylphosphine 1-Chlorododecane 1-Chloro-2,3-epoxypropane Chloroethane 2-Chloroethanol 2-(2-Chloroethoxy)ethanol 2-[2-(2-Chloroethoxy)ethoxy]ethanol 2-Chloroethylamine HCl 1-Chloro-2-ethylbenzene (2-Chloroethyl)benzene

ClC6H3(NO2)2

202.55

5, 263

1.498275 4

1.585760

ClC6H3(NO2)2

202.55

5, 262

1.686716

1.587020

ClC6H2(NO2)2COOH

246.56

9, 415

C6H5CH(Cl)C6H5

202.68

52, 600

(C6H5)2Si(Cl)CH3

232.8

(C6H5)2PCl

220.64

CH3(CH2)11Cl H2C ˆ CHCH2Cl O CH3CH2Cl

52–54

315

186 112

198

241 explodes 1403mm

0.3 aq 112

1.14020 4

1.595120

1.127720 4

1.574220

295

16, 763

1.229

1.633820

320

112

204.79 92.53

17, 6

0.867320 4 1.181220 4

1.4426 1.438120

9 57.2

116 116.1

93 33

64.52

1, 82

0.921404

1.374210

12.3

43

ClCH2CH2OH ClCH2CH2OCH2CH2OH

80.52 124.57

1, 337 1, 467

1.19720 4 1.180

1.442220 1.452920

136 to 138 67.5

128.6 815mm

60 90

ClCH2CH2OCH2CH2OCH2CH2OH ClCH2CH2NH2 HCl

168.62

1, 468

1.160

1.458020

1205mm

107

115.99

4, 133

ClC6H4C2H5

140.61

C6H5CH2CH2Cl

140.61

Chlorodibromomethane, d71 2-Chloro-N,N-diethylethylamine, d272

v s alc; s bz 5.9 aq; misc alc, chl, 0.45 aq0; 48 alc; misc eth misc aq, alc

146 81

1.05525 25 5, 354

17

sl s alc; s hot alc, bz, eth v s eth; s alc

1.069

1.530020

Chlorodimethyl ether, c155 2-Chloro-N,N-dimethylethylamine, d467

179.2 8416mm

i aq; misc alc, eth 66

s alc, bz, eth

4-Chlorodiphenylmethanol, c44 2-Chloroethyl alcohol, c103

1.157

1.158

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c109 c110 c111 c112 c113 c114 c115 c116 c117 c118 c119 c120 c121 c122 c123

Name Chloroethylene 2-Chloroethyl ethyl ether 2-Chloroethyl methyl ether N-(2-Chloroethyl)morpholine HCl N-(2-Chloroethyl)piperidine HCl 2-Chloroethyl p-toluenesulfonate 2-Chloroethyl vinyl ether 1-Chloro-2-fluorobenzene 1-Chloro-3-fluorobenzene 1-Chloro-4-fluorobenzene 2-Chloro-6-fluorobenzyl chloride 4-Chloro-4-fluorobutyrophenone 3-Chloro-4-fluoronitrobenzene 2-Chloro-4-fluorophenol 2-Chloro-4-fluorotoluene

Formula H2C ¨ CHCl ClCH2CH2OCH2CH3 ClCH2CH2OCH3

Formula weight

Beilstein reference

Density

Refractive index

Melting point

62.50 108.57

1, 186 1, 337

0.9714 0.989

1.412520

13.9 107

15

94.54

1, 337

1.035

1.411120

89–90

15

1530.3mm

112

159.7

186.08

Boiling point

Flash point

Solubility in 100 parts solvent sl s aq; s alc

186

184.11

20, 17

CH3C6H4SO3CH2CH2Cl

234.70

112, 45

1.294

1.529020

H2C ¨ CHOCH2CH2Cl

106.55

12, 473

1.048

1.437020

69.7

110

16

0.6 aq

ClC6H4F

130.55

51, 110

1.244

1.501020

42.5

138.5

31

s alc, eth

ClC6H4F

130.55

1.219

1.494420

126

20

s alc, eth

ClC6H4F

130.55

1.22620 4

1.496720

Cl(F)C6H3CH2Cl

179.02

1.401

1.537220

FC6H4C( ¨ O)CH2CH2CH2Cl Cl(F)C6H3NO2

200.64

1.220

1.525520

175.5

1.602817

1.567417

Cl(F)C6H3OH

146.5

Cl(F)C6H3CH3

144.58

5, 201

236

21.5

1.498525

s alc, eth

110 41.5 23

1.197220

130–131

12717mm 884mm 152–153

c124 c125 c126 c127 c128 c129 c130 c131 c132 c133 c134 c135

2-Chloro-6-fluorotoluene 4-Chloro-2-fluorotoluene Chloroform Chloroform-d 1-Chloroheptane 1-Chlorohexane 6-Chloro-1-hexanol 4-Chloro-4-hydroxybenzophenone 5-Chloro-8-hydroxy7-iodoquinoline 3-Chloro-4-hydroxymandelic acid 5-Chloro-8-hydroxyquinoline 1-Chloro-4-iodobenzene

Cl(F)C6H3CH3

144.58

Cl(F)C6H3CH3

144.58

CHCl3 CDCl3 CH3(CH2)6Cl CH3(CH2)5Cl Cl(CH2)6OH ClC6H4C( ¨ O)C6H4OH

119.39 120.39 134.65 120.62 136.62 232.67

ClC6H3(OH)CH(OH)COOH

ClC6H4I

2-Chloroethyl ether, b158 2-Chloro-6-fluorobenzal chloride, t233

1.191

1, 61 1, 154

1.498515 1.50 0.88116 0 0.878020 4 1.204

1.502620

156

1.499820

158

1.448615 1.444520 1.425020 1.423620 1.455720

82, 187

63.59

61.7 60.9 69 159–161 134 10814mm 175–178 25714mm

305.50

d 172

202.60

145–147

179.61

21, 95

238.46

5, 221

-Chloro-4-fluorotoluene, f16 2375-Chloro-2-hydroxyaniline, a148

53–54

none none 41 38 98

0.82 aq misc alc, eth i aq sl s aq; v s alc, eth

i alc, eth; 0.8 chl; 0.6 HOAc

130 1.18657 4

46

sl s aq HCl 226–227

s alc

Chlorohydroxybenzoic acids, c237, c238 1-Chloro-3-hydroxypropane, c214

1.159

1.160

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c136 c137

Name 1-Chloro-3-mercapto2-propanol Chloromethane

c137a 3-Chloro-4-methoxyaniline c138 5-Chloro-2-methoxyaniline c139 1-Chloro-2-methoxybenzene c140 1-Chloro-4-methoxy2-nitrobenzene c141 2-Chloro-6-methoxypyridine c142 2-Chloro-6-methylaniline c143 3-Chloro-2-methylaniline c144 3-Chloro-4-methylaniline c145 4-Chloro-2-methylaniline c146 5-Chloro-2-methylaniline c147 DL-4-Chloro-2-(methylbenzyl)phenol c148 1-Chloro-3-methylbutane

Formula HSCH2CH(OH)CH2Cl CH3Cl

Formula weight

Beilstein reference

Density

Refractive index

126.61

13, 2156

1.277

1.527620

1, 59

0.9220

1.371224

50.49

Melting point

571.3mm 97.7

ClC6H3(OCH3)NH2

157.60

13, 511

50–55

ClC6H3(OCH3)NH2

157.60

13, 383

83–85

ClC6H4OCH3

142.59

6, 184

CH3O(Cl)C6H3NO2

187.58

CH3O(Cl)(C5H3N)

143.57

CH3(Cl)C6H3NH2

141.60

121, 388

CH3(Cl)C6H3NH2

141.60

CH3(Cl)C6H3NH2

1.123

Boiling point

1.544520

Flash point 97

24.22

196

Solubility in 100 parts solvent

0.48 aq25; s alc; misc chl, eth, HOAc

76

45

i aq; s alc, eth s hot alc

1.207

1.526320

1.152

1.576120

2

215

12, 836

1.587420

2

141.60

12, 988

1.583020

25

115– 112 11710mm 238 100

CH3(Cl)C6H3NH2

141.60

12, 835

1.584820

27

241

99

CH3(Cl)C6H3NH2

141.60

12, 835

1.584020

22

237

160

C6H5CH(CH3)C6H3(Cl)OH

232.71

64, 4710

(CH3)2CHCH2CH2Cl

106.59

1, 135

186 98

s alc

s hot alc

1552mm 0.870420 4

1.408420

104

99

16

sl s aq; misc alc, eth

c149 c150 c151 c152 c153 c154 c155 c156 c157 c158 c159 c160

2-Chloro-2-methylbutane Chloromethyldimethylchlorosilane Chloromethyl 2,2-dimethylpropionate Chloromethyl ethyl ether Chloromethylmethyldichlorosilane Cloromethylmethyldiethoxysilane Chloromethyl methyl ether Chloromethyl methyl sulfide 1-(Chloromethyl)naphthalene 4-Chloro-2-methylphenol 4-Chloro-3-methylphenol 4-Chloro-N-methylpiperidine HCl

1.405220

143.1

1.086520 4

1.436020

150.61

1.045

1.417020

1.0420 4

1.404020

79–83

106.59

(CH3)2Si(Cl)CH2Cl (CH3)3CCOOCH2Cl ClCH2OCH2CH3

73.7

0.865020 4

CH3CH2CCl(CH3)2

94.54

1, 134

12, 645

85

40

163.5

1.285820 4

1.450020

121–122

ClCH2Si(OC2H5)2CH3

182.7

1.00020 4

1.40725

160–161

1.070320 4

1.396120

1.153

1.496320

80.51

ClCH2SCH3

95.48

C10H7CH2Cl

176.65

5, 566

CH3(Cl)C6H3OH

142.59

CH3(Cl)C6H3OH

142.59

Chloromethylbenzenes, c244, c245, c246

1, 580

1.638020

i aq; s alc, eth

115–116

ClCH2Si(CH3)Cl2

ClCH2OCH3

16

103.5

57–59

s alc; v s eth

15

d aq; s acet, CS2

105 112

32

16925mm

6, 359

48

225

sl s aq

6, 381

68

235

i aq; s alc, bz, chl, eth, acet

170.08

164

(Chloromethyl)oxirane, c101

Chloromethyl pivalate, c151

1.161

1.162

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c161

Name

1-Chloro-2-methylpropane c162 2-Chloro-2-methylpropane c163 1-Chloro-2-methylpropene c164 3-Chloro-2-methylpropene c165 Chloromethyltrichlorosilane c166 Chloromethyltrimethylsilane c167 6-(Chloromethyl)uracil c168 1-Chloronaphthalene c169 2-Chloronaphthalene c170 4-Chloro-1,8-naphthalic anhydride c171 4-Chloro-3-nitroacetophenone c172 2-Chloro-4-nitroaniline c172a 2-Chloro-5-nitroaniline c173 4-Chloro-2-nitroaniline c174 4-Chloro-3-nitroaniline

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

(CH3)2CHCH2Cl

92.57

1, 124

0.882915

1.401015

130.3

68.9

21

(CH3)3CCl

92.57

1, 125

0.847415 4

1.385620

25.4

50.8

18

(CH3)2C ¨ CHCl

90.55

1, 209

0.918620 4

1.422520

68.1

1

0.09 aq; misc alc, eth sl s aq; misc alc, eth misc alc, eth

ClCH2C(CH3) ¨ CH2

90.55

1, 209

0.921015 4

1.427220

72

10

misc alc, eth

1.46520 4

1.455520

117–118

0.886120 4

1.418020

99

1

259.3 256

121

80

ClCH2SiCl3

183.9

ClCH2Si(CH3)3

122.7

43, 1844

160.56

231, 328

162.62 162.62 232.63

5, 541 17, 522

2.3 59.5 210

C10H7Cl C10H7Cl

257 d 1.193820 4 1.137771

1.633220 1.607971

s alc, bz, PE s alc, bz, chl, eth

ClC6H3(NO2)C( ¨ O)CH3 ClC6H3(NO2)NH2

199.60

73, 995

101

172.57

12, 733

109

ClC6H3(NO2)NH2

172.57

12, 732

114

ClC6H3(NO2)NH2

172.57

12, 729

119

v s alc, eth

ClC6H3(NO2)NH2

172.57

12, 731

101

v s alc; s eth

sl s aq; v s alc, eth

c175 c176 c177 c178 c179 c180 c181 c182 c183 c184

1-Chloro-2-nitrobenzene 1-Chloro-3-nitrobenzene 1-Chloro-4-nitrobenzene 2-Chloro-4-nitrobenzoic acid 2-Chloro-5-nitrobenzoic acid 4-Chloro-3-nitrobenzoic acid 4-Chloro-3-nitrobenzophenone 2-Chloro-5-nitrobenzotrifluoride 4-Chloro-3-nitrobenzotrifluoride 5-Chloro-2-nitrobenzotrifluoride

Chloronicotinic acids, c234, c235

ClC6H4NO2

157.56

5, 241

1.348

32–33

246

123

s alc, bz, eth

ClC6H4NO2

157.56

5, 243

1.53420 4

46

236

103

sl s alc; v s eth, chl

ClC6H4NO2

157.56

5, 243

1.520

82–84

242

110

ClC6H3(NO2)COOH

201.57

9, 404

sl s alc; v s eth, CS2 s hot aq, hot bz

ClC6H3(NO2)COOH

201.57

9, 403

1.60818

168

ClC6H3(NO2)COOH

201.57

9, 402

1.64518

183

ClC6H3(NO2)C( ¨ O)C6H5 ClC6H3(NO2)CF3

261.66

71, 230

225.55

1.527

1.508320

ClC6H3(NO2)CF3

225.55

1.511

1.489320

ClC6H3(NO2)CF3

225.55

1.526

1.498020

141

sl s aq; s alc, bz, eth sl s alc; s hot aq

104–105 23513mm

-Chloronitrotoluene, n47

231

98

2.5

222

101

21–22

222–224

102

Chloronitro-,,-trifluorotoluenes, c182, c183, c184

1.163

1.164

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c185

c186 c187 c188 c189 c190 c191 c192 c193 c194 c195 c196 c197 c198

c199

Formula weight

Beilstein reference

ClC6H3(NO2)COC6H4COOH

305.68

10, 752

201

ClC6H3(NO2)OH

173.56

6, 240

106

ClC6H3(NO2)CH3

171.58

5, 329

1.547070

61

260

ClC6H3(NO2)CH3

171.58

5, 327

1.537770

36

238

125

i aq

ClC6H3(NO2)CH3

171.58

5, 329

1.297

1.558020

7

260745mm

112

i aq

CH3(CH2)7Cl CH3(CH2)4Cl

148.68 106.60

1, 159 1, 130

0.87520 4 0.882420 4

1.429820 1.411820

61 99.0

183 98.3

54 12

5-Chloro-2-pentanone 3-Chloroperoxybenzoic acid 2-Chlorophenol 3-Chlorophenol 4-Chlorophenol

ClCH2CH2CH2COCH3 ClC6H4C(O)OOH

120.58 172.57

12, 738

1.057118 4

1.437520

7220mm

62

i aq; v s alc, eth 0.02 aq; misc alc, eth s acet, eth

ClC6H4OH ClC6H4OH ClC6H4OH

128.56 128.56 128.56

6, 183 6, 185 6, 186

175–176 214 220

63 112 115

4-Chlorophenoxyacetic acid 2-(4-Chlorophenoxy)2-methylpropionic acid DL-2-(4-Chlorophenoxy)propionic acid

ClC6H4OCH2COOH

186.59

6, 187

ClC6H4OC(CH3)2COOH

214.65

ClC6H4OCH(CH3)COOH

200.62

Name o-(4-Chloro-3-nitrobenzoyl)benzoic acid 2-Chloro-4-nitrophenol 2-Chloro-4-nitrotoluene 2-Chloro-6-nitrotoluene 4-Chloro-3-nitrotoluene 1-Chlorooctane 1-Chloropentane

Formula

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

i aq; s alc, eth

94 d 1.257325 4 1.24525 4 1.223878 4

1.557920 1.556540 1.541945

9.3 33.5 43.5 159 122

63, 695

117

sl s aq; v s alc, eth sl s aq; s alc, eth sl s aq; v s alc, chl, eth

c200 c201 c202 c202 c204 c205 c206 c207

c208

4-Chlorophenylacetic acid p-Chlorophenylacetonitrile 2-Chloro-p-phenylenediamine sulfate 4-Chloro-1,2-phenylenediamine 4-Chloro-1,3-phenylenediamine 3-Chlorophenylhydrazine HCl 4-Chlorophenyl isocyanate 4-Chlorophenyl phenyl sulfone

ClC6H4CH2COOH

170.60

9, 448

105

ClC6H4CH2CN

151.60

9, 448

30.5

H2NC6H3(Cl)NH2· H2SO4 ClC6H3(NH2)2

240.67

13, 117

253

142.59

13, 25

70

H2N(Cl)C6H3NH2

142.59

13, 53

90

ClC6H4NHNH2·HCl

179.05

15, 424

242 d

ClC6H4NCO

153.57

12, 616

ClC6H4SO2C6H5

252.72

61, 149

ClC6H4SiCl3

246.0

ClC6H3(COOH)2

200.58

9, 816

1.561820

31

v s aq, alc, eth; s bz 267

204

110

94 1.431620 4

1.541820

74 acet; 44 bz; 5 CCl4; 65 diox; 21 i-PrOH

c210

4-Chlorophenyltrichlorosilane 4-Chloro-o-phthalic acid 1-Chloropropane

CH3CH2CH2Cl

78.54

1, 104

0.898515

1.388020

122.8

46.6

18

c211

2-Chloropropane

CH3CHClCH3

78.54

1, 105

0.856320

1.377720

117.2

35

35

c212

3-Chloro-1,2propanediol 1-Chloro-2-propanol 3-Chloro-1-propanol

ClCH2CH(OH)CH2OH

1.321820 4

1.480520

213

58

1.11520 1.130920 4

1.437520 1.446020

126–127 160–162

51 73

c209

c213 c214

CH3CH(OH)CH2Cl ClCH2CH2CH2OH

1.165

p-Chlorophenacyl bromide, b246 Chlorophenylamines, c33, c34, c35

110.54 94.54 94.54

1, 363 1, 356

115– 11720mm 148

4-Chlorophenyl sulfone, b165 4-Chlorophenyl sulfoxide, b166

Chloropicrin, t239 Chloroprene, c216

0.27 aq; misc alc, eth 0.34 aq; misc alc, eth s aq, alc, eth misc aq; s alc

1.166

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

c215

Chloro-2-propanone

ClCH2COCH3

92.53

1, 653

1.13515 4

1.435020

44.5

119.7

7

c216

3-Chloro-1-propene

ClCH2CH ¨ CH2

76.53

1, 198

0.93920 4

1.415120

134.5

45.2

28

c217

(3-Chloropropenyl)benzene 2-Chloropropionic acid 3-Chloropropionic acid 3-Chloropropionitrile 2-Chloropropionyl chloride 3-Chloropropionyl chloride p-Chloropropiophenone 3-Chloropropylamine HCl 3-Chloropropylmethyldichlorosilane 2-Chloropropyl(phenyl)dichlorosilane N-(3-Chloropropyl)piperidine HCl

C6H5CH ¨ CHCH2Cl

152.62

52, 372

1.584520

19

10812mm

79

CH3CH(Cl)COOH

108.52

2, 248

186

101

misc aq, alc, eth

ClCH2CH2COOH

108.52

2, 249

41

205

112

v s aq, alc, chl

89.53

2, 250

1.144318

1.437920

50

176

75

CH3CH(Cl)COCl

126.97

2, 248

1.308

1.440020

111

31

d aq, alc

ClCH2CH2COCl

126.97

2, 250

1.330713

1.457020

145

61

i aq; d hot aq, hot alc; s alc; v s eth

ClC6H4C( ¨ O)CH2CH3

168.62

7, 301

37

ClCH2CH2CH2NH2·HCl

130.02

4, 148

150

Cl(CH2)3Si(CH3)Cl2

191.6

1.204520 4

1.458020

7015mm

Cl(CH2)3SiCl2(C6H5)

253.6

1.24120 4

1.533220

14110mm

c218 c219 c220 c221 c222 c223 c224 c225

c226

c227

ClCH2CH2CN

198.14

20, 18

1.182

1.434520

220

971mm

10 aq; misc alc, chl 0.36 aq; misc alc, chl

c228 c229 c229 c231 c232 c233 c234 c235 c236 c237 c238 c239 c240

3-Chloropropyl thiolacetate 3-Chloropropyltrichlorosilane 3-Chloropropyltriethoxysilane 3-Chloropropyltrimethoxysilane 3-Chloropropyne

CH3C( ¨ O)SCH2CH2CH2Cl

152.64

ClCH2CH2CH2SiCl3

212.0

Cl(CH2)3Si(OC2H5)3

240.8

Cl(CH2)3Si(OCH3)3

198.72

ClCH2C ˜ CH

23, 493

1.00920 4

1.494620

8410mm

77

1.359020 4

1.466820

181.5

66

1.42020

10210mm

1.07725 4

1.418325

74.51

1, 248

1.030625 4

1.434920

1.20515

1.532020

2-Chloropyridine 2-Chloro-3-pyridinecarboxylic acid 6-Chloro-3-pyridinecarboxylic acid 2-Chloroquinoline 4-Chlorosalicyclic acid 5-Chlorosalicylic acid N-Chlorosuccinimide

ClC5H4N C5H3N(Cl)COOH

113.55 157.56

20, 230 222, 35

C5H3N(Cl)COOH

157.56

22, 43

HO(Cl)C6H3COOH

163.61 172.57

20, 359 10, 101

HO(Cl)C6H3COOH

172.57

10, 102

133.53

21, 380

Chlorosulfonyl isocyanate

ClSO2NCO

-Chloropropionaldehyde diethyl acetal, c82

1.159

141.53

78

183

66

58

18

166714mm

65

misc bz, alc, eth, EtAc sl s aq; s alc, eth

d 175 200 d 1.246425 4

1.625925

37 212

267

i aq; s alc, bz, eth

172 1.65 1.626

150–151 1.446720

3-Chloropropylene-1,2-oxide, c102

44

1.4 aq; 0.67 alc; 2 bz; sl s chl, eth 107

1-Chloro-2,5-pyrrolidinedione, c239

1.167

1.168

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

1.286

1.548320

1.082620 4

c241 c242 c243 c244

8-Chlorotheophylline 2-Chlorothiophene 4-Chlorothiophenol 2-Chlorotoluene

Cl ˆ C4H3S ClC6H4SH ClC6H4CH3

214.61 118.59 144.62 126.59

26, 473 17, 32 6, 326 5, 290

c245

3-Chlorotoluene

ClC6H4CH3

126.59

5, 291

c246

4-Chlorotoluene

ClC6H4CH3

126.59

5, 292

c247

N-Chloro-p-toluenesulfonamide, Na salt 4-Chloro-1toluenethiol 4-Chloro-o-tolyloxyacetic acid, Na salt 4-(4-Chloro-o-tolyloxy)butyric acid Chloro-2,2,2-trifluoroethane Chlorotrifluoroethylene Chlorotrifluoromethane Chlorotrimethylgermane Chlorotrimethylsilane

CH3C6H4SO2NClNa

227.67

ClC6H4CH2SH

158.65

6, 466

ClC6H3(CH3)OCH2COONa

222.61

63, 1265

ClC6H3(CH3)O(CH2)3COOH CF3CH2Cl

228.68 118.5

1.3890

CF2 ¨ CFCl

116.48

1.315

ClCF3

104.46

(CH3)3GeCl

153.16

1.238222

(CH3)3SiCl

108.64

0.858020 4

c248 c249

c250 c251 c252 c253 c254 c255

Melting point

Boiling point

Flash point

1.52502

d 290 72 51 34

129 207 159.0

47

1.076019 4

1.521820

48.9

161.8

50

1.069720 4

1.520820

7.2

162.0

49

22

167 d

1.202

1.589320

20

76

220–225

99–100 105

6.9

158.2

27.9

181

81.5

1.428320

13

102

1.388520

40

57

1.30900

13, 42

40

Solubility in 100 parts solvent s alk i aq; misc alc, eth sl s aq; v s alc, bz, chl, eth s alc, bz, chl; misc eth sl s aq; s alc, bz, eth s aq; i bz, chl, eth

c256

Chlorotriphenylmethane c257 Chlorotripropylsilane c257a Chlorotris(dimethylamino)silane c258 -Chloro-o-xylene c259 -Chloro-m-xylene c260 -Chloro-p-xylene

110–112 23020mm

(C6H5)3CCl

278.78

(C3H7)3SiCl

192.8

0.88220 4

1.44020

199–201

[(CH3)2N]3SiCl

195.8

0.97520 4

1.44220

62–6312mm

CH3C6H4CH2Cl CH3C6H4CH2Cl CH3C6H4CH2Cl

140.61 140.61 140.61

5, 364 5, 373 5, 384

1.063 1.06420

1.539120 1.535020 1.533020

199 195–196 200

73 75 75

ClC6H3(CH3)2

140.61

5, 363

1.047

223

66

c261

4-Chloro-o-xylene

c262

Cholesterol

386.66

c263

Cholic acid

408.58

-Chlorotoluene, b89 Chlorotoluidines, c142, c143, c144, c145, c146 2-Chlorotriethylamine, d272

5, 700

4.5

1.528320

1.06720 4

Chloro-,,-trifluorotoluenes, c51, c52, c53 4-Chloro-,,-trifluoro-o-toluidine, a144 -Chloro-,,-trifluoro-m-xylene, t299

148.5 198

360 sl d

v s bz, chl, eth

i aq; misc alc, eth i aq; misc alc, eth misc alc, bz, eth, acet misc alc, bz, eth, acet 1.29 alc; 35 eth; 22 chl; s bz, PE 0.028 aq; 0.06 alc; 2.8 acet; 0.036 bz; 0.5 chl

Chlorotrihexylsilane, t302 Chloroxylenol, c90

1.169

1.170

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

c264

Cinchonine

c265 c266

1,8-Cineole trans-Cinnamaldehyde trans-Cinnamic acid

c267 c268

Formula weight

Beilstein reference

294.40

232, 369

C6H5CH ¨ CHCHO

154.25 132.16

17, 23 7, 348

0.92125 25 1.05025 25

C6H5CH ¨ CHCOOH

148.16

9, 573

1.247544

C6H5CH ¨ CHCOCl

166.61

92, 390

1.161725 4

C6H5CH ¨ CHCH2OH CH3C(COOH) ¨ CHCOOH

134.18 130.10

6, 570 2, 768

112.08 155.11

Formula

Refractive index

Melting point

Boiling point

1.457220 1.621920

174.4 246

134

300

1.61443

35–36

258

1.039735 35 1.62

1.575833

33 92 d

250.0

17, 440 22, 254

1.247

1.471220

192.12

3, 556

1.665

8 214 carbonizes without melting 300 154

156.27

1, 451

0.857020 4

c269 c270 c271 c272

Citraconic anhydride Citrazinic acid

c273

Citric acid

c274

Citronellol

c275

Cocaine

303.35

222, 150

c276

Coumarin

146.15

17, 328

Flash point

~260 1.5 7.5

trans-Cinnamoyl chloride Cinnamyl alcohol Citraconic acid

HOOCCH2C(OH)(COOH)CH2COOH (CH3)2C ¨ CHCH2CH2CH(CH3)CH2CH2OH

Density

1.455620 1.502298

0.93520 4

222 98

1870.1mm

69

298

71

Solubility in 100 parts solvent 1.4 alc; 0.9 chl; 0.2 eth misc alc, chl, eth 0.014 aq; misc alc, chl, eth 0.05 aq; 16 alc; 8 chl s hot alc, CCl4 s aq; v s alc, eth v s aq, alc, eth; sl s chl; i bz, PE

101 i aq; s alk

59 aq 79 0.17 aq; 15 alc; 140 chl; 28 eth 0.25 aq; v s alc, chl, eth

c277

Creatine

c278 c279

Creatinine o-Cresol

c280

131.14

4, 363

CH3C6H4OH

113.12 108.14

24, 245 6, 349

1.027341

1.536141

255 d 30.9

190.8

81

m-Cresol

CH3C6H4OH

108.14

6, 373

1.03420 4

1.543820

12.2

202.7

86

c281

p-Cresol

CH3C6H4OH

108.14

6, 389

1.017941

1.531241

34.8

201.9

86

c282 c283 c284

trans-Crotonaldehyde Crotonyl chloride Cupferron

CH3CH ¨ CHCHO CH3CH ¨ CHCOCl C6H5N(NO)ONH 4

70.09 104.54 155.16

1, 728 2, 411 161, 395

0.851620 1.091

1.437320 1.459520

76.5

104.1 123

8 35

Chromone, b56 Chromotropic acid, d396 Chrysoldin, d31 Cinchophen, p149 Cinnamyl chloride, c217 Citral, d562, d563 Cleland’s reagent, d424 2,4,6-Collidine, t367

HOOCCH2N(CH3)C( ¨ NH)NH2

300

p-Coumaric acid, h107 Cresotic acids, h137, h138 Cresylic acids, c279, c280, c281 Crotonic acid, b402 Crotononitrile, b400 Crotyl alcohols, b404, b405 Crotyl bromide, b240 Crotyl chloride, c68

1.3 aq; 0.11 alc; ith

163–164

8 aq; sl s alc; i eth 3.1 aq40; misc alc, chl, eth; s alk 2.5 aq40; misc alc, chl, eth; s alk 2.3 aq40; misc alc, chl, eth; s alk 18.1 aq v s aq, alc

12-Crown-4, t125 15-Crown-5, p45 18-Crown-6, h74 Cumene, i91 Cumic alcohol, i92 Cupron, b50

1.171

1.172

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density 1.28220 4

c285

Cyanamide

H2NCN

42.04

32, 63

c286 c287

2-Cyanoacetamide Cyanoacetic acid

NCCH2CONH2 NCCH2COOH

84.08 85.06

c288 c289

Cyanoacetohydrazide Cyanoacetylurea

99.09 127.10

c290

2-Cyanoethanol

NCCH2C( ¨ O)NHNH2 NCCH2C( ¨ O)NHC( ¨ O)NH2 NCCH2CH2OH

c291

NCCH2CH2Si(CH3)Cl2

168.1

CH3NHC( ¨ NCN)SNa

137.14

4, 71

C10H7CN NCCH2CH2CH2SiCl3

153.18 202.6

9, 649

c295

2-Cyanoethyldichloromethylsilane 1-Cyano-3-methylisothiourea, Na salt 1-Cyanonaphthalene 3-Cyanopropyltrichlorosilane 2-Cyanopyridine

NC(C5H4N)

104.11

22, 36

c296 c297 c298 c299

3-Cyanopyridine 4-Cyanopyridine Cyanotrimethylsilane Cyanuric acid

NC(C5H4N) NC(C5H4N) (CH3)3SiCN

104.11 104.11 99.21 129.08

22, 41 22, 46 26, 239

c300 c301 c302

Cyclobutane Cyclodecane Cyclododecanol

C4H8 C10H20 C12H23OH

56.10 140.27 184.32

5, 17

c292 c293 c293

71.08

Refractive index

Melting point

Boiling point

46

83380mm

2, 589 2, 583

119.5 65–67

10815mm

3, 66

110 214 d

32, 213

1.05880 1.20220 4

1.45520

Flash point

215 107

d

Solubility in 100 parts solvent 78 aq; 29 BuOH; 42 EtAc; s alc, eth 25 aq; 3.1 alc s aq, alc, eth; sl s bz v s aq; s alc; i eth

106– 10811mm 634mm

misc aq, alc; sl s eth

299 93– 948mm 215

i aq; v s alc, eth

290 d 1.111325 25 1.28025

1.629818 1.46525

38

1.528820

28

0.78320 4 1.7680

1.392420

52 240–245 80 11 114–117 d to HOCN

0.70380

1.37520 1.470720

90.7 77

12.5 201

89

s aq; v s alc, bz, eth v s aq, alc, bz, eth s aq, alc, bz, eth

1 0.5 aq; s hot alc, pyr; i acet, bz, chl, eth i aq; v s alc, acet 1

c303 c304

C12H22( ¨ O)

c311 c312

Cyclododecanone trans,trans,cis1,5,9-cyclododecatriene trans-Cyclododecene Cycloheptane DL-trans-1,2Cycloheptanediol Cycloheptanol Cycloheptanone 1,3,5-Cycloheptatriene Cycloheptene Cyclohexane

c313

Cyclohexane-d12

c305 c306 c307 c308 c309 c310

Cyanoacetonitrile, m5 Cyanoanilines, a124, a125, a126 Cyanobenzene, b51 2-Cyanoethanol, h169 Cyanoethylene, a64 Cyanomethane, a29

182.31 162.28

72, 48

0.906 0.892520 4

1.507020

0.863 0.81120 4

1.482220 1.445520

166.31 98.18 130.19

5, 29 63, 4086

114.19 112.17 92.13

6, 10 7, 13 5, 280

0.94820 4 0.949020 4 0.888

1.476020 1.461120 1.521120

C7H12 C6H12

96.17 84.16

5, 65 5, 20

0.82420 4 0.778620 4

1.458520 1.426220

C6D12

92.26

0.89

1.421020

C7H14 C7H12(OH)2 C7H13OH C7H12( ¨ O)

2-Cyanopropene, m27 Cyanuric chloride, t250 Cyclododecane epoxide, e4 Cyclododecanone isooxime, a318 Cycloheptanone isooxime, a317 Cycloheptyl bromide, b260

61 18

851mm 231

87

75.3

232–245 118.8 138– 13915mm 185 179–181 115.5

71 55 26

6.5

114.7 80.7

6 18

78

18

8.0 61–63 2

93 6

v s alc, eth

sl s aq; v s alc, eth i aq; v s alc; s eth s alc, eth; v s bz, chl s alc, eth 0.01 aq; misc alc, bz, acet, eth, CCl4

Cyclohexaneacetic acid, c333 Cyclohexanecarboxylic acid chloride, c316 2,5-Cyclohexadien-1,4-dione, b59 2,5-Cyclohexadiene-1,4-dione with 1,4benzenediol (1:1), q1 Cyclohexanemethanol, c342

1.173

1.174

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c314 c315 c316 c317 c318 c319 c320

c320

c322 c323 c324 c325 c326 c327

Name 1,3-Cyclohexanebis(methylamine) Cyclohexanecarbaldehyde Cyclohexanecarbonyl chloride Cyclohexanecarboxylic acid cis-1,2-Cyclohexanediamine trans-1,2-Cyclohexanediamine cis-1,2-Cyclohexanedicarboxylic anhydride cis-1,4-Cyclohexanedimethanol 1,3-Cyclohexanedione 1,2-Cyclohexanedione dioxime Cyclohexanemethylamine Cyclohexanepropionic acid Cyclohexanethiol Cyclohexanol

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

C6H10(NHCH3)2

142.25

C6H11CHO

112.17

7, 19

0.926

1.450020

163

40

C6H11COCl

146.62

9, 9

1.096

1.470020

184

66

C6H11COOH

128.17

7, 19

1.048015 4

1.453020

C6H10(NH2)2

114.19

13, 1

0.931

1.486420

9218mm

C6H10(NH2)2

114.19

13, 1

0.931

1.486420

9218mm

Solubility in 100 parts solvent

106

154.17 0.978100 4

29

232.5

34

15817mm

43

288

C6H10(CH2OH)2

144.21

C6H8( ¨ O)2 C6H8( ¨ NOH)2

112.13 142.16

7, 554 172, 526

1.086191

1.489320 supercooled 1.4576102

C6H11CH2NH2

113.20

12, 12

0.870

1.463020

C6H11CH2CH2COOH

156.23

9, 82

0.912

1.463620

14–17

275.8

C6H11SH C6H11OH

116.23 100.16

6, 8 6, 5

0.950 0.941630

1.492120 1.462930

25.2

158–160 161.1

0.21 aq; s alc, bz, eth

74

103–105 185–188

misc aq, alc; 2.5 eth s aq, alc, acet, chl s aq

145–147

43

43 67

3.8 aq25; misc alc, bz

45 to 47 89–91 103.5

155.7

46

206–210 83.0

12

53

168 218

61 86

98.15

7, 8

0.947820 4

1.451020

C6H10( ¨ NOH) C6H10

113.16 82.15

7, 10 5, 63

0.809420 4

1.446420

2-Cyclohexen-1-one 2,3-Cyclohexeneopyridine c332a [2-(3-Cyclohexenyl)ethyl]methyldichlorosilane c333 Cyclohexylacetic acid c334 Cyclohexylamine

C6H8( ¨ O)

96.13 133.19

72, 55 202, 176

0.993 1.025

1.488520 1.5440

C6H9CH2CH2Si (CH3)Cl2

223.2

1.07720 4

1.48125

C6H11CH2COOH

142.20

92, 9

1.007

1.463020

31–33

242–244

112

sl s aq; s org solv

99.18

12, 5

0.867120

1.459320

17.7

134.8

32

misc aq, alc, eth, chl

c335

C6H11NHCH2CH2SO3H

207.29

300

C6H11NHCH2CH2CH2SO3H

221.32

300

c328

Cyclohexanone

C6H10( ¨ O)

c329 c330

Cyclohexanone oxime Cyclohexene

c331 c332

c336

2-(Cyclohexylamino)ethanesulfonic acid 3-Cyclohexylamino-1propanesulfonic acid

C6H11NH2

Cyclohexanone cyanohydrin, h110 cis-4-Cyclohexene-1,2-dicarboximide, t75 cis-4-Cyclohexene-1,2-dicarboxylic anhydride, t74

Cyclohexene oxide, e5 N-(1-Cyclohexen-1-yl)morpholine, m450 N-(1-Cyclohexen-1-yl)pyrrolidine, p274

15 aq10; s alc, eth s aq, eth; sl s alc 0.02 aq; misc alc, bz, acet, eth v s alc

79–812mm

Cyclohexyl alcohol, c327

1.175

1.176

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c337 c338 c339 c340 c341 c342 c343 c344 c345 c346 c347 c348 c349 c350 c351 c352 c353 c354

Formula weight

Beilstein reference

Density

Refractive index

Melting point

C6H11C6H4NH2 C6H11C6H5 C6H11NHCHO

175.28 160.26 127.18

12, 1209 5, 503

0.950220 4

1.525820

53–56 5–6 38–40

C6H11NCO

125.17

122, 12

0.980

C6H11NCS

141.24

122, 12

C6H11CH2OH

114.19 167.25

6, 14

Name 4-Cyclohexylaniline Cyclohexylbenzene N-Cyclohexylformamide Cyclohexyl isocyanate Cyclohexyl isothiocyanate Cyclohexylmethanol N-Cyclohexyl-2pyrrolidinone Cyclohexyltrichlorosilane 1,5-Cyclooctadiene Cyclooctane Cyclooctanol Cyclooctanone Cyclooctene Cyclooctylamine Cyclopentamethylenedichlorosilane Cyclopentane Cyclopentanecarboxylic acid cis,cis,cis,cis-1,2,3,4Cyclopentanetetracarboxylic acid

Formula

Boiling point

Flash point

16613mm 239–240 13710mm

98

1.455120

168–170

48

0.996

1.535020

219

0.951225 4 1.026

1.464025 1.495

1.22220 4

1.47720

12

C6H11SiCl3

217.6

C8H16 C8H15OH

108.18 112.22 128.22

5, 116 5, 35 62, 25

0.881825 4 0.834 0.974020 4

1.490525 1.457420 1.485020

69 14.8 14–15

C6H14( ¨ O) C8H14 C8H15NH2

126.20 110.20 127.23 169.1

7, 21 51, 35

0.958420 4 0.846 0.928 1.55820 4

1.649420 1.469820 1.480420 1.467920

41–43 16 48

C5H10 C5H9COOH

70.13 114.14

5, 19 9, 6

0.746020 4 1.05320 4

1.406520 1.454020

93.9 4

C5H6(COOH)4

246.17

92, 724

192– 195 d

181 284 90– 9110mm 149–150 151.1 106– 10822mm 195–197 145–146 190 169–170 49.3 216

71

45 30 86

Solubility in 100 parts solvent

i aq; v s alc, eth

s alc, eth

s CCl4

25 62 37 93

i aq; misc alc, eth sl s aq; s MeOH

c355 c356

Cyclopentanol Cyclopentanone

C5H9OH C5H8( ¨ O)

86.13 84.12

6, 5 7, 5

c357

Cyclopentanone oxime Cyclopentene 2-Cyclopentene-1acetic acid 2,3-Cyclopenteneopyridine N-(1-Cyclopentene-1yl)morpholine 2-Cyclopentylidenecyclopentanone 3-Cyclopentylpropionic acid Cyclopropane

C5H8( ¨ NOH)

99.13

7, 7

C5H8 C5H7CH2COOH

68.11 126.16

5, 61 9, 42

c358 c359 c360 c361 c362 c363 c364

Cyclohexylbenzene, p104 Cyclohexyl bromide, b261 Cyclohexyl chloride, c77 Cyclohexyl ketone, c328 Cyclohexyl mercaptan, c326

C5H9CH2CH2COOH C3H6

0.948820 4 0.950918 4

1.452120 1.436620

19 58

140.9 130.6

53–55

196

135.1 19

0.774 1.047

1.422820 1.467520

119.17

1.018

1.544520

153.23

0.957

1.510520

150.22

1.001

1.523120

44.2 93– 942.5mm 87– 8811mm 105– 10612mm 14020mm

142.20

0.996

1.457020

13012mm

42.08

5, 15

0.72079 4

Cyclohexylmethane, m194 Cyclohexylmethyl bromide, b306 Cyclooctene oxide, e7a Cyclopentanepropanoic acid, c363 Cyclopentene oxide, e37

127.4

32.8

51 30

sl s aq; s alc sl s aq; misc alc, eth s aq, alc, bz, chl, eth

28 112 67 60 103 46 37 mL per 100 mL aq15; v s alc, eth

Cyclopentyl bromide, b263 Cyclopentyl chloride, c79 Cyclopropyl bromide, b264 Cyclopropyl cyanide, c365

1.177

1.178

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. c365 c366 c367 c368 c369 c370 c371

Cyclopropanecarbonitrile Cyclopropanecarbonyl chloride Cyclopropanecarboxylic acid Cyclopropyl methyl ketone Cystamine dihydrochloride L-()-Cysteine L-Cystine

d1

cis-Decahydronaphthalene

d2

d6 d7 d8 d9

trans-Decahydronaphthalene Dehydro-2-naphthol Decamethylcyclopentasiloxane Decamethyltetrasiloxane Decanal Decane 1,10-Decanediamine Decanedioic acid

d10

1,10-Decanediol

d3 d4 d5

Beilstein reference

Density

Refractive index

67.09

9, 4

0.91116

1.420720

135

32

C3H5COCl

104.54

9, 4

1.152

1.452220

119

23

C3H5COOH

86.09

9, 4

1.008

1.438020

182–184

71

C3H5COCH3

84.12

7, 7

0.899320 4

1.424120

114

21

Name

Formula C3H5CN

Formula weight

Melting point

17–19

Boiling point

Flash point

Solubility in 100 parts solvent s eth

sl s hot aq; s alc, eth s aq, alc, eth

H2NCH2CH2SSCH2CH2NH22HCl HSCH2CH(NH2)COOH HOOCCH(NH2)CH2SSCH2CH(NH2)COOH C10H18

225.20

4, 287

217 d

121.16 240.30

4, 506 4, 507

220 d d 240

138.26

5, 92

0.896320 4

1.481020

43.0

195.8

58

C10H18

138.26

52, 56

0.870020 4

1.469720

30.4

187.3

52

C10H17OH [ ˆ Si(CH3)2O ˆ ]5

154.25 370.8

6, 67

0.996 0.95920 4

1.4992 1.398220

38

10914mm 10120mm

112

(CH3)3SiO[Si(CH3)2O]2Si(CH3)3 H(CH2)9CHO CH3(CH2)8CH3 H2N(CH2)10NH2 HOOC(CH2)8COOH

310.7

0.853620 4

1.388020

70

194–195

86

sl s alc; s bz, PE

156.27 142.29 172.32 202.25

1, 711 1, 168 4, 273 2, 718

0.83015 4 0.730120 4

1.428020 1.411920

i aq; s alc, eth 0.07 aq

1.422134

207–209 174.1 14012mm 295100mm

85 46

1.20720 4

29.7 62–63 134.5

HO(CH2)10OH

174.28

12, 560

72–75

1708mm

v s aq, alc; i bz, eth 0.01 aq; s acid, alk; i alc v s alc, chl, eth; misc most ketones, esters see under cis isomer i aq

0.1 aq; v s alc, esters, ketones sl s aq, eth; v s alc

d11

d14

Decanedioyl dichloride Decanenitrile 1-Decanesulfonic acid, Na salt Decanoic acid

d15 d16

1-Decanol 4-Decanone

d17 d18 d19

Decanoyl chloride 1-Decene Decylamine

d20 d21

Dehydroabietylamine Dehydroacetic acid

d22

Deoxybenzoin

d12 d13

Cymenes, i100, i101, i102 4-Cymylphenol, m359 Cysteamine, a162 Cysteic acid hydrate, a288 Cytosine, a198

112

ClC(O)(CH2)8COCl

239.14

2, 719

1.121220 4

1.467820

CH3(CH2)8CN CH3(CH2)9SO3Na

153.27 244.33

2, 356 43, 27

0.829515 4

1.429520

15 300

235–237

misc alc, chl, eth

CH3(CH2)8COOH

172.27

22, 309

0.878250 4

1.428840

31.4

270

CH3(CH2)9OH CH3(CH2)5C( ¨ O)(CH2)2CH3 CH3(CH2)8C( ¨ O)Cl CH3(CH2)7CH ¨ CH2 CH3(CH2)9NH2

158.29 156.27

1, 425 1, 711

0.829720 4 0.82420 0

1.437120 1.423720

6.9

230.2 207

82 71

0.015 aq; s alc, chl, bz, eth, CS2 i aq; s alc, eth i aq; misc alc, eth

190.71 140.27 157.30

2, 356 13, 858 4, 199

0.919 0.740820 4 0.787

1.441020 1.421520 1.436020

34.5 66.3 12–14

965mm 170.6 216–218

98 47 85

285.48 168.15

17, 559

196.25

7, 431

C6H5CH2C( ¨ O)C6H5

22075mm

111–113 269.9

2,4-D, d214 p,p-DDT, b167 1,2-Decahydroacenaphthylene, a2 Decamethylene glycol, d10 1,10-Decadedicarboxylic acid, d721

d aq, alc; s eth i aq; misc alc, eth sl s aq; misc alc, bz, eth, acet

112

1.546020 1.20104

d aq, alc

55–56

320 Decyl aldehyde, d6 Decyl chloride, c80 Decyl iodide, i33 Dextrose, g6

22 acet; 18 bz; 5 MeOH i aq; v s alc, eth

1.179

1.180

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d23 d24 d25 d26 d27 d28 d29 d30 d31 d32 d33 d34 d35 d36 d37 d38

Name Diacetoxydimethylsilane Diacetoxymethylphenylsilane Diallylamine Diallyl ether Diallyl sulfide 1,2-Diaminoanthraquinone 1,4-Diaminoanthraquinone 2,6-Diaminoanthraquinone 2,5-Diaminoazobenzene HCl 2,5-Diaminobenzenesulfonic acid 3,5-Diaminobenzoic acid 4,4-Diaminodiphenylamine sulfate 4,4-Diaminodiphenylmethane 3,3-Diaminodiphenyl sulfone 4,4-Diaminodiphenyl sulfone 2,7-Diaminofluorene

Formula

Formula weight

(CH3)2Si(OOCCH3)2

176.3

CH3(C6H5)Si(OCOCH3)2 (H2C ¨ CHCH2)2NH (H2C ¨ CHCH2)2O (H2C ¨ CHCH2)2S

238.3

Beilstein reference

Density

Refractive index

1.05420 4

1.403020

164–166

1.48720

1276mm

0.787 0.80518 0 0.887727 4

1.440520 1.424020 1.488920

Melting point

88

Boiling point

Solubility in 100 parts solvent

97.16 98.15 114.21

4, 208 12, 477 1, 440

238.25

141, 459

289–291

i aq; misc alc, eth sl s aq; misc alc, eth sl s alc, eth

238.25

14, 197

265–268

sl s aq, alc; v s bz

238.25

14, 215

325

sl s hot aq, pyr

C6H5N ¨ NC6H3(NH2)2HCl (H2N)2C6H3SO3H

248.72

16, 383

235 d

188.21

14, 713

298 d

(H2N)2C6H3COOH

152.15

14, 453

228

H2NC6H4NHC6H4NH2H2SO4 H2NC6H4CH2C6H4NH2

297.33

13, 110

300

198.27

13, 238

91–92

H2NC6H4SO2C6H4NH2

248.30

13, 426

167–170

H2NC6H4SO2C6H4NH2

248.30

13, 536

175–177

196.25

13, 266

165–166

83

111–112 94 138

Flash point

15 46

sl s aq, alc H2O, 110

398

sl s aq; s alc, eth

221

sl s aq; v s alc, bz, eth i aq; s alc, bz i aq; s alc, acet, HCl sl s aq; v s alc

d39 d40 d41 d42

2,4-Diamino-6hydroxypyrimidine Diaminomaleonitrile 1,8-Diamino-pmenthane 3,3-Diamino-Nmethyldipropyamine

Diacetins, g17, g18 Diacetone acrylamide, d568 Diacetone alcohol, h142 Diacetonitrile, a151 (Diacetoxyiodo)benzene, i28 Diacetyl, b386

NCC(NH2) ¨ C(NH2)CN

CH3N[(CH2)3NH2]2

126.12

24, 469

108.10 170.30

42, 949 13, 4

145.25

44, 1279

285 d

0.914

1.480520

Diallyl, h41 2,5-Diaminoanisole, m94 1,4-Diaminobutane, b379 1,2-Diaminocyclohexanes, c318, c319 1,10-Diaminodecane, d8 p-Diaminodiphenyl, b136

178–179 45 107– 93 12510mm 110– 102 1126mm

3,3-Diaminodipropylamine, i9 1,12-Diaminododecane, d720 1,2-Diaminoethane, e15 1,7-Diaminoheptane, h7 1,6-Diaminohexane, h56

s aq

1.181

1.182

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d43 d44 d45

d46 d47

d48

Name 1,3-Diamino-2propanol 2,6-Diaminopyridine 1,4-Diazabicyclo[2.2.2]octane 1,8-Diazabicyclo[5.4.0]undec-7-ene Diazomethane

d52 d53

1-Diazo-2-naphthol4-sulfonic acid, Na salt Dibenz[de,kl ]anthracene Dibenzofuran 2,3,11,12-Dibenzo1,4,7,10,13-hexaoxacyclooctadeca2,11-diene Dibenzothiophene Dibenzoylmethane

d54

Dibenzoly peroxide

d49 d50 d51

Formula H2NCH2CH(OH)CH2NH2 (H2N)2C5H3N

Formula weight 90.13 109.13 112.18

Beilstein reference

C6H5C( ¨ O)CH2C( ¨ O)C6H5 C6H5C(O)O ˆ OC(O)C6H5

Refractive index

Melting point 40–45

221, 647

118–120 158 174

1.018

1.521920

42.04

23, 25

145

272.22

16, 595

166

252.32

51, 363

1.35

168.20 360.41

17, 70

1.088699 4

184.26 224.26

17, 72 7, 769

242.23

Boiling point

4, 290

152.24 CH2 ¨ N ¨ N

Density

1.607999

Flash point

Solubility in 100 parts solvent

235 s aq, alc 45 aq; 77 EtOH; 51 bz; 13 acet; 26 MeEtKe

800.6mm

112

23

very s eth, diox explosive

273–274 503

s bz; sl s alc, eth

81–83 285 162–164

i aq; s alc, bz, eth

97.100 78–79

s aq; v s alc, bz s alc; v s eth

332–333 22018mm

103–106 may explode when heated

sl s aq, alc; s bz, chl, eth

d55

d56 d57 d58

( ˆ )-Dibenzoyl-Ltartaric acid hydrate Dibenzylamine Dibenzyl disulfide Dibenzyl ether

[(C6H5COOCH(COOH) ˆ ]2  H2O

376.34

9, 170

C6H5CH2NHCH2C6H5 C6H5CH2SSCH2C6H5 C6H5CH2OCH2C6H5

197.28 246.39 198.27

12, 1035 6, 465 6, 434

1,3-Diamino-2-hydroxypropane, d43 Diaminonaphthalenes, n4, n5 1,2-Diamino-4-nitrobenzene, n68 1,4-Diamino-2-nitrobenzene, n67 1,9-Diaminononane, n93 1,8-Diaminooctane, o23 1,5-Diaminopentane, p29 2,5-Diaminopentanoic acid, o46 1,2-Diaminopropane, p192

1.026

1.573120

1.001420 4

1.561020

1,3-Diaminopropane, p193 4,6-Diamino-4-pyrimidinol, d39 Diaminotoluenes, t168, t169, t170, t171 1,3-Diaminourea, c11 4,5-Diamino-o-xylene, d586 Diamylamine, d650 Diamyl ether, d651 Diamyl ketone, u6 1,2-Dianilinoethane, d669

26 69 3.5

300 d  270 298 d

143 135

i aq; s alc, eth s hot alc, bz, eth misc alc, acet, chl, eth

Diazoacetic ester, e114 1,3-Diazole, i4 Dibenzo-18-crown-6, d51 Dibenzo[b,e]pyridine, a61 Dibenzopyrrole, d665 Dibenzoyl, b34 Dibenzyl, d666

1.183

1.184

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point 112

(C6H5CH2NHCH2 ˆ )2

240.35

12, 1067

1.02420 4

1.562420

26

d60 d61 d62

N,N-Dibenzylethylenediamine Dibenzyl malonate Dibenzyl phosphonate Dibromoacetic acid

CH2[COOCH2C6H5]2 (C6H5CH2O)2P(O)H Br2CHCOOH

284.31 262.25 217.86

6, 436

1.137 1.187

1.544720 1.554020

d63

Dibromoacetonitrile

Br2CHCN

198.86

2, 219

2.296

1.539320

d64

2,4-Dibromoacetophenone 1,4-Dibromobenzene

BrC6H4C( ¨ O)CH2Br

277.96

7, 285

1880.2mm 112 5 to 5 1100.01mm 112 128– 13016mm 67– none 6924mm 108–110

C6H4Br2

235.92

5, 211

0.9641100 1.5743100

87.3

BrC6H4C6H4Br CH3CH(Br)CH2CH2Br BrCH2CH2CH2CH2Br BrCH2C( ¨ O)C( ¨ O)CH2Br HOCH2C(Br) ¨ C(Br)CH2OH HCClBr2

312.00 215.93 215.93 243.89

5, 580 1, 120 1, 120 1, 774

1.80020 1.808020 4

162–163 355–360 175 20 198 116–117

245.91

11, 260

208.29

1, 67

FCCl(Br)C(Br)F2

276.5

Br(CH2)10Br CH2BrC(Br)F2

300.09 223.87

Br2CF2

209.81

d59

d65 d66 d67 d68 d69 d70 d71 d72

d73 d74 d75

4,4-Dibromobiphenyl 1,3-Dibromobutane 1,4-Dibromobutane 1,4-Dibromo-2,3butanedione trans-2,3-Dibromo-2butene-1,4-diol Dibromochloromethane 1,2-Dibromo-2chloro-1,1,2-trifluoroethane 1,10-Dibromodecane 1,2-Dibromo-1,1difluoroethane Dibromodifluoromethane

2, 218

1.508520 1.518620

1954mm

219

none

Solubility in 100 parts solvent v s alc, bz, chl, eth

s warm alc, eth

none 112

1.4 alc; s bz; 101 eth s bz; sl s hot alc s chl, eth s chl

none

misc alc, bz, eth

112–114 22

2.451

1.546520

120748mm

2.247820

1.427520

11, 64 1, 92

1.33530 2.223820

1.491220 1.445620

27 61.3

16015mm 93.4

112

sl s alc; s eth i aq

11, 16

2.28815 4

1.399912

141.6

23–24

none

0.1 aq; misc alc, bz, chl, eth

93–94

d76 d77 d78 d79 d80 d81 d82 d83 d84 d85

1,3-Dibromo-5,5-dimethylhydantoin 1,1-Dibromoethane 1,2-Dibromoethane (1,2-Dibromoethyl)benzene cis-1,2-Dibromoethylene trans-1,2-Dibromoethylene 1,2-Dibromoethyltrichlorosilane 4,5,-Dibromofluorescein 2,4-Dibromo-1-fluorobenzene 1,2-Dibromohexafluoropropane

Dibenzyl ketone, d684

285.93

197 d 2.05520 4 2.180220 4

CH3CHBr2 BrCH2CH2Br

187.87 187.87

1, 90 1, 90

C6H5CH(Br)CH2Br

263.97

5, 356

BrCH ¨ CHBr

185.86

1, 190

2.2117 4

BrCH ¨ CHBr

185.86

1, 190

BrCH2CH(Br)SiCl3

321.3 490.12

Br2C6H3F

253.91

CF3CF(Br)C(Br)F2

309.83

1.537920 1.541615

10.0

113 131.7

70–74

14015mm

1.543118

53

112.5

2.246

1.550518

6.5

108

2.04620 4

1.53720

19, 228

none

s alc, bz, chl, eth

9011mm 270–273

2.04720

5,7-Dibromo-8-quinolinol, d87

i aq; v s alc, eth 0.43 aq; misc alc, eth

1.584020

s hot alc, HOAc 10522mm

72.8

92

1.185

1.186

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

1,6-Dibromohexane 5,7-Dibromo-8hydroxyquinoline Dibromomethane

Br(CH2)6Br

243.98 302.96

1, 145 21, 97

1.58618 4

1.506620

243 200–201 subl

32

misc eth s alc, bz; v s eth

CH2Br2

173.85

1, 67

2.495620 4

1.541920

52.7

none

Br2C6H2(NO2)NH2

295.93

12, 743

206–208

Br2C6H3NO2

280.91

5, 250

1.9581111

82–84

s bz, hot alc

d91 d92

2,6-Dibromo-4-nitroaniline 2,5-Dibromonitrobenzene 1,5-Dibromopentane 1,2-Dibromopropane

1.15 aq; misc alc, bz, acet, chl, eth sl s aq; s HOAc

Br(CH2)5Br CH3CH(Br)CH2Br

229.95 201.90

1, 131 1, 109

1.687915 4 1.93320

1.509215 1.520320

34 55.5

11015mm 139.6

d93 d94

1,3-Dibromopropane 2,3-Dibromopropanol

BrCH2CH2CH2Br BrCH2CH(Br)CH2OH

201.90 217.90

1, 110 1, 357

1.971225 4 2.12020 4

1.523320 1.559920

34

166.8 54 95–9710mm

d95 d96

2,3-Dibromopropene 2,3-Dibromopropionic acid 2,6-Dibromopyridine DL-2,3-Dibromosuccinic acid 1,2-Dibromotetrachloroethane 1,2-Dibromotetrafluoroethane 2,5-Dibromothiophene ,-Dibromotoluene 1,2-Dibromo-1,1,2trifluoroethane

BrCH2C(Br) ¨ CH2 BrCH2CH(Br)COOH

199.88 231.88

1, 201 2, 258

1.933620 4

1.547020

Br2(C5H3N) HOOCCH(Br)CH(Br)COOH BrCCl2CCl2Br

236.91 275.89

202, 153 2, 625

325.65

1, 93

BrCF2CF2Br

259.83

Br2C4H2S C6H5CHBr2 HC(Br)FC(Br)F2

241.94 249.94 241.8

d86 d87 d88 d89 d90

d97 d98 d99 d100 d101 d102 d103

17, 33 5, 308 1, 92

64–66

96.97

140–143 16020mm

79 none

none s aq, alc, bz

118–119 255 167 2.713

220–222

0.2 aq; misc alc, bz, chl, eth 0.17 aq; s alc, eth sl s aq; misc alc, bz, eth, acet

v s aq, alc none

2.16325

1.36725

110.5

47.3

2.14723 23 1.51015 2, 27427

1.628920 1.614720 1.419124

6

221 15623mm 76.5

110

i aq; v s alc, eth i aq; misc alc, eth

d106

,Dibromo-oxylene ,-Dibromo-pxylene 1,2-Dibutoxyethane

d107 d108

d104

C6H4(CH2Br)2

263.97

5, 366

1.960

92–94

sl s alc, chl, eth

C6H4(CH2Br)2

263.97

5, 385

2.0120

142–143 245

v s alc, chl; s eth

C4H9OCH2CH2OC4H9

174.28

Dibutylamine

(C4H9)2NH

129.25

0.2 aq; misc alc, acet 0.47 aq; s alc, acet, eth, EtAc, PE

(C4H9)2NCH2CH2OH

173.29

d109

N,N-Dibutylaminoethanol N,N-Dibutylaniline

C6H5N(C4H9)2

205.34

d110

Dibutyl decanedioate

314.45

d111

Di-tert-butyldicarbonate 2,5-Di-tert-butyl1,4-dihydroxybenzene Dibutyl disulfide

C4H9OOC(CH2)8COOC4H9 (CH3)3COC(O)OC(CH3)3 [(CH3)3C]2C6H2(OH)2

222.33

C4H9SSC4H9

178.36

d105

d112

d113

Dibutyl 1,2-benzenedicarboxylate, d128

0.837420 20

1.413120

69.1

203.6

0.760120 4

1.417720

62

159.6

33

0.86020 20

1.44420

70

227–230

93

122, 95

0.90420

1.519720

267–275

110

2, 719

0.936620

1.441520

1.0

344–345

177

0.950

1.410320

23

560.5mm

37

231.2

93

4, 157

218.25

i aq, MeOH; s acet, bz, EtOH, EtAc, eth 0.004 aq

217–219

12, 400

0.938320 4

Dibutyl butanedioate, d130

1.492020

71

i aq; misc alc, eth

Dibutyl Cellosolve, d106

1.187

1.188

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d114 d115 d116 d117 d118

Name

Beilstein reference

(CH3)3CSSC(CH3)3

178.36

C4H9OC4H9

130.22

N,N-Dibutylformamide 3,5-Di-tert-butyl-4-hydroxybenzoic acid Dibutyl maleate

HC( ¨ O)N(C4H9)2

157.26

[(CH3)3C]2C6H2(OH)COOH C4H9OOCCH ¨ CHCOOC4H9 CH2COOC(CH3)3 ı COOC(CH3)3 [(CH3)3C]2C6H2 (CH3)OH

250.34

220.36

63, 2073

C4H9OOC ˆ COOC4H9

202.25

2, 540

(CH3)3CO ˆ OC(CH3)3

146.23

Di-tert-butyl malonate

d120

2,6-Di-tert-butyl-4methylphenol Dibutyl oxalate

d122

Formula weight

Di-tert-butyl disulfide Dibutyl ether

d119

d121

Formula

1, 369

Density

Refractive index

0.935

1.4920

0.768920 4

1.399220

0.864

1.442920

25

12015mm

100

135

1.418420

6.0

9310mm

0.89475 4

1.485975

70

265

0.98620 20

1.423220

30.0

239–240

0.79420

1.389020

40

110

56.5

[CH3CH2CH(CH3)]2C6H3OH [(CH3)3C]2C6H3OH

206.33

[(CH3)3C]2C6H3OH

206.33

d127

(C4H9O)2P(O)H

194.21

1, 187

0.99520 4

1.423120

d128

Dibutyl o-phthalate

C6H4[COOC4H9]2

278.35

92, 586

1.046520 4

1.492620

d126

142.4

d 280

216.27

206.33

93

80

206.33

d125

Flash point

229–33

1.445420

0.995020

228.28

[(CH3)3C]2C6H3OH

d124

97.9

Boiling point

Solubility in 100 parts solvent

0.03 aq; misc alc, eth

206–209

Di-tert-butyl peroxide 2,4-Di-tert-butylphenol 2,6-Di-sec-butylphenol 2,6-Di-tert-butylphenol 3,5-Di-tert-butylphenol Dibutyl phosphonate

d123

Melting point

0.918

1.510020

63, 2061

0.05 aq

i aq; s alc, bz, acet 108

misc alc, ketones, PE misc acet, octane

263.5

115

s hot alc; i alk

42

255–260

127

35–83

253

118

s hot alc; i alk

11811mm

121

340

171

sl s (hyd) aq; misc alc, acet, eth 0.01 aq; v s alc, bz, acet, eth

87–89

35

d129 d130 d131

N,N-Dibutyl-1,3propanediamine Dibutyl succinate Dibutyl sulfate

d132 d133

Dibutyl sulfide Di-tert-butyl sulfide d134 Dibutyl sulfite d135 Dibutyl sulfone d136 N,N-Dibutylthiourea d136a Dibutyltin dichloride d137 Dibutyltin oxide d138 Dichloroacetic acid d139 1,1-Dichloroacetone d140 d141 d142 d143 d144

2,4-Dichloroacetophenone Dichloroacetyl chloride 2,3-Dichloroaniline 2,4-Dichloroaniline 2,5-Dichloroaniline

0.827

1.446320

22, 551

0.976820 4 1.05925 4

1.429920 1.421320

29.0

146.30 146.30

1, 370

0.83916 0 0.815

1.453020 1.450620

75.0

(C4H9O)2S(O) (C4H9)2SO2 C4H9NHC( ¨ S)NHC4H9

194.29 178.29 188.34

12, 397 1, 371

0.994422 4

1.431020

(C4H9)2SnCl2

303.83

(C4H9)2SnO Cl2CHCOOH

248.92 128.94

41, 588 2, 202

1.56320 4

CH3C(O)CHCl2

126.97

1, 654

1.30518 15

Cl2C6H3COCH3

189.04

72, 219

C4H9NHCH2CH2CH2NHC4H9 [C4H9OOCCH2 ˆ ]2 C4H9OSO2OC4H9

186.34 230.30 210.29

C4H9SC4H9 (CH3)3CSC(CH3)3

1.464220

147.39

2, 204

Cl2C6H3NH2 Cl2C6H3NH2 Cl2C6H3NH2

162.02 162.02 162.02

12, 621 12, 621 12, 625

1.56720

274.5 130– 13211mm 188.9 76 151 48

Dibutyl phosphite, d127 Dibutyl sebacate, d110 Dichloroacetaldehyde diethyl acetal, d169

i aq; v s alc, eth

39–41

13510mm

112

300 9–11

193–194

112

misc aq, alc, eth

14515mm

112

sl s aq; s alc; misc eth i aq

107–108

66

d aq, alc; misc eth

252 245 251

112

s alc; v s eth sl s aq; s alc, eth s alc, bz, eth

33–34

1.460320 1.596920

i aq; s alc, eth

143

150 1.563520

Cl2CHCOCl

103

10815mm 295

46 63.65

1.531516 4

Di-tert-butylcresol, d120 2,5-Di-tert-butylhydroquinone, d112 Dibutyl ketone, n100

205

23–24 59.62 49–51

i aq; s alc, eth i aq; s alc; sl s eth

Dichloroanisoles, d191, d192

1.189

1.190

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d145 d146 d147 d148 d149 d150 d151 d152 d153 d154 d155 d156 d157 d158 d159 d160 d161 d162

Name 2,6-Dichloroaniline 3,4-Dichloroaniline 3,5-Dichloroaniline 1,5-Dichloroanthraquinone 1,8-Dichloroanthraquinone 2,4-Dichlorobenzaldehyde 2,4-Dichlorobenzamide 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene 2,5-Dichlorobenzenesulfonyl chloride 2,4-Dichlorobenzoic acid 2,5-Dichlorobenzoic acid 3,4-Dichlorobenzoic acid 4,4-Dichlorobenzophenone 2,4-Dichlorobenzoyl chloride 3,4-Dichlorobenzoyl chloride 1,2-Dichlorobutane

Formula weight

Beilstein reference

162.02 162.02 162.02 277.11

12, 626 12, 626 12, 626 7, 787

38.41 70–72 272 51–53 259741mm 245–247

s alc, eth; sl s bz i aq; s alc, eth sl s alc, bz, acet

277.11

7, 788

202–203

sl s alc

Cl2C6H3CHO

175.01

7, 236

69–73

Cl2C6H3CONH2

190.03

93, 1376

191–194

C6H4Cl2 C6H4Cl2 C6H4Cl2 Cl2C6H3SO2Cl

147.01 147.01 147.01 245.51

5, 201 5, 202 5, 203 111, 15

Cl2C6H3COOH

191.01

9, 342

157–160

Cl2C6H3COOH

191.01

9, 342

151–154 301

Cl2C6H3COOH

191.01

9, 343

207–209

(ClC6H4)2CO

251.11

7, 420

144–146 353

Cl2C6H3COCl

209.46

9, 342

Cl2D6H3COCl

209.46

9, 344

CH3CH2CH(Cl)CH2Cl

127.01

11, 38

Formula Cl2C6H3NH2 Cl2C6H3NH2 Cl2C6H3NH2

Density

1.305920 4 1.288420 4 1.241760

1.494

1.11820 4

Refractive index

1.5515 1.5459 1.5285

1.529720

1.447415

Melting point

17.0 24.8 53 36–37

Boiling point

Flash point

233

180.4 173.1 174.1

Solubility in 100 parts solvent

i aq; s alc

65 63 65

misc alc, bz, eth 0.01 aq; s alc, eth s alc, bz, chl, eth d hot aq, hot alc

16–18

15034mm

137

s hot aq, alc, bz, chl sl s aq; s alc, eth s hot aq, eth; v s alc s hot alc; v s chl, eth d aq, alc

30–33

242

142

d aq, alc

124

i aq; s chl, eth

d163 d164 d165 d166 d167 d168 d169 d170

d171 d172

1,4-Dichlorobutane meso-2,3-Dichlorobutane cis-1,4-Dichloro2-butene trans-1,4-Dichloro2-butene 3,4-Dichloro-1butene 1,4-Dichloro-2butyne 1,1-Dichloro-2,2-diethoxyethane Dichlorodifluoromethane

ClCH2CH2CH2CH2Cl CH3CH(Cl)CH(Cl)CH3

127.01 127.01

1, 119 1, 119

1.159820 4 1.102525 4

1.456620 1.438625

38 80

155 115.9

40 18

i aq; s chl i aq; s chl

ClCH2CH ¨ CHCH2Cl

125.00

13, 743

1.18825 4

1.488725

48

152

49

i aq; s org solv

ClCH2CH ¨ CHCH2Cl

125.00

13, 743

1.18325 4

1.486125

1–3

74–7640mm 56

i aq; s org solv

ClCH2CH(Cl)CH ¨ CH2

125.00

1.150

1.465820

61

123

28

ClCH2C ˜ CCH2Cl

122.98

13, 927

1.25820 4

1.504820

165–168

160

Cl2CHCH(OC2H5)2

187.07

1, 614

1.138

1.436020

183–184

60

Cl2CF2

120.92

1, 61

1.48630

4,6-Dichloro-1,3-dihydroxybenzene 2,5-Dichloro-3,6-dihydroxy-p-benzoquinone

Cl2C6H2(OH)2

179.00

61, 403

104–106 254

208.98

8, 379

283–284

2,6-Dichlorobenzyl chloride, t249 2,2-Dichlorodiethyl ether, b158

5,5-Dichloro-2,2-dihydroxydiphenylmethane, m233

158

29.8

0.02 aq; 9 bz; 5.5 chl; 6 diox; s alc, eth sl s aq, bz; s eth

1,1-Dichlorodimethyl ether, d197 Dichlorohydrin, d220

1.191

1.192

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d173

Name

Formula

Formula weight

Beilstein reference

197.02

242, 158

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

d176 d177

1,3-Dichloro-3,5-dimethylhydantoin Dichlorodimethylsilane Dichlorodiphenylsilane 1,1-Dichloroethane 1,2-Dichloroethane

d178

1,1-Dichloroethylene

H2C ¨ CCl2

96.94

1, 186

1.212920 4

1.424720

122.6

31.6

15

d179

cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene 2,2-Dichloroethyl ether 1,2-Dichloroethyltrichlorosilane Dichlorofluoromethane

ClCH ¨ CHCl

96.94

1, 188

1.281820 4

1.449020

80.1

60.7

6

0.51 aq; misc alc 0.8 aq; misc alc, chl, eth 0.02 aq; s alc, bz, chl, eth 0.7 aq; s alc, eth

ClCH ¨ CHCl

96.94

1, 188

1.254620 4

1.446220

49.8

47.7

6

0.6 aq; s alc, eth

ClCH2CH2OCH2CH2Cl

143.01

12, 335

1.222020 20

1.45720

178.5

55

1.1 aq; s alc, bz, eth

ClCH2CH(Cl)SiCl3

232.4

1.51625 4

1.44925

FCHCl2

102.92

82– 8426mm 8.9

C7H15Si(CH3)Cl2

225.2

F6C4Cl2

233.0

[ClC(CH3)2O]2Si3(CH3)2 Cl(CH2)6Cl

277.4

d174 d175

d180 d181 d182 d183

d184 d185 d186 d187

Dichloroheptylmethylsilane 1,2-Dichlorohexafluorocyclobutane 1,5-Dichlorohexamethyltrisiloxane 1,6-Dichlorohexane

134–136 1.06420 4

1.403820

16, 910

1.22220 4

1.58220

98.96 98.96

1, 83 1, 84

1.175720 4 1.253120 4

1.416420 1.444820

(CH3)2SiCl2

129.06

(C6H5)2SiCl2

253.20

CH3CHCl2 ClCH2CH2Cl

155.07

1, 61

1, 144

70

16

308–309

157

d aq, alc

97.0 35.7

57.3 83.5

5 15

135

1.34530 0.978020 4

16

1.439625

207–208

1.334225

59–60

1.01820 4

1.4071

184

1.068

1.456820

8715mm

69 HOAc; 108 diox; s alc, eth; i aq

73

s chl

d188

d189 d190 d191 d192 d193 d194 d195

d196 d197

1.449020

1.325520 4

1.424620

F(I)C(Cl)C(Cl)F2

2,3-Dichloro-1methoxybenzene 3,5-Dichloro-1methoxybenzene 2,4-Dichloro-6-methoxy-1,3,5-triazine (Dichloromethyl)dimethylchlorosilane 2,2-Dichloro-1methylcyclopropanecarboxylic acid N-(Dichloromethylene)aniline Dichloromethyl ether

Cl2C6H3OCH3

177.03

61, 102

31–33

Cl2C6H3OCH3

177.03

6, 190

40–42

Dichloroisopropyl alcohol, d220

278.9

2.20020

1,2-Dichloro-2-iodo1,1,2-trifluoroethane Dichloromaleic anhydride Dichloromethane

166.95 CH2Cl2

84.93

17, 434 1, 60

179.99 Cl2CHSi(Cl)(CH3)2

177.5

Cl2(C3H2)(CH3)COOH

169.01

C6H5N ¨ CCl2

174.03

Cl2CHOCH3

114.96

100–101

1.23720 4

12, 447

1.46120

96.7

40.5

86–88

13249mm

49

149

60–65

858mm

none

1.265

1.571020

10630mm

79

1.271

1.430020

85

42

4,4-Dichloro--methylbenzhydrol, b164

1.3 aq; misc alc, eth

1.193

1.194

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d198 d199 d200 d201 d202 d203 d204 d205 d206 d207 d208 d209 d210 d211 d212 d213 d214

Name Dichloro(methyl)phenylsilane Dichloro(methyl)silane Dichloro(methyl)vinylsilane 2,3-Dichloro-1,4naphthoquinone 2,6-Dichloro-4nitroaniline 2,3-Dichloronitrobenzene 2,4-Dichloronitrobenzene 3,4-Dichloronitrobenzene 2,3-Dichlorooctafluorobutane 1,7-Dichlorooctamethyltetrasiloxane 2,3-Dichloro-4-oxo2-butenoic acid 1,5-Dichloropentane 2,3-Dichlorophenol 2,4-Dichlorophenol 2,5-Dichlorophenol 2,6-Dichlorophenol 2,4-Dichlorophenoxyacetic acid

Formula

Formula weight

C6H5Si(CH3)Cl2

191.13

HSi(CH3)Cl2

115.04

H2C ¨ CHSi(CH3)Cl2

141.07

Beilstein reference

41, 581

Density

Refractive index

1.176

1.519020 93

1.105 1.08720 4

Melting point

1.430020

Boiling point

Flash point

205

82

41

32

92–93

4

Solubility in 100 parts solvent

227.05

7, 729

190–192

sl s alc, bz, eth

Cl2C6H2(NO2)NH2

207.02

12, 735

190–192

Cl2C6H3NO2

192.00

5, 245

1.72114

61–62

257–258

s PE

Cl2C6H3NO2

192.00

5, 245

1.43980

29–32

258

s hot alc; misc eth

Cl2C6H3NO2

192.00

5, 246

1.45675 4

41–42

255–256

CF3CF(Cl)CF(Cl)CF3

271.0

1.680120

1.310020

68

63

[Cl(CH3)2SiOSi(CH3)2 ˆ ]2O ClC(CHO) ¨ C(Cl)COOH

351.6

1.01120 4

1.40320

168.96

3, 727

Cl(CH2)5Cl Cl2C6H3OH Cl2C6H3OH Cl2C6H3OH Cl2C6H3OH Cl2C6H3OCH2COOH

141.04 163.00 163.00 163.00 163.00 221.04

1, 131 61, 102 6, 189 6, 189 6, 190

222 125–128

1.105815 4

1.455320

123

72 58.60 42–43 56–58 65–68 138

100 6310mm 206 210 211 218–220 1600.4mm

26 113

sl s aq; s alc, hot bz i aq; s alc, eth s alc, eth v s alc, bz, chl, eth v s alc, bz, eth v s alc, eth s alc, bz, chl, eth

d215 d216 d217 d218 d219 d220 d221 d222 d223 d224 d225 d226 d227

2,5-Dichloro-pphenylenediamine Dichlorophenylphosphine 4,5-Dichloro-ophthalic acid 1,2-Dichloropropane 1,3-Dichlopropane 1,3-Dichloro-2propanol 1,3-Dichloropropene 2,3-Dichloro-1propene 3,6-Dichloropyridazine 2,6-Dichloropyridine 4,7-Dichloroquinoline Dichlorosilane 1,2-Dichloro1,1,2,2-tetrafluoroethane

1,1-Dichloro-2-propanone, d139

Cl2C6H2(NH2)2

177.03

13, 118

165 d

C6H5PCl2

178.99

16, 763

Cl2C6H2(COOH)2

235.02

91, 366

CH3CH(Cl)CH2Cl

112.99

1, 105

1.155820

1.439020

100.4

96.4

4

ClCH2CH2CH2Cl ClCH2CH(OH)CH2Cl

112.99 128.99

1, 105 1, 364

1.87820 4 1.350617 4

1.448720 1.483520

99.5 4

120.5 174.3

32 74

ClCH2CH ¨ CHCl ClCH2C(Cl) ¨ CH2

110.97 110.97

1, 199 1, 199

1.21720 4 1.20425 25

1.47020 1.461120

112 94

10

1.319

1.598020

H2SiCl2 ClCF2CF2Cl

147.99 198.05 101.0 170.93

222

112

193–195

148.98 Cl2(C5H3N)

51

s aq; v s eth 0.26 aq; misc alc, bz, chl, eth v s alc, eth 9.1 aq; misc alc, eth i aq; s chl, eth misc alc; s eth

66–69 20, 231

1.47020 4

4,6-Dichlororesorcinol, d171

1.29020

86–88 84–86

14810mm

122 94

8.3 3.6

s alc, eth

,o-Dichlorotoluene, c59

1.195

1.196

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d228 d229 d230 d231 d232 d233

Name 2,5-Dichlorothiophene 2,4-Dichlorotoluene 2,6-Dichlorotoluene 3,4-Dichlorotoluene 2,2-Dichloro-1,1,1trifluoroethane ,-Dichloro-pxylene

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Cl2(C4H2S)

153.03

17, 33

1.442

1.562120

40.5

162

Cl2C6H3CH3 Cl2C6H3CH3 Cl2C6H3CH3 CF3CHCl2

161.03 161.03 161.03 152.9

5, 295 5, 296 5, 296

1.246020 20 1.254 1.25125 25

1.545420 1.550720 1.547220

13

200.5 196–203 201740mm 28

C6H4(CH2Cl)2

175.06

5, 384

100

254

71

222

Formula

14

Boiling point

Flash point

i aq; misc alc, eth 79 82 85

2,5-Dichloro-pxylene

Cl2C6H2(CH3)2

175.06

5, 384

d235 d236

Dicyanodiamide 1,2-Dicyanobenzene

H2NC( ¨ NH)NHCN C6H4(CN)2

84.08 128.13

32, 75 9, 815

d237 d238 d239 d240

C6H4(CN)2 NC(CH2)4CN NC(CH2)6CN CH3CH[CH(CN)CONH2]2 C6H11C6H11

128.13 108.14 136.20 194.19

9, 836 2, 653 2, 694 22, 704

0.951 0.954

1.438020 1.443620

158–160 1–3 295 3.5 18515mm 159–160

112 112

d241

1,3-Dicyanobenzene 1,4-Dicyanobutane 1,6-Dicyanohexane 2,4-Dicyano-3methylglutaramide Dicyclohexyl

166.31

5, 108

0.864

1.478220

3–4

227

101

d242

Dicyclohexylamine

(C6H11)2NH

181.32

12, 6

0.910

1.484220

0.1

255.8

96

d243

N, N-Dicyclohexylcarbodiimide Dicyclopentadiene

C6H11N ¨ C ¨ NC6H11

206.33

34–35

122– 1246mm 170

26

d244

132.21

5, 495

0.93025 4

208–211 139–141

1.505025

1

i aq i aq; s chl i aq

22.5 acet; 20 bz; 4.5 CCl4; 11 eth; 18 EtAc 27 acet; 44 bz; 39 eth 32 EtAc; 5 MeOH 2.3 aq; 1.3 alc; i bz v s bz, alc; s hot eth s alc, bz, chl, eth

d234

1.40025 4

Solubility in 100 parts solvent

7 MeOH; misc bz, acet, eth misc alc, bz, chl, eth

s alc, eth

d245

Diethanolamine

HOCH2CH2NHCH2CH2OH

105.14

4, 283

1.08830 4

1.474730

d246

2,2-Diethoxyacetophenone 4,4-Diethoxybutylamine 2,2-Diethoxy-N,Ndimethylethylamine Diethoxydimethylsilane Diethoxydiphenylsilane 1,1-Diethoxyethane 1,2-Diethoxyethane 2,2-Diethoxyethanol 2,2-Diethoxyethylamine Diethoxymethylsilane Diethoxymethylvinylsilane 1,1-Diethoxypropane 3,3-Diethoxy-1propene

C6H5C( ¨ O)CH(OC2H5)2 H2N(CH2)3CH(OC2H5)2 (C2H5O)2CHCH2N(CH3)2 (C2H5O)2Si(CH3)2

208.26

71, 361

1.034

1.499520

161.25

4, 319

0.933

1.427520

131– 110 13410mm 196 62

161.25

4, 308

0.883

1.412920

170

45

148.28

0.84020 4

1.381120

114

11

(C2H5O)2Si(C6H5)2

272.42

1.032920 4

1.526920

CH3CH(OC2H5)2 C2H5OCH2CH2OC2H5 (C2H5O)2CHCH2OH (C2H5O)2CHCH2NH2

118.18 118.18 134.18 133.19

0.825420 4 0.842 24 0.8884 0.916

1.382520 1.392220 1.416020 1.4170

(C2H5O)2SiH(CH3) (C2H5O)2Si(CH3)CH ¨ CH2 CH3CH2CH(OC2H5)2 (C2H5O)2CHCH ¨ CH2

134.3 160.3

0.82925 4 0.85820 4

1.37225 1.40020

94–95 133–134

0.823220 4 0.854

1.388420 1.400020

122.8 89–90

d247 d248 d249 d250 d251 d252 d253 d254 d255 d256 d257 d258

,p-Dichlorotoluene, c60

132.20 130.19

1, 603 1, 468 1, 818 4, 308

1, 630 1, 727

1,2-Dicyanoethane, b380

28.0

87

268.0

137

96 aq; 4 bz; 0.8 eth; misc MeOH, acet

1302mm 2.8 74

102.7 121.4 167 162–163

21 27 67 45

5 aq; misc alc, eth 21 aq s alc, eth

12 4

v s alc, eth

1.197

1.198

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d259 d260 d261 d262 d263 d264 d265 d266 d267 d268 d269 d270 d271

d272 d273

Name 2,2-Diethoxytriethylamine N,N-Diethylacetamide Diethyl acetamidomalonate Diethyl 1,3-acetonedicarboxylate Diethyl acetylenedicarboxylate Diethyl 2-acetylglutarate Diethyl acetylsuccinate Diethyl allylmalonate Diethylamine Diethylamine HCl 4-(Diethylamino)benzaldehyde 2-Diethylaminoethanol 2-(Diethylamino)ethyl-4-aminobenzoate 2-Diethylaminoethyl chloride HCl 3-(Diethylamino)phenol

Formula weight

Beilstein reference

Density

Refractive index

189.30

4, 309

0.850

1.418920

194–195

65

115.18

4, 110

0.925

1.440120

182–186

70

C2H5OOCCH(NHCOCH3)COOC2H5 C2H5OOCCH2COCH2COOC2H5 C2H5OOCC ¨ CCOOC2H5

217.22

42, 891

202.21

3, 791

1.113

1.438520

250

86

170.16

2, 803

1.063

1.442620

10711mm

94

C2H5OOCCH2CH2CH(COCH3)COOC2H5 C2H5OOCCH2CH(COCH3)COOC2H5 C2H5OOCCH(CH2CH ¨ CH2)COOC2H5 (C2H5)2NH (C2H5)2NH  HCl (C2H5)2NC6H4CHO

230.26

1.071

1.438620

15411mm

112

180– 112 18350mm 222–223 92

Formula (C2H5O)2CHCH2N(C2H5)2 CH3C( ¨ O)N(C2H5)2

Melting point

97–98

216.23

3, 801

1.081

1.434620

200.23

2, 776

1.015

1.430420

73.14 109.60 177.25

4, 95 4, 95 142, 25

0.707420 4 1.04821 4

1.386420

(C2H5)2NCH2CH2OH

117.19

4, 282

0.880025

H2NC6H4COOCH2CH2N(C2H5)2

236.30

14, 424

61

ClCH2CH2N(C2H5)2  HCl

172.10

42, 618

208–210

(C2H5)2NC6H4OH

165.24

13, 408

65–69

1.438925

50.0

Boiling point

Flash point

Solubility in 100 parts solvent

18520mm

28

misc aq, alc s aq, alc, chl; i eth

39–41

55.5 320–330 1747mm

70

163

48

s aq, alc, bz, eth 0.5 aq; s alc, bz, eth

17015mm

s aq, alc, eth

d274 d275 d276 d277 d278 d279 d280

d281 d282 d283 d284 d285 d286

3-Diethylamino-1,2propanediol 1-Diethylamino-2propanol 4-(Diethylamino)salicylaldehyde N, N-Diethylaniline 2,6-Diethylaniline Diethyl azodicarboxylate 5,5-Diethylbarbituric acid Diethyl benzalmalonate 1,2-Diethylbenzene 1,3-Diethylbenzene 1,4-Diethylbenzene Diethyl benzylmalonate Diethyl bromomalonate

Diethyl acetal, d251 Diethylacetic acid, e89

147.22

4, 302

0.97320 20

1.460220

233–235

131.22

42, 737

0.889

1.425520

13.5

193.25

14, 234

149.24 149.24 174.16

12, 164 3, 123

0.930225 4 0.906 1.106

184.19

242, 279

1.220

C6H5CH ¨ C(COOC2H5)2

248.28

9, 892

1.107

1.536520

C6H4(C2H5)2 C6H4(C2H5)2 C6H4(C2H5)2 C6H5CH2CH(COOC2H5)2 BrCH(COOC2H5)2

134.22 134.22 134.22 250.29

5, 426 5, 426 5, 426 9, 869

0.880020 0.864020 4 0.862020 4 1.064

1.502220 1.495020 1.494020 1.486820

239.07

2, 594

1.402225 4

1.455020

(C2H5)2NCH2CH(OH)CH2OH (C2H5)2NCH2CH(OH)CH3 (C2H5)2NC6H3(OH)CHO C6H5N(C2H5)2 (C2H5)2C6H3NH2 C2H5OOCN ¨ NCOOC2H5

107

s aq, alc, chl, eth

55–5913mm 33

s alc

216.3 243 10613mm

1 aq; sl s alc, eth

62–64

Diethyl 2-acetylpentanedioate, d264 Diethylaminoacetaldehyde diethyl acetal, d259

1.539425 1.545220 1.428020

34.4 3

97 123 26

188–192

0.7 aq; 7 alc; 1.3 chl; 3.2 eth; s acet, HOAc 21530mm

112

31.3 83.9 42.85

183.4 181.1 183.8 16210mm

49 50 56 112

54

233–235 d

s alc, eth s alc, eth s alc, eth

i aq; misc alc, eth

3-Diethylaminopropylamine, d330 Diethyl (Z)-2-butenedioate, d316

1.199

1.200

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d287 d288 d289

Name Diethyl butylmalonate Diethylcarbamoyl chloride Diethyl carbonate

d290

Diethyl chloromalonate d291 Diethyl chlorophosphate d292 Diethyl chlorothiophosphate d293 Diethylcyanamide d293a Diethyl cyanomethylphosphonate d294 N, N-Diethylcyclohexylamine d294a Diethyl disulfide d295

d296 d297 d298

Diethyldithiocarbamic acid, Na salt Diethyl dithiophosphate N,N-Diethyldodecanamide Diethylenetriamine

Formula weight

Beilstein reference

Density

Refractive index

C4H9CH(COOC2H5)2

216.28

21, 282

0.983

1.4220

235–240

93

v s alc, eth

(C2H5)2NCOCl

135.59

4, 120

1.451520

187–190

75

d hot aq, hot alc

(C2H5O)2C ¨ O

118.13

3, 5

0.976420 4

1.384320

126.8

25

ClCH(COOC2H5)2

194.61

22, 537

1.204020 4

1.431020

222–223

69 aq; misc alc, bz, eth, esters misc alc, chl, eth

(C2H5O)2P(O)Cl

172.55

1, 332

1.194

1.416520

602mm

(C2H5O)2P(S)Cl

188.61

1.200

1.471520

453mm

(C2H5)2NCN (C2H5O)2P(O)CH2CN

98.15 177.14

4, 121

0.846 1.095

1.422920 1.431220

186–188 1010.4mm

69 112

C6H11N(C2H5)2

155.29

12, 6

0.850

1.456220

194–195

57

C2H5SSC2H5

122.25

1, 347

0.99820 4

1.506320

(C2H5)2NC( ¨ S)SNa  3H2O

225.31

42, 613

(C2H5O)2P(S)SH

186.23

1, 333

CH3(CH2)10C(O)N(C2H5)2 (H2NCH2CH2)2NH

255.45

Formula

103.17

4, 255

Melting point

43.0

101.5

Boiling point

Flash point

154.0

Solubility in 100 parts solvent

sl s aq; misc alc, eth

95–99

1.111

1.512020

601mm

0.847

1.454520

1662mm

112

0.954220 20

1.482620

207.1

101

35

misc aq, alc, bz, eth

d299 d300 d301 d302 d303 d304 d305 d306 d307 d308 d309 d310

Diethylenetriaminepentaacetic acid Diethyl ether

[(HOOCCH2)2NCH2CH2]2NCH2COOH C2H5OC2H5

393.35 74.12

1, 314

0.713420 4

1.352720

Diethyl ethoxymethylenemalonate N,N-Diethylethylenediamine Diethyl ethylmalonate N,N-Diethylformamide Diethyl fumarate

(C2H5OOC)2C ¨ CHOC2H5 (C2H5)2NCH2CH2NH2

216.23

3, 469

1.070

116.21

4,251

C2H5CH(COOC2H5)2

188.2

(C2H5)2NCHO C2H5OOCCH ¨ CHCOOC2H5 (C2H5OOC)2C4H2O

Diethyl 3,4-furandicarboxylate Diethyl glutarate 2,4-Diethyl-2,6heptadienal Diethyl heptanedioate 2,4-Diethyl-1heptanol

C2H5OOCCH2CH2CH2COOC2H5 H2C ¨ CHCH2CH(C2H5)CH ¨ C(C2H5)CHO C2H5OOC(CH2)5COOC2H5 CH3CH2CH2CH(C2H5)CH2CH(C2H5)CH2OH

Diethyl carbitol, b176 Diethylene dioxide, d646 Diethylene glycol, b181 Diethylene glycol dibutyl ether, b151 Diethylene glycol diethyl ether, b176 Diethylene glycol dimethyl ether, b191

220 d 34.6

40

1.462020

279–281

155

0.827

1.436020

145–147

30

2,644

1.00420 20

1.415820

75–775mm

88

sl s aq; v s alc, eth

101.15

4, 109

0.908

1.434020

176–177

60

misc aq; v s alc, eth

172.18

2,742

1.05220 4

1.440620

218–219

91

1.140

1.471720

15513mm

82

1.022

1.424020

237

96

0.9 aq; v s alc; s eth

112

i aq; s alc, eth

212.20 188.22

2, 633

116.3

1–2

23.8

9112mm

166.27 216.28

6 aq; misc alc, bz, chl

2, 671

0.994520

172.31

Diethylene glycol monobutyl ether, b411 Diethylene glycol monoethyl ether, e35 Diethylene glycol monoethyl ether acetate, e36 Diethylene glycol monomethyl ether, m66 Diethyleneimide oxide, m448

1.428020

24

192100mm 10912mm

Diethyl ethoxycarbonylmethylphosphonate, t283 N,N-Diethylethanamine, t264 N,N-Diethylethanolamine, d270 Di-2-ethylhexyl adipate, d312 Di-2-ethylhexyl sebacate, d311

1.201

1.202

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

d311

Di-(2-ethylhexyl) decanedioate

d312

Di-(2-ethylhexyl) hexanedioate

d313

d316

Di-(2-ethylhexyl) ophthalate Diethyl hydrogen phosphonate N,N-Diethylhydroxylamine Diethyl maleate

d317

Diethyl malonate

d318 d319

Diethylmalonic acid N,N-Diethyl-3methylbenzamide Diethyl methylmalonate Diethyl 2-methyl-2oxosuccinate Diethyl methylsuccinate N,N-Diethyl-4nitrosoaniline Diethyl octanedioate

d314 d315

d320 d321 d322 d323 d324

Formula C4H9CH(C2H5)CH2OOC(CH2)8COOCH2CH(C2H5)C4H9 C4H9CH(C2H5)CH2OOC(CH2)4COOCH2CH(C2H5)C4H9 C6H4[COOCH2CH(C2H5)C4H9] (C2H5O)2P(O)H (C2H5)2NOH C2H5OOCCH ¨ CHCOOC2H5 C2H5OOCCH2COOC2H5 HOOCC(C2H5)2COOH CH3C6H4C( ¨ O)N(C2H5)2 C2H5OOCCH(CH3)COOC2H5 C2H5OOCCH(CH3)C( ¨ O)C( ¨ O)OC2H5 C2H5OOCCH2CH(CH3)COOC2H5 C6H4(NO)N(C2H5)2 C2H5OOC(CH2)6COOC2H5

Formula weight

Beilstein reference

Density

Refractive index

Melting point

426.68

0.91225 4

1.45125

2565mm

227

i aq; s alc, bz, acet

370.57

0.92525 25

1.447420

2145mm

193

s alc, eth, acet; iaq

390.56

0.98125 25

1.485320

384

207

50–512mm

90

50

Boiling point

Flash point

Solubility in 100 parts solvent

138.10

1, 330

1.07920 4

1.407620

89.14

4, 536

1.867

1.419520

25

125–130

45

172.18

2, 751

1.068720

1.440020

8.8

225.3

93

1.4 aq; s alc, eth

160.17

2, 573

1.0550

1.413620

48.9

199.3

100

160.17 191.27

2, 686 92, 325

127 0.99620 4

1.521220

d 170–180 1111mm

174.20

2, 629

1.01820 4

1.413020

198

76

2.7 aq; misc alc, eth v s aq, alc, eth s aq; v s alc, bz, eth sl s aq; v s alc, eth

202.21

3, 794

1.073

1.431320

13823mm

112

188.22

2, 639

1.012

1.419920

217–218

178.24

12, 684

230.30

2, 693

s aq (hyd), alc, eth

82–84 0.982220 4

1.432320

5.9

282

112

i aq; s alc, eth

1.078520 4

1.4102

162.14

1.1220 4

CH3CH(NH2)(CH2)3N(C2H5)2 C6H5CH(COOC2H5)2

158.29 236.27

C6H4(COOC2H5)2 (C2H5)2NCH2CH2CH2NH2 (C2H5)2C(CH2OH)2

222.24 130.24

C2H5OOCCH(C3H7)COOC2H5 HC ˜ CC(C2H5)2NH2

202.25

d325

Diethyl oxalate

C2H5OOCCOOC2H5

146.14

d326

Diethyl oxydiformate

[C2H5OC( ¨ O)]2O

d327

d335

N1,N1-Diethyl-1,4pentanediamine Diethyl phenylmalonate Diethyl o-phthalate N,N-Diethyl-1,3propanediamine 2,2-Diethyl-1,3propanediol Diethyl propylmalonate 1,1-Diethyl-2propynylamine N,N-Diethyl-3pyridinecarboxamide Diethyl succinate

d336 d337 d338

Diethyl sulfate Diethyl sulfide Diethyl sulfite

d328 d329 d330 d331 d332 d333 d334

Diethyl ketone, p42 N,N-Diethylnicotinamide, d334 O,O-Diethyl O-p-nitrophenyl phosphorothioate, p3 Diethyl 3-oxoglutarate, d262

2, 535

40.6

185.4

75

1.398020

9318mm

69

0.817

1.442920

200753mm

68

3.6aq (gradual d); misc alc, eth s alc, esters, ketones s aq, alc, eth

9, 854

1.095020 4

1.491320

16

17014mm

112

i aq; s alc

9, 798

1.23214 4 0.826

1.504914 1.441620

3

295 159

140 58

i aq; misc alc, eth

1.05220

1.457425

61.3

12510mm

0.987

1.418520

221–222

91

0.828

1.440920

7190mm

21

132.20 2, 657

111.19

25 aq; v s alc, eth

C5H4N ˆ C( ¨ O)N(C2H5)2

178.24

222, 34

1.06025 4

1.524020

24–26

296–300

112

C2H5OOCCH2CH2COOC2H5 (C2H5O)2SO2 (C2H5)2S (C2H5O)2S(O)

174.20

2, 609

1.04020 4

1.420020

21

217.7

110

i aq; misc alc, eth

154.18 90.19 138.19

1, 327 1, 344 1, 325

1.17225 4 0.836720 4 1.07725 4

1.400420 1.443020

25 103.9

209 d 92.1 157.7

78 9

misc alc, eth i aq; misc alc, eth s aq(d), alc

Diethyl 2-pentenedioate, d307 Diethyl phosphite, d314 Diethyl phosphorochloridate, d291 Diethyl phosphorochloridothionate, d292 Diethyl pimelate, d309

Diethyl propanedioate, d317 1,1-Diethylpropargylamine, d333 Diethyl pyrocarbonate, d326 Diethyl suberate, d324

1.203

1.204

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d339 d340 d341 d342 d343

d344 d345 d346 d347 d348 d349 d350 d351 d352 d353 d354

d355

Name ()-DiethylL-tartrate ()-DiethylD-tartrate Diethyl 3,3-thiopropionate N,N-Diethyl-mtoluamide N,N-Diethyl-1,1,1trimethylsilylamine Diethylzinc 1,4-Difluorobenzene 1,1-Difluoroethane 1,1-Difluorotetrachloroethane 1,2-Difluorotetrachloroethane Dihexylamine Dihexyl ether 9,10-Dihydroanthracene ()-Dihydrocarvone Dihydrocoumarin 10,11-Dihydro-5Hdibenzo-[a,d]cyclohepten-5-one 3,4-Dihydro-2ethoxy-2H-pyran

Formula weight

Beilstein reference

Density

Refractive index

Melting point

[ ˆ CH(OH)COOC2H5]2

206.19

3, 512

1.20420 4

1.445920

17

[ ˆ CH(OH)COOC2H5]2

206.19

31, 181

1.205

S(CH2CH2COOC2H5)2

234.32

CH3C6H4C( ¨ O)N(C2H5)2 (C2H5)2NSi(CH3)3

191.27 145.32

(C2H5)2Zn C6H4F2 CH3CHF2 Cl3CCClF2

123.49 114.09 66.05 203.83

FCl2CCCl2F (C6H13)2NH (C6H13)2O

Formula

92, 325

Flash point

280

93

1.446720

16219mm

93

1.095

1.465520

1212mm

0.996

1.521220

1111mm

0.767

1.408120

125–126

1.413

118 88.9 24.7 91

1.644725 4

1.41325

23.8

203.8

41, 384 13, 1656 5, 641

0.795 0.793620 4 0.880

1.432020 1.420420

192–195 226.2 108–110 312

95 77

73, 337 17, 315

0.92919 1.16918 1.156

1.471820 1.556320 1.633220

221–222 272 1480.3mm

81

0.957

1.439420

4216mm

24

1, 86

203.83

13, 365

185.36 186.34 180.25 152.24 148.16 208.26

5, 199

1.441520

25 32–34

Solubility in 100 parts solvent sl s aq; misc alc, eth

10

28 23.7 117 41

1.206520 1.170120 0.90921 1.649

128.17

Boiling point

2 none

0.32 aq sl s alc; v s eth i aq; s alc, eth s alc, eth i aq; s eth i aq; s alc, bz, eth

sl s alc, eth; s chl 112

d356 d537

2,3-Dihydrofuran Dihydrolinalool

d358

3,4-Dihydro-1(2H)6-methoxynaphthalenone 3,4-Dihydro-2methoxy-2H-pyran 2,3-Dihydro-2methylbenzofuran 5,6-Dihydro-4methyl-2H-pyran

d359 d360 d361

Diglycine, i10 Diglycol, b181 Diglycolic acid, o61 Diglyme, b191

(CH3)2C ¨ CHCH2CH2C(OH)(CH3)CH2CH3

70.09 156.27

173, 141

176.22

92, 889

0.927 0.92525

1.423920 1.43320

54–55

80

17111mm

1.442520

114.14

1 178

16

134.18

171, 23

1.061

1.530820

197–198

62

98.15

173, 160

0.912

1.449520

117–118

21

Dihydroanisoles, m61, m62 6,7-Dihydro-5H-cyclopenta[b]pyridine, c360 10,11-Dihydro-5H-dibenz[b,f]acepine, i12 2,5-Dihydro-2,5-dimethoxyfuran, d436

3,7-Dihydro-3,7-dimethyl-1H-pyridine-2,6dione, t138 2,3-Dihydroindene, i13 Dihydromyrcenol, m303

1.205

1.206

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d362 d363 d364

d365

d366 d367

d368 d369 d370

d371 d372 d373 d374 d375

Name 3,4-Dihydro-1(2H)naphthalenone Dihydropyran 5,6-Dihydro-2Hpyran-3-carbaldehyde 3,4-Dihydro-2Hpyran-2-carboxylic acid, Na salt Dihydroterpineol 5,6-Dihydro-2,4,4,6tetramethyl-4H1,3-oxazine 2,5-Dihydrothiophene-1,1-dioxide 1,2-Dihydro-2,2,4trimethylquinoline 2,4,-Dihydroxyacetophenone 1,2-Dihydroxyanthraquinone 1,4-Dihydroxyanthraquinone 1,8-Dihydroxyanthraquinone 2,6-Dihydroxyanthraquinone 2,4-Dihydroxybenzaldehyde

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

146.19

7, 370

1.099

1.568520

5–6

1166mm

112

0.92219 15 1.100

1.441020 1.498020

70

86 7812mm

15 77

84.12 112.13

150.11

0.90725 0.886

1.467020 1.441020

118.15

Solubility in 100 parts solvent

s aq, alc

88 4817mm 112

64–66

173.26

(HO)2C6H3CHO

Flash point

242–244

256.27 141.21

(HO)2C6H3C( ¨ O)CH3

Boiling point

0.934 1.180

1.589520

900.02mm 145–147

s aq, alc, bz, chl, eth

101

152.15

8, 266

s warm alc, pyr, HOAc; i bz, chl, eth s alc, bz, chl, HOAc s alc, alk, eth

240.21

8, 439

287–289 430

240.21

8, 450

196

240.21

8, 458

193–197 subl

240.21

8, 463

360 d

0.005 alc; 0.2 eth; s chl sl s aq, alc

138.12

8, 241

135–136 22622mm

v s aq, alc, chl, eth

d376

(HO)2C6H3CHO

138.12

8, 246

d377

3,4-Dihydroxybenzaldehyde 1,2-Dihydroxybenzene

C6H4(OH)2

110.11

6, 759

1.3444

104–106 245.5

137

d378

1,3-Dihydroxybenzene

C6H4(OH)2

110.11

62, 802

1.27215

109–110 276

171

d379

1,4-Dihydroxybenzene

C6H4(OH)2

110.11

6, 836

1.33215

170–171 285–287

4,5-Dihydro-2-(phenylmethyl)-1H-imidazole, b102 Dihydroresorcinol, c322

153

3,7-Dihydro-1,3,7-trimethyl-1H-purine2-6-dione, c1 1,3-Dihydroxyacetone, d397

5 aq; 79 hot alc; v s eth 43 aq; s alc, bz, chl, eth; v s pyr, alk 110 aq; 110 alc; v s eth, glyc; sl s chl 7 aq; v s alc, eth

2,2-Dihydroxy-2,2-biindan-1,2,3,3tetrone, h85

1.207

1.208

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d380 d381

d382

d383 d384 d385 d386 d387 d388 d389 d390 d391 d392

Name 1,3-Dihydroxybenzene monoacetate 2,5-Dihydroxy-pbenzenedisulfonic acid, K salt 2,5-Dihydroxybenzenesulfonic acid, K salt 2,4-Dihydroxybenzoic acid 2,5-Dihydroxybenzoic acid 3,5-Dihydroxybenzoic acid 2,4-Dihydroxybenzophenone 2,2-Dihydroxybiphenyl 4,6-Dihydroxy-2mercaptopyrimidine 1,2-Dihydroxy-4methylbenzene 1,3-Dihydroxy-2methylbenzene 2,4-Dihydroxy-6methylpyrimidine 1,5-Dihydroxynaphthalene

Formula weight

Beilstein reference

HOC6H4OOCCH3

152.15

6, 816

 (HO)2C6H2(SO 3 K )2

346.43

11, 300

300

v s aq

 (HO)2C6H3SO 3K

228.27

11, 300

251 d

v s aq

(HO)2C6H3COOH

154.12

10, 377

213

s hot aq, alc, eth

(HO)2C6H3COOH

154.12

10, 384

199–200

0.5 aq; s alc, eth

(HO)2C6H3COOH

154.12

10, 404

236 d

sl s aq; s alc, eth

(HO)2C6H3C( ¨ O)C6H5

214.22

8, 312

144–145

v s alc, eth, HOAc

HOC6H4C6H4OH

186.21

6, 989

110

144.15

24, 476

236

(HO)2C6H3CH3

124.14

6, 878

(HO)2C6H3CH3

124.14

6, 878

115–118 264

126.12

24, 342

318 d

160.17

6, 980

259 d

Formula

C10H6(OH)2

Density

Refractive index

Melting point

1.535020

1.12974 4

1.542574

Boiling point 283

67–69

Flash point

Solubility in 100 parts solvent

112

315

s alc, bz, eth; sl s aq

251

v s aq, alc, eth s aq, alc, bz, eth

sl s aq; s alc; v s eth

d393 d394 d395 d396

d397 d398 d399 d400 d401

1,7-Dihydroxynaphthalene 2,3-Dihydroxynaphthalene 2,7-Dihydroxynaphthalene 4,5-Dihydroxynaphthalene-2,7disulfonic acid 1,3-Dihydroxy-2propanone 2,3-Dihydroxypropionaldehyde 7-(2,3-Dihydroxypropyl)theophylline 3,6-Dihydroxypyridazine 2,3-Dihydroxypyridine

C10H6(OH)2

160.17

6, 981

177–180

v s alc, eth

C10H6(OH)2

160.17

6, 982

162–164

v s alc, eth

C10H6(OH)2

160.17

6, 985

187 d

sl s aq; v s alc, eth

(HO)2C10H4(SO3H)2

296.26

11, 307

HOCH2C( ¨ O)CH2OH

90.08

1, 846

HOCH2CHOCHO

90.08

1, 845

v s aq; i alc, eth

65–71 1.45518 18

254.25

(HO)2C5H3N

2,2-Dihydroxydiethylamine, d245 N,N-Di(hydroxyethyl)aminoacetic acid, b182 2,2-Dihydroxy-1,3-indandione, i16

145

112

158

33 aq; 2 alc; 1 chl sl s hot alc; s hot aq

112.09

24, 312

d 260

111.10

212, 107

245 d

2,2-Dihydroxymethyl-1-butanol, e156 1,8-Dihydroxynaphthalene-3,6-disulfonic acid, d396

1400.8mm

v s aq, alc, acet, eth 3 aq; i bz, PE

Dihydroxypropanes, p194, p195

1.209

1.210

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

d402 d403 d404

1,4-Diiodobenzene 1,2-Diiodoethane Diiodomethane

C6H4I2 ICH2CH2I CH2I2

329.91 281.86 267.84

5, 227 1, 99 1, 71

2.13210 3.32520 4

1.741120

131–133 285 81 200 5.6 181

d405 d406

1,3-Diiodopropane Diisobutylamine

ICH2CH2CH2I [(CH3)2CHCH2]2NH

295.88 129.25

1, 115 4, 166

2.575520 4 0.740

1.642320 1.408120

13 77

d407 d408

Diisobutyl ether Diisobutyl hexanedioate Diisobutylo-phthalate 1,6-Diisocyanatohexane Diisopropylamine 2-(Diisopropylamino)ethanol 2,6-Diisopropylaniline 1,3-Diisopropylbenzene 1,4-Diisopropylbenzene Diisopropylcyanamide Diisopropyl ether

[(CH3)2CHCH2]2O [(CH3)2CHCH2OOCCH2CH2 ˆ ]2 C6H4[COOCH2CH(CH3)2]2 OCN(CH2)6NCO

130.22 258.36

0.76115 0.95025 25

278.35

1.03825 25

168.20

42, 711

1.040

1.452520

[(CH3)2CH]2NH [(CH3)2CH]2NCH2CH2OH [(CH3)2CH]2C6H3NH2

101.19 145.25

4, 154 41, 430

0.716920 0.826

1.392420 1.441720

177.29

12, 168

0.940

C6H4[CH(CH3)2]2

162.28

5, 447

C6H4[CH(CH3)2]2

162.28

[(CH3)2CH]2NCN

d409 d410 d411 d412 d413 d414 d415 d416 d417 d418

N,N-Diisopropylethylamine

222 137–139

Flash point

29

122–124

Solubility in 100 parts solvent sl s alc; v s eth sl s aq; s alc, eth 0.12 aq; misc alc, bz, eth, PE i aq; s chl, eth s alc, acet, eth, EtAc i aq; misc alc, eth

160 174 255

140

96.3

83.5 187–192

6 57

1.533220

45

257

123

0.85620 4

1.498020

63

203

76

52, 339

0.85720 4

1.488920

203

76

126.20

43, 279

0.839

1.427020

9325mm

78

[(CH3)2CH]2O

102.17

1, 362

0.725820 4

1.368920

68.4

12

[(CH3)2CH]2NC2H5

129.25

0.742

1.413320

127

10

86.9

11 aq

misc alc, bz, eth, acet misc alc, bz, eth, acet

1.2 aq; misc alc, bz, chl, eth

112

[(CH3)2CH]2C6H3OH

178.28

61, 272

0.962

1.514020

[(CH3)2CHO]2P(O)H

166.16

1, 363

0.997

1.407020

72–7510mm 112

[ ˆ CH(OH)COOCH(CH3)2]2

234.25

3, 517

1.114

1.438720

15212mm

109

1.433020 1.452020

127

33 112

d431 d432

2,6-Diisopropylphenol Diisopropyl phosphite ()-Diisopropyl L-tartrate Diketene Dilauryl phosphite threo-1,4-Dimercapto2,3-butanediol 2,3-Dimercapto-1propanol 3,4-Dimethoxyacetophenone 2,4-Dimethoxyaniline 2,5-Dimethoxyaniline 3,4-Dimethoxyaniline 3,4-Dimethoxybenzaldehyde 1,2-Dimethoxybenzene 1,3-Dimethoxybenzene

d433

1,4-Dimethoxybenzene

d419 d420 d421 d422 d423 d424 d425 d426 d427 d428 d429 d430

Dihydroxytoluene, d390 3, 5-Diiodosalicylic acid, h111 2Diisobutyl adipate, d408

18

256

[CH3(CH2)11O]2P(O)H HSCH2CH(OH)CH(OH)CH2SH HSCH2CH(SH)CH2OH

84.07 418.64 154.25

1.073 0.946

124.22

1.238525 4

(CH3O)2C6H3COCH3

180.20

82, 298

49–51

286–288

sl s aq, alc, eth

(CH3O)2C6H3NH2 (CH3O)2C6H3NH2 (CH3O)2C6H3NH2 (CH3O)2C6H3CHO

153.18 153.18 153.18 166.18

13, 784 13, 788 13, 780 8, 255

34–37 80–82 88 42–43

270 sl d 17622mm 281

s alc, bz, eth s aq, alc s hot eth v s alc, eth

C6H4(OCH3)2 C6H4(OCH3)2

138.17 138.17

6, 771 6, 813

1.081925 1.055

22.5 55

206.3 85–877mm

C6H4(OCH3)2

138.17

6, 843

1.03668 4

55–60

213

42–43

Diisobutylene, t357 Diisobutyl ketone, d531 Diisopropyl ketone, d578

1.572025

1.523225 1.5240

v s aq, alc, chl, eth 12015mm

112

87 87

Diisopropylmethane, d572 Dimedone, d508 1, 1-Dimethoxytrimethylamine, d523

8 aq(d); s alc, eth

sl s aq; s alc, eth s alc, bz, eth; sl s aq s alc; v s bz, eth

1.211

1.212

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

d434 d435 d436 d437 d438 d439 d440 d441 d442 d443 d444 d445 d446 d447 d448 d449

Name

3,4-Dimethoxybenzoic acid 1,1-Dimethoxy-3butanone 2,5-Dimethoxy-2,5dihydrofuran Dimethoxydiphenylsilane 1,1-Dimethoxyethane 1,2-Dimethoxyethane (2,2-Dimethoxy)ethylamine Dimethoxymethane 1,1-Dimethoxy-2methylaminoethane Dimethoxymethylphenylsilane 1,2-Dimethoxy-4nitrobenzene 2,5-Dimethoxy-4nitrostilbene 2,6-Dimethoxyphenol (3,4-Dimethoxy)phenylacetic acid (3,4-Dimethoxy)phenylacetonitrile 2,2-Dimethoxy-2phenylacetophenone

Formula weight

Beilstein reference

(CH30)2C6H3COOH

182.18

101, 188

(CH3O)2CHCH2COCH3

132.16

0.993

1.415020

130.14

1.073

1.433920

160–162

(C6H5)2Si(OCH3)2

244.4

1.077120 4

1.544720

16115mm

CH3CH(OCH3)2 CH3OCH2CH2OCH3 H2NCH2CH(OCH3)2

90.12 90.12 105.14

1, 603 1, 467 42, 758

0.850220 0.862920 4 0.965

1.379620 1.417020

CH2(OCH3)2 CH3NHCH2CH(OCH3)2

76.10 119.16

1, 574 42, 759

0.860120 20 0.928

1.353420 1.411520

(CH3O)2Si(CH3)C6H5

182.3

0.99320 4

1.46920

(CH3O)2C6H3NO2

183.16

6, 789

(CH3O)2C6H3CH ¨ CHC6H4NO2 (CH3O)2C6H3OH (CH3O)2C6H3CH2COOH

285.30

62, 987

117–119

154.17 196.20

6, 1081 10, 409

(CH3O)2C6H3CH2CN

177.20

101, 198

C6H5C(O)C(OCH3)2C6H5

256.30

Formula

Density

Refractive index

Melting point

Boiling point

Flash point

180–181

1.1888133 4

Solubility in 100 parts solvent

0.047 aq; v s alc, eth 49 47

113 68

64.5 85.2 13595mm

1 53

104.8

42.3 140

17 29

s aq, alc, chl, eth misc aq, alc; s PE

32 aq

199–200 23017mm

v s alc, eth; s chl

53–56 96–98

261

s alc, alk; v s eth s aq; v s alc, eth

62–63

171– 17810mm

95–98

67–70

d450 d451 d452 d453 d454 d455 d456 d457 d458 d459

d460 d461

1,1-Dimethoxy-2phenylethane -(3,4-Dimethoxy)phenylethylamine 2,2-Dimethoxypropane 1,1-Dimethoxy-2propanone 3,3-Dimethoxy-1propene 1,2-Dimethoxy-4propenylbenzene 2,6-Dimethoxypyridine 2,5-Dimethoxytetrahydrofuran N,N-Dimethylacetamide Dimethyl 1,3acetonedicarboxylate Dimethyl acetylenedicarboxylate Dimethylamine

Dimethyl acetal, d438 Dimethylacetic acid, m390

C6H5CH2CH(OCH3)2

166.22

7, 293

1.004

1.495020

221

(CH3O)2C6H3CH2CH2NH2 (CH3)2C(OCH3)2

181.24

13, 800

1.074

1.546420

18815mm

104.15

1, 648

0.847

1.3780

83

4

CH3C(O)CH(OCH3)2

118.13

11, 395

0.976

1.397820

143–147

37

(CH3O)2CHCH ¨ CH2

102.13

11, 378

0.862

1.395420

89–90

CH3CH ¨ CHC6H3(OCH3)2 (CH3O)2C5H3N

178.23

6, 956

1.055

1.568020

262–264

112

139.15

1.053

1.502920

178–180

61

(CH3O)2C4H6O

132.16

1.020

1.418020

145–147

35

165.5

70 112

20

83

87.12

4, 59

0.936625

1.435625

[CH3OOCCH2]2C ¨ O

174.15

3, 790

1.185

1.443420

15025mm

CH3OOCC ˜ CCOOCH3

142.11

2, 803

1.156

1.447020

95–9819mm 86

45.09

4, 39

0.68004

CH3C(O)N(CH3)2

(CH3)2NH

2,3-Dimethylacrylic acids, m161, m162 3,3-Dimethylacrylic acid, m163

92.2

6.9

misc aq, alc, bz, eth

v s aq; s alc, eth

3,3-Dimethylallene, m148 Dimethylaminoacetaldehyde diethyl acetal, d249

1.213

1.214

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d462 d463

d464 d465 d466 d467 d468 d469 d470 d471 d472 d473 d474 d475

Name 4-Dimethylaminobenzaldehyde p-(Dimethylamino)benzenesulfonic acid, Na salt 4-Dimethylaminobenzoic acid 2-(Dimethylamino)ethanol 2-(Dimethylamino)ethyl benzoate 2-Dimethylaminoethyl chloride HCl 2-(Dimethylamino)ethyl methacrylate 4-Dimethylamino-3methyl-2-butanone 3-Dimethylaminophenol 3-(Dimethylamino)1,2-propanediol 1-Dimethylamino-2propanol 3-Dimethylamino-1propanol 3-(Dimethylamino)propionitrile 3-Dimethylaminopropyl chloride HCl

Formula weight

Beilstein reference

(CH3)2NC6H4CHO

149.19

14, 31

74

(CH3)2NC6H4SO3Na

223.23

143, 2023

300

(CH3)2NC6H4COOH

165.19

14, 426

241 d

(CH3)2NCH2CH2OH

89.14

4, 276

Formula

Density

Refractive index

Melting point

Boiling point

Flash point

17617mm

s alc, chl, eth, HOAc

s alc; sl s eth

0.887620 4

1.429420

135

1.014

1.507720

15520mm

40

C6H5COOCH2CH2N(CH3)2 (CH3)2NCH2CH2Cl · HCl

193.26 144.05

4, 133

H2C ¨ C(CH3)COOCH2CH2N(CH3)2 (CH3)2NCH2CH(CH3)COCH3 (CH3)2NC6H4OH

157.22

43, 649

0.933

1.439120

182–192

70

129.20

41, 452

0.841

1.425020

7335mm

38

137.18

13, 405

1.589526

119.16

4, 302

1.004

1.460920

216–217

105

0.837

1.419320

121–127

35

163–164

36

171750mm

62

82–84

103.17

(CH3)2NCH2CH2CH2OH

103.17

41, 433

0.872

1.436020

98.15

43, 1265

0.870

1.425820

(CH3)2NCH2CH2CH2Cl · HCl

158.07

4, 148

misc aq, alc, eth

205–208

(CH3)2NCH2CH(OH)CH2OH CH3CH(OH)CH2N(CH3)2

(CH3)2NCH2CH2CN

Solubility in 100 parts solvent

43 141–144

265–268

35

v s alc, bz, eth, acet s aq, alc, chl, eth

d476 d477 d478 d479 d480 d481 d482 d483 d484 d485 d486 d487 d488 d489 d490 d491

4-(Dimethylamino)pyridine N,N-Dimethylaniline 2,3-Dimethylaniline 2,4-Dimethylaniline 2,5-Dimethylaniline 2,6-Dimethylaniline 3,4-Dimethylaniline 3,5-Dimethylaniline Dimethylarsinic acid 3,4-Dimethylbenzoic acid 2,5-Dimethylbenzonitrile N,N-Dimethylbenzylamine 2,3-Dimethyl-1,3butadiene 2,2-Dimethylbutane 2,3-Dimethylbutane 2,3-Dimethyl-2-3butanediol

(CH3)2N(C5H4N)

122.17

222, 341

C6H5N(CH3)2

121.18

12, 141

0.955920 4

1.558420

2.5

194.2

62

v s alc, chl, eth

(CH3)2C6H3NH2

121.18

12, 1101

0.993120

1.568520

2.5

221–222

96

sl s aq; s alc, eth

(CH3)2C6H3NH2

121.18

12, 1111

0.98020 4

1.558620

218

90

s alc, bz, eth

(CH3)2C6H3NH2

121.18

12, 1135

0.979021 4

1.559220

11.5

218

93

sl s aq; s alc, eth

(CH3)2C6H3NH2

121.18

12, 1107

0.98420

1.560120

10–12

216

91

sl s aq; s alc, eth

(CH3)2C6H3NH2 (CH3)2C6H3NH2 (CH3)2As(O)OH

121.18 121.18 137.99

12, 1103 12, 1131

1.07618 0.97220 4

49–51 1.557820

226 10414mm

93

(CH3)2C6H3COOH

150.18

92, 353

(CH3)2C6H3CN

131.18

9, 535

0.957

1.528420

13–14

223730mm

92

C6H5CH2N(CH3)2

135.21

12, 1019

0.900

1.501120

75

183

54

82.15

13, 991

0.722225 4

1.436225

76.0

69.2

1

86.18 86.18 118.18

1, 150 1, 151 1, 487

0.649220 0.661620

1.368820 1.375020

99.9 128.5 41.1

49.7 58.0 174.4

28 28

H2C ¨ C(CH3)C(CH3) ¨ CH2 CH3CH2C(CH3)3 (CH3)2CHCH(CH3)2 (CH3)2C(OH)C(OH)(CH3)2

1.215

3-Dimethylaminopropylamine, d593 Dimethylanisoles, d547, d548 2,4-Dimethyl-3-azapentane, d411

108–110

v s aq, alc, bz, chl

195–196 165–167 subl

Dimethylbenzenes, x4, x5, x6 6,6-Dimethylbicyclo[3.1.1]hept-2-ene-2-ethanol, n105

sl s aq; s alc sl s aq; s alc v s alc; 200 aq; i eth s alc, bz

v s hot aq, alc, eth

Dimethyl (Z)-butenedioate, d544

1.216

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d492 d493 d494 d495 d496 d497 d498 d499 d500 d501

d502 d503 d504 d505

Formula weight

Beilstein reference

Density

Refractive index

Melting point

CH3CH2C(CH3)2CH2OH

102.18

13, 1675

0.828620 4

1.420820

15

(CH3)2CHCH(CH3)CH2OH (CH3)2CHC(CH3)2OH

102.18

13, 1677

0.830020 4

1.420520

102.18

1, 413

0.823620 4

1.417620

10.6

118.7

29

s aq; misc alc, eth

(CH3)3CCH2CH2OH

102.18

13, 1677

0.814720

1.412020

60

143

47

s alc, eth

(CH3)3CCH(OH)CH3

102.18

1, 412

0.818520 4

1.415120

5.3

120.4

28

s alc; misc eth

(CH3)3CCOCH3

100.16

1, 694

0.725025 25

1.393925

52.5

106.2

23

2.5 aq; s alc, eth

(CH3)2C ¨ C(CH3)2

84.16

1, 218

0.708120 4

1.412420

74.3

73.2

16

s alc, eth

(CH3)3CCH ¨ CH2

84.16

1, 217

0.653120 4

1.376220

115.2

41.3

28

(CH3)3CCH2COOH

116.16

2, 337

0.912420 4

1.410020

6–7

190

88

(CH3)2Cd

142.48

1.984617 4

1.5488

4.5

105.5

(CH3)2NCOCl

107.54

4, 73

1.168

1.454020

33

168

150 d aq; s PE explodes 68

(CH3O)2C ¨ O (CH3O)2P(S)Cl

90.08 160.56

3, 4 11, 143

1.06517 4 1.322

1.368220 1.481920

0.5

90–91 6716mm

18

4, 74

0.867

1.410020

161–163

58

Name 2,2-Dimethyl-1butanol 2,3-Dimethyl-1butanol 2,3-Dimethyl-2butanol 3,3-Dimethyl-1butanol 3,3-Dimethyl-2butanol 3,3-Dimethyl-2butanone 2,3-Dimethyl-2butene 3,3-Dimethyl-1butene 3,3-Dimethylbutyric acid Dimethylcadmium

Dimethylcarbamyl chloride Dimethyl carbonate Dimethyl chlorothiophosphate Dimethylcyanamide

Formula

(CH3)2NCN

70.09

Boiling point

Flash point

Solubility in 100 parts solvent

136.8

sl s aq; s alc, eth

149

s alc, eth

s alc, eth

i aq; misc alc, eth

d506 d507 d508 d509 d510 d511 d512 d513

d514

cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane 5,5-Dimethyl-1,3cyclohexanedione 2,3-Dimethylcyclohexanol 2,6-Dimethylcyclohexanone 2,3-Dimethylcyclohexylamine Dimethyl decanedioate 5,7-Dimethyl-3,5,9decatrien-2-one Dimethyl 2,5-dioxo1,4-cyclohexanedicarboxylate

Dimethyl 2-butynedioate, d460 Dimethyl Cellosolve, d439 Dimethylchlorosilane, c92

(CH3)2C6H10

112.22

5, 36

0.769220 4

1.433520

49.9

129.7

15

i aq; s alc, bz

(CH3)2C6H10

112.22

5, 36

0.777220 0

1.427320

88.2

123.4

15

i aq; s alc, eth

140.18

7, 559

(CH3)2C6H9OH

128.22 126.20

(CH3)2C6H9NH2

127.23

CH3OOC(CH2)8COOCH3

230.30

H2C ¨ CHCH2CH(CH3)CH ¨ C(CH3)CH ¨ CHCOCH3

178.28

228.20

7, 23

2, 719

d 149

0.4 aq; s alc, bz

0.934

1.465320

0.925

1.446020

175

51

0.835

1.459520

160

51

0.98330 20

1.433528

65

23

1445mm

i aq; s alc, eth

i aq; s alc, eth

790.05mm

10, 894

(Z)-2-Dimethylcrotonic acid, m162 Dimethyl 1,4-cyclohexanedione-2,5dicarboxylic acid, d514

155–157

Dimethyl diphenyl sulfone 4,4-dicarboxylate, s26

1.217

1.218

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d515

d516 d517

d518

d519 d520 d521 d522 d523

d524 d525 d526 d527 d528

Name 2,3-Dimethyl-1,3dioxolane-4methanol Dimethyl disulfide Dimethyldithiocarbamic acid dihydrate, Na salt Dimethyl ether

Dimethylethoxyphenylsilane N,N-Dimethylethylamine N,N-Dimethylethylenediamine N,N-Dimethylformamide N,N-Dimethylformamide dimethyl acetal Dimethyl fumarate 2,5-Dimethylfuran Dimethylglyoxime 2,4-Dimethyl-2,6heptadienal 2,4-Dimethyl-2,6heptadien-1-ol

Formula

Formula weight

Beilstein reference

132.16

CH3SSCH3 (CH3)2NCSSNa · 2H2O (CH3)2O

C2H5O(C6H5)Si(CH3)2

Density

Refractive index

1.06420 4

1.438320

1.525320

94.20 179.24

1, 291 4, 75

1.046

46.07

1, 281

0.66120

180.3

0.926320 4

1.479920

C2H5N(CH3)2

73.14

4, 94

0.675

1.372020

(CH3)2NCH2CH2NH2

88.15

42, 690

0.803

1.426020

(CH3)2NCHO

73.10

4, 58

0.944525 4

1.428225

0.897

1.397220

1.045106 0.900020 4

1.441420

(CH3)2NCH(OCH3)2

119.16

CH3OOCCH ¨ CHCOOCH3 (CH3)2(C4H2O) CH3C( ¨ NOH)C( ¨ NOH)CH3 H2C ¨ CHCH2CH(CH3)CH ¨ C(CH3)CHO H2C ¨ CHCH2CH(CH3)CH ¨ C(CH3)CH2OH

144.13 96.13 116.12

2, 741 17, 41 1, 772

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

188–189

80

misc aq, alc, eth

84.7

109.8

24

i aq; misc alc, eth

141.5

24.9

41

35% aq (5 atm); 15% bz; 11.8% acet

9335mm 140

36–38

36 23

60.4

153.0

57

103720mm

7

105 193 62 93 238–240

138.21

472mm

140.23

8810mm

1

misc aq, alc, bz, eth

sl s alc, eth i aq; misc alc, eth s alc, acet, eth, pyr

d529 d530 d531 d532 d533

2,6-Dimethyl-2,5heptadien-4-one Dimethyl heptanedioate 2,6-Dimethyl-4heptanone 2,5-Dimethyl-2,4hexadiene 2,5-Dimethylhexane

d534

2,5-Dimethyl-2,5hexanediamine d534a Dimethyl hexanedioate d535 2,5-Dimethyl-2,5hexanediol d536 1,5-Dimethylhexylamine d537 2,5-Dimethyl-3hexyne-2,5-diol Dimethyleneimine, e131 Dimethylene oxide, e129

(CH3)2C ¨ CHC( ¨ O)CH ¨ C(CH3)2 CH3OOC(CH2)5COOCH3

138.21

1, 751

0.88520 4

1.496821

28

198–199

79

sl s aq; s alc, eth

188.22

21, 281

1.062520 4

1.431420

21

12211mm

 112

s alc

[(CH3)2CHCH2]2C ¨ O

142.24

1, 710

0.80620 20

1.411420

41.5

168.1

48

(CH3)2C ¨ CHCH ¨ C(CH3)2 (CH3)2CHCH2CH2CH(CH3)2 [(CH3)2C(NH2)CH2 ˆ ]2

110.20

1, 259

0.763620 4

1.474120

12–14

132–134

29

0.06 aq; misc alc, bz, chl, eth i aq; s alc, eth

114.24

13, 283

0.693620 4

1.392520

91.2

109.1

26

i aq; sl s alc; s eth

144.26

0.832

1.445920

648mm

62

CH3OOC(CH2)4COOCH3

174.20

1, 652

1.060020 4

1.428520

8

11210mm

107

[(CH3)2C(OH)CH2 ˆ ]2

146.23

1, 492

86–90

214–215

126

(CH3)2CH(CH2)3CH(NH2)CH3 (CH3)2CC ˜ CC(CH3)2 OH OH

129.25

154–156

48

142.20

0.767 1, 501

N,N-Dimethylethanolamine, d465 Dimethyl glutarate, d574

1.420920 94–95

i aq; s alc, eth

205–206

Dimethylglutaric acids, d575, d576

1.219

1.220

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

5,5-Dimethylhydantoin d539 1,1-Dimethylhydrazine d540 1,2-Dimethylhydrazine d541 Dimethyl hydrogen phosphonate d542 1,2-Dimethylimidazole d543 1,3-Dimethyl-2imidazolidinone d543a Dimethylketene d544 Dimethyl maleate d545 Dimethyl malonate

Formula weight

Beilstein reference

128.13

24, 289

(CH3)2NNH2

60.10

4, 547

0.79122 4

1.407520

CH3NHNHCH3

60.10

4, 547

0.827420 4

1.420920

81

110.05

1, 285

1.20020 4

1.400920

170–171

96.13

23, 66

1.084

Formula

d538

d546 d547 d548 d549

d550 d551 d552

Dimethylmercury 3,4-Dimethyl-1methoxybenzene 3,5-Dimethyl-1methoxybenzene N,N-Dimethylmethyleneammonium iodide Dimethyl methylenesuccinate Dimethyl methylphosphonate Dimethyl methylsuccinate

(CH3O)2P( ¨ O)H

114.15

Density

Refractive index

Melting point

Boiling point

176–178 58

29–30

1.044

1.472020 97.5 17.5 62

Flash point

204

v s aq, alc, bz, chl, eth, acet 1 misc aq, alc, eth, PE flamm- misc aq, alc, eth, able PE 96 s aq(hyd); misc alc, acet, eth 92

10817mm

80

63.9

(CH3)2C ¨ C ¨ O CH3OOCCH ¨ CHCOOCH3 CH3OOCCH2COOCH3

70.09 144.13 132.12

1, 731 2, 751 2, 572

1.151320 1.15420 4

1.442220 1.413520

(CH3)2Hg (CH3)2C6H3OCH3

230.66 136.19

4, 678 6, 481

3.187420 0.974414 4

1.545220 1.519814

92740mm 200

(CH3)2C6H3OCH3

136.19

6, 493

0.962715 4

1.510715

193

 H2CN(CH3) 2I

185.01

44, 153

CH3OOCCH2C( ¨ CH2)COOCH3 (CH3O)2P(O)CH3

158.15

2, 762

1.124118 4

1.444220

124.08

41, 572

1.145

1.413020

181

43

160.17

23, 1696

1.076

1.420020

196

83

CH3OOCCH2CH(CH3)COOCH3

Solubility in 100 parts solvent

34 200.4 180–181

90

65

d aq, alc; s eth 8.7 aq sl s aq; misc alc, eth i aq; s alc, eth i aq; s alc, bz, eth i aq; s alc, bz, eth

219 d

38

208

s alc, eth

d553 d554 d555 d556 d557 d558 d559 d560 d561

2,6-Dimethylmorpholine 2,3-Dimethylnaphthalene 2,6-Dimethylnaphthalene 1,2-Dimethyl-3nitrobenzene 1,2-Dimethyl-4nitrobenzene 1,3-Dimethyl-2nitrobenzene 1,3-Dimethyl-4nitrobenzene N,N-Dimethyl-4nitrosoaniline Dimethyl 2-nitro1,4-phthalate

0.934620

115.18

1.447020

85

147

48

misc aq, alc, bz

(CH3)2C10H6

156.23

5, 571

1.00820 4

102–104 269

sl s alc; s bz, eth

(CH3)2C10H6

156.23

5, 570

1.14204

110.2

262

i aq; sl s alc

(CH3)2C6H3NO2

151.17

5, 367

1.129

7–9

245

(CH3)2C6H3NO2

151.17

5, 368

1.139

29–31

14320mm

(CH3)2C6H3NO2

151.17

5, 378

1.112

1.522020

14–16

225744mm

87

i aq; s alc

(CH3)2C6H3NO2

151.17

5, 378

1.117

1.549720

2

237–239

107

s alc, bz, chl, eth

(CH3)2NC6H4NO

150.18

12, 677

86

flammable solid

O2NC6H3(COOCH3)2

239.18

9, 826

72–75

Dimethyl isophthalate, d589 1,4a-Dimethyl-7-isopropyl-1,2,3,4,4a,9,10,10aoctahydro-1-phenanthrenemethylamine, d20

1.543420

Dimethyl itaconate, d550 2,2-Dimethyl-3-methylenenorbornane, c2 6,6-Dimethyl-2-methylenenorpinene, p176

107

i aq; s alc i aq; s alc

i aq; s alc, eth

1.221

1.222

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d562

Name

d569

cis-3,7-Dimethyl2,6-octadienal trans-3,7-Dimethyl2,6-octadienal 3,7-Dimethyl-2,6octadienenitrile Dimethyl octanedioate Dimethyl oxalate N1-(4,5-Dimethyloxazol-2-yl)sulfanilamide N-(1,1-Dimethyl-3oxobutyl)acrylamide 2,3-Dimethylpentanal

d570 d571

2,2-Dimethylpentane 2,3-Dimethylpentane

d572 d573 d574

2,4-Dimethylpentane 3,3-Dimethylpentane Dimethyl pentanedioate 2,2-Dimethylpentanedioic acid 3,3-Dimethylpentanedioic acid

d563 d564 d565 d566 d567

d568

d575 d576

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

152.24

0.888820 4

1.489820

229

101

misc alc, eth, glyc

152.24

0.886920 4

1.486920

229

101

misc alc, eth, glyc

149.24

0.853

1.475320

202.25

2, 693

1.021020 4

1.432520

4.8

CH3OOCCOOCH3

118.08 267.31

2, 534

1.14854

1.37980

50–54 163.5 193–194

CH2 ¨ CHC( ¨ O)NHC(CH3)2CH2COCH3

169.23

CH3CH2CH(CH3)CH(CH3)CHO CH3CH2CH2C(CH3)3 CH3CH2CH(CH3)CH(CH3)2 (CH3)2CHCH2CH(CH3)2 CH3CH2C(CH3)2CH2CH3 CH3OOC(CH2)3COOCH3 HOOCC(CH3)2CH2CH2COOH (CH3)2C(CH2COOH)2

114.19

57–58

1.413220

Solubility in 100 parts solvent

112

CH3OOC(CH2)6COOCH3

0.832

Flash point

268

i aq; s alc 75

6 aq; s alc, eth s aq, acids, alk

1208mm

58

100.21 100.21

1, 157 12, 120

0.67420 4 0.695120 4

1.382420 1.392020

123.8 glass

79.2 89.8

15 6

i aq; s alc, eth i aq; s alc, eth

100.21 100.21 160.17

1, 158 2, 633

0.672720 4 0.693320 4 1.093415 4

1.381520 1.390520 1.423420

119.2 134.4

80.5 86.1 6 94–9513mm 102

s alc, eth i aq; s alc, eth v s alc, eth

160.17

2, 676

83–85

v s aq, alc, chl

160.17

2, 684

100–103

v s aq, alc, eth

d577 d578 d579 d580 d581 d582 d583 d584 d585 d586 d587

2,4-Dimethyl-3pentanol 2,4-Dimethyl-3pentanone 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol Dimethylphenylchlorosilane 4,5-Dimethyl-ophenylenediamine Dimethylphenylsilane

3,7-Dimethyl-6-octen-1-o1, c274 Dimethylolpropionic acid,

116.20

1, 417

0.82920 4

1.425420

70

140

37

sl s aq; s alc, eth

114.19

1, 703

0.806220 4

1.398620

80

124

15

misc alc, eth; s bz

122.17 122.17 122.17 122.17 122.17 122.17 170.7

6, 480 6, 486 6, 494 6, 485 6, 480 6, 492

1.542020 1.539020

75 27 74.5 49.0 62.5 64–68

218 210–212 211.5 203 225 219.5 192–193

(CH3)2C6H2(NH2)2

136.20

13, 179

(CH3)2Si(H)C6H5

136.3

(CH3)2CHCH(OH)CH(CH3)2 (CH3)2CHC( ¨ O)CH(CH3)2 (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2C6H3OH (CH3)2Si(Cl)C6H5

1.027614 4 0.96580 1.06428 4 1.00828 4 1.03220 4

1.50820

112 73

v s alc, bz, chl, eth v s alc, bz, chl, eth v s alc, bz, chl, eth v s alc, bz, chl, eth v s alc, bz, chl, eth v s alc, bz, chl, eth

127–129 0.889120 4

1.499520

156–157

Dimethyl 3-oxoglutarate, d459 2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one, a309 1,5-Dimethyl-2-phenyl-4-aminopyrazolone, a113

1.223

1.224

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d588 d589 d590 d591 d592 d593 d594 d595 d596 d597 d598 d599 d600 d601 d602

Name Dimethyl-ophthalate Dimethyl-mphthalate Dimethyl -pphthalate 2,6-Dimethylpiperidine 2,2-Dimethylpropane N,N-Dimethyl-1,3propanediamine 2,2-Dimethyl-1,3propanediol 2,2-Dimethyl-1propanol 2,2-Dimethylpropionaldehyde 2,2-Dimethyl propionamide 2,2-Dimethylpropionic acid 2,2-Dimethylpropionic anhydride 2,2-Dimethylpropionyl chloride 1,1-Dimethylpropylamine 1,1-Dimethyl-2propynylamine

Formula weight

Beilstein reference

Density

Refractive index

Melting point

C6H4(COOCH3)2

194.19

9, 797

1.194020 20

1.51521

5.5

283.7

C6H4(COOCH3)2

194.19

9, 834

1.19420 4

1.516820

67–68

282

C6H4(COOCH3)2

194.19

4.3303

1.2

113.20

20, 108

0.840

1.439420

0.6130 0.812

1.34766 1.435020

Formula

Boiling point

Flash point 146

140–142 288

16.6

127

11

9.5 123

35

72.15 102.18

(CH3)2C(CH2OH)2

104.15

1, 483

1.1125

127–128 208–210

88.15

1, 406

0.81220 4

52–54

113.1

36

6

74730mm

1

0.793

1.379420

(CH3)3CCHO

186.25

(CH3)3CC(O)NH2

101.15

2, 320

(CH3)3CCOOH

102.13

2, 319

0.90550

1.393137

[(CH3)3CC(O)]2O

186.25

2, 320

0.918

(CH3)3CCOCl

120.58

2, 320

CH3CH2C(CH3)2NH2

87.17

4, 179

HC ˜ CC(CH3)2NH2

83.13

0.4 aq; misc alc, chl, eth; i PE i aq i aq, hot alc,eth

(CH3)4C (CH3)2N(CH2)3NH2

(CH3)3CCH2OH

Solubility in 100 parts solvent

180 aq; 12 bz; 60 acet; v s alc, eth 3.6 aq; misc alc, eth

154–157 212 35.5

163.8

63

1.409220

193

57

0.979

1.412020

105–106

1

d aq, alc; v s eth

0.73125 4

1.399620

77

65

misc aq, alc, eth

0.790

1.423520

79–80

1

105

2.5 aq; v s alc, eth

d603 d604 d605 d606 d607 d608 d609 d610

d611 d612 d613 d614 d615

3,5-Dimethylpyrazole 2,4-Dimethylpyridine

96.13

23, 74

(CH3)2(C5H3N)

107.16

20, 244

0.92725 4

2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine Dimethyl succinate Dimethylsulfamoyl chloride Dimethyl sulfate

(CH3)2(C5H3N) (CH3)2(C5H3N) (CH3)2(C5H3N) CH3OOCCH2CH2COOCH3 (CH3)2NSO2Cl

107.16 107.16 107.16 146.14 143.59

20, 244 20, 246 20, 246 2, 609 4, 84

(CH3O)2SO2

126.13

Dimethyl sulfide Dimethyl sulfite Dimethyl sulfone Dimethyl sulfoxide Dimethyl-d6 sulfoxide

(CH3)2S (CH3O)2SO (CH3)2SO2 (CH3)2SO (CD3)2SO

62.13 110.13 94.13 78.13 84.18

Dimethyl phosphite, d541 Dimethyl pimelate, d530 Dimethyl propanedioate, d545

108

218

1.499120

60

158.3

37

0.920025 4 0.93925 4 0.93925 4 1.20218 4 1.337

1.495625 1.510025 1.503325 1.419020 1.451820

6.0 12 9 19.5

143–144 164 170 195–200 11475mm

33 53 53 85

1, 283

1.332220 4

1.387420

31.8

188 d

83

1, 288 1, 282 1, 289 1, 289

0.84621 4 1.294

1.435420 1.408320

98.3

1.10020 4 1.18

1.478320 1.475820

37.3 126–127 238 189.0 555mm

36 30 143 95 95

1,1-Dimethylpropargylamine, d602 N-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide, s21

109 18.5

s aq; v s bz, eth

Dimethyl sebacate, d512 Dimethyl suberate, d565

17 aq; v s alc, bz, eth 43 aq45; s alc, eth sl s aq; s alc, eth s aq, alc, eth 0.83 aq; 2.9 alc

2.8 aq(hyd); s acet, bz, diox, eth 2 aq; s alc, eth v s aq, alc, acet s alc, acet, bz, chl

1.225

1.226

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d616

Name

Formula

Formula weight

Beilstein reference

Density

CH3OOCCH(OH)CH(OH)COOCH3 (CH3)2Te (CH3)2(C4H6O)

178.14

3, 510

1.32820 4

157.68 100.16

1, 291 17, 14

0.833

(CH3OOCCH2CH2)2S

206.26

Refractive index

Melting point

16323mm

10 1.4041

91–92 90–92

26

1.198

1.474020

14818mm

112

1.047

1.575720

581mm

99

d623 d624 d625 d626

2,4-Dinitroaniline 1,3-Dinitrobenzene

(O2N)2C6H3NH2 C6H4(NO2)2

183.12 168.11

12, 747 5, 258

d627

2,4-Dinitrobenzenesulfenyl chloride 3,4-Dinitrobenzoic acid 3,5-Dinitrobenzoic acid 3,5-Dinitrobenzoyl chloride 2,6-Dinitro-p-cresol

(O2N)2C6H3SCl

234.62

62, 316

96

(O2N)2C6H3COOH

212.12

9, 413

166

(O2N)2C6H3COOH

212.12

9, 413

207

(O2N)2C6H3COCl

230.56

9, 414

69.5

(O2N)2C6H2(OH)CH3

198.13

6, 414

77–79 (anhyd)

d619 d620 d621 d622

d628 d629 d630 d631

(CH3)2NC(S)H

89.16

4, 70

(CH3NH)2C ¨ S

104.18

4, 70

CH3C6H4N(CH3)2

135.21

12, 902

(CH3NH)2C ¨ O (CH3)2Zn

88.11 95.45

Flash point

48–50

()-DimethylL-tartrate Dimethyltelluride 2,5-Dimethyltetrahydrofuran Dimethyl-3,3thiodipropionate N,N-Dimethylthioformamide N,N-Dimethylthiourea N,N-Dimethyl-ptoluidine 1,3-Dimethylurea Dimethylzinc

d617 d618

Boiling point

s aq; 200 alc15; v s bz d aq; v s alc; i eth

60–62 0.937

4, 65

1.545820

Solubility in 100 parts solvent

v s aq, alc, acet 211

1.38611 4

101–104 268–270 40 46

1.61514 1.57518 4

188 89–90

300–303

83 v s aq, alc, i eth ignites misc bz, PE; s eth in air i aq; 0.75 alc 0.05 aq; 2.7 alc; v s bz, chl, EtAc s bz, HOAc; d alc

subl

0.7 aq; v s alc, eth

19611mm

1.9 hot aq; v s alc; sl s bz, eth d aq, alc; s eth

d631a 4,6-Dinitro-o-cresol

(O2N)2C6H2(OH)CH3

198.13

6, 368

d632 d633

CH3CH(NO2)2 FC6H3(NO2)2

120.07 186.10

1, 102 5, 262

C10H6(NO2)2

218.17

5, 558

(O2N)2C6H3OH

184.11

6, 251

(O2N)2C6H3CH2COOH

226.15

9, 459

169–175

(O2N)2C6H3NHNH2

198.14

15, 489

200

(O2N)2C6H2(OH)COOH

228.12

10, 122

169–172

CH3C6H3(NO2)2 CH3C6H3(NO2)2 CH3C6H3(NO2)2 C9H19OOC(CH2)4COOC9H19 (C18H37O)P(O)H

182.14 182.14 182.14 398.63

5, 339 5, 341 5, 341

d634 d635

1,1-Dinitroethane 2,4-Dinitro-1fluorobenzene 1,5-Dinitronaphthalene 2,4-Dinitrophenol

d636

2,4-Dinitrophenylacetic acid d637 2,4-Dinitrophenylhydrazine d638 3,5-Dinitrosalicyclic acid d639 2,4-Dinitrotoluene d640 2,6-Dinitrotoluene d641 3,4-Dinitrotoluene d641a Dinonyl hexanedioate d642 d643 d644 d645

Dioctadecyl phosphite Dioctylamine Dioctyl sulfide 4,9-Dioxa-1,12dodecanediamine

Dimethyl terephthalate, d590 2,3-Dimethylvaleraldehyde, d569 2,4-Dinitrochlorobenzene, c94

(C8H17)2NH (C8H17)2S H2N(CH2)3O(CH2)4O(CH2)3NH2

87.5 1.350324 24 1.569020

185–186 17825mm

112

216–217 subl 1.683

s bz; v s eth; sl s alc s alc, bz; 16 EtAc; 36 acet; 5 chl; 20 pyr s alc, eth

112–114

1.32171 1.442 1.2833111 1.479 1.2594111 0.91725 25

586.97 241.46 258.51 204.32

26

64.66 64–66 54–57

v s alc, acet, eth, alk s alc, eth s bz, eth, glyc

flammable solid

sl s aq, alc; s acid s aq; v s alc, eth

300 sl d

1.2 alc; 9 eth s alc i aq; s alc 218

57–59 4, 196 1, 419

14–16 0.842 0.962

3,4-Dinitrochlorobenzene, c95 3,5-Dinitro-1-toluic acid, m228 Dioctyl phthalates, b179, d313

1.461020 1.460920

298 18010mm 134– 1364mm

112 112 112

i aq; v s alc, eth

6,8-Dioxabicylco[3.2.1]octan-7-one, h183

1.227

1.228

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

88.10

19, 3

1.032920 4

1.422420

11.7

74.08 254.28

192, 3

1.06020 4

1.400020

95 74–75 215–218

1.473920 1.4272 1.412020

d646

1,4-Dioxane

d647 d648

1,3-Dioxolane Dipentaerythritol

d649 d650 d651

Dipentene Dipentylamine Dipentyl ether

(C5H11)2NH (C5H11)2O

136.24 157.29 158.29

5, 137 41, 378 11, 193

0.840221 4 0.777 0.783320 4

d652

Diphenylacetic acid

(C6H5)2CHCOOH

212.25

9, 673

1.25815 15

d653 d654 d655 d656

Diphenylacetonitrile Diphenylacetylene Diphenylamine cis,cis-1,4Diphenyl-1,3-butadiene cis,trans-1,4Diphenyl-1,3diene 1,3-Diphenyl-2buten-1-one Diphenylcarbamoyl chloride 1,5-Diphenylcarbohydrazide Diphenyl carbonate Diphenyl chlorophosphate

(C6H5)2CHCN C6H5C ˜ CC6H5 (C6H5)2NH C6H5CH ¨ CHCH ¨ CHC6H5

193.25 178.23 169.23 206.29

9, 674 5, 656 12, 174 5, 676

C6H5CH ¨ CHCH ¨ CHC6H5

206.29

5, 676

0.990 1.160 0.9697101 1.6347101 4 (He line) 0.997422 1.605322 4

C6H5C(O)CH ¨ C(C6H5)CH3 (C6H5)2NCOCl

222.27

72, 433

1.108015 4

(C6H5NHNH)2C ¨ O

242.28

15, 292

(C6H5O)2C ¨ O (C6H5O)2P(O)Cl

214.22 268.64

6, 158 6, 179

d657

d658 d659 d660 d661 d662

(HOCH2)3CCH2OCH2C(CH2OH)3

1.634320

231.68

Boiling point 101.2

Flash point 12 1

42 39 63

69.4 148

1955mm

76 60–61 53–54 70.5

18112mm 300 302

88

1330.1mm

s alc, bz, eth, chl

30 glass 82–84

24650mm

i aq; s alc, eth

80–81 1.550020

misc aq, alc, bz, chl, eth, PE misc aq; s alc, eth

176 195–202 186.8

152

168–171

1.296

Solubility in 100 parts solvent

302–306 314272mm

i aq; misc alc v s alc, eth misc alc, eth; s acet s hot aq, alc, chl, eth s alc, eth v s hot alc, eth 45 alc; v s bz, eth s bz, chl, eth, PE

s hot alc, acet, HOAc s hot alc, bz, eth 112

d663 d664 d665

Diphenyl diselenide Diphenyl disulfide Diphenylenimine

C6H5SeSeC6H5 C6H5SSC6H5

312.13 218.34 167.21

6, 346 6, 323 20, 433

1.55780 4 1.35320 4 18 1.104

d666 d667

1,2-Diphenylethane Diphenyl ether

C6H5CH2CH2C6H5 C6H5OC6H5

182.27 170.21

5, 598 6, 146

0.99520 4 1.066120 4

1.5338 1.576330

d668

1,2-Diphenylethylamine N,N-Diphenylethylenediamine N,N-Diphenylformamidine 1,3-Diphenylguanidine

C6H5CH2CH(C6H5)NH2

197.28

12, 1326

1.020

1.580220

C6H5NHCH2CH2NHC6H5

212.30

12, 543

67.5

C6H5N ¨ CHNHC6H5

196.25

12, 236

138–141

C6H5NHC( ¨ NH)NHC6H5

211.27

12, 369

d669 d670 d671

3,6-Dioxa-1,8-octanediol, t270 4,8-Dioxa-1,11-undecanediol, t408 (2,5-Dioxo-4-imidazolidinyl)urea, a77 1,3-Dioxolane-2-one, e124 3,4-Dioxypentane, d439 Dipentyl ketone, u6

1.13

Diphenic acid, b137 Diphenylacetone, d684 Diphenylcarbamyl chloride, d659 sym-Diphenylcarbazide, d660 Diphenyldiazone, a322 Diphenylethanedione, b34

61–64 58–60 246

310 355

52.5 26.9

284 258.3

115

311

112

150

228–330

s hot alc s alc, bz, eth; i aq 0.8 bz; 3 eth; 16 pyr; 11 acet; i aq s alc; v s chl, eth s alc, bz, eth, HOAc

v s alc, eth s eth; v s chl

d 170

s alc, hot bz, chl

Diphenylethanedione dioxime, b35 1,2-Diphenylethene, s9 Diphenylethyne, d654 Diphenylglycolic acid, b36 Diphenylglyoxime, b35

1.229

1.230

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d672 d673 d674 d675 d676 d677

Name 5,5-Diphenylhydantoin 1,2-Diphenylhydrazine Diphenyl isooctylphosphite Diphenylmercury Diphenylmethane Diphenylmethanol

d678

1,1-Diphenylmethylamine

d679 d680 d681 d682

2,5-Diphenyloxazole 2,6-Diphenylphenol Diphenyl phosphite Diphenylphosphoryl azide 2,2-Diphenyl-1picrylhydrazyl 1,3-Diphenyl-2propanone 1,3-Diphenyl-2propen-1-one 2,2-Diphenylpropionic acid Diphenylsilanediol Diphenyl sulfide Diphenyl sulfone

d683 d684 d685 d686 d687 d688 d689

Formula weight

Beilstein reference

252.27

24, 410

C6H5NHNHC6H5

184.24

15, 123

(CH3)2CH(CH2)5PH(OC6H5)2 (C6H5)2Hg C6H5CH2C6H5 (C6H5)2CHOH

346.40 354.81 168.24 184.24

C6H5CH(NH2)C6H5

(C6H5)2C6H3OH (C6H5O)2P( ¨ O)H (C6H5O)2P( ¨ O)N3

Formula

Density

Refractive index

1.15816 4

16, 946 52, 498 6, 678

2.3184 1.342110 4

1.5768

183.25

12, 1323

1.595699 1.063522 4 supercooled

221.26 246.31 234.19 275.20

27, 78 63, 3631 61, 94

394.32

162, 363

210.28

7, 445

1.2 1.071262 4

7, 478

226.28

92, 474

(C6H5)2Si(OH)2 (C6H5)2S (C6H5)2SO2

216.31 186.28 218.27

16, 909 6, 299 6, 300

Flash point

1.223 1.277

1.557520 1.551820

Solubility in 100 parts solvent i aq; 1.7 alc; 3.3 acet v s alc; sl s bz

123–126 1.522

208.26

Boiling point

295–298

1.044

C6H5CH2C( ¨ O)CH2C6H5 C6H5CH ¨ CHC( ¨ O)C6H5 CH3C(C6H5)2COOH

Melting point

124–125 d  306 25.9 264.5 66.7 298

112

34

112

295

72–73 360 100–102 12 21926mm 1570.17mm

s chl; sl s hot alc v s alc, bz, chl, eth 0.05 aq; v s alc, chl, eth sl s aq

176 112

127 d

1.645862

32–34

330

i aq; v s alc, eth

57–58

20825mm

v s bz, chl, eth

175–177 300 1.11815 15

1.632720

140 d 40 296 128–129 379

s alc; v s bz, eth 53 112

misc bz, eth, CS2 i aq; s hot alc, bz

d690 d691 d692 d693 d694 d695 d696 d697

Diphenyl sulfoxide Diphenylthiocarbazone 1,3-Diphenylthiourea 1,3-Diphenylurea

202.28 256.33

6, 300 16, 26

228.32

12, 394

1.32

154

C6H5NHC(O)NHC6H5

212.25

12, 352

1.239

238

260 d

196.34

201, 19

0.916

1.487620

0.5

265

110

182.31 101.19

4, 138

0.915 0.737520 4

1.482020 1.404320

39.6

12315mm 109.2

17

0.91725 25

1.42525

229

113

1,2-Dipiperidinoethane Dipiperidinomethane Dipropylamine

(C3H7)2NH

Dipropylene glycol butyl ether

CH3CH(OH)CH2OCH2CH(OC4H9)CH3

5,5-Diphenyl-2,4-imidazolidinedione, d672 Diphenyl ketone, b53 Diphenyl oxide, d667 Diphenylphosphorochloridate, d662

190.3

69–71 168 d

20713mm

(C6H5)2S ¨ O C6H5N ¨ NC(S)NHNHC6H5 C6H5NHC(S)NHC6H5

1,3-Diphenyl-1,3-propanedione, d53 sym-Diphenylthiourea, t146 Dipicolinic acid, p261 Di-2-propenylamine, d25

i aq; v s chl, CCl4 i aq; v s alc, eth 0.015 aq; s eth, HOAc

4 aq; v s alc, eth, PE

Dipropyl adipate, d702 Dipropylene glycol, h172

1.231

1.232

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d698 d699 d700 d701 d702 d703 d704 d705 d706 d707 d708 d709 d710 d711 d712 d713 d714

Name Dipropylene glycol ethyl ether Dipropylene glycol isopropyl ether Dipropylene glycol methyl ether Dipropyl ether Dipropyl hexanedioate Dipropyl sulfate Dipropyl sulfone 2,2-Dipyridyl 2,2-Dipyridylamine 1,3-Dithiane 4,4-Dithiobutyric acid 3,3-Dithiopropionic acid Dithiooxamide 1,3-Di-o-tolylguanidine 1,5-Di(vinyloxy)-3oxapentane 1,3-Divinyltetramethyldisiloxane 3,9-Divinyl-2,4,8,10tetraoxaspiro[5.5]undecane

Formula CH3CH(OH)CH2OCH2CH(OC2H5)CH3 CH3CH(OH)CH2OCH2CH[OCH(CH3)2]CH3 CH3CH(OH)CH2OCH2CH(OCH3)CH3 (C3H7)2O C3H7OOC(CH2)4COOC3H7 (C3H7O)2SO2 (C3H7)2SO2

HOOC(CH2)3SS(CH2)3COOH HOOCCH2CH2SSCH2CH2COOH H2NC( ¨ S)C( ¨ S)NH2 (CH3C6H4NH)2C ¨ NH

Formula weight

Beilstein reference

Density

Refractive index

162.2

0.93025 25

1.41925

388

90

176.2

0.87825 25

1.42125

80.1

90

148.2

0.95120 20

1.41920

117

188.3

85

1.380320 1.431420

123.2 20

89.6 14410mm

4

d 140 28–30 69.7

12020mm 270 273

89–90 53–55 110

22250mm

102.18 230.30

1, 354 22, 574

0.746620 0.979020 4

182.24 150.24 156.19

1, 354 1, 359 23, 199

1.10620 4 1.02850 4

171.20 120.24 238.32

221, 630 3, 312

210.27 120.20 239.32

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

0.4 aq i aq; s alc, eth v s PE

126 0.5 aq; v s alc, bz, chl, eth, PE 90

157–159 2, 565 12, 803

170 d subl 176–178

1.1020 4

(CH2 ¨ CHOCH2CH2)2O

158.20

0.97529

1.445

[CH2 ¨ CHSi(CH3)2]2O

186.39

0.81120 4

1.41220

212.25

1.251

sl s aq; s alc; i eth s hot alc, eth

8110mm 99.7

139

40–54

1202mm

110

d715 d716 d717 d718 d719 d720 d721 d722

Docosane Docosanoic acid 1-Docosanol 1H, H, 7H- Dodecafluoro-1-heptanol Dodecane 1,12-Dodecanediamine Dodecanedioic acid 1,2-Dodecanediol

d723 d724

1,12-Dodecanediol Dodecanenitrile

CH3(CH2)20CH3 CH3(CH2)20COOH CH3(CH2)21OH HCF2(CF2)5CH2OH

310.61 340.60 326.61 332.0

1, 174 2, 391 1, 431

CH3(CH2)10CH3 H2N(CH2)12NH2 HOOC(CH2)10COOH CH3(CH2)9CH(OH)CH2OH HOCH2(CH2)10CH2OH CH3(CH2)10CN

170.41 200.37 230.30 202.34

1, 171 4, 273 2, 729 13, 2237

202.34 181.32

12, 562 2, 363

0.778245 1.435845 0.8221100 1.4270100 4 1.761620

1.318020

0.749020 4

1.421620

44.4 80–82 65–72

369 20660mm 1800.22mm 169–170

9.6 216.28 62–65 128–130 24510mm 58–60

0.827

1.4360

18912mm 198100mm

0.84520 20

1.458720

266–283

81–84 20

d725

1-Dodecanethiol

CH3(CH2)11SH

202.40

d726

Dodecanoic acid

CH3(CH2)10COOH

200.32

2, 359

0.86954

1.418382

44

225100mm

d727 d728 d729

1-Dodecanol Dodecanoyl chloride 1-Dodecene

CH3(CH2)11OH CH3(CH2)10COCl CH3(CH2)9CH ¨ CH2

186.34 218.77 168.32

1, 428 2, 363 1, 225

0.830825 4 0.946 0.758420 4

1.441325 1.445920 1.429420

23.8

259 13411mm 213.4

Dipropyl ketone, h17 Distearylpentaerythritoldiphosphite, b196 Disulfiram, t61 2,3-Dithiabutane, d516

5,6-Dithiadecane, d113 3,4-Dithiahexane, d294 2,2-Dithiodiethanol, h118 1,4-Dithiothreitol, d424

35.2

Dithizone, d691 Divinylene oxide, f40 DMSO, d614 Dodecyl alcohol, d727

i aq; sl s alc; v s eth 0.2 alc; 0.19 eth sl s eth; s alc, chl

71 155

112 87

112 112 77

misc alc, bz, chl, eth i aq; s alc, eth i aq; 100 alc; v s bz, eth i aq; s alc, eth s alc, eth, PE

1.233

1.234

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. d730

Name

Formula

Formula weight

Beilstein reference

d731 d732

2-Dodecen-1-ylsuccinic anhydride Dodecanal Dodecylamine

CH3(CH2)10CHO CH3(CH2)11NH2

184.32 185.36

1, 714 4, 200

d733

4-Dodecylaniline

CH3(CH2)11C6H4NH2

261.46

123, 2776

d734 d735

CH3(CH2)11C6H11 CH3(CH2)11OSO3Na

252.50 288.38

CH3(CH2)11SiCl3

303.8

d737 d738

Dodecylcyclohexane Dodecyl sulfate, Na salt Dodecyltrichlorosilane Dotriacontane Dulcitol

CH3(CH2)30CH3

450.88 182.17

1, 177 1, 544

e1

D-Ephedrine

165.24

e2

L-Ephedrine

CH3NHCH(CH3)CH(OH)C6H5 CH3NHCH(CH3)CH(OH)C6H5

e3

1,2-Epoxybutane

e4

1,2-Epoxycyclododecane 1,2-Epoxycyclohexane 1,4-Epoxycyclohexane 2-(3,4-Epoxycyclohexyl)ethyltrimethoxysilane

d736

e5 e6 e7

Density

Refractive index

Melting point

266.38 0.835

1.434420 28–30 40–41

0.8250

1.458020

12 204–207

1.45820 0.812420 4 1.4720

1.436470

Boiling point

Flash point

1805mm

177

185100mm 247–249

101 112

Solubility in 100 parts solvent

misc alc, bz, chl, eth

220– 22115mm 1310.8mm 10 aq 15510mm

68–70 467 188–189 2751mm

sl s alc, bz, eth 3.3 aq; sl s alc

13, 637

119

225

v s alc, eth

165.24

13, 636

34

255

5 aq; v s alc; s chl

72.11

172, 17

150

63.2

17

6 aq; misc alc, bz, chl, eth

v s alc, bz, eth

182.31 98.15 98.15 246.37

17, 21

0.829720

1.384020

0.939

1.477320

0.970

1.45202

129–130

27

0.969 1.07025 4

1.448020 1.44925

119713mm 310

12 146

e7a e8

126.20 84.12

17, 21

0.964

1.433620

120.15

17, 49

1.052316 4

1.533820

e10

1,2-Epoxycyclooctane 1,2-Epoxycyclopentane 1,2-Epoxyethylbenzene 1,2-Epoxy-3-phenoxypropane 1,2-Epoxypropane

58.08

17, 6

0.85904

1.366020

e11

2,3-Epoxy-1-propanol

74.08

17, 104

1.114325 4

1.431520

e9 e9a

Dodecyl aldehyde DPPH, d683 Durene, t99 Durenol, t116 EDTA, e125

150.18

53–56

555mm 102

56 10

37

194

79

i aq; s alc, eth

34.2

37

662.5mm

81

41 aq; misc alc, eth misc aq

2

Eicosane, i2 1-Eicosene, i3 Elaidic acid, o11 Embonic acid, m235 Enanthic acid, h10

112.1

Epibromohydrin, b276 Epichlorohydrin, c101 1,4-Epoxybutane, t66 Epoxyethane, e129 1,3-Epoxypropane, t345

1.235

1.236

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

1.042

1.449420

189

83

172, 14

1.495

1.477820

151745mm

66

183.3

88.6

8.5 12.6

117.3 197.3

33 110

31

190.2

82

146 171

50

v s alc, alk d aq, alc; v s eth

35.0 78.3

17 8

78.8 9711mm 250 13624mm 255

12 97 115 107 112

17415mm

112

0.7 aq; s alc, eth misc aq, alc, eth, chl misc aq, alc, eth s aq, alc, eth i aq; s alc misc alc, eth v s alc, bz, eth sl s aq; s alc, eth 0.12 aq; misc alc, eth sl s aq

e12

2,3-Epoxypropyl methacrylate

H2C ¨ C(CH3)COOCH2CHˆCH2

142.15

e13

CH2CHˆCH2

161.42

e14

1,2-Epoxy-3,3,3-trichloropropane Ethane

CH3CH3

30.07

1, 80

e15 e16

1,2-Ethanediamine 1,2-Ethanediol

H2NCH2CH2NH2 HOCH2CH2OH

60.10 62.07

4, 230 1, 465

0.5462,88 1.049304, g·L 1.456820 0.897720 4 1.431820 1.113520 4

e17

CH3COOCH2CH2OOCCH3

146.14

2, 142

1.104320

1.415020

HSCH2CH2SH CH3CH2SO2Cl

94.20 128.57

1, 471 42, 526

1.12324 1.35722

1.558020 1.433920

e20 e21

1,2-Ethanediol diacetate 1,2-Ethanedithiol Ethanesulfonyl chloride Ethanethiol Ethanol

62.13 46.07

1, 340 1, 292

0.831525 0.789420 4

1.42025 1.361420

e22 e23 e24 e25 e26 e27 e28

Ethanol-d Ethoxyacetic acid 4-Ethoxyaniline 2-Ethoxybenzaldehyde 4-Ethoxybenzaldehyde 2-Ethoxybenzamide Ethoxybenzene

CH3CH2OD CH3CH2OCH2COOH CH3CH2OC6H4NH2 CH3CH2OC6H4CHO CH3CH2OC6H4CHO CH3CH2OC6H4CONH2 CH3CH2OC6H5

47.08 104.11 137.18 150.18 150.18 165.19 122.17

13, 1287 3, 233 13, 436 8, 43 8, 73 10, 93 6, 140

0.801 1.102120 4 1.065216 4 1.074 1.08025 25

1.359520 1.419020 1.560920 1.542220 1.558420

0.96720 4

1.507420

4 20 13–14 132–133 29.5 170.0

e29

2-Ethoxybenzoic acid

CH3CH2OC6H4COOH

166.18

10, 64

1.105

1.540020

19.4

e18 e19

CH3CH2SH CH3CH2OH

147.9 114.5

Flash point

Solubility in 100 parts solvent

4.7 mL aq; 46 mL alc4 misc aq, alc; i bz misc aq, alc, glyc, pyr misc alc, eth

e30 e31 e32 e33 e34 e35 e36 e37 e38 e39 e40 e41 e42 e43

4-Ethoxybenzoic acid 2-Ethoxybenzyl alcohol Ethoxycarbonyl isothiocyanate Ethoxydimethylvinylsilane 2-Ethoxyethanol

CH3CH2OC6H4COOH CH3CH2OC6H4CH2OH

166.18 152.19

10, 156 6, 893

CH3CH2OC( ¨ O)NCS

131.15

33, 279

(CH3)2Si(OC2H5)CH ¨ CH2 CH3CH2OCH2CH2OH

130.3 90.12

2-(2-Ethoxyethoxy)ethanol 2-(2-Ethoxyethoxy)ethyl acetate 2-Ethoxyethyl acetate 2-Ethoxyethylamine 3-Ethoxy-4-hydroxybenzaldehyde 3-Ethoxymethacrolein

C2H5OCH2CH2OCH2CH2OH C2H5OCH2CH2OCH2CH2OOCCH3 CH3COOCH2CH2OCH2CH3 CH3CH2OCH2CH2NH2 C2H5OC6H3(OH)CHO

134.18

4-Ethoxy-3-methoxybenzaldehyde Ethoxymethyldiphenylsilane Ethoxymethylenemalononitrile

1.237

Eschenmoser’s salt, d549 Estragole, a94 Ethanal, a4 Ethanediamide, o54 Ethanenitrile, a29

197–199

sl s hot aq

1.532120

265

1.112

1.500020

5618mm

0.79020 4

1.39820

99710mm

1, 467

0.929520

1.407520

59

134.8

48

12, 520

0.984125 4

1.425425

55

201.9

96

1.009620

1.421320

25

218.5

110

61.7

156.3

57

107

21

78– 8114mm

35

176.21 132.16

22, 155

0.974920 4

1.402320

89.14 166.18

42, 718 8, 256

0.851220 4

1.410120

C2H5OCH ¨ C(CH3)CHO

114.15

14, 4082

0.960

C2H5OC6H3(OCH3)CHO

180.20

8, 256

(C6H5)2Si(CH3)OC2H5

242.4

CH3CH2OCH ¨ C(CN)2

122.13

50

76–78 1.479220 59–60 1.01820 4

31, 162

Ethanoic acid, a19 Ethanolamine, a164 Ethenyl acetate, v2 Ethenylbenzene, s19 4-Ethoxy-m-anisaldehyde, e41

1.54420

s alc, bz, chl, eth 1220.3mm

64–66

misc aq, alc, eth, acet misc aq, alc, bz, chl, acet, pyr misc aq, alc, eth, oils 29 aq; misc alc, eth misc aq, alc, eth s eth, glycols; 50 alc

16012mm

1-Ethoxybutane, b449 Ethoxyethane, d300 2-Ethoxyethyl ether, b176 Ethoxyformic anhydride, d326

1.238

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

1.06020 4

1.604020

5.5 280 134–135

1.417820

e44 e45

1-Ethoxynaphthalene N-(4-Ethoxyphenyl)acetamide

C10H7OCH2CH3 CH3CH2OC6H4NHCOCH3

172.23 179.21

6, 606 132, 244

e46

trans-2-Ethoxy-5(1-propenyl)phenol 3-Ethoxypropylamine 3-Ethoxysalicylaldehyde 2-Ethoxytetrahydrofuran Ethoxytrimethylsilane Ethyl acetate

C2H5OC6H3(CH ¨ CHCH3)OH C2H5OCH2CH2CH2NH2 C2H5OC6H3(OH)CHO

178.23

62, 918

103.17 166.18

43, 739 82, 267

0.861

C2H5O(C4H7O)

116.16

174, 1020

0.908

1.414020

(CH3)3SiOC2H5

118.3

0.757320 4

1.374220

0.900620 4

1.372420

Ethyl acetimidate HCl Ethyl acetoacetate (enol) Ethyl acetoacetate (keto) p-Ethylacetophenone Ethyl acrylate Ethylaluminum dichloride Ethylamine Ethyl 2-aminobenzoate

e47 e48 e49 e50 e51 e52 e53 e54 e55 e56 e57 e58 e59

CH3COOC2H5

86–88

84

Boiling point

Flash point 112

Solubility in 100 parts solvent i aq; v s alc, eth 0.076 aq; 6.7 alc; 7.1 chl; 1.1 eth; s glyc

136–138 263–264

32

170–172

16

77.1

3

9.7 aq; misc alc, acet, chl, eth

1.9 aq; misc alc, chl 12 aq; misc alc, chl

88.11

2, 125

CH3C( ¨ NH)OC2H5 · HCl

123.58

2, 182

CH3COCH ¨ C(OH)OC2H5

130.15

3, 632

1.011910

1.448010

44

180.8

84

CH3COCH2COOC2H5

130.15

3, 632

1.036810

1.422410

39

180.8

84

C2H5C6H4COCH3 CH2 ¨ CHCOOCH2CH3 CH3CH2AlCl2

148.21 100.12 126.95

74, 1101 2, 399

0.993 0.940520 4 1.20750

1.529320 1.406820

20.6 71.2 32

11411mm 99.5 11350mm

90 15

CH3CH2NH2 H2NC6H4COOCH2CH3

45.09 165.19

4, 87 14, 319

0.68915 15 1.08815

81.0 14

16.6 266–268

17

112–114

1.5 aq; s alc, eth

misc aq, alc, eth i aq; s alc, eth

e60

Ethyl 4-aminobenzoate

H2NC6H4COOCH2CH3

165.19

14, 422

e61

CH3C(NH2) ¨ CHCOOCH2CH3 CH3CH2NHCH2CH2OH

129.16

3, 654

1.02120 4

89.14

4, 282

0.91420 4

e63 e64 e65 e66 e67 e68

Ethyl 3-aminocrotonate 2-(Ethylamino)ethanol N-Ethylaniline 2-Ethylaniline 4-Ethylaniline 2-Ethylanthraquinone Ethylbenzene-d10 Ethylbenzene

C6H5NHCH2CH3 CH3CH2C6H4NH2 CH3CH2C6H4NH2

12, 159 122, 584 12, 1090 71, 425

C6D5CD2CD3 C6H5CH2CH3

121.18 121.18 121.18 236.27 116.25 106.17

e69

Ethyl benzoate

C6H5COOCH2CH3

e70

Ethyl benzoylacetate

e71

Ethyl 2-benzylacetoacetate N-Ethylbenzylamine Ethyl (2-benzyl)benzoylacetate

C6H5C( ¨ O)CH2COOCH2CH3 CH3COCH(CH2C6H5)COOC2H5 C6H5CH2NHC2H5 C6H5COCH(CH2C6H5)COOC2H5

e62

e72 e73

-Ethoxy--phenylacetophenone, b47 3-Ethoxy-1-propene, a90 Ethyl alcohols, e21, e22

88–90

310

33–35

210–215

1.440220

90

170

0.95825 25 0.98322 4 0.97522 4

1.555920 1.559020 1.554220

52, 274

0.867020 4

1.492020 1.495920

63 204.5 44 210 5 216 108–111 134.6 95.0 136.2

31 20

150.18

9, 110

1.05025 4

1.505220

34.7

212.4

84

192.21

10, 674

1.110

1.533820

265 d

140

220.27

10, 674

1.036

1.499620

276

112

135.21 282.34

12, 1020 10, 764

0.909 1.110

1.511720 1.556720

194 27080mm

66 112

Ethylaldehyde, a4 Ethyl anthranilate, e59 Ethyl benzenecarboxylate, e69

0.04 aq; 20 alc; 50 chl; 25 eth; s dil acid i aq; s alc, bz, eth 71

v s aq, alc, eth

85 97 85

i aq; misc alc, eth sl s aq; v s alc, eth sl s aq; v s alc, eth

0.01 aq; misc alc, bz, chl, eth 0.05 aq; misc alc, chl, bz, eth, PE i aq; misc alc, eth

Ethyl 3-benzenepropenoate, e103 -Ethylbenzyl alcohol, p142

1.239

1.240

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. e74

Name

e83 e84 e85 e86 e87 e88

Ethyl N-benzyl-Ncyclopropylcarbamate Ethyl bromoacetate Ethyl 2-bromobutyrate Ethyl 4-bromobutyrate Ethyl 2-bromoisobutyrate Ethyl 3-bromo-2-oxopropionate Ethyl 2-bromopentanoate Ethyl 2-bromopropionate Ethyl 3-bromopropionate 2-Ethyl-1-butanol 2-Ethyl-1-butene N-Ethylbutylamine 2-Ethylbutylamine 2-Ethylbutyraldehyde Ethyl butyrate

e89 e90

2-Ethylbutyric acid Ethyl butyrylacetate

e75 e76 e77 e78 e79 e80 e81 e82

Formula

Formula weight

Beilstein reference

Density

Refractive index

0.997

1.510420

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

112

C6H5CH2N(C3H5)COOCH2CH3

219.28

BrCH2COOCH2CH3 CH3CH2CH(Br)COOCH2CH3 BrCH2CH2CH2COOCH2CH3 (CH3)2C(Br)COOCH2CH3 BrCH2C( ¨ O)COOCH2CH3 CH3(CH2)2CH(Br)COOCH2CH3 CH3CH(Br)COOCH2CH3

167.01 195.06

2, 214 22, 255

1.50620 20 1.32920 20

1.451020 1.447020

159 177 d

47 58

195.06

2, 283

1.363

1.455920

8210mm

90

195.06

2, 296

1.32920 4

1.444620

6711mm

60

195.02

32, 409

1.554

1.469520

10010mm

98

209.09

2, 302

1.226

1.448620

190–192

77

181.03

2, 255

1.44720 20

1.447020

BrCH2CH2COOCH2CH3

181.03

2, 256

1.412318 4

1.456918

(C2H5)2CHCH2OH (C2H5)2C ¨ CH2 CH3(CH2)3NHCH2CH3 (C2H5)2CHCH2NH2 (C2H5)2CHCHO CH3CH2CH2COOCH2CH3

102.18 84.16 101.19 101.19 100.16 116.16

1, 412 13, 814 4, 157 4, 192 1, 693 2, 270

0.833020 0.669620 4 0.74020 4 0.77620 20 0.816220 20 0.87920 4

1.422420 1.396720 1.405020

114.4 131.5

1.401820 1.392820

89 98.0

(C2H5)2CHCOOH CH3(CH2)2C(O)CH2COOC2H5

116.16 158.20

2, 333 3, 684

0.922520 20 1.001

1.413320 1.429520

15

159–160 51

i aq; misc alc, eth i aq; misc alc, eth

i aq; misc alc, eth

i aq; misc alc, eth i aq; misc alc, eth

13650mm

79

i aq; misc alc, eth

146.5 64.7 108 121–125 116.7 121.6

58

0.63 aq

18 21 21 29

194.2 10422mm

99 78

s aq, alc, acet, eth 0.31 aq 0.49 aq; misc alc, eth 0.22 aq

e91

Ethyl carbamate

H2NCOOCH2CH3

e92 e93 e94 e95

Ethyl carbazate N-Ethylcarbazole Ethyl chloroacetate Ethyl 2-chloroacetoacetate Ethyl 4-chloroacetoacetate Ethyl 4-chlorobutyrate Ethyl chloroformate

H2NNHCOOCH2CH3

Ethyl 2-chloropropionate Ethyl 3-chloropropionate Ethyl chlorothioformate Ethyl chrysanthemumate

e96 e97 e98 e99 e100 e101 e102

89.09

3, 22

1.056

104.11 195.27 122.55 164.59

3, 98 20, 436 2, 197 3, 662

1.149820 4 1.190

1.422720 1.443020

164.59

3, 663

1.21817 4

150.61

2, 278

ClCOOC2H5

108.52

CH3CH(Cl)COOC2H5

ClCH2COOCH2CH3 CH3C( ¨ O)CH(Cl)COOC2H5 ClCH2C( ¨ O)CH2COOC2H5 ClCH2CH2CH2COOC2H5

49–50

182–184

44–47 66–68 26

11022mm

200 aq; 125 alc; 111 chl; 67 eth

144–146 10714mm

65 50

i aq; misc alc, eth i aq; s alc, eth

1.452020

11514mm

96

i aq; misc alc, eth

1.075420 4

1.430620

186

51

s alc, acet, eth

3, 10

1.140320 4

1.394120

95

2

136.58

2, 248

1.08620 4

1.418520

147–148

38

misc alc, bz, chl, eth i aq; misc alc, eth

ClCH2CH2COOC2H5

136.58

2, 250

1.108620 4

1.424920

163

54

misc alc, eth

ClC( ¨ O)SCH2CH3

124.59

3, 134

1.195

1.482020

132

30

196.29

92, 45

0.906

1.460020

11210mm

Ethyl benzyl ether, b95 Ethyl bromide, b277 Ethyl 2-bromo-2-methylpropanoate, e78 Ethyl bromopyruvate, e79

Ethyl bromovalerate, e80 Ethyl butyl ether, b449 Ethyl butyl ketone, h16 Ethyl caprate, e113

81

Ethyl caproate, e142 Ethyl caprylate, e190 Ethyl chloride, c102 Ethyl chloroglyoxylate, e191

1.241

1.242

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. e103 e104 e105 e106 e107 e108 e109 e110 e112 e112 e113 e114 e115 e116 e117 e118 e119

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

Ethyl transcinnamate Ethyl crotonate Ethyl cyanoacetate Ethyl cyanoformate Ethyl cyano(hydroxyimino)acetate Ethylcyclohexane cis-2-Ethylcyclohexanol 4-Ethylcyclohexanol Ethyl cyclohexylacetate Ethyl cyclopropanecarboxylate Ethyl decanoate Ethyl diazoacetate

C6H5CH ¨ CHCOOCH2CH3

176.22

92, 385

1.049520 4

1.559820

12

271.0

CH3CH ¨ CHCOOCH2CH3 NCCH2COOCH2CH3 NCCOOCH2CH3 NCC( ¨ NOH)COOCH2CH3

114.14 113.12 99.09 142.12

2, 411 2, 585 2, 547 3, 775

0.917520 4 1.056425 4 1.00320 4

1.424820 1.415620 1.382020

22.5

138 206.0 116

C6H11CH2CH3 CH3CH2C6H10OH

112.22 128.22

5, 35 62, 26

0.787920 0.92721 4

1.433020 1.464620

CH3CH2C6H10OH C6H11CH2COOCH2CH3

128.22 170.25

62, 26 9, 14

0.889 0.948

1.462520 1.443920

8410mm 212

77 80

C3H5COOCH2CH3

114.14

9, 4

0.960

1.419720

129–133

18

CH3(CH2)8COOCH2CH3 N2CH2COOCH2CH3

200.32 114.10

2, 356 31, 211

0.86220 1.085218 4

1.424820 1.458818

Ethyl 2,3-dibromopropionate Ethyl dichlorophosphate Ethyl dichlorothiophosphate N-Ethyldiethanolamine Ethyl diethoxyphosphinylformate

BrCH2CH(Br)COOCH2CH3 CH3CH2OP(O)Cl2

259.94

2, 259

1.78816 4

1.498620

245 102 misc alc, chl, eth 141720mm 26 misc alc, bz, eth explodes when heated 214 91 s alc, eth

162.94

1, 332

1.373

1.433820

6510mm

CH3CH2OP(S)Cl2

179.01

1, 333

1.353

1.504020

55–6810mm

CH3CH2N(CH2CH2OH)2

133.19

4, 284

1.014

1.466520

(C2H5O)2P(O)COOC2H5

210.17

32, 103

1.110

1.423020

misc alc, eth; i aq 2 110 24

i aq; s alc, eth i aq; misc alc, eth

130–132 111.3

22

50

131.8 18 74–7912mm 68

246–252 13513mm

123

i aq

e120

e128

Ethyl 3-(diethylamino)propionate Ethyl 3,3-dimethylacrylate Ethyl 2-dimethylaminobenzoate Ethyl 2,2-dimethylpropionate Ethylene carbonate EthylenediamineN,N,N,N-tetraacetic acid Ethylene dinitrate 2,2-(Ethylenedioxy)bisethanol Ethylene glycol

e129

Ethylene oxide

e121 e122 e123 e124 e125

e126 e127

(C2H5)2NCH2CH2COOC2H5 (CH3)2C ¨ CHCOOC2H5

173.26

4, 404

0.881

1.425320

8412mm

7

128.17

2, 433

0.924720 4

1.435020

155

33

(CH3)2NC6H4COOC2H5

193.25

1.061

1.542520

(CH3)3CCOOCH2CH3

130.19

22, 280

0.858418 4

1.392218

88.06 292.24

19, 100

1.320825

1.419940

36.4 245 d

238

160

misc aq 0.05 aq

1.49615 15 1.127415 4

1.49915 1.457815

22 72

10619mm 285

166

misc aq, alc, bz

1.113520 4

1.431920

13

197.6

110

0.89104

1.35977

112.44 10.6

misc aq, alc, acet, glc, HOAc, pyr; sl s eth; i bz, chl misc aq; s alc, eth

(HOOCCH2)2NCH2CH2N(CH2COOH)2 O2NOCH2CH2ONO2 HOCH2CH2OCH2CH2OCH2CH2OH HOCH2CH2OH

Ethyl 2-cyano-3-ethoxyacrylate, e132 N-Ethyldiisopropylamine, d418 Ethylene bromohydrin, b279 Ethylene chlorohydrin, c103 Ethylene cyanohydrin, h169 Ethylene diacetate, e17

152.07 150.17 62.07

44.05

1, 465

Ethylenediamine, e15 Ethylene dibromide, d78 Ethylene dichloride, d177 (Ethylenedinitrilo)tetraacetic acid, e125 2,2-Ethylenedioxybis (ethanol), t270 Ethylene glycol, e16

98 118.2

s alc, eth

18

Ethylene glycol p-butylphenyl ethers, b475, b476 Ethylene glycol diacetate, e17 Ethylene glycol diethyl ether, d252 Ethylene glycol dimethyl ether, d439 Ethylene glycol dinitrate, e126

1.243

1.244

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

e130

Ethylene sulfide

60.12

e131

Ethylenimine

43.07

e132

Ethyl (ethoxymethylene)cyanoacetate Ethyl fluoroacetate Ethyl fluorosulfonate Ethyl formate

e133 e134 e135 e136 e137 e138 e139 e140 e141 e142 e143 e144 e145 e146

Ethyl 2-furoate Ethyl heptafluorobutyrate Ethyl heptanoate Ethyl hexadecanoate 3-Ethylhexane 2-Ethyl-1,3hexanediol Ethyl hexanoate 2-Ethylhexanoic acid 2-Ethyl-1-hexanol 2-Ethylhexanoyl chloride 2-Ethylhexyl acetate

C2H5OCH ¨ C(CN)COOC2H5 FCH2COOC2H5 FSO2OC2H5 HCOOC2H5

CF3CF2CF2COOC2H5 CH3(CH2)5COOC2H5 CH3(CH2)14COOC2H5 CH3CH2CH2CH(C2H5)2 C3H7CH(OH)CH(C2H5)CH2OH CH3(CH2)4COOC2H5 CH3(CH2)3CH(C2H5)COOH CH3(CH2)3CH(C2H5)CH2OH CH3(CH2)3CH(C2H5)COCl CH3(CH2)3CH(C2H5)CH2OOCCH3

Beilstein reference

Density

Refractive index

172, 12

1.010

1.493520

0.832125 4

1.412325

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

55–56

10

sl s alc, eth

78.0

56

24

misc aq; sl s alc

51–53

19030mm 30 32

s aq

79.4

119753mm 23– 2512mm 54.2

28

33–36

196 94–96

70

12 aq; misc alc, eth i aq; s alc, eth

129

s alc, eth s alc, eth sl s alc; s eth 0.6 aq; s alc

169.18

3, 470

106.10 128.12

2, 193

1.092621

1.375520

74.08

2, 19

0.91720 4

1.359920

140.14 242.09

18, 275

1.11720 4 1.39420

1.303020

158.24 284.48 114.24 146.23

22, 295 22, 336 13, 478

0.868520 4 0.857725 4 0.713620 4 0.932522 4

1.414415 1.434734 1.401620 1.453022

66 22 40

187 19110mm 118.5 244.2

144.21 144.21

2, 323 2, 349

0.87120 4 0.907720 20

1.407520 1.424120

67 118.4

166–168 227.6

49 127

i aq; misc alc, eth 0.25 aq

0.934420 20

1.423120

76

184.3

77

0.07 aq; s alc, bz, chl

0.939

1.433520

6811mm

69

0.871820 20

1.420420

198.6

82

130.23 162.66 172.27

22, 304

93

0.03 aq; misc alc

e147

2-Ethylhexylamine

e148

2-Ethylhexyl vinyl ether Ethyl hydrogen hexanedioate Ethyl hydroxyacetate Ethyl 4-hydroxybenzoate Ethyl 3-hydroxybutyrate Ethyl 2-hydroxyethyl sulfide Ethyl 2-hydroxyisobutyrate Ethyl 4-hydroxy-3methoxyphenylacetate

e149 e150 e151 e152 e153 e154 e155

129.31

0.79220 20

156.26

0.810220 20

CH3(CH2)3CH(C2H5)CH2NH2 CH3(CH2)3CH(C2H5)CH2OCH ¨ CH2 HOOC(CH2)4COOC2H5

174.20

21, 277

HOCH2COOC2H5 HOC6H4COOC2H5

104.11 166.18

3, 236 10, 159

1.08715 4

CH3CH(OH)CH2COOC2H5

132.16

3, 309

1.01720 4

1.420520

170

HOCH2CH2SCH2CH3

106.19

12, 525

1.02020 20

1.486920

184.5

(CH3)2C(OH)COOC2H5

132.16

3, 315

0.965

1.407820

150

HOC6H3(OCH3)CH2COOC2H5

210.23

101, 198

Ethylene glycol monoacetate, h116 Ethylene glycol monobutyl ether, b410 Ethylene glycol monoethyl ether, e34 Ethylene glycol monomethyl ether, m65 Ethylene glycol monomethyl ether acetate, m68 Ethylene iodide, d403 Ethylene iodohydrin, i35

165–169 1.427320 1.438720

100 glass 28–29

177.7 18018mm

44–47

i aq; s alc, acet, eth 0.01 aq

112

160 297 d

116

1,8-Ethylenenaphthalene, a2 Ethylenethiourea, i5 Ethylene trichloride, t227 Ethyleneurea, i7 N-Ethylethanamine, d267 Ethyl N-ethylcarbamate, e231 Ethylethylene oxide, e3

57

v s alc, eth 0.07 aq; v s alc, eth 64

s aq, alc s eth

44

d hot aq

180– 18514mm

Ethyl fluroide, f17 2-Ethylhexyl alcohol, e144 Ethyl homovanillate, e155 N-Ethyl-N-(2-hydroxyethyl)-3-toluidine, e225 Ethyl 2-hydroxy-2-methylpropanoate, e154

1.245

1.246

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. e156

e157 e158 e159 e160 e161 e162 e163 e164 e165 e166 e167 e168 e169 e170 e171

Name 2-Ethyl-2-(hydroxymethyl)-1,3propanediol N-Ethyl-3-hydroxypiperidine 5-Ethylidene-2norbornene 2-Ethylimidazole 2-Ethyl-6-isopropylaniline Ethyl isothiocyanate Ethyl L-()-lactate Ethyl DL-mandelate Ethyl 2-mercaptoacetate Ethylmercury chloride Ethyl methacrylate Ethyl 4-methoxyphenylacetate Ethyl 2-methylacetoacetate N-Ethyl-N-methylaniline Ethyl 3-methylbutyrate Ethyl methyl ether

Formula CH3CH2C(CH2OH)3

(CH3)2CHC6H3(C2H5)NH2 CH3CH2NCS CH3CH(OH)COOC2H5

Formula weight

Beilstein reference

134.18

13, 2349

Density

Refractive index

Melting point 60–62

129.20

0.970

1.475420

120.20

0.893

1.4895

96.13 163.26

0.949

Boiling point

Flash point

Solubility in 100 parts solvent

159– 1612mm 93– 9515mm

47 38

79–81 249 6 26

130–132 154.5

32 70

i aq; misc alc, eth misc aq, alc, eth, esters, PE

37

253–255 5412mm

47

s alc, eth

87.14 118.13

4, 123 3, 264

1.00318 4 1.032820

1.514218 1.412420

C6H5CH(OH)COOC2H5 HSCH2COOC2H5

180.21 120.17

10, 202 3, 255

1.096415

1.457120

CH3CH2HgCl

165.13

H2C ¨ C(CH3)COOC2H5 CH3OC6H4CH2COOC2H5

114.14 194.23

2, 423 101, 83

0.90925 15 1.097

1.411625 1.507520

118 1387mm

49 46

i aq; s alc, eth

CH3C( ¨ O)CH(CH3)COOC2H5 C6H5N(CH3)C2H5

144.17

3, 679

1.01920 4

1.418220

187

62

i aq; s alc, eth

135.21

12, 162

0.919355 4

1.547420

203–205

(CH3)2CHCH2COOC2H5

130.19

22, 275

0.86820 20

1.396220

60.09

1, 314

0.72500

CH3CH2OCH3

3.5

192

99.3

subl

134.7 10.8

0.78 eth; 2.6 chl

i aq; misc alc, eth 26

0.2 aq; misc alc, bz s aq; misc alc, eth

e172 e173

e174 e175 e176 e177

2-Ethyl-4-methylimidazole Ethyl 4-methyl-5imidazolecarboxylate 3-Ethyl-2-methylpentane 3-Ethyl-3-methylpentane Ethyl 3-methyl-3phenylglycidate Ethyl 1-methyl-2piperidinecarboxylate

Ethyl 2-hydroxypropionate, e162 Ethylidene bromide, d77 Ethylidene chloride, d176 Ethylidene dimethyl ether, d438 Ethylidene fluoride, d346 2,2-Ethyliminodiethanol, e118 Ethyl iodide, i34

110.16

232, 72

154.17

251, 534

(C2H5)2CHCH(CH3)2

114.24

13, 489

(C2H5)3CCH3

0.975

1.499520

292–295

137

204–206 0.719320 4

1.404020

115.0

115.7

i aq; sl s alc; s eth

114.24

0.727420 4

1.407820

90.9

118.3

i aq; s eth

206.24

1.0915 4

1.50820

0.975

1.451920

171.24

221, 485

Ethyl isonicotinate, e216 Ethyl isonipecotate, e206 Ethyl isopropylacetate, e170 Ethyl isothiocyanatoformate, e32 Ethyl isovalerate, e170 Ethyl levulinate, e195 Ethyl linoleate, e188

92– 9611mm

73

Ethyl mercaptan, e20 Ethyl 3-methylcrotonate, e121 Ethyl methyl ketone, b393 Ethyl 1-methylnipecotate, e177 Ethyl 2-methyl-4-oxo-2-cyclohexene-1carboxylate, c9 Ethyl 1-methylpipecolinate, e178

1.247

1.248

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. e178

e179 e180 e181 e182 e183 e184 e185 e186 e187 e188

e189 e190 e191 e192 e193

Name Ethyl 1-methyl-3piperidinecarboxylate 2-Ethyl-2-methyl1,3-propanediol 3-Ethyl-4-methylpyridine 5-Ethyl-2-methylpyridine Ethyl methyl sulfide Ethyl (methylthio)acetate N-Ethylmorpholine Ethyl nitrate Ethyl nitrite 4-Ethylnitrobenzene Ethyl (Z,Z)-9,12octadecadienoic acid Ethyl cis-9-octadecenoate Ethyl octanoate Ethyl oxalyl chloride Ethyl oxamate 2-Ethyl-2-oxazoline

Formula

Formula weight

Beilstein reference

171.24

Density

Refractive index

0.954

1.451020

Melting point

Boiling point

118.18

1, 487

121.18

202, 163

0.928617 4

C2H5(CH3)C5H3N

121.18

20, 248

0.918423 4

1.497420

76.15

1, 343

0.842220

1.440320

1.043

1.458720

271, 203 1, 329

0.91620 20 1.10025 4

1.441020 1.384922

63 94.6

139 87.7

CH3CH2ONO 75.07 C2H5C6H4NO2 151.17 H(CH2)5CH ¨ CHCH2308.51 CH ¨ CH(CH2)7COOC2H5

1, 329 5, 358 22, 461

0.9015 15 1.118 0.884616 4

1.544520 1.467520

32

17 245–246 1936mm

CH3(CH2)7CH ¨ CH(CH2)7COOC2H5 CH3(CH2)6COOC2H5 CH3CH2OC( ¨ O)COCl

310.52

2, 467

0.86920 4

1.44525

 15

21615mm

172.27 136.53

2, 348 2, 541

0.87817 1.222320 4

1.416620 1.416420

47

206–208 135

117.10 99.13

2, 544 0.982

1.437020

CH3SCH2COOC2H5

134.20

CH3CH2ONO2

115.18 91.13

CH3CH2OC( ¨ O)CONH2

Solubility in 100 parts solvent

8911mm

HOCH2C(C2H5)(CH3)CH2OH C2H5(CH3)C5H3N

CH3CH2SCH3

Flash point

41–44

226 198

105.9

s alc, eth; sl s aq

178

66

s alc, bz, eth, acid

66.7

49

i aq; misc alc, eth

59

114–116 62 128.4

27 flammable  112  112

misc aq, alc, eth 1 aq; misc alc, eth misc alc, eth v s alc, eth misc DMF, oils

i aq; misc alc, eth 75 41

i aq; misc alc, eth d aq, alc; s bz, eth s aq, eth; i bz

29

e194

e195 e196 e197 e198 e199 e200 e201 e202 e203 e204 e205

1.448520

10211mm

3, 675

1.01220 20

1.422220

205–206

116.12

3, 616

1.06016 4

1.40816

144

(C2H5)3CH CH3(CH2)3COOC2H5

100.20 130.19

13, 441 2, 301

0.698220 4 0.87720 4

1.393420 1.373220

118.6 91.3

93.5 145.5

CH3CH2C6H4OH C6H5CH2COOC2H5

122.17 164.20 158.20

6, 472 9, 434 232, 9

1.01125 4 1.033320 4 1.080

1.5239 1.498020 1.476520

47.0

218–219 226 273

77 112

113.20 113.20 157.21

20, 17 20, 104 22, 7

0.823720 4 0.850 1.006

1.444020 1.451020 1.456220

131 143 216–217

18 31 46

1.012

1.460120

1047mm

90

(O ¨ )C5H7COOC2H5

156.18

CH3C( ¨ O)CH2CH2COOC2H5 CH3C( ¨ O)COOC2H5

144.17

4-Ethylphenol Ethyl phenylacetate Ethyl N-piperazinocarboxylate 1-Ethylpiperidine 2-Ethylpiperidine Ethyl 2-piperidinecarboxylate Ethyl 3-piperidinecarboxylate

Ethyl nicotinate, e215 Ethyl nipecotate, e205 Ethyl oleate, e189

112

1.054

Ethyl 2-oxocyclopentanecarboxylate Ethyl 4-oxopentanoate Ethyl 2-oxopropionate 3-Ethylpentane Ethyl pentanoate

157.21

Ethyl pentyl ketone, o35 Ethyl phenyl ether, e28 Ethyl picolinate, e214

v s aq; misc alc 45

Ethyl pipecolinate, e204 Ethylpiperidinol, e157

sl s aq; misc alc, eth i aq; s alc, eth 0.2 aq; misc alc, eth i aq; misc alc, eth i aq; misc alc, eth

s aq

1.249

1.250

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. e206

Name Ethyl 4-piperidinecarboxylate Ethyl N-piperidinepropionate Ethyl propionate Ethyl propyl ether

Formula

Formula weight

Beilstein reference

157.21

Density

Refractive index

Melting point

Boiling point

Flash point

1.010

1.459120

204

80

217–219

87

185.27

20, 62

0.927

1.454520

CH3CH2COOC2H5 CH3CH2OCH2CH2CH3

102.13 88.15

2, 240 1, 354

0.89120 4 0.73920 4

1.383920 1.369520

73.9 79

99.1 62–63

12 32

CH3CH2SCH2CH2CH3 CH3CH2C5H4N CH3CH2C5H4N CH3CH2C5H4N

104.21 107.16 107.16 107.16 151.17

13, 1432 20, 241 20, 242 20, 243 22, 35

0.827020 4 0.937 0.954 0.940422 4 1.119420

1.446220 1.496420 1.501520 1.500920 1.508820

117.0

2

118.5 149 162–165 168 240–241

29 48 47 107

151.17

22, 39

1.107020

1.504020

8–9

23–224

93

151.17

222, 37

1.00915 4

1.500920

23

220

87

0.992

1.465220

9720mm

76

e218

Ethyl propyl sulfide 2-Ethylpyridine 3-Ethylpyridine 4-Ethylpyridine Ethyl 2-pyridinecarboxylate Ethyl 3-pyridinecarboxylate Ethyl 4-pyridinecarboxylate 1-Ethyl-2-pyrrolidinone Ethyl salicylate

C6H4(OH)COOC2H5

166.18

10, 73

1.13120 4

1.521920

231–234

107

e219

Ethyl sorbate

140.18

2, 484

0.959

1.494220

195.5

69

e220 e221

S-Ethyl thioacetate 3-Ethylthio-1,2propanediol Ethyl 4-toluenesulfonate N-Ethyl-m-toluidine

CH3CH ¨ CHCH ¨ CHCOOC2H5 CH3C( ¨ O)SCH2CH3 C2H5SCH2CH(OH)CH2OH

104.16 136.21

2, 232

0.97628 4 1.095

1.450328 1.506520

116–117

CH3C6H4SO2OC2H5

200.26

11, 99

1.16645 4

1.511020

CH3C6H4NHC2H5

135.21

12, 857

0.957

1.545120

e207 e208 e209 e210 e211 e212 e213 e214 e215 e216 e217

e222 e223

113.16

2–3

Solubility in 100 parts solvent s aq, alc, bz, eth

2 aq; misc alc, eth sl s aq; misc alc, eth s alc sl s aq; s alc, eth v s alc, eth; sl s aq sl s aq; s alc, eth misc aq, alc, eth v s aq, alc, eth; s bz i aq; s alc, bz, chl

misc alc, eth; sl s aq

i aq; v s alc, eth 112

33

17315mm

157

221

89

i aq; s alc, eth

e224 e225 e226 e227 e228 e229 e230 e231 e232 e233 e234

6-Ethyl-o-toluidine 2-(N-Ethyl-mtoluidino)ethanol Ethyl trichloroacetate Ethyl trifluoroacetate Ethyl (trimethylsilyl)acetate Ethyl undecanoate Ethylurea N-Ethylurethane Ethyl vinyl ether N-Ethyl-2,3xylidine 1-Ethynyl-1-cyclohexanol

Ethyl pivalate, e123 1-Ethyl-1-propanol, p39 Ethyl propenoate, e56 1-Ethylpropylamine, a252

O HN O

CH3CH2C6H3(CH3)NH2 CH3C6H4N(C2H5)CH2CH2OH Cl3CCOOC2H5

135.21 179.26 191.44

F3CCOOC2H5

142.08

(CH3)3SiCH2COOC2H5

160.29

CH3(CH2)9COOC2H5 CH3CH2NHC( ¨ O)NH2 CH3CH2NHCOOC2H5 CH3CH2OCH ¨ CH2 (CH3)2C6H3NHC2H5

214.35 88.11 117.15 72.11 149.24

C6H10(C ˜ CH)OH

124.18

0.968 1.019

1.552520 1.554020

2, 209

1.38320 4

22, 186

33

231 1151mm

89

1.444720

168

65

1.194

1.306820

60–62

1

0.876

1.415320

156–159

35

2, 358 4, 115 4, 114 1, 433 12, 1101

0.859 1.21318 0.98120 4 0.753120 0.917

1.428020

1054mm

112

115.8

8520mm 35.7 227–228

75 17 71

62, 100

0.96720 20

30–31

180

62

Ethyl pyruvate, e196 2-(Ethylthio)ethanol, e153 Ethyl thioglycolate, e164 Ethyltriethoxysilane, t261

93–96 1.421120 1.375420 1.546820

Ethyl trimethylacetate, e123 Ethyl vanillin, e39 Ethyne, a41 Ethynylbenzene, p82

i aq; s alc, eth

i aq; s org solv v s aq; 80 alc; i eth 63 aq 0.9 aq

2.4 aq; misc alc, bz, acet, ketones, PE

1.251

1.252

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. e235

Name

f1 f2

1-Ethynylcyclohexylamine Fluoranthene Fluorene

f3 f4

9-Fluorenone Fluorescein

f5 f6 f7 f8

Fluoroacetamide Fluoroacetic acid Fluoroacetone p-Fluoroacetophenone p-Fluoroaniline o-Fluorobenzaldehyde Fluorobenzene o-Fluorobenzoic acid p-Fluorobenzoic acid p-Fluorobenzoyl chloride o-Fluorobenzyl alcohol p-Fluorobenzyl chloride Fluoroethane

f9 f10 f11 f12 f13 f14 f15 f16 f17

Formula C6H10(C ˜ CH)NH2

Formula weight

Beilstein reference

123.30

Density

Refractive index

0.913

1.481720

202.26 166.22

5, 685 5, 625

1.25204 1.20304

180.21 332.31

7, 465 19, 222

1.130099 4

FCH2C(O)NH2 FCH2COOH CH3C(O)CH2F FC6H4COCH3

77.06 78.04 76.07 138.14

2, 193 2, 193

FC6H4NH2 FC6H4CHO

111.12 124.11

C6H5F FC6H4COOH

Melting point

Boiling point 6620mm

1.636999

82–85 314 d

107 subl 33

165 75 196

7 71

187 9146mm

73 55

sl s aq; s alc, eth

12

0.15 aq; misc alc sl s aq; s alc, eth

12, 597 71, 132

1.172520 4 1.178

1.539520 1.522020

1.9 44.5

96.11 140.11

5, 198 9, 333

1.024020 4 1.46025 4

1.465720

42.2 84.7 123–125

FC6H4COOH FC6H4COCl

140.11 158.56

9, 333 91, 137

1.47925 4 1.342

1.529620

FC6H4CH2OH

126.13

61, 222

1.173

1.513620

FC6H4CH2Cl

144.58

1.207

1.513020

48.06

1, 82

0.002200

sl s alc; s bz, eth v s HOAc; s bz, eth s alc, bz; v s eth s hot alc, hot HOAc, alk; i bz, chl, eth v s aq; s acet sl s aq, alc

342

1.3700 1.511020

182.6 9

Solubility in 100 parts solvent

42

107–110 384 114.8 295

1.054 1.138

CH3CH2F

Flash point

0.1 aq; s alc, eth 8220mm

82 90

8226mm 143.2

37.7

60 198 mL aq; v s alc, eth

f18

Fluoromethane

CH3F

f19

4-Fluoro-1-methoxybenzene 2-Fluoro-2-methylpropane 1-Fluoro-4-nitrobenzene 4-Fluorophenol 2-Fluoropyridine o-Fluorotoluene m-Fluorotoluene p-Fluorotoluene Formaldehyde Formamide Formamidine acetate Formamidinesulfinic acid

FC6H4OCH3

f20 f21 f22 f23 f24 f25 f26 f27 f28 f29 f30

Eugenol, m99 Fenchone, t351 Fenchyl alcohol, t350

34.04

1, 59

1.1951 g·L 1.114

126.13

61, 98

(CH3)3CF

76.11

14, 286

FC6H4NO2

141.10

5, 241

1.330020 4

1.531220

FC6H4OH FC5H4N FC6H4CH3 FC6H4CH3 FC6H4CH3 H2C ¨ O HC( ¨ O)NH2 HC( ¨ NH)NH2 · HOOCCH3 H2NC( ¨ NH)S(O)OH

112.10 97.09 110.13 110.13 110.13 30.03 45.04 104.11 108.12

6, 183 201, 80 5, 290 5, 290 5, 290 1, 558 2, 26

1.128 1.001417 0.997420 0.997520 0.81520 4 1.133420 4

1.468020 1.471617 1.469120 1.468820 0.815320 1.447520

31, 36

Ferulic acid, h136 2,7-Fluorenediamine, d38 N-9H-2-(2-Fluorenyl)acetamide, a13

1.487720

141.8

78.4

45

157

43

77

12.1

12

21

205

83

46–48

185 126 114.4 116.5 116.6 19.5 11120mm

68 28 12 9 40

62.0 87.7 56.7 92 2.6 158 d 126 d

154

Fluorotrichloromethane, t232 Fluothane, b258 Formic acid hydrazide, f34

166 mL aq; v s alc, eth s eth

i aq; s alc, eth

v s alc, eth s alc, eth s alc, eth 122 aq; s alc, eth misc aq, alc, acet

1.253

1.254

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula C6H5NHCHO HCOOH C6H4(HCO)COOH HC( ¨ O)NHNH2

Formula weight

Beilstein reference

121.14 46.03 150.13 60.06

12, 230 2, 8 10, 666 2, 93

1.144 1.22020 4 1.404

1.371420

113.16 180.16

20, 45 31, 321

1.019

1.478020

Density

Refractive index

f31 f32 f33 f34

Formanilide Formic acid 2-Formylbenzoic acid Formylhydrazine

f35 f36

N-Formylpiperidine D-()-Fructose

f37

Fumaric acid

HOOCCH ¨ CHCOOH

116.07

2, 737

1.63520 4

f38

Fumaroyl dichloride

ClC( ¨ O)CH ¨ CHC( ¨ O)Cl

152.96

2, 743

1.40820

1.498820

f39 f40 f41

2-Furaldehyde Furan 2-Furanacrylic acid

96.09 68.07 138.12

172, 305 17, 27 18, 300

1.159820 4 0.937120 4

1.526220 1.421420

f42

112.08

18, 272

f43 f44 f45 f46 f47 f48 g1

2-Furancarboxylic acid 2,5-Furandimethanol 2-Furanmethanethiol Furfuryl acetate Furfuryl alcohol Furfurylamine 2-Furoyl chloride D-()-Galactose

128.13 114.17 140.14 98.10 97.12 130.53 180.16

171, 90 172, 116 172, 115 17, 112 18, 584 18, 276 31, 295

1.132 1.117520 4 1.128520 4 1.099520 4 1.324

1.530420 1.461820 1.486820 1.490020 1.531020

g2

Geraniol

154.25

1, 457

0.889420 4

1.476020

g3

-D-Glucoheptonic acid -lactone

(CH3)2C ¨ CHCH2CH2C(CH3) ¨ CHCH2OH

208.17

Melting point 47 8.5 98 54–56

287

36.5 85.6 141

Boiling point

Flash point

271 100.8

68

222

91

subl 200 161–164

73

161.8 31.4 286

68 35

133–134 230–232

Solubility in 100 parts solvent 2.5 aq misc aq, alc, eth s aq; v s alc, eth v s alc, chl, eth; s bz v s aq; 6.7 alc; s pyr 0.6 aq; 9 alc; 0.7 eth d aq, alc 8 aq; misc alc, eth 1 aq; misc alc, eth 0.2 aq; 1.1 bz; s alc, eth, HOAc 4 aq; s alc; v s eth

74–76 14.6 70 2 167

145–148

155 175–177 170.0 145–146 170

45 65 65 45 85

230

76

i aq; s alc, eth misc aq(d); v s alc misc aq; s alc, eth d aq, alc; s eth 200 aq; s pyr; sl s alc i aq; misc alc, eth s aq

Formylamide, f28 Formylphenols, h94, h95, h96 1-Formylpiperazine, p180 Formylpyridines, p251, p256, p253 Freon-11, t232 Freon-12, d170 Freon-12B2, d75 Freon-21, d183 Freon-22, c85

Freon-114, d227 2,5-Furandione, m2 2-Furanmethanol, f46 Furfural, f39 2-Furfuraldehyde, f39 Furfuryl mercaptan, f44 Furoic acid, f42 Furylacrylic acid, f41 2-Furyl methyl ketone, a44

Galactaric acid, t84 Galactitol, d738 Gallic acid, t306 Gallusic acid, t306 Gentisic acid, d384 Geranial, d562 D-Glucitol, s5

1.255

1.256

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

g4 g5 g6

D-Gluconic acid

g7

g9 g10

-D-Glucose pentaacetate D-Glucurono-3,6lactone L-Glutamic acid L-Glutamine

g11

Glutaric acid

g12 g13 g14 g15

Glutaric anhydride Glutaric dialdehyde Glutaronitrile Glutaryl dichloride

g16

Glycerol

g17

Glyceryl 1,2diacetate Glyceryl 1,3diacetate Glyceryl tris(butyrate) Glyceryl tris(dodecanoate)

g8

g18 g19 g20

Formula

D-Glucosamine

-D-()-Glucose

Formula weight

Beilstein reference

196.16 179.17 180.16

3, 542 1, 902 31, 83

390.34

31, 119

Density

Refractive index

OCHCH2CH2CH2CHO NCCH2CH2CH2CN ClC( ¨ O)CH2CH2CH2C( ¨ O)Cl HOCH2CH(OH)CH2OH HOCH2CH(OOCCH3)CH2OOCCH3 CH3COOCH2CH(OH)CH2OOCCH3

Boiling point

Flash point

131 88() 146

1.562018 4

176–178

147.13 146.15

4, 488 4, 491

1.53820 4

132.12

2, 631

1.42920 4

1.4188106

114.10 100.12 94.12 169.01

17, 411 1, 776 2, 635 2, 634

0.988823 1.324

1.373020 1.434520 1.472020

92.09

1, 502

1.261320

176.17

2, 147

176.17

Solubility in 100 parts solvent v s aq; sl s alc; i eth v s aq; i chl, eth 91 aq; 0.83 MeOH; s pyr 0.15 aq; 1.3 alc; 3 eth 27 aq; 2.8 MeOH

109–111

176.12

HOOCCH2CH2CH2COOH

Melting point

d 247 d 185

subl 200

0.8 aq; i alc, eth 4 aq; 0.0035 MeOH; i bz, chl, eth, acet 64 aq; v s alc, eth; s bz, chl; sl s PE

97.5

20020mm

52–55 6 29

15010mm 187–189 d 286 112 216–218 106

1.474620

18.18

18220mm

1.18416 4

1.117315

40

17240mm

misc aq, alc; 0.2 eth s aq, alc, bz, eth

2, 290

1.17915

1.439520

42

17240mm

s aq, alc, bz, chl

302.37

2, 273

1.03220 4

1.435920

75

305–310

639.02

2, 363

0.89460 4

1.440460

46

173

misc aq, alc s aq, alc, chl; i eth d aq, alc; s eth

i aq; v s alc, eth v s bz, eth; sl s alc

g21 g22 g23 g24

Glyceryl tris(nitrate) Glyceryl tris(oleate) Glyceryl tris(palmitate) Glyceryl tris(tetradecanoate)

Glutaraldehyde, g13 Glyceraldehyde, d398 Glycerol dichlorohydrin, d220

O2NOCH2CH(ONO2)CH2ONO2

227.09

1, 516

1.59420 4

1.478612

13.3

1605mm

885.46

4, 468

0.91515 4

1.462140

23515mm

807.35

2, 373

0.866380 4

1.438180

4 to 5 65–66

0.18 aq; 54 alc; misc eth s chl, eth, CCl4

310–320

v s bz, chl, eth

723.18

2, 367

0.88560 4

1.442860

57

Glycerol -monochlorohydrin, c212 Glyceryl triacetate, p201 Glyceryl tris(laurate), g20

expl 270

Glyceryl tris(myristate), g24

v s alc, bz, chl

1.257

1.258

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

75.07

4, 333

1.1607

g25

Glycine

H2NCH2COOH

g26

N-Glycylglycine

132.12

4, 371

g27

Glyoxal

H2NCH2C( ¨ O)NHCH2COOH HC( ¨ O)CHO

58.04

1, 759

g28 g29 h1 h2

HC( ¨ O)COOH H2NC( ¨ NH)NH2 CH3(CH2)15CH3 CF3CF2CF2COOH

74.04 59.07 140.41 214.04

3, 594 3, 82 1, 173

CF3CCl2CF(Cl)CF3

h5

Glyoxylic acid Guanidine Heptadecane Heptafluorobutyric acid Heptafluoro-2,3,3trichlorobutane 2,2,4,4,6,8,8-Heptamethylnonane Heptanal

h6 h7 h8 h9 h10 h11 h12 h13

Heptane 1,7-Heptanediamine Heptanedioic acid 1-Heptanethiol Heptanoic acid Heptanoic anhydride 1-Heptanol 2-Heptanol

h3 h4

Refractive index

Melting point

Boiling point

Flash point

d 233

25 aq; 0.6 pyr; i eth s hot aq; sl s alc

d 262 1.2920 4

1.382620

15

0.776722 1.645

1.436025

98 60 22.0

287.5

1.748420

1.353020

4

(CH3)3CCH2C(CH3)2CH2CH(CH3)CH2C(CH3)3 CH3(CH2)5CHO

226.45

0.793

1.439120

114.19

12, 750

0.821615 4

1.428520

43

153

35

CH3(CH2)5CH3 H2N(CH2)7NH2 HOOC(CH2)5COOH CH3(CH2)6SH CH3(CH2)5COOH [CH3(CH2)5CO]2O CH3(CH2)6OH CH3(CH2)4CH(OH)CH3

100.21 130.24 160.17 132.27 130.19 242.36 116.20 116.20

1, 154 4, 271 2, 670 1, 415 2, 338 2, 340 1, 414 1, 415

0.683820 4

1.387720

90.6 27–29 105.8 43.2 7.5 12.4 34.6

98.4 147–149 21210mm 176.9 223.0 268 175.8 160

1 87

1.32915 0.918120 4 0.93220 4 0.821920 4 0.819320 4

1.422120 1.433220 1.424220 1.421020

Solubility in 100 parts solvent

51

d 160 302.2 120

148

violent reaction aq; s anhyd solv; mixtures with air may explode v s aq; sl s alc, eth v s aq, alc s eth; sl s alc

98 240

46 112 112 73 41

misc alc, eth; sl s aq s alc, chl, eth 5 aq; v s alc, eth i aq 0.25 aq; s alc, eth i aq; s alc, eth misc alc, eth 0.35 aq; s alc, bz, eth

h14

3-Heptanol

h15 h16

2-Heptanone 3-Heptanone

h17

4-Heptanone

h18 h19 h20 h21 h22 h23 h24 h25

Heptanoyl chloride 1-Heptene 1-Heptylamine Heptyltrichlorosilane 1-Heptyne Hexachloroacetone Hexachlorobenzene Hexachloro-1,3butadiene 1,2,3,4,5,6-Hexachlorocyclohexane Hexachlorocyclo-1,3pentadiene

h26 h27

CH3(CH2)3CH(OH)CH2CH3 CH3(CH2)4COCH3 CH3(CH2)3C( ¨ O)CH2CH3 CH3CH2CH2(O)CH2CH2CH3 CH3(CH2)5COCl CH3(CH2)4CH ¨ CH2 CH3(CH2)6NH2 CH3(CH2)6SiCl3 CH3(CH2)4C ˜ CH Cl3CC( ¨ O)CCl3 C6Cl6 Cl2C ¨ CClCCl ¨ CCl2 C6H6Cl6

Glycidol, e11 Glycidyl methacrylate, e12 Glycinonitrile, a106 Glycolaldehyde, h86 Glycolaldehyde diethyl acetal, d253 Glycolic acid, h87 Glycol methacrylate, h121

116.20

11, 205

0.818

1.421420

114.19 114.19

1, 699 1, 699

0.819715 4 0.819720 20

1.411615 1.408520

114.19

1, 699

0.82115 4

1.406820

148.63 98.90 115.22 233.7 96.17 264.75 284.78 260.76

2, 340 1, 219 4, 193 1, 256 1, 657 5, 205 1, 250

0.96020 0.697020 0.777 1.08720 4 0.733 1.743 2.04424 1.655

1.430020 1.399920 1.424320 1.443925 1.407520 1.511220

290.83

52, 11

1.8720

272.77

Glyoxaline, 14 Guaiacol, m87 Heliotropin, m239 Heliotropyl alcohol, m242 Hemimellitene, t333 Hemimellitic acid, b28 Heptaldehyde, h5

1.70125 4

1.555020

6620mm

54

sl s aq

35 36.7

151 147.8

47 41

s alc, eth 0.43 aq; s alc, eth

32.1

143.7

48

173 93.6 154–156 211–212 99–100 666mm 323–326 210–220

57 1 35

0.53 aq; misc alc, eth d aq, alc; s eth 0.1 aq; s alc, eth s alc, acet, eth, PE

118.9 23 81 30 231 19

22 none none

113 1.564420

10

sl s aq; s acet s bz, chl, eth s alc, eth s bz, chl

239

none

sec-Heptyl alcohol, h13 Heptyl bromide, b291 Heptyl chloride, c128 Heptyl iodide, i37 Heptyl mercaptan, h9 Hexachloro-2-propanone, h23

1.259

1.260

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. h28 h29 h30

Formula weight

Beilstein reference

Density

Cl3SiOSiCl3 Cl3CCCl3

284.9 236.74 370.83

1, 87

2.09120 4

248.75 226.45 258.45

1, 200 1, 172 13, 2244

1.765 0.773320 4

1.548020 1.434520

258.51 256.43 242.45 224.43 241.46

1, 430 2, 370 1, 429 1, 226 4, 202

0.840 0.85262 4 0.811660 0.78320 4

1.472020 1.427380 1.435560 1.4401

317.56

12, 1186

Name

Formula

h31 h32 h33

Hexachlorodisiloxane Hexachloroethane 1,4,5,6,7,7-Hexachloro-5-norbornene-2,3-dicarboxylic anhydride Hexachloropropene Hexadecane 1,2-Hexadecanediol

h34 h35 h36 h37 h38

1-Hexadecanethiol Hexadecanoic acid 1-Hexadecanol 1-Hexadecene 1-Hexadecylamine

Cl3CC(Cl) ¨ CCl2 CH3(CH2)14CH3 CH3(CH2)13CH(OH)CH2OH CH3(CH2)15SH CH3(CH2)14COOH CH3(CH2)15OH CH3(CH2)13CH ¨ CH2 CH3(CH2)15NH2

h39

4-Hexadecylaniline

CH3(CH2)15C6H4NH2

h40 h41 h42

2,4-Hexadienal 1,5-Hexadiene 2,4-Hexadienoic acid

CH3CH ¨ CHCH ¨ CHCHO 96.13 H2C ¨ CHCH2CH2CH ¨ CH2 82.15 CH3CH ¨ CHCH ¨ 112.13 CHCOOH

h43 h44 h45

Hexafluorobenzene Hexafluoroethane 1,1,1,3,3,3-Hexafluoro-2-propanol cis-Hexahydroindane Hexamethylbenzene

C6F6 F3CCF3 (CF3)2CHOH

186.05 138.01 168.04

13, 132

C6(CH3)6

124.23 162.28

5, 82 5, 450

h46 h47

12, 809 1, 253 2, 483

Refractive index

Melting point

Boiling point

Flash point

35 137 187–188 235–239

0.89820 0.692320 4

1.538620 1.404220

1.618220 1.59078 1.59625

1.378120

0.876

1.4702

1.275020

s alc, bz, chl, eth

210 286.8

none 135

18–20 63–64 49.3 4.1 40–42

1847mm 21515mm 344 274 330

101

51–52 140.7 134.5

254– 25515mm 7630mm 67 59.5 1 11910mm 127

5.1 100.1 3

80.3 78.3 58.2

53 165.6

167 264

18.2 72–74

Solubility in 100 parts solvent

135 132 140

misc eth

sl s alc; s eth s hot alc, chl, eth s alc, chl, eth s alc, eth, PE v s alc, eth; s bz, chl

s alc, eth 0.2 aq; 13 alc; 9 acet; 2.3 bz; 11 diox; 1 CCl4

10 4 23

sl s alc, eth s aq, bz, CCl4 s eth v s bz; s acet, eth

h48 h49 h50 h51 h52 h53 h54 h55 h56 h57

Hexamethylcyclotrisiloxane 1,1,1,3,3,3-Hexamethyldisilazane Hexamethyldisiloxane Hexamethyleneimine Hexamethylenetetramine Hexamethylphosphoramide Hexanal Hexane 1,6-Hexanediamine 1,6-Hexanedioic acid

43, 1884

[ ˆ Si(CH3)2O ˆ ]3

222.48

(CH3)3SiNHSi(CH3)3

161.40

0.77420 4

1.407120

(CH3)3SiOSi(CH3)3

162.38

0.76420 4

1.377520

0.880 1.3315

1.463120 subl 263

1.02720

1.458820

0.833520 4 0.659420 4

1.403520 1.374920

99.18 140.19 [(CH3)2N]3P(O)

179.20

CH3(CH2)4CHO CH3(CH2)4CH3 H2N(CH2)6NH2 HOOC(CH2)4COOH

100.16 86.18 116.21 146.14

,,,,,-Hexachloro-p-xylene, b202 Hexadecyl mercaptan, h34 ,,,,,-Hexafluoro-3,5-xylidine, b205 Hexahydroaniline, c334 Hexahydro-2H-azepin-2-one, o57 Hexahydrobenzaldehyde, c315

20, 94 1, 583

12, 745 1, 142 4, 269 2, 649

64

1.36025 4

Hexahydrobenzoic acid, c317 Hexahydrobenzylamine, c324 Hexahydrophthalic acid, c320 Hexahydropyridine, p183 Hexamethylenediamine, h56 Hexamethylene diisocyanate, d410

67

133–135

35

126

22

101

1

138749mm

18 250

67 aq; 8 alc; 10 chl

7.2

233

105

misc aq

95.4 42 152

131 68.7 205 337.5

32 23 81 196

v s alc, eth; sl s aq misc alc, chl, eth v s aq; sl s alc, bz 1.4 aq; v s alc; s acet

Hexamethylene, glycol, h59 Hexamethylene oxide, o47 Hexamethylethane, t100 2,6,10,15,19,23-Hexamethyl-2,6,10,14,18,22tetracosahexene, s8 2,6,10,15,19,23-Hexamethyltetracosane, s7

1.261

1.262

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

h58 h59 h60

DL-Hexanediol 1,6-Hexanediol 2,5-Hexanediol

h61 h62 h63 h64 h65

2,5-Hexanedione Hexanedioyl dichloride Hexanenitrile 1-Hexanethiol 1,2,6-Hexanetriol

h66 h67 h68

Hexanoic acid Hexanoic anhydride 1-Hexanol

h69 h70

2-Hexanol 3-Hexanol

h71 h72 h73 h74

6-Hexanolactone 2-Hexanone Hexanoyl chloride 1,4,7,10,13,16-Hexaoxacyclooctadecane 1-Hexene trans-3-Hexenoic acid trans-2-Hexen-1-ol

h75 h76 h77

Formula weight

Beilstein reference

Density

Refractive index

CH3(CH2)3CH(OH)CH2OH HO(CH2)6OH CH3CH(OH)CH2CH2CH(OH)CH3 CH3COCH2CH2COCH3 ClC( ¨ O)(CH2)4COCl

118.18 118.18 118.18

11, 251 1, 484 1, 485

0.951 0.958 0.961745 16

1.442520 1.457925 1.446520

114.14 183.03

1, 788 2, 653

0.973 1.259

1.426020 1.470620

CH3(CH2)4CN CH3(CH2)5SH HOCH2CH(OH)(CH2)3CH2OH CH3(CH2)4COOH [CH3(CH2)4C( ¨ O)]2O CH3(CH2)5OH

97.16 118.24 134.17

2, 324 13, 1659

0.805220 0.842420 4 1.106320 20

1.406920 1.449620 1.4771

116.16 214.31 102.18

2, 321 2, 324 1, 407

0.926520 4 0.926 0.818620 4

CH3(CH2)3CH(OH)CH3 CH3CH2CH2CH(OH)CH2CH3

102.18 102.18

1, 408 1, 408

114.14 100.16 134.61 264.32

Formula

CH3(CH2)3COCH3 CH3(CH2)4COCl

CH3(CH2)3CH ¨ CH2 CH3CH2CH ¨ CHCH2COOH CH3CH2CH2CH ¨ CHCH2OH

Melting point

Boiling point

Flash point

223–234 243–250 220.8

112 101 101

191.4 1052mm

70 112

misc aq, alc, eth

80.3 80.5 32.8

163.6 152.7 1785mm

43 20 79

i aq; s alc, eth i aq; v s alc, eth misc alc, acet; i bz

1.416820 1.428020 1.418220

4.0 41 51.6

205.7 246–248 157.5

104 112 60

0.810825 4 0.819320 4

1.412825 1.416020

47

139.9 135

41 41

1.1 aq; v s alc, eth s alc 8 aq; misc bz, eth; s alc sl s aq; s alc, eth

172, 290 1, 689 2, 324

1.030 0.820920 4 0.975420 4

1.463020 1.402420 1.426320

9715mm 127.2 153

109 35 79

84.16 114.14

1, 215 2, 435

0.673220 0.963

1.387920 1.439820

63.5 11922mm

26 112

100.16

12, 486

0.849

1.434320

158–160

54

42.8 50 glass 6

56.9 87 40 139.8 11–12

Solubility in 100 parts solvent

v s aq, alc s aq, alc, eth

v s alc, eth d aq, alc; s eth

0.005 aq

h78 h79 h80

5-Hexen-2-one Hexyl acetate Hexylamine

H2C ¨ CHCH2CH2COCH3 CH3(CH2)5OOCCH3 CH3(CH2)5NH2

98.15 144.21 101.19

1, 734 2, 132 4, 188

h81

4-Hexylaniline

CH3(CH2)5C6H4NH2

177.29

123, 2759

h82 h83 h84 h85 h86 h87

1-Hexyne L-Histidine Hydantoin Hydrindantin Hydroxyacetaldehyde Hydroxyacetic acid

H(CH2)4C ˜ CH

82.14 155.16 100.08 322.27 60.05 76.05

13, 977 25, 513 24, 242 81, 631 1, 817 3, 228

HOCH2CHO HOCH2COOH

D-erythro-Hex-2-enoic acid -lactone, 159 Hexyl alcohol, h68 sec-Hexyl alcohol, e83 sec-Hexylamine, m353a Hexylbenzene, p117 Hexyl bromide, b294 Hexyl chloride, c129 Hexylene glycol, m338 Hexyl iodide, i39

Hexyl methyl ketone, o34 Hexyl propyl ketone, d16 Hippuric acid, b71 Histamine, i8 Homocysteine, a204 Homopiperidine, h51 Homoserines, a188, a189 Homoveratric acid, d447 Homoveratrylamine, d451

0.847 0.86020 20 0.76325 4

0.715220 4

1.366100

1.419720 1.409020 1.418020

1.398920

80 23

131.9 d 285 220 100 93–94 80

128–129 168–170 131–132 146– 14817mm 71.3

d 252 11012mm

23 37 8

0.13 aq; v s alc, eth sl s aq; misc alc, eth

i aq; s alc, eth 41 aq; v sl s alc s alc, alk; sl s eth v sl s aq v s aq, alc; sl s eth

Hydracrylonitrile, h169 2-Hydrazinoethanol, h120 Hydrazobenzene, d673 Hydrindene, i13 Hydrocinnamic acid, p146 Hydroquinone, d379 Hydroquinone dimethyl ether, d433 Hydroquinonesulfonic acid, d382 Hydroxyacetanilides, a15, a16, a17

1.263

1.264

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. h88 h89 h90 h91 h92 h93 h94 h95 h96 h97 h98

Name 1-Hydroxy-2-acetonaphthone Hydroxyacetone o-Hydroxyacetophenone m-Hydroxyacetophenone p-Hydroxyacetophenone 1-Hydroxyanthraquinone 2-Hydroxybenzaldehyde 3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde 2-Hydroxybenzaldehyde oxime 2-Hydroxybenzamide

Formula weight

Beilstein reference

C10H6(OH)COCH3

186.21

8, 149

HOCH2COCH3 HOC6H4COCH3

74.08 136.15

11, 84 8, 85

1.082 1.13121 4

HOC6H4COCH3

136.15

8, 86

1.100100

HOC6H4COCH3

136.15

8, 87

1.109100

224.22

8, 338

C6H4(OH)CHO

122.12

8, 31

C6H4(OH)CHO

122.12

8, 58

HOC6H4CHO

122.12

8, 64

C6H4(OH)CH ¨ NOH

137.14

8, 49

57

d

C6H4(OH)CONH2

137.14

10, 87

140

d 270

Formula

Density

Refractive index

Melting point

Boiling point

98–100

325 sl d

1.431520 1.558420

17 4–6

145–146 213717mm

1.535100

87–88

296

56 112

106–107 1473mm

Solubility in 100 parts solvent i aq; v s bz; s HOAc misc aq, alc, eth misc alc, eth; sl s aq s aq; v s alc, bz, eth v s alc, eth; sl s aq

196–198 1.16720 4

1.571820

7

196.7

100–102 19150mm 1.129130 4

117–119 subl

h99

2-Hydroxybenzoic acid

C6H4(OH)COOH

138.12

10, 43

1.44320 4

157–159 21120mm

h100

3-Hydroxybenzoic acid 4-Hydroxybenzoic acid

C6H4(OH)COOH

138.12

10, 134

1.473

201–203

HOC6H4COOH

138.12

10, 149

1.4684

214–215

h101

Flash point

76

1.7 aq86; s alc, eth s alc, bz, eth; sl s aq 1 aq; 70 acet; 4 bz; v s alc, eth v s alc, bz, eth, acid 0.2 aq; s alc, chl, eth 0.2 aq; 37 alc; 33 eth; 33 acet; 2 chl; 0.7 bz 0.8 aq; 10 eth 0.2 aq; v s alc; 23 eth

h102 h103 h104 h105 h106 h107 h108 h109 h110 h111 h112

p-Hydroxybenzophenone 1-Hydroxybenzotriazole 6-Hydroxy-1,3-benzoxathiol-2-one 2-Hydroxybenzyl alcohol 3-Hydroxy-2-butanone p-Hydroxycinnamic acid 4-Hydroxycoumarin 7-Hydroxycoumarin 1-Hydroxy-1-cyclohexanecarbonitrile 2-Hydroxy-3,5diiodobenzoic acid 2-Hydroxy-4,6-dimethylacetophenone

2-Hydroxybenzenemethanol, h105 m-Hydroxybenzotrifluoride, t290

198.22

82, 184

132–135

135.13

26, 41

155–158

168.17

194, 2508

158–160

124.13

6, 891

1.16125

88.10

1, 827

0.997

164.16

10, 297

210–213

162.14 162.14

17, 488 18, 27

213 d 226–228 subl

C6H10(OH)CN

125.17

10, 5

I2C6H2(OH)COOH

389.91

10, 113

(CH3)2C6H2(OH)COCH3

164.20

HOC6H4COC6H5

HOC6H4CH2OH CH3COCH(OH)CH3 HOC6H4CH ¨ CHCOOH

2-Hydroxybiphenyl, p131 4-Hydroxybiphenyl, p132

1.031

1.417120

1.457620

v s alc, eth; sl s aq

86–87

subl 100

15

148

29 235 d

50

6.6 aq; v s alc, chl, eth; s bz misc aq, alc; sl s eth s alc, eth; sl s aq s aq, alc, eth v s alc, chl, alk, HOAc

60 v s alc, eth; i bz, chl

53–57

Hydroxybutanedioic acids, h180, h181

1.265

1.266

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. h113 h114

h115 h116 h117 h118 h119

h120 h121 h122 h123 h124

Name 2-Hydroxydiphenylmethane 2-Hydroxyethanesulfonic acid, Na salt N-(2-Hydroxyethyl)acetamide 2-Hydroxyethyl acetate 3-(-Hydroxyethyl)aniline 2-Hydroxyethyl disulfide N-(2-Hydroxyethyl)ethylenediamineN,N,N-triacetic acid 2-Hydroxyethylhydrazine 2-Hydroxyethyl methacrylate N-(-Hydroxyethyl)morpholine N-(-Hydroxyethyl)piperazine N-(2-Hydroxyethyl)piperazine-Nethanesulfonic acid

Formula weight

Beilstein reference

184.24

6, 675

20.6

HOCH2CH2SO Na+

148.11

43, 42

191–194

HOCH2CH2NHCOCH3

103.12

41, 430

1.123320 20

CH3COOCH2CH2OH

104.11

2, 141

1.10815

CH3CH(OH)C6H4NH2

137.18

133, 1654

HOCH2CH2SSCH2CH2OH

154.25

1, 471

HOOCCH2N(CH2CH2OH)CH2CH2N(CH2COOH)2

278.26

Formula C6H5CH2C6H4OH  3

HOCH2CH2NHNH2 HOCH2CH2OOCC(CH3) ¨ CH2

76.10

Density

Refractive index

1.457520

Melting point

63–65

Boiling point

Flash point

312

s alc, chl, eth, alk v s aq

d

176

misc aq: sl s bz

181–186

102

misc aq, alc, chl, eth

220

73

misc aq; s alc

68–71 1.261

1.565520

25–27

1583.5mm

212 d

41, 562

130.14

70

1.119 1.034

1.451520

673.5mm

97

131.18

27, 7

1.083

1.476020

227

99

130.19

232, 6

1.061

1.506520

246

112

238.31

Solubility in 100 parts solvent

234 d

misc aq

h125 h126 h127 h128

h129

h130 h131 h132

4-(2-Hydroxyethyl)piperidine 2-(2-Hydroxyethyl)pyridine 2-Hydroxyisobutyric acid 4-Hydroxy-2-mercapto-6-methylpyrimidine 4-Hydroxy-2-mercapto-6-propylpyrimidine 2-Hydroxy-3-methoxybenzaldehyde 4-Hydroxy-3-methoxybenzaldehyde 4-Hydroxy-3-methoxybenzoic acid

129.20

212, 10

1.005915 4

HOCH2CH2C5H4N

123.16

21, 50

1.093

(CH3)2C(OH)COOH

104.11

3, 313

77–80

142.18

243, 1289

330 d

199–202 1.536820

170.23

841.5mm

219–221

CH3OC6H3(OH)CHO

152.15

8, 240

CH3OC6H3(OH)CHO

152.15

8, 247

CH3OC6H3(OH)COOH

168.15

10, 392

Hydroxyethanal, h86 3-(-Hydroxyethyl)aniline, a261 N-(2-Hydroxyethyl)-3-aza-1,5-pentanediol, t264

1169mm

1.056

N-(2-Hydroxyethyl)ethyleneimine, a321 N-(2-Hydroxyethyl)piperidine, p185 2-(2-Hydroxyethyl)piperidine, p186

92

v s aq, alc, chl v s aq, alc, eth

0.1 aq; 1.7 alc; 1.7 acet; v s alk; i bz

40–42

265–266

v s alc, eth; sl s aq

80–81

285

1 aq; s alc, chl, pyr

210

0.12 aq; v s alc

O-Hydroxyethylresorcinol, h159 2-Hydroxyisobutyronitrile, h145 2-Hydroxy-3-methyl-2-cyclopenten-1-one, m214

1.267

1.268

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. h133 h134 h135 h136

h137 h138 h139 h140 h141

h142 h143 h144 h145

Name 4-Hydroxy-3-methoxybenzonitrile 2-Hydroxy-4-methoxybenzophenone 4-Hydroxy-3-methoxybenzyl alcohol 4-Hydroxy-3-methoxycinnamic acid 2-Hydroxy-3-methylbenzoic acid 2-Hydroxy-4-methylbenzoic acid 4-Hydroxy-3-methyl2-butanone 7-Hydroxy-4-methylcoumarin 2-Hydroxymethyl-2methyl-1,3propanediol 4-Hydroxy-4-methyl2-pentanone N-(Hydroxymethyl)phthalimide 4-Hydroxy-N-methylpiperidine 2-Hydroxy-2-methylpropanenitrile

Formula weight

Beilstein reference

CH3OC6H3(OH)CN

149.15

10, 398

85–87

CH3OC6H3(OH)COC6H5

228.25

8, 312

66

CH3OC6H3(OH)CH2OH

154.17

6, 1113

113–115

CH3OC6H3(OH)CH ¨ CHCOOH

194.19

10, 436

174

CH3C6H3(OH)COOH

152.15

10, 220

165–166

s hot aq, alc, eth, EtAc; sl s bz, PE s alc, chl, eth, alk

CH3C6H3(OH)COOH

152.15

10, 233

177

s alc, chl, eth, alk

HOCH2CH(CH3)COCH3

102.13

11, 422

176.17

18, 31

194–195

HOCH2C(CH3)(CH2OH)2

120.09

1, 520

199–203

(CH3)2C(OH)CH2COCH3

116.16

Formula

(CH3)2C(OH)CN

0.993

0.938520

177.16

21, 475

115.18

211, 188

85.10

Density

3, 316

Refractive index

Melting point

1.434020

1.423520

Boiling point

1555mm

9215mm

42.8

Flash point

v s alc, chl, eth

78 s alc, HOAc; sl s eth

169

12

142–145

0.926725 4

Solubility in 100 parts solvent

misc aq sl s aq, alc, bz

1.477520

29–31

200

112

1.399220

19

95

63

s aq, alc, chl, eth

h146

3-Hydroxy-2-methyl4-pyrone

h147

2-Hydroxy-1-naphthaldehyde 1-Hydroxy-2-naphthalenecarboxylic acid 3-Hydroxy-2-naphthalenecarboxylic acid 2-Hydroxy-3,6naphthalenedisulfonic acid, disodium salt 4-Hydroxy-2,7naphthalenedisulfonic acid, disodium salt 2-Hydroxy-1,4naphthoquinone

h148

h149

h150

h151

h152

3-Hydroxymethylpiperidine, p187

126.11

161–162

1.2 aq; v s hot aq; s alc, alk; sl s bz, eth 19227mm

C10H6(OH)CHO

172.18

8, 143

82–85

C10H6(OH)COOH

188.18

10, 331

191–192

v s alc, bz, eth, alk

C10H6(OH)COOH

188.18

10, 333

222–223

v s alc, eth; s bz, chl

 C10H5(OH)(SO 3 Na )2

348.25

11, 288

 C10H5(OH)(SO 3 Na )2

348.25

11, 227

 300

174.16

8, 300

d 185

1-Hydroxy-2-napthoic acid, h148

v s aq, alc; i eth

s HOAc

3-Hydroxy-2-naphthoic acid, h149

1.269

1.270

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. h153

h154 h155 h156 h157 h158 h159 h160 h161 h162 h163 h164

h165

Name 4-Hydroxy-3-nitrobenzenearsonic acid 3-Hydroxy-4-nitrobenzoic acid 2-Hydroxy-5-nitrobenzyl bromide 5-Hydroxy-1-pentanal 5-Hydroxy-2pentanone 4-Hydroxy-3-penten2-one acetate 2-(m-Hydroxyphenoxy)ethanol 4-Hydroxyphenylacetic acid 2-Hydroxy-N-phenylbenzamide 4-(p-Hydroxphenyl)2-butanone D-()-p-Hydroxyphenylglycine N-(p-Hydroxyphenyl)glycine 1-(3-Hydroxyphenyl)urea

Formula weight

Beilstein reference

HOC6H3(NO2)AsO(OH)2

263.04

161, 456

300

HOC6H3(NO2)COOH

183.12

10, 146

229–231

HOC6H3(NO2)CH2Br

232.04

6, 367

147–149

HO(CH2)4CHO CH3COCH2CH2CH2OH

102.13 102.13

1, 831

CH3COOC(CH3) ¨ CHCOCH3 HOC6H4OCH2CH2OH

142.15

HOC6H4CH2COOH

152.15

10, 190

149–151 subl

v s alc, eth; sl s aq

HOC6H4CONHC6H5

213.14

12, 500

136

v s alc, bz, chl, eth

HOC6H4CH2CH2COCH3

164.20

HOC6H4CH(NH2)COOH

167.16

141, 659

240 d

HOC6H4NHCH2COOH

167.16

13, 488

220– 248 d

HOC6H4NHCONH2

152.15

13, 417

182–184

Formula

154.17

Density

1.055 1.00720 4

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent v s alc, acet, HOAc, alk; sl s aq; i eth

1.453020 1.437220

11515mm 144100mm

112 93

1.452520

195

75

s aq misc aq; s alc, eth

83–86

82–83 sl s aq, alc, bz, acet s alk, acid; v sl s aq, alc, acet, bz, chl, eth

h166 h167 h168 h169 h170 h171 h172 h173 h174 h175 h176

N-Hydroxyphthalimide N-Hydroxypiperidine 2-Hydroxypropionitrile 3-Hydroxypropionitrile o-Hydroxypropiophenone p-Hydroxypropiophenone 1-(2-Hydroxy-1-propoxy)-2-propanol 2-Hydroxypyridine 3-Hydroxypyridine 4-Hydroxypyridine 2-Hydroxypyridine5-carboxylic acid

163.13

21, 500

233 d

101.15

20, 80

37–40

11155mm

CH3CH(OH)CN

71.08

32, 209

0.983425

1.402725

34

10350mm

77

misc aq, alc; s eth

HOCH2CH2CN

71.08

3, 298

1.040425 4

1.425620

46

228

112

HOC6H4COCH2CH3

150.18

8, 102

1.094

1.548020

11515mm

112

misc aq, alc, acet; 2.3 eth; i bz, PE v s alc, eth; sl s aq

HOC6H4COCH2CH3

150.18

8, 102

CH3CH(OH)CH2OCH2CH(OH)CH3 HOC5H4N

134.18 95.10

21, 43

105–107 280–281

HOC5H4N HOC5H4N HO(C5H3N)COOH

95.10 95.10 139.11

21, 46 21, 48 22, 215

126–129 1513mm 23012mm 300

6-Hydroxynicotinic acid, h176 -Hydroxy--phenylacetophenone, b46 3-(p-Hydroxyphenyl)alanine, t437

148 1.025220 20

1.444020

2-Hydroxy-2-phenylbenzeneacetic acid, b36 3-Hydroxy-1-propanesulfonic acid -sultone, p198

v s alc, eth; sl s aq 231.8

138

misc aq, alc s aq, alc, bz; sl s eth v s aq, alc; sl s eth v s aq; i alc, bz, eth sl s aq, alc, eth

2-Hydroxypropanoic acids, L1, L2 1-Hydroxy-2-propanone, h89 3-Hydroxypropionitrile, c290

1.271

1.272

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. h177 h178 h179 h180

h181

Name 3-HydroxypyridineN-oxide 8-Hydroxyquinoline 8-Hydroxyquinoline5-sulfonic acid DL-Hydroxysuccinic acid L-Hydroxysuccinic

Formula (HO)C5H4N ¨ O

Formula weight

Beilstein reference

Density

Refractive index

111.10

Melting point

Boiling point

Flash point

190–192

145.16

21, 91

76

225.22

22, 407

213 d

HOOCCH(OH)CH2COOH

134.09

3, 435

131–133

HOOCCH(OH)CH2COOH

134.09

3, 419

100

115.09

21, 380

93–95

267

v s alc, acet, bz, chl v s aq; sl s alc, eth 56 aq; 45 EtOH: 18 acet; 0.8 eth; 23 diox; i bz 36 aq; 87 EtOH; 2.7 eth; 61 acet; 75 diox v s aq

acid h182 h183

h184

h185

h186 i1 i2 i3

N-Hydroxysuccinimide 6-Hydroxytetrahydropyran-2-carboxylic acid lactone 3-Hydroxy-3,7,11trimethyl-1,6,10dodecatriene 3-Hydroxy-2,2,4trimethyl-3pentenoic acid -lactone Hypoxanthine 1H,1H,11H-Icosafluoro-1-undecanol Icosane 1-Icosene

H2C ¨ CHC(OH)(CH3)CH2CH2CH ¨ C(CH3)CH2CH2CH ¨ C(CH3)2

Solubility in 100 parts solvent

128.13

1.226

1.459320

222.37

0.876025 4

1.476925

140.18

0.947

1.438020

136.11 531.1

26, 416

HCF2(CF2)9CH2OH CH3(CH2)18CH3 CH3(CH2)17CH ¨ CH2

282.56 280.54

1, 174 13, 881

0.777737

1.434640

1141mm

96

18

170

62

d 150 95–97

181200mm

36.4 28.7

343.8 342.4

s abs alc

0.25 aq; s alk, acid 112

i4 i5 i6 i7 i8 i9 i10 i11 i12 i13 i14 i15

Imidazole 2-Imidazolidinethione Imidazolidinetrione 2-Imidazolidone 2-(4-Imidazolyl) ethylamine 3,3-Iminobispropylamine Iminodiacetic acid Iminodiacetonitrile Iminodibenzyl Indan 5-Indanol 1-Indanone

5-Hydroxyvaleraldehyde, h156 Imidodicarbonic diamide, b215

H2NCH2CH2CH2NHCH2CH2CH2NH2 HOOCCH2NHCH2COOH NCCH2NHCH2CN

68.08 102.16

23, 45 24, 4

90–91 257 203–204

114.06 86.09 111.15

230 131 83–84

subl 100

24, 16 25, 315

14

15150mm

131.22 133.10 95.11 195.27 118.18 134.18 132.16 Indalone, b445

0.938

1.481020

4, 365 4, 367

6, 575 7, 360

0.963920 4

1.536020

1.109045 4

1.56145

145

20918mm

243 d 77 105–108 51.4 176.5 51–53 255 40–42 243–245

v s aq, alc, chl, eth 2 aq; s alc, pyr; i bz, acet, chl, eth 5 aq; s alc v s aq, hot alc v s aq, alc, hot chl

118 2 aq; v sl s bz, eth s aq, alc: sl s eth 50

Indanamines, a199, a200

s alc, chl, eth; i aq v s alc, eth; sl s aq s alc, eth; sl s aq

1.273

1.274

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. i16

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

178.14

i17

1,2,3-Indantrione hydrate Indene

116.16

5, 515

0.996820 4

1.576220

1.8

i18 i19 i20 i21

Indole Indole-3-acetic acid Indole-3-carbaldehyde Indole-2,3-dione

117.15 175.19 145.16 147.13

20, 304 22, 66 21, 313 21, 432

1.0643

1.60960

52 253 168–170 195–198 203.5 d

i22 i23 i24 i25 i26 i27 i28 i29 i30 i31 i32 i33 i34

Indoline Inositol Iodoacetamide Iodoacetic acid 3-Iodoaniline Iodobenzene Iodobenzene diacetate 2-Iodobenzoic acid 1-Iodobutane 2-Iodobutane Iodocyclohexane 1-Iododecane Iodoethane

20, 257 62, 1157 2, 223 2, 222 12, 670 5, 215

1.063 1.752

1.590620

ICH2CONH2 ICH2COOH IC6H4NH2 C6H5I C6H5I(OOCCH3)2 IC6H4COOH CH3CH2CH2CH2I CH3CH2CH(I)CH3 C6H11I CH3(CH2)9I CH3CH2I

119.17 180.16 184.96 185.95 219.03 204.01 322.10 248.02 184.02 184.02 210.06 268.18 155.97

1.821 1.838325 4

1.682020 1.62118

52, 13 1, 168 1, 96

2.24925 4 1.61620 4 1.59220 4 1.62615 15 1.25720 4 1.935820

1.499920 1.499120 1.547220 1.482720 1.5137

i35 i36

2-Iodoethanol Iodoform

ICH2CH2OH CHI3

171.97 393.73

1, 339 1, 73

2.219720 4 4.008

1.569420

i37 i38

1-Iodoheptane 1-Iodohexadecane

CH3(CH2)6I CH3(CH2)15I

226.10 352.35

1, 155 1, 172

1.37320 4 1.121

1.490020 1.480620

Flash point

Solubility in 100 parts solvent

d 241

9, 363 1, 123

225–227 91–93 82–83 25 30 163–165 162 103.5 104.0 110.9

181.6

221

92

14615mm 188.3

112 74

129–130 118–120 180 13215mm 72.4

33 28

755mm 120–123 48.2

78

none 65 none

204 78 206– 20710mm

misc alc, bz, chl, eth s hot aq, bz, eth v s alc; s acet, eth s hot aq, hot alc, alk sl s aq 14 aq; sl s aq; i eth s hot aq s aq, alc; v sl s eth i aq; s alc, eth misc alc, chl, eth s alc, eth; sl s aq i aq; s alc, eth i aq; s alc, eth i aq; s eth i aq; s alc, eth 0.4 aq; misc alc, bz, chl, eth s aq; v s alc, eth 1.4 alc; 10 chl; 13 eth; v s bz, acet i aq; s alc, eth

1.43720 4 2.278920 4

1.492620 1.530820

i39 i40

1-Iodohexane Iodomethane

CH3(CH2)5I CH3I

212.08 141.94

1, 146 1, 69

i41

4-Iodomethoxybenzene 1-Iodo-3-methylbutane 1-Iodo-2-methylpropane 2-Iodo-2-methylpropane 1-Iodo-3-nitrobenzene 1-Iodooctane 1-Iodopentane 1-Iodopropane

IC6H4OCH3

234.04

6, 208

(CH3)2CHCH2CH2I

198.06

13, 367

1.50920 4

(CH3)2CHCH2I

184.02

1, 128

1.60320 4

(CH3)3CI

184.02

13, 326

1.57100

1.491820

38.2

IC6H4NO2 CH3(CH2)7I CH3(CH2)4I CH3CH2CH2I

249.01 240.13 198.06 169.99

5, 253 1, 160 1, 133 1, 113

1.947750 4 1.33020 4 1.51220 4 1.748920

1.488920 1.495420 1.505820

36–38 45.9 85.6 101

i42 i43 i44 i45 i46 i47 i48

Indonaphthene, i17

4-Iodoanisole, i41

66.5

179.5 42.4

48–50

237726mm

1.493920

61 none

147.5 93.5

i aq 1.4 aq; misc alc, eth s hot alc, eth misc alc, eth; sl s aq i aq; misc alc, eth

119

d aq; misc alc, eth 280 221 154.5 102.5

79 none

5-Iodoanthranilic acid, a203

i aq; s alc, eth s alc, eth sl s aq; s alc, eth 0.1 aq; misc alc, eth

1.275

1.276

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

i49

2-Iodopropane

(CH3)2CHI

169.99

1, 114

1.7025420

1.499220

90.0

i50 i51 i52 i53 i54 i55 i56 i57 i58

3-Iodo-1-propene 5-Iodosalicylic acid 2-Iodothiophene 2-Iodotoluene 3-Iodotoluene Iodotrimethylsilane -Ionone -Ionone Isatoic anhydride

ICH2CH ¨ CH2 IC6H3(OH)COOH

167.97 264.02 210.04 218.04 218.04 200.10 192.30 192.30 163.13

13, 114 10, 112 17, 34 5, 310 5, 311

1.84522 4

1.554021

1.902 1.713 1.698 1.40620 4 0.93220 0.94617

1.652020 1.607920 1.604020 1.471020 1.498020 1.52117

99 1–3 189–191 40 7315mm 211 8010mm 106 12411mm 14018mm 233 d

i59

D-()-Isoascrobic

i60 i61

i62 i63 i64 i65

acid DL-Isoborneol 2-Isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline Isobutyl acetate Isobutylamine

i66 i67

Isobutylbenzene Isobutyl chloroformate Isobutyl formate Isobutyl isobutyrate

i68

Isobutyl lactate

IC6H4CH3 IC6H4CH3 (CH3)3SiI

7, 168 7, 167 27, 264

176.12

89.5

Flash point none

71 90 82 1 104  112

169 d

154.25 303.40

62, 80

(CH3)2CHCH2OOCCH3 (CH3)2CHCH2NH2

116.16 73.14

C6H5CH2CH(CH3)2 ClCOOCH2CH(CH3)2 HCOOCH2CH(CH3)2 (CH3)2CHCH2OOCCH(CH3)2 CH3CH(OH)COOCH2CH(CH3)2

212

subl 1400.2mm

 112

98.9 84.6

118.0 67.7

25 26

1.485520 1.407020

51.5

172.8 128.8

55 26

0.885420 4 0.854220

1.385520 1.399920

94.5 80.7

98.4 147.5

10

0.97120 20

1.418125

1.022

1.523020

2, 131 4, 163

0.874520 0.724204

1.390220 1.397220

134.22 136.58

5, 414 3, 12

0.867320 4 1.053

102.13 144.22

2, 21 2, 291

146.19

32, 188

9640mm

Solubility in 100 parts solvent 0.14 aq; misc alc, bz, chl, eth misc alc, chl, eth v s alc; i bz, chl v s eth i aq; s alc, eth i aq; misc alc, eth s alc, bz, chl, eth s alc, bz, chl, eth sl s aq, hot alc, acet s aq, alc, acet, pyr v s alc, chl, eth

0.7 aq; v s alc misc aq, alc, acet, eth misc alc, eth misc bz, chl, eth 1 aq; misc alc, eth 0.5 aq; misc alc

i69

Isobutyl methacrylate

i70 i71 i72 i73

Isobutyl nitrate Isobutyl nitrite Isobutyl vinyl ether Isobutyraldehyde

H2C ¨ C(CH3)COOCH2CH(CH3)2 (CH3)2CHCH2ONO2 (CH3)2CHCH2ONO (CH3)2CHCH2OCH ¨ CH2 (CH3)2CHCHO

i74 i75

Isobutyramide Isobutyric acid

(CH3)2CHCONH2 (CH3)2CHCOOH

Isatin, i21 Isethionic acid, h114 Isoamyl acetate, i80 Isoamyl alcohol, m155 sec-Isoamyl alcohol, m156 Isoamyl bromide, b305 Isoamyl iodide, i42 Isoamyl nitrite, i81

142.19

0.88225 15

1.417025

155

119.12 103.12 100.16 72.11

1, 671

1.01520 4 0.87022 4 0.770220 20 0.798820 4

1.402820 1.371522 1.396120 1.372320

132.3 65.9

123–125 67 83.4 63–64

2, 293 2, 288

1.013 0.95020 4

127–129 1.392520

216–220 46 154

87.12 88.11

1, 377

Isobutane, m375 Isobutene, m383 -Isobutoxy--phenylacetophenone, b48 Isobutylacetylene, m352 Isobutyl alcohol, m381 Isobutyl bromide, b310 Isobutyl chloride, c161 Isobutyl chlorocarbonate, i65

45

4 40

55

misc alc, eth i aq; misc alc, eth misc alc; sl s aq(d) 0.2 aq 11 aq; misc alc, bz, acet, chl, eth 17 aq; misc alc, chl, eth

Isobutyl 1,2-dihydro-2-isobutoxy-1quinolinecarboxylate, i61 Isobutyl ether, d407 Isobutyl heptyl ketone, t349 Isobutyl mercaptan, m379 Isobutyraldehyde, m374 Isobutyramide, m388 Isobutyric acid, m390

1.277

1.278

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

i76 i77 i78 i79

Isobutyronitrile Isobutyrophenone Isobutyryl chloride L-Isoleucine

i80

Isopentyl acetate

i81

Isopentyl nitrite

i82 i83 i84 i85

Isophorone DL-Isopinocampheol Isopropenyl acetate 2-Isopropoxyphenol

i86

1-Isopropoxy-2propanol Isopropyl acetate Isopropylamine 2-Isopropylaminoethanol 2-Isopropylaniline Isopropylbenzene 4-Isopropylbenzyl alcohol N-Isopropylbenzylamine Isopropylcyclohexane N-Isopropylcyclohexylamine

i87 i88 i89 i90 i91 i92 i93 i94 i95

Formula (CH3)2CHCN C6H5COCH(CH3)2 (CH3)2CHCOCl CH3CH2CH(CH3)CH(NH2)COOH CH3COOCH2CH2CH(CH3)2 (CH3)2CHCH2CH2ONO

CH3COOC(CH3) ¨ CH2 (CH3)2CHOC6H4OH

Formula weight

Beilstein reference

Density

Refractive index

Melting point

69.11 148.21 106.55 131.18

2, 294 7, 316 2, 293 4, 454

0.770420 0.98820 1.017

1.373420 1.5172 1.407320

71.5

130.19

2, 132

0.87615 4

1.400720

117.15

1, 402

0.872

1.386020

138.21 154.25 100.12 152.19

7, 65 6, 67 22, 278 63, 4209

0.923

1.475920

0.909 1.030

1.400520 1.515720

0.87925 25

1.40725

118.1

Flash point

Solubility in 100 parts solvent

3 84 1

v s alc, eth; sl s aq

90 d 284

103.8 217 91–93 subl 168

78.5

142.0

25

99

10

0.25 aq; misc alc, eth misc alc, eth; sl s aq 1.2 aq

8.1 35–36

215.2 84 217 94 18 100– 10211mm 47.9 49 88.2 32.4 7511mm

CH3CH(OH)CH2OCH(CH3)2 (CH3)2CHOOCCH3 (CH3)2CHNH2 (CH3)2CHNHCH2CH2OH

102.13 59.11 103.17

2, 130 4, 152 4, 282

0.87020 4 0.68625 4 0.897020 4

1.377320 1.371125 1.439520

73.4 101

(CH3)2CHC6H4NH2 C6H5CH(CH3)2 (CH3)2CHC6H4CH2OH

135.2 120.20 150.22

5, 393 63, 1911

0.966 0.86420 4 0.98215

1.491520 1.520620

96.0 28

C6H5CH2NHCH(CH3)2

149.24

0.892

1.502520

C6H11CH(CH3)2 C6H11NHCH(CH3)2

126.24 141.26

0.802320 4 0.859

1.439920 1.448020

5, 41

Boiling point

90

d aq, d alc; s eth 4 aq; sl s hot alc

16 17

3 aq; misc alc, eth misc aq, alc, eth misc aq, alc, eth

222 152.4 248.4

46 112

s alc, bz, eth misc alc, eth; i aq

200

87

155 6012mm

35 33

v s alc, eth

i96

i97 i98 i99

4,4-Isopropylidenebis[2-(2,6-dibromophenoxy)ethanol] 4,4-Isopropylidenediphenol Isopropyl isocyanate Isopropyl S-()lactate

Isocapronitrile, m339 Isocinchomeronic acid, p260 Isocrotonic acid, b401 Isodurene, t98 Isoeugenol, m98 Isohexane, m336 Isoleucinol, a216 Isoniazid, p258 Isonicotinaldehyde, p253 Isonicotine acid, p257 Isonicotinic acid hydrazide, p258 Isonicotinonitrile, c297 Isooctane, t354

(CH3)2C[C6H2(Br)2OCH2CH2OH]2

632.01

107

(CH3)2C[C6H4OH]2

228.29

6, 1011

(CH3)2CHCNO (CH3)2CHOOCCH(OH)CH3

85.11 132.16

4, 155 3, 282

153–156 2204mm 0.866 0.99820 20

1.382520 1.408225

Isopentane, m149 Isopentyl alcohol, m155 Isopentyl isovalerate, m170 Isophorone, t340 Isophthalic acid, b16 Isophthalonitrile, d237 Isophthaloyl dichloride, b14 Isoprene, m147 Isopropanolamine, a269 Isopropenyl acetate, p208 Isopropenylacetylene, m166 4-Isopropenyl-1-cyclohexene-1-carbaldehyde, p58

74–75 166–168

2

Isopropenyl methyl ether, m96 Isopropylacetylene, m171 Isopropylacrylic acid, m349 Isopropyl alcohol, p203 Isopropyl chloride, c211 Isopropyl cyanide, i76 Isopropyl ether, d417 Isopropylethylene, m160 Isopropylidone acetone, m350 Isopropyl iodide, i49

s aq, alc, eth

1.279

1.280

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. i100

Name

i109 i110 k1 L1 L2 L3 L4

2-Isopropyl-1-methylbenzene 3-Isopropyl-1-methylbenzene 4-Isopropyl-1-methylbenzene 2-Isopropyl-5-methylphenol N1-Isopropyl-2methyl-1,2propanediamine Isopropyl methyl sulfide Isopropyl nitrate 2-Isopropylphenol 4-Isopropylphenol Isopropyl vinyl ether Isopulegol Isoquinoline Ketene DL-Lactic acid L-()-Lactic acid -Lactose DL-Leucine

L5

L-Leucine

i101 i102 i102a i103

i104 i105 i106 i107 i108

Formula weight

Beilstein reference

Density

Refractive index

Melting point

CH3C6H4CH(CH3)2

134.21

5, 419

0.876620 4

1.500620

71.5

178.2

misc alc, eth

CH3C6H4CH(CH3)2

134.21

5, 419

0.861020 4

1.493020

63.75

175.1

misc alc, eth

CH3C6H4CH(CH3)2

134.21

5, 420

0.857320 4

1.490920

67.9

177.1

CH3C6H3(OH)CH(CH3)2 (CH3)2C(NH2)CH2NHCH(CH3)2

150.22

6, 532

0.92580 4

49–51

232

Formula

(CH3)2CHSCH3

130.24

90.18

0.822

1, 367

(CH3)2CHONO2 (CH3)2CHC6H4OH (CH3)2CHC6H4OH (CH3)2CHOCH ¨ CH2

105.09 136.19 136.19 86.13

13, 1465 6, 504 6, 505

H2C ¨ C ¨ O CH3CH(OH)COOH CH3CH(OH)COOH

154.25 129.16 42.04 90.08 90.08 342.30 131.18

6, 65 20, 380 1, 724 3, 268 3, 261 31, 408 4, 447

131.18

4, 437

(CH3)2CHCH2CH(NH2)COOH (CH3)2CHCH2CH(NH2)COOH

1.426920

1.03619 19 1.01220 0.99020 0.75320 4

1.391216 1.525920

0.911 1.091030 4

1.472520 1.620830

1.24915 4 1.206025 4 1.52520

1.439220

1.29318

1.384920

Boiling point

147–149

101.5

84.7

15–16 59–61 140

102.1 212–213 212 5–6

26.5 151 16.8 53 219 d d 332 d 293

9112mm 243.2 41 12214mm 11912mm subl 293 subl 145

Flash point

47

Solubility in 100 parts solvent

misc alc, eth i aq; v s alc, chl, eth

90

107

misc alc, eth 316 alc; 350 eth

78 107

v sl s aq sl s aq; s acid s acet, eth; d aq s aq, alc; i chl v s aq, alc, eth 17 aq; i alc, eth 1 aq; 0.13 alc; i eth

112

2.4 aq; 0.07 alc; 1 HOAc; i eth

L6 L7 L8 L9 L10 L11

()-Limonene ()-Limonene ()-Limonene oxide Linalool Linalyl acetate N-Lithiohexamethyldisilazane

(CH3)3SiN(Li)Si(CH3)3

Isopropyl mercaptan, p200 1-Isopropyl-4-methyl-1,3-cyclohexadiene, t5 1-Isopropyl-4-methyl-1,4-cyclohexadiene, t6 Isopropyl methyl ketone, m157 Isopropyltolueness, i100, i101, i102 Isopseudocumenol, t358 Isovaleraldehyde, m174 Isovaleric acid, m177 Isovaleronitrile, m178 Isovaleryl chloride, m179 Itaconic acid, m245

136.24 136.24 152.24 154.25 196.29 167.3

5, 133 5, 136 17, 44 1, 462 2, 141

0.841120 4 0.844 0.929 0.86515 0.89520

Keto compounds, see Oxo 2-Ketobutyric acid, o56 5-Keto-1,7,7-trimethylnorcamphane, c3 4-Ketovaleric acid, o58 Koshland’s reagent I, h155 Lactonitrile, h168 Lauraldehyde, d731 Lauric acid, d726 Lauronitrile, d724 Lauroyl chloride, d728 Lauryl alcohol, d727

1.4715 1.470620 1.466120 1.461520 1.451

96.5 96.5

70–72

175–176 175–176 11450mm 199 220 d 115

53 48 65 76 84

Laurylamine, d732 Lauryl bromide, b275 Lauryl mercaptan, d725 Lauryl sulfate, d735 Lepidine, m408 Leucinol, a217 Levulinic acid, o58 Linoleic acid, o1 Linolenic acid, o7

misc alc, eth misc alc, eth misc alc, eth misc alc, eth

1.281

1.282

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula H2N(CH2)4CH(NH2)COOH HOOCCH ¨ CHCOOH

Formula weight

Beilstein reference

146.19

4, 435

116.07 98.06

2, 748 17, 432

1.590 1.48

138–139 52.8 202.0

Density

Refractive index

Melting point

Boiling point

Flash point

L12

L-()-Lysine

m1 m2

Maleic acid Maleic anhydride

m3

Malonic acid

HOOCCH2COOH

104.06

2, 566

1.63

135 d

m4 m5

Malonodiamide Malononitrile

H2NCOCH2CONH2 NCCH2CN

102.09 66.06

2, 582 2, 589

1.049

168–170 32–34 220

m6 m7

ClCOCH2COCl

140.95 342.30

21, 252 31,386

1.448619 4 1.54017

m8

Malonyl dichloride D-()-Maltose hydrate D-Mandelic acid

C6H5CH(OH)COOH

152.15

10, 197

1.30020 4

m9

Mandelonitrile

C6H5CH(OH)CN

133.15

10, 193

1.117

m10 m11

Mannitol D-()-Mannose

182.17 180.16

1, 534 31, 284

1.5220 1.5420

m12 m13

L-Menthol

156.27 154.25

6, 28 7, 38

0.89015 15 0.89520 4

1.45825 1.451020

43–45 6

212 207

93 69

m14

Mercaptoacetic acid

92.12

3, 245

1.325

1.503020

16.5

965mm

112

m15

2-Mercaptobenzimidazole

150.20

24, 119

L-Menthone

HSCH2COOH

d 224

1.462020

1.531520

v s aq; sl s alc; i eth

5319mm 102–103 d 130 119

d

10

d 170

103

112 47

166–168 2903.5mm 128–130

303–304

Solubility in 100 parts solvent

79 aq; 70 alc; 8 eth s aq (to acid), alc (to ester); 227 acet; 53 chl; 50 bz; 112 EtAc 154 aq; 42 alc; 8 eth 9 aq; i alc, eth 13 aq; 40 alc; 20 eth d hot aq; s eth v s aq; sl s alc; i eth 16 aq; 100 alc; s eth v s alc, chl, eth; i aq 18 aq; 1.2 alc; i eth 250 aq; 28 pyr; 0.8 alc v s alc, chl, eth, PE misc alc, eth; sl s aq misc aq, alc, bz, eth sl s aq; s alc

m16

o-Mercaptobenzoic acid 2-Mercaptobenzothiazole

HSC6H4COOH

m18

2-Mercaptoethanol

HSCH2CH2OH

m19

2-Mercaptoethyltriethoxysilane

HSCH2CH2Si(OC2H5)3

m17

Luminol, a153 2,6-Lupetidine, d591 -Lutidine, e212 Lutidines, d604, d605, d606, d607 Maleic hydrazide, d400 Malic acids, h180, h181

154.19

10, 125

167.25

27, 185

1.4220 4

78.13

1, 470

1.114320 4

1.500620

156.9

73

0.98820 4

1.43220

210

104

224.38

Malonaldehyde bis(dimethyl acetal), t91 Malonamide nitrile, c286 Malonic acid diamide, m4 Malonylurea, b1 Melamine, t198 Mellitic acid, b19

164–165

v s alc, HOAc

180–181 d

2 alc; 1 eth; 10 acet; 1 bz; s alk; i aq misc aq, alc, bz, eth

MEM chloride, m67 Menadione, m310 1,8-Mentanediamine, d41 p-Mentha-1,8-diene, d649 p-Mentha-6,8-dien-2-one, c20 Mercaptobenzene, t159

1.283

1.284

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m20 m21 m22 m23 m24 m25 m26 m27 m28 m29

m30 m31 m32 m33 m34

Formula weight

Beilstein reference

Density

Refractive index

HSCH2CH(OH)CH2OH

108.16

1, 519

1.29514 14

1.524320

CH3CH(SH)COOH

106.14

3, 289

1.22015 4

1.480920

HS(CH2)3Si(OCH3)3

196.34

1.03920 4

1.441620

HOOCCH2CH(SH)COOH

150.15

3, 439

70.09 85.11 86.09 67.91

1, 731 22, 399 2, 421 2, 423

0.830420 4

1.416020

1.015320 4 0.800120 4

1.431420 1.400720

104.54

22, 394

1.070

1.444720

16.04

1, 56

CH3SO3H (CH3SO2)2O

96.10 174.19

4, 4

0.4240bp 0.7168 g/L 1.481218 4

CH3SO2Cl

114.55

4, 5 1, 288 1, 273

Name 3-Mercapto-1,2propanediol 2-Mercaptopropionic acid (3-Mercaptopropyl)trimethoxysilane Mercaptosuccinic acid Methacrylaldehyde Methacrylamide Methacrylic acid Methacrylonitrile Methacryloyl chloride Methane

Methanesulfonic acid Methanesulfonic anhydride Methanesulfonyl chloride Methanethiol Methanol

Formula

H2C ¨ C(CH3)CHO H2C ¨ C(CH3)CONH2 H2C ¨ C(CH3)COOH H2C ¨ C(CH3)CN H2C ¨ C(CH3)COCl CH4

CH3SH CH3OH

48.11 32.04

Melting point

10

Boiling point

Flash point

Solubility in 100 parts solvent

1185mm

112

misc alc; v s acet

11716mm

87

misc aq, alc, eth, acet

9340mm

48

152–154

50 aq; 50 alc; s eth

81 69 109–111 16 163 35.8 90.3 95–96

15 76 12

6 aq; misc alc, eth s alc; sl s eth 9 aq; misc alc, eth 2.6 aq; misc acet, bz

2

182.5

161.5

1.430320

20 71

16710mm 13810mm

112

1.5 bz; misc aq v s aq(d)

1.480518 4

1.451820

32

161

110

s alc, eth

0.866520 4 0.791320 4

1.328420

123.0 97.7

6.0 64.7

11

2.3 aq; v s alc, eth misc aq, alc, bz, chl, eth

3.3 mL aq; 47 mL alc

m35 m36 m37

Methanol-d Methanol-d4 DL-Methionine

m38 m39

Methoxyacetic acid o-Methoxyacetophenone m-Methoxyacetophenone p-Methoxyacetophenone 2-Methoxyaniline 3-Methoxyaniline 4-Methoxyaniline 2-Methoxybenzaldehyde 4-Methoxybenzaldehyde 4-Methoxybenzamide

m40 m41 m42 m43 m44 m45 m46 m47 m48 m49 m50

Methoxybenzene 4-Methoxybenzenesulfonyl chloride 2-Methoxybenzoic acid

1.285

MES, m451 Mesidine, t330 Mesitol, t362 Mesitylene, t335 Mesityl oxide, m350 Mesoxylurea, a79

CH3OD CD3OD CH3SCH2CH2CH(NH2)COOH CH3OCH2COOH CH3OC6H4COCH3

33.05 36.07 149.21

13, 1186 13, 1187 42, 938

0.812720 4 0.888 1.340

1.327020 1.325620

90.08 150.18

3, 232 8, 85

1.174 1.09020 4

CH3OC6H4COCH3

150.18

8, 86

CH3OC6H4COCH3

150.18

CH3OC6H4NH2 CH3OC6H4NH2 CH3OC6H4NH2 CH3OC6H4CHO

110

65.5 65.4

11 11

1.415820 1.539320

202–204 13118mm

112 108

1.094

1.541020

239–241

110

8, 87

1.08241 4

1.533520

36–38

15426mm

123.16 123.16 123.16 136.15

13, 358 13, 404 13, 435 8, 43

1.09815 15 1.096 1.087 1.127

1.573020 1.579420 1.56020

5 1 60 35–36

225 251 243 236

117

i aq; misc alc, eth s alc, acid; sl s aq v s alc; sl s aq sl s alc, bz; i eth

CH3OC6H4CHO

136.15

8, 67

1.119

1.571320

1

248

108

misc alc

CH3OC6H4CONH2

151.17

102, 100

C6H5OCH3 CH3OC6H4SO2Cl

108.14 206.65

6, 138 11, 243

0.994220

CH3OC6H4COOH

152.15

10, 64

1.180

Mesyl chloride, m32 Metanilic acid, a119 Methacholine chloride, a49 Methacrolein, m24 Methallyl alcohol, m385 Methallyl chloride, c164

281 d

37.5 40–43

153.8

100

200

s aq v s alc, eth

98 112

164–167 295 1.517020

misc aq, alc, eth misc aq, alc, eth 3 aq; i eth; v sl s alc misc aq, alc, eth

51

s aq; v s alc; sl s eth 1 aq; misc alc, eth d aq; s alc, eth 0.5 aq; v s alc, eth

Methanal, f27 Methanoic acid, f32 Methenamine, h52 Methone, d508 4-Methoxy-2-butanone dimethyl acetal, t321

1.286

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m51 m52 m53 m54 m55 m56 m57 m58 m59 m60 m61 m62 m63 m64 m65

Name 3-Methoxybenzoic acid 4-Methoxybenzoic acid 4-Methoxybenzoyl chloride 4-Methoxybenzyl alcohol 4-Methoxybenzylamine 2-Methoxybiphenyl 3-Methoxy-1-butanol 4-Methoxy-3-buten2-one 1-Methoxy-1-buten3-yne 4-Methoxycinnamic acid 1-Methoxy-1,3-cyclohexadiene 1-Methoxy-1,4-cyclohexadiene 7-Methoxy-3,7-dimethyloctanal 2-Methoxy-1,3dioxolane 2-Methoxyethanol

Formula weight

Beilstein reference

CH3OC6H4COOH

152.15

10, 137

CH3OC6H4COOH

152.15

10, 154

CH3OC6H4COCl

170.60

10, 163

CH3OC6H4CH2OH

138.17

6, 897

CH3OC6H4CH2NH2

137.18

CH3OC6H4C6H5 CH3OCH(CH3)CH2CH2OH CH3OCH ¨ CHCOCH3

184.24 104.15

CH3OCH ¨ CHC ˜ CH

82.10

Formula

CH3OC6H4CH ¨ CHCOOH

(CH3)2C(OCH3)CH2CH2CH(CH3)CH2CHO

Refractive index

Melting point

Boiling point

Flash point

17210mm

s hot aq, alc, eth

185

275–280

0.04 aq; v s alc, chl

1.581020

22

14514mm

87

1.10925 4

1.544220

23–25

259

112

i aq(d); s alc(d); s bz, acet i aq; s alc, eth

13, 606

1.05015

1.546220

236–237

112

v s aq, alc, eth

6, 672

1.023 0.922920 20

1.610520 1.414520

274 161.1

112 46

misc aq

0.982

1.466020

200

63

0.90620 4

1.481820

122–125

8

1.3854

85

178.19

10, 298

110.16

63, 367

0.929

1.488520

4015mm

26

110.16

63, 367

0.940

1.481920

148–150

36

0.877

1.437420

600.45mm

98

194, 617

1.092

1.409120

129–130

31

1, 467

0.964620

1.402120

124.6

46

186.30

76.10

Solubility in 100 parts solvent

104

100.12

104.11 CH3OCH2CH2OH

Density

172–187

85.1

v s org solv s CCl4

misc aq

m66 m67 m68 m69 m70 m71 m72 m73 m74

m75 m76

2-(2-Methoxyethoxy)ethanol 2-Methoxyethoxymethyl chloride 2-Methoxyethyl acetate 2-Methoxyethylamine 1-Methoxy-2-indanol 2-Methoxy-5-methylaniline 3-Methoxy-4-methylaniline 4-Methoxy-2-methylaniline (4S,5S)-()-4Methoxymethyl-2methyl-5-phenyl-2oxazoline 4-Methoxy-4-methyl2-pentanone 1-Methoxynaphthalene

Methoxyethane, e171

CH3OCH2CH2OCH2CH2OH CH3OCH2CH2OCH2Cl

120.15

1.03520 4

1.426420

124.57

1.091

1.427020

CH3COOCH2CH2OCH3

118.13

2, 141

1.004920

1.402220

CH3OCH2CH2NH2

42, 718 6, 970 132, 388

0.864

1.405420 1.548220

CH3OC6H3(CH3)NH2

75.11 164.20 137.18

CH3OC6H3(CH3)NH2

137.18

13, 574

CH3OC6H3(CH3)NH2

137.18

132, 330

1.065

1.515520

205.26

(CH3)2C(OCH3)CH2COCH3 C10H7OCH3

130.18 158.20

1.564720

6, 606

0.906

1.418125

1.090

1.622020

2-Methoxyethoxychloromethane, m67

50

194.1

83

misc aq, alc, bz, eth, ketones

5013mm

112

65.1

144.5

43

misc aq

9 112

v s aq, alc

52–54

95 14611mm 235

51–54

250–252

13–14

248–249

s aq; v s alc, bz, eth 112

s alc

61

misc aq

790.05mm

13512mm

112

1.287

1.288

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m77

Name

Formula weight

Beilstein reference

C10H7OCH3

158.20

6, 640

72

CH3OC6H3(NO2)NH2

168.15

13, 390

138–140

CH3OC6H3(NO2)NH2

168.15

13, 389

CH3OC6H3(NO2)NH2

168.15

13, 521

CH3OC6H4NO2

153.14

6, 217

1.252720 4

CH3OC6H4NO2

153.14

6, 230

1.233

CH3OC6H3(NO2)COOH

197.15

10, 181

186–189

CH3OC5H3N(NO2)

154.13

212, 33

108–109

CH3OC6H3(NO2)CH3

167.16

6, 411

CH3OC6H4CH2CH2NH2

151.21

13, 626

CH3OC6H4OH

124.14

6, 768

Formula

m87

2-Methoxynaphthalene 2-methoxy-4-nitroaniline 2-Methoxy-5-nitroaniline 4-Methoxy-2-nitroaniline 2-Methoxynitrobenzene 4-Methoxynitrobenzene 4-Methoxy-3-nitrobenzoic acid 2-Methoxy-5-nitropyridine 4-Methoxy-2-nitrotoluene p-Methoxyphenethylamine 2-Methoxyphenol

m88

3-Methoxyphenol

CH3OC6H4OH

124.14

6, 813

m89 m90

4-Methoxyphenol 3-(4-Methoxyphenoxy)-1,2-propanediol

CH3OC6H4OH CH3OC6H4OCH2CH(OH)CH2OH

124.14 198.22

6, 843 63, 4411

m78 m79 m80 m81 m82 m83 m84 m85 m86

Density

Refractive index

1.207156

Melting point

Boiling point

Flash point

272

s bz, eth, CS2

117–119

s alc, hot bz, HOAc sl s aq; s alc, eth

123–126

1.207

1.561920

1.552520

9.4

277

54

260

17

1.537920 1.112 1.5429 (liquid) 1.131 1.551020

Solubility in 100 parts solvent

267

 112

0.17 aq; s alc, eth i aq; v s alc, eth

 112

13820mm 28

205

82

17.5

1155mm

 112

55–57 76–80

243

1.5 aq; misc alc, eth misc alc, eth; sl s aq v s bz; s alk

m91 m92 m93 m94

m95 m96 m97

m98 m99

m100 m101 m102

4-Methoxyphenylacetic acid o-Methoxyphenylacetone (o-Methoxyphenyl)acetonitrile 2-Methoxy-pphenylenediamine sulfate 1-Methoxy-2propanol 2-Methoxypropene trans-1-Methoxy-4(1-propenyl)benzene 2-Methoxy-4propenylphenol 2-Methoxy-4-(2propenyl)phenol

CH3OC6H4CH2COOH

166.18

10, 190

CH3OC6H4CH2COCH3

164.20

83, 397

CH3OC6H4CH2CN

147.18

10, 188

65–68

CH3OC6H3(NH2)2 · H2SO4

236.26

133, 1349

283 d

p-Methoxypropiophenone 2-Methoxypyridine 2-Methoxytetrahydrofuran

CH3OCH2CH(OH)CH3

90.1

CH3C(OCH3) ¨ CH2

72.11

86–88 1.054

1.525020

0.91920 20

1.402120

1, 435

0.753

1.382020 1.561520

1403mm 13010mm

97

i aq; v s alc; s eth 112

14315mm

s hot bz

120.1

38

34–36

18

21.4

237

90

CH3OC6H4CH ¨ CHCH3

148.21

6, 566

0.988320 4

CH3OC6H3(OH)CH ¨ CHCH3 CH3OC6H3(OH)CH2CH ¨ CH2

164.20

6, 955

1.08720 4

1.574820

10

266

112

164.20

6, 961

1.066420 4

1.540820

9.2

255

112

CH3OC6H4COCH2CH3

164.20

8, 103

1.071

1.546520

27–29

273–275

112

CH3OC5H4N

109.13 102.13

21, 44 174, 1019

1.038 0.972

1.502929 1.411920

142 105–107

32 7

-Methoxy--phenylacetophenone, b49

6-Methoxytetralin, m103

s alc, eth

Methoxy-1-tetralone, d358

misc aq, acet, bz, eth

misc chl, eth; 50 alc; s bz, EtAc misc alc, eth; sl s aq misc alc, chl, eth; s HOAc, alk; i aq

misc aq

1.289

1.290

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m103

m104 m105 m106 m107 m108 m109 m110 m111 m112 m113 m114 m115

m116 m117 m118

Name 6-Methoxy-1,2,3,4tetrahydronaphthalene 6-Methoxy-1tetralone 2-Methoxytoluene 3-Methoxytoluene 4-Methoxytoluene Methoxytrimethylsilane Methoxytripropylsilane N-Methylacetamide Methyl acetate

Formula weight

Beilstein reference

162.23

62, 537

176.22

92, 889

CH3OC6H4CH3 CH3OC6H4CH3 CH3OC6H4CH3 CH3OSi(CH3)3

122.17 122.17 122.17 104.2

6, 352 6, 376 6, 392

CH3OSi(C3H7)3

188.4

Formula

CH3CONHCH3 CH3COOCH3

Density

Refractive index

Melting point

1.540220

Boiling point 901mm

77–79

Flash point 112

17111mm

0.985115 15 0.969725 25 0.96925 25 0.756020 4

1.516120 1.513120 1.511220 1.367820

170–172 175–176 174 57–58

0.82220 4

1.42820

8312mm

51 54 53

73.10 74.08

4, 58 2, 224

0.946035 0.934220 4

1.425335 1.361920

30.6 98.1

206 56.3

16

Methyl acetoacetate p-Methylacetophenone Methyl acrylate Methylamine

CH3COCH2COOCH3 CH3C6H4COCH3

116.12 134.18

3, 632 7, 307

1.074720 1.0051

1.418620 1.532820

80 22–24

171.7 226

70 92

H2C ¨ CHCOOCH3 CH3NH2

86.09 31.06

2, 399 4, 32

0.956120 4 0.69911 4

1.411718

76.5 93.5

80.2 6.3

6 0

Methyl 2-aminobenzoate 2-(N-Methylamino)benzoic acid Methyl 3-aminocrotonate

H2NC6H4COOCH3

151.17

14, 317

1.6819 4

1.582020

24

256

104

CH3NHC6H4COOH

151.17

14, 323

CH3C(NH2) ¨ CHCOOCH3

115.13

3, 632

170–172 d 81–83

Solubility in 100 parts solvent

i aq; v s alc, eth s alc, bz, eth; i aq s alc, eth; i aq

s aq 24 aq; misc alc, eth 50 aq; misc alc i aq; v s alc, eth 6 aq; s alc, eth 959 mL aq; 10.5 bz; s alc; misc eth sl s aq; v s alc, eth 0.2 aq; s alc, eth

m119 m120 m121 m122 m123 m124 m125 m126 m127 m128 m129

2-(Methylamino)ethanol 4-Methylaminophenol sulfate 2-(Methylamino)pyridine N-Methylaniline N-Methylanilinium trifluoroacetate 2-Methylanthraquinone Methylarsonic acid 4-Methylbenzaldehyde Methyl benzenesulfonate 2-Methylbenzimidazole Methyl benzoate

0.93720

1.438720

CH3NHCH2CH2OH

75.11

4, 276

(CH3NHC6H4OH)2 · H2SO4 CH3NHC5H4N

344.39

13, 442

108.14

221, 629

1.05229 29

1.578520

15

201

87

s aq; v s alc, eth

C6H5NHCH3 C6H5NHCH3 · HOOCCF3

107.16 221.18

12, 135

0.98920 4

1.570420

57 65–66

196

73

sl s aq; s alc, eth

222.24

7, 809

177

subl

CH3AsO(OH)2 CH3C6H4CHO

139.96 120.15

4, 613 7, 297

1.019417 4

1.544720

C6H5SO2OCH3

172.20

112, 20

1.288904

1.515120

132.17

23, 145

136.15

9, 109

C6H5COOCH3

Methylal, d441 Methyl alcohol, m34 Methylaminoacetaldehyde dimethyl acetal, d442 -(1-Methylaminoethyl)benzyl alcohols, e1, e2

155–156

72

260 d

4 aq; sl s alc; i eth

v s bz; s alc, eth

161 205 4

80

15420mm

176–177 1.093315 4

2-Methyl-p-anisidine, m71 4-Methyl-m-anisidine, m72 5-Methyl-o-anisidine, m73 Methylanisoles, m105, m106, m107 Methyl anthranilate, m116

1.520515

12.1

misc aq, alc, eth

199.5

82

v s aq; s alc misc alc, eth; sl s aq v s alc, chl, eth s alk, hot aq; sl s alc 0.2 aq; misc alc, eth

Methylanthranilic acids, a211, a212 N-Methylanthranilic acid, m117 Methylbenzene, t167 4-Methylbenzenesulfonic acid, t176

1.291

1.292

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m130 m131 m132 m133 m134 m135 m136 m137 m138 m139 m140 m141 m142 m143 m144

Name 2-Methylbenzoic acid 3-Methylbenzoic acid 4-Methylbenzoic acid 2-Methylbenzophenone 4-Methylbenzophenone 2-Methylbenzothiazole 5-Methyl-1 H-benzotriazole 2-Methylbenzoxazole -Methylbenzyl alcohol 3-Methylbenzyl alcohol 4-Methylbenzyl alcohol DL--Methylbenzylamine 4-Methylbenzylamine Methyl bromoacetate DL-Methyl2-bromobutyrate

Formula weight

Beilstein reference

Density

CH3C6H4COOH

136.15

9, 462

1.062

107–108 258–259

sl s aq; v s alc

CH3C6H4COOH

136.15

9, 475

1.054

111–113 263

0.09 aq; v s alc

CH3C6H4COOH

136.15

9, 483

180–182 274–275

v s alc, eth

CH3C6H4COC6H5

196.25

7, 439

CH3C6H4COC6H5

196.25

7, 440

149.22

27, 46

133.15

26, 58

133.15

27, 46

1.121

1.549720

C6H5CH(CH3)OH

122.17

6, 475

1.019113 4

CH3C6H4CH2OH

122.17

6, 494

0.91617

CH3C6H4CH2OH

122.17

6, 498

C6H5CH(CH3)NH2

121.18

12, 1094

0.940

1.525420

CH3C6H4CH2NH2 BrCH2COOCH3 CH3CH2CH(Br)COOCH3

121.18 152.98 181.04

12, 1141 2, 213 2, 282

0.952 1.616 1.573

1.534020 1.458620

Formula

1.083

1.173

Refractive index

Melting point

Boiling point

Flash point

18

309–311

59–60

326

12–14

238

80–82 8.5–10

210– 21212mm 178 75

1.521120

21

204

1.533420

20

217

5 aq; s alc, eth

59–61

217

s alc, eth; sl s aq

1.595820

1.617020

185 12–13

112

Solubility in 100 parts solvent

v s alc, org solv v s bz, eth

102

85

s alc, HOAc; i aq

v s alc; s bz, chl

79

195 75 5215mm 62 137– 13850mm

s alc

m145 m146 m147 m148 m149 m150 m151 m152 m153 m154 m155

Methyl 4-bromocrotonate Methyl 2-bromopropionate 2-Methyl-1,3butadiene 3-Methyl-1,2butadiene 2-Methylbutane 2-Methyl-1butanethiol 2-Methyl-2butanethiol 3-Methyl-1butanethiol 2-Methyl-1butanol 2-Methyl-2butanol 3-Methyl-1butanol

1.522

1.498020

8513mm

91

2, 253

1.497

1.542020

5119mm

51

s alc

68.12

1, 252

0.68120 4

1.421620

145.9

34. 1

53

misc alc, eth

CH3C(CH3) ¨ C ¨ CH2

68.12

1, 252

0.69420 4

1.417920

113.6

40.9

12

CH3CH2CH(CH3)2 CH3CH2CH(CH3)CH2SH

72.15 104.22

1, 134 12, 421

0.619720 0.848

1.353720 1.446520

159.9

27.9 119.0

56 19

0.005 aq; misc alc s alc, eth; i aq

CH3CH2C(CH3)2SH

104.22

11, 196

0.842

1.438520

103.9

99.1

1

s alc, eth; i aq

104.22

1, 405

0.83520 4

1.443220

133.5

118.4

18

misc alc, chl, eth

CH3CH2CH(CH3)CH2OH

88.15

1, 388

0.81620 4

1.410020

70

128

50

3 aq; misc alc, eth

CH3CH2C(CH3)2OH

88.15

1, 388

0.809020

1.405020

9.0

102.0

21

(CH3)2CHCH2CH2OH

88.15

1, 392

0.812915 4

1.408515

117.2

132.0

45

11 aq; misc alc, bz, chl, eth 2 aq; misc alc, bz, chl, eth, PE, HOAc

BrCH2CH ¨ CHCOOCH3

179.02

CH3CH(Br)COOCH3

167.01

H2C ¨ C(CH3)CH ¨ CH2

(CH3)2CHCH2CH2SH

-Methylbenzyl alcohol, p112 N-Methylbenzylamine, b103 Methylbenzyl bromides, b368, b369

Methylbenzyl chlorides, c258, c259, c260 Methylbis(2-chloroethoxy)silane, b157 N-Methylbis(2-chloroethyl)amine, b159

Methyl bromide, b300 3-Methyl-1-buten-1-carboxylic acid, m349

1.293

1.294

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m156

Name

m167 m168

3-Methyl-2butanol 3-Methyl-2butanone 2-Methyl-1-butene 2-Methyl-2-butene 3-Methyl-1-butene (E)-2-Methyl-2butenoic acid (Z)-2-Methyl-2butenoic acid 3-Methyl-2-butenoic acid 2-Methyl-3-buten2-ol 3-Methyl-3-buten1-ol 2-Methyl-1-buten3-yne N-Methylbutylamine 1-Methylbutylamine

m169

2-Methylbutylamine

m170

3-Methylbutyl3-methylbutyrate 3-Methyl-1-butyne 2-Methyl-3-butyn-2-ol

m157 m158 m159 m160 m161 m162 m163 m164 m165 m166

m171 m172

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

(CH3)2CHCH(OH)CH3

88.15

1, 391

0.817920

1.409620

(CH3)2CHCOCH3

86.13

1, 682

0.80220 4

1.3890

92

94–95

CH3CH2C(CH3) ¨ CH2 CH3CH ¨ C(CH3)2 (CH3)2CHCH ¨ CH2 CH3CH ¨ C(CH3)COOH

70.14 70.14 70.14 100.12

1, 211 1, 211 13, 797 2, 430

0.650420 4 0.662020 4 0.627220 4 0.969

1.377720 1.387820 1.363820 1.434281

137.6 133.8 168.5 64

31.2 38.6 20.1 198.5

CH3CH ¨ C(CH3)COOH

100.12

2, 428

0.98347 4

1.443747

45

185

(CH3)2C ¨ CHCOOH

100.12

2, 432

1.00624

69

194–195

(CH3)2C(OH)CH ¨ CH2

86.13

1, 444

0.867220 20

1.416020

2.6

98–99

H2C ¨ C(CH3)CH2CH2OH

86.13

0.853

1.433720

H2C ¨ C(CH3)C ˜ CH

66.10

11, 126

CH3CH2CH2CH2NHCH3 CH3CH2CH2CH(CH3)NH2 CH3CH2CH(CH3)CH2NH2 (CH3)2CHCH2CH2OOCCH2CH(CH3)2 (CH3)2CHC ˜ CH (CH3)2C(OH)C ˜ CH

87.17 87.17

4, 157 4, 177

87.17

111.5

Flash point 26

45

Solubility in 100 parts solvent 2.8 aq; misc alc, eth misc alc, eth misc alc, eth misc alc, eth; i aq misc alc, eth s alc, eth; v s hot aq s alc, eth; v s hot aq s aq, alc, eth

13 36

1.414020

113

32

6

0.736 0.738420 4

1.399520 1.402920

75

91 91

1 35

43, 342

0.738

1.411620

94–97

3

172.27

2, 312

0.854125

1.410025

194.0

68.12 84.12

1, 251 11, 235

0.66620 4 0.867220 20

1.374020 1.420920

89.8 2.6

26.4 104–105

misc aq, alc, eth

misc alc, eth

25

misc alc, eth misc aq, acet, bz

m173 m174 m175 m176 m177 m178 m179 m180 m181 m182

2-Methylbutyraldehyde 3-Methylbutyraldehyde Methyl butyrate 2-Methylbutyric acid 3-Methylbutyric acid 3-Methylbutyronitrile 3-Methylbutyryl chloride l-(3-Methylbutyryl)pyrrolidine Methyl carbamate Methyl chloroacetate

CH3CH2CH(CH3)CHO

86.13

11, 352

0.804

1.391920

(CH3)2CHCH2CHO

86.13

1, 684

0.78520 20

1.388220

CH3CH2CH2COOCH3

102.13

24, 786

0.89820 4

1.387920

CH3CH2CH(CH3)COOH

102.13

24, 888

0.936

1.405520

(CH3)2CHCH2COOH

102.13

2, 309

0.930820 4

1.403320

83.13

22, 278

0.792519 4

1.392720

120.58

2, 315

0.98520 4

1.416120

0.938

1.471020

(CH3)2CHCH2CN (CH3)2CHCH2COCl

155.24 H2NCOOCH3 ClCH2COOCH3

(Z)-2-Methyl-2-butenedioic acid, c270 Methyl 2-buten-1-oate, m192 3-Methylbutyl acetate, i80 2-Methylbutylamine, a251 Methyl tert-butyl ether, b460 Methyl tert-butyl ketone, h72

75.07

3, 21

1.13656 4

108.52

2, 197

1.23820 20

2-Methylbutyl isovalerate, m170 Methyl caprate, m218 Methyl caproate, m265 Methyl carprylate, m329 Methyl carbazate, m271 Methyl carbitol, m66

1.422020

90–92

4

51

92–93

19

85

102

14

176.5

112

30.0

176.5

70

101

129 115–117

misc alc, eth; sl s aq 1.4 aq; misc alc, eth

4 aq; s alc, chl, eth misc alc, eth

18

d aq, alc; s eth

104 52–54

177

33

130–132

57

4-Methylcatechol, d389 Methyl Cellosolve, m65 Methyl Cellosolve acetate, m68 -Methylchalcone, d658 Methyl chlorocarbonate, m187

220 aq; 73 alc; s eth i aq; misc alc, eth

1.295

1.296

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m183 m184 m185 m186 m187 m188 m189 m190 m191 m192 m193 m194 m195 m196

m197 m198

Name Methyl 2-chloroacetoacetate Methyl m-chlorobenzoate Methyl p-chlorobenzoate Methyl 4-chlorobutyrate Methyl chloroformate Methyl 3-(chloroformyl)propionate Methyl 2-chloropropionate 2-Methylcinnamaldehyde 6-Methylcoumarin Methyl crotonate Methyl cyanoacetate Methylcyclohexane Methyl cyclohexanecarboxylate 4-Methyl-1,2-cyclohexanedicarboxylic anhydride 1-Methylcyclohexanol (Z )-2-Methylcyclohexanol

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

1.236

1.446520

32.7

137

1.492320

21

10112mm

Flash point

Solubility in 100 parts solvent

CH3COCH(Cl)COOCH3

150.56

ClC6H4COOCH3

170.60

9, 338

ClC6H4COOCH3

170.60

9, 340

1.38220

ClCH2CH2CH2COOCH3

136.58

2, 278

1.126814

1.432120

176

59

v s eth; s alc, acet

3, 9

1.22320 4

1.386520

71

1

misc alc, bz, chl, eth

ClCOOCH3

94.50

71

44

s alc

CH3OOCCH2CH2COCl

150.56

22, 553

1.223

1.440220

653mm

73

CH3CH(Cl)COOCH3

122.55

2, 248

1.075

1.419320

132–133

36

C6H5CH ¨ C(CH3)CHO

146.19

7, 369

1.04717 4

1.604520

14927mm

79

CH3CH ¨ CHCOOCH3 NCCH2COOCH3 C6H11CH3 C6H11COOCH3

160.17 100.12 99.09 98.19 142.20

17, 337 2, 410 2, 584 5, 29 9 1, 5

0.944420 4 1.122525 0.769420 0.995416 4

1.424220 1.416625 1.423120 1.444520

303725mm 121 205.1 100.9 183

4 110 3 60

v s alc, eth; i aq misc alc, eth

1.162

1.477420

168.19

75–76 13.1 126.6

s alc

i aq; s alc, eth

C6H10(CH3)OH

114.19

6, 11

0.925125

1.458725

26

168

67

i aq; s bz, chl

C6H10(CH3)OH

114.19

62, 17

0.934020 4

1.465420

7

165

58

misc alc, eth

m199 m200 m201 m202 m203 m204 m205 m206 m207 m208 m209

(E)-2-Methylcyclohexanol (Z)-3-Methylcyclohexanol (E)-3-Methylcyclohexanol (Z)-4-Methylcyclohexanol (E)-4-Methylcyclohexanol 2-Methylcyclohexanone 3-Methylcyclohexanone 4-Methylcyclohexanone 1-Methyl-1-cyclohexene 4-Methyl-1-cyclohexene N-Methylcyclohexylamine

Methyl chloroform, t226

C6H10(CH3)OH

114.19

6, 11

0.924720 4

1.461620

4

165.5

58

misc alc; s eth

C6H10(CH3)OH

114.19

6, 12

0.915520

1.457220

6

94

62

misc alc, eth

C6H10(CH3)OH

114.19

6, 12

0.921420

1.458020

1

84

62

CH3C6H10OH

114.19

6, 14

0.912220 4

1.461420

171

70

misc alc, eth

CH3C6H10OH

114.19

6, 14

0.911821 4

1.455920

173–175

70

misc alc; s eth

CH3C6H9( ¨ O)

112.17

7, 14

0.92520 4

1.447820

162–163

46

i aq; s alc, eth

CH3C6H9( ¨ O)

112.17

7, 15

0.915520 4

1.446020

168–169

51

i aq; s alc, eth

CH3C6H9( ¨ O)

112.17

7, 18

0.91620 4

1.445520

169–171

40

i aq; s alc, eth

96.17

5, 66

0.80920 4

1.450220

121

111

3

i aq; s alc, eth

96.17

5, 67

0.799

1.441220

115.5

102

1

i aq; s alc, eth

113.20

12, 6

0.868

1.456020

149

29

C6H11NHCH3

(E)-2-Methylcrotonic acid, m161

1.297

1.298

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m210 m211 m212 m213 m214 m215 m216 m217

m218 m219 m220

m221 m222 m223

Formula weight

Beilstein reference

Density

Refractive index

C6H10(CH3)NH2

113.20

12, 10

0.855

1.452520

150730mm

22

C6H10(CH3)NH2

113.20

12, 12

0.855

1.453120

151–154

26

0.941

1.497620

51

200

26

Name 3-Methylcyclohexylamine 4-Methylcyclohexylamine Methylcyclopentadiene dimer Methylcyclopentane 3-Methyl-1,2-cyclopentanedione 2-Methylcyclopentanone 3-Methyl-2-cyclopenten-1-one 2-Methylcyclopropanecarboxylic acid Methyl decanoate Methyl dichloroacetate Methyl 2,2-dichloro1-methylcyclopropanecarboxylate Methyl 2,3-dichloropropionate Methyldichlorosilane N-Methyldiethanolamine

Formula

160.26 C5H9CH3

CH3(CH2)8COOCH3 Cl2CHCOOCH3

Melting point

Boiling point

Flash point

84.16 112.13

5, 27 71, 310

0.748720

1.409720

142.4 71.8 105–107

98.15

72, 13

0.920020 4

1.434720

76

96.13

71, 46

0.971

1.478020

7415mm

65

100.12

9, 6

1.027

1.439520

191745mm

87

186.30 142.97

2, 356 2, 203

1.380819

1.442120

223–224 143

80

1.245

1.463920

748mm

74

1.328220 4

1.444720

9250mm

42

1.104720 4

1.422220

41

25

1.037720

1.468520

246–248

126

183.03

ClCH2CH(Cl)COOCH3

157.00

CH3SiHCl2

115.0

CH3N(CH2CH2OH)2

119.16

21, 111

4, 284

18 52

93

27

139–140

Solubility in 100 parts solvent

0.013 aq

s aq; v s alc, eth

i aq; misc alc, eth i aq; s alc

s alc

misc aq, alc

m224 m225 m226

m227 m228 m229 m230 m231 m232 m233

O-Methyl-N,Ndiisopropylurea Methyl 3,4-dimethoxybenzoate Methyl 4,5-dimethoxy-2-nitrobenzoate Methyl 2,2-dimethylpropionate 2-Methyl-3,5-dinitrobenzoic acid N-Methyldioctylamine N-Methyldiphenylamine Methyldiphenylsilane N,N-Methylenebisacrylamide 2,2-Methylenebis(4-chlorophenol)

(CH3)2CHNHC(OCH3) ¨ NCH(CH3)2 (CH3O)2C6H3COOCH3

158.25

0.871

1.435820

196.20

10, 396

57–60

(CH3O)2C6H2(NO2)COOCH3

241.20

10, 403

141–144

(CH3)3CCOOCH3

116.16

21, 139

CH3C6H2(NO2)2COOH

226.15

9, 474

(C8H17)2NCH3

255.49

43, 381

(C6H5)2NCH3

183.26

12, 180

(C6H5)2Si(H)CH3

198.3

H2C ¨ CHCONHCH2NHCOCH ¨ CH2 CH2[C6H3(Cl)OH]2

154.17

 300

269.13

177–178

Methyl 4,6-dimethyl-2-oxo-2H-pyran-5carboxylate, m288

0.873

1.388020

50– 520.1mm 283

35

101–103

1

misc alc, eth; sl s aq

205–207 1.442420

30.1

16515mm

1.04820 4

1.619320

7.6

1356mm

0.99720 4

1.56920

Methyldinitrophenols, d631, d633a Methyl enanthate, m261

Methylene bromide, d88

i aq; s alc, eth

100 EtOH; 100 eth; s PE

1.299

1.300

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m234

m235

m236 m237 m238 m239 m240 m241 m242 m243

m244 m245 m246

Name 4,4-Methylenebis(N,N-dimethylaniline 4,4-Methylenebis(3-hydroxy-2naphthoic acid 1,1-Methylenebis(3methylpiperidine) Methylene blue 4,4-Methylenedianiline 3,4-Methylenedioxybenzaldehyde 1,2-Methylenedioxybenzene 3,4-Methylenedioxybenzoic acid 3,4-Methylenedioxybenzyl alcohol 3,4-Methylenedioxy6-propylbenzyldiethyleneglycol butyl ether 5-Methylene-2-norbornene Methylenesuccinic acid N-Methylethylamine

Formula weight

Beilstein reference

CH2[C6H4N(CH3)2]2

254.38

13, 239

90

CH2[C10H5(OH)COOH]2

388.38

10, 575

d  280

CH2(CH3C5H9N)2

210.37

CH2(C6H4NH2)2

373.90 198.26

27, 393 13, 238

190 d 92

150.13

19, 115

37

122.12

19, 20

166.13

19, 269

229

152.14

19, 67

53–55

Formula

H2C ¨ C(COOH)CH2COOH CH3CH2NHCH3

Density

0.887

1.064

Refractive index

1.473420

1.05

1.5020

106.17

0.981

1.481920

2, 760

1.573

59.11

42, 589

0.690

Boiling point

Flash point

110 4 aq; 1.3 alc; s chl 221

264 173

0.2 aq; v s alc, eth 55

subl 210

1801mm

sl s aq, chl, alc, eth

171

misc alc, bz, freons

4 162 d

1.3760

Solubility in 100 parts solvent

i aq, alc, eth, bz; sl s chl; s pyr 16050mm

1.5398

338.45

130.10

Melting point

35

12

8.2 aq; 20 alc; v s bz, chl, eth, PE v s aq, alc

m247 m248 m249 m250 m251 m252 m253 m254

N-Methylethylenediamine N-Methylformamide N-Methylformanilide Methyl formate 5-Methylfuraldehyde 2-Methylfuran Methyl furoate Methylgermanium tribromide

Methylene bromochloride, b256 Methylene chloride, d190 4,4-Methylenedianiline, d35 Methylene dimethyl ether, d441 Methylene iodide, d404

CH3NHCH2CH2NH2 HCONHCH3 C6H5N(CH3)CHO HCOOCH3

CH3GeBr3

74.13

41, 415

0.841

1.439520

59.07 135.17 60.05 110.11

4, 58 12, 234 2, 18 17, 289

0.998825 1.095 0.981515 1.107218 4

1.430025 1.559320 1.346515 1.526320

82.10 126.11 327.35

17, 36 18, 274

0.91520 4 1.17920 2.633720 4

1.433220 1.486220 1.577020

1,1-Methylenedipiperidine, d695 -Methylene--propiolactone, d422 (E)-3,6-endo-Methylene-1,2,3,6tetrahydronaphthaloyl dichloride, n109 Methyl ethyl ketone, b393

114–116

41

3.8 8–13 99.0

180–185 244 31.5 187

98 126 32 72

88

63–66 181 168

26 73

misc aq 23 aq; misc alc s aq; v s alc; misc eth 0.3 aq s alc, eth; sl s aq

Methyl fluoroform, t291 Methyl 2-furancarboxylate, m253 5-Methylfurfural, m251 -Methyl-D-glucopyranoside, m256

1.301

1.302

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m255

Name

m264 m265 m266

N-Methyl-Dglucamine -Methylglucoside DL-2-Methylglutaronitrile N-Methylglycine Methyl glycolate 2-Methylheptane Methyl heptanoate 6-Methyl-5-hepten2-one Methyl hexadecanoate 2-Methylhexane Methyl hexanoate 5-Methyl-2-hexanol

m267

5-Methyl-2-hexanone

m256 m257 m258 m259 m260 m261 m262 m263

m268

5-Methyl-3-hexen2-one m268a 1-Methylhexylamine m269 1-Methylhydantoin m270 Methylhydrazine m271 Methyl hydrazinocarboxylate m272 Methyl hydrogen glutarate

Formula

Formula weight

Beilstein reference

Density

Refractive index

195.22 31, 179 2, 656

1.4630 4 0.950

CH3NHCH2COOH HOCH2COOCH3 CH3(CH2)4CH(CH3)2 CH3(CH2)5COOCH3 (CH3)2C ¨ CHCH2CH2COCH3 CH3(CH2)4COOCH3

89.09 90.08 114.23 144.22 126.20

4, 345 3, 236 1, 161 2, 339 12, 797

1.16818 4 0.697820 4 0.881520 4 16 0.8554

270.46

2, 372

CH3(CH2)3CH(CH3)2 CH3(CH2)4COOCH3 (CH3)2CHCH2CH2CH(OH)CH3 (CH3)2CHCH2CH2COCH3 (CH3)2CHCH ¨ CHCOCH3

100.21 130.19 116.20

1, 156 2, 323 1, 416

0.678620 0.903804 0.81420 4

1.384920 1.403823 1.417620

114.19

12, 756

0.88820 4

1.406220

H(CH2)5CH(NH2)CH3

115.22 114.10 46.07 90.08

4, 194 24, 244 42, 957 31, 46

0.766518 0.866

1.423520

146.14

22, 565

1.169

1.438120

CH3NHNH2 H2NNHCOOCH3 HOOCCH2CH2CH2 COOCH3

Boiling point

Flash point

128–129

194.19 108.14

NCCH2CH2CH(CH3)CN

Melting point

168

1.397420 1.411520 1.439220

Solubility in 100 parts solvent 100 aq; 1.2 alc

2000.2mm 12510mm

63 aq; i alc, eth 126

d 212 74 109.0 55.8 67

151 117.7 173.8 7318mm

28

19615mm

118.3 71

90.1 151 150

3 54 46

s alc; misc eth v s alc, eth s alc, eth; i aq

141

41

0.5 aq; misc alc, eth

144 subl 87.5 10812mm

54

sl s aq; s alc, eth s aq, alc; 3 eth misc aq, alc; s PE

4 52 50

42 aq; sl s alc s aq; misc alc, eth s eth; sl s alc s alc, eth; sl s aq misc alc, eth s alc, chl, eth

1.440020

112.17

1.417520 157 52.4 70–73

15110mm

21 112

m273 m274 m275 m276 m277 m278 m279 m280 m281 m282

Methyl hydrogen hexanedioate Methyl hydrogen succinate Methyl hydroperoxide Methylhydroquinone Methyl 4-hydroxybenzoate Methyl 2-hydroxyisobutyrate Methyl 4-hydroxyphenylacetate 1-Methylimidazole 2-Methylimidazole 4-Methylimidazole

HOOC(CH2)4COOCH3

160.17

2, 652

HOOCCH2CH2COOCH3

132.12

2, 608

48.04

12, 270

HOC6H4COOCH3

124.14 152.15

6, 874 10, 158

(CH3)2C(OH)COOCH3

118.13

32, 223

HOC6H4CH2COOCH3

166.18

10, 191

82.11 82.11 82.11

23, 46 23, 65 23, 69

CH3OOH

N-Methylguanidine acetic acid, c277 4-Methylhexahydrophthalic anhydride, m196 Methyl hydroxyacetate, m259

1.081

1.99715 4

1.440120

112

8–9

16210mm

56–59

15120mm

v s aq, alc, eth

3865mm

misc aq, alc, eth; s bz

1.364215

125–128 126–128 270 d 1.023

1.411220 57–60

1.030

1.497020

Methyl 4-hydroxy-3-methoxybenzoate, m445 Methyl 2-hydroxypropionate, m291 2,2-Methyliminodiethanol, m223

60 143 46–48

s alc

v s alc, eth, acet

137

42

v s aq, alc

162– 1635mm 198 268 263

92

misc aq

112

2,2-Methyliminobis(acetaldehyde diethyl acetal), b169

1.303

1.304

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density 1.0720 4

m283

2-Methyl-1H-indole

131.18

20, 311

m284 m285

3-Methyl-1H-indole N-Methylisatoic anhydride Methyl isobutyrate

131.18 177.16

20, 315 27, 265

(CH3)2CHCOOCH3

102.13

2, 290

0.89120

Methyl isocyanate Methyl isodehydacetate Methyl isothiocyanate 5-Methylisoxazole Methyl lactate

CH3NCO

57.05 182.18

4, 77 18, 410

CH3NCS

73.12

CH3CH(OH)COOCH3

Methyl mandelate Methyl mercaptoacetate Methyl 3-mercaptopropionate Methylmercury chloride Methyl methacrylate Methyl methanesulfonate Methyl methoxyacetate

m286 m287 m288 m289 m290 m291 m292 m293 m294 m295 m296 m297 m298

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

58–60

273

95 165 d

266

1.384020

84

93

1

0.967

1.369520

17 60–63

37–39 16714mm

18

misc alc, eth; sl s aq s aq

4, 77

1.069

1.525837

35–36

119

32

v s alc, eth; sl s aq

83.09 104.10

27, 16 3, 280

1.018 1.08820 4

1.438620 1.413120

~66

122 144.8

30 52

C6H5CH(OH)COOCH3 HSCH2COOCH3

166.18 106.14

10, 202

1.175620 1.187

1.465720

13512mm 4310mm

30

HSCH2CH2COOCH3

120.17

32, 214

1.085

1.464020

5514mm

60

CH3HgCl

251.10

H2C ¨ C(CH3)COOCH3

100.12

22, 398

0.943320

1.414620

100.3

10

CH3SO2OCH3

110.13

4, 4

1.294320 4

1.413820

202–203

104

1.6 aq; s ketones, esters, CCl4 20 aq; 100 DMF

CH3OCH2COOCH3

104.11

3, 236

1.051120 4

1.396420

130

35

v s alc, eth; sl s aq

51–54

4.0625

v s alc, eth; s hot aq s hot aq, alc, bz

misc aq(d), alc, eth s aq, alc, bz, chl s alc, eth

170 48.2

m299

m300 m301 m302 m303

Methyl 1-methoxybicyclo[2.2.2]oct5-ene-2-carboxylate Methyl 4-methoxyphenylacetate 1-Methyl-4-(methylamino)piperidine Methyl 3-methylbutyrate 2-Methyl-6-methylene-2-octanol

Methyl iodide, i40 Methyl isoamyl ketone, m267 Methyl isobutenyl ketone, m350 Methyl isobutyl ketone, m346 Methyl isonicotinate, m402 Methyl isopentyl ketone, m267

196.25

CH3OC6H4CH2COOCH3

180.20

10, 191

128.22 (CH3)2CHCH2COOCH3

116.16

C2H5C( ¨ CH2)(CH2)3C(CH3)2OH

156.27

22, 274

1.086

1.488620

10517mm

103

1.135

1.516520

15819mm

36

0.882

1.467220

0.88120 4

1.380025

116–117

0.784

1.443120

8410mm

Methyl isovalerate, m302 2-Methyllactic acid, h127 Methyl linoleate, m325 Methyl mercaptan, m33 Methylmercaptoanilines, m422, m423 4-Methylmercaptobenzaldehyde, m424

55 sl s aq; misc alc, eth 76

Methylmercaptophenols, m431a, m429 7-Methyl-3-methylene-1,6-octadiene, m453 1-Methyl-4-(1-methylethenyl)cyclohexane, d649 5-Methyl-2-(1-methylethyl)cyclohexanol, m12 5-Methyl-2-(1-methylethyl)cyclohexanone, m13

1.305

1.306

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m304

Density

Refractive index

140.14

1.116

1.473020

7520mm

63

CH3S( ¨ O)CH2SCH3

124.22

1.191

1.548720

952.5mm

112

CH3SCH2CH2COOCH3

134.20

1.077

1.465020

7513mm

72

C10H7CH3 C10H7CH3

101.15 142.20 142.20 172.18

27, 6 5, 566 5, 567 72, 656

0.920 1.02514 4 1.02920 4

1.434920 1.615920 1.602640

66 116 30.5 244.7 34.6 241.4 105–107

23 82

C10H7COCH3

170.21

7, 401

1.133604

1.628420

12

296–298

s alc, eth; i aq

C10H7COCH3

170.21

7, 402

53–55

300–301

sl s alc; s CS2

CH3ONO2

77.04

1, 284

1.207520 4

83.0

sl s aq; s alc, eth

61.04

1, 284

0.991 (liquid) 1.586140 4

64 explodes 17.35

Name

Formula

Formula weight

Beilstein reference

m313

Methyl 2-methyl3-furancarboxylate Methyl S-methylthiomethyl sulfoxide Methyl 3-(methylthio)propionate N-Methylmorpholine 1-Methylnaphthalene 2-Methylnaphthalene 2-Methyl-1,4naphthoquinone Methyl 1-naphthyl ketone Methyl 2-naphthyl ketone Methyl nitrate

m314

Methyl nitrate

CH3ONO

m315

2-Methyl-4-nitroaniline 2-Methyl-5-nitroaniline 4-Methyl-2-nitroaniline Methyl 2-nitrobenzoate

CH3C6H3(NO2)NH2

152.15

12, 846

CH3C6H3(NO2)NH2

152.15

CH3C6H3(NO2)NH2 O2NC6H4COOCH3

m305

m306 m307 m308 m309 m310 m311 m312

m316 m317 m318

1.374820

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

s aq, alc, eth v s alc, eth v s alc, eth 1.4 alc; 10 bz; s chl

s alc, eth

131–133

v s alc; s bz

12, 844

104–107

s alc, acet, eth

152.15

12, 100

115–116

v s alc; s eth

181.15

9, 372

1.280

1.535020

13

1060.1mm

112

s alc, eth

m319 m320 m321 m322 m323 m324 m325 m326 m327 m328

2-Methyl-3-nitrobenzoic acid 4-Methyl-3-nitrobenzoic acid 5-Methyl-2-nitrobenzoic acid 2-Methyl-5-nitroimidazole 3-Methyl-2-nitrophenol 4-Methyl-2-nitrophenol Methyl 9,12-octadecadienoate Methyl octadecanoate Methyl cis-9-octadecenoate Methyloctadecyldichlorosilane

CH3C6H3(NO2)COOH

181.15

9, 471

182–184

CH3C6H3(NO2)COOH

181.15

9, 502

187–190

CH3C6H3(NO2)-COOH

181.15

9, 482

134–136

127.10

231, 23

252–254

CH3C6H3(NO2)OH

153.14

6, 385

35–39

CH3C6H3(NO2)OH

153.14

6, 412

CH3(CH2)4CH ¨ CHCH2CH ¨ CH(CH2)7COOCH3 CH3(CH2)16COOCH3

294.46

CH3(CH2)7CH ¨ CH(CH2)7COOCH3 C18H37Si(CH3)Cl2

Methyl 2-methyllactate, m278 Methyl methyl-2-propenoate, m296 Methyl methylsulfinylmethyl sulfide, m305

298.51

2, 379

296.50

2, 467

367.5

1.24020 4

1.57440

32–35

12522mm

v s alc, eth

0.888618 4

1.459325

35

21216mm

misc DMF

38–39

21515mm

19.9

1682mm

0.87918 4 0.93020 4

Methyl myristate, m413 Methyl nicotinate, m404 4-Methyl-3-nitroanisole, m85

1.452120

 112

1852.5mm

Methyl 6-nitrovertrate, m226 Methyl nonyl ketone, u5 Methyl oleate, m327

s alc, eth misc abs alc, eth

1.307

1.308

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m329 m330 m331 m332 m333 m334 m335 m336 m337 m338 m339 m340 m341 m342 m343

Name

Formula

Formula weight

Beilstein reference

158.24 227.3

2, 348

Methyl octanoate Methyloctyldichlorosilane 3-Methyl-2-oxazolidinone 2-Methyl-2-oxazoline Methyl 2-oxocyclopentanecarboxylate Methyl 2-oxopropionate Methyl 2-oxo-1pyrrolidineacetate 2-Methylpentane 3-Methylpentane

CH3(CH2)6COOCH3 C8H17Si(CH3)Cl2

CH3CH2CH2CH(CH3)2 (CH3CH2)2CHCH3

86.18 86.18

2-Methyl-2,4pentanediol 4-Methylpentanenitrile Methyl pentanoate

(CH3)2C(OH)CH2CH(OH)CH3 (CH3)2CHCH2CH2CN

2-Methylpentanoic acid 3-Methylpentanoic acid 2-Methyl-1-pentanol

101.11

Density

Refractive index

Melting point

Boiling point

Flash point

0.877520 4 0.97620 4

1.416025 1.44420

40

192.9 946mm

1.170

1.454120

15

20

v s alc, eth; i aq  112

85.11

27, 11

1.005

1.434020

87– 901mm 110

142.15

10, 597

1.145

1.456020

10519mm

 112

102.09

3, 616

1.130

1.406520

134–137

39

1.131

1.471920

1, 148 1, 149

0.653220 0.664320

1.372520 1.376520

118.18

1, 486

0.921620 4

1.427020

97.16

22, 290

0.803520 4

1.406120

CH3(CH2)3COOCH3

116.16

2, 301

0.875

1.396220

CH3CH2CH2CH(CH3)COOH CH3CH2CH(CH3)CH2COOH CH3CH2CH2CH(CH3)CH2OH

116.16

22, 288

0.924220 20

1.413520

116.16

2, 331

0.926220

1.415920

102.18

1, 409

0.824220

1.419020

CH3C( ¨ O)COOCH3

157.17

Solubility in 100 parts solvent

misc alc, eth; sl s aq

110 153.7 50 glass 50 glass 51.1

85 glass 42

60.3 63.3

23 6

198.3

101

153.5

misc aq s alc; misc eth

128

22

196.4

107

sl s aq; misc alc, eth 1.3 aq

196–198

85

s alc, eth

148.0

50

s alc, eth

m344

3-Methyl-3-pentanol

(CH3CH2)2C(CH3)OH

102.18

1, 411

0.828120

1.418620

38

122.4

46

m345

4-Methyl-2-pentanol

102.18

1.410

0.808020

1.411220

90

131.7

41

m346

4-Methyl-2-pentanone 2-Methyl-1-pentene

(CH3)2CHCH2CH(OH)CH3 (CH3)2CHCH2COCH3

100.16

1, 691

0.800620 4

1.395820

83.5

115.7

13

84.16

11, 90

0.679920 4

1.392020

135.7

62.1

26

1.7 aq; misc alc, bz, eth s alc

84.16 114.14

1, 217 22, 406

0.686520 4 0.9529

1.400320 1.4489

135.1 35

67.3 11520mm

23 46

s alc i aq; v s alc

98.15

1, 736

0.854 20 4

1.445820

42

129.5

30

3.1 aq

CH3(CH2)3CH(NH2)CH3 (CH3)2CHCH2C ˜ CH CH3CH2C(CH3)(OH)C ˜ CH

101.19

4, 190

0.76720 4

19

116–118

13

s aq, alc, PE

104.8 30.6

61.2 121–122

38

13 aq; misc bz, acet, PE, EtAc; s eth

C6H5CH2CH2Si(CH3)Cl2

219.2

m347 m348 m349

2-Methyl-2-pentene 4-Methyl-2-pentenoic acid m350 4-Methyl-3-penten2-one m350a 1-Methylpentylamine m351 m352

4-Methyl-1-pentyne 3-Methyl-1-pentyn3-ol

m353

Methyl-(2-phenethyl)dichlorosilane

o-Methylolphenol, h105 2-Methyloxacyclopropane, p227

CH3CH2CH2C(CH3) ¨ CH2 CH3CH2CH ¨ C(CH3)2 (CH3)2CHCH ¨ CHCHCOOH (CH3)2C ¨ CHCOCH3

82.15 98.15

2

1 , 506

Methyl oxirane, p227 Methyl palmitate, m263

0.704120 4 0.868820 4

1.393020 1.431820

1.11120 4

1.51020

996mm

Methyl pentyl ketone, h15

misc alc, eth; sl s aq 1.6 aq

1.309

1.310

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m354 m355 m356 m357 m358 m359 m360 m361 m362 m363 m364 m365 m366 m367

Name (1-Methylphenethyl)trichlorosilane N-(4-Methylphenyl)acetamide Methyl phenylacetate Methylphenylchlorosilane Methylphenyldichlorosilane p-(1-Methyl-2phenylethyl)phenol 1-Methyl-1-phenylhydrazine 1-Methyl-3-phenylpropyl acetate 3-Methyl-1-phenyl2-pyrazolin-5-one Methylphenylsilane Methyl phenyl sulfide N-Methylpiperazine 2-Methylpiperazine

Formula

Formula weight

Beilstein reference

Density

Refractive index

1.22620 4

1.51520

C6H5CH(CH3)CH2SiCl3

253.6

CH3C6H4NHCOCH3

149.19

122, 501

1.21215

C6H5CH2COOCH3 C6H5(CH3)Si(H)Cl

150.18 156.7

9, 434

1.044 1.105420 4

C6H5Si(CH3)Cl2

191.1

C6H5CH2CH(CH3)C6H4OH C6H5N(CH3)NH2

212.29

C6H5CH2CH2CH(CH3)OOCCH3

C6H5Si(CH3)H2 C6H5SCH3

Melting point

153 1.507520 1.57120

1.03822 4

192.26

61, 258

0.991

174.20

24, 20

122.1 124.21

6, 297

100.17 100.17

23, 17

158.25

233, 123

307 215 113100mm

Solubility in 100 parts solvent

s alc, EtAc, HOAc 90

i aq; misc alc, eth

11821mm

96

misc alc, bz, chl, eth

740.05mm

112

205–206 73

15, 117

Flash point

11610mm

1.18720 4

122.17

Boiling point

1.583420

0.88920 4 1.058

1.50620 1.585220

0.903

1.465520

1.483520

m368

4-Methyl-1-piperazinepropanol N-Methylpiperidine

C5H10N ˆ CH3

99.19

20, 19

0.816

1.437820

m369

2-Methylpiperidine

CH3C5H9NH

99.19

20, 95

0.844

1.445920

335

130

287265mm

15

139–240 188

65–67

138 155.6

42 22

v s aq, alc, eth 78 aq; 37 acet; 32 bz

120– 1219mm 106–107

1

119

8

v s aq; misc alc, eth v s aq; misc alc, eth

28–30

5

i aq; s alc

m370 m371 m372

99.19 99.19 129.20

20, 100 20, 101 212, 8

0.845 0.838 1.013

1.447020 1.445820 1.477220

113.16

212, 215

0.920

1.461420

72.11

1, 671

0.789120

1.372720

(CH3)3CH

58.12

1, 124

0.55720

H2NCH2CH2CH2NHCH3

88.15

41, 419

0.844

1.446820

(CH3)2C(NH2)CH2NH2

88.15

4, 266

0.841

1.441020

CH3CH2CH(SH)CH3

90.19

1, 373

0.824625 4

1.433825

CH3C5H9NH CH3C5H9NH

m374

3-Methylpiperidine 4-Methylpiperidine 1-Methyl-3-piperidinemethanol 1-Methyl-4-piperidone 2-Methylpropanal

(CH3)2CHCHO

m375

2-Methylpropane

m376

N-Methyl-1,3propanediamine 2-Methyl-1,2propanediamine 1-Methyl-1-propanethiol

m373

m377 m378

Methylphenols, c279, c280, c281 Methyl-m-phenylene diisocyanate, t172 Methyl phenyl ether, m48 Methyl phenyl ketone, a31

2-Methyl-2-phenylpropane, b425 Methyl -picolinate, m402 Methylpiperidinol, h144 Methyl pivalate, m227

126 124 140–145

1 7 94

v s aq v s aq

60 65

64.1

159.6

11.7

139–141

9 aq; misc alc, bz, chl, eth 13 mL aq; 1320 mL alc; 2890 mL eth 35 23

165

84–85

21

1-Methyl-1-propanethiol, b389 Methyl propargyl ether, m396

sl s aq; v s alc, eth

1.311

1.312

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m379 m380 m381 m382 m383 m384

m385 m386 m387 m388 m389 m390 m391 m392 m393

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

2-Methyl-1-propanethiol 2-Methyl-2-propanethiol 2-Methyl-1-propanol

(CH3)2CHCH2SH

90.19

1, 378

0.835720 4

1.439620

79

88.5

9

v s alc, eth

(CH3)3CSH

90.19

1, 383

0.794325 4

1.419825

1.1

64.2

26

i aq

(CH3)2CHCH2OH

74.12

1, 373

0.801620

1.395820

108

107.9

27

2-Methyl-2-propanol 2-Methylpropene 2-Methyl-2-propene1-sulfonic acid, Na salt 2-Methyl-2-propen1-ol 4-Methyl-2-(2-propenyl)phenol 6-Methyl-2-(2-propenyl)phenol N-Methylpropionamide Methyl propionate 2-Methylpropionic acid 4-Methylpropiophenone Methylpropyldichlorosilane Methyl propyl ether

(CH3)3COH (CH3)2C ¨ CH2 H2C ¨ C(CH3)CH2SO3Na

74.12 56.10 158.15

1, 379 1, 207

0.785820 1.387720 4 140 0.62664

25.8 140.4 300

82.4 6.9

15

10 aq; misc alc, eth misc aq, alc, eth v s alc, eth

H2C ¨ C(CH3)CH2OH

72.11

1, 443

0.857

1.425020

113–115

33

CH3C6H3(CH2CH ¨ CH2)OH CH3C6H3(CH2CH ¨ CH2)OH CH3CH2CONHCH3

148.21

61, 287

0.980

1.538520

238

101

148.21

61, 287

0.992

1.538120

231–233

94

0.930525

1.434525

30.9

148

87.12 88.11 88.11

2, 239 2, 288

0.91520 4 0.95020 4

1.377020 1.393020

88 46.1

79.7 154.7

2 55

CH3C6H4COCH2CH3

148.21

7, 317

0.993

1.528020

7.2

239

96

CH3CH2CH2Si(CH3)Cl2

157.1

1.0425 4

1.42525

CH3CH2COOCH3 (CH3)2CHCOOH

CH3CH2CH2OCH3

74.12

1, 354

0.73820

6 aq; misc alc, eth 23 aq; misc alc, chl, eth

125 39.1

sl s aq; misc alc, eth

m394 m395 m396 m397 m398 m399 m400 m401 m402 m403 m404

2-Methyl-2-propyl1,3-propanediol Methyl propyl sulfide Methyl 2-propynyl ether 2-Methylpyrazine 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine Methyl 3-pyridinecarboxylate Methyl 4-pyridinecarboxylate 1-Methyl-2-pyridone N-Methylpyrrole

2-Methylpropenenitrile, m27 2-Methylpropenoic acid, m26 2-Methylpropionaldehyde, i73 2-Methylpropionamide, i74 2-Methylpropionic acid, i75 2-Methylpropionitrile, i76

132.20

11, 254

CH3SCH2CH2CH3

90.18

13, 1432

0.842420

1.444220

CH3OCH2C ˜ CH

70.09

1, 454

0.830

1.396120

CH3C5H4N CH3C5H4N CH3C5H4N (C5H4N)COOCH3

94.12 93.13 93.13 93.13 137.14

23, 94 20, 234 20, 239 20, 240 22, 39

1.030 0.95015 4 0.96115 4 0.95715 4

1.504220 1.501020 1.506820 1.5058

(C5H4N)COOCH3

137.14

22, 46

1.001

109.13 81.2

21, 268 20, 163

1.112 0.914

C3H7C(CH3)(CH2OH)2

1-Methylpropyl acetate, b413 2-Methylpropyl acetate, i62 2-Methyl-2-propylamine, b418 2-Methylpropylamine, i63 (1-Methylpropyl)benzene, b424 (2-Methylpropyl)benzene, i64

53–55

230

113.0

95.5

s aq

61–62

1

29 67 18.3 3.8 39

135 128–129 143.5 143–145 209

50 26 36 56

1.512220

8.5

207–209

82

1.569020 1.487520

7 57

250740mm 113

15

v s aq, alc, eth v s aq; s alc, eth s aq, alc, eth s aq, alc, eth s aq, alc, bz

i aq; misc alc, eth

2-Methylpropyl formate, i66 2-Methylpropyl lactate, i68 Methyl propyl ketone, p41 2-Methylpropyl 2-methylpropanoate, i67 Methyl pyruvate, m334 Methyl pyridyl ketones, a53, a54, a55

1.313

1.314

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m405 m406 m407 m408 m409 m410 m411 m412 m413 m414

m415 m416 m417

m418 m419 m420 m421

Name N-Methylpyrrolidine N-Methyl-2-pyrrolidinone 2-Methylquinoline 4-Methylquinoline 2-Methylquinoxaline Methyl salicylate -Methylstyrene Methylsuccinic acid Methyl tetradecanoate 2-Methyl-3,3,4,4tetrafluoro-2butanol 2-Methyltetrahydrofuran 1-Methyl-1,2,3,6tetrahydropyridine 3-Methyltetrahydrothiophene-1,1dioxide 4-Methyl-5-thiazoleethanol 2-Methyl-2thiazoline Methyl thioacetate (Methylthio)acetonitrile

Beilstein reference

Density

Refractive index

Melting point

85.15 99.13

20, 4 212, 213

0.81920 4 1.027925

1.424720 1.468025

24.4

80–81 202

21 95

HOC6H4COOCH3

143.19 143.19 144.18 152.15

20, 387 20, 395 231, 44 10, 70

1.058 1.082620 4 1.118 1.183120

1.610820 1.620020 1.615620 1.524020

2 9–10 180–181 8.6

248 261–263 245–247 223.0

79 112 107 110

C6H5C(CH3) ¨ CH2 HOOCCH2CH(CH3)COOH CH3(CH2)12COOCH3

118.18 132.12 242.40

5, 484 2, 636 22, 326

0.909 1.411 0.855

1.537520 1.4303 1.436220

23.2 165.5 110–112 d 18.4 323

HCF2CF2C(CH3)2OH

160.11

1.282

1.352420

117

73

0.860

1.405620

78–80

11

97.16

0.837

1.457020

113–114

8

134.20

1.191

1.477220

276

112

143.21

1.196

1.550820

1357mm

1.067

1.520020

1.039

1.4628 1.482620

Formula

Formula weight

86.13

101.17 CH3COSCH3 CH3SCH2CN

90.14 87.14

17, 12

27, 13

101

Boiling point

Flash point

Solubility in 100 parts solvent misc aq, eth misc aq, alc, bz, eth i aq; s chl, eth misc alc, bz, eth misc aq 0.7 aq; s chl, eth; misc alc, HOAc

45 112

145

37

98 6315mm

10 67

66 aq; v s alc, eth misc alc, bz, eth

s alc, eth

m422 m423 m424 m425 m426 m427 m428 m429

2-(Methylthio)aniline 3-(Methylthio)aniline 4-(Methylthio)benzaldehyde 3-(Methylthio)-2butanone Methyl thiocyanate 3-Methylthiophene 5-Methyl-2-thiophenecarbaldehyde 4-(S-Methylthio)phenol

CH3SC6H4NH2

139.22

13, 399

1.111

1.623920

234

112

CH3SC6H4NH2

139.22

131, 141

1.130

1.642320

16516mm

112

CH3SC6H4CHO

152.22

81, 533

1.144

1.645220

901mm

CH3CH(SCH3)COCH3

118.20

14, 3993

0.975

1.471020

CH3SCN

73.12 98.17 126.18

3, 175 17, 38 171, 151

1.06820 1.016 1.170

1.469720 1.518020 1.582520

50– 5420mm 130–133 115.4 11425mm

CH3SC6H4OH

140.20

61, 419

1-Methyl-2-(3-pyridyl)pyrrolidine, n20 Methylresorcinol, d390 Methylsalicyclic acids, h137, h138 Methyl stearate, m326

Methylsuccinyl chloride, m188 methylsulfonic acid, m30 Methyl theobromine, c1 3-Methyl-2-thiabutane, i104

51 69.0

83–85

44 38 11 87

153– 15620mm

Methyl thienyl ketone, a57 Methyl thioglycolate, m293

i aq; misc alc, eth i aq; misc alc, eth

1.315

1.316

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m430 m431 m432 m433 m434 m435 m436 m437 m438 m439

m440

m441 m442

Name 3-Methylthio-1,2propanediol N-Methylthiourea N-Methyl-o-toluamide N-Methyl-p-toluenesulfonamide Methyl p-toluenesulfonate Methyltriacetoxysilane Methyl 2,2,2-trichloroacetimidate Methyltrichlorogermane Methyl trifluoromethanesulfonate N-Methyl-N-trimethylsilylacetamide N-Methyl-N-(trimethylsilyl)trifluoroacetamide Methyltripropoxysilane (Methyl)triphenylphosphonium bromide

Formula

Formula weight

Beilstein reference

CH3SCH2CH(OH)CH2OH

122.19

CH3NHC( ¨ S)NH2 CH3C6H4CONHCH3

90.15 149.19

4, 70 9, 465

CH3C6H4SO2NHCH3

185.25

11, 105

CH3C6H4SO2OCH3

186.23

11, 99

Density

Refractive index

1.164

1.516020

Melting point

Boiling point

119–121 69–71

1.16815

Solubility in 100 parts solvent

112 v s aq, alc

76–79 27.5

CH3Si(OOCCH3)3

220.3

43, 1896

1.17520 4

Cl3CC( ¨ NH)OCH3

176.43

2, 212

1.425

CH3GeCl3

193.98

1.730

CF3SO2OCH3

164.10

1.450

1.324420

94–99

CH3CON(CH3)Si(CH3)3

145.3

1.43920 4

0.90120

154

CF3CON(CH3)Si(CH3)3

199.25

1.075

1.380220

132

CH3Si(OC3H7)3

220.4

0.8820 4

1.408520

8313mm

[CH3P(C6H5)3]Br

357.24

44, 4011

Flash point

1.40820

883mm

1.478020

149

none

111

230–233

38

25

m443

2-Methylundecanal

m444 m445 m446 m447

Methyl urea Methyl vanillate Methyl vinyl ether 2-Methyl-5-vinylpyridine Morpholine

m448 m449 m450 m451

CH3(CH2)8CH(CH3)CHO CH3NHCONH2 CH3OC6H3(OH)COOCH3 CH3OCH ¨ CH2

4-Morpholinecarbonitrile N-Morpholino-1cyclohexene 2-(N-Morpholino)ethanesulfonic acid

4-Methyl-2-thiouracil, h120 Methyltrichlorosilane, t238 Methyltriethoxysilane, t266a Methyl trimethylacetate, m227 Methyltris(2-methoxyethoxy)silane, t429 -Methylumbelliferone, h140 Methyluracil, d391

0.83015 4

184.32 74.08 182.18 58.08 119.17

1.204 0.751120 4 0.898

27, 5

271

93

1.3947 1.543720

101–102 d 64–65 285–287 112 5.5 10050mm

56 65

1.00720 4

1.454220

4.9

128.9

35

112.12

1.109

1.473020

730.6mm

104

167.25

0.995

1.512820

117–122

68

87.12

4, 64 10, 396 13, 1857

1.432120

195.24

Methyl urethane, m181 Methyl valerate, m340 3-Methylvaleric acid, m342 4-Methylvaleronitrile, m339 Methyl veratrate, m225 Michler’s ketone, b171 Monoethyl adipate, e149

s alc, eth v s aq, alc; i eth s hot alc, hot PE 0.8 aq; v s alc

misc aq, alc, bz, eth

 300

Monoglyme, d439 Monomethyl adipate, m273 Monomethyl glutarate, m272 Monomethyl succinate, m274 Mordent violet 5, a60 4-Morpholinoethanol, h122 1-Morpholinocyclopentene, c361

1.317

1.318

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. m452

Name

m453

3-(N-Morpholino)1,2-propanediol -Myrcene

n1 n2

1-Naphthaldehyde Naphthalene

n3

n8

1-Naphthalenecarboxylic acid 1,5-Naphthalenediamine 1,8-Naphthalenediamine 1-Naphthalenemethylamine 1,8-Naphthalic anhydride 1,8-Naphthalimide

n9 n10

1-Naphthol 2-Naphthol

n11 n12

1,4-Naphthoquinone (2-Naphthoxy)acetic acid 2-(1-Naphthyl)acetamide

n4 n5 n6 n7

n13

Formula

Formula weight

Beilstein reference

161.20

Density

Refractive index

1.157

Melting point 37–38

Boiling point

Flash point

19130mm

112

166–168

39

Solubility in 100 parts solvent

(CH3)2C ¨ CHCH2CH2C( ¨ CH2)CH ¨ CH2 C10H7CHO C10H8

136.24

1, 264

0.79420 4

1.470920

156.18 128.17

7, 400 5, 531

1.15020 4 1.16220 4

1.652020 1.5821100

C10H7COOH

172.18

9, 647

1–2 16115mm 80.2 217.7 subl above mp 160–162 300

C10H6(NH2)2

158.20

13, 203

185–187

C10H6(NH2)2

158.20

13, 204

1.126599 4

1.682899

C10H7CH2NH2

157.22

12, 1316

1.073

1.642920

198.18

17, 521

267–269

sl s HOAc

197.19

21, 527

300

C10H7OH C10H7OH

144.17 144.17

6, 596 6, 627

1.095499 4 1.2174

7, 724 6, 645

1.422

C10H7OCH2COOH

158.16 202.21

sl s alc; i bz, eth, aq v s alc, bz, chl, eth 0.1 aq; 125 alc; 6 chl; 77 eth; s alk s bz, chl, eth, alk

C10H7CH2CONH2

185.23

9, 666

1.620699

66.5

v s hot alc, eth s hot aq, hot alc

20512mm 290–293

96 288 121–123 285–286 128 subl  100 155–157 181–183

112 78

s alc, chl, eth, HOAc s alc, eth 0.3 aq; 7 alc; 33 bz; 50 chl

sl s aq; s alc, eth 112

161

i aq; s bz, CS2

n14 n15 n16 n17 n18 n19 n20

1-Naphthyl acetate 1-Naphthylacetic acid 1-Naphthylacetonitrile 1-Naphthylamine 2-Naphthylsulfonic acid 1-(1-Naphthyl)-2thiourea Nicotine

C10H7OOCCH3 C10H7CH2COOH

186.21 186.21

6, 608 9, 666

C10H7CH2CN

167.21

9, 667

C10H7NH2 C10H7SO3H

143.18 208.23

12, 1212 11, 171

C10H7NHC( ¨ S)NH2

202.28

12, 1241

162.24

23, 117

MSTFA, m440 Mucic acid, t84 Mucochloric acid, d208 Myristolyl chloride, t41 Myristic acid, t39 Myristic acid, t40 Myristyl bromide b352 Naphthacene, b7 1-Naphthaleneacetamide, n13 1-Naphthaleneacetonitrile, n16 Naphthalenediols, d392, d393, d394, d395

1.12325 25 1.44125

43–46 135

d

s alc, eth 3.3 alc; v s chl, eth

1.619220

33–35

19418mm

112

s alc

1.6703

50 91

301 d

157

0.2 aq; v s alc, eth 77 aq; s alc, eth

198 1.009720 4

1-Naphthol-2-carboxylic acid, h148 3-Naphthol-2-carboxylic acid, h149 1-Naphthol-3,6-disulfonic acid, h151 2-Naphthol-3,6-disulfonic acid, h150 1-Naphthonitrile, c293 (2-Naphthoxy)acetic acid, n12 N-1-Naphthylaniline, p130 Natural orange 6, h152 NBA, b218 NBS, b351 Neohexane, d489

1.528220

79

12317mm

Neohexene, d499 Neopentane, d592 Neopentyl alcohol, d595 Neopentyl glycol, d594 Neral, d563 Nerolidol, h184 Nicotinaldehyde, p256 Nicotinic acid, p256 Nicotinonitrile, c296

0.6 aq; 2.4 acet; s alc misc aq; v s alc, eth, PE

1.319

1.320

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. n21 n22 n23 n24 n25 n26 n27 n28 n29 n30 n31

Name Nitrilotriacetic acid m-Nitroacetophenone p-Nitroacetophenone o-Nitroaniline m-Nitroaniline p-Nitroaniline 3-Nitrobenzaldehyde 4-Nitrobenzaldehyde 2-Nitrobenzamide

Formula weight

Beilstein reference

N(CH2COOH)3

191.14

4, 369

246 d

O2NC6H4COCH3 O2NC6H4COCH3 O2NC6H4NH2 O2NC6H4NH2 O2NC6H4NH2 O2NC6H4CHO O2NC6H4CHO O2NC6H4CONH2

165.15 165.15 138.13 138.13 138.13 151.12 151.12 166.12

7, 288 7, 288 12, 687 12, 698 12, 711 7, 250 7, 256 9, 373

76–78 78–80 69–70 114 146 58 106–107 174–178

C6H5NO2 O2NC6H3(COOH)2

123.11 211.13

5, 233 9, 851

O2NC6H3(COOH)2

211.13

9, 823

216 d

2 aq; v s hot alc

O2NC6H3(COOH)2

211.13

9, 828

163–166

v s aq, alc; s eth

O2NC6H3(COOH)2

211.13

9, 840

260–261

0.15 aq; v s alc, eth

65–67

s eth; d hot aq, alc s alc, acid 0.7 aq; 33 alc; 22 eth 0.3 aq; 33 alc; 40 acet 9 alc; 2 eth; 5 acet

Formula

Density

Refractive index

1.44215 1.43 1.43714 1.279220 4 1.496 32 1.4624 1.20515 4

1.554615

Melting point

O2NC6H4SO2Cl

221.62

11, 67

n36 n37

Nitrobenzene 2-Nitrobenzene-1,4dicarboxylic acid 3-Nitrobenzene-1,2dicarboxylic acid 4-Nitrobenzene-1,2dicarboxylic acid 5-Nitrobenzene-1,3dicarboxylic acid 2-Nitrobenzenesulfonyl chloride 6-Nitrobenzimidazole 2-Nitrobenzoic acid

O2NC6H4COOH

163.14 167.12

23, 135 9, 370

1.58

207–209 146–148

n38

3-Nitrobenzoic acid

O2NC6H4COOH

167.12

9, 376

1.494

142

n39

4-Nitrobenzoic acid

O2NC6H4COOH

167.12

9, 389

1.58

242.8

n32 n33 n34 n35

Boiling point

Flash point

Solubility in 100 parts solvent 0.1 aq; s hot alc

202 202 284 306 260100mm 16423mm

165

317

5.8 210.8 270–272

87

s alc, eth s alc s hot aq, alc, chl 0.1 aq; 5 alc; 6 eth 4 alc; 3.3 eth; s bz s alc, chl, eth s alc, bz, HOAc s hot aq, hot alc, eth v s alc, bz, eth

n40

4-Nitrobenzonitrile

O2NC6H4CN

148.12

9, 397

146–149

n41

O2NC6H4COCl

185.57

9, 381

32–35

275–278

O2NC6H4COCl

185.57

9, 394

75

205105mm

d aq, alc; s eth

O2NC6H4CONHCH2COOH

224.17

9, 395

131–133

O2NC6H4CH2OH

153.14

6, 449

30–32

1803mm

s aq, alc, eth

O2NC6H4CH2OH

153.14

6, 450

92–94

18512mm

v s alc, eth; sl s aq

O2NC6H4CH2Br

216.04

5, 334

98–100

2 alc; v s eth

O2NC6H4CH2Cl

171.58

5, 329

70–73

8 alc; s eth

n48 n49 n50

3-Nitrobenzoyl chloride 4-Nitrobenzoyl chloride N-(p-Nitrobenzoyl)glycine 3-Nitrobenzyl alcohol 4-Nitrobenzyl alcohol 4-Nitrobenzyl bromide 4-Nitrobenzyl chloride 2-Nitrobiphenyl 4-Nitrobiphenyl 1-Nitrobutane

s HOAc; sl s aq, alc d aq, alc; v s eth

O2NC6H4C6H5 O2NC6H4C6H5 CH3CH2CH2CH2NO2

199.21 199.21 103.18

5, 582 5, 583 1, 123

1.4425 4

1.61325

0.97520 20

1.4112

n51 n52

3-Nitro-2-butanol 2-Nitrodiphenylamine

CH3CH(NO2)CH(OH)CH3 O2NC6H4NHC6H5

119.12 214.22

1, 373 12, 690

1.129625 4

1.441420

n42 n43 n44 n45 n46 n47

Ninhydrin, i16 Nioxime, c323 2,2,2 -Nitrilotriethanol, t264

1,1,1 -Nitrilotris(2-propanol), t309 2-Nitro-p-anisidine, m79 5-Nitro-o-anisidine, m78

36.7 325 112–114 340 81.3 152.8 9210mm

179

s alc, acet, CCl4 sl s alc; v s eth sl s aq; misc alc, eth

91

76–78 Nitroanisoles, m81, m82 4-Nitrobenzyl cyanide, n65 Nitrocresols, m323, m324

i aq; s alc

1.321

1.322

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

n53

Nitroethane

CH3CH2NO2

n54 n55 n56 n57 n58

1-Nitroguanidine 5-Nitro-1H-indazole Nitromethane 1-Nitronaphthalene 3-Nitro-2-pentanol

O2NNHC( ¨ NH)NH2

n59 n60 n61

2-Nitrophenethyl alcohol 2-Nitrophenol 4-Nitrophenol

n62 n63 n64 n65 n66 n67 n68 n69

Formula weight 75.07

Beilstein reference

Density

Refractive index

Melting point

Boiling point

1, 99

1.052820 20

1.392020

90

1.379525

35

 112

114.1

Flash point 30

Solubility in 100 parts solvent 4.5 aq; misc alc, eth; s alk, chl 0.4 aq; sl s MeOH s alc, bz, eth, acet 11 aq; s alc, eth s alc; v s chl, eth

CH3NO2 C10H7NO2 CH3CH2CH(NO2)CH(OH)CH3 O2NC6H4CH2CH2OH

104.07 163.14 61.04 173.17 133.15

3, 126 23, 129 1, 74 5, 553 1, 385

1.132225 4 1.223 1.081825 4

1.443020

d 225 207–209 28.4 101.2 59–60 304 10010mm

167.16

6, 218

1.190

1.563720

2

O2NC6H4OH O2NC6H4OH

139.11 139.11

6, 213 6, 226

1.495 1.495

4-Nitrophenyl acetate

O2NC6H4OOCCH3

181.15

6, 233

77–79

2-Nitrophenylacetic acid 4-Nitrophenylacetic acid 4-Nitrophenylacetonitrile 4-Nitrophenyl chloroformate 2-Nitro-p-phenylenediamine 4-Nitro-o-phenylenediamine 4-Nitrophenylhydrazine

O2NC6H4CH2COOH

181.15

9, 454

139–142

s alc, bz, eth, alk s aq; v s alc, chl, eth s aq; v s alc, bz, eth s hot aq, alc

O2NC6H4CH2COOH

181.15

9, 455

153

s alc, bz, eth

O2NC6H4CH2CN

162.15

9, 456

117

s alc, eth

O2NC6H4OOCCl

201.57

61, 120

77–79

O2NC6H3(NH2)2

153.14

13, 120

137–140

O2NC6H3(NH2)2

153.14

13, 29

199–201

s acid

O2NC6H4NHNH2

153.14

15, 468

156 d

s alc, chl, eth, hot bz

267

44–45 214–216 112–114 279

90

16219mm

n70

20

1848mm

s alc, eth

6, 232

53–56

320

s bz, eth

193.11

17, 486

163–165

CH3CH2CH2NO2

89.09

1, 115

1.000920

1.401620

104.0

131.2

33

2-Nitropropane

(CH3)2CHNO2

89.09

1, 116

0.987620

1.394920

91.3

120.3

37

2-Nitro-1-propanol 4-NitropyridineN-oxide 8-Nitroquinoline Nitrosobenzene N-Nitrosodimethylamine p-Nitrosodiphenylamine 1-Nitroso-2-naphthol

CH3CH(NO2)CH2OH O2NC5H4N(O)

105.09 140.10

1, 358

1.184125 4

1.437920

9910mm

100

1.4 aq; misc alc, eth 1.7 aq; misc alc, eth s aq, alc, eth

C6H5NO (CH3)2NNO

174.16 107.11 74.08

20, 373 5, 230 8, 84

61

s alc, bz, eth; i aq i aq; s alc v s aq, alc, eth

C6H5NHC6H4NO

198.22

C10H6(NO)OH

173.16

n73

2-Nitrophenyl phenyl ether 4-Nitrophenyl phenyl ether 3-Nitrophthalic anhydride 1-Nitropropane

n74 n75 n76

n71 n72

n77 n78 n79 n80 n81

Nitroglycerin, g21 5-Nitroisophthalic acid, n34 3-Nitrophenyl disulfide, b194

O2NC6H4OC6H5

215.21

62, 222

O2NC6H4OC6H5

215.21

1.253922

1.57520

sl s aq, bz

159–162 89–91 67–69 1.004820 4

7, 712

4-Nitrophenyl disulfide, b195 4-(p-Nitrophenylthio)aniline, a243 3-Nitro-o-phthalic acid, n32

1.436820

5918mm 151–153

144–145

v s alc, bz, chl, eth

109–110

3 alc; s bz, eth, alk

4-Nitro-o-phthalic acid, n33 N-Nitrosophenylhydroxylamine, c284

1.323

1.324

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. n82

n83

Name 1-Nitroso-2naphthol-3,6-disulfonic acid, di-Na salt hydrate 4-Nitrosophenol

Formula weight

Beilstein reference

377.26

112, 190

300

2.5 aq; sl s alc

ONC6H4OH

123.11

7, 622

d 126

C6H5CH ¨ CHNO2 CH3C6H4NO2 CH3C6H4NO2 CH3C6H4NO2 CF3C6H4NO2

149.15 137.14 137.14 137.14 191.11

5, 478 5, 318 5, 321 5, 323 52, 251

1.162219 15 1.158120 4 1.392

1.547220 1.545920

s aq; v s alc, eth; explodes on contact with conc acid, alk, or fire s alc; v s eth s alc, bz misc alc, eth; s bz s alc, bz, chl, eth v s alc, bz

CF3C6H4NO2

191.11

5, 327

1.43616 4

Formula

n90 n91 n92 n93 n94 n95

-Nitrostyrene 2-Nitrotoluene 3-Nitrotoluene 4-Nitrotoluene 2-Nitro-,,trifluorotoluene 3-Nitro-,,trifluorotoluene Nonadecane 1,8-Nonadiyne Nonane 1,9-Nonanediamine Nonanedinitrile 1,9-Nonanedioic acid

CH3(CH2)17CH3 HC ˜ C(CH2)5C ˜ CH CH3(CH2)7CH3 H2N(CH2)9NH2 NC(CH2)7CN HOOC(CH2)7COOH

268.51 120.20 128.26 158.29 150.23 188.22

n96 n97 n98 n99

1,9-Nonanediol Nonanenitrile Nonanoic acid 1-Nonanol

HO(CH2)9OH CH3(CH2)7CN CH3(CH2)7COOH CH3(CH2)8OH

n100

5-Nonanone

(C4H9)2CO

n84 n85 n86 n87 n88 n89

Density

Refractive index

Melting point

Boiling point

Flash point

Solubility in 100 parts solvent

58 10 15.5 53–54 31–32

250 222 231.9 238 10520mm

106 101 106

1.471520

2.4

200–205

87

s alc, eth

1, 174 12, 248 1, 165 4, 272 2, 709 2, 707

0.777632 4 0.815921 4 0.717620 4

1.433538 1.449220 1.405420

31.9 21 53.5 37–38

168 41 31

s eth; sl s alc

0.929 1.02920 4

1.446020

112

106.5

330.6 5513mm 150.8 258 17611mm 286100mm

v s alc, bz, eth 0.24 aq; v s alc; 3 eth

160.26 139.24 158.24 144.26

1, 493 2, 354 2, 352 1, 423

0.82115 4 0.90620 4 0.827420 4

1.426020 1.433020 1.433820

45–47 34.2 12.5 5.5

17715mm 224.0 254 213.1

81 100 75

142.24

1, 710

0.80620 4

1.419020

50

187

60

s alc, eth s alc, chl, eth 0.6 aq; misc alc, eth misc alc, eth

s abs alc, eth

n101 n102 n103 n104 n105 n106 n107 n108 n109

Nonanoyl chloride 1-Nonene Nonyl aldehyde Nonylamine Nopol Nopyl acetate Norbornane 2-Norbornanone trans-5-Norbornene2,3-dicarbonyl dichloride

Nitroso-R-salt, n82 Nitroterephthalic acid, n31 2-Nitro-p-toluidine, m317 4-Nitro-o-toluidine, m315

CH3(CH2)7COCl H(CH2)7CH ¨ CH2 CH3(CH2)7CHO CH3(CH2)8NH2

176.69 126.24 142.24 143.27 166.26 210.3 96.17 110.16 219.07

2, 353 12, 202 1, 708 4, 198

0.94615 4 0.729220 0.82719 19 0.782 0.973 0.980525

1.437720 1.415720 1.424020 1.433020 1.493020 1.472120

52, 45 7, 57

60.5 81.4

82–84 88–91 1.349

5-Nitro-o-toluidine, m316 4-Nitroveratrole, d444 Nitroxylenes, d556, d557, d558, d559 Nonyl alcohol, n99

1.516520

215.4 146.9 185 201 230–240

81 46 63 62 98

168–172 11811mm

33 110

d aq, alc: s eth

sl s aq; s alc, eth

s alc

2,5-Norbornadiene, b129 exo-2-Norbornanamine, a250 5-Norbornen-2-carbaldehyde, b131 Norbornene, b130

1.325

1.326

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. n110 n111 n112 o1 o2 o3 o4 o5 o6 o7 o8 o9 o10 o11 o12 o13 o14

Name 5-Norbornen-2-yl acetate exo-2-Norbornyl formate ()-Norephedrine HCl (Z,Z)-9,12-Octadecadienoic acid Octadecanamide Octadecane 1-Octadecanethiol Octadecanoic acid 1-Octadecanol 9,12,15-Octadecatrienoic acid 1-Octadecene 9-Octadecen-1-amine (Z)-9-Octadecenoic acid (E)-9-Octadecenoic acid (Z)-9-Octadecen1-o1 Octadecylamine Octadecyl isocyanate

Formula

CH3(CH2)4CH ¨ CHCH2CH ¨ CH(CH2)7COOH CH3(CH2)16CONH2 CH3(CH2)16CH3 CH3(CH2)17SH CH3(CH2)16COOH CH3(CH2)17OH CH3(CH2CH ¨ CH)3CH2(CH2)6COOH CH3(CH2)15CH ¨ CH2 CH3(CH2)7CH ¨ CH(CH2)8NH2 CH3(CH2)7CH ¨ CH(CH2)7COOH CH3(CH2)7CH ¨ CH(CH2)7COOH CH3(CH2)7CH ¨ CH(CH2)8OH CH3(CH2)17NH2 CH3(CH2)17NCO

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

152.19

1.044

1.470020

7614mm

62

140.18

1.048

1.462220

6716mm

53

Solubility in 100 parts solvent

187.67

132, 371

280.44

2, 496

0.902520 4

1.469920

5

23016mm

283.50 254.50 286.57 284.48

2, 384 1, 173

0.776728 4

2, 377

0.84770

1.436728 1.4648 1.429980

108–109 28.2 29–31 70

25112mm 316.7 360 383

270.50 278.44

1, 431 2, 499

0.812358 4 0.79118 4

1.438820 1.480020

57.9

20310mm 23017mm

252.49 267.50

1, 226

0.79118 4 0.813

1.443920 1.457820

17.7

314.9

282.47

2, 463

0.890620 4

1.457120

4

286100mm

282.47

22, 441

0.85179

1.430899

44–45

288100mm

268.49

1, 453

0.84920 4

1.461020

13–19

1958mm

112

s alc, eth

269.52 295.51

4, 196

0.77727 0.847

50–52

23232mm 1702mm

148 185

s alc, bz, eth

1.450120

174–176

165 185

112 148 154

v s eth; misc PE; s abs alc s hot alc, hot eth s acet, eth; sl s alc s eth; sl s alc 4.9 alc; 20 bz; 50 chl; 3.9 acet s alc, eth s alc, bz, eth s hot acet

misc alc, eth; s bz, chl s bz, chl, eth

o15 o16 o17 o18 o19 o20 o21 o22 o23 o24 o25

Octadecyltrichlorosilane Octadecyl vinyl ether 1,7-Octadiene 1H,1H,5H-Octafluoro-1-pentanol Octamethylcyclotetrasilazane Octamethylcyclotetrasiloxane Octamethyltrisiloxane Octane 1,8-Octanediamine 1,8-Octanedioic acid 1,2-Octanediol

Norbornylene, b130 Norcamphor, n107 Norleucine, a183 Norvaline, a253 NTA, n21

CH3(CH2)17SiCl3

387.94

0.984

1.460220

22310mm

89

CH3(CH2)17OCH ¨ CH2

296.54

0.82130 4

1.444030

1875mm

177

H2C ¨ CH(CH2)4CH ¨ CH2 HCF2CF2CF2CF2CH2OH

110.20 232.08

0.746 1.664720

1.422120 1.319020

114–121 140–141

9 74

[ ˆ (CH3)2SiNH ˆ ]4

292.7

0.9522

1.45825

224–225

[ ˆ (CH3)2SiO ˆ ]4

296.62

0.955820

1.396820

17.5

175

90

[(CH3)3SiO]2Si(CH3)2 CH3(CH2)6CH3 H2N(CH2)8NH2 HOOC(CH2)6COOH

236.0

0.820020

1.384820

~80

152–153

38

s bz, PE; sl s alc

114.23 144.26 174.20

1, 159 4, 271 2, 691

0.702520 4

1.397420

56.8 125.7 50–52 225 140–144 23015mm

15 165

s eth; sl s alc

CH3(CH2)5CH(OH)CH2OH

146.23

13, 2217

Octadecyl bromide, b319 Oxtadecyl mercaptan, o4 2,3,4,6,7,8,9,10-Octahydropyrimido [1,2-a]azepine, d46 Octaldehyde, o40

28

36–38

13210mm

0.16 aq; 0.6 eth; s alc 112

Octamethylene glycol, o26 Octanal, o40 1,8-Octanedicarboxylic acid, d9

1.327

1.328

TABLE 1.15 Physical Constants of Organic Compounds (continued ) Formula weight

Beilstein reference

Density

Refractive index

Melting point

HO(CH2)8OH CH3(CH2)6CN CH3(CH2)7SH CH3(CH2)6COOH

146.23 125.22 146.30 144.21

1, 490 2, 349 13, 1710 2, 347

0.813520 0.843 0.908820 4

1.420220 1.452520 1.427920

59–61 45.6 49.2 16.6

17220mm 205.2 199.0 239.3

73 68 110

1-Octanol

CH3(CH2)7OH

130.23

1, 418

0.825820 4

1.429620

15.0

195.2

81

o31

DL-2-Octanol

CH3(CH2)5CH(OH)CH3

130.23

1, 419

0.820720 4

1.420220

38.6

179–180

71

o32

DL-3-Octanol

130.23

11, 208

0.821620

1.426220

174–176

65

o33

4-Octanol

0.819220

1.42520

176.6

71

o34 o35 o36

2-Octanone 3-Octanone 4-Octanone

o37 o38 o39 o40 o41

Octanoyl chloride Octaphenylcyclotetrasiloxane 1-Octene Octyl aldehyde Octylamine

CH3(CH2)4CH(OH)CH2CH3 CH3(CH2)3CH(OH)CH2CH2CH3 CH3(CH2)5COCH3 CH3(CH2)4COCH2CH3 CH3(CH2)3COCH2CH2CH3 CH3(CH2)6COCl [ ˆ (C6H5)2SiO ˆ ]4

o42 o43 o44 o45

4-Octylaniline Octyltrichlorosilane 1-Octyne 1-Octyn-3-ol

No.

Name

Formula

o26 o27 o28 o29

1,8-Octanediol Octanenitrile 1-Octanethiol Octanoic acid

o30

130.23

Boiling point

Flash point

Solubility in 100 parts solvent v s alc; sl s aq, eth s eth; sl s alc s alc 0.07 aq; v s alc, chl, eth, PE 0.06 aq; misc alc, chl, eth 0.08 aq; misc alc, eth

128.22 128.22 128.22

1, 704 1, 706 1, 706

0.81920 4 0.822020 4 0.809

1.415020 1.415020 1.413920

16

173 167–168 164

62 46 45

i aq; misc alc, eth i aq; misc alc, eth

162.66 793.2

2, 348

0.95515 15 1.185

1.435020

70

195 3401mm

75

d aq, alc; s eth s alc, bz, HOAc

CH3(CH2)5CH ¨ CH2 CH3(CH2)6CHO CH3(CH2)7NH2

112.22 128.22 129.25

1, 221 1, 704 4, 196

0.714920 4 0.82120 4 0.782

1.408720 1.418320 1.429020

101.7 12–15 5 to 1

121.3 163.4 175–177

21 51 62

i aq; misc alc, eth sl s aq; misc alc i aq; s alc, eth

CH3(CH2)7C6H4NH2 CH3(CH2)7SiCl3 CH3(CH2)5C ˜ CH CH3(CH2)4CH(OH)C ˜ CH

205.35 247.7 110.19 126.20

12, 1185 1.0720 0.745720 0.864

1.44720 1.415920 1.441020

1, 258

79.3

17513mm 226730mm 126.2

i aq; s alc, eth 63

o46

L-()-Ornithine

o47 o48

Oxacycloheptane Oxalic acid

o49 o50 o51

Oxalic acid dihydrate Oxalyl bromide Oxalyl chloride

o52 o53 o54 o55 o56

132.16

4, 420

HOOCCOOH

100.16 90.04

2, 502

0.890 1.9017 4

HOOCCOOH·2H2O

126.07

2, 502

1.65319 4

BrCO ˆ COBr ClCO ˆ COCl

215.84 126.93

2, 542

1.48813 4

Oxalyl dihydrazide

H2NNHCO ˆ CONHNH2

118.10

2, 559

Oxamic hydrazide Oxamide 2-Oxazolidone 2-Oxobutyric acid

H2NCO ˆ CONHNH2 H2NCO ˆ CONH2

103.08 88.07 87.08 102.09

2, 559 2, 545 27, 135 3, 629

tert-Octylamine, t102 Octyl bromide, b320 Octyl cyanide, n97 Octyl chloride, c190 Octyl iodide, i46 Oleic acid, o11 Oleyl alcohol, o12 Oleylamine, o9

H2N(CH2)3CH(NH2)COOH

CH3CH2C( ¨ O)COOH

142 1.44020

v s aq, alc; sl s eth 122

9.5 aq; 24 alc; 1.3 eth 14 aq; 40 alc; 1 eth

2H2O, 102 1.5220 1.434013

12

103720mm 64

240 d 1.66720 4 1.20017 4

Orthanolic acid, a118 7-Oxabicyclo[2.2.1]heptane, e6 7-Oxabicyclo[4.1.0]heptane, e5 6-Oxabicyclo[3.1.0]hexane, e9 2-Oxabicyclo[6.1.0]nonane, e7a Oxacyclobutane, t345 Oxacyclopentane, t66 Oxalylurea, i6

10

189 d

1.397220

218 d d 350 86–89 32–34

22048mm 8216mm

none none

s eth; violent d aq, alc s hot aq; sl s alc, eth s alk; sl s aq; i eth sl s hot aq, alc v s aq, alc; v sl s eth

1,4-Oxathiane, t164 Oxepane, o47 Oxetane, t345 Oxirane, e129 2-Oxo-10-bornanesulfonic acid, c7 3-Oxobutanoic acid, a24 3-Oxobutyraldehyde dimethyl acetal, d435

1.329

1.330

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. o57

p1

2-Oxohexamethyleneimine 4-Oxopentanoic acid 2-Oxopropionaldehyde 2-Oxopropionic acid 2,2-Oxydiacetic acid 4,4-Oxydianiline 3,3-Oxydipropionitrile Paraformaldehyde

p2 p3

Paraldehyde Parathion

p4 p5

DL-Patchenol Pentabromoethylbenzene Pentabromophenol Pentachloroacetone Pentachlorobenzene Pentachloroethane

o58 o59 o60 o61 o62 o63

p6 p7 p8 p9

Formula weight

Beilstein reference

Density

Refractive index

Melting point

113.16

212, 216

1.0275 4

1.4935

69.2

18050mm

CH3COCH2CH2COOH CH3COCHO

116.12 72.06

3, 671 1, 762

1.144725 4 1.045524

1.439620 1.420920

33–35

245.8 72

CH3COCOOH HOOCCH2OCH2COOH

88.06 134.09

3, 608 3, 234

1.26715 4

1.431520

11.8 165 d 142–145 d

H2NC6H4OC6H4NH2 NCCH2CH2OCH2CH2CN

200.24 124.14

13, 441 1.043

1.440520

Name

Formula

(CH2O)x

1, 566

1120.5mm 156 d

Solubility in 100 parts solvent 84 aq

137 none

v s aq, alc, bz, eth s aq, alc

82

misc aq, alc, eth v s aq, alc; sl s eth

19, 385

0.998415 1.2625 4

1.404920 1.537025

166.26 500.67

62, 64 5, 357

0.987

1.504520

CH3CH2C6Br5 C6Br5OH Cl2CHCOCCl3 C6HCl5 Cl2CHCCl3

488.62 230.31 250.34 202.30

6, 206 1, 656 5, 205 1, 87

1.690 1.834216 1.671225 4

12.5 6

 112 71

124 375 234–238

slowly s aq; s alk; i alc, eth 11 aq; misc alc, chl v s alc, bz, eth

107

137–139

1.496720 1.503020

223–226 21 anhyd 82–85 29.0

subl 192 275–277 160.5

C6Cl5NO2

295.34

5, 247

1.71825 4

140–143

p11

Pentachloronitrobenzene Pentachlorophenol

C6Cl5OH

266.34

6, 194

1.97822 4

190–191 310 d

p12

Pentachloropyridine

C5Cl5N

251.33

20, 232

p10

Flash point

190 d

132.16 291.27

[ ˆ CH(CH3)O ˆ ]3 (C2H5O)2P( ¨ S)(O)C6H4NO2

Boiling point

124–126

none none

sl s alc, eth i aq; v s acet v s bz, chl, eth 0.05 aq; misc alc, eth s bz, chl v s alc; s bz; 148 eth

p13 p14 p15 p16 p17 p18 p19 p20

Pentadecane 8-Pentadecanone 3-Pentadecylphenol 1,2-Pentadiene (E)-1,3-Pentadiene (Z)-1,3-Pentadiene 1,4-Pentadiene Pentaerythritol

CH3(CH2)13CH3 [CH3(CH2)6]2CO C15H31C6H4OH CH3CH2CH ¨ C ¨ CH2 CH3CH ¨ CHCH ¨ CH2 CH3CH ¨ CHCH ¨ CH2 H2C ¨ CHCH2CH ¨ CH2 C(CH2OH)4

212.42 226.40 304.52 68.12 68.12 68.12 68.12 136.15

1, 172 1, 717

0.768420 4

1.431920

1, 251 1, 251 1, 251 1, 251 1, 528

0.692620 4 0.676020 0.691020 0.660822 4 1.3825 4

1.420920 1.430120 1.436320 1.388820 1.548

p21

Pentaerythrityl tetrabromide Pentaerythrityl tetranitrate

C(CH2Br)4

387.76

1, 142

C(CH2ONO2)4

316.15

12, 602

p22

3-Oxo-N-phenylbutanamide, a32 2,2-Oxybis(chloroethane), b158 1,1-Oxybis(2-methylpropane), d407 1,1-Oxybis(pentane), d651 3,3-Oxybis(1-propene), d26 2,2-Oxydiethanethiol, b186

2,2-Oxydiethanol, b181 Palmitic acid, h35 Pamoic acid, m235 Parabanic acid, i6 Pelargonaldehyde, n103 Pelargonic acid, n98

9.9 41–43 45–48 137.3 87.5 140.8 148.3 260

270.6 178 1951mm 44.9 42.0 44.1 26.0 subl

132

v s alc, eth s alc

28 28 4 6 aq; v sl s alc; i eth

158–160 305–306 1.77320 4

140

sensi- acet; sl s eth, tive alc to shock; explodes on percussion

Pelargonoyl chloride, n101 Pelargononitrile, n97 Pentabromophenyl ether, b197 Pentaerythritol diformal, t126

1.331

1.332

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. p23

Name

Formula

Formula weight

Beilstein reference

C6H(CH3)5

148.25 136.24

5, 443

138.17

262, 213

1.532

1.442520

0.91720 4 0.870

1.52720 1.473320

p27

CH3CH2CH2CH2CHO

86.13

1, 676

0.809520 4

p28 p29 p30 p31 p32

Pentane 1,5-Pentanediamine 1,5-Pentanediol 2,3-Pentanedione 2,4-Pentanedione

CH3CH2CH2CH2CH3 H2N(CH2)5NH2 HO(CH2)5OH CH3CH2COCOCH3 CH3COCH2COCH3

72.15 102.18 104.15 100.11 100.11

1, 130 4, 266 1, 481 1, 776 1, 777

p33 p34

CH3CH2CH2CH2CN  CH3(CH2)4SO 3 Na

83.13 174.19

p35 p36 p37

Pentanenitrile 1-Pentanesulfonic acid, Na salt 1-Pentanethiol Pentanoic acid 1-Pentanol

CH3(CH2)4SH CH3(CH2)3COOH CH3(CH2)4OH

p38

2-Pentanol

p39 p40 p40a

3-Pentanol -Pentanolactone -Pentanolactone

p26

193.07

Refractive index

Pentafluorobenzonitrile Pentamethylbenzene 1,2,3,4,5-Pentamethylcyclopentadiene 1,5-Pentamethylenetetrazole Pentanal

p24 p25

C6F5CN

Density

Melting point

54.4

Boiling point

Flash point

185–190

29

231 5813mm

44

Solubility in 100 parts solvent

v s alc, bz

59–61

19412mm

1.394220

92

102–103

12

0.626220 4 0.87325 4 0.994120 0.957 0.972125

1.357520 1.459120 1.449420 1.406820 1.451020

129.7 129.7 15.6 52 23.1

36.1 178–180 242.5 110–112 140.6

49 62 125 19 40

2, 301 43, 23

0.803515 4

1.399115

96.8 300

141.3

40

104.22 102.13 88.15

1, 384 2, 299 1, 383

0.840 0.939020 4 0.814820 4

1.446020 1.408020 1.410020

75.7 33.7 78.9

126.6 185.5 137.8

18 88 32

CH3CH2CH2CH(OH)CH3

88.15

1, 384

0.839320 4

1.406420

glass

119.0

40

CH3CH2CH(OH)CH2CH3

88.15 100.12 100.12

1,385 17, 235 17, 235

0.815025 4 1.057 1.079

1.407925 1.4330 1.457520

69 31

115.6 207–208 600.5mm

40 81 100

1.4 aq; misc alc, eth misc alc, eth s aq, alc; sl s eth s aq, alc; sl s eth 17 aq; misc alc, eth i aq; s alc, eth 4 aq i aq; misc alc, eth 2.4 aq; v s alc, eth 2.7 aq; misc alc, eth 16.6 aq; misc alc, eth 5.2 aq; s alc, eth

86.13

1, 676

0.809520

1.3903

77.8

101.7

7

CH3CH2COCH2CH3 C6H5CO(CH2)3CH3 CH3CH2CH2CH2COCl [ ˆ CH2CH2O ˆ ]5

86.13 162.23 120.58 220.27

1, 679 7, 327 2, 301

0.814320 0.988 1.016

1.392320 1.514320 1.421620 1.461520

39.0

102.0 1075mm 125–127 1350.2mm

12 102 23

CH3O(CH2CH2O)4CH2CH2OH CH3CH2CH2CH ¨ CH2 CH3CH2CH ¨ CHCH3 CH3CH2CH ¨ CHCH3 H2C ¨ CHCH2CH2COOH CH3CH ¨ CHCOCH3 CH3(CH2)4OOCCH3 CH3(CH2)4NH2

252.31

0.933

1.450020

70.14 70.14 70.14 100.11 84.12 130.19 87.17

1, 210 1,210 1, 210 2, 425 1, 732 2, 131 4, 175

0.641020 4 0.648220 4 0.650320 4 0.984318 4 0.862420 4 0.875320 0.752

1.371420 1.379320 1.383020 1.434118 1.440520 1.402820 1.411020

165.2 140.2 151.4 18

CH3(CH2)4C6H5

148.25

5, 434

0.859420 4

1.488520

p41

2-Pentanone

CH3CH2CH2COCH3

p42 p43 p44 p45

p47 p48 p49 p50 p51 p52 p53

3-Pentanone Pentanophenone Pentanoyl chloride 1,4,7,10,13-Pentaoxacyclopentadecane 3,6,9,12,15-Pentaoxahexadecanol 1-Pentene (E)-2-Pentene (Z)-2-Pentene 4-Pentenoic acid 3-Penten-2-one Pentyl acetate Pentylamine

p54

Pentylbenzene

p46

Pentalin, p9 pentamethylene glycol, p30 Pentamethylene oxide, t76 Pentamethylethyl alcohol, t338

1,5-Pentanedicarboxylic acid, h8 Pentanedinitrile, g14 Pentanedioic acid, g11 2,5,8,11,14-Pentaoxapentadecane, b190

misc acet, bz, eth, PE 3.4 aq s alc, eth

1330.005mm 112

100 55

30.0 36.3 36.9 187–189 121–124 149.2 104

21 23 4

78.3

202.2

65

Penetetic acid, d299 sec-Pentylamine, a251 tert-Pentylamine, d601

45

misc alc, bz, eth misc alc, eth misc alc, eth sl s aq; s alc, eth s aq 0.17 aq v s aq; misc alc, eth s alc; misc bz, eth

1.333

1.334

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. p55

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

168.28

73, 173

0.920

1.467720

164.25

6, 548

0.96220 4

68.11 150.22 76.05

1, 250 7, 158

0.690120 4 0.964520 4 15 1.2264

Melting point

12516mm

p56

4-tert-Pentylcyclohexanone 4-tert-Pentylphenol

p57 p58 p59

1-Pentyne L-Perillaldehyde Peroxyacetic acid

p60

Petroleum ether

p61

Phenanthrene

178.23

5, 667

1.17925

100

p62

208.22

7, 796

1.4054

209–211

p63 p64

9,10-Phenanthrenedione 1,10-Phenanthroline Phenol

180.21 94.11

23, 227 6, 110

1.057641 4

p65 p66

Phenolphthalein Phenothiazine

318.33 199.28

18, 143 27, 63

p67

Phenothiazine-10carbonyl chloride Phenoxyacetic acid

261.73

27, 66

168–171

C6H5OCH2COOH

152.15

6, 161

98

C6H5OCH2COCl

170.60

6, 162

C6H5OC6H4NH2

185.23

13, 438

p68 p69 p70

Phenoxyacetyl chloride p-Phenoxyaniline

CH3CH2C(CH3)2C6H4OH CH3CH2CH2C ˜ CH CH3C( ¨ O)OOH

principally pentanes and hexanes

C6H5OH

1.385220 1.507220

1.235

Solubility in 100 parts solvent

104

262.2

s alc, eth

105.7

40.2 10510mm 95 105 explodes 110 35–80 40

v s alc; misc eth

0.640

1.29925 4

Flash point

93

0.1

1.541841

Boiling point

117 40.9

340

181.8

258–262 185.1 371

1.534020

285 sl d 225–256

82–84

18914mm

79

v s aq, alc, eth

misc bz, chl, eth, CCl4 1.6 alc; 50 bz; 30 eth s bz, eth, hot alc 1.4 bz; s alc, acet 6.7 aq; 8.2 bz; v s alc, chl, eth, alk 8.2 alc; 1 eth v s bz; s eth; sl s alc

1.3 aq; v s alc, bz, HOAc, CS2, eth d aq, alc; s eth s hot aq; v s alc, eth

p71 p72 p73 p74 p75

2-Phenoxybutyric acid 2-Phenoxyethanol 1-Phenoxy-2-propanol Phenoxy-2-propanone DL-2-Phenoxypropionic

Peracetic acid, p59 Perdeuterocyclohexane, c313 Perylene, d49 Phenacetin, e45 Phenacyl bromide, b221 Phenacyl chloride, c28

CH3CH2CH(OC6H5)COOH C6H5OCH2CH2OH C6H5OCH2CH(OH)CH3 C6H5OCH2COCH3 CH3CH(OC6H5)COOH

180.20

6, 163

138.17 152.19 150.18 166.18

6, 146 61, 85 6, 151 6, 163

79–83 1.10222 4 1.063254 1.097

9,10-Phenanthraquinone, p62 Phenazone, a309 1,2,4-Phenenyl triacetate, t193 Phenethyl alcohol, p113 sec-Phenethyl alcohol, m138 Phenethylamine, p114

1.537020 1.52320 1.521020

14 13–18

258

245.2 240 230 116–119 265

sl s aq 110 135 85

Phenethyl bromide, b283 Phenethyl chloride, c108 p-Phenetidine, e24 Phenetole, e28 Phenoxyacetone, p74 4-Phenoxybutyl bromide, b243

s aq; v s alc, eth

s alc; sl s aq

1.335

1.336

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. p76 p76a p77

p78 p79 p80 p81 p82 p83 p84 p85 p86 p87 p88 p89 p90 p91 p92 p93

Name 3-Phenoxytoluene Phenylacetaldehyde 2-(2-Phenylacetamido)acetaldoxime Phenyl acetate Phenylacetic acid Phenylacetonitrile Phenylacetyl chloride Phenylacetylene Phenylacetylurea L-3-Phenyl-alanine 2-(Phenylamino)benzoic acid Phenyl 4-aminosalicylate p-Phenylazoaniline Phenylazoformic acid 2-phenylhydrazide p-Phenylazophenol 2-Phenylbenzimidazole Phenyl benzoate N-Phenylbenzylamine 1-Phenylbiguanide

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

C6H5OC6H4CH3 C6H5CH2CHO C6H5CH2CONHCH2CH ¨ NOH

184.24 120.15 192.22

6, 377 7, 292

1.051 1.02725 25

1.572720 1.527320

271–273 33–34 195 147–151

112 86

C6H5OOCCH3 C6H5CH2COOH C6H5CH2CN C6H5CH2COCl

136.15 136.15 117.15 154.60

6, 152 9, 431 9, 441 9, 436

1.07320 4 1.09177 4 1.021415 15 1.169

1.503020

C6H5C ˜ CH C6H5CH2CONHCONH2 C6H5CH2CH(NH2)COOH

102.14 178.19 165.19

5, 511

0.930020 4

1.547020

14, 495

44.9 142.4 212–216 d 283

C6H5NHC6H4COOH

213.24

14, 327

185 d

misc alc, eth sl s alc, bz, chl, eth 3 aq; s hot alc; i eth s hot alc

H2NC6H3(OH)COOC6H5

229.24

153

0.7 mg aq

C6H5N ¨ NC6H4NH2 C6H5N ¨ NCONHNHC6H5

197.24 240.27

161, 310 16, 24

v s alc, bz, chl, eth

C6H5N ¨ NC6H4OH

198.23 194.24

16, 96 23, 230

128 360 156– 159 d 155–157 23020mm 291

C6H5COOC6H5 C6H5CH2NHC6H5 C6H5NHC( ¨ NH)NHC( ¨ NH)NH2

198.22 183.25 177.21

9, 116 12, 1023

Formula

1.235 1.061

1.523320 1.532520

76.5 23.8

196 265.5 233.5 9512mm

70 314 27–38 306–307 144–146

76 101

31

Solubility in 100 parts solvent

sl s aq; s alc, eth

misc alc, eth, chl s hot aq, alc, eth i aq; misc alc, eth d aq, alc

v s alc, eth s abs alc; sl s bz, chl v s hot alc; sl s eth s alc, chl, eth v s aq, alc

p94

1-Phenyl-2-butanone

CH3CH2COCH2C6H5

148.21

7, 314

0.998

1.512220

p95 p96

4-Phenyl-2-butanone (E)-4-Phenyl-3buten-2-one 4-Phenylbutylamine

C6H5CH2CH2COCH3 C6H5CH ¨ CHCOCH3

148.21 146.19

7, 314 7, 364

0.989 1.009745 4

1.512220 1.583645

C6H5CH2CH2CH2CH2NH2 CH3C(OH)(C6H5)C ˜ CH

149.24

12, 1165

0.944

1.519620

146.19

62, 559

51–52

217–218

CH3CH2CH(C6H5)COOH C6H5CH2CH2CH2COOH CH3CH2CH(C6H5)CN

164.20 164.20 145.21

92, 356 9, 539 9, 541

42–44 50–52

C6H5OOCCl C6H5SCOCl

156.57 172.6

270–272 16510mm 114– 112 11515mm 719mm 10110mm 116

p97 p98 p99 p100 p101 p102 p103

2-Phenyl-3-butyn2-ol 2-Phenylbutyric acid 4-Phenylbutyric acid DL-2-Phenylbutyronitrile Phenyl chloroformate S-Phenyl chlorothioformate

Phenylacetaldehyde dimethyl acetal, d450 N-Phenylacetamide, a18 Phenylacetone, p144 2-Phenylacetoacetonitrile, a51 -Phenylacetophenone, d22 -Phenylacrylic acid, c267 -Phenylallyl alcohol, c270 o-Phenylanisole, m56

0.974

1.508620

1.26930 4

1.578630

N-Phenylanthranilic acid, p85 Phenylarsonic acid, b11 Phenylazoformic acid 2-phenylhydrazide, d660 N-Phenylbenzamide, b5 Phenylbenzene, b134 Phenylbenzoic acid, b135 p-Phenylbenzyl alcohol, b138 Phenylboric acid, b12

41.5

14

11215mm

90

235 261

98 65

12417mm

101

s alc; misc eth; i aq s alc, eth v s alc, bz, chl, eth

0.8 aq; s alc, bz, acet s bz, eth s alc, eth

1-Phenylbutane, b423 2-Phenylbutane, b424 1-Phenyl-1,3-butanedione, b64 4-Phenyl-sec-butyl acetate, m361 Phenyl Cellosolve, p72 Phenyl chloride, c41

1.337

1.338

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. p104 p105 p106 p107 p108 p109 p110 p111 p112 p113 p114 p115 p116 p117 p118 p119

Name Phenylcyclohexane Phenyl dichlorophosphate N-Phenyldiethanolamine o-Phenylenediamine m-Phenylethanol p-Phenylenediamine o-Phenylene phosphorochloridite 1-Phenyl-1,2ethanediol 1-Phenylethanol 2-Phenylethanol 2-Phenylethylamine D-()--Phenylglycine 1-Phenylheptane 1-Phenylhexane Phenylhydrazine

Phenyl 3-hydroxy-2naphthoate p119a 2-Phenyl-2imidazoline p120 2-Phenylindole p121 Phenyl isocyanate p122 Phenyl isothiocyanate

Formula weight

Beilstein reference

Density

Refractive index

Melting point

C6H5C6H11 C6H5OP(O)Cl2

160.26 210.98

5, 503 6, 179

0.942720 1.412

1.526320 1.523020

C6H5N(CH2CH2OH)2

181.24

12, 183

1.12060 20

C6H4(NH2)2 C6H4(NH2)2 H2NC6H4NH2

108.14 108.14 108.14 174.52

13, 6 131, 10 13, 61 27, 809

C6H5CH(OH)CH2OH

138.17

6, 907

CH3CH(C6H5)OH C6H5CH2CH2OH C6H5CH2CH2NH2 C6H5CH(NH2)COOH

122.17 122.17 212.28 151.17

6, 475 6, 478 12, 1096 14, 460

1.015020 20 1.01825 25 0.964025 4

C6H5(CH2)6CH3 C6H5(CH2)5CH3 C6H5NHNH2

176.30 162.28 108.14

5, 451 52, 337 152, 44

0.860 0.861 1.097820 4

C10H6(OH)COOC6H5

264.28

10, 335

129–132 261160mm

146.19

23, 154

94–99

193.25 119.12 135.19

20, 467 12, 437 12, 453

Formula

C6H5NCO C6H5NCS

1.13915 15 1.466

1.571220

1.521120 1.531720 1.533220

Boiling point

Flash point

7.0

240.1 241–243

98 112

56–58

350 sl d

103–104 256–258 62–63 234–237 145–147 267 8020mm

68 112

66–68

272–274

21.4 27

203.9 221 195

102 90

233 226 243.5 d

95 83 88

Solubility in 100 parts solvent v s alc, eth

5 aq; v s alc; 29 eth; 25 bz v s alc, chl, eth s aq, alc, acet, chl 1 aq; s alc, chl, eth

v s aq, alc, bz, eth, chl, HOAc 2.3 aq 2 aq; misc alc, eth s aq; v s alc, eth

305–310

1.095620 4 1.128825 4

1.484220 1.486520 1.607020

1.535020 1.649720

61 19.5

17 30 21

25010mm 162–163 221

55 87

misc eth misc alc, bz, chl, eth

d aq, alc; s eth i aq; s alc, eth

p123 p124 p125

N-Phenylmaleimide Phenylmalonic acid Phenylmercury(II) acetate p126 Phenylmercury(II) chloride p127 Phenylmercury(II) hydroxide p128 Phenylmethanethiol p129 N-Phenylmorpholine p130 N-Phenyl-1naphthylamine p130a 1-Phenyloctane p131 2-Phenylphenol p132 4-Phenylphenol 2-Phenylcinchoninic acid, p149 -Phenyl-o-cresol, h113 Phenylethane, e68 Phenylethanenitrile, p80 1-Phenylethanol, m138 Phenylethanolamine, a262

C6H5CH(COOH)2 C6H5HgOOCCH3

173.17 180.16 336.74

21, 400

89–90 155 d 149

C6H5HgCl

313.15

C6H5HgOH

294.70

16, 952

C6H5CH2SH

6, 453 27, 6 12, 1224

1.05820

C10H7NHC6H5

124.21 163.22 219.29

C6H5(CH2)7CH3 C6H5C6H4OH C6H5C6H4OH

190.33 170.21 170.21

5, 453 62, 623 6, 674

0.857220 4 1.213

16312mm

s alc, chl, eth 0.17 aq; s alc, bz, acet s bz, eth, pyr

250–252 190 d

57 60–62

N-Phenylethanolamine, a300 Phenylethene, s11 N-Phenylformamide, f31 Phenylglyoxylic acid, b70 Phenylglyoxylonitrile, b68

1.484020

194–195 268 22615mm

36 261–263 57 282 164–165 305

70 1.0 aq; v s hot alc s alc, bz, chl, eth 107 123 165

misc eth s alc, chl, eth, alk s alc, chl, eth, alk

1-Phenyl-1-hydroxy-2-methylaminopropanes, e1, e2 2,2-(Phenylimino)diethanol, p106 p-(2-Phenylisopropyl)phenol, m359 Phenyl--methylstyryl ketone, d658 1-Phenylpentane, p54

1.339

1.340

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. p133 p134

p135 p136 p137 p138 p139 p140 p141 p142 p143 p144 p145 p146

p147

Name N-phenyl-p-phenyl enediamine Phenyl N-phenylphosphoramidochloridate Phenylphosphinic acid Phenylphosphonic acid Phenylphosphonic dichloride Phenylphosphonothioic dichloride N-Phenylpiperazine 2-Phenyl-1,2propanediol 3-Phenyl-1-propanol propanethiol 1-Phenyl-1-propanol 3-Phenyl-1-propanol 1-Phenyl-2-propanone 2-Phenylpropionaldehyde 3-Phenylpropionic acid 1-Phenyl-3-pyrazolidinone

Formula weight

Beilstein reference

C6H5NHC6H4NH2

184.24

13, 76

73–75

C6H5NHP( ¨ O)(Cl) OC6H5

267.66

12, 588

132–134

C6H5PH(O)OH

142.09

16, 791

83–85

C6H5P(O)(OH)2

158.09

16, 803

163–166

C6H5P(O)Cl2

194.99

16, 804

1.375

1.560020

C6H5P(S)Cl2

211.05

16, 807

1.360

1.624420

162.24 152.19

1.062120 4

1.587520

CH3C(C6H5)(OH)CH2OH

6, 930

C6H5CH2CH2CH2SH

152.26

61, 253

1.010

1.549420

C6H5CH(OH)CH2CH3 C6H5CH2CH2CH2OH C6H5CH2COCH3

136.19 136.19 134.18

6, 502 6, 503 72, 233

0.991525 4 1.008 1.015720 4

1.516923 1.525720 1.516020

CH3CH(C6H5)CHO

134.18

72, 237

1.00920 4

1.517520

C6H5CH2CH2COOH

150.18

9, 508

1.047100 4

162.19

24, 2

Formula

Density

Refractive index

Melting point

3

Boiling point

258

Flash point

Solubility in 100 parts solvent

112

205130mm 286 112 160– 112 16226mm 10910mm 90

i aq; misc alc

44–45

18 27

219 235 10013mm

109 84

202–205

69

misc alc, bz s aq; misc alc, eth v s alc, eth; misc bz i aq; s alc

47–48

121

280

0.6 aq; s bz, alc, chl, eth, HOAc, PE 10 hot aq; hot alc; s alk, acid

p148 p149

p150

p151 p152 p153 p154 p155

2-Phenylpyridine 2-Phenyl-4quinolinecarboxylic acid Phenyl salicylate

C6H5C5H4N

Phenylselenenyl chloride Phenylsuccinic acid S-Phenyl thioacetate 1-Phenyl-2thiourea Phenyltrichlorosilane

1.624220

155.20 249.27

20, 424 22, 103

C6H4(OH)COOC6H5

214.22

10, 76

C6H5SeCl

191.52

HOOCCH2CH(C6H5)COOH C6H5SCOCH3

194.19

C6H5NHC(S)NH2

152.22

12, 388

1.3

C6H5SiCl3

211.56

16, 911

1.32920

2-Phenylpropane, i91 3-Phenyl-2-propenoic acid, c267 3-Phenyl-2-propen-1-o1, c270 3-Phenyl-2-propenoyl chloride, c268 3-Phenylpropyl alcohol, p143 Phenyl propyl ketone, b500

268–270

112

214–215

41–43

17312mm

63, 1110

63–65

12020mm

9, 865

167–169 H2O, 168 1006mm

1.25

1.572020

152.22

3-Phenylpropyl mercaptan, p141 Phenyl sulfide, d688 Phenyl sulfone, d689 Phenylsulfonic acid, b22 Phenyl sulfoxide, d690 (Phenylthio)acetic acid, t160

17 alc; 66 bz; s acet, chl, eth; 0.015 aq

s hot aq, alc, eth 79

154 1.523020

s alc, eth 0.8 alc; 1 eth; 0.3 chl

0.25 aq; s alc, alk 201

91

Phenyl thiocarbamide, p154 -Phenyl-o-toluic acid, b84 Phenyl m-tolyl ether, p76 Phenyl trifluoromethyl ketone, t289

1.341

1.342

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. p156 p157 p158 p159

p160 p161 p162

p163 p164 p165 p166

Name 1-Phenyltridecane Phenyltriethoxysilane Phenyltrimethoxysilane Phenyltrimethylammonium bromide Phenyltrimethylammonium chloride Phenyltrimethylammonium iodide Phenyltrimethylammonium tribromide Phenyltrimethylsilane Phenyltris(trimethylsiloxy)silane Phenylurea

p167

Phenylvinyldichlorosilane o-Phthalic acid

p168 p169 p170

Phthalic anhydride Phthalide Phthalimide

p171

o-Phthaloyl dichloride

Formula weight

Beilstein reference

Density

Refractive index

Melting point

C6H5(CH2)12CH3 C6H5Si(OC2H5)3

260.47 240.38

0.855520 4 0.996

1.481420 1.460420

10

16, 911

C6H5Si(OCH3)3

198.3

1.06420 4

1.473420

[C6H5N(CH3)3]Br

216.13

122, 88

210 d

v s aq; s hot alc

[C6H5N(CH3)3]Cl

171.67

12, 158

237 subl

[C6H5N(CH3)3]I

263.12

122, 88

175

s aq; v s alc; sl s chl s aq, alc; sl s acet

C6H5N(CH3)3]Br 3

375.95

C6H5Si(CH3)3 [(CH3)3SiO]3SiC6H5

150.30 372.8

161, 525

0.873 0.97025 4

C6H5NHCONH2

136.15

12, 346

1.302

H2C ¨ CH(C6H5)SiCl2

203.2

C6H4(COOH)2

166.13

9, 791

1.59320 4

206–208

148.12 134.13 147.13

17, 469 17, 310 21, 458

1.53 1.16499 4

130.8 72–74 238

285 subl 290 subl

203.02

9, 805

1.40920

15–16

280–282

Formula

C6H4(COCl)2

Boiling point 346 1131.0mm

Flash point

Solubility in 100 parts solvent

 112 42

211

114–116

1.19625 4

1.490720 1.45925

168–170 264–266

44 121

145–147 238 1.53425

1.568420

s hot aq, hot alc, eth

871.5mm

 112

0.6 aq; 10 alc; 0.5 eth; v sl s chl 0.6 aq(d); s alc s alc v s alk; v sl s bz, PE d aq, alc; s eth

p172 p173

Phthalylsulfathioazole Picric acid

p174 p175 p176 p177 p178

Pinane ()--Pinene ()--Pinene -Pinene oxide -Pinene oxide

Phloroglucinol, t305 Phorone, d529 Phthalaldehydic acid, f33 m-Phthalic acid, b16 p-Phthalic acid, b17 Phthalonitrile, d236

403.44 (O2N)3C6H2OH

229.11

6, 265

1.76320 4

138.3 136.24 136.24 152.24 152.24

5, 93 5, 146 5, 154 5, 152 172, 44

0.83920 4 0.859120 4 0.859020 0.964 0.976

Picolinaldehyde, p251 Picolines, m398, m399, m400 Picolinic acids, p255, p257 Picolinonitrile, c295 Picolylamines, a223, a224 Picramide, t381

1.461620 1.466020 1.466620 1.469020 1.476520

272 d

s alk; sl s alc; i chl

122–123 explodes  300

1.3 aq; 8.2 alc; 10 bz; 2.9 chl; 1.6 eth

50 55 61.5

167–168 155–156 166 10350mm 10027mm

32 32 65 66

Pimelic acid, h8 Pinacol, d491 Pinacolone, d497 Pinacolyl alcohol, d496 3-Pinanol, i83

misc alc, eth

1.343

1.344

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. p179 p180 p181 p182 p183 p184

Name

Formula

Piperazine 1-Piperazinecarbaldehyde 1,4-Piperazinedicarbonitrile 3-(1-Piperazinyl)1,2-propanediol Piperidine

Formula weight

Beilstein reference

86.14 114.15

23, 4

136.16

231, 5

Density

Refractive index

Melting point

1.107

1.446113 1.509420

108–110 145–146 970.5mm

160.22 85.15

20, 6

0.865915

1.452520

110.16

20, 56

0.951

1.470520

129.20 129.20 115.18 138.21

20, 25 21, 2 212, 8

0.973225 25 1.01017 1.026 0.933

1.480420

159.23

20, 34

154.3 44.10

1, 104

0.917825 1.472920 0.584242 1.339742

p190 p191

CH3CH2CH3

p192

1,2-Propanediamine

CH3CH(NH2)CH2NH2

74.13

4, 257

0.87815

1.446020

p193 p194

1,3-Propanediamine 1,2-Propanediol

H2NCH2CH2CH2NH2 CH3CH(OH)CH2OH

74.13 76.10

4, 261 1, 472

0.88425 4 1.036420 4

1.457520 1.433120

p195

1,3-Propanediol

HOCH2CH2CH2OH

76.10

1, 475

1.059720 4

1.439620

p189

Flash point

Solubility in 100 parts solvent

109 101

v s aq; 50 alc; i eth

misc aq; s alc, bz, chl

167–170

1-Piperidinecarbonitrile N-Piperidineethanol 2-Piperidineethanol 3-Piperidinemethanol 1-Piperidinepropionitrile 3-Piperidino-1,2propanediol trans-Piperitol Propane

p185 p186 p187 p188

Boiling point

73–77

1330.1mm

10.5

106.4

4

10210mm

97

200–202 234 1073.5mm 11116mm

68 102  112

38–40 1.469520

misc aq; s alc v s aq, alc, eth

77–80 187.7

42.1

119.7

33

12 60

140 188

48 107

26.7

214.4

79

6.5 mL aq; 790 mL alc; 926 mL eth; 1300 mL chl; 1450 mL bz misc aq, bz; s alc, eth misc alc, eth; s aq misc aq, acet, chl; s alc, eth misc aq, alc

p196

1,3-Propanedithiol

HSCH2CH2CH2SH

108.23

1, 476

1.077220 4

p197

1-Propanesulfonyl chloride 1,3-Propane sultone

CH2CH2CH2SO2Cl

142.60

4, 8

1.286415 4

p198

Pipecolines, m369, m370, m371 1-Piperazineethanol, h123 1-Piperidinecarboxyaldehyde, f35 Piperonal, m239 Piperonyl alcohol, m242 Piperonyl butoxide, m243 Piperonylic acid, m241 Pivalaldehyde, d596

122.14

1.392

Pivalamide, d597 Pivalic acid, d598 Pivalic anhydride, d599 Pivaloyl chloride, d600 Pivaloyloxymethyl chloride, c151 POPOP, b198 PPO, d679 Prehnitene, t97

1.540520

79

169 668mm

30–33

40

misc alc, bz, eth, chl d hot aq, hot alc

18030mm

Procaine, d271 Proline, p273 Propadiene, a78 1-Propanal, p211 1,3-Propanedicarboxylic acid, g11 Propanedioic acid, m3 1,2-Propanediol cyclic carbonate, p225

1.345

1.346

TABLE 1.15 Physical Constants of Organic Compounds (continued ) Beilstein reference

Density

Refractive index

Melting point

76.16 76.16

1, 359 1, 367

0.83625 4 0.80925 4

1.438020 1.425520

113.1 130.5

67.7 52.6

20 34

218.21

2, 147

1.59620 4

1.430220

78

258–260

148

60.10 60.10

1, 350 1, 360

0.803720 4 0.785520 4

1.385620 1.377220

126.2 89.5

97.2 82.4

15 22

56.07 42.08

1, 725 1, 196

0.838920 1.401720 1.356740 0.610448 4

87.0 185.2

52.7 47.7

18

74.15 174.11

1, 440 2, 849

0.92523 4

67–68

21

97

18

Name

p199 p200

1-Propanethiol 2-Propanethiol

CH3CH2CH2SH CH3CH(SH)CH3

p201 p202 p203

1,2,3-Propanetriol triacetate 1-Propanol 2-Propanol

H3CCOOCH(CH2OOCCH3)2 CH3CH2CH2OH (CH3)2CHOH

p204 p205

2-Propenal Propene

H2C ¨ CHCHO H2C ¨ CHCH3

p206 p207

H2C ¨ CHCH2SH

H2C ¨ C(OOCCH3)CH3

100.12

p209 p210

2-Propene-1-thiol (Z)-1,2,3-Propenetricarboxylic acid 1-Propen-2-yl acetate o-Propenylphenol -Propiolactone

CH3CH ¨ CHC6H4OH

134.18 72.06

61, 279

p211

Propionaldehyde

CH3CH2CHO

58.08

p212 p213

Propionamide Propionic acid

CH3CH2CONH2 CH3CH2COOH

p214 p215

Propionic anhydride Propionitrile

[CH3CH2C( ¨ O)]2O CH3CH2CN

p208

Formula

Formula weight

No.

Boiling point

Flash point

d 200 0.909

1.400020

1.044 1.146020 4

1.575420 1.413120

33.4

230–231 162.3

90 70

1, 629

0.807120 4

1.364619

81

48–49

9

73.10 74.09

2, 243 2, 234

0.959720 4 0.993420 4

1.4160110 1.386520

79 21

222.2 140.8

51

130.14 55.08

2, 242 2, 245

1.012520 4 0.781820 4

1.404720 1.365820

45 92.8

167 97.2

73 6

Solubility in 100 parts solvent s alc, eth misc alc, eth; sl s aq 7.2 aq; misc alc, bz, chl, eth misc aq, alc, eth misc aq, alc, chl, eth 21 aq; s alc, eth 45 mL aq; 1200 mL alc; 500 mL acet misc alc, eth 50 aq; s alc; sl s eth

37 aq(hyd); misc alc (reacts), bz, eth, acet 30 aq; misc alc, eth v s aq, alc, chl, eth misc aq; s alc, chl, eth d aq; s alc, chl, eth 10 aq; misc alc, eth

1.405120 1.525820

0.76820 4

1.38420

2, 129

0.83620 4

1.384420

92

59.11 103.17

4, 136 4, 282

0.717320 0.900

1.388220 1.441520

120.20 164.20 126.24 102.09 57.09

5, 390 9, 112 52, 23

0.862120 4 1.023220 0.792920 4 1.204120 4 0.801725

1.491220 1.500320 1.437020 1.421020 1.408425

Propionyl chloride Propiophenone

CH3CH2COCl C6H5COCH2CH3

92.53 134.18

p218

Propoxytrimethylsilane Propyl acetate

CH3CH2CH2OSi(CH3)3

132.3

CH3CH2CH2OOCCH3

102.13

CH3CH2CH2NH2 C3H7NHCH2CH2OH CH3CH2CH2C6H5 C6H5COOCH2CH2CH3 CH3CH2CH2C6H11

p219 p220 p221 p222 p223 p224 p225 p226

Propylamine 2-(Propylamino)ethanol Propylbenzene Propyl benzoate Propylcyclohexane Propylene carbonate Propyleneimine

1,2,3-Propanetriol, g16 Propanetriol diacetates, g17, g18 2-Propanone, a26 Propargyl alcohol, p242 Propargyl chloride, c232 Propenamide, a62 2-Propenenitrile, a64 2-Propenoic acid, a63

94 18.6

1.06520 4 1.010520 4

p216 p217

2, 243 72, 231

2-Propen-1-o1, a81 2-Propenyl acetate, a80 Propenylanisole, m97 N-2-Propenyl-2-propen-1-amine, d25 (2-Propenyl)thiourea, a101 Propiolic acid, p241 Propyl chloride, c210 Propylene, p205

80 218.0

11 87

d aq, alc misc bz, eth, abs alc

101.6

12

83.0

47.9 182746mm

37 78

2.3 aq; misc alc, eth misc aq, alc, eth

99.6 51.6 94.9 55

159.2 231.2 156.7 240 66.0

47

100735mm

132

s alc, eth i aq; s alc, eth s bz, eth v s aq, alc, bz, eth misc aq, alc, PE

Propylene dibromide, d92 sec-Propylene chlorohydrin, c213 Propylenediamine, p192 Propylene glycol, p194 Propylene glycol isopropyl ether, i86 Propylene glycol monomethyl ether, m95 Propylene glycol monophenyl ether, p73

1.347

1.348

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

p227

Propylene oxide

p228

Propylene sulfide

p229 p230

Propyl formate Propyl 4-hydroxybenzoate Propyl isocyanate Propyl lactate Propyl nitrate

p231 p232 p233 p234 p235 p236

p240

2-Propylpentanoic acid o-Propylphenol Propylphosphonic dichloride Propyltrichlorosilane Propyltriethoxysilane Propyl 3,4,5-trihydroxybenzoate Propyne

p241 p242

2-Propynoic acid 2-Propyn-1-ol

p243

()-Pulegone

p237 p238 p239

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

58.08

17, 6

0.828720

1.366020

112.1

37–38

37

CH3CHˆCH2 O CH3CHˆCH2 S CH3CH2CH2OOCH HOC6H4COOCH2CH2CH3

102.18

1, 354

0.736

1.380020

123

88–90

4

88.10 180.20

2, 21 10, 160

0.900620 4

1.376920

92.9 86–87

80.9

3

CH3CH2CH2NCO CH3CH(OH)COOC3H7 CH3CH2CH2ONO2

85.11 132.16 105.09

41, 366 3, 265 1, 355

0.908 0.99620 20 1.053820 4

1.397020 1.416725 1.397620

(CH3CH2CH2)2CHCOOH CH3CH2CH2C6H4OH CH3CH2CH2P(O)Cl2

144.21 136.19 160.97

2, 350 6, 499 4, 596

0.921 1.01520 1.290

1.425020 1.527920 1.464320

83–84 26 8640mm 100 110.1 23 may explode on heating 220 224–226 93 88–9050mm 112

CH3CH2CH2SiCl3

177.53

4, 630

1.185120 4

1.42920

123–124

0.89220 4

1.39620

179–180

C3H7Si(OC2H5)3

206.4

(HO)3C6H2COOC3H7

212.20

Solubility in 100 parts solvent 41 aq; misc alc, eth

2 aq; misc alc, eth 0.05 aq; v s alc, eth

s aq, alc, eth s alc, eth

s alc, eth

2

150

CH3C ˜ CH

40.06

1, 246

0.69120 4

1.372520

102.8

23.2

HC ˜ CCOOH HC ˜ CCH2OH

70.05 56.06

2, 477 1, 454

1.13820 4 0.971520 4

1.432020 1.432020

9 51.8

102200mm 113.6

58 33

152.24

7, 81

0.934615 4

1.485020

224

82

0.35 aq; 1 alc; 83 eth v s alc; 3000 mL eth s aq, alc, eth misc aq, alc, bz, chl misc alc, chl, eth

p244 p245 p246 p247

Pyrazine Pyrazole Pyrene Pyridazine

p248 p249 p250 p251

Pyridine Pyridine-d5 2-Pyridinealdoxime 2-Pyridinecarbaldehyde 3-Pyridinecarbaldehyde 4-Pyridinecarbaldehyde 3-Pyridinecarbamide Pyridine-2-carboxylic acid Pyridine-3-carboxylic acid

p252 p253 p254 p255 p256

Propylene oxide, e10 Propyl gallate, p239 Propyl iodide, i48 Propyl mercaptan, p199

80.09 68.08 202.26 80.09

23, 91 23, 39 5, 693 23, 89

1.03161 4

1.495361 1.4203

1.103525 4

1.523023

C5H5N C5D5N (C5H4N)CH ¨ NOH (C5H4N)CHO

79.10 84.14 122.13 107.11

20, 181

0.978225 4 1.05

1.506725 1.507920

211, 288 211, 287

1.126

(C5H4N)CHO

107.11

211, 288

(C5H4N)CHO

107.11

(C5H4N)CONH2 (C5H4N)COOH (C5H4N)COOH

53 115–116 70 186–188 150–151 8 208 41.6

v s aq, alc, eth s aq, alc, bz, eth 85

115.2 114.4

20 20

1.537020

181

54

1.135

1.549320

9715mm

60

21, 287

1.172

1.544020

7812mm

54

122.13 123.11

22, 40 22, 33

1.400

1.466

123.11

22, 38

1.473

6-Propyl-2-thiouracil, h129 Protocatechualdehyde, d376 Pseudocumene, t334 Pyrene, b52

misc aq, bz; v s alc, eth misc aq, alc, eth

110–112

s aq, eth

130–133 134–136 subl

100 aq; 66 alc s aq, alc, bz

236.6

1.4 aq; s alk

subl

3,6-Pyridazinediol, d400 2.3-Pyridinediol, d401

1.349

1.350

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. p257 p258 p259 p260 p261 p262 p263 p264 p265 p266 p267 p268 p269 p270 p271

p272

Name Pyridine-4-carboxylic acid 4-Pyridinecarboxylic hydrazide 2,3-Pyridinedicarboxylic acid 2,5-Pyridinedicarboxylic acid 2,6-Pyridinedicarboxylic acid Pyridine-N-oxide 3-Pyridinesulfonic acid 2-Pyridylmethanol 3-Pyridylmethanol 3-(3-Pyridyl)-1propanol Pyrimidine 2,4(1H,3H)-Pyrimidinedione Pyrrole Pyrrolidine 1-Pyrrolidinecarbodithioic acid, ammonium salt 1-Pyrrolidinecarbonitrile

Formula weight

Beilstein reference

(C5H4N)COOH

123.11

22, 45

319

(C5H4N)CONHNH2

137.14

221, 504

171.4

(C5H3N)(COOH)2

167.12

22, 150

190 d

0.52 aq; i alc, bz, eth 14 aq; 2 alc; 0.1 chl 0.56 aq; s alk

(C5H3N)(COOH)2

167.12

22, 153

236–237 subl d

s hot acid

(C5H3N)(COOH)2

167.12

22, 154

250 d

sl s aq; v sl s alc

C5H5N(O) (C5H4N)SO3H

95.10 159.16

202, 131 22, 387

66 300

(C5H4N)CH2OH (C5H4N)CH2OH (C5H4N)CH2CH2CH2OH

109.13 109.13 137.18

211, 203 21, 50

1.131 1.124 1.045

1.542020 1.544520 1.529520

80.09 112.09

23, 89 24, 312

1.016

1.503520

20–22 335

123–124

31

misc aq; s alc, eth 0.3 aq; s alk

67.09 71.12

20, 159 20, 4

0.969120 4 0.852022 4

1.510220 1.443120

23.4 57.8

129.8 88–89

38 2

4.5 aq; v s alc, eth misc aq; s alc, chl, eth

771.8mm

107

Formula

Density

Refractive index

164.29

96.13

Melting point

Boiling point

Flash point

26015mm

270 v s aq 11316mm 15428mm

v s aq, alc, eth v s aq, eth

153–155

0.954

1.469020

Solubility in 100 parts solvent

p273

L-()-2-Pyrrol-

115.13

p274

idinecarboxylic acid 1-Pyrrolidino-1cyclohexene 2-Pyrrolidinone

151.25

p275 p276 q1

3-(N-Pyrrolidino)1,2-propanediol Quinhydrone

Pyridinols, h173, h174, h175 3-Pyridinol N-oxide, h177 2(1H)-Pyridone, h173 2-(2-Pyridyl)pyridine, d705 Pyrocatechol, d377

85.11

22, 2

21, 236

145.20

201, 4

218.20

7, 617

d 220

0.940

1.522520

1.11625 4

1.48625

1.40120 4

Pyrogallol, t304 Pyromellitic acid, b26 Pyromellitic dianhydride, b27 Pyromucic acid, f42 Pyromucic aldehyde, f39

162 aq; 66 abs alc

11515mm

39

25

245

145

46–48

158 30mm

171

misc aq, alc, bz, chl, eth, EtAc

s hot aq, alc, eth

Pyrrolidinedithiocarbamate, p271 Pyruvic acid, o60 Pyruvic aldehyde, o59 Pyruvic aldehyde dimethyl acetal, d451 Quinaldine,

1.351

1.352

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

1.625

177 d

Boiling point

q2

Quinine

324.44

q3

Quinoline

129.16

20, 339

1.09520 4

1.627320

14.9

q4 q5

Quinoxaline Quinuclidine

130.15 111.19

23, 176 20, 144

1.133448 4

1.623148

r1

D-Raffinose

594.52

31, 462

29–30 229.5 156 sealed tube 80 d 118

r2 r3

pentahydrate Rhodamine B Rhodanine

479.02 133.19

19, 346 27, 242

r4 r5 s1

Riboflavin D-()-Ribose Saccharin

376.37 150.13 183.19

11, 434 27, 168

s2

Safrole

162.19

19, 39

s3

Semicarbazide

75.07

3, 98

Quinizarin, d372 Quinolinic acid, p259 8-Quinolinol, h178 p-Quinone, b59 Resacetophenone, d370 Resorcinol, d378 Resorcinol dimethyl ether, d432 Resorcinol monoacetate, d380 Resorcinol sulfide, t145

H2NNHCONH2

-Resorcylaldehyde, d375 -Resorcylic acid, d385 -Resorcylic acid, d383 Ribofuranose, r5 Rosaniline, b2 Rubeanic acid, d710 Slicyl alcohol, h105 Salicylaldehyde, h94 Salicylaldoxime, h97

101

1.537020

11.2

232–234

96 Salicylamide, h98 Salicylanilide, h161 Salicylic acid, h99 Salol, p150 Sarcosine, m258 Sebacic acid, d9 Sebacoyl chloride, d11 Semioxamazide, 053

Solubility in 100 parts solvent 125 alc; 1.2 bz; 83 chl 0.6 aq; misc alc, eth v s aq, alc, bz, eth v s aq, alc, eth

14 aq; 10 MeOH

165 170 may explode on rapid heating d 278 87 229–230

0.868

1.09520

237

Flash point

97

v s aq, alc v s hot aq, alc, eth v s alk(d); i eth s aq; sl s alc 0.34 aq; 3 alc; 8 acet v s alc; misc chl eth v s aq, alc; i eth

1.353

1.354

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Beilstein reference

Density

105.09 182.17

4, 505 1, 533

1.4725

1, 927 11, 72

1.6515 0.810

1.453015

165 38

350

218

s aq; v sl s alc, eth 83 aq; s hot alc, acet 55 aq; v sl s alc s bz, chl, eth, PE

11, 130

0.858420 4

1.496520

75

28525mm

200

v s eth, acet, PE

5, 630 272, 723

0.970 1.3620 4

5, 474 2, 614 2, 614 2, 601

0.906020

s4 s5

L-Serine

s6 s7

L-()-Sorbose Squalane

s8

Squalene

s9 s10

trans-Stilbene L-Strychnine

180.16 [(CH3)2CH(CH2)3422.80 CH(CH3)(CH2)3CH(CH3)CH2CH2 ˆ ]2 {CH3[C(CH3) ¨ CHCH2410.73 CH2]2C(CH3)¨CHCH2 ˆ}2 C6H5CH ¨ CHC6H5 180.25 334.42

s11 s12 s13 s14

Styrene Succinamic acid Succinamide Succinic acid

C6H5CH ¨ CH2 H2NCOCH2CH2COOH H2NCOCH2CH2CONH2 HOOCCH2CH2COOH

104.15 117.10 116.12 118.09

s15

Succinic acid 2,2dimethylhydrazide Succinic anhydride Succinimide Succinonitrile Succinyl chloride Sucrose Sulfamethazine Sulfanilamide

HOOCCH2CH2CONHN(CH3)2

160.17

s16 s17 s18 s19 s20 s21 s22

HOCH2CH(NH2)COOH

Formula weight

D-Sorbitol

NCCH2CH2CN ClCOCH2CH2COCl

H2NC6H4SO2NH2

100.07 99.09 80.09 154.98 342.30 278.34 172.21

Refractive index

Melting point

Boiling point

Flash point

222 d 110–112

124 206–207 284–286 2705mm

1.546820

1.552

30.6 145.1 153–156 260 d 125 subl 187–190 235 d

31

154–155 17, 407 21, 369 2, 615 2, 613 31, 424 14, 698

1.41 0.985 1.39515 4 1.58725 4

1.47315

119.6 125–127 46–48 17 192 d 198–201 164–166

261 287 265–267 192–193

112 76

Solubility in 100 parts solvent

v s bz, eth 6.2 alc; 20 chl; 0.55 bz; 15 mg aq s alc, acet, eth s aq; sl s alc; i eth 0.45 aq; i alc, eth 7.7 aq; 5.4 alc; 2.8 acet; 0.88 eth; i bz 11 aq; 2.5 acet; 5 MeOH s alc, chl; v sl s eth 33 aq; 4 alc; i eth d aq, alc; s bz 200 aq; 0.59 alc 0.15 aq; s alk 0.76 aq; 2.7 alc; 20 acet; s acid, alk

s23 s24 s25

Sulfoacetic acid o-Sulfobenzoic acid cyclic anhydride 4,4-Sulfonylbis(2,6-dibromophenol)

Senecioic acid, m163 Skatole, m284 Sodium tetraphenylborate, t128 Solketal, d515 Sorbic acid, h42 Sorbic aldehyde, h40 Stearamide, o2 Stearic acid, o5

HO3SCH2COOH

140.11 184.17

4, 21 19, 110

84–86

[HO(Br)2C6H2]2SO2

565.88

6, 865

289–292

Stearyl bromide, b319 Styrene dibromide, d79 Styrene glycol, p111 Styrene oxide, e9 Suberic acid, o24 Suberonitrile, d239 Succinic acid monoamide, s12 Succinonitrile, b380

245 d 18618mm

Succinyl dihydrazide, s15 Sulfanilic acid, a120 N-Sulfinylaniline, t152 3-Sulfoalanine, a288 Sulfolane, t106 3-Solfolene, d368 Sulfonyldianilines, d36, d37

s aq, alc; i eth, chl s bz, chl, eth; i aq

1.355

1.356

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. s26 s27 s28 t1 t2 t3 t4 t5 t6 t7 t8 t9 t10 t11 t12 t13 t14 t15

Name 4,4-Sulfonylbis(methyl benzoate) 4,4-Sulfonyldiphenol 5-Sulfosalicyclic acid D-()-Tartaric acid meso-Tartaric acid hydrate Tartrazine p-Terphenyl -Terpinene -Terpinene Terpinen-4-ol Tetraallyloxysilane 1,1,2,2,-Tetrabromoethane Tetrabromophthalic anhydride ,,,-Tetrabromo-o-xylene ,,,-Tetrabromo-m-xylene Tetrabutoxysilane Tetrabutylammonium bromide Tetrabutylammonium chloride

Formula weight

Beilstein reference

(CH3OOCC6H4)2SO2

334.35

102, 109

(HOC6H4)2SO2

250.27

6, 861

HO3SC6H3(OH)COOH

254.21

11, 411

150.09

3, 520

1.759820 4

168–170

150.09

3, 528

1.66620 4

140

534.37 230.31 136.24 136.24 154.25 256.4 345.67

25, 252 5, 695 5, 126 5, 128 6, 55

0.837520 4 0.85315 4 0.933820 4 0.982420 4 2.952925

212–213 383 174 183 36.4 219 11412mm 0.0 243.5

463.72

17, 485

274–276

misc alc, eth; 0.07 aq sl s bz; i aq, alc

C6H4(CHBr2)2

421.77

5, 367

114–116

v s chl

C6H4(CHBr2)2

421.77

5, 375

105–108

v s bz, chl

(C4H9O)4Si (C4H9)4NBr

320.5 322.38

(C4H9)4NCI

277.92

Formula

HOOCCH(OH)CH(OH)COOH xH2O C6H5C6H4C6H5

(H2C ¨ CHCH2O)4Si Br2CHCHBr2

1, 94

Density

Refractive index

Melting point

Flash point

Solubility in 100 parts solvent

195–196 1.366315

245–247

s alc, eth, acet; i aq v s aq, alc; s eth

120

139 aq; 33 alc; 0.4 eth 125 aq v s aq

0.89920 4

1.477520 1.475416 1.482020 1.433620 1.632325

1.41320

1153mm 103–104

43, 292

Boiling point

83–86

46 51 79 none

misc alc, eth v s alc, eth

t16 t17 t18 t19 t20 t21 t22 t23

Tetrabutylammonium fluoride trihydrate Tetrabutylammonium hydrogen sulfate Tetrabutylammonium iodide Tetrabutylammonium tetrafluoroborate Tetrabutyltin 1,1,3,3-Tetrachloroacetone 1,2,3,4-Tetrachlorobenzene 1,2,4,5-Tetrachlorobenzene

Sylvan, m252 Sylvic acid, a1 2,4,5-T, t242 TAPS, t427

(C4H9)4NF· 3H2O

315.52

(C4H9)4NHSO 4

339.54

(C4H9)4NI

369.38

4, 157

145–148

(C4H9)4NBF 4

329.28

43, 293

160–162

(C4H9)4Sn Cl2CHCOCHCl2

347.15 195.86

1, 656

C6H2Cl4

215.89

5, 204

C6H2Cl4

215.89

5, 205

43, 292

62–63 169–171

1.057 1.62415 4

1.474220 1.49718

97

46–47 1.85822

Taurine, a161 Terephthaldehyde, b13 Terephthaldicarboxaldehyde, b13 Terephthalic acid, b17

sl s aq; s alc, eth

14510mm 182745mm

107 none

v s acet, chl

254

112

v s eth; sl s alc

112

s bz, chl, eth

138–140 240–246

Terephthaloyl chloride, b15 TES, t424 Tetracene, b7

1.357

1.358

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t24 t25 t26 t27 t28 t29 t30 t31 t32 t33 t34 t35 t36 t37 t38 t39

Name Tetrachloro-obenzoquinone Tetrachloro-pbenzoquinone Tetrachloro-1,2difluoroethane 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene 2,3,5-Tetrachloronitrobenzene Tetrachlorophthalic anhydride 3,4,5,6-Tetrachlorophthalimide 1,1,2,3-Tetrachloro2-propene 2,3,5,6-Tetrachlorothioanisole 2,4,5,6-Tetrachlorom-xylene Tetracosane Tetracyanoethylene Tetradecane Tetradecanoic acid

Formula weight

Beilstein reference

C6Cl4( ¨ O)2

245.88

7, 602

127–129

C6Cl4( ¨ O)2

245.88

7, 602

290

subl

s eth; sl s chl; i aq

Cl2CFCFCl2

203.83

26.0

92.8

0.012 aq

ClCH2CCl3

167.85

Cl2CHCHCl2 Cl2C ¨ CCl2 HC6Cl4NO2

Formula

Density

Refractive index

Melting point

Boiling point

1.644725

1.413025

1, 86

1.598

1.481920

167.85

1, 86

1.586625 4

1.491025

165.83 260.89

1, 187 5, 247

1.623020 4 1.74425 4

1.505720

285.90

17, 484

254–258 371

284.91

21, 505

300

ClCH ¨ C(Cl)CHCl2

179.86

11, 83

HC6Cl4SCH3

262.0

C6Cl4(CH3)2

243.95

5, 373

CH3(CH2)22CH3 (NC)2C ¨ C(CN)2 CH3(CH2)12CH3 CH3(CH2)12COOH

338.66 128.09 198.40 228.38

1, 175

0.778651

1.428370

1, 171 2, 365

0.762720 4 0.852870 4

1.429020 1.427370

1.530

1.516320

Flash point

Solubility in 100 parts solvent

130

none

0.02 aq; misc alc

43.8

146.3

none

22.4 98–101

121.1 304

none

0.3 aq; misc alc, chl, eth, PE misc alc, chl, eth s alc, bz, chl

165

d hot aq; sl s eth

none

59–61 220–222 51.1 200 5.9 58.5

391 subl 120 253.5 250100mm

9.4 chl; s eth v s alc, eth v s bz, chl, eth; s alc

t40 t41 t42 t43 t44 t45 t46 t47 t48 t49 t50 t51 t52 t53

1-Tetradecanol Tetradecanoyl chloride 1-Tetradecene 7-Tetradecene 1-Tetradecylamine 4-Tetradecylaniline Tetradecyltrichlorosilane Tetraethoxysilane Tetraethylammonium bromide Tetraethylammonium chloride Tetraethylammonium hydroxide Tetraethylene glycol Tetraethylene glycol dimethacrylate Tetraethylene glycol monomethyl ether

Tetraethyl orthosilicate, t47

CH3(CH2)13OH CH3(CH2)12COCl

214.39 246.82

1, 428 2, 368

0.815150

1.435850

37.8 1

264 16815mm

CH3(CH2)11CH ¨ CH2 CH3(CH2)5CH ¨ CH(CH2)5CH3 CH3(CH2)13NH2 CH3(CH2)13C6H4NH2 CH3(CH2)13SiCl3

196.38 196.38

1, 226

0.77515 4 0.764

1.435120 1.435120

12.9

251.2 250

213.41 213.41 331.8

4, 201 123, 2780

40–42 46–49

16215mm

(CH3CH2O)4Si (CH3CH2)4NBr

208.33 210.16

4, 104

0.93420 4 1.39720 4

(CH3CH2)4NCl

165.71

4, 104

1.080121 4

(CH3CH2)4NOH

147.26

4, 103

(HOCH2CH2OCH2CH2)2O [H2C ¨ C(CH3)COOCH2 CH2OCH2CH2]2O CH3O(CH2CH2O)3CH2 CH2OH

194.23

1, 468

1.12520 20

330.37

1.08

208.26

0.987

115 99

v s alc; s eth

165.8

46

d aq; s alc v s aq, alc, acet, chl 141 aq; s alc; 8.2 chl misc aq

307.8

176

misc aq, alc, bz, eth

2201mm

62

16611mm

112

1563mm

1.382 1.38320

s eth; sl s alc d aq, alc; s eth

77 287 d 37.5

1.459020

1.445320

6

1.359

1.360

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t54 t55

t56 t57 t58 t59 t60 t61

t62 t63 t64 t65 t66 t67 t68 t69

Name

Formula

Tetraethylenepentamine N,N,N,N-Tetra ethylethylenediamine Tetraethylgermanium Tetraethyllead Tetraethyl pyrophosphate Tetraethyl pyrophosphite Tetraethylsilane Tetraethylthiuram disulfide

(H2NCH2CH2NHCH2CH2)2NH (C2H5)2NCH2CH2N(C2H5)2

Tetraethyltin Tetrafluoroethylene 2,2,3,3-Tetrafluoro1-propanol 1,2,3,6-Tetrahydrobenzaldehyde Tetrahydrofuran 2,5-Tetrahydrofurandimethanol Tetrahydro-2-furanmethanol Tetrahydro-2-furanmethylamine

Formula weight

Beilstein reference

189.31

Density

Refractive index

Melting point

0.99920 20

1.505520

40

172.32

4, 251

0.808

1.434320

(C2H5)4Ge (C2H5)4Pb [(C2H5O)2P(O)]2O

188.84 323.45 290.20

4, 631 4, 639

1.1989 1.65320 4 1.18520 4

1.519820 1.419620

[(C2H5O)2P]2O

258.19

1.057

1.434120

(C2H5)4Si [(C2H5)2NC( ¨ S)S ˆ ]2

144.34 296.54

42, 1007 4, 122

0.76220 4 1.30

1.424620

(C2H5)4Sn F2C ¨ CF2 HCF2CF2CH2OH

234.94 100.02 132.06

4, 632 13, 638

1.19920 4 1.150740 1.485320 1.319720 4

C6H9CHO

110.16

71, 48

0.940

1.474520

72.11

17, 10

0.889220 4

1.407220

1.154225 4

132.16

90 136 d 170

Boiling point

Flash point

340

185

189–192

58

165.5 152291mm

811mm

112

153–155

i aq 3.8 alc; 7.1 eth; s bz, acet, chl; 0.02 aq i aq; s eth i aq

181 75.6 109–110

49

163–164

57

108.5

66

17

1.476625

50

265

80

178

83

154744mm

45

102.13

172, 106

1.052420

1.452020

101.15

182, 415

0.980

1.456020

misc aq, alc, eth

s alc, eth; i aq s bz; misc eth d aq; misc alc, bz, chl

70 112 131.2 15

Solubility in 100 parts solvent

misc aq, alc eth, PE misc aq, alc, bz, chl; s eth misc aq, alc, bz, chl, eth, acet

t70

t71 t72 t73 t74

t75 t76 t77

2-(Tetrahydrofuryloxy)tetrahydropyran 1,2,3,4-Tetrahydroisoquinoline Tetrahydrolinalool 1,2,3,4-Tetrahydronaphthalene cis-1,2,3,6-Tetrahydrophthalic anhydride cis-1,2,3,6-Tetrahydrophthalimide Tetrahydropyran Tetrahydropyran2-methanol

Tetraglyme, b190 1,2,3,4-Tetrahydrobenzene, c330

186.25

133.19 (CH3)2CHCH2CH2CH2C(CH3)(OH)CH2CH3 C10H12

20, 275

158.28 132.21

5, 491

152.15

17, 462

1.030

1.460620

1.064

1.566820

0.92525

1.43320

0.970220 4

1.541420

30

232–233

98

35.8

207.6

77

misc alc, bz, chl, eth, acet, PE

20 93

misc aq, alc, eth misc aq, alc, bz, eth

101–102

151.17 86.14 116.16

97

134–138 0.881420 4 1.025420

Tetrahydrodicyclopentadiene, t253 Tetrahydro-2,5-dimethoxyfuran, d457

1.421120 1.458020

45 88 70 glass 187

Tetrahydrofurfurylamine, t69 Tetrahydrofurfuryl alcohol, t68

1.361

1.362

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t78 t79 t80 t81 t82 t83

t84 t85 t86 t87

t88 t89 t90

Name 1,2,3,6-Tetrahydropyridine 3,4,5,6-Tetrahydropyrimidinethiol 1,2,3,4-Tetrahydroquinoline Tetrahydrothiophene 1,4,9,10-Tetrahydroxyanthracene 2,2,4,4-Tetrahydroxybenzophenone Tetrahydroxyhexanedioic acid Tetrakis(2-ethylbutoxy)silane Tetrakis(2-ethylhexoxy)silane N,N,N,N-Tetrakis(p-hydroxypropyl)ethylene diamine Tetrakis(isopropoxy)silane Tetrakis(2-methoxyethoxy)silane Tetrakis(trimethylsiloxy)titanium

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

83.13

203, 1912

0.911

1.480020

48

Boiling point

16

249

100

s aq; misc alc, eth

12

misc alc, eth; i aq

24, 5

133.19

20, 262

1.061

1.5924

15–16

88.17 242.23

171, 5 8, 431

0.998720

1.504820

96.2 120.9 147–149

[(HO)2C6H3]2C ¨ O

246.22

8, 496

200–203

HOOC[CH(OH)]4COOH

210.14

3, 581

230 d

[CH3CH2CH(C2H5)CH2O]4Si [CH3(CH2)3CH(C2H5)CH2O]4Si {[CH3CH(OH)CH2]2NCH2 ˆ }2

432.8

0.89220 4

1.43020

1712mm

549.95

0.88020 4

1.438820

1941mm

1.013

1.481220

175– 1810.8mm

44, 1685

Solubility in 100 parts solvent

108

116.19

292.42

Flash point

210–212

0.003 aq; s alk

[(CH3)2CHO]4Si

264.4

0.87720 4

1.38520

645mm

(CH3OCH2CH2O)4Si

328.4

1.07920 4

1.42220

18210mm

[(CH3)3SiO]4Ti

404.7

0.90020 4

1.42720

11010mm

190

t91 t92 t93

t94

t95

t96 t97 t98 t99

1,1,3,3-Tetramethoxypropane Tetramethoxysilane Tetramethylammonium bromide Tetramethylammonium chloride Tetramethylammonium iodide N,N,3,5-Tetramethylaniline 1,2,3,4-Tetramethylbenzene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene

0.997

1.408120

1, 287 4, 51

1.05220 4 1.56

1.36820

4, 51

[(CH3O)2CH]2CH2

164.20

(CH3O)4Si (CH3)4NBr

152.2 154.06

(CH3)4NCl

109.60

(CH3)4NI

201.06

(CH3)2C6H3N(CH3)2

149.24

12, 1131

0.913

1.544320

C6H2(CH3)4

134.22

5, 430

0.90520 4

1.518720

C6H2(CH3)4

134.22

5, 430

0.890620 4

1.513420

C6H2(CH3)4

134.22

5, 431

0.83881 4

6,7,8,9-Tetrahydro-5H-tetrazoloazepine, p26 Tetrahydrothiophene 1,1-dioxide, t106 Tetrahydrothiophene oxide, t107

Tetrahydroxyadipic acid, t84 Tetralin, t73 -Tetralonehydantoin, b40

183

54

d  230

121–122 20 subl  360

55 aq

1.16920 4

d  230

subl  300

s aq, hot alc

1.829

d 230

sl s aq; v s abs alc

226–228

90

6.2

205.0

68

misc alc, eth

23.7

198.0

63

s alc; v s eth

79.2

196.8

73

v s alc, bz, eth

N,N,N,N-Tetramethyldiaminomethane, t113 N,N,N,N-Tetramethyl-1,3-diamino-2propanol, b173

1.363

1.364

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t100 t101

t102 t103 t104

t105 t106 t107 t108

t109 t110 t111

t112

Formula weight

Beilstein reference

Density

(CH3)3CC(CH3)3

114.23

1, 165

0.656120

(CH3)2N(CH2)4N(CH3)2

144.26

4, 265

0.78620

(CH3)3CCH2C(CH3)2NH2 [ ˆ SiH(CH3)O ˆ ]4

129.25

4, 198

[(CH3)2Si(Cl)CH2 ˆ ]2

215.3

[(CH3)2SiH]2O

134.3

Name 2,2,3,3-Tetramethylbutane N,N,N,N-Tetramethyl-1,4-butanediamine 1,1,3,3-Tetramethylbutylamine 1,3,5,7-Tetramethylcyclotetrasiloxane 1,1,4,4-Tetramethyl1,4-dichlorodisilylethylene Tetramethyldisiloxane Tetramethylene sulfone Tetramethylene sulfoxide N,N,N,N-Tetramethylethylene diamine Tetramethylgermanium 1,1,3,3-Tetramethylguanidine N,N,N,N-Tetramethyl-1,6-hexanediamine Tetramethyllead

Formula

240.5

120.71

171, 5

104.17 4, 250

Refractive index

Melting point 120.7

Boiling point

Flash point

Solubility in 100 parts solvent

106.5

1

1.428020

169

46

s aq, alc, eth

0.805

1.424020

137–143

32

s alc, eth, PE; i aq

0.991220 4

1.387020

69

134–135

37

198734mm

0.75720 4

1.37020

1.261430 4

1.482030

1.158

1.520020

0.770

1.417920

55

120–122

1.0060

1.387120

88

43.4

(CH3)2NCH2CH2N(CH3)2

116.21

(CH3)4Ge

132.73

[(CH3)2N]2C ¨ NH

115.18

[(CH3)2N(CH2)3 ˆ ]2

172.32

41, 423

0.806

(CH3)4Pb

267.33

4, 639

1.99520 4

68

71731mm 27.6

285

165

misc aq, acet, bz

 112 10

163 1.435920

209–210 27.5

110

73

misc alc, eth

t113

t114 t115 t116 t117

t118

t119 t120 t121

N,N,N,N-Tetramethylmethanediamine Tetramethyl orthocarbonate 2,6,10,14-Tetramethylpentadecane 2,3,5,6-Tetramethylphenol 2.2,6,6-Tetramethylpiperidino-N-oxy(free radical) N,N,N,N-Tetramethyl-1,3-propanediamine Tetramethylpyrazine Tetramethylsilane 1,2,2,3-Tetramethyl1,1,3,3-tetraphenyltrisiloxane

(CH3)2NCH2N(CH3)2

102.18

4, 54

0.74920

1.4005

C(OCH3)4

136.15

32, 4

1.023

1.384520

[(CH3)2CH(CH2)3CH(CH3)CH2]2CH2 (CH3)4C6HOH

268.53

0.782720 4

1.437920

150.22

6, 547

(CH3)4Si [(C6H5)2Si(CH3)O]2Si(CH3)2

2,2,5,5-Tetramethyl-3,4-dithiahexane, d114 Tetramethylene chlorobromide, b251 Tetramethylethylene glycol, d491

1

5

114

6

100

16711mm

36–38

130.24

4, 262

136.20 88.23 484.8

23, 99 4, 625

Tetramethylene oxide, t66 Tetramethylene sulfide, t81 Tetramethylolmethane, p20

s bz, chl, eth, PE

108–110 250

156.25

(CH3)2N(CH2)3N(CH3)2

85

1.423420

0.641120 4 1.0720 4

1.358520 1.55125

84–86 99.5

67

145–146

31

190 26.5 2350.5mm

27 221

v s alc, eth

2,2,4,4-Tetramethyl-3-thiapentane, d133 Tetramethylthiuram disulfide, b174

1.365

1.366

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t122 t123 t124 t124a t125 t126 t127 t128 t129 t130

t131 t132 t133 t134 t135

t136 t137

Formula weight

Beilstein reference

(CH3)2NC( ¨ S)N(CH3)2

132.23

41, 336

(CH3)4Sn (CH3)2NC( ¨ O)N(CH3)2

178.83 116.16

4, 631 4, 74

1.314925 0.968720 4

C(NO2)4

196.03 176.21

1, 80

1.622925 4 1.089

160.17

19, 436

Name 1,1,3,3-Tetramethyl2-thiourea Tetramethyltin 1,1,3,3-Tetramethylurea Tetranitromethane 1,4,7,10-Tetraoxacyclododecane 2,4,8,10-Tetraoxaspiro[5.5]undecane Tetraphenoxysilane Tetraphenylboron sodium 1,1,4,4-Tetraphenyl1,3-butadiene 1,1,3,3-Tetraphenyl1,3-dimethyldisiloxane Tetraphenylethylene Tetraphenylsilane Tetraphenyltin Tetrapropoxysilane Tetrapropylammonium bromide 1H-Tetrazole 2-Thenoyltrifluoroacetone

Formula

Density

1.14160 4

(C6H5O)4Si (C6H5)4BNa

400.5 342.23

(C6H5)2C ¨ CHCH ¨ C(C6H5)2 [(C6H5)2Si(CH3)]2O

358.49 410.7

(C6H5)2C ¨ C(C6H5)2 (C6H5)4Si (C6H5)4Sn (C3H7O)4Si (CH3CH2CH2)4NBr

332.45 336.5 427.11 264.4 266.27

5, 743

70.06 222.18

26, 346

Refractive index

Boiling point

75–77

245

1.5201 1.449325

54.8 1.2

78 176

1.435825 1.462120

13.5 16

126

52–55

831.5mm

48–49  300

2371mm

1.55460

5, 750

Flash point

65  112  112

Solubility in 100 parts solvent

misc aq, alc, chl, eth v s alc, eth, alk

v s aq, acet; s chl

207–209 1.07625 4

1.07820 4 1.4900 0.91620 4 41, 364

Melting point

1.586626

1.40120

50

2150.5mm

222–224 420 236–237 2283mm 226  420 945mm 270 d

156–158 subl 40–44 988mm

193

110 s aq

s aq, alc, acet

t138

Theobromine

180.17

26, 457

t139 t140 t141 t142 t143

Thiamine HCl Thiazole Thioacetamide Thioacetic acid Thiobenzoic acid

337.27 85.13 75.13 76.12 138.19

27, 15 2, 232 2, 230 9, 419

Tetrantoin, b40 2,5,8,13-Tetraoxadodecane, b189 3,6,9,12-Tetraoxatridecanol, t53 Tetraphene, b6 2-Thenoic acid, t157 2-Thiabutane, e182

CH3C( ¨ S)NH2 CH3O ˆ SH C6H5CO ˆ SH

357

subl 290

d 248 1.20017

1.537520

1.065 1.174

1.463020 1.602020

Thiacyclobutane, t345a 1-Thia-3-cyclopentene, 1,1-dioxide, d368 3-Thiaheptane, b451 2-Thiahexane, b463 3-Thiahexane, e210 Thianaphthene, b61

117–118 112–114  17 88–91 15–18 d

22 1  112

5-Thianonane, d132 2-Thiapentane, m395 3-Thiapentane, d337 Thioanisole, m364 2-Thiobarbituric acid, d388

0.05 aq; 0.045 alc; s alk; i bz, chl, eth 100 aq; 1 alc s alc, eth; sl s aq 16 aq; sl s alc, eth s aq; misc alc, eth misc eth; v s alc; i aq

1.367

1.368

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t144

t145 t146 t147 t148 t149 t150 t151 t152 t153 t154 t155 t156 t157 t158 t159 t160

Name 4,4-Thiobis(2-tertbutyl-6-methylphenol) 4,4-Thiobis(1,3dihydroxybenzene) Thiocarbanilide p-Thiocresol 2,2-Thiodiacetic acid 2,2-Thiodiethanol 4,4-Thiodiphenol 3,3-Thiodipropionic acid 2-Thiohydantoin N-Thionylaniline Thiophene 2-Thiopheneacetic acid 2-Thiophenecarbaldehyde 2-Thiophenecarboxylic acid 2-Thiophenemethylamine Thiophenol Thiophenoxyacetic acid

Formula

Formula weight

Beilstein reference

Density

Refractive index

358.54

Melting point

250.27

63, 6291

C6H5NHCSNHC6H5 HSC6H4CH3 (HOOCCH2)2S

228.32 124.21 150.15

12, 394 6, 416 3, 253

1.3224

(HOCH2CH2)2S

122.19

1, 470

1.182420 4

(HOC6H4)2S (HOOCCH2CH2)2S

218.27 178.21

6, 860

C6H5N ¨ SO C4H4S (C4H3S)CH2COOH

116.14 139.18 84.14 142.18

24, 260 12, 578 17, 29 18, 293

1.236 1.057325 4

1.627020 1.525725

(C4H3S)CHO

112.15

17, 285

1.200

1.590020

(C4H3S)COOH

128.15

18, 289

(C4H3S)CH2NH2

113.19

184, 7096

1.103

1.556920

C6H5SH

110.18

6, 294

1.076620

1.589720

C6H5SCH2COOH

168.21

6, 313

Flash point

31640mm

240

154 43–44 129

195

68

16

282

110

127

[(HO)2C6H3]2S

Boiling point

Solubility in 100 parts solvent

175–177

1.520320

150–155 134

128.5

14.9 64–66

misc aq, alc; sl s eth 3.4 aq; v s alc

231 d 38.2 63–67

v s alc, eth s alc, eth; i aq s aq, alc

sl s aq; i alc, eth 200 84.2 16022mm

1

misc alc, eth; i aq

198

77

s eth

260

s aq, chl; v s alc, eth

9928mm

73

169.1

50

v s alc; misc bz, eth

t161 t162 t163 t164 t165

Thiopropionic acid 3-Thiosemicarbazide Thiourea 1,4-Thioxane Thioxanthen-9-one

CH3CH2CO ˆ SH H2NC( ¨ S)NHNH2 H2NC( ¨ S)NH2

t166

Titanium(IV) isopropoxide Toluene

Ti[OCH(CH3)2]4

2,4-Toluenediamine 2,5-Toluenediamine 2,6-Toluenediamine 3,4-Toluenediamine Toluene-2,4-diisocyanate

CH3C6H3(NH2)2 CH3C6H3(NH2)2 CH3C6H3(NH2)2 CH3C6H3(NH2)2 CH3C6H3(NCO)2

t167 t168 t169 t170 t171 t172

Thiocarbanilide, d692 2,2-Thiodiethanethiol, b187 Thiodiethylene glycol, t149 Thiodiglycol, t149 Thiodiglycolic acid, t148 Thioethanolamine, a162 1-Thioglycerol, m20 Thioglycolic acid, m14

C6H5CH3

90.14 91.14 76.12 104.17 212.27

2, 264 3, 195 3, 180 19, 3 17, 357

1.014

284.26

12, 382

0.955

92.14

5, 280

0.866020 4

122.17 122.17 122.17 122.17 174.16

13, 124 13, 144 13, 148 13, 148 13, 138

Thiolactic acid, m21 Thiomalic acid, m23 4,4-Thioresorcinol, t145 Thiosalicyclic acid, m16 Thiosinamine, a101 2-Thixo-4-thiazolidinone, r3 Threonine, a187 Tiglic acid, m161

1.045 1.114

1.224420 4

1.464020

108–110

11

182–184 176–178 1.509520

s aq, alc 9 aq; s alc; sl s eth 147 273715mm

42

211 1.465420

18–20

21810mm

22

1.496920

95.0

110.6

7

283.5 273–274

1.568920

97–99 64 104–106 88–90 20–21

15618mm 251

v s bz, chl, hot HOAc

121

Tioxolone, h104 TMS, t120 TMSDEA, t371 TMSI, t373 Tolazoline, b102 p-Tolualdehyde, m126 Toluenethiols, p128, t147

misc alc, chl, eth, acet, HOAc s hot aq, alc, eth v s aq, alc, eth s aq, alc v s aq d aq, alc; misc bz, acet, eth

1.369

1.370

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t173 t174 t175 t176 t177 t178 t179 t180 t181 t182 t183 t184 t185 t186 t187 t188 t189 t190 t191 t192

Name p-Toluenesulfinic acid p-Toluenesulfonamide p-Toluenesulfonylhydrazide p-Toluenesulfonic acid p-Toluenesulfonyl chloride p-Toluenesulfonyl fluoride p-Toluenesulfonyl isocyanate o-Toluidine m-Toluidine p-Toluidine 1-(o-Toluidino)-1,3butanedione o-Tolunitrile m-Tolunitrile p-Tolunitrile o-Toluoyl chloride m-Toluoyl chloride p-Toluoyl chloride m-Tolyl isocyanate ( p-Tolylsulfonyl)methyl isocyanide p-Tolyltrichlorosilane

Formula weight

Beilstein reference

CH3C6H4SO2H

172.20

11, 9

85

v s alc, eth

CH3C6H4SO2NH2 CH3C6H4SO2NHNH2

171.22 186.23

11, 104 112, 66

137–140 110 d

0.2 aq; 3.6 alc

CH3C6H4SO3H

172.20

11, 97

CH3C6H4SO2Cl

190.65

11, 103

CH3C6H4SO2F

174.19

112, 54

CH3C6H4SO2NCO

197.21

CH3C6H4NH2 CH3C6H4NH2 CH3C6H4NH2 CH3C6H4NHCOCH2COCH3 CH3C6H4CN CH3C6H4CN CH3C6H4CN CH3C6H4COCl CH3C6H4COCl CH3C6H4COCl CH3C6H4NCO CH3C6H4SO2CH2NC

107.16 107.16 107.16 191.23

12, 772 12, 853 12, 880 12, 823

0.998420 0.98920 4 1.04620 4

1.572520 1.568120 1.553259

16.1 30.4 43.8 104–106

200.4 203.4 200.6 143

85 85 88

1.7 aq; s alc, eth misc alc, eth 7.4 aq; v s alc, eth

117.15 117.15 117.15 154.60 154.60 154.60 133.15 195.24

9, 466 9, 477 9, 489 9, 464 9, 477 9, 484 12, 864

0.995520 4 0.97615 0.978530 4 1.185 1.173 1.169 1.033

1.527920 1.525620

13 23 29.5

205.2 210 217.6 9012mm 865mm 225–257 7612mm

84 86

i aq; misc alc, eth 0.09 aq; v s alc, eth i aq; v s alc, eth

CH3C6H4SiCl3

225.6

Formula

Density

Refractive index

Melting point

Solubility in 100 parts solvent

67 aq; s alc, eth

69–71

13410mm

v s alc, bz, eth; i aq

41–42

11216mm 14410mm

2 114–115

1.320 4

Flash point

14020mm

1.435520

1.554920 1.548520 1.553520 1.530520

Boiling point

218–220

76 76 82 65

s alc, eth; i aq

t193 t194 t195 t196 t197

t198 t199 t200 t201 t202 t203 t204 t205

1,2,4-Triacetoxybenzene Triacetoxyethylsilane Triacetoxyvinylsilane 1,3,5-Triacetylbenzene Triallyl-s-triazine2,4,6(1H,3H,5H)trione 2,4,6-Triamino1,3,5-triazine 1H-1,2,4-Triazole Tribenzylamine Tribromoacetaldehyde Tribromoacetic acid 2,4,6-Tribromoaniline 2,2,2-Tribromoethanol 1,1,2-Tribromoethylene

Toluic acids, m130, m131, m132 -Tolunitrile, p80

C6H3(OOCCH3)3

252.22

6, 1089

98–100

C2H5Si(OOCCH3)3

234.3

1.142820 4

1.412320

(CH3COO)3SiCH ¨ CH2

232.3

1.16720 4

1.42320

C6H3(COCH3)3

204.23

7, 866

160–162 1.512920

249.27

(C6H5CH2)3N Br3CCHO Br3CCOOH Br3C6H2NH2 Br3CCH2OH BrCH ¨ CBr2

107– 1088mm 1131mm

126.12

26, 245

69.07 287.41 280.76 296.76 329.83 282.77 264.74

26, 13 12, 1038 1, 626 2, 220 12, 663 12, 338 1, 191

p-Tolylacetamide, m355 Triacetin, p201

0.99195 4 2.665

1.585020

2.35 1.70821

1.624725

17 1524mm

 250

1.573250

104

 112

subl

119–121 260 d 91–94 174 130–133 245 d 120–122 300 80–81 9310mm 162.5

sl s aq; i alc, eth

65 65

1,3,5-Triazine-2,4,6-triol, c299 Tributyl borate, t209

s aq, alc s hot alc, eth s aq, alc, chl, eth s aq, alc, eth s hot alc, chl, eth 2 aq; s alc, bz, eth

1.371

1.372

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

1.600515

8.1

149.6

94–96 16–17

244 219–221

Flash point

Solubility in 100 parts solvent

t206

Tribromomethane

CHBr3

252.77

1, 68

2.903115

t207 t208

Br3C6H2OH BrCH2CH(Br)CH2Br

330.82 280.78

6, 203 1, 112

2.55 2.411415

(C4H9O)3B (C4H9)3N [(CH3)3C]3C6H2OH

230.16 185.36 262.44

12, 398 4, 157

0.858020 0.778420 4 0.86427 4

1.409220 1.428320

70 70 131

t212

2,4,6-Tribromophenol 1,2,3-Tribromopropane Tributoxyborane Tributylamine 2,4,6-Tri-tertbutylphenol Tributyl phosphate

(C4H9O)3P(O)

266.32

12, 397

0.97225

1.422625

 80

t213 t214

Tributylphosphine Tributyl phosphite

(C4H9)3P (C4H9O)3P

202.32 250.32

42, 971 11, 187

0.812 0.92520 4

1.461920 1.432620

t215 t216 t217

Tributyltin chloride Trichloroacetic acid Trichloroacetonitrile Trichloroacetyl chloride Trichloroacetyl isocyanate 2,4,5-Trichloroaniline 2,4,6-Trichloroaniline 1,2,3-Trichlorobenzene 1,2,4-Trichlorobenzene

(C4H9)3SnCl Cl3CCOOH Cl3CCN

325.49 163.39 144.39

1.200 1.62961 4 1.440325 4

1.490520

2, 206 2, 212

Cl3CCOCl

181.83

2, 210

1.629

Cl3CC( ¨ O)NCO

188.40

Cl3C6H2NH2

196.46

12, 627

93–95

270

s alc

Cl3C6H2NH2

196.46

12, 627

73–75

262

s alc, eth

C6H3Cl3

181.45

5, 203

1.6925 25

52.6

221

113

v s bz, CS2

C6H3Cl3

181.45

5, 204

1.44625

17

214

110

misc bz, eth, PE

t209 t210 t211

t218 t219 t220 t221 t222 t223

none

0.3 aq; misc eth, MeOH s alc, chl, eth; i aq s alc, eth

233.5 216–217 278

93 63

hyd aq v s alc, eth; s acet

289 d

146

0.04 aq; misc org solv

15050 mm 1257mm

40 121  112

1.440920

17325mm 196–197 85.7

none

1.468920

114–116

none

1.480920

8520mm

65

57–58

1.570720

misc alc, bz, eth, PE 120 aq; v s alc, eth

t224 t225

t226 t227 t228 t229 t230 t231 t232 t233 t234

1,3,5-Trichlorobenzene 2,2,2-Trichloro-1,1dimethylethyl chloroformate 1,1,1-Trichloroethane 1,1,2-Trichloroethane 2,2,2-Trichloroethanol 2,2,2-Trichloroethyl chloroformate 1,1,2-Trichloroethylene Trichloroethylsilane Trichlorofluoromethane ,,2-Trichloro6-fluorotoluene Trichloroisocyanuric acid

1.566219

C6H3Cl3

181.45

63.4

208.5

107

ClCOOC(CH3)2CCl3

239.92

30–32

83– 8414mm

none

CH3CCl3

133.41

1, 85

1.337620 4

1.437920

30.4

74.0

none

0.13 aq; s bz, eth

ClCH2CHCl2

133.41

1, 85

1.441620 4

1.471120

36.6

113.5

none

1.55720 20

1.488520

17.8

151

0.4 aq; misc alc, eth 8 aq; misc alc, eth

Cl3CCH2OH

149.40

1, 338

ClCOOCH2CCl3

211.86

1.539

1.470320

ClCH ¨ CCl2

131.39

1.464920 4

1.477520

C2H5SiCl3 Cl3CF

163.5 137.4

1.237320 4 1.48521

1.425620 1.38420

ClC6H3(F)CHCl2

213.47

53, 701

1.446

1.550620

232.41

25, 256

Tributyrin, g19 ,,-Trichloroethoxycarbonyl chloride, t229

5, 204

1, 187

Trichloromethane, c126 Trichlorophenylsilane, p155

171–172

none

84.8

86.7

none

106 111

100.5 23.8

27

228–230

 112

v s bz, eth, PE

0.1 aq; misc alc, chl, eth 0.14 aq; s alc, eth

249–251

3,3,3-Trichloropropylene oxide, e13

1.373

1.374

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t235 t236 t237 t238 t238a t239 t240

Formula weight

Beilstein reference

Density

Refractive index

Cl3CSCl

185.89

3, 135

1.70020 4

1.543620

Cl3CSO2Cl

217.88

32, 16

139

(CH3)2C(OH)CCl3

177.46

1, 382

99

167

CH3SiCl3

149.48

90

66

Cl3C6H2NO2

226.45

5, 246

1.79020

49–55

288

v s bz, eth

Cl3CNO2

164.38

1, 76

1.655820 4

64

112

misc alc, bz; s eth

Cl3C6H2OH

197.45

62, 180

67

253

69

246

615 acet; 163 bz; 525 eth; s alc; i aq 525 acet; 113 bz; 354 eth; v s alc; i aq s alc; v sl s aq

Name Trichloromethanesulfenyl chloride Trichloromethane sulfonyl chloride 1,1,1-Trichloro-2methyl-2-propanol Trichloromethylsilane 1,2,4-Trichloro-5nitrobenzene Trichloronitromethane 2,4,5-Trichlorophenol

Formula

1.27520 4

t241

2,4,6-Trichlorophenol

Cl3C6H2OH

197.45

6, 190

t242

(2,4,5-Trichlorophenoxy)acetic acid 2-(2,4,5-Trichlorophenoxypropionic acid 1,2,3-Trichloropropane 1,1,1-Trichloro-2propanol

Cl3C6H2OCH2COOH

255.49

63, 702

Cl3C6H2OCH(CH3)COOH

269.51

ClCH2CH(Cl)CH2Cl

147.43

1, 106

CH3CH(OH)CCl3

163.43

1, 365

t243

t244 t245

1.410820

1.461120

1.490175 4

Melting point

Boiling point 146–148

Flash point none

s alc, eth s alc, bz, chl, eth 5

none

153

181.6

1.388020

1.483420

Solubility in 100 parts solvent

0.14 aq; 16 acet; 0.16 bz; 7.1 eth

14.7

156.9

82

misc alc, eth; i aq

50

162

82

2.9 aq; v s alc, eth

t246 t247 t248 t249 t250 t251 t252 t253 t254 t255

2,4,6-Trichloropyrimidine Trichlorosilane ,,Trichlorotoluene ,2,6-Trichlorotoluene 2,4,6-Trichloro1,3,5-triazine 1,1,2-Trichlorotrifluoroethane Trichlorovinylsilane Tricyclo[5.2.1.02,6]decane Tricyclo[5.2.1.02,6]decan-8-one 1,3,5-Tricyclohexylhexahydro-striazine

Tricine, t428

183.43

23, 90

HSiCl3 C6H5CCl3

135.45 195.48

5, 300

Cl2C6H3CH2Cl

195.48 184.41

26, 35

Cl2CFCClF2

187.38

13, 157

H2C ¨ CHSiCl3

161.49 136.24

5, 164

150.22

72, 133

1.341720 4 1.375620 4

1.570020

23–25

210–215

 112

1.40020 1.557020

1.28 5.0

31–32 220.8

20 97

36–39

11914mm

v s alc, eth

148

190720mm

i aq; s alc

1.563525

1.355725

36.4

47.6

none

1.24320 4

1.430020

95

90–93

9

77–79

193

40

1.063

333.57

Tricyclo[3.3.1.13,7]decane, a67

1.502520

d aq; s bz, chl s alc, bz, eth

0.017 aq

13230mm 74–75

976mm

Tricyclo[5.2.1.02,6]decane-4,8-dimethanol, b185

1.375

1.376

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

0.756320 4

1.425620

0.765320 1.124220 4

1.433420 1.483525

5.4 41–42 23.1 21.6

Boiling point

Tridecane Tridecanoic acid 1-Tridecene Triethanolamine

CH3(CH2)11CH3 CH3(CH2)11COOH CH3(CH2)10CH ¨ CH2 (HOCH2CH2)3N

184.37 214.35 182.35 149.19

1, 171 2, 364 1, 225 4, 285

t260 t261

(CH3CH2O)3B (C2H5O)3SiC2H5

145.99 192.3

1, 335

0.86420 20 0.896320 4

1.374020 1.395520

117–118 158–159

11

CH3Si(OC2H5)3

178.30

4, 629

0.89520 4

1.384520

141–143

23

s alc

(C2H5O)3SiH (C2H5O)3SiCH ¨ CH2

164.28 190.32

1, 334

0.87520 4 0.90320 4

1.3762 1.397820

131.5 160–161

26 34

t263 t264

Triethoxyborane Triethoxyethylsilane Triethoxymethylsilane Triethoxysilane Triethoxyvinylsilane Triethylaluminum Triethylamine

v s alc, eth v s alc, eth; i aq s alc; v s eth misc aq, alc, acet; 4.5 bz; 1.6 eth; s chl d aq

(C2H5)3Al (C2H5)3N

114.17 101.19

4, 643 4, 99

0.83225 0.732625 4

1.398025

58 114.7

194 89.6

6

t265 t266 t267

Triethylantimony Triethylarsine Triethylbismuthine

(C2H5)3Sb (C2H5)3As (C2H5)3Bi

208.94 162.11 296.17

4, 618 4, 602 4, 622

1.32416 1.15020 4 1.82

1.42

29

t268 t269

Triethylborane Triethylenediamine

(C2H5)3B

98.00 112.18

4, 641

0.696123

t270 t271

Triethylene glycol Triethylene glycol dibenzoate Triethylenetetramine

(HOCH2CH2OCH2 ˆ )2 (C6H5COOCH2CH2OCH2 ˆ )2 (H2NCH2CH2NHCH2 ˆ )2

150.17 358.39

1, 468

1.127415 4 1.271530

1.457815 1.525250

4.3 47

285

165

146.24

4, 255

0.982

1.497120

12

266–267

143

t261b t262

t272

79

Solubility in 100 parts solvent

t256 t257 t258 t259

t261a

235.4 236100mm 232.8 335.4

Flash point

79 185

159.5 140736mm 10779mm explodes when heated in air 92.9 95 158 174

d aq, air 5.5 aq; misc alc, eth; s acet, EtAc i aq; misc alc, eth i aq; v s alc, eth i aq; d air 45 aq; 13 acet; 77 alc; 51 bz misc aq, alc, bz

t273

144.26

42, 691

0.804

1.431120

156.91 171.29

26, 2

1.057630 0.894

1.459520

(C2H5)3In CH3C(OC2H5)3

202.01 162.23

2, 129

1.26020 0.884725 4

HC(OC2H5)3

148.20

2, 20

CH3CH2C(OC2H5)3

176.26

(C2H5O)3P(O) (C2H5)3P

Triethyl phosphite

Triethyl phosphonoacetate

t280 t281

N,N,N-Triethylethylenediamine Triethylgallium 1,3,5-Triethylhexahydro-s-triazine Triethylindium Triethyl orthoacetate Triethyl orthoformate Triethyl orthopropionate Triethyl phosphate Triethylphosphine

t282

t283

t274 t275 t276 t277 t278 t279

(C2H5)2NCH2CH2NHC2H5 (C2H5)3Ga

5513mm

32

82.3

142.6 207–208

1.53820 1.395025

32

144 142

55

misc alc, chl, eth

0.89120 4

1.391920

76

146

30

d aq; s alc, eth

2, 240

0.876

1.399520

155–160

60

v s alc, eth

182.16 118.16

1, 332 4, 582

1.072519 0.80015 4

1.404520

215–216 129

(C2H5O)3P

166.2

1, 330

0.96920 4

1.413120

6524mm

(CH3CH2O)2P(O)CH2COOC2H5

224.19

41, 573

1.130

1.431020

1459mm

s aq(d), alc, eth pyro- i aq; misc alc, eth phoric 55 i aq(hyd); misc alc, acet, bz, eth, PE  112

Tridecylbenzene, p156 3-Triethoxysilylpropylamine, a279 Triethyl borate, t260

Triethylenediamine, d45 Triethylene glycol, e127 Triethylene glycol dimethyl ether, b189

88

O,O,O-Triethyl phosphorothioate, t285

1.377

1.378

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t284 t285 t286 t287 t288 t289 t290 t291 t292 t293 t294

t295 t296 t297 t298

Formula weight

Beilstein reference

Density

Refractive index

(C2H5)3SiH (C2H5O)3P(S)

116.28 198.22

4, 625 1, 333

0.73120 4 1.082

1.41220 1.448020

CF3CONH2

113.04

22, 186

CF3COOH [CF3C(O)]2O

114.02 210.03

22, 186 22, 186

C6H5COCF3

174.12

CF3C6H4OH

162.11

CH3CF3 CF3CH2OH

Name Triethylsilane Triethyl thiophosphate 2,2,2-Trifluoroacetamide Trifluoroacetic acid Trifluoroacetic anhydride ,,-Trifluoroacetophenone ,,-Trifluorom-cresol 1,1,1-Trifluoroethane 2,2,2-Trifluoroethanol 2,2,2-Trifluoroethyl acrylate 2,2,2-Trifluoroethyl trifluoroacetate Trifluoromethane Trifluoromethanesulfonic acid Trifluoromethanesulfonic anhydride 3-(Trifluoromethyl)benzonitrile

Formula

1.489020 1.487

1.285020  1.30

1.240

1.459520

1.333

1.458820

84.04 100.04

1.384220 4

1.290722

CF3CH2OOCCH ¨ CH2

154.0

2.14225 4

1.398125

CF3CH2OOCCF3

196.0

1.472518 4

1.281218

61, 187

70.01

1, 59

1.52100

CF3SO3H

150.07

33, 34

1.69525

1.325025

(CF3SO2)2O

282.13

34, 35

1.677

1.321220

CF3C6H4CN

171.12

9, 478

1.281320

1.450520

HCF3

Melting point

Boiling point 107–108 10016mm

75

162.5

15.3 65

71.8 39

Flash point

Solubility in 100 parts solvent i aq; misc alc, eth

107

misc aq

165–166

41

1.8

178–179

73

111.3 43.5

47.3 74.1

29

46125mm 65.5

55

155.2

82.2

34

162

none

84 14.5

189

75 mL aq; 500 mL alc v s aq; misc eth d aq, alc

72

t299 t300 t301 t302 t303 t304 t305 t306

3-(Trifluoromethyl)benzyl chloride ,,-Trifluorotoluene Trihexylamine Trihexylchlorosilane Trihexylsilane 1,2,3-Trihydroxybenzene 1,3,5-Trihydroxybenzene 3,4,5-Trihydroxybenzoic acid

1.254

1.4605

1.188620

1.414520

0.87120 4

1.45620

194.59

C6H5CF3

146.11

5, 290

[CH3(CH2)5]3N [CH3(CH2)5]3SiCl

269.52 319.1

4, 188

[CH3(CH2)5]3SiH C6H3(OH)3

284.60 126.11

6, 1071

C6H3(OH)3

126.11

6, 1092

218–220 subl d

(HO)3C6H2COOH

170.12

10, 470

d 235

[(CH3)2CHCH2]3Al

198.33

0.78125

t308

Triisodecyl phosphite Triisopropanolamine Triisopropoxyborane Triisopropoxyvinylsilane 1,3,5-Triisopropylbenzene Triisopropyl phosphite

[(CH3)2CH(CH2)7O]3P

502.80

0.88625 15

1.45425

[CH3CH(OH)CH2]3N [(CH3)2CHO]3B [(CH3)2CHO]3SiCH ¨ CH3 C6H3[CH(CH3)2]3

191.27 188.08 232.4

1, 363

0.999650 20 0.815 25 0.8634

204.36

5, 458

[(CH3)2CHO]3P

208.24

1, 363

t313

1.379

2,2,2-Trifluoroethyl mesylate, m438 2-(Trifluoromethyl)aniline, a129 3-(Trifluoromethyl)aniline, a130 m-Trifluoromethylphenol, t290

102

12

263–265 1555mm

 112

59 aq; 77 alc; 62 eth 1 aq; 10 alc; s eth 1.1 aq; 17 alc; 1 eth; 20 acet; i bz, chl, PE

6

8610mm

0

1800.1mm

46 1.376420 1.39625

305.4 139–141 179–181

152 17

0.845

1.488420

232–236

86

0.91420 4

1.410120

6411mm

73

4,4,4-Trifluoro-1-(2-thienyl)-1,3-butanedione, t137 ,,-Trifluorotoludines, a129, a130, a131 ,,-Trifluorotolunitrile, t298

v s alc, eth; i aq

1605mm 131–133

Triisobutylaluminum

t312

29

1.44820 1.45

t307

t309 t310 t311

7012mm

CF3C6H4CH2Cl

pyrophoric 235 v s aq

i aq (sl hyd)

Triglyme, b189 Tri-(2-hydroxyethyl)amine, t259 1,2,6-Trihydroxyhexane, h65 Triiodomethane, i36

1.380

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t314 t315 t316 t317 t318 t319 t320 t321 t321a t322 t323

t324

t325 t326

Name 3,4,5-Trimethoxybenzaldehyde 1,2,3-Trimethoxybenzene 3,4,5-Trimethoxybenzoic acid 3,4,5-Trimethoxybenzoyl chloride 3,4,5-Trimethoxybenzyl alcohol Trimethoxyborane Trimethoxyboroxine 1,3,3-Trimethoxybutane Trimethoxy(methyl)silane 1,3,3-Trimethoxypropane (Trimethoxysilyl)propyldiethylenetriamine N-[3-Trimethoxysilyl)propyl]ethylenediamine N-(Trimethoxysilylpropyl)imidazole 3-(Trimethoxysilyl)propyl methacrylate

Formula weight

Beilstein reference

(CH3O)3C6H2CHO

196.20

8, 391

C6H3(OCH3)3

168.19

6, 1081

(CH3O)3C6H2COOH

212.20

10, 481

168–171 22710mm

(CH3O)3C6H2COCl

230.65

10, 487

79–81

(CH3O)3C6H2CH2OH

198.22

6, 1159

1.233

1.545920

(CH3O)3B

103.91

1, 287

0.92023 4

1.356820

[ ˆ OB(OCH3) ˆ ]3 (CH3O)2C(CH3)CH2CH2OCH3 CH3Si(OCH3)3

173.53 148.20

13, 3214

1.195 0.940

1.399620 1.409620

0.954820 4

CH3OCH2CH2CH(OCH3)2 (CH3O)3Si(CH2)3NHCH2CH2NHCH2CH2NH2

134.18

(CH3O)3Si(CH2)3NHCH2CH2NH2

Formula

(CH3O)3SiCH2CH2CH2OOCC(CH3) ¨ CH2

Density

Refractive index

1.112

Melting point

Boiling point

73–75

16510mm

43–45

241

Flash point

v s alc, eth; s chl

18518mm 22825mm

 112

34

67–68

1

10

130 6320mm

10 45

1.369620

102–103

21

0.942

1.400420

45– 4617mm

265.4

1.0320 4

1.46320

222.4

1.010

1.445020

230.3

1.0020 4

1.4525

249.3

1.04520 4

1.42925

136.23 1, 820

Solubility in 100 parts solvent

14615mm

 112

190

92

hyd aq; misc alc, eth

t327

Trimethylaluminum

(CH3)3Al

72.09

4, 643

0.75220

t328

Trimethylamine

(CH3)3N

59.11

4, 43

0.636

t329

Trimethylamine-Noxide 2,4,6-Trimethylaniline 1,3,3-Trimethyl-6azabicyclo[3.2.1]octane 3,3,5-Trimethyl-1azacycloheptane 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene

(CH3)3N(O)

75.11

t330 t331

t332 t333 t334 t335

Trimellitic acid, b29 Trimesic acid, b30 Trimesoyl chloride, b32 Trimethylacetaldehyde, d596

1.43212

15.4

208mm

117.1

2.9

pyro- s alk; v sl s alc phoric 6 41 aq; misc alc; s bz, chl, eth s aq, MeOH

257 0.963

1.551020

233

96

153.27

0.902

1.471620

194

75

141.26

0.852

1.456320

180

67

C6H3(CH3)3

120.20

5, 399

0.89420 4

1.513920

25.4

176.1

48

i aq; s alc, eth

C6H3(CH3)3

120.20

5, 400

0.875620 4

1.504820

43.9

169.4

48

s alc, bz, eth

C6H3(CH3)3

120.20

5, 406

0.863720 4

1.499420

44.7

164.7

44

misc alc, bz, eth

(CH3)3C6H2NH2

135.21

12, 1160

Trimethylacetamide, d597 Trimethylacetic acid, d598 Trimethylacetic anhydride, d599 Trimethylacetyl chloride, d600

endo-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-o1, b216

1.381

1.382

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t336

t337 t338 t339 t340

t341 t342

t343 t344 t345 t345a t346 t347 t348

Name Trimethyl 1,2,4benzenetricarboxylate 2,2,3-Trimethylbutane 2,3,3-Trimethyl2-butanol 1,1,3-Trimethylcyclohexane 3,5,5-Trimethylcyclohex-2-ene1-one 2,2,6-Trimethyl1,3-dioxen-4-one 4,4-Trimethylenebis-(1-methylpiperidine) 4,4-Trimethylenedipiperidine 4,4-Trimethylenedipyridine Trimethylene oxide Trimethylene sulfide 2,2,5-Trimethylhexane 3,5,5-Trimethyl1-hexanol Trimethylhydroquinone

Formula weight

Beilstein reference

Density

Refractive index

Melting point

C6H3(COOCH3)3

252.22

91, 429

1.261

1.521420

38–40

19412mm

(CH3)2CHC(CH3)3

100.20

12, 121

0.690120 4

1.389420

24.9

80.9

s alc, eth

(CH3)3CC(CH3)2OH

116.20

12, 447

0.838025 4

1.423322

15–17

130.5

misc alc, eth

C6H9(CH3)3

126.24

Formula

1.429620

(CH3)2CHCH2CH2C(CH3)3 (CH3)3CCH2CH(CH3)CH2CH2OH (CH3)3C6H(OH)2

8.1

215.2

96

65– 672mm 21550mm

110

7, 65

142.15

193, 1604

1.088

1.462220

12–13

0.896

1.482020

13

210.37

65–68

198.27

57–60 17, 6 171, 3 13, 516

144.25 152.19

6, 931

Solubility in 100 parts solvent

 112

1.47820

138.2

58.08 74.15 128.26

Flash point

136.6

0.92520 20

238.42

Boiling point

0.893025 4 1.02520 0.707220

1.389525 1.510220 1.399720

73.3 105.8

50 95.0 124.1

0.823620 4

1.430025

 70

194

172–174

1 1

1.2 aq

misc aq v s org solv s alc, eth s aq; v s alc, bz, eth

t348a

2,6,8-Trimethyl4-nonanol

t349

2,6,8-Trimethyl-4nonanone -()-1,3,3-Trimethyl-2norbornanol

t350

(CH3)2CHCH2CH(CH3)CH2CH(OH)CH2CH(CH3)2 (CH3)2CHCH2CH(CH3)CH2C(O)CH2CH(CH3)2

Trimethyl borate, t319 Trimethylchlorosilane, c255 ,,4-Trimethyl-3-cyclohexene-1-methanol, t7 3,5,5-Trimethylcyclohex-2-en-1-one, i82 1,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acid, c5

186.33

0.8193

184.31

0.81820 20

75

218.4

0.964120 4

48

201

154.25

6, 70

Trimethylene chlorobromide, b257 Trimethylene chlorohydrin, c214 Trimethylenediamine, p193 Trimethylene dibromide, d93

225

93

73

s alc, eth

Trimethylene glycol, p195 Trimethylethylene, m159 Trimethylgermanium bromide, b363 3,3,5-Trimethylhexahydroazepine, t332

1.383

1.384

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t351

t352 t353 t354 t355 t356 t357 t358 t359 t360 t361 t362 t363 t364

Name ()-1,3,3-Trimethyl-2-norbornanone Trimethyl orthoacetate Trimethyl orthoformate 2,4,4-Trimethyl1-oxazoline 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,4-Trimethylpentane 2,2,4-Trimethyl1,3-pentanediol 2,4,4-Trimethyl1-pentene 2,3,5-Trimethylphenol 2,3,6-Trimethylphenol 2,4,6-Trimethylphenol Trimethyl phosphate Trimethyl phosphite

Formula weight

Beilstein reference

Density

Refractive index

Melting point

152.24

7, 96

0.94818

1.463518

5–6

CH3C(OCH3)3

120.15

12, 128

0.942825 4

1.385925

105

HC(OCH3)3

106.12

2, 19

0.967620 4

1.379020

100.6

15

113.16

0.887

1.421320

112–113

12

1.403020

112.3

109.8

Formula

Boiling point 192–193

Flash point 52

Solubility in 100 parts solvent v s alc, eth

v s alc, eth

(CH3)3CCH(CH3)CH2CH3 (CH3)2CHCH2C(CH3)3

114.23

11, 62

0.716020 4

114.23

12, 127

0.691920 4

1.391520

107.4

99.2

(CH3)2CH[CH(CH3)]2CH3

114.24

13, 500

0.719020 4

1.404220

109.2

113.5

(CH3)2CHCH(OH)C(CH3)2CH2OH (CH3)3CCH2C(CH3) ¨ CH2 (CH3)3C6H2OH

146.22

13, 2225

0.92855 15

1.451315

46

229

113

112.22

13, 849

0.715020 4

1.411220

93

101.4

1

136.19

6, 518

92–95

230–231

(CH3)3C6H2OH

136.19

(CH3)3C6H2OH

136.19

6, 158

(CH3O)3P(O) (CH3O)3P

140.08 124.08

1, 286 1, 285

s eth; sl s alc 7

s bz, chl, eth s alc, org solv 1.8 aq; 75 alc; 22 bz; 25 acet

62–64

1.197 1.04620 4

1.395820 1.408020

68–71

220

46  78

197 111–112

none 40

100 aq; s alc d aq; misc alc, acet, bz, PE

t365 t366 t367 t368 t369 t370 t371 t372 t373 t374

Trimethyl phosphonoacetate 1,2,4-Trimethylpiperazine 2,4,6-Trimethylpyridine N-(Trimethylsilyl)acetamide N-(Trimethylsilyl)aniline Trimethylsilyl bromoacetate N-(Trimethylsilyl)diethylamine 2-(Trimethylsilyl)ethanol N-(Trimethylsilyl)imidazole 3-(Trimethylsilyloxy)allene

Trimethylolpropane, e156 Trimethylsilyl cyanide, c298

(CH3O)2P(O)CH2COCH3

1.125

1.437020

128.22

0.85125 25

1.448025

 50

151746mm

0.916622 4

1.497920

43

170.5

57

52–54

185–186

57

s aq, alc, acet, bz

(C5H2N)(CH3)3

121.18

CH3CONHSi(CH3)3

131.25

(CH3)3SiNHC6H5

165.3

0.94020 4

1.52220

207–208

BrCH2COOSi(CH3)3

211.14

1.284

1.442120

28

(CH3)3SiN(C2H5)2

145.33

57– 589mm 127738mm

(CH3)3SiCH2CH2OH

118.25

0.825

1.424620

50

140.26

0.956

1.475120

71– 7335mm 9914mm

130.3

0.783030 4

1.407525

100–102

(CH3)3SiOCH2CH ¨ CH2

20, 250

1180.85mm

 112

182.11

Trimethylsilyldiethylamine, d343 Trimethylsilyl iodide, i55

80

Trimethylsilylnitrile, c298

3.5 aq; misc eth; s alc, bz, chl

1.385

1.386

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t375 t376 t377 t378 t379 t380 t381 t382 t383 t384 t385 t386 t387 t388 t389 t390

Name Trimethylsilylphenoxide Trimethylsilyl trifluoroacetate Trimethylsulfonium iodide Trimethylsulfoxonium iodide Trimethylvinyloxysilane Trimethylvinylsilane 2,4,6-Trinitroaniline 1,2,4-Trinitrobenzene 1,3,5-Trinitrobenzene 2,4,7-Trinitro-9fluorenone Trinitromethane 2,4,6-Trinitrotoluene Trioctylamine s-Trioxane Tripentaerythritol 2,4,6-Triphenoxys-triazine

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point 55

Boiling point

Flash point

Solubility in 100 parts solvent

(CH3)3SiOC6H5

166.3

0.925620 4

1.478220

(CH3)3SiOOCCF3

186.2

1.07720 4

1.388020

[(CH3)3S]I

204.07

215–220 subl

[(CH3)3S(O)]I

220.07

175 d

(CH3)3SiOCH ¨ CH2

116.2

0.77220 4

1.38920

74–75

(CH3)3SiCH ¨ CH2

100.2

0.69020 4

1.392020

55

(O2N)3C6H2NH2

228.12

12, 763

1.76214

188–190 explodes

s hot acet; sl s alc

C6H3(NO2)3

213.11

5, 271

1.7316

61–62

explodes

C6H3(NO2)3

213.11

5, 271

1.68820 4

122.5

explodes

315.20

72, 410

5.5 alc; 7.1 eth; i aq 0.035 aq; 1.9 alc; 1.5 eth; 6.2 bz v s bz, acet; sl s aq

HC(NO2)3 (O2N)3C6H2CH3

151.04 227.13

1, 79 5, 347

1.59724 4 1.65420 4

[CH3(CH2)7]3N

353.68 90.08

4, 196 19, 381

0.809 1.17065

372.41 357.37

8123mm 89–90

1

175–176 15 80.1

4722mm explodes

64

365–367 115

1.448520

245 d 232–234

s aq, alk 1.5 alc; 4 eth; s bz, acet; 0.01 aq  112 45

17.2 aq; v s alc, bz, eth, EtAc

t391

t396 t397

Triphenoxyvinylsilane Triphenylamine Triphenylantimony Triphenylarsine 1,3,5-Triphenylbenzene Triphenylene Triphenylmethane

t398 t399

Triphenylmethanol Triphenyl phosphate

t392 t393 t394 t395

2,4,6-Trinitrophenol, p173 Triolein, g22

1.13025 4

(C6H5O)3SiCH ¨ CH2

334.5

(C6H5)3N (C6H5)3Sb (C6H5)3As (C6H5)3C6H3

245.33 353.07 306.24 306.41

12, 181 16, 891 16, 828 5, 737

0.77400 1.434325 1.222548 1.205

(C6H5)3CH

228.29 244.34

5, 720 5, 698

(C6H5)3COH (C6H5O)3P(O)

260.34 326.29

6, 713 6, 179

Trioxymethylene, t388 Tripalmitin, g23

1.56225

2107mm 125–127 52–54 60–62 172–174

347–348 377 23314mm 460

1.302 1.013499 4

199 93.4

425 360

1.19904

164.2 49–51

360 24410mm

1.613948

223

Triphenylmethyl bromide, b366

s acet, eth; sl s alc v s bz, eth; sl s alc v s bz, eth; s alc v s bz; s abs alc, eth s alc; v s bz, eth v s hot alc, eth; 49 chl; 7 bz; s PE; i aq v s alc, bz, eth; i aq misc alc; s bz, acet, chl, eth; i aq

1.387

1.388

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

16, 759

1.07581 4

Refractive index

t400

Triphenylphosphine

(C6H5)3P

262.29

t401

Triphenylphosphine selenide Triphenylphosphine sulfide Triphenyl phosphite Triphenylsilane Tripiperidinophosphine oxide Tripropoxyborane Tripropylamine Tripropylene glycol Tripropylene glycol butyl ether Tripropylene glycol ethyl ether Tripropylene glycol isopropyl ether Tripropylene glycolmethyl ether Tripropyl orthoformate Tris(butoxyethyl) phosphate Tris(2-chloroethoxy)silane

(C6H5)3P(Se)

341.25

(C6H5)3P(S)

294.36

16, 784

(C6H5O)3P (C6H5)3SiH

310.29 260.41 299.40

6, 177 162, 605 20, 88

1.18425 15

1.590320

(CH3CH2CH2O)3B (CH3CH2CH2)3N H(OCH2CH2CH2)3OH HO(CH2CH2CH2O)3(CH2)3CH3 HO(CH2CH2CH2O)3CH2CH3 HO(CH2CH2CH2O)3CH(CH3)2 HO(CH2CH2CH2O)3CH3

188.08 143.27 192.3 248.4

12, 369 4, 139

0.857620 4 0.753 1.018 0.93425 25

1.394820 1.416020 1.44225 1.43025

220.3

0.094825 25

234.8

t402 t403 t404 t405 t406 t407 t408 t409 t410 t411 t412 t413 t414 t415

Melting point 80.5

Boiling point

Flash point

Solubility in 100 parts solvent

377

181

v s eth; s bz, chl, HOAc; sl s alc; i aq

360 1522mm 27350mm

218

s alc, bz, chl, eth

187–189 162–164 22–24 42–44 40–42

175 155–158 267.2 276

36 141 135

1.42725

486

132

0.094225 25

1.42825

112.7

124

206.3

0.96725 25

1.42825

242.4

127

HC(OCH2CH2CH3)3

190.28

0.880520 4

1.407220

1085mm

(C4H9OCH2CH2O)3P(O)

398.48

1.006

1.435920

2284mm

(ClCH2CH2O)3SiH

267.6

1.288620 4

1.457720

1182mm

93

42

 112

v s alc; misc eth s aq, alc, eth s aq

misc aq, alc, eth

t416 t417 t418 t419 t420 t421 t422 t423

Tris(2-chloroethyl) phosphate Tris(2-chloroethyl) phosphite Tris(2,6-dichlorophenyl) phosphate Tris(dimethylamino)methane Tris(dimethylamino)methylsilane Tris(2-ethylhexyl) phosphite Tris(heptafluoropropyl)-s-triazine Tris(hydroxymethyl)aminomethane

Triphenylsilyl azide, a320 Tripropyl borate, t406

12, 337

1.390

1.472120

330

232

1.35320 4

1.486320

1152mm

190

misc alc, bz, eth

185

i aq

(ClCH2CH2O)3P(O)

285.49

(ClCH2CH2O)3P

269.49

(Cl2C6H3O)3P(O)

533.09

CH[N(CH3)2]3

145.25

1.436020

[(CH3)2N]3SiCH3

175.4

0.85022 4

1.43222

[CH3(CH2)3CH(CH2CH3)CH2O]3P

418.6

0.90220 4

1.449420

1640.3mm

585.1

1.715825

1.715825

165

(HOCH2)3CNH2

121.14

208–210

4, 303

Tripropylsilyl chloride, c258 TRIS, t423

42– 4312mm 11 5617mm

172

22010mm

Tris(dimethylamino)silyl chloride, c257a 1,1,1-Tris(hydroxymethyl)ethane, h141

1.389

1.390

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. t424

t425 t426

t427

t428

t429

t430 t431 t432

Name 2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid 1,1,1-Tris(hydroxymethyl)ethane 3-[N-Tris(hydroxymethyl)methylamino]2-hydroxypropanesulfonic acid 3-[Tris(hydroxymethyl)-methylamino]1-propanesulfonic acid N-[Tris(hydroxymethyl)methyl]glycine Tris(2-methoxyethoxy)methylsilane Tris(2-methoxyethoxy)vinylsilane Tris(2-methylallyl)amine Tris(pentafluoroethyl)-s-triazine

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

(HOCH2)3CNHCH2CH2SO3H

229.25

CH3C(CH2OH)3

120.15

(HOCH2)3CNHCH2CH(OH)CH2SO3H

259.3

226

(HOCH2)3CNHCH2CH2CH2SO3H

243.28

240 d

(HOCH2)3CNHCH2COOH

179.17

184 d

CH3Si(OCH2CH2OCH3)3

268.4

1.04520 4

1.42020

14516mm

H2C ¨ CHSi(OCH2CH2OCH3)3 [H2C ¨ C(CH3)CH2]3N

280.38

1.03425 4

1.42725

284–286

65

0.794

1.457520

53

1.650625

1.313125

83– 8515mm 121–122

173.91 435.1

223–225

1, 520

43, 462

Solubility in 100 parts solvent

t433 t434 t435 t436

1,3,5-Trithiane Trithiocarbonic acid 1,2,4-Trivinylcyclohexane L-()-Tryptophan

t437

L-Tyrosine

t438

L-Tyrosine hydrazide

u1 u2 u3 u4 u5

Undecanal Undecane Undecanoic acid 1-Undecanol 2-Undecanone

u6

6-Undecanone

u7 u8

10-Undecenal 1-Undecene

(HS)2C(S) (H2C ¨ CH)3C6H9

(HO)C6H4CH2CH(NH2)COOH HOC6H4CH2CH(NH2)CONHNH2 CH3(CH2)9CHO CH3(CH2)9CH3 CH3(CH2)9COOH CH3(CH2)10OH CH3(CH2)8COCH3 CH3(CH2)4CO(CH2)4CH3 H2C ¨ CH(CH2)8CHO CH3(CH2)8CH ¨ CH2

Tris(7-methylnonyl) phosphite, t308 Trityl alcohol, t398 Tryptamine, a170

138.27 110.21 162.28

19, 382 3, 221

204.23

22, 546

181.19

14, 605

280–285 d  300 d

195.22

141, 665

196–198

170.30 156.31 186.30 172.31 170.30

1, 712 1, 170 2, 358 1, 427 1, 173

0.825 0.740220 4 0.8907 0.832420 0.829

1.432220 1.417320 1.429445 1.440220 1.428020

4 25.6 28.5 15.9 11–12

1155mm 195.9 228160mm 242.8 231–232

96 60

170.30

1, 174

0.831

1.428020

14.6

228

88

168.28 154.29

1, 225

0.810 0.76320 4

1.442720 1.426120

49.2

192.7

Tyramine, a173 Umbelliferone, h109 Undecyl alcohol, u4

1.48320 4 0.836

1.822520 1.478020

216–218 26.9 57.8 8820mm

s bz; sl s alc, eth d aq, alc; sl s eth 68 1 aq; s hot alc, alk; i eth, chl 0.03 aq; 0.01 alc; s alk; i eth

 112 88

i aq; s alc, eth i aq; misc alc, eth s alc, chl, eth; i aq 0.02 aq; s alc s alc, bz, chl, eth, acet; i aq i aq; v s alc, eth

92

Undecyl-10-en-1-oic acid, u9 Undecylenic aldehyde, u7 Undecylic aldehyde, u1

i aq; misc alc, eth

1.391

1.392

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No. u9 u10 u11 u12 u13 u14 v1 v2 v3 v4 v5 v6 v7 v8 v9 v10 v11 x1 x2 x3

Name 10-Undecenoic acid 10-Undecen-1-ol 10-Undecenoyl chloride Urea Uric acid Uridine L-Valine Vinyl acetate 5-Vinylbicyclo[2.2.1]-2-heptene Vinyl crotonate Vinylcyclohexane 4-Vinyl-1-cyclohexene 1-Vinylimidazole 5-Vinyl-2norbornene 2-Vinylpyridine 4-Vinylpyridine N-Vinyl-2pyrrolidinone Xanthene Xanthen-9carboxylic acid 9-Xanthenone

Formula weight

Beilstein reference

Density

Refractive index

Melting point

H2C ¨ CH(CH2)8COOH H2C ¨ CH(CH2)9OH H2C ¨ CH(CH2)8COCl

184.28 170.30 202.73

2, 458 1,452 2, 459

0.90724 4 0.85015 0.944

1.449320 1.450020 1.453220

24.5 2

1372mm 245 12210mm

(H2N)2CO

60.06 168.11 244.20 117.15

3, 42 26, 513 31, 23 4, 427

1.3218 4 1.89320

132.7  300 165 315

d  mp d subl

86.09 120.19

21, 63

0.931820 4 0.84

1.395920 1.4802

92.8 80

72.5 141

6

23, 1263 51, 35 51, 63 234, 569

0.940 0.83020 4 1.039

1.448820 1.446320 1.464020 1.530820

27 21 20 81

0.8411

1.480220

5010mm 128 126–127 78– 7913mm 141

0.975 0.975 0.980

1.549020 1.550020 1.512020

158–159 6515mm 9313mm

43 51 93

Formula

(CH3)2CHCH(NH2)COOH H2C ¨ CHOOCCH3

CH3CH¨CHCOOCH¨CH2 112.13 C6H11CH ¨ CH2 110.20 108.18 94.12 120.20 (C5H4N)CH ¨ CH2 (C5H4N)CH ¨ CH2

1.230

101 80

105.14 105.14 111.14

20, 256 202, 170

182.22

17, 73

101

226.23

122, 279

217 d

196.21

17, 354

174

Boiling point

Flash point 148 93 93

Solubility in 100 parts solvent s alc, chl, eth; i aq

100 aq; 20 alc s alk; i aq, alc, eth s aq; hot alc, pyr 8.8 aq; v sl s alc, eth 2 aq; misc alc, eth

27 v s alc, chl, eth sl s hot aq, hot alc

310–312

s bz, eth; sl s alc, aq s hot alc, eth

350730mm

0.5 alc; v s chl

Uracil, p268 5-Ureidohydantoin, a77 Urethane, e91 Valeraldehyde, p27 Valeric acid, p36 -Valerolactone, p40 Valerone, d531 Valeronitrile, p33 Valeryl chloride, p44 Valinols, a213, a214

Vanillic acid, h132 Vanillin, h131 o-Vanillin, h130 Vanillyl alcohol, h135 Veratraldehyde, d430 Veratric acid, d434 Veratrole, d431 Veronal, d280 Vinylacetic acid, b403 Vinyl bromide, b284

Vinyl 2-butenoate, v4 Vinyl chloride, c109 Vinylidene chloride, d178 Vinyltrimethylsilane, t380 Vinyltris (2-methoxyethoxy)silane, t430 Vitamin B1, t139 Vitamin B2, r4 Vitamin C, a312 Xanthone, x3

1.393

1.394

TABLE 1.15 Physical Constants of Organic Compounds (continued )

No.

Name

Formula

Formula weight

Beilstein reference

Density

Refractive index

Melting point

Boiling point

Flash point

x4

o-Xylene

C6H4(CH3)2

106.17

5, 362

0.880220 4

1.505420

25.2

144.4

32

x5

m-Xylene

C6H4(CH3)2

106.17

5, 370

0.868415 4

1.497220

47.9

139.1

25

x6

p-Xylene

C6H4(CH3)2

106.17

5, 382

0.861120 4

1.495820

13.3

138.4

30

x7 x8

Xylitol D-()-Xylose

HOCH2(CHOH)3CH2OH

152.15 150.13

1, 531 31, 47

1.5350

x9

m-Xylylenediamine

C6H4(CH2NH2)2

136.20

13, 186

1.032

265745mm

 112

Xylene-,-diol, b18 Xylenols, d579, d580, d581, d582, d583, d584

o-Xylyl bromide, b368 Xylyl chlorides, c258, c259, c260

95–97 144–145 1.570920

p-Xylylene glycol, b18

Solubility in 100 parts solvent misc alc, eth; 0.017 aq misc alc, eth; 0.02 aq v s eth; s alc; 0.02 aq s aq 117 aq; s hot alc, pyr

SECTION 2

INORGANIC AND ORGANOMETALLIC COMPOUNDS

Table 2.1 Physical Constants of Inorganic Compounds . . . . . . .

2.1

2.2

2.2

SECTION 2

This section summarizes the properties of various chemical compounds commonly encountered in organic chemistry that are often referred to either as inorganic or organometallic. In some cases, the distinction is artificial and the reader should refer to Section 1 if the expected compound is not presented here. Most compounds containing metals are collected here, rather than in Section 1. TABLE 2.1 Physical Constants of Inorganic Compounds Explanation of column headings Names, while following the IUPAC nomenclature, are generally alphabetized by the central atom to facilitate their location. An example of the table organization is given below for Al3C4, aluminum tetracarbide. It is entered in Table 2.1 as follows: Main heading Subgrouping Actual table listing

Aluminum carbide Aluminum (tetra-) carbide (tri-)

Solvates are listed under the entry for the anhydrous salt. Hydrazine hydrate, H2N ˆ NH2·H2O is listed under hydrazine. Magnesium sulfate heptahydrate (epsom salt) is listed under Magnesium, using the subgroup sulfate 7water. Inorganic acids are entered under hydrogen, For example, HF is listed under Hydrogen, using the subgroup fluoride. Where an elemental designation would be confusing or inappropriate, the compound is listed alphabetically as in the case of hydroxylamine, HONH2. Abbreviations used in the Table

, greater than , alpha position a, acid abs, absolute acetone, acet alc, alcohol alk, alkali, (aq NaOH) anhyd, anhydrous aq, aqueous aq reg, aqua regia atm, atmosphere bz, benzene c, solid state

ca, approximately chl, chloroform conc, concentrated cub, cubic d, decompose(s) dil, dilute DMF, dimethylformamide eth, diethyl ether EtOH, ethanol expl, explodes, explosive fcc, face-centered cubic

g, gas glyc, glycerol h, hot hex, hexagonal hyd, hydrolysis i, insoluble ign, ignites lq, liquid MeOH, methanol min, mineral misc, miscible org, organic PE, petroleum ether

pyr, pyridine s, soluble satd, saturated sl, slightly soln, solution solv, solvent(s) subl, sublimes tetr, tetragonal THF, tetrahydrofuran tr, transition v, very vac, vacuo or vacuum viol, violently

Formula Weights are based on the International Atomic Weights of 1973 and are computed to the nearest hundredth of an a.m.u. Density values are given at room temperature unless otherwise indicated by a superscript figure indicating a temperature in C. Thus, 2.48715 indicates a density of 2.487 for the named substance at 15 C. For gases density values are given in grams per liter (g · L1). Melting Point values are recorded in C. In certain cases decomposition is indicated with the letter “d” that either precedes or follows the number. The value 250 d indicates that the substance melts at 250 C with decomposition. The value d 250 indicates that decomposition only occurs at 250 C and higher temperatures. Where a value such as “6H2O, 150” is given, it indicates a loss of 6 moles of water per formula weight of the compound at a temperature of 150 C. Boiling Point values are given at atmospheric pressure (760 mm of mercury) unless otherwise indicated; a value of 82 means that the boiling point is 82 C at 760 mm Hg. A value of 8215 means that the boiling point is 82 C when the pressure is 15 mmHg. The specification “subl 550” indicates that the compound sublimes at 550 C. Solubility is given in parts by weight (of the formula weight) per 100 parts by weight of the solvent. If the solvent is unspecified, it is water. If no temperature is specified, the solubility is for the substance at room temperature. Other temperatures (in C) are indicated by superscript. The symbols of the common mineral acids represent aqueous solutions of those acids.

TABLE 2.1 Physical Constants of Inorganic Compounds

Name Aluminum acetylacetonate ammonium bis(sulfate) 12-water bis(acetylsalicylate) bromide butoxide, secbutoxide, tert(tetra-) carbide, trichlorate chloride

2.3

chloride 6-water ethoxide fluoride hydroxide iodide isopropoxide nitrate 9-water oxide phenoxide potassium bis (sulfate 12-water propoxide sodium bis(sulfate) 12-water

Formula

Formula weight

Density 2.70 1.27 1.64

Melting point, C 660.1 subl 193 (vac) 12 H2O, 250

Boiling point, C

Al Al(C5H7O2)3 AlNH4(SO4)2·12H2O

26.98 324.31 453.33

2450 314 d  280

Al(OOCC6H4OCOCH3)2OH AlBr3 Al(C4H9O)3 Al(C4H9O)3 Al4C3 Al(ClO3)3 AlCl3

402.30 266.71 246.33 246.33 143.96 277.35 133.34

2.6410 0.967 1.02520 0 2.36

97.5 subl 180 2100

d  2200

2.44

1942.5 atm

subl 181

AlCl3·6H2O Al(C2H5O)3 AlF3 Al(OH)3 AlI3 Al(C3H7O)3 Al(NO3)3·9H2O Al2O3 Al(C6H5O)3 AlK(SO4)2·12H2O

241.43 162.14 83.98 78.00 407.71 204.25 375.13 101.96 306.27 474.39

2.40 1.4220 0 2.88225 4 2.42 25 3.98 1.034620 0 3.965 1.23 1.75720

d 100 134 1040 H2O, 300 191 118.5 73 2054 d 265 9H2O, 92

Al(C3H7O)3 AlNa(SO4)2·12H2O

204.25 458.28

1.057820 0 1.67520

106 61

Solubility in 100 parts solvent s HCl, H2SO4, alk i aq; v s alc; s bz, eth 15 aq; i alc v sl s aq, alc, eth

253.3 200–20630 mm

20514 mm subl 1276 360 13510 mm d 135 2980 12H2O, 200 24814 mm

d viol aq; s alc, acet, bz CS2 v s org solv (flash point 27 C) v s org solv d to CH4 in aq (fire hazard) v s aq; s alc 70 aq (viol); 10012 abs alc; s CCl4, eth; sl s bz 8320 aq; 25 abs alc; s eth s hot aq (d); v sl a alc, eth 0.5625 aq; i a, alk, alc, acet i aq; s a,alk s aq(d); s alc, CS2, eth d aq; s alc, bz, chl, PE 6425 aq; 100 alc; s acet i aq; v sl s a, alk d aq; s alc, chl, eth 11.420 aq d aq; s alc 11015 aq

2.4

TABLE 2.1 Physical Constants of Inorganic Compounds (continued)

Name Aluminum stearate sulfate sulfate 18-water tetrahydroborate Amidosulfuric acid Ammonia d3 or [2H] Ammonium acetate benzoate boranate, tetrafluorobromide

Formula

Formula weight

Al(C18H35O2)3 Al2(SO4)3 Al2(SO4)3·18H2O Al(BH4)3 H2NSO3H NH3

877.42 342.15 666.45 71.53 97.09 17.03

ND3 or N2H3

20.05

NH4C2H3O2 NH4C7H5O2 NH4BF4 NH4Br

77.08 139.16 104.84 97.95

carbamate NH4COONH2 carbonate 1-water (NH4)2CO3·H2O cerate(IV), hexanitrato- (NH4)2[Ce(NO3)6] chloride NH4Cl chromate (NH4)2CrO4 chromium(III) bis(sulfate)NH4Cr(SO4)2·12H2O 12-water citrate (NH4)3C6H5O7 copper(II) tetrachloride Cu(NH4)2Cl4·2H2O 2-hydrate dichromate(VI) (NH4)2Cr2O7

Density

1.010 2.710 1.6917 2.126 0.718820 g · L1 0.843720 g · L1 1.1720 1.260 1.8715 2.429

Melting point, C

Boiling point, C

103 d 770 d 86.5 64.5 205 77.75

44.5 d 33.42

74.33

31.05

114 d 198 subl 452 (under pressure) subl 60 d 20

d subl 160

78.07 114.10 548.23 53.49 152.08 478.34

1.527 1.9112 1.72

subl 340 d 180 94

243.22 277.46

1.48 1.993

d 2H2O, 110

252.06

2.15525 4

d 170

d 397 (vac)

Solubility in 100 parts solvent

i aq; s alc, bz, alk 36.420 aq; sl s alc 870 aq; i alc d aq 14.7 aq 89.9 aq; 13.220 alc; s eth, org solv

1484 aq; 7.915 MeOH; s alc 2015 aq; 2.8 alc; s glyc; i eth 2516 aq 7620 aq; s acet, alc, eth v s aq; sl s alc; i eth 10015 aq; i alc 13520 aq; s alc, HNO3 2615 aq; 0.619 abs alc; i acet, eth 3420 aq; sl s MeOH, acet; i alc 7.20 aq

d120

100 aq; sl s alc 4020 aq; s alc 3620 aq; s alc (flammable)

1.45120 4

d 99

1.00925 1.280

subl 116 21–22 d100 d 35

2.5

dithiocarbamate diuranate(VI) fluoride formate hexadecanoate hexafluoroaluminate hydrogen carbonate hydrogen citrate hydrogen difluoride hydrogen oxalate 1-water hydrogen phosphate hydrogen phosphate, dihydrogen sulfate hydrogen sulfide hydrogen sulfite

NH4S ˆ CS ˆ NH2 (NH4)2U2O7 NH4F NH4OOCH NH4OOC(CH2)14CH3 (NH4)3AlF6 NH4HCO3 (NH4)2HC6H5O7 NH4HF2 NH4HC2O4·H2O (NH4)2HPO4 NH4H2PO4 NH4HSO4 NH4HS NH4HSO3

110.19 624.22 37.04 63.06 273.45 195.10 79.06 226.19 57.04 125.08 132.05 115.03 115.11 51.11 99.10

1.78 1.58 1.48 1.50 1.556 1.619 1.80319 1.78 1.17 2.03

hydroxide iodide iron(II) bis(sulfate) 6-water molybdate(VI)(6-) 4-water, heptanitrate octadecanoate octanoate oxalate 1-water palladate(II) tetrachloroperchlorate peroxodisulfate phosphate, hexafluorophosphinate picrate platinate(IV), hexachlorosilicate, hexafluoro-

NH4OH NH4I Fe(NH4)2(SO4)2·6H2O

35.05 144.95 392.14

2.51425 1.86420 4

125.6 H2O, 170 d 155 d 190 146.9 d 25 subl 150 (in N2) 77 subl 551 d 100

(NH4)6Mo7O24·4H2O

1235.86

2.498

NH4NO3 NH4OOC(CH2)16CH3 NH4OOCC7H15 (NH4)2C2O4·H2O (NH4)2PdCl4 NH4ClO4 (NH4)2S2O8 NH4PF6 NH4PH2O2 NH4C6H2N3O7 (NH4)2PtCl6 (NH4)2SiF6

80.04 301.50 161.24 142.11 284.29 117.50 228.18 163.00 83.03 246.14 443.89 178.14

1.72525

1.50 2.170 1.95 1.982 2.18012 4 1.634 1.719 3.065 2.011

d 180

subl

d 350

v s aq; s alc; sl s eth v sl s aq, alk; s acids 1000 aq; s alc 14320 aq; s alc, eth s aq; sl s bz; i alc, acet v s aq 2220 aq; i alc, acet 100 aq; sl s alc v s aq; sl s alc s aq; i bz, eth 6920 aq; i alc, acet 3720 aq; sl s alc; i acet 100 aq; i alc, acet 1280 aq; s alc; sl s acet; i bz 720 aq

220 (vac)

misc aq 17220 aq; v s alc, acet 3620 aq; i alc

H2O, 90

d 190

43 aq; s a; i alc

169.6 21–22 d on standing d 70 d d 240 d 120 d 200 d d d

21011 mm

19220 aq; 3.820 alc; 1720 MeOH sl s aq; s alc; i acet v s aq, alc, acet; sl s eth 5.120 aq v s aq; i abs alc 2220 aq; s MeOH; sl s alc, acet 580 aq 7520 aq; s alc, acet 100 aq; 5 alc; i acet 1.120 aq; sl s alc 0.520 aq 18.620 aq; i alc, acet

expl 180 d 240 expl 423

2.6

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Ammonium sulfamate sulfate sulfide DL-tartrate tetraborate 4-water thiocyanate thiosulfate vanadate(V)(1-) Antimony (III) chloride (V) chloride (III) fluoride (V) fluoride

Formula

Formula weight

NH4SO3NH2 (NH4)2SO4 (NH4)2S (NH4)2C4H4O6 (NH4)2B4O7·4H2O NH4SCN (NH4)2S2O3 NH4VO3

114.13 132.14 68.14 184.15 263.44 76.12 148.20 116.98

SbCl3 SbCl5 SbF3 SbF5

Density

Melting point, C

Boiling point, C

d 160

1.601

131 d  280 d d

1.305 1.679 2.326

149.6 d 150 d 200

d 170

228.11 299.02 178.75 216.74

3.1420 4 2.33620 4 4.37920 20 23 2.99

73.4 3.5 292 8.3

223.5 140 376 141 18.4 1425

1.76920

Solubility in 100 parts solvent

v s aq; sl s alc 43.525 aq; i alc, acet v s aq; s alc 5815 aq; sl s alc s aq; i alc 1280 aq; v s alc; s acet v s aq 0.4820 aq 1020 aq; s alc, bz, chl d aq; s HCl, chl, CCl4 44420 aq d viol aq; s HOAc; forms solids with alc, bz, CS2, eth 200 mL aq; s CS2 v sl s aq; s HCl, KOH v sl s aq; sl s warm KOH, eth 8.320 aq; 6.7 glyc; i alc

hydride (III) oxide (V) oxide potassium oxide tartrate 0.5-water (III) sulfide (V) sulfide Argon

SbH3 Sb2O3 Sb2O5 K(SbO)C4H4O6·O.5H2O

124.77 291.50 323.50 333.93

4.3615 5.2 2.78 2.607

91.5 655 O2, 300 d 100

Sb2S3 Sb2S5 Ar

339.69 403.82 39.95

4.64

546 189.38

185.87

Arsenic (III) chloride (III) oxide dimer

As AsCl3 As4O6

74.92 181.28 395.68

1.7824 g · L1 5.72 2.149725 4 4.15

0.00220 aq d; s H2SO4 i aq; s HCl, d NaOH 3.3620 mL aq

81728 atm 16 313

subl 612 130.2 465

i aq; s HNO3 d aq; misc chl, CCl4, eth; s alc 1.820 aq; s alc

(V) oxide (III) sulfide Barium acetate 1-water benzenesulfonate carbonate chlorate 1-water chloride fluoride hydrogen phosphate hydroxide 8-water manganate(VI)(2-) nitrate nitrite 1-water oxide perchlorate 3-water permanganate peroxide sulfate sulfide sulfite thiocyanate 2-water thiosulfate 1-water Beryllium bromide chloride fluoride hydride hydroxide iodide oxide sulfate 4-water

As2O5 As2S3

229.84 246.04

4.32 3.46

d 800 300–325

Ba(C2H3O2)2·H2O Ba(O3SC6H5)2 BaCO3 Ba(ClO3)2·H2O BaCl2 BaF2 BaHPO4 Ba(OH)2·8H2O BaMnO4 Ba(NO3)2 Ba(NO2)2·H2O BaO Ba(ClO4)2·3H2O Ba(MnO4)2 BaO2 BaSO4 BaS BaSO3 Ba(SCN)2·2H2O BaS2O3·H2O Be BeBr2 BeCl2 BeF2 BeH2 Be(OH)2 BeI2 BeO BeSO4·4H2O

273.46 451.70 197.35 322.26 208.25 175.34 233.32 315.48 256.28 261.35 247.37 153.34 390.29 375.21 169.34 233.40 169.40 217.40 289.53 267.48 9.01 168.83 79.92 47.01 11.03 43.03 262.82 25.01 177.14

2.19

d 150

4.43 3.18 3.856 4.89 4.16515 2.1816 4.85 3.24 3.17320 5.72 2.74 3.77 4.96 4.5015 4.2515

d 1360 H2O, 120 962 1368 d 410 78

2.28618 3.518 1.86 3.46525 1.89925 1.98625 4 1.92 4.2 3.01 1.71311

575 d 115 2013 d 400 d 200 450 1580 2227 d d 160 d 220 1277 506–509 399 552 H2, 220 134 d 480 2408() 4H2O, 270

707

O2, 250 2029 2272

d 3088 O2, 800

2484 521 482 1175

482 3787 d 580

6620 aq; s alc i aq; s alk; slowly s hot HCl 7620 aq; 0.14 alc s aq; sl s alc 0.002 aq; s a 3420 aq 3620 aq 0.1620 aq 0.01 aq; s a 3.920 aq v sl s aq 920 aq 7320 aq; i alc 3.520 aq 19825 aq; s MeOH; sl s alc, acet 6211 aq 1.50 aq 0.0002 aq 7.922 aq d 0.0220 aq 17025 aq 0.2120 aq i q; s a, alk v s aq; s alc; 19 pyr 42 aq; s alc, eth, CS2, pyr; i bz v s aq but slow d slowly aq; d rapidly a s hot conc a, alk hyd aq; s alc, eth, CS2 s conc H2SO4 3920 aq; i alc

2.7

2.8

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Bismuth chloride, trifluoride, pentahydroxide (III) nitrate 5-water (III) oxide Boron bromide, trichoride, trifluoride, trifluoride-1-diethyl ether fluoride-1-methanol oxide Bromine fluoride, triCadmium acetate chloride iodide oxide sulfate-water (3/8) sulfide Calcium acetate arsenate(V)

Formula

Formula weight

Density

Melting point, C

Boiling point, C

BiCl3 BiF5 Bi(OH)3 Bi(NO3)3·5H2O Bi2O3

315.34 303.98 260.00 485.07 495.96

4.75 5.425 4.36 2.83 8.76

ca 232 151 H2O, 100 d 30 817

447 230

BBr3 BCl3 BF3 BF3·O(C2H5)2 BF3·CH3OH B2O3 Br2 BrF3

250.57 117.19 67.81 141.94 131.89 69.62 159.81 136.90

2.6950 1.3512 4 2.99 g · L1 1.12525 4 1.203 2.46 3.1028 2.80325

46.0 107 127.1 60.4

91.3 18 100.4 125.7 594 mm 2065 58.75 125.74

Cd(C2H3O2)2 CdCl2 CdI2 CdO 3CdSO4·8H2O

230.50 183.32 366.21 128.40 769.56

2.341 4.047 5.67030 8.15 3.09

256 568 387 subl 1497 H2O, 40

CdS

144.46

4.82 hex

Ca(C2H3O2)2 Ca3(AsO4)2

158.17 398.08

d  160 3.620

450 7.3 8.77

1890

d 961 796 forms monohydrate 80 sub 1380 (in N2)

Solubility in 100 parts solvent

d aq; s HCl, alc, eth, acet d viol aq giving O3 d aq; s a d aq; s, acet i aq; s a d aq d aq, alc 1050 mL aq; s bz, chl, CCl4 d aq sl s aq 3.620 aq; v s alc, chl, eth, CS2 d viol aq; d alk v s aq 12025 aq 8520 aq; s alc, acet, eth i aq; s a 94.425; i alc 3.1318 aq; s a

370 aq; i alc, acet, bz 0.01325 aq

bromide carbide, dicarbonate chlorate chloride chloride 6-water citrate 4-water cyanamide cyanide diphosphate fluoride formate glycerophosphate hydrogen phosphate, di1-water hydroxide hypochlorite iodate 6-water lactate 5-water nitrate nitrite 4-water oleate oxide palmitate pantothenate (vitamin B3) peroxide phenoxide phosphate salicylate 2-water selenate 2-water stearate

CaBr2 CaC2 CaCO3 Ca(ClO3)2 CaCl2 CaCl2·6H2O Ca(C6H6O7)·4H2O CaCN2 Ca(CN)2 Ca2P2O7 CaF2 Ca(OOCH)2 Ca[C3H5(OH)2]PO4 Ca(H2PO4)2·H2O

199.90 64.10 100.09 206.99 110.99 219.08 570.51 80.11 92.12 254.10 78.08 130.12 210.16 252.07

3.353 2.22 2.930

Ca(OH)2 Ca(OCl)2 Ca(IO3)2·6H2O Ca(C3H5O3)2·5H2O Ca(NO3)2 Ca(NO2)2·4H2O Ca(C18H33O2)2 CaO Ca(C16H31O2)2 Ca[O2CH2CH2HOCH(OH)C(CH3)2CH2OH]2 CaO2 Ca(OC6H5)2 Ca3(PO4)2 Ca(C7H5O3)2·2H2O CaSeO4·2H2O Ca(C18H35O2)2

74.09 142.99 497.98 308.30 164.09 204.5 603.01 56.08 550.93 476.55

2.24 2.35

72.08 226.28 310.18 350.34 219.07 607.04

2.9225 4

d 275

3.14

1730 2H2O, 120 2H2O, 200 179–180

2.15 1.71 2.2920 4 3.09 3.180 2.015 2.22018 4

2.50418 1.67400 3.25

2.6820 4

765 d 900 340 772 6H2O, 200 4H2O, 120 1340 d 350 1230 1418 d d  170 H2O, 109 H2O, 522 100 d d 35 3H2O, 100 561 2H2O, 44 83–84 2927 d 155 d 195–196

806–812 2300

1940

subl 1150

2510

d 203

5H2O, 120

d 140 3500

d 240 d 698

14320 aq; v s alc, acet d aq giving C2H2 0.001320; s a 178 aq; s alc, acet 7520; s alc, acet 53620 aq; s alc 0.8518 aq; 0.006518 alc i aq; no known solv d aq i aq; s a 0.00220 aq; sl s a 16.620 aq; i alc 1.720 aq, i alc 1.830 aq 0.1710 aq; s a d aq evolving Cl2; i alc 0.2420 aq; i alc 5.415 aq; v sl s alc 15230 aq 84.518 aq; sl s alc 0.04 aq; s bz, chl; v sl s alc 0.1325 aq; s a 0.003 aq; sl s bz, chl; i alc, eth 35 aq; sl s alc, acet

sl s aq; s a sl s aq, alc 0.0325; s a; i alc 2.815 aq; 0.01516 EtOH 9.225 aq 0.00415 aq; s hot pyr; i chl, eth

2.9

2.10

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Calcium succinate 3-water sulfate sulfate hemihydrate sulfate 2-water sulfite 2-water DL-tartrate 4-water tetrahydridoaluminate thiocyanate 3-water Carbon (graphite) bromide, tetrachloride, tetrahydride, tetraiodide, tetraoxide, mono-

Formula

Formula weight

CaC4H6O4·3H2O CaSO4 CaSO4·0.5H2O CaSO4·2H2O CaSO3·2H2O CaC4H4O6·4H2O Ca(AlH4)2 Ca(SCN)2·3H2O

212.22 136.14 145.15 172.17 156.17 260.21 102.10 210.29

C CBr4 CCl4 CH4 CI4 CO

12.01 331.65 153.82 16.04 519.63 28.01

oxide di-

CO2

44.01

(tri-) oxide, diselenide, di-

C3O2 CSe2

sulfide, di-

CS2

Density

2.960 2.32

Melting point, C

Boiling point, C

Solubility in 100 parts solvent

1.2820 aq; s a; i alc 0.20 aq; s a 0.320 aq; s a, glyc 0.2620 aq; s a, glyc 0.004 aq; s a; sl s alc 0.004525 aq; sl s alc ign moist air; d viol aq, alc 150 aq; v s alc

1400 H2O, 163 2H2O, 163 2H2O, 100 4H2O, 200 d 160 400063.5 atm 90.1 22.9 182.48 d 171 205.05

3930 190 76.7 161.49 191.49

i aq, alc i aq; s alc, chl, eth i aq; s alc, chl, eth i aq; s bz sl hyd aq; s alc, bz, eth 2.1 mL aq; s alc, bz

56.2 solid subl 112.19 43

78.44

3115 mL aq

68.03 169.93

2.2520 3.42 1.586720 20 0.415164 4.34 0793 (lq) 1.250 g · L1 (gas) 1.5679 (c) 1.975 g · L1 1.11404 2.66325 4

6.4 125.1

76.14

1.26122

111.6

46.26

d aq to malonic acid i aq; d alc, pyr; misc CCl4; s acet, eth 0.2920 aq; s alc, eth

Carbonic acid Carbonyl chloride fluoride sulfide Cerium (III) chloride (IV) fluoride (IV) oxide (IV) sulfate Cesium bromide carbonate chloride fluoride hydroxide iodide nitrate oxalate selenate sulfate Chlorine fluoride, tri(di-) oxide oxide, di(di-) oxide, hepta-

2.11

Chlorosulfonic acid Chromium (II) acetate carbonyl, hexa-

H2CO3(CO2  H2O)

62.03

COCl2 COF2 COS

98.92 66.01 60.07

1.392 1.139114 1.0730 g · L1

127.8 114.0 138.81

7.6 83.3 50.23

hyd aq; s bz hyd aq 5420 mL aq; s alc, CS2

CeCl3 CeF4 CeO2 Ce(SO4)2

246.48 216.12 172.13 332.24

3.92 4.80

8.7 650

1730 d 550

3.91

d 195

10020 aq; 30 alc; s acet i aq; s a i aq; s a hyd aq; s H2SO4

CsBr Cs2CO3 CsCl CsF CsOH CsI CsNO3 Cs2C2O4 Cs2SeO4 Cs2SO4

212.81 325.82 168.36 151.90 149.91 259.81 194.91 353.82 408.77 361.87

4.44

1300

3.988 4.115 3.675 4.510 3.68520 4 3.23015 4.452820 4 4.243

635 d 610 645 703 272 621 414

10718 aq 26015 aq; 1120 alc; s eth 18720 aq; 3425 MeOH; v s alc 32218 aq 38615 aq; s alc 7720 aq; s EtOH; i acet 2320 aq; s acet; v sl s alc 313 aq 24412 aq 17920 aq; i alc, acet, pyr

ClF3

92.45

1.82511

76.28

11.74

Cl2O ClO2 Cl2O7

86.91 67.46 182.90

3.022 1.6420 1.80525

120.6 59.6 91.5

2.1 10.9 83.6

HSO3Cl

116.52

1.75320 4

80

158

hyd viol aq; glass wool and org matter ign 3.520 aq (hyd to HClO); s CCl4 11.210 aq d aq; expl on concussion or contact with flame or I2 d viol aq to HCl  H2SO4

Cr(C2H3O2)2 Cr(CO)6

170.10 220.06

1.7718

d 130

expl 210

sl s aq, alc; i eth i aq, alc, eth

known in soln only

1324 1231 990 ca 1280 d 849

1019

2.12

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Chromium (II) chloride (III) chloride (III) fluoride (III) nitrate 9-water (III) oxide (IV) oxide (VI) oxide (III) phosphate 6-water (II) sulfate 7-water (III) sulfate 18-water Chromyl chloride Cobalt (II) acetate 4-water (III) acetate (II) bromide (II) carbonate (II) chloride (II) fluoride (III) fluoride (II) hydroxide (II) iodide (II) nitrate 6-water (II) oxalate (II) oxide

Formula

Formula weight

Density

2.878 2.7615 3.8

Melting point, C

CrCl2 CrCl3 CrF3 Cr(NO3)3·9H2O Cr2O3 CrO2 CrO3 CrPO4·6H2O CrSO4·7H2O Cr2(SO4)3·18H2O

122.90 158.35 108.99 400.15 152.02 83.99 99.99 255.06 274.17 716.45

5.21 4.89 2.70 2.12114

815 877 1100 60 2330 O2, 300 198 100

1.7

d 100

CrO2Cl2

154.90

1.92

96.5

Co(C2H3O2)2·4H2O Co(C2H3O2)3 CoBr2 CoCO3 CoCl2 CoF2 CoF3 Co(OH)2 CoI2 Co(NO3)2·6H2O CoC2O4 CoO

249.08 236.07 218.75 118.94 129.84 96.93 115.93 92.95 312.74 291.04 146.95 74.93

1.70519

4H2O, 140 d 100 678 (in N2) d 740 1127

4.90925 4 4.13 3.356 4.46 3.88 3.59715 4 5.68 1.87 3.02125 4 6.45

d 505 d 55 d 250 1805

Boiling point, C

1300 subl 947 subl d 100 3000 d 250

117

1087 1739

570 (vac) d 74

Solubility in 100 parts solvent

v s aq i aq, alc, acet, eth i aq, alc; s HF 20815 aq; s alc i aq, alc i aq; s HNO3 16720 aq; may ign org materials i aq; v s a, alk; sl s HOAc 230 aq 22020 aq d aq; s eth s aq; 2.115 MeOH s aq, alc, HOAc 11220 aq 0.1815 aq; s a 5320 aq 1.3620 aq; s a d aq; i alc, bz, eth 0.0018 aq; s a 203 aq 15530 aq; v s alc 0.00218 aq; s a i aq; s a

(II,III) oxide (II) sulfate 7-water Copper (II) acetate hydrate (II) acetate–metaarsenite

2.13

Co3O4 CoSO4·7H2O

240.80 281.10

6.07 2.0325 4

d 900 96.8

7H2O, 420

199.65 1013.77

1.882

115

d 240

8 aq; 0.48 MeOH; sl s eth, glyc i aq; s a, NH4OH

(I) bromide (II) bromide (II) chlorate 6-water (I) chloride (II) chloride (II) chloride 2-water (I) cyanide (II) fluoride formate hydroxide (I) iodide (II) nitrate 3-water (II) oleate (I) oxide (II) oxide (II) perchlorate (II) stearate (II) sulfate (II) sulfate 5-water Cyanogen azide

Cu(C2H3O2)2·H2O Cu(C2H3O2)2·3Cu(AsO2)2 CuBr CuBr2 Cu(ClO3)2·6H2O CuCl CuCl2 CuCl2·2H2O CuCN CuF2 Cu(OOCH)2 Cu(OH)2 CuI Cu(NO3)2·3H2O Cu(OOCC17H33)2 Cu2O CuO Cu(ClO4)2 Cu(OOCC17H35)2 CuSO4 CuSO4·5H2O NC ˆ CN NC ˆ N3

143.45 223.31 338.53 98.99 134.44 170.47 89.56 101.54 153.55 97.55 190.44 241.60 626.43 143.08 79.54 262.43 630.46 159.61 249.68 52.04 68.04

4.98 4.71020 4

488 498 65 430 d 300 2H2O, 100 473 (in N2) 770

1318

bromide chloride iodide Deuterium oxide

CNBr CNCl CNI D2 or 2H2 D2O or 2H2O

105.93 61.48 152.92 4.03 20.03

v sl s aq; s a 126 aq; s alc, acet, pyr; i bz, eth 24218 aq; v s alc; s acet 0.024 aq; s HCl 7320 aq; s alc, acet 7625 aq; v s alc; s acet 0.00026 aq; s HCl, KCN 0.075 aq; s a 12.5 aq i aq; s a i aq; s HCl, KI 1380 aq; v s alc i aq; sl s alc; s eth i aq; s HCl i aq, alc; s a 14630 aq; s eth; i bz, CCl4 i aq, alc, eth; s pyr, hot bz 14.30 aq 3220 aq; s MeOH, glyc; sl s EtOH 42020 mL aq; 230 mL alc s acetonitrile; can be handled safely only in solv v s aq, alc, eth s aq, alc, eth s aq, alc, eth sl s aq misc aq

4.14 3.38625 4 2.54 2.92 4.23 1.831 3.368 5.62 2.05 6.0 6.31514 4 2.22523 3.603 2.28416 4 2.335 g · L1 2.01520 4 1.186 0.169mp (lq) 1.105620

160 588 114.5 1236 d 1122 82.3 ca 250 805 d 5H2O, 150 27.84 detonates 51.4 6.90 146–147 252.89 3.82

d 100 1212 d d 1449

1207 d 170 O2, 1800 d 130

21.15

61.35 13.0 subl 140 248.24 101.43

i aq; v sl s a 6520 aq; sl s alc

2.14

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name

Formula

Formula weight

Disulfuryl dichloride Diphosphoric(V) acid Fluorine Fluoroboric acid Fluorosulfonic acid -d or [2H] Germane Gold (III) chloride Helium

S2O5Cl2 H4P2O7 F2 HBF4 HSO3F DSO3F or 2HSO3F GeH4

215.03 117.98 38.00 87.81 100.07 101.08 76.62

AuCl3 He

303.33 4.00

Hydrazine hydrate Hydrazinium (1) chloride (2) chloride (2) sulfate Hydrogen azide borate (1) borate(3), orthobromide

H2NNH2 H2NNH2 · H2O

32.05 50.16

H2NNH3Cl ClH3NH3Cl (H3NNH3)SO4 H2 HN3 HBO2 H3BO3 HBr

68.51 104.97 130.13 2.02 43.03 43.83 61.83 80.92

48% HBr  H2O DBr or 2HBr

81.92

bromide bromide-d

Density 1.81811 1.55425 g · L1 1.74315 1.523142 3.9 0.17840 g · L1 0.1249 (lq) 1.008320 1.03821

1.422620 1.378 0.0899 g · L1 1.126 2.486 1.43515 3.38820 g · L1 2.16066 (lq) 1.49 g · L1 3.3920 g · L1

Melting point, C

Boiling point, C

Solubility in 100 parts solvent

37.5 61 219.70 d 130 87.3 89 165.9

152.5

165.5 163 88.5

d aq, a s aq d aq viol v s aq s aq s aq sl s hot HCl

254 d 272.225 atm

subl 265 268.935

6820 aq 0.86120 mL aq

1.54 51.7

113.8 119.4

misc aq, alc misc aq, alc

92.6 198 254 259.76 80 236 171.0 86.81

d 240 d 200 d 252.76 37 d 300 66.71

v s aq v s aq; sl s alc 3.420 aq; i alc 1.9 mL aq v s aq (v expl) v sl s aq 6.430 aq 19325 aq; s alc

11 87.46

126 66.5

v s aq (constant boiling) v s aq

188.20

2.15

chloride

HCl

36.46

chloride cyanide

20.24% HCl  H2O HCN

27.06

fluoride

HF

20.01

fluoride iodide

35.35% HF  H2O HI

127.92

iodide nitrate nitrate oxide oxide-d2 perchlorate 2-water periodate(1) periodate(5) peroxide phosphate(V) (1) phosphate(V) (3) phosphide

57% HI  H2O HNO3 69% HNO3  H2O H2O D2O or 2H2O HClO4 · 2H2O HIO4 H5IO6 H2O2 HPO3 H3PO4 PH3

18.02 20.03 136.49 191.91 227.94 34.02 79.98 98.00 34.00

selenide sulfide

H2Se H2S

80.98 34.08

telluride

H2Te

129.63

H2WO4 HONH2

249.86 33.03

HONH3Cl (HONH3)2SO4

69.49 164.14

tungstate(VI) (2) Hydroxylamine Hydroxylammonium chloride sulfate

63.02

1.52620 g · L1 1.18785 (lq) 1.097 0.901 g · L1 1.267510 (lq) 0.9220 g · L1 0.95719 (lq)

114.18

85.00

7220 aq

13.24

110 25.70

v s aq (constant boiling) v s aq

83.57

19.52

v s aq

5.3720 g · L1 2.79935 (lq) 1.7015 1.5027 1.4120 1.0004 1.1045 1.6720

50.79

120 35.35

v s aq (constant boiling) 700 aq

127 83 120.5 100.00 101.43 203 d 138 d 140 151.2

v s aq (constant boiling) v s aq misc aq (constant boiling)

1.46490 2.2–2.5 1.88 1.529 g · L1 2.12424 1.1906 g · L1 6.234 g · L1 5.5 1.332 1.68020

41.59 0.00 3.82 17.8 subl 110 130 0.40 subl 42.3 133.81

d 213 87.78

misc aq v s aq (commercial 72% a) 44025 aq 113 aq misc aq; s alc, eth s aq v s aq (commercial 85% a) 2617 mL aq; s alc, eth

65.73 85.52

42 60.33

9.520 mL aq 0.33425 mL aq

49

2

d aq

H2O, 100 33.1

5822 mm

i aq; s alk, HF s aq, alc

150.5 d 170

d

8317 aq; 4.420 alc 6920 aq

2.16

TABLE 2.1 Physical Constants of Inorganic Compounds (continued)

Name

Formula

Formula weight

Density

Iodic acid

HIO3

175.91

4.6290

Iodine

I2

53.82

4.66020

bromide chloride chloride, trifluoride, pentafluoride, hepta(di-) oxide, pentaIron (II) bromide (III) bromide carbonyl, penta(II) chloride (III) chloride (III) ferrate(II), hexacyano(II) fluoride (III) fluoride (II) iodide (III) nitrate 9-water (II) oxalate 2-water (II) oxide (III) oxide (II, III) oxide (II) sulfate 7-water

IBr ICl ICl3 IF5 IF7 I2O5 Fe FeBr2 FeBr3 Fe(CO)5 FeCl2 FeCl3 Fe4[Fe(CN)6]3

206.81 162.36 233.26 221.90 259.89 333.81 55.85 215.67 295.57 195.00 126.75 162.21 859.25

4.41570 3.20 3.202 3.252 2.86 g · L1 4.79925 7.86 4.636

FeF2 FeF3 FeI2 Fe(NO3)3 · 9H2O FeC2O4 · 2H2O FeO Fe2O3 Fe3O4 FeSO4 · 7H2O

93.84 112.84 309.66 404.02 179.90 71.85 159.69 231.54 278.04

4.09 3.87 5.315 1.68421 2.28 5.7 5.24 5.1 1.89

1.49 3.1625 2.898 1.80

Melting point, C d 110 to H5IO6 113.60

Boiling point, C

Solubility in 100 parts solvent

d 195 to I2O5

31016 aq

184.24

0.02920 aq; s alc, bz, chl, CS2, CCl4, eth s aq, alc, eth d aq; s alc, eth d aq; s alc, bz, eth d aq

42 27.38 101 d 8.5 4.5 d 275 1537 691 subl 21 677 304 d

116.d 97.8

1100 subl 927 587 47 d 150–160 1377 1462 d 1597

1837

102 5.5 2872 934 103 1024 332

1093 d 100 d 3414

18713 aq i aq; s a 11720 aq s aq i aq; s alc, bz, eth 6320 aq; v s alc, acet;i eth 740 aq i aq; s HCl sl s aq; s a 0.09125 aq; s a; i alc, bz s aq 13820 0.04418 aq; s a i aq; s a i aq; s HCl i aq; s a 4820 aq

2.17

(III) sulfate (III) sulfate 9-water Krypton

Fe2(SO4)2 Fe2(SO4)3 · 9H2O Kr

399.88 562.01 83.80

Lead (II) acetate 3-water (IV) acetate (II) azide (II) carbonate (II) chromate(VI) (2) (IV) fluoride (II) nitrate (II) oleate (II) oxide (IV) oxide (II) phosphate (II) stearate (II) sulfate Lithium aluminate, tetrahydridoamide benzoate boronate bromate bromide carbonate chloride fluoride hydride hydroxide iodide iodide 3-water nitrate

Pb Pb(C2H3O2)2 · 3H2O Pb(C2H3O2)4 Pb(N3)2 PbCO3 PbCrO4 PbF4 Pb(NO3)2 Pb(C18H33O2)2 PbO PbO2 Pb3(PO4)2 Pb(C18H35O2)2 PbSO4 Li LiAlH4 LiNH2 LiC7H5O2 LiBH4 LiBrO3 LiBr Li2CO3 LiCl LiF LiH LiOH LiI LiI · 3H2O LiNO3

207.21 379.33 443.37 291.23 267.20 323.18 283.21 331.23 770.12 223.21 239.21 811.59 774.15 303.28 6.94 37.95 22.96 128.05 21.79 134.85 86.84 73.89 42.40 25.94 7.95 23.95 133.84 187.89 68.94

3.09718 2.1 3.736 g · L1 11.34 (fcc) 2.55 2.22817 6.6 6.1215 6.7 4.5320 9.53 9.375 6.9 6.2 0.53520 0.917 1.17818 0.666 3.62 3.464 2.110 2.068 2.64020 0.780 2.54 4.061 3.5 2.38

d 1178 d 175 157.2

153.4

327.50 d 200 175 expl 350 d 340 844 600 d 200

1753

886 d 752 1014 ca 125 1090 180.6 d 125 374  300 268

1516

550 720 610 846 688.7 471.2 467 73 261

d

1340 d 430 d 380 1289 d 1383 1717 d 950 1626 1178 3H2O, 300

sl s aq (hyd); sl s alc 440 aq 5.9420 mL aq i aq; s HNO3 4615 aq d aq; s chl 0.02318 aq; s HOAc i aq; s a, alk i aq; s a hyd aq 5620 aq; 1.3 MeOH i aq; s alc, bz, eth 0.001720; s HNO3 i aq; s HCl i aq; s HNO3, alk 0.0535 aq; s hot alc 0.004 aq d aq to LiOH d aq, alc; 30 eth (flammable) d aq; i bz, eth 33 aq; 7.7 alc d aq; s eth, THF 17920 aq 164 aq; s alc, eth 1.320 aq; i alc; s a 7720 aq; s alc, acet 0.1325 aq; s a d aq; no known solv (flammable) 12.420 aq 16520 aq; v s alc 200 aq; 200 alc 7020 aq; s alc

2.18

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Lithium perchlorate sulfate Magnesium amide bromide bromide 6-water carbonate chloride hydride hydroxide oleate oxide perchlorate sulfate 7-water sulfite 6-water Manganese acetate 4-water bromide 4-water carbonate (di-) carbonyl, decachloride 4-water (III) fluoride nitrate 6-water (IV) oxide sulfate hydrate

Formula

Formula weight

Density

Melting point, C

LiClO4 Li2SO4 Mg Mg(NH2)2 MgBr2 MgBr2 · 6H2O MgCO3 MgCl2 MgH2 Mg(OH)2 Mg(C18H33O2)2 MgO Mg(ClO4)2 MgSO4 · 7H2O MgSO3 · 6H2O

106.40 109.88 24.31 56.37 184.13 292.22 84.32 95.23 26.34 58.33 293.61 40.52 223.23 246.49 212.47

2.4325 2.22 1.7420 1.3925 4 3.72 2.00 2.958 2.41 1.45 2.36

236 860 650 ign in air 711 165 d d 402 714 d 287 (vac) 268 d

3.58 2.2120 1.67 1.725

2825 d 251 6H2O, 120 6H2O, 200

Mn(C2H3O2)2 · 4H2O MnBr2 · 4H2O MnCO3 Mn2(CO)10 MnCl2 · 4H2O MnF3 Mn(NO3)2 · 6H2O MnO2 MnSO4 · H2O

245.08 286.82 114.94 389.99 197.91 111.93 287.05 86.94 169.01

1.589 3.125 1.7525 2.01 3.54 1.8 5.026 2.95

54d d 155 (CO atm) 4H2O, 198 d 600 25.8 d 530 H2O, 400

Boiling point, C

d 400 1105 1158

1437 ign air

3260 7H2O, 250 d

d 110

Solubility in 100 parts solvent

5620 aq 34.520 aq i aq; s a d viol aq giving NH3 10120 aq 16020 aq; s alc 0.01 aq; s a 54.620 aq d viol aq, alc i aq; s a i aq; s alc, eth, PE i aq; s a 49.6 aq 27.2 aq; s alc 6625 aq 3850 aq; s alc 200 aq; s alc 0.006525 aq; s a i aq; s org solv 143 aq; s alc; i eth hyd aq; s a v s aq, alc i aq; s HCl 7020 aq

Mercury (II) acetate (II) bromide (I) chloride (II) chloride (II) cyanide (II) fluoride (II) iodide (II) nitrate (II) oxide (I) sulfate (II) sulfate (II) sulfide, red Molybdenum carbonyl, hexa(V) chloride (VI) oxide sulfide, diMolybdic acid hydrate Molybdic phosphoric acid Neon Nickel acetylacetonate bromide chloride 6-water dimethylglyoxime formate 2-water nitrate 6-water sulfate 6-water

Hg Hg(C2H3O2)2 HgBr2 Hg2Cl2 HgCl2 Hg(CN)2 HgF2 Hgl2 Hg(NO3)2 HgO Hg2SO4 HgSO4 HgS

200.59 318.70 360.44 472.09 271.52 252.65 238.61 454.45 324.63 216.61 497.29 296.68 232.68

13.59420 3.28 6.05 7.150 5.44 3.996 8.9515 6.28 4.3 11.14 7.56 6.47 8.10

38.86 178 241 subl 382 277 d 320 645 259 79 d 476 d d subl 583

Mo(CO)6 MoCl5 MoO3 MoS2 H2MoO4 · H2O H7[P(Mo2O7)6] · 28H2O

264.02 273.21 143.95 160.08 179.97 2365.71

1.96 2.928 4.69626 5.0615 3.12415 2.53

subl 102 194 801 2375 H2O, 70 78

156.4 264 1155 subl 450

s bz hyd aq; s conc a 0.2228 aq; s alk, NH3 i aq; s aqua regia 0.13318; s alk hyd aq

Ne Ni Ni(C5H7O2)2 NiBr2 NiCl2 · 6H2O Ni(HC2H6N2O2)2 Ni(OOCH)2 · 2H2O Ni(NO3)2 · 6H2O NiSO4 · 6H2O

20.18 58.71 256.93 218.53 237.70 288.91 184.78 290.81 262.86

0.88990 g · L1 8.90 1.45517 5.098

248.6 1455 229 963

246.1 2920 235 subl

2.15420 2.05 2.07

subl 250 2H2O, 130 56.7 53.3

d 180 136.7

1.0520 mL aq i aq; s HNO3 s aq, alc, bz, chl 13120 aq 11120 aq i aq; s abs alc, a s aq; i alc 15020 aq 4020 aq

356.60 subl  241 d 304 647 350 d

i aq; s HNO3 2510 aq; 7.515 MeOH 0.5620 aq; 2025 alc 0.00027 aq; s aqua regia 6.620 aq; 33 alc; 4 eth 9.320 aq; 8 alc; 25 MeOH hyd aq; s HF 0.00625 aq; 1 alc; 1.7 acet v s aq; s acet 0.00525 aq; s a 0.0625 aq; s HNO3 d aq; s a i aq; s aqua regia

2.19

2.20

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Niobium (V) chloride (V) fluoride (V) oxide Nitrogen

Formula

Formula weight

NbCl5 NbF5 Nb2O5 N2

270.20 187.91 265.82 28.01

[15N]

15

N2

30.01

chloride, tri(di-) oxide

NCl3 N2O

120.37 44.02

oxide

NO

30.01

N2O4 N2O5

92.02 108.01

NOCl NOF

(di-) oxide, tetra(di-) oxide, pentaNitrosyl chloride fluoride Nitryl chloride fluoride Osmium oxide, tetraOxygen

Density

Melting point, C

Boiling point, C

Solubility in 100 parts solvent

2.75 2.7080 4 4.6 1.16520 g · L1 1.2520 g · L1 1.65320 1.843320 g · L1 1.248820 g · L1 1.44720 4 2.0515

204 80 1512 210.00

250 235

209.95

195.73

27 90.85

71 88.47

i aq; s bz, CS2, CCl4 1300 mL aq; s alc

163.64

151.76

70 mL aq

9.3 30

21.10 d 47.0

d aq; s HNO3, H2SO4, chl s aq, chl

65.47 49.01

1.5925 2.78820 g · L1

61.5 132.5

5.5 59.9

hyd aq hyd aq

NO2Cl

81.46

145

13.5

d aq

NO2F

65.00

166.0

72.4

d aq

OsO4 O2

254.20 32.00

2.81100 g · L1 2.720 g · L1 4.91 1.33120 g · L1

40.6 218.75

130.0 182.96

7.2425 aq; 37525 CCl4 3625 mL aq

195.81

s HCl, CCl4 hyd aq, alc i aq; s HF, hot H2SO4 1.5220 mL aq

Ozone

O3

48.00

Palladium acetate chloride nitrate oxide Perchloryl fluoride Phosphine

Pd Pd(C2H3O2)2 PdCl2 Pd(NO3)2 PdO ClO3F PH3

106.4 224.49 177.30 230.42 122.40 102.46 34.00

Phosphinic acid Phosphonic acid Phosphoric acid metaorthocommercial 85% acid

HPH2O2 H2PHO3

66.00 82.00

HPO3 H3PO4

79.98 98.00

1.99820 g · L1 12.023 4.018 8.7020 0.637 1.529 g · L1 1.49319 1.65121

192.5

110.50

49.40 mL aq

1550 205d 680 d 870 d 147.74 133.81

2940

s hot HNO3, H2SO4 i aq, alc; s acet, chl s aq hyd aq; s HNO3 i aq, a

46.67 87.78

2617 mL aq; s alc, eth

26.5 ca 73

d 50 d 180

s aq v s aq, alc

2.2–2.5 1.88 1.685

42.35 anhyd 150

d 680

slowly hyd aq; s alc to H4P2O7 ca 200; to HPO3  300

v s aq

H2PO3F

99.99

1.818

80

P (P4 molecules)

30.97

1.828

44.2

280.3

(red) bromide, tribromide, pentachloride, trichloride, pentafluoride, penta-

P PBr3 PBr5 PCl3 PCl5 PF5

30.97 270.73 430.56 137.35 208.27 125.98

597 40.5 d 100 91 subl 100 93.8

subl 416 173.2 75 166 d 84.6

(tetra-) oxide, hexa(tetra-) oxide, deca(tetra-) selenide, tri(tetra-) sulfide, deca-

P4O4 P4O10 P4Se3 P4S10

219.90 283.88 360.80 444.54

2.34 2.8515 3.4620 1.57520 2.11920 5.805 g · L1 2.13620 4 2.30 1.31 2.09

i aq; 0.025 alc; 1 eth; 2.5 chl, bz; 1.25 CS2 i aq (ign in air 260C) d aq, alc; s acet, CS2 d aq; s CCl4, CS2 d aq, alc; s bz, chl hyd aq; s CCl4, CS2 hyd aq

24 340 245 288

175 (in N2) subl 360 360–400 514

hyd aq; s bz, CS2 d aq; s H2SO4 hyd aq; s bz, chl, acet hyd aq; s alk, CS2

fluoroPhosphorus (white)

2.21

2.22

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Phosphoryl chloride, triPlatinic(IV) acid 6-water, hexachloroPlatinum Platinum (II) chloride (IV) oxide Potassium acetate bismuthate(4—), heptaiodoborate, tetrahydridobromate bromide carbonate chlorate chloride chromate(VI) citrate hydrate cobaltate(III) 1.5-water, hexanitritocyanate cyanide dichromate(VI) disulfate(IV)

Formula

Formula weight

Melting point, C

Density

Boiling point, C

Solubility in 100 parts solvent

POCl3 H2PtCl6 · 6H2O

153.35 517.92

1.64525 2.431

2 60

105

d aq, alc v s aq, alc

Pt

195.09

21.4520

1770

3824

i aq; s aqua regia, fused alk

PtCl2 PtO2 K KC2H3O2 K4BiI7

266.00 227.09 39.10 98.14 1253.82

6.05 10.2 0.85620 1.5725

d 581 450 63.7 292

765.5

i aq; s HCl, NH4OH i aq, aqua regia d to KOH aq; s a 25620 aq; 34 alc d aq; s alk iodide soln

KBH4 KBrO3 KBr K2CO3 KClO3 KCl K2CrO4 K3C6H5O7 · H2O K3[Co(NO2)6] · 1.5H2O

53.95 167.01 119.01 138.20 122.55 74.56 194.20 324.42 479.30

1.11 3.2717 2.75 2.29 2.23820 1.988 2.73218 1.98

d 497 350 734 901 368 771 975 d 230 d 200

KOCN KCN K2Cr2O7 K2S2O5

81.11 65.12 294.19 222.32

2.048 1.5216 2.67625

d 700–900 622 398

d 370 1398 d d 368 1437

1625 d 500

2125 aq; 3.520 MeOH 6.920 aq 6520 aq; 0.4 alc 11120 aq; i alc 7.320 aq; 2 glyc 3420 aq; 7 glyc 6420 aq; i alc 16715 aq 0.08917 aq; v sl s alc s aq; sl s alc 50 aq 12.320 aq s aq (flammable if ground)

ethyldithiocarbonate ferrate(III), hexacyanofluoride formate gluconate hydride hydrogen arsenate, dihydrogen carbonate hydrogen difluoride hydrogen bisiodate hydrogen oxalate hydrogen bisoxalate dihydrate, trihydrogen phosphate hydrogen phosphate, dihydrogen phthalate hydrogen sulfate hydrogen tartrate hydroxide iodate iodide manganate(VI) nitrate nitrite oxalate hydrate periodate permanganate peroxide peroxodisulfate phenolsulfonate hydrate phosphate selenocyanate

KC2H5OCSS K3[Fe(CN)6] KF KOOCH KC6H11O7 KH KH2AsO4 KHCO3 KHF2 KH(IO3)2 KHC2O4 KH3(C2O4)2 · 2H2O

160.30 329.26 58.10 84.10 234.24 40.11 180.02 100.11 78.11 389.92 128.11 254.20

K2HPO4 KH2PO4 KHC8H4O4 KHSO4 KHC4H4O6 KOH KIO3 KI K2MnO4 KNO3 KNO2 K2C2O4 · H2O KIO4 KMnO4 K2O2 K2S2O8 KC6H4(OH)SO3 · H2O K3PO4 KSeCN

174.18 136.09 204.22 136.17 188.18 56.11 214.02 166.02 197.12 101.10 85.10 184.24 230.01 158.03 110.20 270.32 240.28 212.28 144.08

1.55822 1.89 2.481 1.91 1.43 2.867 2.17 2.37

d 200 d 858 167.5 d 180 417 d 288 d 100–200 238.7

2.044 1.836

d d

2.338 1.63625 2.24 1.956 2.044 3.8925 3.12 2.10916 1.915 2.1274 3.61815 4 2.703 2.477 1.87 2.56417

d 400 d 197 406 560 d 681 d 190 334.3 441 H2O, 160 582 d d 240 490 d 100 1340 d 100

1517 d 168

d 478

d d 1320 1345 d 400 d 250 d

v s aq 8420 aq (slow) 9520 aq 33720 aq v s aq; i alc, bz, chl d aq 196 aq; 63 gly; i alc 3420 aq 3020 aq; s alc 1.315 aq 2.5 aq 1.813 aq 150 aq 22.620 aq 10.2 aq; sl s alc 4820 aq 0.520 aq 11220 aq; 33 alc 8.120 aq; i alc 14420 aq; 4,5 alc; 1.2 acet s aq (stable in KOH) 3220 aq; 0.16 alc; s glyc 30620 aq 3620 aq 0.4220 aq 6.3420 aq d 5.320 aq s aq, alc 9220 aq s aq

2.23

2.24

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Potassium silicate(2) silicate, hexafluorosodium tartrate 4-water sorbate stannate(IV) 3-water sulfate sulfite dihydrate thiocarbonate thiocyanate thiosulfate titanate(IV), oxobis(oxalato)diaquaRhenium(VII) sulfide Rhodium(III) chloride Rubidium chloride iodide nitrate sulfate Ruthenium (III) chloride (IV) oxide Selenic acid Selenium (IV) oxide

Formula

Formula weight

Density

Melting point, C

K2SiO3 K2SiF6 KNaC4H4O6 · 4H2O KC6H7O2 K2SnO3 · 3H2O K2SO4 K2SO3 · 2H2O K2CS2 KSCN

154.29 220.25 282.23 150.22 298.94 174.27 194.30 186.41 97.18

K2S2O3 K2[TiO(C2O4)2(H2O)2]

190.33 354.18

Re2S7 RhCl3

596.85 209.28

4.866

RbCl RbI RbNO3 Rb2SO4

120.94 212.37 147.47 267.03

2.76 3.55 3.11 3.61320

715 640 310 1060

RuCl3 RuO2 H2SeO4 Se SeO2

207.47 133.07 144.98 78.96 110.96

3.11 6.97 2.950815 4 4.8120 15 3.95415

d 500 d 58 221 340

2.27 1.790 1.363 3.197 2.662

1.88614

976 d 70–80 d 270 3H2O, 140 1067 d d 173

Boiling point, C

d 220

1670

d 500

d 400

d 460 d 450

subl 850 1381 1304

260 685 subl 315

Solubility in 100 parts solvent

s aq sl s aq 5415 aq 11020 aq 10020 aq 1120 aq; 1.3 glyc; i alc 10620 aq v s aq 21720 aq; 200 acet; 8 alc acet; 8 alc 15520 aq v s aq i aq; s HNO3 i aq; s KOH, KCN 9120 aq; 1.1 MeOH 14418 aq 5320 aq 4820 aq i aq; s HCl, alc i aq; s fused alk 56720 aq (viol) s CS2, KOH, KCN 3814 aq; 1012 MeOH

(di-) sulfide, hexa(tetra-) sulfide, tetraSilane Silicon carbide chloride isothiocyanate, tetraoxide, di- (quartz) oxide-tungsten trioxide-water (1/12/26) (silicotungstic acid) telluride, triSilver acetate azide carbonate chlorate chloride chromate(VI) cyanide fluoride (II) fluoride iodate iodide nitrate nitrite oxide (II) oxide permanganate phosphate, orthosulfate

Se2S6 Se4S4 SiH4 Si SiC SiCl4 Si(NCS)4 SiO2 SiO2 · 12WO3 · 26H2O

350.28 444.08 32.09 28.09 40.07 169.89 260.40 60.08 3310.66

Si2Te3 Ag AgC2H3O2 AgN3 Ag2CO3 AgClO3 AgCl Ag2CrO4 AgCN AgF AgF2 AgIO3 AgI AgNO3 AgNO2 Ag2O AgO AgMnO4 Ag3PO4 Ag2SO4

438.97 107.87 166.92 149.89 275.77 191.34 143.34 331.77 133.90 126.88 145.87 282.80 234.80 169.89 153.89 231.76 123.88 226.81 418.62 311.83

2.44 3.20 0.68185 2.3325 3.217 1.4820 2.64–2.66

10.4915 3.25915 6.077 4.43020 5.56 5.62525 3.95 5.85216 4.57 5.52520 5.68330 4.35219 4.453 7.2225 7.48325 4.49 6.370 5.4530

121.5 113 184.7 1415 subl 2700 70 143.8 1423

892 960.15 d 252 d 220 231 455 d 320 435 690  200 558 210 d 140 d 200 d 100 d 849 660

111.9 2680 d 2972 57.6 314.2 2230

2164 297 d 270 1564

1150 d 700 d 1505 d 440

d 1085

i aq; 1.2 bz; s CS2 i aq; 0.04 bz; s CS2 d aq slowly s HF  HNO3, fused alk oxides s fused alk hyd aq; s bz, CCl4, eth d aq i aq; s HF v s aq, alc

i aq; s HNO3 1.0420 aq i aq; s KCN, HNO3 (expl) 0.00330 aq 15.320 aq 0.00019 aq; s NH4OH 0.00220 aq; s HNO3, NH4OH i aq; s KCN 17220 aq hyd viol aq 0.00420 aq i aq; s KCN 21620 aq 0.4125 aq 0.00225 aq i aq; s alk 0.9 aq; d alc 0.006 aq 0.8020 aq

2.25

2.26

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Sodium acetate aluminate, tetrachloroamide aurate(III) dihydrate, tetrachloroazide benzoate bismuthate(V)(1) boranate borate, tetraborate, tetrafluorobromate bromide carbonate carbonate 10-water chlorate chloride chlorite chromate(VI) citrate 2-water cobaltate(III), hexanitritocyanate cyanide cyanoborohydride dichromate(VI) 2-water diethyldithiocarbamate

Formula

Formula weight

Na NaC2H3O2 NaAlCl4 NaNH2 NaAuCl4 · 2H2O

22.99 82.04 191.80 39.02 397.80

NaN3 NaC6H5O2 NaBiO3 NaBH4 Na2B4O7 NaBF4 NaBrO3 NaBr Na2CO3 Na2CO3 · 10H2O NaClO3 NaCl NaClO2 Na2CrO4 Na3C6H5O7 · 2H2O Na3[Co(NO2)6] NaOCN NaCN NaBH3CN Na2Cr2O7 · 2H2O NaS2CN(C2H5)2

65.01 144.11 280.00 37.84 201.27 109.82 150.91 102.91 106.00 286.14 106.45 58.45 90.45 161.97 294.10 403.98 65.01 49.02 62.84 298.00 225.31

Melting point, C

Density 0.96820 1.528

1.6

97.82 324 151 210 d 100

1.84620

d

1.074 2.367 2.4720 3.33917 3.20518 2.533 1.46 2.489 2.16420 2.723

1.89320 2.34825 4

d 497 d 742.5 384 380 d 747 850.0 34 248 801 d 180–200 792 2H2O, 150 550 562 d 242 356 anhyd 94 anhyd

Boiling point, C 881.4

subl 400

d 1447 d d 350 1465

1530 d 400

Solubility in 100 parts solvent d aq to NaOH 46.520 aq s aq d viol aq 16620 aq 4120 aq; 0.3 alc 6325 aq; 1.3 alc i aq; d a 5525 aq; 4 alc; 1.4 pyr; 5 DMF 2.6 20 aq 10827 aq 3620 aq 9020 aq; 6 alc; 16 MeOH 21.520; s glyc 50 aq; s glyc 9620 aq; 0.77 alc; 25 glyc 3620 aq; 10 glyc 3417 aq 8420 7725 aq v s aq s aq d; 0.220 alc 58.720 aq (flammable solid) 20820 aq s aq, alc

dimethylarsonate 3-water diphosphate(V) dithionate 2-water dithionate(III) (hydrosulfite) dodecylsulfate (laurate) ethoxide ethylenebis (aminodiacetate) (EDTA) ethylsulfate ferrate(II) 10-water, hexacyanoferrate(III) 2-water, pentacyanonitrosyl(nitroprusside) fluoride formate gluconate glycerophosphate hydride hydrogen carbonate hydrogen phosphate hydrate, dihydrogen phosphate 7-water hydrogen sulfate hydrogen sulfite hydrogen sulfide 2-water hydroxide

NaO2As(CH3)2 · 3H2O Na4P2O7 Na2S2O6 · 2H2O Na2S2O4

214.03 265.90 242.13 174.13

NaO3SOC12H25 NaOC2H5 Na4C2H4N2(C2H3O2)4

288.38 68.06 380.20

NaO3SOC2H5 Na4[Fe(CN)6] · 10H2O

148.11 484.07

1.458

Na2[Fe(CN)5NO] · 2H2O

297.65

1.72

NaF NaOOCH NaC6H11O7 Na2C3H5(OH)2PO4 NaH NaHCO3 NaH2PO4 · H2O

41.99 68.02 218.13 216.03 24.00 84.01 137.99

2.78 1.919

996 253 d

1.396 2.20 2.040

d 130 d 425 CO2, 270 H2O, 100

Na2HPO4 · H2O

268.07

1.679

d

NaHSO4 NaHSO3 NaHS · 2H2O NaOH

120.07 104.06 92.09 40.01

2.435 1.48

315 d 55 322

2.27

hydroxymethanesulfinate NaO2SCH2OH · 2H2O dihydrate hypochlorite NaClO

154.12 74.44

2.45 2.189

60 988 2H2O, 110 d

3H2O, 120 d 267

10 aq d aq; s abs alc 103 aq

 300

2.13025

10H2O, 82

200 aq; 40 alc 2.260 aq 6.0520 aq 2220 aq

d 435

18.820 aq 4016 aq

63–64

1787

d 200

420 aq; i alc 8120 aq; s glyc; sl s alc 5925 aq; sl s alc; i eth 60 aq; i alc d viol aq, alc 9.620 aq; i alc 710 aq 18540 aq

d d 1557

28.525 aq; d alc 29 aq; 1.4 alc s aq, alc, eth 10820 aq; 14 abs alc; 24 MeOH; s glyc v s aq; i abs alc, bz, eth 5320 aq (anhyd v expl)

2.28

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Sodium iodate iodite lactate methoxide molybdate dihydrate nitrate nitrite oxalate oxide perchlorate periodate peroxide peroxoborate 4-water peroxodisulfate(VI) phosphate 12-water platinate(IV) 6-water, hexachloropropionate salicylate selenate(VI) silicate, hexafluorostannate(IV) 3-water stearate sulfate sulfate 10-water

Formula

Formula weight

NaIO3 NaI NaOOCCHOHCH3 NaOCH3 Na2MoO4 · 2H2O NaNO3 NaNO2 Na2C2O4 Na2O NaClO4 NaIO4 Na2O2 NaBO3 · 4H2O Na2S2O8 Na3PO4 · 12H2O Na2PtCl6 · 6H2O

197.90 149.92 112.07 54.03 241.95 85.01 69.00 134.01 61.98 122.44 213.91 77.99 153.88 238.13 380.12 561.88

NaOOCCH2CH3 NaC7H5O3 Na2SeO4 Na2SiF6 Na2SnO3 · 3H2O NaOOCC17H35 Na2SO4 Na2SO4 · 10H2O

96.07 160.11 188.94 188.05 266.71 306.47 142.06 322.19

Density

4.27720 3.6670

3.28 2.257 2.1680 2.27 2.27 2.499 3.86516 4 2.805

1.62 2.50

3.098 2.679

2.664 1.464

Melting point, C

d 660 d  300 687 308 271 1132 468 d 300 675 d 60 d 73.4 6H2O, 110

red heat d 140 d 884 32.4

Boiling point, C

1304 2H2O, 100 d 380 d 320 d 1950

d 11H2O, 100

10H2O, 100

Solubility in 100 parts solvent

8.120 aq 17820 misc aq, alc d aq; s alc 6520 aq 8820 aq 8120 aq 3.420 aq d aq to NaOH 20120 10.320 aq v s aq (d) 2.5 aq 55 aq 28.315 aq v s aq; s alc 10025 aq; 4.125 alc 9520 aq; 11 alc; 25 glyc 2720 aq 0.440 aq; i alc 500 aq sl s aq 19.520 3615 aq

sulfide sulfite tartrate dihydrate tetraphenylborate thiocyanate thiosulfate thiosulfate 5-water tungstate(VI) dihydrate Strontium carbonate chloride chromate(VI) hydroxide Sulfamic acid Sulfinyl bromide chloride fluoride Sulfonyl chloride fluoride

1.85614 4 2.63315 1.818

15.720 aq 2620 aq 296 aq s aq, acet 13420 aq s aq; i alc 7020 aq (d slowly) 880

Na2S Na2SO3 Na2C4H4O6 · 2H2O NaB(C6H5)4 NaSCN Na2S2O3 Na2S2O3 · 5H2O Na2WO4 · 2H2O

78.05 126.06 230.08 342.24 81.07 158.11 248.18 329.86

2.345 1.685 3.245

SrCO3 SrCl2 SrCrO4 Sr(OH)2 H2NSO3H

147.64 158.52 203.64 121.64 97.09

3.70 3.052 3.89515 3.625 2.126

CO2, 1172 874 375 (in H2) d 200

H2O, 710

SOBr2 SOCl2 SOF2

207.88 118.98 86.06

2.67 1.65615 3.044

49.5 104.5 110

139.7 75.8 43.8

d aq hyd aq d aq; s bz, chl, eth

SO2Cl2 SO2F2

134.98 102.07

1.667420 3.72 g · L1

46 135.8

69.3 55.38

(di-) chloride, difluoride, tetrafluoride, hexa-

S S8 S2Cl2 SF4 SF6

32.07 256.51 135.03 108.07 146.07

106.8 115.21 80 121 50.8

444.60 444.60 138.1 38 subl 63.8

oxide, di

SO2

64.07

75.47

10.01

393720 mL aq; 25 mL alc

oxide, tri(III)

SO3

80.07

1.92 1.9620 1.68815 15 1.91973 50 1.88 g · L1 2.71620 g · L1 1.4610 (lq) 1.922520

d aq; s bz 4 mL aq; 24 mL alc; 136 mL CCl4; 210 mL toluene i aq; 230 CS2; s alc, bz i aq; 230 CS2; s alc, bz hyd aq d viol aq; s bz sl s aq; s alc, KOH

16.86

43.4

slowly v s aq

Sulfur

950 d 2H2O, 120 287 5H2O, 100 2H2O, 100

2058

0.00125 aq; s a 52.920 aq 0.0920 aq; s HCl 1.7720 aq 14.7 aq

2.29

2.30

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Sulfuric acid chlorofluoroTantalum (V) fluoride Tellurium Thallium (III) acetate sesquihydrate (I) bromide (I)chloride (I) ethoxide (I) fluoride (I) nitrate (III) nitrate 3-water (I) oxide (III) oxide (I) sulfate Thiocarbonyl chloride Thiocyanogen Thionyl, see Sulfinyl Tin (silver-white, tetr) (gray, cub) (IV) bromide (II) chloride

Formula

Formula weight

Density

Melting point, C

Boiling point, C

Solubility in 100 parts solvent

H2SO4 HOSO2Cl FSO2OH Ta TaF5 Te Tl Tl(C2H3O2)3 · 1.5H2O

98.08 116.52 100.07 180.95 275.95 127.60 204.37 408.53

1.831820 1.75320 1.72625 16.69 4.7420 6.2420 11.85

10.38 80 88.98 2985 95–97 450 303.5 182 d

335.5 152 162.6 5513 229 1009 1487

v s aq d viol aq d viol aq i aq; s HF, fused alk s aq i aq; s HNO3, KOH i aq; s HNO3

TlBr TlCl TlOC2H5 TlF TlNO3 Tl(NO3)3 · 3H2O Tl2O Tl2O3

284.31 239.85 249.43 223.39 266.40 444.43 424.78 456.78

7.54 7.00430 3.49320 8.234 5.556

460 429 3 322 206 102–103 300 717

825 816 d 130 700 430

0.0520 aq; s alc 0.3320 aq sl s alc; s eth 7815 aq 9.620 aq s aq v s aq (d); s a i aq; s a

Tl2SO4 CSCl2 (SCN)2

504.85 114.98 116.16

632

d 73.5

4.920 aq d aq; s eth d aq; s alc, CS2, eth

Sn

118.69

7.28 5.75

2623

i aq; s HCl, H2SO4

SnBr4 SnCl2

438.36 189.61

3.3533 3.95

207 652

hyd aq; s acet 840 aq; s alc, eth

9.5216 10.1922 (hex) 6.77 1.50915

1080 O2, 875

ca 2 231.89 stable 161 to 13.2 30 247

(IV) chloride (II) diphosphate(V) (II) fluoride (IV) fluoride (IV) oxide (II) sulfide (IV) sulfide (II) zirconate (IV), hexafluoroTitanium (III) chloride

SnCl4 Sn2P2O7 SnF2 SnF4 SnO2 SnS SnS2 SnZrF6

260.53 411.32 156.70 194.70 150.70 150.77 182.83 323.92

2.226 4.00916 4.5725 4.78019 6.95 5.08 4.5 4.21

Ti TiCl3

47.90 154.27

4.507 2.71

(IV) chloride hydride, di (IV) isopropoxide (IV) oxide (rutile) (III) sulfate Trisulfuryl dichloride Tungsten (VI) chloride (VI) oxide sulfide, diUranyl (VI) acetate 2-water nitrate 6-water Vanadium (III) oxide (V) oxide (IV) oxide sulfate Xenon

TiCl4 TiH2 Ti[OCH(CH3)2]4 TiO2 Ti2(SO4)3 ClSO2OSO2OSO2Cl

189.73 49.92 284.26 79.90 384.00 295.09

WCl6 WO3 WS2

fluoride, di-

34 213 subl 705 1630 881 765

115

subl 1900 1210

s aq, eth i aq; s conc a 30 aq hyd aq i aq i aq; s conc HCl i aq; d by aqua regia s aq

3318 d 5000

s hot a, HF s aq, alc

1.726 3.752 0.971120 4.23

1660 subl 831 (vac) 24.10 d 400 ca 20 1857

136.4

s cold aq, alc

1.9020

18.7

613 mm

396.57 231.86 247.98

2.721282 7.16 7.510

281.5 1472 d 1250

340.5 1837

hyd aq; s CS2, CCl4 i aq; s hot alk s HNO3  HF

UO2(C2H3O2)2 · 2H2O UO2(NO3)2 · 6H2O

422.13 502.13

2.89315 2.80713

2H2O, 110 60.2

d 275 d 100

7.715 aq 15520 aq

V2O3 V2O5 VOSO4 Xe

149.00 181.90 163.00 131.30

4.87 3.35

2067 670

1690

111.8

108.10

XeF2

169.30

5.89710 g · L1 3.1325

i aq; s HNO3  HF 0.80 aq; s a, alk v s aq 10.820 mL aq

129.0

subl 114

2.50 aq

22010 mm s HF s HCl

2.31

2.32

TABLE 2.1 Physical Constants of Inorganic Compounds (continued )

Name Xenon fluoride, tetrafluoride, hexaZinc acetate dihydrate bromide carbonate chloride chromate(VI) cyanide fluoride iodide nitrate 6-water oxide peroxide p-phenolsulfonate 8-water phosphate(V) phosphide propionate silicate 6-water, hexafluorostearate sulfate sulfate 7-water sulfide thiocyanate

Formula

Formula weight

XeF4 XeF6 Zn Zn(C2H3O2)2 · 2H2O ZnBr2 ZnCO3 ZnCl2 ZnCrO4 Zn(CN)2 ZnF2 ZnI2 Zn(NO3)2 · 6H2O ZnO ZnO2 Zn[C6H4(OH)SO3]2 · 8H2O Zn2(PO4)2 Zn3P2

207.30 245.30 65.37 219.49 225.21 125.38 136.29 181.36 117.42 103.38 319.22 297.47 81.37 97.38 555.83 386.05 258.09

Zn(OOCCH2CH3)2 ZnSiF6 · 6H2O

211.52 315.54

Zn(OOCC17H35)2 ZnSO4 ZnSO4 · 7H2O ZnS Zn(SCN)2

632.33 161.44 287.54 97.43 181.53

Density

3.0325 3.41125 7.1425 1.735 4.22 4.398 2.90725 3.40 1.852 5.0025 4.73625 2.06514 5.67 3.00

Melting point, C

117.1 49.5 419.6 237 402 CO2, 300 318

3.99815 4.55

d 800 872 446 36.4 1970 d 150 8H2O, 120 900  420

2.104

d 100

3.54 1.957 4.087

ca 120 1200 7H2O, 280 1722

Boiling point, C

subl 116 75.6 911 650 732

1500 730 6H2O, 131

subl 1100 (in H2)

Solubility in 100 parts solvent

hyd aq; s F3CCOOH hyd aq i aq; s a, alk 41.620 aq; 3.3 alc 44620 aq; 200 alc; s eth 0.0225 aq; s a, alk 39520 aq; 77 alc; 50 glyc i aq; s a 0.05818 aq; s KCN, alk 1.620 aq 43220 aq; 50 glyc 1460 aq i aq; s a, alk i aq; d slowly 63 aq; 56 alc i aq; s a, NH4OH d aq; s bz, CS2; d viol HCl 32 aq; 2.8 alc v s aq

d 500

i aq, alc, eth; s bz 53.820 aq 9620 aq; 40 glyc; i alc i aq; s a 0.1418 aq; s alc

Zirconium (IV) chloride chloride oxide 8-water hydroxide (IV) oxide silicate(4) sulfate 4-water

Zr ZrCl4 ZrCl2O · 8H2O Zr(OH)4 ZrO2 ZrSiO4 Zr(SO4)2 · 4H2O

91.22 233.05 322.25 159.25 123.22 183.31 355.41

6.5230 2.80315 1.91 3.25 5.85 4.56 3.2216

1852 437 8H2O, 210 2H2O, 500 2677 d 1538 anhyd 380

4504 subl 334

4275

s aqua regia hyd aq; s alc, eth s aq sa s hot H2SO4, HF slowly very inert 52.518 aq

2.33

SECTION 3

PROPERTIES OF ATOMS, RADICALS, AND BONDS

NUCLIDES . . . . . . . . . . . . . . . . . . . . . . . . . Table 3.1 Table of Nuclides . . . . . . . . . . . . . ELECTRONEGATIVITY . . . . . . . . . . . . . . . . . . Table 3.2A Electronegativities of the Elements . . . Table 3.2B Electronegativities of the Groups . . . . ELECTRON AFFINITY . . . . . . . . . . . . . . . . . . . Table 3.3 Electron Affinities of Elements, Radicals, and Molecules . . . . . . . . . . . . . . BOND LENGTHS AND STRENGTHS . . . . . . . . . . Table 3.4A Bond Lengths between Carbon and Other Elements . . . . . . . . . . . . . . Table 3.4B Bond Lengths between Elements Other than Carbon . . . . . . . . . . . . . . . . Table 3.5 Bond Strengths . . . . . . . . . . . . . . BOND AND GROUP DIPOLE MOMENTS . . . . . . . . Table 3.6 Bond Dipole Moments . . . . . . . . . . Table 3.7 Group Dipole Moments . . . . . . . . .

3.1

. . . . . .

. . . . . .

. . . . . .

3.2 3.2 3.9 3.10 3.10 3.11

. . . . . . . . . . . . . .

3.11 3.13

. . . . . . .

3.14

. . . . .

3.17 3.19 3.30 3.30 3.31

. . . . .

. . . . . .

. . . . .

. . . . . .

. . . . .

. . . . . .

. . . . .

. . . . . .

. . . . .

. . . . .

3.2

SECTION 3

NUCLIDES TABLE 3.1 Table of Nuclides Explanation of column headings Nuclide. Each nuclide is identified by its atomic number Z, equal to the number of protons in the nucleus; the corresponding symbol for that element; and the mass number A, equal to the sum of the numbers of protons Z and neutrons N in the nucleus. Thus, A  Z  N, or N  A  Z. The m following the mass number (e.g., 69 mZn) indicates an isomer of that nuclide. Half-Life. For the radioactive nuclides this time period corresponds to that during which loss by disintegration of 50% of the nuclide occurs. The units of time are designated by year (yr), day (d), hour (h), minute (min), and second (s). Natural Abundance. The isotopic abundances listed are on an “atom percent” basis for the stable nuclides present in naturally occurring elements in the earth’s crust. Thermal Neutron Absorption Cross Section. The ease with which a given nuclide can absorb a thermal neutron 1 (energy 40 eV) and become of a different nuclide is indicated by the cross section, given here in units of barns (1 barn  1024 cm2). If the mode of reaction is other than (n, ), it is so indicated, for example, (n, p) or (n, ), where n  neutron, p  proton,   gamma ray, and   alpha particle (42He). Major Radiations. In this column are listed the principal mode(s) of decay and the energies of the emanating radiations in million electronvolts (MeV). The gamma-ray () intensities, where given, are given to the nearest whole percentage in parentheses following the numerical energy value for that particular . In most cases the radiations listed should be sufficient for identification of the particular nuclide. The following designations are used: negatron (), positron (), conversion electron (e), gamma ray (), and alpha particle ().

Nuclide Symbol 1

Mass

H H 3 H 6 Li 7 Li 7 Be 9 Be 10 Be 10 B 11 B 11 C 13 C 14 C 13 N 14 N 19 O

1.007 825 2.014 102 3.016 050 6.015 125 7.016 004 7.016 929 9.012 186 10.013 534 10.012 939 11.009 305 11.011 432 13.003 354 14.003 242 13.005 738 14.003 074 19.003 578

18

18.000 937 21.994 437

2

F Na

22

Half-life

Natural abundance, %

Thermal neutron absorption cross section, barns

99.985 0.015

0.332 0.000 5

7.42 92.58 100

953(n, ) 0.037 54,000(n, p) 0.009

19.7 80.3

3837(n, ) 0.005

1.108

0.000 9

12.26 yr

53.6 d 2.5  106 yr

, 0.477(10) , 0.555; no 

, 0.156; no  , 1.20; , 0.511

5730 yr 9.96 min 99.635

109.7 min 2.62 yr

, 0.018 6; no 

, 0.97; , 0.511

20.34 min

29.1 s

Major radiations

1.81(n, p) , 4.60; , 0.197(97), 1.37(59) , 1.74; , 0.511 , 1.820, 0.545; , 0.511, 1.275(100)

3.3

PROPERTIES OF ATOMS, RADICALS, AND BONDS

TABLE 3.1 Table of Nuclides (continued)

Nuclide Symbol 23

Mass

Half-life

Na Na

22.934 473 23.990 962

14.96 h

Mg Mg

24.985 839 27.983 875

21.2 h

26

Al

25.986 891

7.4  105 yr

27

Al Al

26.981 539 27.981 905

2.31 min

Si Si 31 P 32 P 33 P 34 S 35 S 38 S

29.973 763 30.975 349 30.973 765 31.973 909 32.971 728 33.967 865 34.969 031 37.971 230

35

Cl Cl 37 Cl 38 Cl 39 Cl

34.968 851 35.968 309 36.965 898 37.968 005 38.968 008

37.29 min 55.5 min

37

Ar K

32.966 772 39.964 000

35.1 d 1.26  109 yr

K K

40.961 832 41.962 406

12.36 h

Ca Ca 47 Ca

43.955 490 44.956 189 46.954 538

165 d 4.535 d

46

45.955 919

83.9 d

24

25 28

28

30 31

36

40

41 42

44 45

Sc

Natural abundance, %

Thermal neutron absorption cross section, barns

100

0.53

Major radiations

, 4.17, 1.389; , 0.511, 1.275(100) 10.11

0.3 , 0.46; e, 0.03; , 0.031(96), 0.40(30), 0.95(30), 1.35(70) , 8.5; , 0.511, 1.12(4), 1.81(100)

100

0.235 , 2.85; , 1.780 (100)

3.12

0.11

100

0.19

, 1.48; , 1.26

2.62 h

, 1.710 , 0.248; no 

14.28 d 24.4 d 4.22

0.27 , 0.167; no  , 3.0, 1.1; , 1.88(95)

87.9 d 2.87 h 75.53 3.08  105 yr 24.47

44 100 0.4

0.118

70

6.77

1.2

, 0.714; , 0.511 , 4.91; , 1.60(38) , 3.45, 2.18, 1.91; , 0.246(44) Cl X rays , 1.314; , 0.483; , 1.460(11) , 3.52; , 0.31, 1.524(18)

2.06

0.7 , 0.252 , 1.98, 0.67; , 0.49(5), 0.815(5), 1.308(74) , 1.48, 0.357, , 0.889(100), 1.120(100)

3.4

SECTION 3

TABLE 3.1 Table of Nuclides (continued)

Nuclide Symbol

Mass

Half-life

44

43.959 572

48 yr

48

47.952 259

16.0 d

49

V Cr 51 Cr 54 Mn

48.949 522 49.946 054 50.944 768 53.940 362

330 d 27.8 d 303 d

55

54.938 050 55.938 910

2.576 h

Ti

V

50

Mn Mn

56

54

57

56.936 296

270 d

58

57.935 761

71.3 d

59

58.933 189 59.933 813

5.263 yr

Co

Co

Co Co

60

62

Ni Ni 64 Ni 65 Ni

61.928 342 62.929 664 63.927 958 64.930 072

63

62.929 592 63.929 759

63

Cu Cu

64

17 , 0.320(9); e, 0.315 , 0.835(100); e, 0.829

100

53.939 617 54.938 299 57.933 282 58.934 878

13.3 , 2.85; , 0.847(99), 1.811(29), 2.110(15)

5.84

2.9

0.31

1.1

2.60 yr

Mn X rays , 1.57, 0.475; , 0.143(1), 0.192(3), 1.095(56), 1.292(44) , 0.014(9), 0.122(87), 0.136(11), 0.692; e, 0.115, 0.129 , 0.474; , 0.511, 0.810(99), 0.865(1), 1.67(1)

45.6 d

100

19 6

3.66

15

1.16

1.5

, 1.48, 0.314; , 1.173(100), 1.332(100) , 0.067; no 

92 yr

, 2.13; , 0.368(5), 1.115(16), 1.481(25)

2.564 h 69.1 12.80 h

Major radiations , 0.068(90), 0.078(98); e, 0.065, 0.073 , 0.696; , 0.511, 0.945(10), 0.983(100), 1.312(97), 2.241(3) Ti X rays

4.31

Fe Fe 58 Fe 59 Fe 55

Natural abundance, %

Thermal neutron absorption cross section, barns

4.5 , 0.573; , 0.656; e, 1.33; , 0.511, 1.34(1)

3.5

PROPERTIES OF ATOMS, RADICALS, AND BONDS

TABLE 3.1 Table of Nuclides (continued)

Nuclide Symbol 64 65

68

Mass

Half-life

Zn Zn

63.929 145 64.929 234

 8  1015 yr 245 d

Zn Zn

67.924 857

69 m

71

11.4 d

77

As

76.920 645

38.7 h

75

Se

74.922 525

120.4 d

79

Br Br

78.918 329 79.918 536

17.6 min

Br Br

80.916 292 81.916 802

35.34 h

Kr Rb 85 Sr

84.912 523 85.911 193 84.912 989

10.76 yr 18.66 d 64.0 d

90

89.907 163 94.906 832

64.0 h 35.0 d

81 82

85 86

95

Y Nb

0.46

Major radiations

, 0.327; e, 1.106; , 0.511, 1.115(49) 18.56

70.924 956 74.921 595 75.922 397

80

48.89

1.0 , 0.439(95); e, 0.429 Ga X rays

13.8 h

Ge As 76 As 75

Natural abundance, %

Thermal neutron absorption cross section, barns

100

4.5 , 2.97; , 0.559(43), 0.657(6), 1.22(5) 1.44(1), 1.789, 2.10(1) , 0.68; , 0.086, 0.239(3), 0.522(1) , 0.066(1), 0.097(1), 0.121(17), 0.136(57), 0.265(60), 0.280(25), 0.401(12); e 0.085, 0.095, 0.109, 0.124, 0.253

26.4 h

50.52

8.5 , 2.00; , 0.87; , 0.511, 0.618(7), 0.666(1)

49.48

3

 15

~7

, 0.444; , 0.554(66), 0.619(41), 0.698(27), 0.777(83), 0.828(25), 1.044(29), 1.317(26), 1.475(17) , 0.67; , 0.514 , 1.78; , 1.078(9) , 0.514(100); e, 0.499 , 2.27; no  , 0.160; , 0.765(100)

3.6

SECTION 3

TABLE 3.1 Table of Nuclides (continued)

Nuclide Symbol 99

Mo

Mass

Half-life

98.907 720

66.7 h

Tc Ru

102.906 306

6.049 h 39.5 d

Pd Pd

107.903 891 108.905 954

13.47 h

Ag Ag 111 Ag

108.904 756 110.905 316

39.2 s 7.5 d

109

108.904 928 114.905 431

453 d 53.5 h

99 m 103

108 109

109

110 m

115

Cd Cd

113 m

In

114

Sn Sb 122 Sb

112.905 187 120.903 816 121.905 183

115 d

123

Sb Sb

122.904 213 123.905 973

1.3  1016 yr 60.4 d

Sb

124.905 232

2.71 yr

124

125

89 , 0.088(5) , 1.05; , 0.247(1), 0.342(6) , 0.088; e, 0.062 , 1.11; , 0.230(1), 0.262(2), 0.49(10), 0.53(26) , 0.393(64); e, 0.365, 0.389 , 1.988; , 0.42; , 1.299 , 0.255(2)

99.8 min

72 s

121

12 , 1.028; , 0.088(5), 0.129, 0.31, 0.41, 0.60, 0.64

48.65

113.904 905

Major radiations , 1.23; , 0.041(12), 0.181(7), 0.372(1), 0.740(12), 0.780(4) , 0.140(90); e, 0.110 , 0.70, 0.21; , 0.497(88), 0.610(6)

26.7

In

113

Natural abundance, %

Thermal neutron absorption cross section, barns

57.25

6 , 1.97; , 0.56; , 0.584(66), 0.686(3), 1.14(1) 1.26(1)

2.80 d

42.75

3.3 2000

 20

, 2.31; , 0.603(97), 0.644(7), 0.72(14), 0.967(2), 1.048(2), 1.31(3), 1.37(5), 1.45(2), 1.692(50), 2.088(7) , 0.61; e, 0.114, 0.395; , 0.176(6), 0.427(31), 0.463(10), 0.599(24), 0.634(11), 0.66(3)

3.7

PROPERTIES OF ATOMS, RADICALS, AND BONDS

TABLE 3.1 Table of Nuclides (continued)

Nuclide Symbol

Mass

Half-life

Natural abundance, %

Thermal neutron absorption cross section, barns

132

Te

131.908 523

77.7 h

125

I

124.904 578

60.2 d

127

I I

126.904 470 127.905 838

24.99 min

131

I

130.906 127

8.05 d

132

I

131.907 981

2.26 h

133

Xe

132.905 815

5.270 d

190

131

Cs Cs

130.905 466 133.906 823

9.70 d 2.046 yr

136

137

Cs

136.906 770

30.0 yr

0.11

131

Ba

130.906 716

12.0 d

133

Ba

132.905 879

7.2 yr

128

134

9 100

Major radiations , 0.22; e, 0.197; , 0.053(17), 0.230(90) , 0.035(7); e, 0.030

6.4

~0.7

, 2.12; , 0.441(14), 0.528(1), 0.743, 0.969 , 0.806, 0.606; e, 0.330; , 0.080(3), 0.284(5), 0.364(82), 0.637(7), 0.723(2) , 2.12; , 0.24(1), 0.52(20), 0.67(44), 0.773(89), 0.955(22) 1.14(6), 1.28(7), 1.40(14), 1.45(1), 1.91(1), 1.99(1) , 0.346; e, 0.045, 0.075; , 0.081(37) Xe X rays , 0.662; , 0.57(23), 0.605(98), 0.796(99), 1.038(1), 1.168(2), 1.365(3) , 1.176, 0.514; e, 0.624, 0.656; , 0.662(85) , 0.124(28), 0.216(19), 0.25(5), 0.373(13), 0.496(48), 0.60(3); e, 0.118, 0.180, 0.460 , 0.080(36), 0.276(7), 0.302(14), 0.356(69), 0.382(8); e, 0.266, 0.319

3.8

SECTION 3

TABLE 3.1 Table of Nuclides (continued)

Nuclide Symbol

Mass

137m

Ba

Half-life

Natural abundance, %

Thermal neutron absorption cross section, barns

2.554 min

140

Ba

139.910 565

12.80 d

 20

141

Ce

140.908 219

32.5 d

30

144

Ce

143.913 591

284 d

1.0

197

Au Au

196.966 541 197.968 231

2.697 d

98.8 26,000

199

Au

198.968 773

3.15 d

~30

197

Hg

196.967 360

65 h

203

Hg

202.972 880

46.9 d

Tl Tl 210 Pb

202.972 353 203.973 865 209.984 187

3.81 yr 20.4 yr

207

Bi

206.978 438

30.2 yr

210

Po Ra

209.982 876 226.025 360

138.40 d 1602 yr

 0.03 20

Am

241.056 714

433 yr

700

198

203 205

226

241

100

29.50

Major radiations , 0.662(89); e, 0.624, 0.656 , 1.02; , 0.030(11), 0.163(6), 0.305(6), 0.438(5), 0.537(34) , 0.581; e, 0.104, 0.139; , 0.145(48) , 0.31; , 0.080(2), 0.134(11) , 0.962; e, 0.329, 0.398; , 0.412(95), 0.676(1), 1.088 , 0.46, 0.30; , 0.158(37), 0.208(8); e, 0.125, 0.145 , 0.77(18), 0.191(2), 0.268 , 0.214; e, 0.194, 0.264, 0.275; , 0.279(77)

11 , 0.766 , 0.061; , 0.047(4); , 3.72 , 0.570(98), 1.063(77), 1.771(9); e 0.482, 0.975, 1.048 , 5.305; , 0.803 , 4.78, 4.60; , 0.186(4), 0.26, 0.42, 0.61; e, 0.170 , 5.49, 5.44; , 0.060(36), 0.101, 0.208, 0.335, 0.37, 0.663, 0.722

PROPERTIES OF ATOMS, RADICALS, AND BONDS

3.9

ELECTRONEGATIVITY According to Pauling, electronegativity  is the relative attraction of an atom for the valence electrons in a covalent bond. It is proportional to the effective nuclear charge and inversely proportional to the covalent radius. 

0.31(n  1  c)  0.50 r

where n is the number of valence electrons, c is any formal valence charge on the atom and the sign before it corresponds to the sign of this charge, and r is the covalent radius. Because electronegativity is concerned with atoms in molecules rather than atoms in isolation, it is not possible to define precise electronegativity values. Pauling determined his set of values from bond energy data based on experimentally measured heats of dissociation and formation. Originally the element fluorine, whose atoms have the greatest attraction for electrons, was given an arbitrary electronegativity of 4.0. A revision of Pauling’s values based on newer heat data assigns 3.9 to fluorine. A unit positive charge changes the  value for an atom by about two-thirds of the electronegativity difference between it and the atom next on its right in the Periodic Table, and a unit negative charge similarly decreases the  value. The greater the difference in electronegativity, the greater is the ionic character of the bond. The amount of ionic character I is given by the expression I  1  e0.25(

A

 B)2

The bond is fully covalent when ( A  B)  0.5 (and I  6%). A different expression was proposed by Hannay-Smyth.* I  0.46|A  B|  0.035(A  B)2 Other sets of electronegativities of the elements have been proposed. The rather direct, but somewhat limited, method of Mulliken makes use of the ionization potential IP and electron-affinity data (Table 3.3). Numerical values are obtained that coincide with values from other methods if electronegativities are calculated from IP  A 5.6 Electronegativities on the Allred-Rochow scale† are given by 

  0.359

Zeff r2

 0.744

where Zeff is the effective nuclear charge and r is the atomic radius. Using Pauling’s values, electronegativities of the elements are arranged in periodic order in Table 3.2A.

* Hannay-Smyth, J. Am. Chem. Soc., 68: 171 (1946). † J. Inorg. Nucl, Chem., 5: 264, 269 (1958).

3.10

SECTION 3

TABLE 3.2A Electronegativities of the Elements H 2.2 Li 1.0

Be 1.5

B 2.0

C 2.5

N 3.0

O 3.5

F 4.0

Na 0.9

Mg 1.2

Al 1.5

Si 1.8

P 2.1

S 2.4

Cl 2.8

K 0.9

Ca 1.0

Sc 1.3

Ti–V 1.6

Cr–Mn 1.6

Fe–Ni 1.8

Cu 1.9

Zn 1.7

Ga 1.6

Ge 1.8

As 2.0

Se 2.4

Br 2.7

Rb 0.8

Sr 1.0

Y 1.2

Zr–Nb 1.6

Mo–Tc 1.8

Ru–Pd 2.2

Ag 1.9

Cd 1.5

In 1.7

Sn 1.8

Sb 1.9

Te 2.1

I 2.2

Cs

Ba

La–Lu

Hf–Ta

W–Re

Os–Pt

Au

Hg

T1

Pb

Bi

0.7

0.9

1.1

1.3

1.8

2.2

2.4

1.4

1.8

1.8

1.9

TABLE 3.2B Electronegativities of the Groups Group



Group



F Cl Br I CF3 CCl3 CHCl2

4.0 2.8 2.7 2.2 3.4 3.0 2.8

OH OCH3 NO2 NH2 N(CH3)2

3.7 3.7 3.4 3.4 3.0

Group C˜N C ˜ CH CH ¨ CH2 C6H5 COOH SiH3 PH2 SH

 3.3 3.3 3.0 3.0 2.8 2.2 2.3 2.8

Electronegativities have important uses in chemistry in addition to predicting the amount of ionic character in a bond. The bond stretching force constant k (in units of 105 dynes · cm1) can be estimated for stable molecules exhibiting their normal covalences by the expression: k  1.67 N

 d  A

B

2

3 4

 0.30

where N is the bond order (i.e., the effective number of covalent or ionic bonds acting between the two atoms A and B) and d is the internuclear distance in angstroms. An estimate of the percent ionic character may be made for organometallic compounds of the type alkyl-metal for metals in common use in organic synthesis. Among the alkali metals (row 1 of the Periodic Table, these are Li (43%), Na (47%), and K (51%)). The percent ionic character for an organomagnesium compound (typically a Grignard reagent), the bond is estimated to be 34% ionic. The more covalent organozinc and organocadmium compounds have correspondingly less ionic character: Zn (18%) and Cd (15%). Electronegativities have also been estimated for various common substituent groups. They are arranged in Table 3.2B in clusters of related residues. The values for the individual halogens are from Table 3.2A.

3.11

PROPERTIES OF ATOMS, RADICALS, AND BONDS

Electronegativity is proportional to the work function , which is the energy necessary to just remove an electron from the metal surface in thermoelectric or photoelectric emission.   0.44  0.15

ELECTRON AFFINITY The electron affinity of an atom A is defined as the energy released when an atom and an electron react to form a negative ion in the gas phase at 0 K. A(g)  e  A(g) An example is the capture of an electron by chlorine to give chloride anion. Cl(g)  e  Cl(g). Conceptually related to this is the ionization potential, which is the energy for the process A l A  e. An example is the loss of an electron by an alkali metal to give the alkali metal cation. Na l Na  e The second ionization potential carried this process further, that is, A l A2  e and so on for the third or more ionization potentials. Both electron affinities and ionization potentials are typically expressed in electron volts (eV). Data for electron affinities are given in Table 3.3. Uncertainty in the final data figures is given in parentheses. Source: H. Hotop and W. C. Lineberger, J. Phys. Chem. Ref. Data, 4: 539 (1975). Data for ionization potentials are available in C. E. Moore, National Bureau of Standards U. S. Publication NSRDS-NBS, 34 (1970). TABLE 3.3 Electron Affinities of Elements, Molecules and Radicals A. Elements

Element

Electron affinity, eV*

Element

Aluminum Antimony Argon Arsenic Astatine Barium

0.46(3) 1.05(5) 0 0.80(5) 2.8(2) 0

Beryllium Bismuth Boron Bromine Cadmium Calcium

Electron affinity, eV* 0 1.1(2) 0.28(1) 3.364(4) 0 0

3.12

SECTION 3

TABLE 3.3 Electron Affinities of Elements, Molecules and Radicals (continued) A. Elements

Electron affinity, eV*

Element Carbon Cesium Chlorine Chromium Cobalt Copper Fluorine Francium Gallium Germanium Gold Hafnium Helium Hydrogen Indium Iodine Iridium Iron Krypton Lanthanum Lead Lithium Magnesium Manganese Mercury Molybdenum Neon Nickel Niobium Nitrogen Osmium

1.268(5) 0.4715(5) 3.615(4) 0.66(5) 0.7(2) 1.226(10) 3.399(3) (0.456) 0.30(15) 1.2(1) 2.3086(7) 0 0 0.754 209(3) 0.30(15) 3.061(4) 1.6(2) 0.25(20) 0 0.5(3) 1.1(2) 0.620(7) 0 0 0 1.0(2) 0 1.15(10) 1.0(3) 0.07(8) 1.1(3)

Electron affinity, eV*

Element Oxygen Palladium Phosphorus Platinum Polonium Potassium Radon Rare earths Rhenium Rhodium Rubidium Ruthenium Scandium Selenium Silicon Silver Sodium Strontium Sulfur Tantalum Technetium Tellurium Thallium Tin Titanium Tungsten Vanadium Xenon Yttrium Zinc Zirconium

1.462(3) 0.6(3) 0.743(10) 2.128 1.9(3) 0.5012(5) 0

0.5 (estimate) 0.15(10) 1.2(3) 0.4860(5) 1.1(3) 0 2.0206(3) 1.385(5) 1.303(7) 0.546(5) 0 2.0772(5) 0.6(4) 0.7(3) 1.9708(3) 0.3(2) 1.25(10) 0.2(2) 0.6(4) 0.5(2) 0 0.0(3) 0 0.5(3)

Electron affinity, eV*

Molecule

Electron affinity, eV*

2.65 1.34 3.91 0.45

SF6 2,3,5,6-Tetrachlorobenzoquinone Tetracyanoethylene

B. Molecules

Molecule BF3 p-Benzoquinone NO2 O2 * To convert into kJ · mol

1

multiply by 96.48. To convert into kcal · mol

1

multiply by 23.06.

1.43 2.40 2.88

3.13

PROPERTIES OF ATOMS, RADICALS, AND BONDS

TABLE 3.3 Electron Affinities of Elements, Radicals and Molecules (continued) C. Radicals

Radical CH3 C2H5 C6H5 CCl3 CF3 CN NH2 C6H5NH (C6H5)2N

Electron affinity, eV*

Radical

Electron affinity, eV*

1.08 0.89 2.20 1.22 1.85 3.17 1.12 1.55 1.19

OH CF3O CH3O PH2 SH CH3S SCN SeCN SiF3

1.83 1.35 0.38 1.60 2.19 1.32 2.17 2.64 3.35

* To convert into kJ · mol1 multiply by 96.48. To convert into kcal · mol1 multiply by 23.06.

BOND LENGTHS AND STRENGTHS The bonds most commonly encountered in organic chemistry are those between carbons and between carbon and heteroatoms of the first row of the Periodic Table. Generally and very approximately, single bonds between two carbon atoms are about 1.5 Å in length and have strengths near to, but usually less than, 100 kcal/mole (418 kJ/mol). Likewise, carbon– carbon double bonds are stronger (~150 kcal/mol) and shorter (~1.35 Å). Triple bonds are shorter still (C ˜ C1.2 Å, ~200 kcal/mol). Bonds between carbon and either nitrogen or oxygen are somewhat shorter owing to the heteroatom’s electronegativity. A few general examples are shown below and detailed data may be found in the Table 3.4. General Trends in the Length of Common Organic Chemical Bonds Bond

Length (Å)

Bond

Length (Å)

Bond

Length (Å)

CˆC C¨C C˜C

1.54 1.33 1.21

CˆO C¨O CˆN C¨N C˜N

1.43 1.20 1.47 1.28 1.15

H ˆ C(sp3) NˆH OˆH C ˆ Cl

1.12 1.03 0.97 1.76

3.14

SECTION 3

TABLE 3.4A Bond Lengths between Carbon and other Elements The numbers in parentheses following a numerical value represent the standard deviation of that value in terms of the final listed digit. To convert the bond length from angstroms into nanometers, multiply by 0.1; to convert angstroms into picometers, multiply by 100.

Bond type

Bond length, Å*

Carbon–carbon Single bond Paraffinic: ˆ C ˆ C ˆ In presence of ˆ C ¨ C ˆ or of aromatic ring In presence of ˆ C ¨ O bond In presence of two carbon–oxygen double bonds In presence of two carbon–carbon double bonds Aryl ˆ C ¨ O In presence of one carbon–carbon triple bond: ˆ C ˆ C ˜ C ˆ In presence of one carbon-nitrogen triple bond: ˆ C ˆ C ˜ N In compounds with tendency to dipole formation, e.g., C ¨ C ˆ C ¨ O In aromatic compounds In presence of carbon–carbon double and triple bonds: ˆC¨CˆC˜Cˆ In presence of two carbon-carbon triple bonds: ˆ C ˜ C ˆ C ˜ C ˆ

1.541(3) 1.53(1) 1.516(5) 1.49(1) 1.426(5) 1.47(2) 1.460(3) 1.464(5) 1.44(1) 1.395(3) 1.426(5) 1.373(4)

Double bond Single: ˆ C ¨ C ˆ Conjugated with a carbon–carbon double bond: ˆ C ¨ C ˆ C ¨ C ˆ Conjugated with a carbon-oxygen double bond: ˆ C ¨ C ˆ C ¨ O Cumulative: ˆ C ¨ C ¨ C ˆ or ˆ C ¨ C ¨ O

1.337(6) 1.336(5) 1.36(1) 1.309(5)

Triple bond Simple: ˆ C ˜ C ˆ Conjugated: ˆ C ˜ C ˆ C ¨ C ˆ , ˆ C ˜ C ˆ C ¨ O, or ˆ C ˜ C ˆ aryl Bond type

1.204(2) 1.206(4)

Bond length, Å Carbon–halogen

Paraffinic: R ˆ X Olefinic: ˆ C ¨ C ˆ X Aromatic: Ar ˆ X Acetylenic: ˆ C ˜ C ˆ X

Fluorine

Chlorine

Bromine

Iodine

1.379(5) 1.333(5) 1.328(5) (1.27)

1.767(2) 1.719(5) 1.70(1) 1.635(5)

1.938(5) 1.89(1) 1.85(1) 1.795(10)

2.139(1) 2.092(5) 2.05(1) 1.99(2)

Bond type

Bond length, Å

Carbon–hydrogen Paraffinic In methane In CD4 In monosubstituted carbon: H ˆ C ˆ Y

1.092 1.094 1.096(5)

X

In disubstituted carbon:

H

C Y

1.073(5)

3.15

PROPERTIES OF ATOMS, RADICALS, AND BONDS

TABLE 3.4A Bond Lengths between Carbon and Other Elements (continued) Bond type

Bond length, Å

Carbon–hydrogen (continued) Paraffinic (continued) X

In trisubstituted carbon:

H

C

1.070(7)

Y

Y

Olefinic Simple: H ˆ C ¨ C ˆ Cumultative carbon–carbon double bonds: H ˆ C ¨ C ¨ C ˆ Cumulative carbon–carbon–oxygen double bonds: HˆCˆC¨C¨O

1.083(5) 1.07(1) 1.08(1)

Aromatic

1.084(5)

Acetylenic (in C2H2, 1.059)

1.055(5)

In small rings

1.081(5)

In presence of a carbon triple bond: H ˆ C ˜ C ˆ

1.115(4)

Carbon–nitrogen Single bond Paraffinic: 3 covalent nitrogen: RNH2, R2NH, R3N 4 covalent nitrogen: RNH3, R3N ˆ BX3 In ˆ C ˆ N ¨ In aromatic compounds In conjugated heterocyclic systems (partial double bond) In ˆ N ˆ C ¨ O (partial double bond)

1.472(5) 1.479(5) 1.475(10) 1.43(1) 1.353(5) 1.322(5)

Double bond: ˆ C ¨ N ˆ

1.32

Triple bond (in CN radical, 1.1774): ˆ C ˜ N

1.157(5)

Carbon–oxygen Single bond Paraffinic and saturated heterocyclic: ˆ C ˆ O ˆ

Strained, as in epoxides:

C

C

1.426(5)

1.435(5)

O

In aromatic compounds, as Ar ˆ OH Longer bond in carboxylic acids and esters (HCOOH, 1.312) In conjugated heterocyclics, as furan

1.36(1) 1.358(5) 1.371(16)

3.16

SECTION 3

TABLE 3.4A Bond Lengths between Carbon and Other Elements (continued) Bond type

Bond length, Å

Carbon–oxygen (continued) Double bond In CO In CO In CO2 In HCO In carbonyls In aldehydes and ketones In acyl halides: R ˆ CO ˆ X Shorter bond in carboxylic acids and esters In zwitterion forms In O ¨ C ¨ In isocyanates: RN ¨ C ¨ O In conjugated systems, as in partial triple bond: O ¨ C ˆ C ¨ C In p-quinones In metal acetylacetonates In calcite: CaCO3

1.115 1.128 1.177 1.198(8) 1.145(10) 1.215(5) 1.171(4) 1.233(5) 1.26(1) 1.160(1) 1.17(1) 1.215(5) 1.15(2) 1.28(2) 1.29(1)

Carbon–selenium Single bond Paraffinic: ˆ C ˆ Se ˆ In presence of fluorine, as in perfluoro compounds: ˆ CF ˆ Se ˆ

1.98(2) 1.95(2)

Double bond In Se ¨ C ¨ , as SeCS and SeCO In CSe radical

1.709(3) 1.67 Carbon–silicon

Alkyl substituent: H3C ˆ Si or H2C ˆ Si Aryl substituent: aryl ˆ Si Electronegative substituent: R ˆ Si ˆ X

1.870(5) 1.843(5) 1.854(5) Carbon–sulfur

Single bond Paraffinic: ˆ C ˆ S ˆ In presence of fluorine, as in perfluoro-compounds: ˆ CF ˆ S ˆ In heterocyclic systems: partial double bonds

1.817(5) 1.835(1) 1.718(5)

Double bond In S ¨ C: thiophene, S ¨ CR2 In sulfoxides and sulfones In presence of second carbon–carbon double bond: S ¨ C ˆ C ¨ C ˆ In SC radical [in CS2, 1.554(5)]

1.71(1) 1.80(1) 1.555(1) 1.5349(2)

3.17

PROPERTIES OF ATOMS, RADICALS, AND BONDS

TABLE 3.4A Bond Lengths between Carbon and Other Elements (continued) Bond type

Bond length, Å

Bond type

Bond length, Å

Other elements and carbon C ˆ Al C ˆ As (paraffinic) CˆB C ˆ Be C ˆ Bi C ˆ Co C ˆ Cr C ˆ Fe C ˆ Ge Alkyl Aryl C ˆ Hg in Hg(CN)2

2.24(4) 1.98(1) 1.56(1) 1.93 2.30 1.83(2) 1.92(4) 1.84(2) 1.98(3) 1.945(5) 2.07(1) 1.99(2)

C ˆ In C ˆ Mo C ˆ Ni C ˆ Pb (alkyl) C ˆ Pd C ˆ Sb (paraffinic) C ˆ Sn alkyl electronegative substituent C ˆ Te C ˆ Tl CˆW

2.16(4) 2.08(4) 2.107(5) 2.30(1) 2.27(4) 2.202(16) 2.143(5) 2.18(2) 1.904 2.705(5) 2.06

TABLE 3.4B Bond Lengths between Elements Other than Carbon Elements

Bond type

Bond length, Å

Elements

Boron BˆB B ˆ Br B ˆ Cl BˆF BˆH BˆN BˆO

B2H6 BBr3 BCl3 BF3, R2BF Boranes Bridge Borazoles B(OH)3, (RO)3B

Bond type

Bond length, Å

Hydrogen (continued) 1.77(1) 1.87(2) 1.72(1) 1.29(1) 1.21(2) 1.39(2) 1.42(1) 1.362(5)

H ˆ Mg H ˆ Na H ˆ Sb H ˆ Se H ˆ Sn D ˆ Br D ˆ Cl DˆI T ˆ Br T ˆ Cl

MgH NaH H3Sb H2Se SnH4 DBr DCl

1.731 1.887 1.707 1.460 1.701 1.4144 1.2746 1.6165 1.4144 1.2740

Hydrogen Nitrogen H ˆ Al H ˆ As H ˆ Be H ˆ Br H ˆ Ca H ˆ Cl HˆF H ˆ Ge HˆI HˆK H ˆ Li

AlH AsH3 BeH HBr CaH HCl HF GeH4 HI KH LiH

1.646 1.519 1.343 1.408 2.002 1.274 0.917 1.53 1.609 2.244 2.595

N ˆ Cl NˆF NˆH

NˆD NˆN

NO2Cl NF3 NH4 NH3, RNH2 H2NNH2 R ˆ CO ˆ NH2 HN ¨ C ¨ S ND HN3 R2NNH2

1.79(2) 1.36(2) 1.034(3) 1.012 1.038 0.99(3) 1.013(5) 1.041 1.02(1) 1.451(5)

3.18

SECTION 3

TABLE 3.4B Bond Lengths between Elements Other than Carbon (continued ) Elements

Bond type

Bond length, Å

Elements

Nitrogen (continued)

NˆO

N¨O

N ˆ Si

N2O N2 NO2Cl RO ˆ NO2 NO2 N2O RNO2 NO SiN

1.126(2) 1.116 1.24(1) 1.36(2) 1.188(5) 1.186(2) 1.22(1) 1.0619 1.572

PˆH PˆI PˆN PˆO

PˆS

PˆC

OˆO

O ˆ Al O ˆ As O ˆ Ba O ˆ Cl O ˆ Mg O ˆ Os O ˆ Pb

H2O ROH OH HOOH D2O OD HO ˆ OH O2 O2 O22 O3 AlO As4O6 (bridges) BaO ClO2 OCl2 MgO OsO4 PbO

0.958 0.97(1) 1.0289 0.960(5) 0.9575 0.9699 1.48(1) 1.227 1.26(2) 1.49(2) 1.278(5) 1.618 1.79 1.940 1.484 1.68 1.749 1.66 1.934

Si ˆ Br Si ˆ Cl Si ˆ F Si ˆ H Si ˆ I Si ˆ O Si ˆ Si

2.23(1) 2.00(2) 1.55(3)

1.424(5) 2.52(1) 1.491 1.447 1.67 1.54(4) 2.12(5) 2.08(2) 2.20(2) 1.562 1.87(2)

SiBr4, R3SiBr SiCl4, R3SiCl SiF4, R3SiF SiF6 SiH4 R3SiH SiI4 R3SiI R3SiOR H3SiSiH3

2.16(1) 2.019(5) 1.561(3) 1.58 1.480(5) 1.476(5) 2.34 2.46(2) 1.633(5) 2.30(2)

Sulfur S ˆ Br S ˆ Cl SˆF SˆH

SˆO PBr3 PCl3 PFCl2

PH3, PH4 PI3 Single bond Single bond p3 bonding sp3 bonding p3 bonding sp3 bonding In rings Single bond p3 bonding Silicon

Phosphorus P ˆ Br P ˆ Cl PˆF

Bond length, Å

Phosphorus (continued)

Oxygen OˆH

Bond type

SˆS

SOBr2 S2Cl2 SOF2 H2S RSH D2S SO2 SOCl2 RSSR

2.27(2) 1.585(5) 1.585(5) 1.333 1.329(5) 1.345 1.4321 1.45(2) 2.05(1)

TABLE 3.5 Bond Strengths The quantity D0(A ˆ B) corresponds to the bond dissociation energy at 0 K, all species considered to be ideal gases, for a bond A ˆ B which is broken through the reaction: Eq. AB l A  B where

D0  Hf 0(A)  Hf 0(B)  Hf 0(AB)

D0 at 298 K, or Hf298, is greater than D0 at 0 K by an amount which lies between RT and 3/2 RT, or between 0.6 and 0.9 kcal · mol1. In polyatomic molecules this difference may be somewhat greater. It is important to note that the bond dissociation energy refers to the enthalpy change Hf in the dissociation process. The strengths of carbon–carbon bonds are greatest for triple bonds and typically decrease with bond order. Other factors play a role as well. A carbon–carbon single bond between two multiple bonds will share some additional electron density and be correspondingly strengthened. Bonds are weaker than “normal” when cleavage of a bond gives a particularly stable species. For example, cleavage of a single bond in ethylbenzene to give benzyl radical and methyl radical, C6H5CH2 ˆ CH3 l C6H5CH2●  ●CH3, is favorable because benzyl radical is stable. Thus, the C ˆ C bond strength in this case is only 72 kcal/mol compared to the single bond of propane, which is 85 kcal/mol. Hexamethylethane may dissociate into two t-butyl radicals [(CH3)3C●]. The combination of steric crowding and the formation of stabilized radicals makes the CˆC bond strength in (CH3)3Cˆ C(CH3)3 only about 68kcal/mol. A few selected examples follow: The numbers in parentheses following a numerical value represent the standard deviation of that value in terms of the final listed digit(s). To convert the tabulated values (in kcal · mol1) to kJ · mol1, multiply by 4.184. Source: T. L. Cottrell, The Strengths of Chemical Bonds, 2nd ed., Butterworth, London, 1958; B. deB. Darwent, National Standard Reference Data Series, National Bureau of Standards, no. 31, Washington, 1970; S. W. Benson, J. Chem. Educ., 42: 502 (1965); and J. A. Kerr, Chem. Rev., 66: 465 (1966). 230 kcal H

H 163 kcal

H

H

H

H 150 kcal

H

H2 C H3C

H3C H3C H3C

85 kcal CH3 68 kcal CH3 CH3 CH3

H

100 kcal

100 kcal

H

H

3.19

H H 117 kcal H

CH3

CH 2 CH 3

72 kcal

3.20 TABLE 3.5 Bond Strengths (continued) D0, kcal · mol1

Bond

Hf298, kcal · mol1

Bond

Boron H3B ˆ BH3 F2B ˆ F

Hf298, kcal · mol1

Carbon (continued) 35 133(20)

Bromine Br ˆ Br Br ˆ CH3 Br ˆ CH2Br Br ˆ CHBr2 Br ˆ CBr3 Br ˆ CCl3 Br ˆ CF3 Br ˆ CF2CF3 Br ˆ CF2CF2CF3 Brˆ CHF2 Br ˆ Cl Br ˆ F Brˆ CN Br ˆ CO ˆ C6H5 Br ˆ N Br ˆ NF2

D0, kcal · mol1

45.45(1) 67(2)

49(3) 51(3)

51.6(1) 67.2

46.10(1) 68(2) 61(3) 62(4) 50(3) 52(3) 68(3) 68.7(15) 66.5(15) 69 52.3(1) 68.1 91 64

68(5) 53

CH3 ˆ CH2CN CH3 ˆ CH(CH3)CN CH3 ˆ C(C6H5)CN(CH3) C2H5 ˆ CH2CN CH3 ˆ CF3 CH2F ˆ CH2F CF3 ˆ CF3 CF2 ¨ CF2 CF3 ˆ CN CH2 ˆ CO CH3 ˆ CHO CH3CO ˆ CF3 CH3CO ˆ COCH3 C6H5CO ˆ COC6H5 C6H5CH2CO ˆ CH2C6H5 C6H5CH2 ˆ COOH (C6H5CH2)2CH ˆ COOH NC ˆ CN CF3 ˆ NF2 CH3 ˆ NH2 C6H5CH2 ˆ NH2

80.6

143(5)

73(2) 79(2) 60 76.9(17) 101.2(11) 88(2) 97(2) 76(3) 120 81.9 75 73.8 67(2) 66.4 65.4 68.1 59.4 144(5) 65(3) 79(3) 72(1)

Br ˆ NO Br ˆ O

27.8(15) 55.3(1)

28.7(15) 56.2(1)

119(5)

230(2) 163 88 69(2) 80 93 72 71 71 67(2) 29 72 117 67.5 15 100 100 150 121(5)

Carbon HC ˜ CH H2C ¨ CH2 CH3 ˆ CH3 CH3 ˆ C(CH3)2CH3 CH3 ˆ C(CH3)3 CH3 ˆ C6H5 CH3 ˆ CH2C6H5 CH3 ˆ CH(CH3)C6H5 C2H5 ˆ CH2C6H5 C3H7 ˆ CH2C6H5 CH3 ˆ (CH ¨ CH2) CH3 ˆ (CH2CH ¨ CH2) CH3 ˆ (C ˜ CH) (CH3)3C ˆ C(CH3)3 (CH3)3C ˆ C(C6H5)3 (CH2 ¨ CH) ˆ (CH ¨ CH2) C6H5 ˆ C6H5 (HC ˜ C) ˆ (C ˜ CH) CH3 ˆ CN

CH3 ˆ NHC6H5 CH3 ˆ N(CH3)C6H5 C6H5CH2 ˆ NHCH3 C6H5CH2 ˆ N(CH3)2 CH3 ˆ (N ¨ NCH3) C2H5 ˆ (N ¨ NC2H5) (CH3)3C ˆ [N ¨ NC(CH3)3] C6H5CH2 ˆ (N ¨ NCH2C6H5) CF3 ˆ (N ¨ NCF3) H2C ¨ NH HC ˜ N CH3 ˆ NO C2H5 ˆ NO C3H7 ˆ NO (CH3)2CH ˆ NO C4H9 ˆ NO C6H5 ˆ NO Cl3C ˆ NO F3C ˆ NO C6F5 ˆ NO NC ˆ NO CH3 ˆ NO2 C2H5 ˆ NO2 CH3 ˆ OCH3

68 65 69(1) 61(1) 52.5 50.0 43.5 37.6 55.2 154(5) 224 41.8(9) 42.0(13) 40.1(18) 41.0(13) 51.5(10) 51.5(10) 32 31 50.5(10) 29(3) 59(3) 62 80

3.21

3.22

TABLE 3.5 Bond Strengths (continued) D0, kcal · mol1

Bond

Hf298, kcal · mol1

Carbon (continued) CH3 ˆ OC6H5 CH3 ˆ OCH2C6H5 C2H5 ˆ OC6H5 C6H5CH2 ˆ OCOCH3 C6H5CH2 ˆ OCOC6H5 CH3CO ˆ OCH3 CH3 ˆ O ˆ SOCH3 CH2 ¨ CHCH2 ˆ OSOCH3 C6H5CH2 ˆ OSOCH3 C¨O H2C ¨ O OC ¨ O SC ¨ O C˜O CH3 ˆ SH CH3 ˆ SC6H5 CH3 ˆ SCH2C6H5 OC ˆ S eH2 ˆ CH3 eH2CH2 ˆ CH3 (eH2)2C ˆ CH3 eHCH ˆ CH3 CH3

D0, kcal · mol1

Bond

Hf298, kcal · mol1

Chlorine (continued) 91 67 51 67

256.2(1) 125.7(1) 148 71(3)

72.9

69 97 67 50 53 257.3(1) 175 127.2(1) 150 257 73(3) 68(2) 59(2) 74.2 96 25.5 51 32 27.5

Cl ˆ COC6H5 Cl ˆ Cl Cl ˆ Cl Cl ˆ ClO O3Cl ˆ ClO4 Cl ˆ F O3Cl ˆ F Cl ˆ N Cl ˆ NCl Cl ˆ NCl2 Cl ˆ NF2 Cl ˆ NH2 Cl ˆ NO Cl ˆ NO2 Cl ˆ O OCl ˆ O O2Cl ˆ O Cl ˆ SiCl3 Cl ˆ CH3 Cl ˆ Cl

74(3) 94 57.3(1) 33.3(10) 58 59.5(5)

37.0(15) 33(1) 64(1) 58(3)

61 62 67 91 ca 32 60(6) 38.0(15) 34(1)

48(1) 111 51 94 Fluorine

F ˆ CH3 F ˆ C(CH3)3

108(5) 105

CH3

35

CH3

11.5

(CH3)2C(eH2) ˆ CH3 fCH2 ˆ CH3 (CH3)2C(f) ˆ CH3 eH2CO ˆ CH3 fC ˆ CH3 f2C ˆ CH3 CH3 ˆ CH3 CH2 ˆ CH3 CH2 ¨ CH2 HC ˜ CH

20 12 7 30 11 20 46 119 162 223 Chlorine

3.23

Cl ˆ C Cl ˆ CH3 Cl ˆ C(CH3)3 Cl ˆ CH2Cl Cl ˆ CCl3 Cl ˆ CF3 Cl ˆ CCl2F Cl ˆ CF2Cl Cl ˆ CF2CF3 Cl ˆ (CH ¨ CH2) Cl ˆ CN Cl ˆ COCl Cl ˆ COCH3

F ˆ C6H5 F ˆ CCl3 F ˆ CCl2F F ˆ CClF2 F ˆ CF3 F ˆ COCH3 FˆF OF ˆ F O2F ˆ F FˆN F ˆ NF F ˆ NF2 F ˆ NO F ˆ NO2 F ˆ F

116 106(5) 110(6) 117(6) 125(4) 119 37(1) 64(3) 18.4 71(10) 75(5) 57(2) 55.2(10) 46(5)  60 Gallium

CH3 ˆ Ga(CH3)3 80(10)

80.8 81(5) 78.5 74(3) 70(5) 86.1(8) 73(2) 76(2) 82.7(17) 84 105 78.5 83.5

72(10) 76(5) 58(2) 56.3(10)

59.5 Hydrogen

H ˆ Br HˆC H ˆ CH H ˆ CH2 H ˆ CH3 D ˆ CD3 H ˆ (C ˜ CH) H ˆ (C ¨ CH2) H ˆ CH2CH3 H ˆ CH2C ˜ CH H ˆ CH2CH ¨ CH2

86.6(1) 80 112.3(1) 102(2) 104.92(5)

87.5(1) 81.0(5) 108(6) 113(1) 103(2) 125(1) 102 98(1) 93.9(12) 85

3.24

TABLE 3.5 Bond Strengths (continued) D0, kcal · mol1

Bond

Hf298, kcal · mol1

Bond

Hydrogen (continued) H ˆ cyclopropyl H ˆ CH2CH2CH3 H ˆ CH(CH3)2 H ˆ cyclobutyl H ˆ CH2CH(CH3)2 H ˆ CH(CH3)CH2CH3 H ˆ C(CH3)3

D0, kcal · mol1 Hydrogen (continued)

101(3) 98(2) 94.5 95(3) 86 95(1) 91

H ˆ Cl H ˆ CO H ˆ CHO H ˆ COOH H ˆ COCH3 H ˆ COCH2CH3

102.3(1) 30(2) 87(1) 90 87(1) 87(1) 92(1)

H

81(1)

H

H

CH

CH2

CH

CH2

CH

80(1)

H H

82(1) CH

CH2 C

CH2

99(1) CH2

H ˆ C(CH3)2CH ¨ CH2 H ˆ cyclopentyl H ˆ CH2C(CH3)3 H ˆ C6H5 H ˆ CH2C6H5

Hf298, kcal · mol1

79 94.5(10) 100(1) 103 85(1)

O

H ˆ COC6H5 H ˆ COCF3 HˆF HˆH HˆD DˆD HˆI HˆN H ˆ NH H ˆ NH2 H ˆ NHCH3 H ˆ N(CH3)2 H ˆ NHC6H5 H ˆ N(CH3)C6H5 H ˆ NF2 H ˆ N3

135(1) 103.25 104.07(1) 105.05(1) 70.4(1) 85(2) 89(2) 103(2)

87(1) 91(2) 135.8 104.19 105.00 105.96 71.3(1) 85(2) 90(2) 104(2) 103(2) 95(2) 80(3) 74(3) 76(3) 85

H ˆ C(C6H5)3

75 74

H

3.25

H ˆ cyclohexyl H ˆ cycloheptyl H ˆ norbornyl H ˆ CH2Br H ˆ CHBr2 H ˆ CBr3 H ˆ CH2Cl H ˆ CHCl2 H ˆ CCl3 H ˆ CCl2CHCl2 H ˆ CCl2CCl3 H ˆ CH2F H ˆ CHF2 H ˆ CF3 H ˆ CF2Cl H ˆ CH2CF3 H ˆ CF2CH3 H ˆ CF2CF3 H ˆ CF2CF2CF3 H ˆ CH2I H ˆ CHI2 H ˆ CN H ˆ CH2CN H ˆ CH(CH3)CN H ˆ C(CH3)2CN H ˆ CH2NH2 H ˆ CH2Si(CH3)3 H ˆ CH2COCH3

95.5(10) 92.5(10) 97(3) 97(5) 88(2)

89(3)

105(3)

127(5)

104 90(2) 101 99.0 90(3) 94(2) 95(2) 101(2) 101(2) 106(3) 104(1) 106.7(11) 99.5(1) 103.1(15) 104(2) 103(2) 103(2) 129(5) ca 93 90(2) 87(2) 95(2) 99(1) 98.3(18)

H ˆ NO HˆO H ˆ OH H ˆ OCH3 H ˆ OCH2CH3 H ˆ OC(CH3)3 H ˆ OCH2C(CH3)3 H ˆ OC6H5 H ˆ ONO H ˆ ONO2 H ˆ OOH H ˆ OOCCH3 H ˆ OOCCH2CH3 H ˆ OOCC3H7 H ˆ SH H ˆ SCH3 H ˆ SiH3 H ˆ Si(CH3)3 H ˆ SiCl3 eH2 ˆ H eH ˆ H eˆH eH2CH2 ˆ H fCH2 ˆ H eO ˆ H eHCH ˆ H Hˆf H ˆ Of H ˆ OeH2 H ˆ OOe eH ˆ H eOCH2 ˆ H

101.3(5) 118.0(2)

88.5(20)

90(1)

 49 102.3(5) 119.2(2) 104.4(10) 104.2 105(1) 102.3(15) 88(5) 78.3(5) 101.2(5) 89.5(20) 112(4) 110(4) 103(4) 91(1) ca 88 94(3) 90(3) 91.3(14) 106 106 81 39 22 19 43 102 47 31 31 ca 125 43.5

3.26

TABLE 3.5 Bond Strengths (continued) D0, kcal · mol1

Bond

Hf298, kcal · mol1

Bond

Hydrogen (continued)

Hf298, kcal · mol1

225.07(1) 20(1)

225.96(1) 21(1) 71(2) 65 63 51 9(1) 114.9(10) 9.5(2) 13.7(5) 40 73 109(10) 115 226 200 155 56 56

Nitrogen

eH2CO ˆ H

36

H

40

H

47.5

H

24

C ˆ H CH3 ˆ H CH3CH2 ˆ H CH2CH3 ˆ H H ˆ H

85 30 29 79 62 Iodine

I ˆ Br I ˆ CH3 I ˆ CH2CH3 I ˆ CH(CH3)2 I ˆ C(CH3)2 I ˆ CH2CF3 I ˆ CF2CH3

D0, kcal · mol1

41.9(1) 54(3)

42.5(1) 55.5(30) 53.5 53 49.5 56(1) 52(1)

NˆN F2N ˆ NF2 H2N ˆ NH2 H2N ˆ NHCH3 H2N ˆ N(CH3)2 H2N ˆ NHC6H5 HN ˆ N2 ON ˆ N ON ˆ NO2 O2N ˆ NO2 NN ˆ O ON ˆ O HN ¨ NH HN ¨ O N˜N N ˆ N N ˆ NO NN ˆ O ON ˆ O

113.5(10) 8.4(2) 12.7(5)

Osmium O3Os ˆ O

72(5) Oxygen

HO ˆ CH3 HO ˆ (CH ¨ CH2)

88.5(30)

90(3) 87

I ˆ CF2CF3 I ˆ C3F7 I ˆ (CH ¨ CHCH3) I ˆ CH3 I ˆ C6H5 I ˆ C6F5 I ˆ Cl I ˆ COCH3 I ˆ CN IˆF I ˆ H IˆI I ˆ I I ˆ NO I ˆ NO2

49.7(1)

66.4(10) 35.60(1)

51(1) 50(1) 41 62 64(1) 66 50.5(1) 52.5 73(1) 67(1) 70 36.15 61 17(1) 18(1)

Lead CH3 ˆ Pb(CH3)3

49.4(10) Lithium

Li ˆ H

58

HO ˆ CH2CH ¨ CH2 HO ˆ C6H5 HO ˆ CH2C6H5 HO ˆ CHO HO ˆ COCH3 HO ˆ COCH2CH3 HO ˆ Cl HO ˆ I HO ˆ NCH3 HO ˆ OC(CH3)3 OˆO HO ˆ OH CF3O ˆ OCF3 CH3O ˆ OCH3 C2H5O ˆ OC2H5 C3H7O ˆ OC3H7 O ˆ OF O ˆ O2ClF FO ˆ OF O ¨ PBr3 O ¨ PCl3 O ¨ PF3 O ˆ O HO ˆ CH3

110.7 58 62(20) 119(5) 122(5) 130(5) 168 67 Phosphorus

Mercury

3.27

Hg ˆ Br CH3 ˆ HgCH3 C2H5 ˆ HgC2H5 C3H7 ˆ HgC3H7 (CH3)2CH ˆ HgCH(CH3)2 C6H5 ˆ HgC6H5

117.97(10) 49.5(5)

109 103 77 96(3) 108(5) 43 60(3) 56(3) 50 46(2) 119.11 51.1(5) 46 37.6(2) 38 37

16.4(10)

17.4(10) 57.5 43.7(10) 47.1 40.7 68

P ˆ Br P ˆ Cl PˆF PˆH PˆO PˆP P¨S

141.5(10) 115(2) 82

63.7 78.5 117 79(1) 142.3(10) 116(2)

3.28

TABLE 3.5 Bond Strengths (continued) D0, kcal · mol1

Bond

Hf298, kcal · mol1

Ruthenium O ˆ RuO3 Selenium 58 68 81(23) 65 Silicon Si ˆ Br Si ˆ Cl Si ˆ F Si ˆ H Si ˆ I Si ˆ N Si ˆ O Si ˆ S Si ˆ Se Si ˆ Si H3Si ˆ SiH3 (CH3)3Si ˆ Si(CH3)3 (C6H5)3Si ˆ Si(C6H5)3 Si ˆ Te

Hf298, kcal · mol1

Sulfur 104

Se ˆ Cl Se ˆ F Se ˆ O Se ˆ Se

D0, kcal · mol1

Bond

69(14) 76(12)

61 16 115 123.6(20) 130.8(20) 81.9(10) 101.5(15)

83.2(10) 102.5(15) 65(5)

60 104 161 155 Tin

135 74(6) 56 ca 104 185(7) 147(3) 134(6) 42 81(4) 81 88(7) 122(9)

S ˆ Cl O2S ˆ F SˆN SˆO OS ˆ O O2S ˆ O SˆS HS ˆ SH S ˆ Te HS ˆ H HS ˆ H OS ˆ O

BrSn ˆ Br Br3Sn ˆ Br C2H5Sn ˆ (C2H5)3 Sn ˆ Cl Sn ˆ H Sn ˆ I Sn ˆ O Sn ˆ S

130(5) 111(5)

78 65 ca 57 76 61.0(7) 65 131(5) 112(5)

Xenon Xe ˆ F

31(1)

Zinc

Sodium Na ˆ H Na ˆ K Na ˆ Na Na ˆ OH

47 14.3 17.3

Zn ˆ H C2H5Zn ˆ C2H5 91(3)

19.6(5) ca 48

3.29

3.30

SECTION 3

BOND AND GROUP DIPOLE MOMENTS All bonds between equal atoms are given zero values. Because of their symmetry, methane and ethane molecules are nonpolar. The principle of bond moments thus requires that the CH3 group moment equal one H ˆ C moment. Hence the substitution of any aliphatic H by CH3 does not alter the dipole moment, and all saturated hydrocarbons have zero moments as long as the tetrahedral angles are maintained. The group moment always includes the C ˆ X bond. When the group is attached to an aromatic system, the moment contains the contributions through resonance of those polar structures postulated as arising through charge shifts around the ring. All values for bond and group dipole moments in Tables 3.6 and 3.7 were obtained in benzene solution. TABLE 3.6 Bond Dipole Moments Bond HˆC Aliphatic Aromatic CˆC C˜C CˆO Ether, aliphatic Alcohol, aliphatic C¨O Aliphatic Aromatic OˆH CˆS C¨S SˆH SˆO S¨O Aliphatic Aromatic C ˆ N, aliphatic C¨N C ˜ N (nitrile) NC (isonitrile) NˆH NˆO N¨O N: lone pair on sp3N C ˆ P, aliphatic PˆO P¨O PˆS P¨S B ˆ C, aliphatic BˆO

Moment, D*

0.3 0.0 0.0 0.0 0.74 0.7 2.4 2.65 1.51 0.9 2.0 0.65 (0.2) 2.8 3.3 0.45 1.4 3.6 3.0 1.31 0.3 2.0 1.0 0.8 (0.3) 2.7 0.5 2.9 0.7 0.25

Bond Se ˆ C Si ˆ C Si ˆ H Si ˆ N H ˆ Sb G ˆ As HˆP HˆI H ˆ Br H ˆ Cl HˆF C ˆ Te NˆF PˆI P ˆ Br P ˆ Cl As ˆ I As ˆ Br As ˆ Cl As ˆ F Sb ˆ I Sb ˆ Br Sb ˆ Cl S ˆ Cl Cl ˆ O I ˆ Br I ˆ Cl Br ˆ Cl Br ˆ F Cl ˆ F Li ˆ C K ˆ Cl KˆF

Moment, D* 0.7 1.2 1.0 1.55 0.08 0.10 0.36 0.38 0.78 1.08 1.94 0.6 0.17 0.3 0.36 0.81 0.78 1.27 1.64 2.03 0.8 1.9 2.6 0.7 0.7 1.2 1 0.57 1.3 0.88 1.4 10.6 7.3

3.31

PROPERTIES OF ATOMS, RADICALS, AND BONDS

TABLE 3.6 Bond Dipole Moments (continued) Bond Cs ˆ Cl Cs ˆ F

Moment, D* 10.5 7.9

Dative (coordination) bonds NlB OlB SlB PlB NlO

2.6 3.6 3.8 4.4 4.3

Bond

Moment, D*

Dative (coordination) bonds (continued) PlO SlO As l O Se l O Te l O PlS P l Se Sb l S

2.9 3.0 4.2 3.1 2.3 3.1 3.2 4.5

*To convert debye units D into coulomb-meters, multiply by 3.33564  1030.

TABLE 3.7 Group Dipole Moments Moment, D* Group C ˆ CH3 C ˆ C2H5 C ˆ C(CH3)3 C ˆ CH ¨ CH2 C ˆ C ˜ CH CˆF C ˆ Cl C ˆ Br CˆI C ˆ CH2F C ˆ CF3 C ˆ CH2Cl C ˆ CHCl2 C ˆ CCl3 C ˆ CH2Br CˆC˜N C ˆ NC C ˆ CH2CN CˆC¨O C ˆ CHO C ˆ COOH C ˆ CO ˆ CH3 C ˆ CO ˆ OCH3 C ˆ CO ˆ OC2H5 C ˆ OH C ˆ OCH3 C ˆ OCF3

Aromatic C ˆ X

Aliphatic C ˆ X

0.37 0.37 0.5  0.4 0.7 1.47 1.59 1.57 1.40 1.77(g) 2.54 1.85 2.04 2.11 1.86 4.05 3.5 1.86 2.65 2.96 1.64 2.96 1.83 1.9 1.6 1.28 2.36

0.0 0.0 0.0 0.6 0.9 1.79 1.87 1.82 1.65 2.32 1.95 1.94 1.57 1.96 3.4 3.5 2.0 2.4 2.49 1.63 2.75 1.75 1.8 1.7 1.28

3.32

SECTION 3

TABLE 3.7 Group Dipole Moments (continued) Moment, D* Group C ˆ OCOCH3 C ˆ OC6H5 C ˆ CH2OH C ˆ NH2 C ˆ NHCH3 C ˆ N(CH3)2 C ˆ NHCOCH3 C ˆ N(C6H5)2 C ˆ NCO C ˆ N3 C ˆ NO C ˆ NO2 C ˆ CH2NO2 C ˆ SH C ˆ SCH3 C ˆ SCF3 C ˆ SCN C ˆ NCS C ˆ SC6H5 C ˆ SF5 C ˆ SOCF3 (C ˆ )2SO2 (C ˆ )2SO2CH3 (C ˆ )2SO2CF3 C ˆ SeH C ˆ SeCH3 C ˆ Si(CH3)3

Aromatic C ˆ X 1.69 1.16 1.68 1.53 1.71 1.58 3.69 (0.3) 2.32 1.44 3.09 4.01 3.3 1.22 1.34 2.50 3.59 2.9 1.51 3.4 3.88 5.05 4.73 4.32 1.08 1.31 0.44

*To convert debye units D into coulomb-meters, multiply by 3.33564  1030.

Aliphatic C ˆ X

1.16 1.68 1.46 0.86 0.3 2.8

2.70 3.4 1.55 1.40 3.6 3.3 1.5

4.53

1.32 0.4

SECTION 4

PHYSICAL PROPERTIES

SOLUBILITIES . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Table 4.1 Solubility of Gases in Water . . . . . . . . . . . . . . . VAPOR PRESSURES . . . . . . . . . . . . . . . . . . . . . . . . . . . . Table 4.2 Vapor Pressure of Mercury . . . . . . . . . . . . . . . . Table 4.3 Vapor Pressure of Water for temperatures from 10 to 12 C . . . . . . . . . . . . . . . . . . . . . . . Table 4.4 Vapor Pressure of Deuterium Oxide . . . . . . . . . . . BOILING POINTS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Table 4.5A Boiling Points for Common Organic . . . . . . . . . . . Solvents Arranged in order of increasing boiling point . Table 4.5B Boiling Points for Common Organic Solvents Arranged Alphabetically by Solvent Name . . . . . . . . Table 4.5C Boiling Point for Common Organic Solvents Arranged by Compound Type in Order of Increasing Boiling Point Table 4.6 Molecular Elevation of the Boiling Point . . . . . . . . . Table 4.7 Binary Azeotropic (Constant-boiling) Mixtures . . . . . Table 4.8 Ternary Azeotropic Mixtures . . . . . . . . . . . . . . . FREEZING POINTS . . . . . . . . . . . . . . . . . . . . . . . . . . . . Tables 4.9A and B Molecular Lowering of the Melting or Freezing Point . . VISCOSITY, DIELECTRIC CONSTANT, DIPOLE MOMENT, SURFACE TENSION, AND REFRACTIVE INDEX . . . . . . . . . . . Table 4.10 Viscosity, Dielectric Constant, Dipole Moment and Surface Tension of Selected Organic Substances . . . . . Table 4.11 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances . . Table 4.12 Refractive Index, Viscosity, Dielectric Constant, and Surface Tension of Water at Various Temperatures . COMBUSTIBLE MIXTURES . . . . . . . . . . . . . . . . . . . . . . . Table 4.13 Properties of Combustible Mixtures in Air . . . . . . . .

4.1

. . . .

. . . .

. . . .

. . . .

4.2 4.2 4.8 4.8

. . . . .

. . . . .

. . . . .

. . . . .

4.10 4.12 4.12 4.12 4.12

. . . .

4.15

. . . . .

. . . . .

4.17 4.23 4.25 4.46 4.52

. . . .

4.52

. . . .

4.55

. . . .

4.57

. . . .

4.94

. . . . . . . . . . . .

4.98 4.99 4.99

. . . . .

. . . . .

4.2

SECTION 4

SOLUBILITIES TABLE 4.1 Solubility of Gases in Water Explanation of the column headings , Volume of gas in milliliters (mL). The column or line entry headed “” gives the volume of gas (in milliliters) at standard conditions (0 C and 760 mm or 101.325 kN·m2) dissolved in 1 mL of water at the temperature stated (in degrees Celsius) and when the pressure of the gas without the water vapor is 760 mm. A, Volume of gas in milliliters (mL). The line entry “A” indicates the same quantity as “” except that the gas itself is at the uniform pressure of 760 mm when in equilibrium with water. l, Volume of gas in milliliters (mL). The column headed “l” gives the volume of the gas (in milliliters) dissolved in 1 mL of water when the pressure of the gas plus that of the water vapor is 760 mm. q, Weight of the gas in grams (g). The column headed “q” gives the weight of gas (in grams) dissolved in 100 g of water when the pressure of the gas plus that of the water vapor is 760 mm

Acetylene Temp. C 0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 35 40 45 50 60 70 80 90 100

Air*

Ammonia

Bromine



q

( 103)

% oxygen in air



q



q

1.73 1.68 1.63 1.58 1.53 1.49 1.45 1.41 1.37 1.34 1.31 1.27 1.24 1.21 1.18 1.15 1.13 1.10 1.08 1.05 1.03 1.01 0.99 0.97 0.95 0.93 0.91 0.89 0.87 0.85 0.84 — — — — — — — — —

0.200 0.194 0.188 0.182 0.176 0.171 0.167 0.162 0.157 0.154 0.150 0.146 0.142 0.138 0.135 0.131 0.129 0.125 0.123 0.119 0.117 0.115 0.112 0.110 0.107 0.105 0.102 0.100 0.098 0.095 0.094 — — — — — — — — —

29.18 28.42 27.69 26.99 26.32 25.68 25.06 24.47 23.90 23.36 22.84 22.34 21.87 21.41 20.97 20.55 20.14 19.75 19.38 19.02 18.68 18.34 18.01 17.69 17.38 17.08 16.79 16.50 16.21 15.92 15.64 — 14.18 — 12.97 12.16 — 11.26 — 11.05

34.91 34.87 34.82 34.78 34.74 34.69 34.65 34.60 34.56 34.52 34.47 34.43 34.38 34.34 34.30 34.25 34.21 34.17 34.12 34.08 34.03 33.99 33.95 33.90 33.86 33.82 33.77 33.73 33.68 33.64 33.60 — — — — — — — — —

1130 — — — 1047 — — — 947 — 870 — 857 837 — 770 775 — — — 680 — — — 639 — — — 586 — 530 — 400 — 290 200 — — — —

89.5 — — — 79.6 — — — 72.0 — 68.4 — 65.1 63.6 — — 58.7 — — — 52.9 — — — 48.2 — — — 44.0 — 41.0 — 31.6 — 23.5 16.8 11.1 6.5 3.0 0.0

60.5 — 54.1 — 48.3 — 43.3 — 38.9 — 35.1 — 31.5 — 28.4 — 25.7 — 23.4 — 21.3 — 19.4 — 17.7 — 16.3 — 15.0 — 13.8 — 9.4 — 6.5 4.9 3.8 3.0 — —

42.9 — 38.3 — 34.2 — 30.6 — 27.5 — 24.8 — 22.2 — 20.0 — 18.0 — 16.4 — 14.9 — 13.5 — 12.3 — 11.3 — 10.3 — 9.5 — 6.3 — 4.1 2.9 1.9 1.2 — —

*Free from NH3 and CO2; total pressure of air  water vapor is 760 mm.

TABLE 4.1 Solubility of Gases in Water (continued ) Carbon dioxide Temp. C



Carbon monoxide

q



q

Chlorine l

Ethane q

Ethylene



q



Hydrogen q



q

0 1 2 3 4

1.713 1.646 1.584 1.527 1.473

0.334 6 0.321 3 0.309 1 0.297 8 0.287 1

0.035 37 0.034 55 0.033 75 0.032 97 0.032 22

0.004 397 0.004 293 0.004 191 0.004 092 0.003 996

— — — — —

— — — — —

0.098 74 0.094 76 0.090 93 0.087 25 0.083 72

0.013 17 0.012 63 0.012 12 0.011 62 0.011 14

0.226 0.219 0.211 0.204 0.197

0.028 1 0.027 2 0.026 2 0.025 3 0.024 4

0.021 48 0.021 26 0.021 05 0.020 84 0.020 64

0.000 192 2 0.000 190 1 0.000 188 1 0.000 186 2 0.000 184 3

5 6 7 8 9

1.424 1.377 1.331 1.282 1.237

0.277 4 0.268 1 0.258 9 0.249 2 0.240 3

0.031 49 0.030 78 0.030 09 0.029 42 0.028 78

0.003 903 0.003 813 0.003 725 0.003 640 0.003 559

— — — — —

— — — — —

0.080 33 0.077 09 0.074 00 0.071 06 0.068 26

0.010 69 0.010 25 0.009 83 0.009 43 0.009 06

0.191 0.184 0.178 0.173 0.167

0.023 7 0.022 8 0.022 0 0.021 4 0.020 7

0.020 44 0.020 25 0.020 07 0.019 89 0.019 72

0.000 182 4 0.000 180 6 0.000 178 9 0.000 177 2 0.000 175 6

10 11 12 13 14

1.194 1.154 1.117 1.083 1.050

0.231 8 0.223 9 0.216 5 0.209 8 0.203 2

0.028 16 0.027 57 0.027 01 0.026 46 0.025 93

0.003 479 0.003 405 0.003 332 0.003 261 0.003 194

3.148 3.047 2.950 2.856 2.767

0.997 2 0.965 4 0.934 6 0.905 0 0.876 8

0.065 61 0.063 28 0.061 06 0.058 94 0.056 94

0.008 70 0.008 38 0.008 08 0.007 80 0.007 53

0.162 0.157 0.152 0.148 0.143

0.020 0 0.019 4 0.018 8 0.018 3 0.017 6

0.019 55 0.019 40 0.019 25 0.019 11 0.018 97

0.000 174 0 0.000 172 5 0.000 171 0 0.000 169 6 0.000 168 2

15 16 17 18 19

1.019 0.985 0.956 0.928 0.902

0.197 0 0.190 3 0.184 5 0.178 9 0.173 7

0.025 43 0.024 94 0.024 48 0.024 02 0.023 60

0.003 130 0.003 066 0.003 007 0.002 947 0.002 891

2.680 2.597 2.517 2.440 2.368

0.849 5 0.823 2 0.797 9 0.773 8 0.751 0

0.055 04 0.053 26 0.051 59 0.050 03 0.048 58

0.007 27 0.007 03 0.006 80 0.006 59 0.006 39

0.139 0.136 0.132 0.129 0.125

0.017 1 0.016 7 0.016 2 0.015 8 0.015 3

0.018 83 0.018 69 0.018 56 0.018 44 0.018 31

0.000 166 8 0.000 165 4 0.000 164 1 0.000 162 8 0.000 161 6

20 21 22 23 24

0.878 0.854 0.829 0.804 0.781

0.168 8 0.164 0 0.159 0 0.154 0 0.149 3

0.023 19 0.022 81 0.022 44 0.022 08 0.021 74

0.002 838 0.002 789 0.002 739 0.002 691 0.002 646

2.299 2.238 2.180 2.123 2.070

0.729 3 0.710 0 0.691 8 0.673 9 0.657 2

0.047 24 0.045 89 0.044 59 0.043 35 0.042 17

0.006 20 0.006 02 0.005 84 0.005 67 0.005 51

0.122 0.119 0.116 0.114 0.111

0.014 9 0.014 6 0.014 2 0.013 9 0.013 5

0.018 19 0.018 05 0.017 92 0.017 79 0.017 66

0.000 160 3 0.000 158 8 0.000 157 5 0.000 156 1 0.000 154 8

4.3

4.4 TABLE 4.1 Solubility of Gases in Water (continued ) Carbon dioxide Temp. C



Carbon monoxide

Chlorine

Ethane

Ethylene

q



q

l

q



q



Hydrogen q



q

25 26 27 28 29

0.759 0.738 0.718 0.699 0.682

0.144 9 0.140 6 0.136 6 0.132 7 0.129 2

0.021 42 0.021 10 0.020 80 0.020 51 0.020 24

0.002 603 0.002 560 0.002 519 0.002 479 0.002 442

2.019 1.970 1.923 1.880 1.839

0.641 3 0.625 9 0.611 2 0.597 5 0.584 7

0.041 04 0.039 97 0.038 95 0.037 99 0.037 09

0.005 35 0.005 20 0.005 06 0.004 93 0.004 80

0.108 0.106 0.104 0.102 0.100

0.013 1 0.012 9 0.012 6 0.012 3 0.012 1

0.017 54 0.017 42 0.017 31 0.017 20 0.017 09

0.000 153 5 0.000 152 2 0.000 150 9 0.000 149 6 0.000 148 4

30 35 40 45 50

0.665 0.592 0.530 0.479 0.436

0.125 7 0.110 5 0.097 3 0.086 0 0.076 1

0.019 98 0.018 77 0.017 75 0.016 90 0.016 15

0.002 405 0.002 231 0.002 075 0.001 933 0.001 797

1.799 1.602 1.438 1.322 1.225

0.572 3 0.510 4 0.459 0 0.422 8 0.392 5

0.036 24 0.032 30 0.029 15 0.026 60 0.024 59

0.004 68 0.004 12 0.003 66 0.003 27 0.002 94

0.098 — — — —

0.011 8 — — — —

0.016 99 0.016 66 0.016 44 0.016 24 0.016 08

0.000 147 4 0.000 142 5 0.000 138 4 0.000 134 1 0.000 128 7

60 70 80 90 100

0.359 — — — —

0.057 6 — — — —

0.014 88 0.014 40 0.014 30 0.014 2 0.014 1

0.001 522 0.001 276 0.000 980 0.000 57 0.000 00

1.023 0.862 0.683 0.39 0.00

0.329 5 0.279 3 0.222 7 0.127 0.000

0.021 77 0.019 48 0.018 26 0.017 6 0.017 2

0.002 39 0.001 85 0.001 34 0.000 8 0.000 0

— — — — —

— — — — —

0.016 00 0.016 0 0.016 0 0.016 0 0.016 0

0.000 117 8 0.000 102 0.000 079 0.000 046 0.000 000

TABLE 4.1 Solubility of Gases in Water (continued ) Hydrogen sulfide Temp. C

Methane

Nitric oxide

Nitrogen*

Oxygen

Sulfur dioxide



q



q



q



q



q

0 1 2 3 4

4.670 4.522 4.379 4.241 4.107

0.706 6 0.683 9 0.661 9 0.640 7 0.620 1

0.055 63 0.054 01 0.052 44 0.050 93 0.049 46

0.003 959 0.003 842 0.003 728 0.003 619 0.003 513

0.073 81 0.071 84 0.069 93 0.068 09 0.066 32

0.009 833 0.009 564 0.009 305 0.009 057 0.008 816

0.023 54 0.022 97 0.022 41 0.021 87 0.021 35

0.002 942 0.002 869 0.002 798 0.002 730 0.002 663

0.048 89 0.047 58 0.046 33 0.045 12 0.043 97

0.006 945 0.006 756 0.006 574 0.006 400 0.006 232

79.789 77.210 74.691 72.230 69.828

22.83 22.09 21.37 20.66 19.98

5 6 7 8 9

3.977 3.852 3.732 3.616 3.505

0.600 1 0.580 9 0.562 4 0.544 6 0.527 6

0.048 05 0.046 69 0.045 39 0.044 13 0.042 92

0.003 410 0.003 312 0.003 217 0.003 127 0.003 039

0.064 61 0.062 98 0.061 40 0.059 90 0.058 46

0.008 584 0.008 361 0.008 147 0.007 943 0.007 747

0.020 86 0.020 37 0.019 90 0.019 45 0.019 02

0.002 600 0.002 537 0.002 477 0.002 419 0.002 365

0.042 87 0.041 80 0.040 80 0.039 83 0.038 91

0.006 072 0.005 918 0.005 773 0.005 632 0.005 498

67.485 65.200 62.973 60.805 58.697

19.31 18.65 18.02 17.40 16.80

10 11 12 13 14

3.399 3.300 3.206 3.115 3.028

0.511 2 0.496 0 0.481 4 0.467 4 0.454 0

0.041 77 0.040 72 0.039 70 0.038 72 0.037 79

0.002 955 0.002 879 0.002 805 0.002 733 0.002 665

0.057 09 0.055 87 0.05470 0.053 57 0.052 50

0.007 560 0.007 393 0.007 233 0.007 078 0.006 930

0.018 61 0.018 23 0.017 86 0.017 50 0.017 17

0.002 312 0.002 263 0.002 216 0.002 170 0.002 126

0.038 02 0.037 18 0.036 37 0.035 59 0.034 86

0.005 368 0.005 246 0.005 128 0.005 014 0.004 906

56.647 54.655 52.723 50.849 49.033

16.21 15.64 15.09 14.56 14.04

15 16 17 18 19

2.945 2.865 2.789 2.717 2.647

0.441 1 0.428 7 0.416 9 0.405 6 0.394 8

0.036 90 0.036 06 0.035 25 0.034 48 0.033 76

0.002 599 0.002 538 0.002 478 0.002 422 0.002 369

0.051 47 0.050 49 0.049 56 0.048 68 0.047 85

0.006 788 0.006 652 0.006 524 0.006 400 0.006 283

0.016 85 0.016 54 0.016 25 0.014 97 0.015 70

0.002 085 0.002 045 0.002 006 0.001 970 0.001 935

0.034 15 0.033 48 0.032 83 0.032 20 0.031 61

0.004 802 0.004 703 0.004 606 0.004 514 0.004 426

47.276 45.578 43.939 42.360 40.838

13.54 13.05 12.59 12.14 11.70

l

q

4.5

4.6

TABLE 4.1 Solubility of Gases in Water (continued ) Hydrogen sulfide Temp. C

Methane

Nitric oxide

Nitrogen*

Oxygen

Sulfur dioxide



q



q



q



q

l

q



20 21 22 23 24

2.582 2.517 2.456 2.396 2.338

0.384 6 0.374 5 0.364 8 0.355 4 0.346 3

0.033 08 0.032 43 0.031 80 0.031 19 0.030 61

0.002 319 0.002 270 0.002 222 0.002 177 0.002 133

0.047 06 0.046 25 0.045 45 0.044 69 0.043 95

0.006 173 0.006 059 0.005 947 0.005 838 0.005 733

0.015 45 0.015 22 0.014 98 0.014 75 0.014 54

0.001 901 0.001 869 0.001 838 0.001 809 0.001 780

0 031 02 0.030 44 0.029 88 0.029 34 0.028 81

0.004 339 0.004 252 0.004 169 0.004 087 0.004 007

39.374 37.970 36.617 35.302 34.026

11.28 10.88 10.50 10.12 9.76

25 26 27 28 29

2.282 2.229 2.177 2.128 2.081

0.337 5 0.329 0 0.320 8 0.313 0 0.305 5

0.030 06 0.029 52 0.029 01 0.028 52 0.028 06

0.002 091 0.002 050 0.002 011 0.001 974 0.001 938

0.043 23 0.042 54 0.041 88 0.041 24 0.040 63

0.005 630 0.005 530 0.005 435 0.005 342 0.005 252

0.014 34 0.014 13 0.013 94 0.013 76 0.013 58

0.001 751 0.001 724 0.001 698 0.001 672 0.001 647

0.028 31 0.027 83 0.027 36 0.026 91 0.026 49

0.003 931 0.003 857 0.003 787 0.003 718 0.003 651

32.786 31.584 30.422 29.314 28.210

9.41 9.06 8.73 8.42 8.10

30 35 40 45 50

2.037 1.831 1.660 1.516 1.392

0.298 3 0.264 8 0.236 1 0.211 0 0.188 3

0.027 62 0.025 46 0.023 69 0.022 38 0.021 34

0.001 904 0.001 733 0.001 586 0.001 466 0.001 359

0.040 04 0 037 34 0.035 07 0.033 11 0.031 52

0.005 165 0.004 757 0.004 394 0.0040 59 0.003 758

0.013 42 0.012 56 0.011 84 0.011 30 0.010 88

0.001 624 0.001 501 0.001 391 0.001 300 0.001 216

0.026 08 0.024 40 0.023 06 0.021 87 0.020 90

0.003 588 0.003 315 0.003 082 0.002 858 0.002 657

27.161 22.489 18.766 — —

7.80 6.47 5.41 — —

60 70 80 90 100

1.190 1.022 0.917 0.84 0.81

0.148 0 0.1101 0.076 5 0.041 0.000

0.019 54 0.018 25 0.017 70 0.017 35 0.017 0

0.001 144 0.000 926 0.000 695 0.000 40 0.000 00

0.029 54 0.028 10 0.027 00 0.026 5 0.026 3

0.003 237 0.002 668 0.001 984 0.001 13 0.000 00

0.010 23 0.009 77 0.009 58 0.009 5 0.009 5

0.001 052 0.000 851 0.000 660 0.000 38 0.000 00

0.019 46 0.018 33 0.017 61 0.017 2 0.017 0

0.002 274 0.001 856 0.001 381 0.000 79 0.000 00

— — — — —

— — —

*Atmospheric nitrogen containing 98.815% N2 by volume  1.185% inert gases.

q

—

TABLE 4.1 Solubility of Gases in Water (continued) Substance Argon Helium Hydrogen bromide Hydrogen chloride Krypton Neon Nitrous oxide Ozone Radon Xenon

0  A l   A A g · L1  

0.052 8 0.009 8 612 512 0.110 5

0.039 4 0.510 0.242

10 0.041 3 0.009 11 582 475 0.081 0 0.011 79 0.88 0.029 912 0.326 0.174

20

30

40

0.033 7 0.008 6

0.028 8 0.008 39 53325 412 0.051 1 0.010 0

0.025 1 0.008 41 385 0.043 3 0.009 4842

0.013927 0.162 0.098

0.004 2 0.126 0.082

442 0.062 6 0.010 6 0.63 0.021 019 0.222 0.123

60 0.020 9 0.009 02 46950 339 0.035 7

80 0.018 4 0.0009 4270 40675

0.009 8473 0 0.085

4.7

4.8

SECTION 4

VAPOR PRESSURES TABLE 4.2 Vapor Pressure of Mercury Temp. C

mm of Hg

Temp. C

mm of Hg

0

0.000 185

78 80

0.078 89 0.088 80

2 4 6 8 10

0.000 228 0.000 276 0.000 335 0.000 406 0.000 490

82 84 86 88 90

0.100 0 0.112 4 0.126 1 0.141 3 0.1582

12 14 16 18 20

0.000 588 0.000 706 0.000 846 0.001 009 0.001 201

92 94 96 98 100

0.1769 0.1976 0.2202 0.2453 0.2729

22 24 26 28 30

0.001 426 0.001 691 0.002 000 0.002 359 0.002 777

32 34 36 38 40

0.003 261 0.003 823 0.004 471 0.005 219 0.006 079

102 104 106 108 110 112 114 116 118 120

0.3032 0.3366 0.3731 0.4132 0.4572 0.5052 0.5576 0.6150 0.6776 0.7457

42 44 46 48 50

0.007 067 0.008 200 0.009 497 0.010 98 0.012 67

122 124 126 128 130

0.8198 0.9004 0.9882 1.084 1.186

52 54 56 58 60

0.014 59 0.016 77 0.019 25 0.022 06 0.025 24

132 134 136 138 140

1.298 1.419 1.551 1.692 1.845

62 64 66 68 70

0.028 83 0.032 87 0.037 40 0.042 51 0.048 25

142 144 146 148 150

2.010 2.188 2.379 2.585 2.807

72 74 76

0.054 69 0.061 89 0.069 93

152 154 156

3.046 3.303 3.578

Temp. C

mm of Hg

158 160

3.873 4.189

162 164 166 168 170

4.528 4.890 5.277 5.689 6.128

172 174 176 178 180

6.596 7.095 7.626 8.193 8.796

182 184 186 188 190

9.436 10.116 10.839 11.607 12.423

192 194 196 198 200

13.287 14.203 15.173 16.200 17.287

202 204 206 208 210

18.437 19.652 20.936 22.292 23.723

212 214 216 218 220

25.233 26.826 28.504 30.271 32.133

222 224 226 228 230

34.092 36.153 38.318 40.595 42.989

4.9

PHYSICAL PROPERTIES

TABLE 4.2 Vapor Pressure of Mercury (continued) Temp. C

mm of Hg

Temp. C

mm of Hg

Temp. C

mm of Hg

232 234 236 238 240

45.503 48.141 50.909 53.812 56.855

302 304 306 308 310

257.78 269.17 280.98 293.21 305.89

372 374 376 378 380

994.34 1028.9 1064.4 1100.9 1138.4

242 244 246 248 250

60.044 63.384 66.882 70.543 74.375

312 314 316 318 320

319.02 332.62 346.70 361.26 376.33

382 384 386 388 390

1177.0 1216.6 1257.3 1299.1 1341.9

252 254 256 258 260

78.381 82.568 86.944 91.518 96.296

322 324 326 328 330

391.92 408.04 424.71 441.94 459.74

392 394 396 398 400

1386.1 1431.3 1477.7 1525.2 1574.1

262 264 266 268 270

101.28 106.48 111.91 117.57 123.47

332 334 336 338 340

478.13 497.12 516.74 537.00 557.90

430 460 490

2464 3715 5420

272 274 276 278 280

129.62 136.02 142.69 149.64 156.87

342 344 346 348 350

579.45 601.69 624.64 648.30 672.69

520 550 600 650 700

7691 10650 22.87 atm 35.49 atm 52.51 atm

282 284 286 288 290

164.39 172.21 180.34 188.79 197.57

352 354 356 358 360

697.83 723.73 750.43 777.92 806.23

750 800 850 900* 950

74.86 atm 103.31 atm 138.42 atm 180.92 atm 226.58 atm

292 294 296 298 300

206.70 216.17 226.00 236.21 246.80

362 364 366 368 370

835.38 865.36 896.23 928.02 960.66

1000 1050 1100 1150 1200 1250 1300

290.5 atm 358.1 atm 437.3 atm 521.3 atm 616.8 atm 721.4 atm 835.9 atm

*Critical point.

4.10

SECTION 4

TABLE 4.3 Vapor Pressure of Water for Temperatures from 10 to 120 C The values in the table are for water in contact with its own vapor. Where the water is in contact with air at a temperature t in degrees Celsius, the following correction must be added: Correction (when t  40 C)  p(0.775  0.000 313 t)/100; correction (when t  50 C)  p(0.0652  0.000 087 5 t)/100.

t, C 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0

p, mmHg

t, C

p, mmHg

t, C

p, mmHg

t, C

p, mmHg

2.149 2.236 2.326 2.418 2.514 2.613 2.715 2.822 2.931 3.046 3.163 3.284 3.410 3.540 3.673 3.813 3.956 4.105 4.258 4.416 4.579 4.750 4.926 5.107 5.294 5.486 5.685 5.889 6.101 6.318 6.543 6.775 7.013 7.259 7.513 7.775 8.045 8.323 8.609 8.905 9.209 9.521 9.844

11.5 12.0 12.5 13.0 13.5 14.0 14.5 15.0 15.2 15.4 15.6 15.8 16.0 16.2 16.4 16.6 16.8 17.0 17.2 17.4 17.6 17.8 18.0 18.2 18.4 18.6 18.8 19.0 19.2 19.4 19.6 19.8 20.0 20.2 20.4 20.6 20.8 21.0 21.2 21.4 21.6 21.8 22.0

10.176 10.518 10.870 11.231 11.604 11.987 12.382 12.788 12.953 13.121 13.290 13.461 13.634 13.809 13.987 14.166 13.347 14.530 14.715 14.903 15.092 15.284 15.477 15.673 15.871 16.071 16.272 16.477 16.685 16.894 17.105 17.319 17.535 17.753 17.974 18.197 18.422 18.650 18.880 19.113 19.349 19.587 19.827

22.2 22.4 22.6 22.8 23.0 23.2 23.4 23.6 23.8 24.0 24.2 24.4 24.6 24.8 25.0 25.2 25.4 25.6 25.8 26.0 26.2 26.4 26.6 26.8 27.0 27.2 27.4 27.6 27.8 28.0 28.2 28.4 28.6 28.8 29.0 29.2 29.4 29.6 29.8 30.0 30.2 30.4 30.6

20.070 20.316 20.565 20.815 21.068 21.324 21.583 21.845 22.110 22.387 22.648 22.922 23.198 23.476 23.756 24.039 24.326 24.617 24.912 25.209 25.509 25.812 26.117 26.426 26.739 27.055 27.374 27.696 28.021 28.349 28.680 29.015 29.354 29.697 30.043 30.392 30.745 31.102 31.461 31.824 32.191 32.561 32.934

30.8 31.0 31.2 31.4 31.6 31.8 32.0 32.2 32.4 32.6 32.8 33.0 33.2 33.4 33.6 33.8 34.0 34.2 34.4 34.6 34.8 35.0 35.2 35.4 35.6 35.8 36.0 36.2 36.4 36.6 36.8 37.0 37.2 37.4 37.6 37.8 38.0 38.2 38.4 38.6 38.8 39.0 39.2

33.312 33.695 34.082 34.471 34.864 35.261 35.663 36.068 36.477 36.891 37.308 37.729 38.155 38.584 39.018 39.457 39.898 40.344 40.796 41.251 41.710 42.175 42.644 43.117 43.595 44.078 44.563 45.054 45.549 46.050 46.556 47.067 47.582 48.102 48.627 49.157 49.692 50.231 50.774 51.323 51.879 52.442 53.009

4.11

PHYSICAL PROPERTIES

TABLE 4.3 Vapor Pressure of Water for Temperatures from 10 to 120 C (continued ) t, C

p, mmHg

t, C

p, mmHg

t, C

p, mmHg

t, C

p, mmHg

39.4 39.6 39.8 40.0 40.5 41.0 41.5 42.0 42.5 43.0 43.5 44.0 44.5 45.0 45.5 46.0 46.5 47.0 47.5 48.0 48.5 49.0 49.5 50.0 50.5 51.0 51.5 52.0 52.5 53.0 53.5 54.0 54.5 55.0 55.5 56.0 56.5 57.0 57.5 58.0

54.580 54.156 54.737 55.324 56.81 58 34 59.90 61.50 63.13 64.80 66.51 68.26 70.05 71.88 73.74 75.65 77.61 79.60 81.64 83.71 85.85 88.02 90.24 92.51 94.86 97.20 99.65 102.09 104.65 107.20 109.86 112.51 115.28 118.04 120.92 123.80 126.81 129.82 132.95 136.08

58.5 59.0 59.5 60.0 60 5 61.0 61.5 62.0 62.5 63.0 63.5 64.0 64.5 65.0 65.5 66.0 66.5 67.0 67.5 68.0 68.5 69.0 69.5 70.0 70.5 71.0 71.5 72.0 72.5 73.0 73.5 74.0 74.5 75.0 75.5 76.0 76.5 77.0 77.5 78.0

139.34 142.60 145.99 149.38 152.91 156.43 160.10 163.27 167.58 171.38 175.35 179.31 183.43 187.54 191.82 196.09 200.53 204.96 209.57 214.17 218.95 223.73 228.72 233.7 238.8 243.9 249.3 254.6 260.2 265.7 271.5 277.2 283.2 289.1 295.3 301.4 307.7 314.1 320.7 327.3

78.5 79.0 79.5 80.0 80.5 81.0 81.5 82.0 82.5 83.0 83.5 84.0 84.5 85.0 85.5 86.0 86.5 87.0 87.5 88.0 88.5 89.0 89.5 90.0 90.5 91.0 91.5 92.0 92.5 93.0 93.5 94.0 94.5 95.0 95.2 95.4 95.6 95.8 96.0 96.2

334.2 341.0 348.1 355.1 362.4 369.7 377.3 384.9 392.8 400.6 408.7 416.8 425.2 433.6 442.3 450.9 459.8 468.7 477.9 487.1 496.6 506.1 515.9 525.76 535.83 546.05 556.44 566.99 577.71 588.60 599.66 610.90 622.31 633.90 638.59 643.30 648.05 652.82 657.62 662.45

96.4 96.6 96.8 97 0 97.2 97.4 97.6 97.8 98.0 98.2 98.4 98.6 98.8 99.0 99.2 99.4 99.6 99.8 100.0 101.0 102.0 103.0 104.0 105.0 106.0 107.0 108.0 109.0 110.0 111.0 112.0 1130 114.0 115.0 116.0 117.0 118.0 119.0 120.0

667.31 672.20 677.12 682.07 687.04 692.05 697.10 702.17 707.27 712.40 717.56 722.75 727.98 733.24 738.53 743.85 749.20 754.58 760.00 787.57 815.86 845.12 875.06 906.07 937.92 970.60 1004.42 1038.92 1074.56 1111.20 1148.74 1187.42 1227.25 1267.98 1309.94 1352.95 1397.18 1442.63 1489.14

4.12

SECTION 4

TABLE 4.4 Vapor Pressure of Deuterium Oxide t, C

p, mmHg

t, C

p, mmHg

0 1 2 3 3.8 10

3.65 3.93 4.29 4.65 5.05 7.79

20 30 40 50 60 70

15.2 28.0 49.3 83.6 136.6 216.1

t, C

p, mmHg

80 90 100 101.43

331.6 495.5 722.2 760.0

BOILING POINTS TABLE 4.5A Boiling Points for Common Organic Solvents Arranged in order of increasing boiling point

Compound name Ethylene oxide Chloroethane Furan Methyl formate Diethyl ether Propylene oxide Pentane Bromoethane Dichloromethane Dimethoxyethane Carbon disulfide 1-Isopropoxy2-propanol Ethyl formate Acetone Methyl acetate 1,1-Dichloroethane Dichloroethylene Chloroform Methanol Tetrahydrofuran Diisopropyl ether Hexane 1-Chloro2-methylpropane 1,1,1-Trichloroethane 1,3-Dioxolane Carbon tetrachloride Ethyl acetate 1-Chlorobutane Ethanol 2-Butanone 2-Methyltetrahydrofuran

bp (C) 10.6 12.3 31.4 31.5 34.6 34.5 36.1 38.4 39.8 42.3 46.3 47.9 54.2 56.2 56.3 57.3 60.6 61.2 64.7 66.0 68.0 68.7 68.9

Other name Oxirane Ethyl chloride

Ethyl ether

Ethyl bromide Methylene chloride DME, glyme

Dimethyl ketone

THF Isopropyl ether Isobutyl chloride

74.0 74–75 76.7 77.1 77.9 Butyl chloride 78.3 79.6 Methyl ethyl ketone 80.0

Compound name Benzene Cyclohexane Propyl formate Acetonitrile 2-Propanol 1,1-Dimethylethanol Cyclohexene Diisopropyl amine 1,2-Dichloroethane Thiophene Trichloroethylene Isopropyl acetate 1-Bromo2-methylpropane 2,5-Dimethylfuran Ethyl chloroformate Allyl alcohol 1,2-Dichloropropane 1-Propanol Heptane 1-Chloro3-methylbutane Ethyl propanoate 2-Butanol Formic acid Methylcyclohexane 1,4-Dioxane Nitromethane Propyl acetate 2-Pentanone 3-Pentanone 2-Methyl-2-butanol 1,1-Diethoxyethane

bp (C) 80.1 80.7 80.9 81.6 82.4 82.4 83.0 83.5 83.7 84.2 87.2 88.2 91.5

Other name

Isopropyl alcohol t -Butanol

Isobutyl bromide

93–94 94.0 96.6 96.8 97.2 n-Propyl alcohol 98.4 99.0 99.1 Ethyl propionate 99.6 sec-Butanol 100.8 100.9 101.2 101.2 101.5 101.7 Methyl propyl ketone 102.0 Diethyl ketone 102.0 t-Pentanol 102.7

4.13

PHYSICAL PROPERTIES

TABLE 4.5A Boiling Points for Common Organic Solvents (continued ) Arranged in order of increasing boiling point

Compound name

bp (C)

Butyl formate 2-Methyl-1-propanol Toluene sec-Butyl acetate 1,1,2-Trichloroethane Nitroethane Pyridine 3-Pentanol 4-Methyl-2-pentanone

106.6 107.9 Isobutanol 110.6 Methylbenzene 112.3 113.5 114.1 115.2 115.6 115.7 Methyl isobutyl ketone 116.1 Epichlorohydrin

1-Chloro-2, 3-epoxypropane 1-Butanol 117.7 Acetic acid 117.9 Isobutyl acetate 118.0 2-Pentanol 119.3 1-Bromo3-methylbutane 119.7 1-Methoxy-2-propanol 120.1 2-Nitropropane 120.3 Tetrachloroethylene 121.1 Ethyl butanoate 121.6 3-Hexanone 123 2,4-Dimethyl124 3-pentanone 2-Methoxyethanol 124.6 Octane 125.7 Butyl acetate 126.1 Diethyl carbonate 126.8 2-Hexanone 127.2 1-Chloro-2-propanol 127.4 2-Chloroethanol 128.6 1-Nitropropane 131.2 Chlorobenzene 131.7 1,2-Dibromoethane 131.7 4-Methyl-2-pentanol 131.7 3-Methyl-1-butanol 132.0 Cyclohexylamine 134.8 2-Ethoxyethanol 134.8 Ethylbenzene 136.2 1-Pentanol 138 p-Xylene 138.4 m-Xylene Acetic anhydride 2,4-Pentanedione Isopentyl acetate Dibutyl ether

Other name

sec-Pentanol Isopentyl bromide Nitroisopropane Ethyl butyrate Ethyl propyl ketone Diisopropyl ketone

Methyl butyl ketone

Aminocyclohexane

1,4Dimethylbenzene 139.1 1,3Dimethylbenzene 140.0 140.6 Acetylacetone 142 142.4

Compound name 4-Heptanone o-Xylene 2-Methoxyethyl acetate 1,1,2, 2Tetrachloroethane 3-Heptanone Tribromomethane Nonane 2-Heptanone Isopropylbenzene N,N-Dimethylformamide Methoxybenzene Ethyl lactate Cyclohexanone Bromobenzene 1,2,3Trichloropropane 1-Hexanol Propylbenzene Cyclohexanol Bis(2-methoxyethyl) ether Isopentyl propanoate 2-Heptanol Pentachloroethane 2-Furaldehyde 2,6-Dimethyl4-heptanone

bp (C)

Other name

143.7 Dipropyl ketone 144.4 1,2Dimethylbenzene 144.5

146.3 147.8 Ethyl butyl ketone 149.6 Bromoform 150.8 151 Methyl pentyl ketone 152.4 Cumene 153.0 DMF 153.8 Anisole 154.5 155.7 156.2 156.9 157.5 159.2 161.1 160 Diglyme 160.2 Isopentyl propionate 160.4 160.5 161.8 Furfural

168.1 Diisobutyl ketone 4-Hydroxy-4-methyl- 169.2 2-pentanone 2-Furanmethanol 170.0 2-Hydroxy methylfuran Ethoxybenzene 170 Phenetole 2-Butoxyethanol 170.2 Butyl cellosolve Diisopentyl ether 173.4 Decane 174.2 1,3-Dichloro174.3 2-propanol Cyclohexyl acetate 174–175 1-Heptanol 175.8 Furfuryl acetate 175–177 4-Isopropyl177.1 p-Cymene 1-methylbenzene

4.14

SECTION 4

TABLE 4.5A Boiling Points for Common Organic Solvents (continued ) Arranged in order of increasing boiling point

Compound name

bp (C) Other name

Compound name

Isopentyl butanoate Bis(2-chloroethyl) ether 2-Octanol 1,2-Dichlorobenzene Ethyl acetoacetate Phenol 2-Ethyl-1-hexanol Aniline Benzyl ethyl ether Diethyl oxalate 1,2-Propanediol Bis(2-ethoxyethyl) ether Dimethylsulfoxide 1,2-Ethanediol diacetate Benzonitrile 2,5-Hexanedione 2-(2-Methoxyethoxy) ethanol N,N-Dimethylaniline

178.6 Isopentyl butyrate 178.8 Dichloro diethyl ether 179 180.4 o-Dichlorobenzene 180.8 181.8 Hydroxybenzene 184.3 184.4 Aminobenzene 185.0 185.4 188 Propylene glycol 188.4

o-Chloroaniline

1-Octanol 1,2-Ethanediol Diethyl malonate Methyl benzoate o-Toluidine p-Toluidine 2-(2-Ethoxyethoxy) ethanol Acetophenone 1,2-Dibutoxyethane 1,2-Phenylethanol m-Toluidine Benzyl alcohol Camphor

1,3-Butanediol 1,2,3,4-Tetrahydronaphthalene -Valerolactone

189.0 DMSO 190.2 Diacetoxyethane 191.0 Cyanobenzene 191.4 194.1 194.2 Dimethylaminobenzene 195.2 197.3 Ethylene glycol 199.3 199.5 200.4 1-Amino2-methylbenzene 200.6 1-Amino4-methylbenzene 202 202.1 Methyl phenylketone 203.6 203.9 Phenethyl alcohol 203.4 1-Amino3-methylbenzene 205.5 Hydroxymethylbenzene 207 1,7,7-Trimethylbicyclo[2.2.1] heptan-2-one 207.5 207.6 Tetralin 207– 208

bp (C) Other name

Nitrobenzene Ethyl benzoate Isophorone

Naphthalene 2-(2-Ethoxyethoxy) ethyl acetate Acetamide Methyl salicylate Diethyl maleate 1,4-Butanediol Propyl benzoate 1-Decanol Phenylacetonitrile Quinoline Tributyl borate Propylene carbonate 2-Phenoxyethanol Bis(2-hydroxyethyl) ether Dibutyl oxalate Butyl benzoate 1,2,3-Propanetriol triacetate 1-Chloronaphthalene Isopentyl benzoate trans-Ethyl cinnamate Bis (2-(2-methoxyethoxy)ethyl) ether 1-Methoxy2-nitrobenzene Isopentyl salicylate

208.8 1-Amino2-chlorobenzene 210.8 212.4 215.2 3,5, 5Trimethylcyclohex-2-en-1-one 217.7 218.5 221.2 223.0 225.3 230 231.2 230.2 233.5 Cyanomethylbenzene 237 238.5 240 240 245 Diethylene glycol 245.5 250 258– Glycerol 259 triacetate 259.3 262 271.0 275.3 Triglyme

277

277– 278 1-Bromonaphthalene 281.1 Dimethyl o -phthalate 283.7 1,2-Bis(carbomethoxy) benzene 2,2 -(Ethylenedioxy) bisethanol 285 Glycerol 290 Diethyl o-phthalate 295 Benzyl benzoate 323.5 Dibutyl o-phthalate 340.0 Dibutyl decanedioate 344–345

4.15

PHYSICAL PROPERTIES

TABLE 4.5B Boiling Points for Common Organic Solvents Arranged alphabetically by solvent name

Compound name Acetamide Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Allyl alcohol Aniline Benzene Benzonitrile Benzyl alcohol

bp (C)

Other name

221.2 117.9 140.0 56.2 Dimethyl ketone 81.6 202.1 Methyl phenyl ketone 96.6 184.4 Aminobenzene 80.1 191.0 Cyanobenzene 205.5 Hydroxymethylbenzene 323.5 185.0 275.3 Triglyme

Benzyl benzoate Benzyl ethyl ether Bis(2-(2-methoxyethoxy)ethyl) ether Bis(2-chloroethyl) ether Bis(2-ethoxyethyl) ether Bis(2-hydroxyethyl) ether Bis(2-methoxyethyl) ether Bromobenzene Bromoethane 1-Bromo2-methylpropane 1-Bromo3-methylbutane 1-Bromonaphthalene 1,3-Butanediol 1,4-Butanediol 1-Butanol 2-Butanol 2-Butanone 2-Butoxyethanol Butyl acetate sec-Butyl acetate Butyl benzoate Butyl formate Camphor

281.1 207.5 230 117.7 99.6 79.6 170.2 126.1 112.3 250 106.6 207

Carbon disulfide Carbon tetrachloride o-Chloroaniline

46.3 76.7 208.8

178.8 Dichloro diethyl ether 188.4 245

Diethylene glycol

160

Diglyme

156.2 38.4 Ethyl bromide 91.5 Isobutyl bromide 119.7 Isopentyl bromide

sec-Butanol Methyl ethyl ketone Butyl cellosolve

1,7,7-Trimethylbicyclo [2.2.1] heptan-2-one

1-Amino2-chlorobenzene

Compound name Chlorobenzene 1-Chlorobutane 1-Chloro-2, 3-epoxypropane 1-Chloro-2-propanol Chloroethane 2-Chloroethanol Chloroform 1-Chloro3-methylbutane 1-Chloro2-methylpropane 1-Chloronaphthalene Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclohexyl acetate

bp (C) 131.7 77.9 116.1 127.4 12.3 128.6 61.2 99.0 68.9

Other name

Butyl chloride Epichlorohydrin

Ethyl chloride

Isobutyl chloride

259.3 80.7 161.1 155.7 83.0 174– 175 Cyclohexylamine 134.8 Aminocyclohexane Decane 174.2 1-Decanol 230.2 1,2-Dibromoethane 131.7 1,2-Dibutoxyethane 203.6 Dibutyl decanedioate 344– 345 Dibutyl ether 142.4 Dibutyl o-phthalate 340.0 Dibutyl oxalate 245.5 1,2-Dichlorobenzene 180.4 o-Dichlorobenzene Dichloroethylene 60.6 Dichloromethane 39.8 Methylene chloride 1,1-Dichloroethane 57.3 1,2-Dichloroethane 83.7 1,2-Dichloropropane 96.8 1,3-Dichloro174.3 2-propanol 1,1-Diethoxyethane 102.7 Diethyl carbonate 126.8 Diethyl ether 34.6 Ethyl ether Diethyl maleate 225.3 Diethyl malonate 199.3 Diethyl o-phthalate 295 Diethyl oxalate 185.4 Diisopentyl ether 173.4 Diisopropyl amine 83.5 Diisopropyl ether 68.0 Isopropyl ether Dimethoxyethane 42.3 DME, glyme

4.16

SECTION 4

TABLE 4.5B Boiling Points for Common Organic Solvents (continued ) Arranged alphabetically by solvent name Compound name N,N-Dimethylaniline 1,1-Dimethylethanol N,N-Dimethylformamide 2,5-Dimethylfuran 2,6-Dimethyl4-heptanone 2,4-Dimethyl3-pentanone Dimethyl o-phthalate Dimethylsulfoxide 1,4-Dioxane 1,3-Dioxolane 1,2-Ethanediol 1,2-Ethanediol diacetate Ethoxybenzene 2-Ethoxyethanol 2-(2-Ethoxyethoxy) ethanol 2-(2-Ethoxyethoxy) ethyl acetate Ethyl acetate Ethyl acetoacetate Ethyl benzoate Ethyl butanoate Ethyl chloroformate trans-Ethyl cinnamate Ethyl formate Ethyl lactate Ethyl propanoate Ethylbenzene Ethylene oxide 2,2 -(Ethylenedioxy) bisethanol 2-Ethyl-1-hexanol Formic acid 2-Furaldehyde Furan 2-Furanmethanol Furfuryl acetate Glycerol Heptane 1-Heptanol 2-Heptanol

bp (C)

Other name

194.2 Dimethylaminobenzene 82.4 t-Butanol 153.0 DMF 93–94 168.1 Diisobutyl ketone 124 Diisopropyl ketone 283.7 1,2-Bis(carbomethoxy)benzene 189.0 DMSO 101.2 74–75 197.3 Ethylene glycol 190.2 Diacetoxyethane

Compound name 2-Heptanone

3-Heptanone 4-Heptanone Hexane 2,5-Hexanedione 1-Hexanol 2-Hexanone 3-Hexanone 4-Hydroxy-4-methyl2-pentanone Isobutyl acetate Isopentyl acetate Isopentyl benzoate Isopentyl butanoate Isopentyl propanoate Isopentyl salicylate

170 Phenetole 134.8 202 218.5 77.1 180.8 212.4 121.6 Ethyl butyrate 94.0 271.0 54.2 154.5 99.1 Ethyl propionate 136.2 10.6 Oxirane 285 184.3 100.8 161.8 Furfural 31.4 170.0 2-Hydroxymethylfuran 175– 177 290 98.4 175.8 160.4

bp (C)

Isophorone

Other name

151

Methyl pentyl ketone 147.8 Ethyl butyl ketone 143.7 Dipropyl ketone 68.7 191.4 157.5 127.2 Methyl butyl ketone 123 Ethyl propyl ketone 169.2 118.0 142 262 178.6 Isopentyl butyrate 160.2 Isopentyl propionate 277– 278 215.2 3,5,5-Trimethylcyclohex-2-en-1-one 88.2 152.4 Cumene 47.9

Isopropyl acetate Isopropylbenzene 1-Isopropoxy2-propanol 4-Isopropyl177.1 1-methylbenzene Methanol 64.7 Methoxybenzene 153.8 Methyl acetate 56.3 Methyl benzoate 199.5 Methyl formate 31.5 Methyl salicylate 223.0 Methylcyclohexane 100.9 1-Methoxy277 2-nitrobenzene 1-Methoxy-2-propanol 120.1 2-(2-Methoxyethoxy) 194.1 ethanol 2-Methoxyethanol 124.6 2-Methoxyethyl acetate144.5 2-Methyl-1-propanol 107.9 2-Methyl-2-butanol 102.0 2-Methyltetrahy80.0 drofuran 3-Methyl-1-butanol 132.0 4-Methyl-2-pentanol 131.7 4-Methyl-2-pentanone 115.7

p -Cymene

Anisole

Isobutanol t-Pentanol

Methyl isobutyl ketone

4.17

PHYSICAL PROPERTIES

TABLE 4.5B Boiling Points for Common Organic Solvents (continued ) Arranged alphabetically by solvent name Compound name

bp (C)

Naphthalene Nitrobenzene Nitroethane Nitromethane 1-Nitropropane 2-Nitropropane Nonane Octane 1-Octanol 2-Octanol Pentachloroethane Pentane 2,4-Pentanedione 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone

217.7 210.8 114.1 101.2 131.2 120.3 150.8 125.7 195.2 179 160.5 36.1 140.6 138 119.3 115.6 101.7

3-Pentanone Phenol 2-Phenoxyethanol Phenylacetonitrile

102.0 181.8 240 233.5

1-Phenylethanol 1,2-Propanediol 1,2,3-Propanetriol triacetate 1-Propanol 2-Propanol Propylene carbonate Propylene oxide Propyl acetate Propyl benzoate

203.9 188 258– 259 97.2 82.4 240 34.5 101.5 231.2

Other name

Compound name

Nitroisopropane

Propyl formate Propylbenzene Pyridine Quinoline 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrahydrofuran Thiophene Toluene o-Toluidine

Acetylacetone sec-Pentanol Methyl propyl ketone Diethyl ketone Hydroxybenzene Cyanomethylbenzene Phenethyl alcohol Propylene glycol Glycerol triacetate n-Propyl alcohol Isopropyl alcohol

bp (C)

Other name

80.9 159.2 115.2 237 146.3

121.1 66.0 THF 84.2 110.6 Methylbenzene 200.4 1-Amino2-methylbenzene m-Toluidine 203.4 1-Amino3-methylbenzene p-Toluidine 200.6 1-Amino4-methylbenzene Tribromomethane 149.6 Bromoform Tributyl borate 238.5 1,1,1-Trichloroethane 74.0 1,1,2-Trichloroethane 113.5 Trichloroethylene 87.2 1,2,3,4-Tetrahy207.6 Tetralin dronaphthalene 1,2,3-Trichloro 156.9 propane -Valerolactone 207– 208 o-Xylene 144.4 1,2-Dimethylbenzene m-Xylene 139.1 1,3-Dimethylbenzene p-Xylene 138.4 1,4-Dimethylbenzene

TABLE 4.5C Boiling Points for Common Organic Solvents Arranged by compound type in order of increasing boiling point Compound name acid acid alcohol alcohol alcohol alcohol alcohol alcohol

Formic acid Acetic acid 1-Isopropoxy-2-propanol Methanol Ethanol 2-Propanol 1,1-Dimethylethanol Allyl alcohol

(C) 100.8 117.9 47.9 64.7 78.3 82.4 82.4 96.6

Other name

Isopropyl alcohol t-Butanol

4.18

SECTION 4

TABLE 4.5C Boiling Points for Common Organic Solvents (continued ) Arranged by compound type in order of increasing boiling point Compound name alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol alcohol aldehyde amide amide amine amine

1-Propanol 2-Butanol 2-Methyl-2-butanol 2-Methyl-1-propanol 3-Pentanol 1-Butanol 2-Pentanol 1-Methoxy-2-propanol 2-Methoxyethanol 1-Chloro-2-propanol 2-Chloroethanol 4-Methyl-2-pentanol 3-Methyl-1-butanol 2-Ethoxyethanol 1-Pentanol 1-Hexanol Cyclohexanol 2-Heptanol 4-Hydroxy-4-methyl-2-pentanone 2-Furanmethanol 2-Butoxyethanol 1,3-Dichloro-2-propanol 1-Heptanol 2-Octanol Phenol 2-Ethyl-1-hexanol 1,2-Propanediol 2-(2-Methoxyethoxy) ethanol 1-Octanol 1,2-Ethanediol 2-(2-Ethoxyethoxy) ethanol 1-Phenylethanol Benzyl alcohol 1,3-Butanediol Methyl salicylate 1,4-Butanediol 1-Decanol 2-Phenoxyethanol Bis(2-hydroxyethyl) ether Isopentyl salicylate 2,2 -(Ethylenedioxy)bisethanol Glycerol 2-Furaldehyde N,N -Dimethylformamide Acetamide Diisopropylamine Pyridine

(C) 97.2 99.6 102.0 107.9 115.6 117.7 119.3 120.1 124.6 127.4 128.6 131.7 132.0 134.8 138 157.5 161.1 160.4 169.2 170.0 170.2 174.3 175.8 179 181.8 184.3 188 194.1 195.2 197.3 202 203.9 205.5 207.5 223.0 230 230.2 240 245 277–278 285 290 161.8 153.0 221.2 83.5 115.2

Other name n-Propyl alcohol sec-Butanol t-Pentanol Isobutanol

sec-Pentanol

2-Hydroxymethylfuran Butyl cellosolve

Hydroxybenzene Propylene glycol

Ethylene glycol Phenethyl alcohol Hydroxymethylbenzene

Diethylene glycol

Furfural DMF

4.19

PHYSICAL PROPERTIES

TABLE 4.5C Boiling Points for Common Organic Solvents (continued ) Arranged by compound type in order of increasing boiling point Compound name

(C)

amine amine amine amine

Cyclohexylamine Aniline N,N-Dimethylaniline o-Toluidine

134.8 184.4 194.2 200.4

amine

p-Toluidine

200.6

amine

m-Toluidine

203.4

amine amine anhydride bromide bromide bromide bromide bromide bromide bromide chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride chloride ester ester

o-Chloroaniline Quinoline Acetic anhydride Bromoethane 1-Bromo-2-methylpropane 1-Bromo-3-methylbutane 1,2-Dibromoethane Tribromomethane Bromobenzene 1-Bromonaphthalene Chloroethane Dichloromethane 1,1-Dichloroethane Dichloroethylene Chloroform 1-Chloro-2-methylpropane 1,1,1-Trichloroethane Carbon tetrachloride 1-Chlorobutane 1,2-Dichloroethane Trichloroethylene 1,2-Dichloropropane 1-Chloro-3-methylbutane 1,1,2-Trichloroethane 1-Chloro-2,3-epoxypropane Tetrachloroethylene 1-Chloro-2-propanol 2-Chloroethanol Chlorobenzene 1,1,2,2-Tetrachloroethane 1,2,3-Trichloropropane Pentachloroethane 1,3-Dichloro-2-propanol Bis(2-chloroethyl) ether 1,2-Dichlorobenzene o-Chloroaniline 1-Chloronaphthalene Methyl formate Ethyl formate

208.8 237 140.0 38.4 91.5 119.7 131.7 149.6 156.2 281.1 12.3 39.8 57.3 60.6 61.2 68.9 74.0 76.7 77.9 83.7 87.2 96.8 99.0 113.5 116.1 121.1 127.4 128.6 131.7 146.3 156.9 160.5 174.3 178.8 180.4 208.8 259.3 31.5 54.2

Other name Aminocyclohexane Aminobenzene Dimethylaminobenzene 1-Amino2-methylbenzene 1-Amino4-methylbenzene 1-Amino3-methylbenzene 1-Amino-2-chlorobenzene

Ethyl bromide Isobutyl bromide Isopentyl bromide Bromoform

Ethyl chloride Methylene chloride

Isobutyl chloride

Butyl chloride

Epichlorohydrin

Dichloro diethyl ether o-Dichlorobenzene 1-Amino-2-chlorobenzene

4.20

SECTION 4

TABLE 4.5C Boiling Points for Common Organic Solvents (continued ) Arranged by compound type in order of increasing boiling point Compound name

(C)

ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester ester

Methyl acetate Ethyl acetate Propyl formate Isopropyl acetate Methyl chloroformate Ethyl propanoate Propyl acetate Butyl formate sec-Butyl acetate Isobutyl acetate Ethyl butanoate Butyl acetate Diethyl carbonate Isopentyl acetate 2-Methoxyethyl acetate Ethyl lactate Isopentyl propanoate Cyclohexyl acetate Furfuryl acetate Isopentyl butanoate Ethyl acetoacetate Diethyl oxalate 1,2-Ethanediol diacetate Diethyl malonate Methyl benzoate -Valerolactone Ethyl benzoate 2-(2-Ethoxyethoxy)ethyl acetate Methyl salicylate Diethyl maleate Propyl benzoate Propylene carbonate Dibutyl oxalate Butyl benzoate 1,2,3-Propanetriol triacetate Isopentyl benzoate trans-Ethyl cinnamate Isopentyl salicylate Dimethyl o -phthalate

56.3 77.1 80.9 88.2 94.0 99.1 101.5 106.6 112.3 118.0 121.6 126.1 126.8 142 144.5 154.5 160.2 174–175 175–177 178.6 180.8 185.4 190.2 199.3 199.5 207–208 212.4 218.5 223.0 225.3 231.2 240 245.5 250 258–259 262 271.0 277–278 283.7

ester ester ester ester ether ether

Diethyl o -phthalate Benzyl benzoate Dibutyl o-phthalate Dibutyl decanedioate Ethylene oxide Furan

295 323.5 340.0 344–345 10.6 31.4

Other name

Ethyl propionate

Ethyl butyrate

Isopentyl propionate

Isopentyl butyrate

Diacetoxyethane

Glycerol triacetate

1,2-Bis(carbomethoxy) benzene

Oxirane

4.21

PHYSICAL PROPERTIES

TABLE 4.5C Boiling Points for Common Organic Solvents (continued ) Arranged by compound type in order of increasing boiling point Compound name ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether ether hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon

Diethyl ether Propylene oxide Dimethoxyethane 1-Isopropoxy-2-propanol Tetrahydrofuran Diisopropyl ether 1,3-Dioxolane 2-Methyltetrahydrofuran 2,5-Dimethylfuran 1,4-Dioxane 1,1-Diethoxyethane 1-Chloro-2,3-epoxypropane 1-Methoxy-2-propanol 2-Methoxyethanol 2-Ethoxyethanol Dibutyl ether 2-Methoxyethyl acetate Methoxybenzene Bis(2-methoxyethyl) ether 2-Furanmethanol Ethoxybenzene 2-Buroxyethanol Diisopentyl ether Bis(2-chloroethyl) ether Benzyl ethyl ether Bis(2-ethoxyethyl)ether 2-(2Methoxyethoxy)ethanol 2-(2-Ethoxyethoxy) ethanol 1,2 Dibutoxyethane 2-(2-Ethoxyethoxy)ethyl acetate 2-Phenoxyethanol Bis(2-hydroxyethyl) ether Bis(2-(2-methoxyethoxy)ethyl) ether 1-Methoxy-2-nitrobenzene 2,2 -(Ethylenedioxy) bisethanol Pentane Hexane Benzene Cyclohexane Cyclohexene Heptane Methylcyclohexane Toluene Octane Ethylbenzene p -Xylene m -Xylene

(C) 34.6 34.5 42.3 47.9 66.0 68.0 74–75 80.0 93–94 101.2 102.7 116.1 120.1 124.6 134.8 142.4 144.5 153.8 160 170.0 170 170.2 173.4 178.8 185.0 188.4 194.1 202 203.6 218.5 240 245 275.3 277 285 36.1 68.7 80.1 80.7 83.0 98.4 100.9 110.6 125.7 136.2 138.4 139.1

Other name Ethyl ether DME, glyme THF Isopropyl ether

Epichlorohydrin

Anisole Diglyme 2-Hydroxymethylfuran Phenetole Butyl cellosolve Dichloro diethyl ether

Diethylene glycol Triglyme

Methylbenzene

1,4-Dimethylbenzene 1,3-Dimethylbenzene

4.22

SECTION 4

TABLE 4.5C Boiling Points for Common Organic Solvents (continued ) Arranged by compound type in order of increasing boiling point Compound name

(C)

hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone ketone

o-Xylene Nonane Isopropylbenzene Propylbenzene Decane 4-Isopropyl-l-methylbenzene 1,2,3,4-Tetrahydronaphthalene Naphthalene Acetone 2-Butanone 2-Pentanone 3-Pentanone 4-Methyl-2-pentanone 3-Hexanone 2,4-Dimethyl-3-pentanone 2-Hexanone 2,4-Pentanedione 4-Heptanone 3-Heptanone 2-Heptanone Cyclohexanone 2,6-Dimethyl-4-heptanone 4-Hydroxy-4-methyl-2-pentanone 2,5-Hexanedione Acetophenone Camphor

144.4 150.8 152.4 159.2 174.2 177.1 207.6 217.7 56.2 79.6 101.7 102.0 115.7 123 124 127.2 140.6 143.7 147.8 151 155.7 168.1 169.2 191.4 202.1 207

ketone

Isophorone

215.2

miscellaneous miscellaneous nitrile nitrile nitrile nitro compound nitro compound nitro compound nitro compound nitro compound nitro compound sulfide sulfoxide

Carbon disulfide Tributyl borate Acetonitrile Benzonitrile Phenylacetonitrile Nitromethane Nitroethane 2-Nitropropane 1-Nitropropane Nitrobenzene 1-Methoxy-2-nitrobenzene Thiophene Dimethylsulfoxide

46.3 238.5 81.6 191.0 233.5 101.2 114.1 120.3 131.2 210.8 277 84.2 189.0

Other name 1,2-Dimethylbenzene Cumene

p-Cymene Tetralin Dimethyl ketone Methyl ethyl ketone Methyl propyl ketone Diethyl ketone Methyl isobutyl ketone Ethyl propyl ketone Diisopropyl ketone Methyl butyl ketone Acetylacetone Dipropyl ketone Ethyl butyl ketone Methyl pentyl ketone Diisobutyl ketone

Methyl phenyl ketone 1,7,7-Trimethylbicyclo[2.2.1] heptan-2-one 3,5,5-Trimethylcyclohex-2-en-1-one

Cyanobenzene Cyanomethylbenzene

Nitroisopropane

DMSO

4.23

PHYSICAL PROPERTIES

TABLE 4.6 Molecular Elevation of the Boiling Point Ebullioscopic constants Molecular weights can be determined with the relation M  Kb

1000 w2 w1 Tb

where Tb is the elevation of the boiling point brought about by the addition of w2 grams of solute to w1 grams of solvent and Kb is the ebullioscopic constant. In the column headed “Barometric correction” is given the number of degrees for each millimeter of difference between the barometric reading and 760 mmHg to be subtracted from Kb if the pressure is lower, or added if higher, than 760 mm. In general, the effect is within experimental error if the pressure is within 10 mm of 760 mm.

Compound Acetic acid Acetic anhydride Acetone Acetonitrile Acetophenone Aniline Benzene Benzonitrile Bromobenzene Bromoethane 2-Butanone cis-2-Butene-1,4-diol D-()-Camphor Carbon disulfide Carbon tetrachloride Chlorobenzene Chloroethane Chloroform Cyclohexane 1,2-Dibromoethane 1,1-Dichloroethane 1,2-Dichloroethane Dichloromethane Diethyl ether Diethyl sulfide Dimethoxymethane N,N-Dimethylacetamide Dimethyl sulfide 1,4-Dioxane Ethanol Ethoxybenzene Ethyl acetate Formic acid Glycerol Heptane Hexane 2-Hydroxybenzaldehyde

Barometric correction 0.000 8 0.000 4

0.000 9 0.000 7 0.001 6

0.001 5 0.000 6 0.001 3 0.001 1 0.000 9 0.000 7 0.001 6

0.000 5

0.000 3 0.000 7

0.000 8

Kb 3.07 3.53 1.71 1.30 5.65 3.52 2.53 3.87 6.26 2.53 2.28 2.86 5.611 2.34 5.03 4.15 1.95 3.63 2.79 6.608 3.13 3.44 2.60 2.02 3.23 2.125 3.22 1.85 3.270 1.22 5.0 2.77 2.4 6.52 3.43 2.75 4.96

4.24

SECTION 4

TABLE 4.6 Molecular Elevation of the Boiling Point (continued )

Compound Iodoethane Iodomethane 4-Isopropyl-1-methylbenzene Methanol Methoxybenzene Methyl acetate 2-Methyl-2-butanol 3-Methyl-1-butanol 3-Methylbutyl acetate Methyl formate 2-Methyl-1-propanol 2-Methyl-2-propanol Naphthalene Nitrobenzene Nitroethane Nitromethane Octane Pentyl acetate Phenol Piperidine 1-Propanol Propionic acid Propionitrile Pyridine Quinoline 1,1,2,2-Tetrachloroethylene 1,2,3,4-Tetrahydronaphthalene Toluene p-Toluidine Trichloroethylene 1,1,2-Trichloro-1,2,2-trifluoroethane Triethylamine Water

Barometric correction

0.000 2 0.000 5

0.001 4

0.000 9

0.000 8

0.000 1

Kb 5.16 4.19 5.52 0.83 4.502 2.15 2.255 2.65 4.83 1.649 2.166 1.745 5.80 5.24 2.60 1.86 4.02 4.83 3.60 2.84 1.59 3.51 1.87 2.710 5.84 5.50 5.582 3.33 4.14 4.43 5.75 3.45 0.512

Distillation is an important historical method for the separation of liquids. A mixture or solution of two liquids is heated until the vapor pressure of the lower boiling compound reaches the pressure of the surroundings. This may be ambient pressure or a lowered pressure caused by application of a vacuum. In either event, vaporization occurs, the vapors are condensed on a cold surface, and the condensed liquid is collected. If the boiling points of the two liquids are sufficiently different given the pressure and efficiency of the apparatus, separation may be achieved. A zeotrope is a mixture that can be separated by distillation. In contrast, certain mixtures of two (binary) or three (ternary) components form constant boiling mixtures that cannot be separated by distillation. In such cases, each component contributes a fixed amount and the boiling point of the mixture is characteristic of the components. Such a system is called an azeotrope. The boiling point of an azeotrope may be higher or lower than that of the individual components. Common binary azeotropes are listed in Table 4.7 and ternary azeotropes are listed in Table 4.8.

4.25

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures A zeotrope is a mixture that can be separated by distillation. A. Binary azeotropes containing water Composition, wt % System

BP of azeotrope, C

Water

Other component

Inorganic acids Hydrogen bromide Hydrogen chloride Hydrogen fluoride Hydrogen iodide Hydrogen peroxide Nitric acid Perchloric acid

126 108.58 111.35 127 zeotrope 120.7 203

52.5 79.78 64.4 43

47.5 20.22 35.6 57

32.6 28.4

67.4 71.6

22.6

77.4

82.3 79 81.6 89 81.6 71 97.8

17.7 21 18.4 11 18.4 29 2.2

4 27.7 71.7 12.6 42.5 26.8 11.7 54.4 36.5 36.0 27.5 67.2 90 58 83 90.8 87.5

96 72.3 28.3 87.4 57.5 73.2 88.3 45.6 63.5 64.0 72.5 32.8 10 42 17 9.2 12.5

Organic acids Formic acid Acetic acid Propionic acid Isobutyric acid Butyric acid Pentanoic acid Isopentanoic acid Perfluorobutyric acid Crotonic acid

107.2 zeotrope 99.9 99.3 99.4 99.8 99.5 97 99.9 Alcohols

Ethanol Allyl alcohol 1-Propanol 2-Propanol 1-Butanol 2-Butanol 2-Methyl-2-propanol 1-Pentanol 2-Pentanol 3-Pentanol 2,2-Dimethyl-2-propanol 1-Hexanol 1-Octanol Cyclopentanol 1-Heptanol Phenol 2-Methoxyphenol

78.17 88.9 71.7 80.3 92.7 87.0 79.9 95.8 91.7 91.7 87.35 97.8 99.4 96.25 98.7 99.52 99.5

4.26

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Water

Other component

Alcohols (continued ) 1-Phenylphenol Benzyl alcohol 2,3-Dimethyl-2, 3-butanediol Furfuryl alcohol

99.95 99.9

98.75 91

1.25 9

zeotrope 98.5

80

20

2 6 19 28.5 65

98 94 81 71.5 35

82.7 99 92.8 93.6 93.5 97 97.35 96.02 97 99.8 95 99.65 98.6 99.2

15 74 35 41.3 48 60 62.8 51.8 50.5 92.8 38 79.7 80.8 83.9

85 26 65 58.7 52 40 37.2 48.2 49.5 7.2 62 20.3 19.2 16.1

99.85

97.5

2.5

2.8 2.8 17 17.2 8.3 2.2 12 28.4

97.2 97.2 83 82.8 91.7 97.8 88 71.6

Aldehydes Propionaldehyde Butyraldehyde Pentanal Paraldehyde Furaldehyde

47.5 68 83 90 97.5 Amines

N-Methylbutylamine Furfurylamine Piperidine Pyridine 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2,6-Dimethylpyridine Dibutylamine Dihexylamine Triallylamine Tributylamine Aniline N-Ethylaniline 1-Methyl-2-(2-pyridyl) pyrrolidine

Halogenated hydrocarbons Chloroform Carbon tetrachloride Trichloroethylene Tetrachloroethylene 1,2-Dichloroethane 1-Chloropropane 1,2-Dichloropropane Chlorobenzene

56.1 42.6 73.4 88.5 72 44 78 90.2

4.27

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Water

Other component

5 3 2.3 7.8 14.5 21 28.4 80 8.47 14.7 10.6 16.5 14 28.7 36.3 41 61 75.1 87.5 3.9 10 19.9 23 52.2 48.5 11.5 21.5 36.4 46 53 63.5 6.8 15.2 30.8 39.4 56.0 19.2 30.2 45.2 55.8 74.1

95 97 97.7 92.2 85.5 79 71.6 20 91.53 85.3 89.4 83.5 86 71.3 63.7 59 39 24.9 12.5 96.1 90 80.1 77 47.8 51.5 88.5 78.5 63.6 54 47 36.5 93.2 84.8 69.2 60.6 44.0 80.8 69.8 54.8 44.2 25.9

Esters Ethyl formate Isopropyl formate Propyl formate Isobutyl formate Butyl formate Isopentyl formate Pentyl formate Benzyl formate Ethyl acetate Allyl acetate Isopropyl acetate Propyl acetate Isobutyl acetate Butyl acetate Isopentyl acetate Pentyl acetate Hexyl acetate Phenyl acetate Benzyl acetate Methyl propionate Ethyl propionate Isopropyl propionate Propyl propionate Isobutyl propionate Isopentyl propionate Methyl butyrate Ethyl butyrate Propyl butyrate Isobutyl butyrate Butyl butyrate Isopentyl butyrate Methyl isobutyrate Ethyl isobutyrate Propyl isobutyrate Isobutyl isobutyrate Isopentyl isobutyrate Methyl isopentanoate Ethyl isopentanoate Propyl isopentanoate Isobutyl isopentanoate Isopentyl isopentanoate

52.6 65.0 71.6 80.4 83.8 90.2 91.6 99.2 70.38 83 76.6 87.4 82.4 90.2 93.8 95.2 97.4 98.9 99.6 71.4 81.2 85.2 88.9 92.75 96.55 82.7 87.9 94.1 96.3 97.2 98.05 77.7 85.2 92.2 95.5 97.4 87.2 92.2 96.2 97.4 98.8

4.28

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant-Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Water

Other component

40 54 79.2 84.0 90.9 94 95.6 91.3 95.5 97.5 98.0 45.1 75.5 7.2 74 38 80 84.6 22 20 25 73

60 46 20.8 16.0 9.1 6 4.4 8.7 4.5 2.5 2.0 54.9 24.5 92.8 26 62 20 15.4 78 80 75 27

1.5 1.3 4 4.5 11.9 23 33 54 14.5 96.75 40.5

98.5 98.7 96 95.5 88.1 77 67 46 85.5 3.25 59.5

1.4 5.6 12.9 11.1

98.6 94.4 87.1 88.9

Esters (continued) Ethyl pentanoate Ethyl hexanoate Methyl benzoate Ethyl benzoate Propyl benzoate Butyl benzoate Isopentyl benzoate Ethyl phenylacetate Methyl cinnamate Methyl phthalate Diethyl o-phthalate Ethyl chloroacetate Butyl chloroacetate Methyl acrylate Isobutyl carbonate Ethyl crotonate Methyl lactate 1,2-Ethanediol diacetate Ethyl nitrate Propyl nitrate Isobutyl nitrate Methyl sulfate

94.5 97.2 99.08 99.4 99.7 99.9 99.9 99.7 99.9 99.95 99.98 95.2 98.12 71 98.6 93.5 99 99.7 74.35 84.8 89.0 98.6 Ethers

Ethyl vinyl ether Diethyl ether Ethyl propyl ether Diisopropyl ether Butyl ethyl ether Diisobutyl ether Dibutyl ether Diisopentyl ether 1,1-Diethoxyethane Diphenyl ether Methoxybenzene

34.6 34.2 59.5 62.2 76.6 88.6 92.9 97.4 82.6 99.33 95.5 Hydrocarbons

Pentane Hexane Heptane 2,2,4-Trimethylpentane

34.6 61.6 79.2 78.8

4.29

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Water

Other component

Hydrocarbons (continued ) Nonane Undecane Dodecane Acrolein Cyclohexene Cyclohexane 1-Octene Benzene Toluene Ethylbenzene m-Xylene Isopropylbenzene Naphthalene

94.8 98.85 99.45 52.4 70.8 69.5 88.0 69.25 84.1 92.0 92 95 98.8

82 96.0 98 2.6 8.93 8.4 28.7 8.83 13.5 33.0 35.8 43.8 84

18 4.0 2 97.4 91.07 91.6 71.3 91.17 86.5 67.0 64.2 56.2 16

zeotrope 73.5 83.3 94.6 87.9 95 94.6 94.3

11 19.5 42.4 24.3 48 42.2 40.5

89 80.5 57.6 75.7 52 57.8 59.5

98.8 91.8

87.3 34.8

12.7 65.2

16.3 23 32.5 14.3

83.7 77 67.5 85.7

32.3

67.7

23.6 28.5 11.7 30 2.8

76.4 71.5 88.3 70 97.2

Ketones Acetone 2-Butanone 2-Pentanone Cyclopentanone 4-Methyl-2-pentanone 2-Heptanone 3-Heptanone 4-Heptanone 4-Hydroxy-4-methyl-2pentanone 4-Methyl-3-penten-2-one

Nitriles Acetonitrile Isobutyronitrile Butyronitrile Acrylonitrile

76.5 82.5 88.7 70.6 Miscellaneous

Hydrazine Acetamide Nitromethane Nitroethane 2,5-Dimethylfuran Trioxane Carbon disulfide

120 zeotrope 83.59 87.22 77.0 91.4 42.6

4.30

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant-Boiling) Mixtures (continued ) B. Binary azeotropes containing organic acids Composition, wt % System

BP of azeotrope, C

Acid

Other component

4 20 28 29 70 46.5 56.5 63 31 50 74 71.8 73 6 15 18.5 25 50 3 51.5 14 27 14 8 1.5 19 68 59 27 83 61.4 25 32 33 45.5 35 62 83 17

96 80 72 71 30 53.5 43.5 37 69 50 26 28.2 27 94 85 81.5 75 50 97 48.5 86 73 86 92 98.5 81 32 41 73 17 38.6 75 68 67 54.5 65 38 17 83

Formic acid 2-Methylbutane Pentane Hexane Methylcyclopentane Cyclohexane Methylcyclohexane Heptane Octane Benzene Toluene o-Xylene m-Xylene Styrene Iodomethane Chloroform Carbon tetrachloride Trichloroethylene Tetrachloroethylene Bromoethane 1,2-Dibromoethane 1,2-Dichloroethane 1-Bromopropane 2-Bromopropane 1-Chloropropane 2-Chloropropane 1-Chloro-2-methylpropane Bromobenzene Chlorobenzene Fluorobenzene o-Chlorotoluene Pyridine 2-Methylpyridine 2-Pentanone 3-Pentanone Nitromethane Diethyl sulfide Diisopropyl sulfide Dipropyl sulfide Carbon disulfide

27.2 34.2 60.6 63.3 70.7 80.2 78.2 90.5 71.05 85.8 95.5 92.8 97.8 42.1 59.15 66.65 74.1 88.2 38.2 94.7 77.4 64.7 77.4 45.6 34.7 63.0 98.1 93.7 73.0 100.2 127.43 158.0 105.3 105.4 97.07 82.2 93.5 98.0 42.55

4.31

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Acid

Other component

Acetic acid Hexane Heptane Octane Nonane Decane Undecane Cyclohexane Methylcyclohexane Benzene Toluene o-Xylene m-Xylene p-Xylene Ethylbenzene Styrene Isopropylbenzene Triethylamine Nitromethane Nitroethane Pyridine 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2,6-Dimethylpyridine Carbon tetrachloride Trichloroethylene Tetrachloroethylene 1,2-Dibromoethane 2-Iodopropane 1-Bromobutane 1-Bromo-2-methylpropane Chlorobenzene Trichloronitromethane 1,4-Dioxane Diisopropyl sulfide

68.3 91.7 105.7 112.9 116.75 117.9 78.8 96.3 80.05 100.6 116.6 115.35 115.25 114.65 116.8 116.0 163 101.2 112.4 138.1 144.1 152.5 154.3 148.1 76 86.5 107.4 114.4 88.3 97.6 90.2 114.7 107.65 119.5 111.5

6.0 23 53.7 69 79.5 95 9.6 31 2.0 28.1 78 72.5 72 66 85.7 84 67 96 30 51.1 40.4 30.4 30.3 22.9 98.46 96.2 61.5 55 9 18 12 58.5 80.5 77 48

94.0 67 46.3 31 20.5 5 90.4 69 98.0 71.9 22 27.5 28 34 14.3 16 33 4 70 48.9 59.6 69.6 69.7 77.1 1.54 3.8 38.5 45 91 82 88 41.5 19.5 23 52

2 21.5

98 78.5

Propanoic (Propionic) acid Heptane Octane

97.8 120.9

4.32

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Acid

Other component

54.0 80.5 43 34 77 65 75 65 58.5 96 67.2 55.0 17.5 9 18 45

46.0 19.5 57 66 23 35 25 35 41.5 4 32.8 45.0 82.5 91 82 55

84.4 10 6 5.5 4 15 45 38 20 28 75

15.5 90 94 94.5 96 85 55 62 80 72 25

84 2.8 12 92.0 42.5 3.5 2.5 2.8 57 72 79.5 75 65 84 40

16 97.2 88 8.0 57.5 96.5 97.5 97.2 43 28 20.5 25 35 16 60

Acetic acid (continued) Nonane Decane o-Xylene p-Xylene 1,3,5-Trimethylbenzene Isopropylbenzene Propylbenzene Camphene -Pinene Methoxybenzene Pyridine 2-Methylpyridine 1,2-Dibromoethane 1-Iodo-2-methylpropane Chlorobenzene Dipropyl sulfide

134.3 139.8 135.4 132.5 139.3 139.0 139.5 138.0 136.4 140.8 148.6 154.5 127.8 119.5 128.9 136.5 Butyric (butanoic) acid

Undecane o-Xylene m-Xylene p-Xylene Ethylbenzene Styrene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Isopropylbenzene Propylbenzene Butylbenzene Naphthalene Indene Camphene Methoxybenzene Pyridine 2-Furaldehyde 1,2-Dibromoethane 1-Iodobutane Chlorobenzene 1,4-Dichlorobenzene o-Bromotoluene m-Bromotoluene p-Bromotoluene -Chlorotoluene Ethyl bromoacetate Propyl chloroacetate

162.4 143.0 138.5 137.8 135.8 143.5 159.5 158.0 149.5 154.5 162.5 zeotrope 163.7 152.3 152.9 163.2 159.4 131.1 129.8 131.75 162.0 163.0 163.6 161.5 160.8 157.4 160.5

4.33

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt% System

BP of azeotrope, C

Acid

Other component

Isobutyric (2-methylpropanoic) acid 2,7-Dimethyloctane o-Xylene m-Xylene p-Xylene Styrene 1,2,4-Trimethylbenzene Isopropylbenzene Propylbenzene Camphene D-Limonene Methoxybenzene Ethyl bromoacetate Ethyl 2-oxopropionate 1,2-Dibromoethane 1-Iodobutane 1-Bromohexane Bromobenzene Chlorobenzene o-Bromotoluene -Chlorotoluene Diisopentyl ether Ethyl bromoacetate

148.6 141.0 139.9 136.4 142.0 152.3 146.8 149.3 148.1 152.5 149.0 153.0 153.0 130.5 128.8 148.0 148.6 131.5 153.9 153.5 154.2 153.0

48 22 15 13 27 63 35 49 45 78 42 40 60 6.5 7 35 35 8 85 80 93 40

52 78 85 87 73 37 65 51 55 22 58 60 40 93.5 93 65 65 92 15 20 7 60

C. Binary azeotropes containing alcohol Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

Methanol Pentane Cyclopentane Cyclohexane Methylcyclohexane Heptane Octane Nonane Benzene Fluorobenzene Toluene Bromomethane Iodomethane

30.9 38.8 53.9 59.2 59.1 62.8 64.1 57.5 59.7 63.5 3.55 37.8

7 14 36.4 54 51.5 67.5 83.4 39.1 32 72.5 99.55 95.5

93 86 63.6 46 48.5 32.5 16.6 60.9 68 27.5 0.45 4.5

4.34

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

Methanol (continued ) Bromodichloromethane Chloroform Carbon tetrachloride Bromoethane 1,2-Dichloroethane Trichloroethylene 1-Bromopropane 2-Bromopropane 1-Chloropropane 2-Chloropropane 2-Iodopropane 1-Chlorobutane Isobutyl formate Methyl acetate Methyl acrylate Methyl nitrate Acetone 1,4-Dioxane Dipropyl ether Methyl tert-butyl ether Diethyl sulfide Carbon disulfide Thiophene Nitromethane

63.8 53.4 55.7 34.9 61.0 59.3 54.5 48.6 40.5 33.4 61.0 57.0 64.6 53.5 62.5 52.5 55.5 zeotrope 63.8 51.3 61.2 39.8 59.7 64.4

60 87.4 79.44 5.3 32 38 21 15.0 9.5 6 38 27 95 19 54 73 12.1

40 12.6 20.56 94.7 68 62 79 85.0 90.5 94 62 73 5 81 46 27 87.9

72 14.3 62 71 16.4 9.1

28 85.7 38 29 83.6 90.9

5 7.5 21 29.2 49 78 31.7 75 68 72 96.8 93 34 84.2 37 5

95 92.5 79 70.8 51 22 68.3 25 32 28 3.2 7 66 15.8 63 95

Ethanol Pentane Cyclopentane Hexane Cyclohexane Heptane Octane Benzene Fluorobenzene Toluene Bromodichloromethane Iodomethane Chloroform Trichloronitromethane Carbon tetrachloride 1,2-Dichloroethane 3-Chloro-1-propene

34.3 44.7 58.7 64.8 70.9 77.0 67.9 70.0 76.7 75.5 41.2 59.3 77.5 65.0 70.5 44

4.35

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

20.5 10.5 6 2.8 44 27 43 20.3 40 76 44 44 41 29 91 56

79.5 89.5 94 97.2 56 73 57 79.7 60 24 56 56 59 71 9 44

4 18.5 34.7 34.7 70 16.9 51.2

96 81.5 65.3 65.3 30 83.1 48.8

94 92.2 8 3 64 51 48 49 30 37 55

6 7.8 92 97 36 49 52 51 70 63 45

92.1 58.5 93 19

7.9 41.5 7 81

Ethanol (continued ) 1-Bromopropane 2-Bromopropane 1-Chloropropane 2-Chloropropane 1-Iodopropane 2-Iodopropane 1-Bromobutane 1-Chlorobutane 2-Butanone 1,1-Diethoxyethane Dipropyl ether Acetonitrile Acrylonitrile Nitromethane Carbon disulfide Diethyl sulfide

62.8 55.6 45.0 35.6 75.4 71.5 75.0 65.7 74.8 78.0 74.5 72.5 70.8 76.1 42.6 72.6 1-Propanol

Hexane Cyclohexane Methylcyclohexane Heptane Octane Benzene Toluene o-Xylene m-Xylene p-Xylene Styrene Propyl formate Butyl formate Propyl acetate Ethyl propionate Methyl butyrate Dipropyl ether 1,1-Diethoxyethane 1,4-Dioxane Chloroform Carbon tetrachloride Trichloronitromethane Iodoethane 1,2-Dichloroethane

65.7 74.7 87.0 84.6 93.9 77.1 92.5 zeotrope 97.1 96.9 97.0 80.7 95.5 94.7 93.4 94.4 85.7 92.4 95.3 zeotrope 73.4 94.1 70 80.7

4.36

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

52 9 18 80 18 48.4 8.8 94.5

48 91 82 20 82 51.6 91.2 5.5

6 23 32 50.5 84 33.7 30 69 4.2 35 18 43.5 15 20 2.8 20.5 12 42 32 23 25 60 37 56 60 32 63 10 14.1

94 77 68 49.5 16 66.3 70 31 95.8 65 82 56.5 85 80 97.2 79.5 88 58 68 77 75 40 63 44 40 68 37 90 85.9

1-Propanol (continued ) Tetrachloroethylene 1-Bromopropane 1-Chlorobutane Chlorobenzene Fluorobenzene Nitromethane 1-Nitropropane Carbon disulfide

94.0 69.7 74.8 96.5 80.2 89.1 97.0 45.7 2-Propanol

Pentane Hexane Cyclohexane Heptane Octane Benzene Fluorobenzene Toluene Chloroform Trichloronitromethane Carbon tetrachloride 1,2-Dichloroethane Iodoethane 3-Bromo-1-propene 1-Chloropropane 1-Bromopropane 2-Bromopropane 1-Iodopropane 2-Iodopropane 1-Chlorobutane Ethyl acetate Isopropyl acetate Methyl propionate Acrylonitrile Butylamine 2-Butanone 1,1-Diethoxyethane Ethyl propyl ether Diisopropyl ether

35.5 62.7 69.4 76.4 81.6 71.7 74.5 80.6 60.8 81.9 69.0 74.7 67.1 66.5 46.4 66.8 57.8 79.8 76.0 70.8 75.3 81.3 76.4 71.7 74.7 77.5 81.3 62.0 66.2

4.37

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

9.5 5 3.2 20 18 45.2 71.5 27.8 75 71.5 68 65.1 23.6 69 47 50 64 17 40 52 63 45 82.5 48 13 97.6 68 7 30 56 52 77.1 35.7 69 32.2 50 45

90.5 95 96.8 80 82 54.8 28.5 72.2 25 28.5 32 34.9 76.4 31 53 50 36 83 60 48 37 55 17.5 52 87 2.4 32 93 70 44 48 22.9 64.3 31 67.8 50 55

14.2 14

85.8 86

1-Butanol Cyclohexane Cyclohexene Hexane Methylcyclohexane Heptane Octane Nonane Toluene o-Xylene m-Xylene p-Xylene Ethylbenzene Butyl formate Isopentyl formate Butyl acetate Isobutyl acetate Ethyl butyrate Ethyl isobutyrate Methyl isopentanoate Ethyl borate Ethyl carbonate Isobutyl nitrate Dibutyl ether Diisobutyl ether 1,1-Diethoxyethane Carbon tetrachloride Tetrachloroethylene 2-Bromo-2-methylpropane 2-Iodo-2-methylpropane Chlorobenzene Paraldehyde Hexaldehyde Ethylenediamine Pyridine 1-Nitropropane Butyronitrile Diisopropyl sulfide

79.8 82.0 68.2 95.3 93.9 108.5 115.9 105.5 116.8 116.5 115.7 115.9 105.8 115.9 117.2 114.5 115.7 109.2 113.5 113.0 116.5 112.8 117.8 113.5 101.0 76.6 110.0 90.2 110.5 115.3 115.8 116.8 124.7 118.6 115.3 113.0 112.0 2-Methyl-2-propanol

Cyclohexene Cyclohexane

80.5 78.3

4.38

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Water

Other component

2-Methyl-2-propanol (continued ) Methylcyclopentane Hexane Methylcyclohexane Heptane 2,5-Dimethylhexane 1,3-Dimethylcyclohexane 2,2,4-Trimethylpentane Benzene Chlorobenzene Fluorobenzene Toluene Ethylbenzene p-Xylene Butyl formate Isobutyl formate Propyl acetate Isobutyl acetate Methyl butyrate Ethyl isobutyrate Methyl chloroacetate Dipropyl ether Isobutyl vinyl ether 1,1-Diethoxyethane 2-Pentanone 3-Pentanone 1,2-Dichloroethane 1-Bromobutane 1-Chlorobutane 2-Bromo-2-methylpropane 2-Iodo-2-methylpropane 1-Nitropropane Isobutyl nitrate Diisopropyl sulfide

71.0 68.3 92.6 90.8 98.7 102.2 92.0 79.3 107.1 84.0 101.2 107.2 107.1 103.0 97.4 101.0 107.6 101.3 105.5 107.6 89.5 82.7 98.2 101.8 107.7 83.5 95.0 77.7 88.8 104.0 105.3 105.6 105.8

5 2.5 32 27 42 56 27 7.4 63 9 45 80 88.6 40 12 17 92 25 52 12 10 6.2 20 19 20 6.5 21 4 12 36 15.2 36 73

95 97.5 68 73 58 44 73 92.6 37 91 55 20 11.4 60 88 83 8 75 48 88 90 93.8 80 81 80 93.5 79 96 88 64 84.8 64 27

7 30 10 49 94 24

93 70 90 51 6 76

3-Methyl-1-butanol Heptane Octane Toluene Ethylbenzene Isopropylbenzene Camphene

97.7 117.0 109.7 125.7 131.6 130.9

4.39

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

3-Methyl-1-butanol (continued ) Bromobenzene o-Fluorotoluene Butyl acetate Paraldehyde Dibutyl ether

131.7 112.1 125.9 123.5 129.8

85 14.0 16.5 22.0 65

15 86.0 83.5 78.0 35

14 5 40 75 41 92

86 95 60 25 59 8

42 4.5 58 50 68 17.36 50 53 55 18 28 85 45

58 95.5 42 50 32 82.64 50 47 45 82 72 15 55

6 35 83.1 46 25 21 47 22 51.0

94 65 16.9 54 75 79 53 78 49.0

Cyclohexanol o-Xylene m-Xylene Propylbenzene Indene Camphene Cineole

143.0 138.9 153.8 160.0 151.9 160.6 Allyl alcohol

Methylcyclohexane Hexane Cyclohexane 2,5-Dimethylhexane Octane Benzene Toluene Propyl acetate Methyl butyrate 1,2-Dichloroethane 3-Iodo-1-propene Chlorobenzene Diethyl sulfide

85.0 65.5 74.0 89.3 93.4 76.75 92.4 94.2 93.8 79.9 89.4 96.2 85.1 Phenol

2,7-Dimethyloctane Decane Tridecane Butylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Indene Camphene Benzaldehyde

159.5 168.0 180.6 175.0 166.0 163.5 177.8 156.1 175.6

4.40

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

13 50 78 15 75.4 71.2 67.5 57.0 72.5 52.3 41.9 39.2 53

87 50 22 85 24.6 29.8 32.5 43.0 27.5 47.7 58.1 60.8 47

60 11 57

40 89 43

61 62 30 6.5 50 72 12 58 7 85.8

39 38 70 93.5 50 28 88 42 93 14.2

15 14 38 10.8 48 50 55 80 67 65 72

85 86 62 89.2 52 50 45 20 33 35 28

Phenol (continued ) 1-Octanol 2-Octanol Dipentyl ether Diisopentyl ether 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine 2,4-Dimethylpyridine 2,6-Dimethylpyridine 2,4,6-Trimethylpyridine Aniline Ethylene diacetate Iodobenzene

195.4 184.5 180.2 172.2 185.5 188.9 190.0 193.4 185.5 195.2 185.8 195.5 177.7 Benzyl alcohol

Naphthalene D-Limonene 1,3,5-Triethylbenzene o-Cresol m-Cresol p-Cresol N-Methylaniline N,N-Dimethylaniline N-Ethylaniline N, N-Diethylaniline Iodobenzene Nitrobenzene o-Bromotoluene Borneol

204.1 176.4 203.2 zeotrope 207.1 206.8 195.8 193.9 202.8 204.2 187.8 204.0 181.3 205.1 2-Ethoxyethanol

Methylcyclohexane Heptane Octane Toluene Ethylbenzene p-Xylene Styrene Propylbenzene Isopropylbenzene Camphene Propyl butyrate

98.6 96.5 116.0 110.2 127.8 128.6 130.0 134.6 133.2 131.0 133.5

4.41

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

53 32 73.4 30 15 52 58.5 91 42

47 68 26.6 70 85 48 41.5 9 58

3 23 55 2.3 16.5 87 6.55 6.4 13 19 18 51 60.0 57.2 98.3 26 74.2 82 20 40 66.5 68.5 56 69 27 60 89 51.5 46.5 25 6.4

97 77 45 97.7 83.5 13 93.45 93.6 87 81 82 49 40.0 42.8 1.7 74 25.8 18 80 60 33.5 31.5 44 31 73 40 11 48.5 53.5 75 93.6

2-Butoxyethanol Dipentene 1,3,5-Trimethylbenzene Butylbenzene Camphene o-Cresol Phenetole Cineole Benzaldehyde Diisobutyl sulfide

164.0 162.0 169.6 154.5 191.6 167.1 168.9 171.0 163.8 1,2-Ethanediol

Heptane Decane Tridecane Toluene Styrene Stilbene m-Xylene p-Xylene 1,3,5-Trimethylbenzene Propylbenzene Isopropylbenzene Naphthalene 1-Methylnaphthalene 2-Methylnaphthalene Anthracene Indene Acenaphthene Fluorene Camphene Camphor Biphenyl Diphenylmethane Benzyl alcohol 2-Phenylethanol o-Cresol m-Cresol 3,4-Dimethylphenol Menthol Ethyl benzoate o-Bromotoluene Dibutyl ether

97.9 161.0 188.0 110.1 139.5 196.8 135.1 134.5 156 152 147.0 183.9 190.3 189.1 197 168.4 194.65 196.0 152.5 186.2 192.3 193.3 193.1 194.4 189.6 195.2 197.2 188.6 186.1 166.8 139.5

4.42

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Alcohol

Other component

10.5 60 87 52 47 33.5 42 9.7 79.5 94 4 94.4 30 59 48.5

89.5 40 13 48 53 66.5 58 90.3 20.5 6 96 5.6 70 41 51.5

20 71 65 51 31 33 42 28 32

80 29 35 49 69 67 58 72 68

1,2-Ethanediol (continued ) Methoxybenzene Diphenyl ether Benzyl phenyl ether Acetophenone 2,4-Dimethylaniline N,N-Dimethylaniline m-Toluidine 2,4,6-Trimethylpyridine Quinoline Tetrachloroethylene 1,2-Dibromoethane Chlorobenzene -Chlorotoluene Nitrobenzene o-Nitrotoluene

150.5 193.1 195.5 185.7 188.6 175.9 188.6 170.5 196.4 119.1 129.8 130.1 167.0 185.9 188.5 1,2-Ethanediol monoacetate

Indene 1-Octanol Phenol o-Cresol m-Cresol p-Cresol Dipentyl ether Diisopentyl ether m-Bromotoluene

180.0 189.5 197.5 199.5 206.5 206.0 180.8 170.2 182.0

D. Binary azeotropes containing ketones Composition, wt % System

BP of azeotrope, C

Ketone

Other component

36 20 67.5 59

64 80 32.5 41

Acetone Cyclopentane Pentane Cyclohexane Hexane

41.0 32.5 53.0 49.8

4.43

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Ketone

Other component

89.5 38.2 48.3 61 78.1 11.5 67 57

10.5 61.8 51.7 39 21.9 88.5 33 43

40 28.6 70 95 44 69 35 11.8 60 30 38 75

60 71.4 30 5 56 31 65 88.2 40 70 62 25

Acetone (continued ) Heptane Diethylamine Methyl acetate Diisopropyl ether Chloroform Carbon tetrachloride Carbon disulfide Ethylene sulfide

55.9 51.4 55.8 54.2 64.4 56.1 39.3 51.5 2-Butanone

Cyclohexane Hexane Heptane 2,5-Dimethylhexane Benzene 2-Methyl-2-propanol Butylamine Ethyl acetate Methyl propionate Butyl nitrite 1-Chlorobutane Fluorobenzene

71.8 64.2 77.0 79.0 78.33 78.7 74.0 77.1 79.0 76.7 77.0 79.3

E. Miscellaneous binary azeotropes Composition, wt % System

BP of azeotrope, C

Solvent

Other component

169.2 213.0 215.2 218.2 142.6 138.4 137.8 144

18 50.5 56.5 68 11 10 8 12

82 49.5 43.5 32 89 90 92 88

170.5

19

81

Solvent: acetamide Dipentene Biphenyl Diphenylmethane 1,2-Diphenylethane o-Xylene m-Xylene p-Xylene Styrene 4-Isopropyl-1methylbenzene

4.44

SECTION 4

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Solvent

Other component

Solvent: acetamide (continued ) Naphthalene 1-Methylnaphthalene 2-Methylnaphthalene Indene Acenaphthene Camphene Camphor Benzaldehyde 3,4-Dimethylphenol 2-Methoxy-4-(2-propenyl)phenol N-Methylaniline N-Ethylaniline N,N-Diethylaniline Diphenyl ether Safrole Tetrachloroethylene

199.6 209.8 208.3 177.2 217.1 155.5 199.8 178.6 221.1

27 43.8 40 17.5 64.2 12 23 6.5 96

73 56.2 60 82.5 35.8 88 77 93.5 4

220.8 193.8 199.0 198.1 214.6 208.8 120.5

88 14 18 24 52 32 97.4

12 86 82 76 48 68 2.6

13.5 36 57.5 71.5 86.2 95.2 46 13.5 12.0 41.5 83 8 55 28 66

86.5 64 42.5 28.5 13.8 4.8 54 86.5 88.0 58.5 17 92 45 72 34

25.3 56.1 89.9 22.2 13.1 8

74.7 43.9 10.1 77.8 86.9 92

Solvent: aniline Nonane Decane Undecane Dodecane Tridecane Tetradecane Butylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Indene 1-Octanol o-Cresol Dipentyl ether Diisopentyl ether Hexachloroethane

149.2 167.3 175.3 180.4 182.9 183.9 177.8 168.6 164.3 179.8 183.9 191.3 177.5 169.3 176.8 Solvent: pyridine

Heptane Octane Nonane Toluene Phenol Piperidine

95.6 109.5 115.1 110.1 183.1 106.1

4.45

PHYSICAL PROPERTIES

TABLE 4.7 Binary Azeotropic (Constant Boiling) Mixtures (continued ) Composition, wt % System

BP of azeotrope, C

Solvent

Other component

14 41.2 11.2 83.2 64 42.7

86 58.8 88.8 16.8 36 57.3

16 64.7 51.9 4.7 99.3 46.3 78.8 48.3 97.7

84 35.3 48.1 95.3 0.7 53.7 21.2 51.7 2.3

Solvent: thiophene Methylcyclopentane Cyclohexane Hexane Heptane 2,3-Dimethylpentane 2,4-Dimethylpentane

71.5 77.9 68.5 83.1 80.9 76.6 Solvent: benzene

Methylcyclopentane Cyclohexene Cyclohexane Hexane Heptane 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 2,2,4-Trimethylpentane

71.7 78.9 77.6 68.5 80.1 75.9 79.4 75.2 80.1

Solvent: bis(2-hydroxyethyl) ether Biphenyl Diphenylmethane 1,3,5-Trimethylbenzene Naphthalene 1-Methylnaphthalene 2-Methylnaphthalene Acenaphthene Fluorene Benzyl acetate Bornyl acetate Ethyl fumarate Dimethyl o-phthalate Methyl salicylate 2-Hydroxy-1-isopropyl4-methylbenzene 1,2-Dihydroxybenzene Safrole Isosafrole Benzyl phenyl ether Nitrobenzene m-Nitrotoluene o-Nitrophenol Quinoline p-Dibromobenzene

232.7 236.0 210.0 212.6 277.0 225.5 239.6 243.0 214.9 223.0 217.1 245.4 220.6

48 52 22 22 45 39 62 80 7 18 10 96.3 15

52 48 78 78 55 61 38 20 93 82 90 3.7 85

232.3 259.5 225.5 233.5 241.5 210.0 224.2 216.0 233.6 212.9

13 46 33 46 80 10 25 10.5 29 13

87 54 67 54 20 90 75 89.5 71 87

4.46

SECTION 4

TABLE 4.8 Ternary Azeotropic Mixtures A. Ternary azeotropes containing water and alcohols Composition, wt %

System

BP of azeotrope, C

Water

Alcohol

Other component

Methanol Chloroform 2-Methyl-1,3-butadiene Methyl chloroacetate

52.3 30.2 67.9

1.3 0.6 6.3

8.2 5.4 81.2

90.5 94.0 13.5

1 8.7 7.4 7.5 6.3 1.6 4.5 2.3 4.8 4.8 5 11.4 12.1 9.0 6.1 3 12 5.5 9

55 20.3 18.5 42.5 8.6 5.0 10.0 3.5 87.9 19.7 17 27.6 18.4 8.4 33.0 12 37 16.1 13

44 71.0 74.1 50.0 85.1 93.4 85.5 94.2 7.3 75.5 78 61.0 69.5 82.6 60.9 85 51 78.4 78

7.6 5 8.5 27.4 8.0 11.7 20 17.0 13 12.5

10.1 11 10.0 51.6 44.8 20.2 20 10.0 5 20.7

82.3 84 81.5 21.0 47.2 68.1 60 73.0 82 66.8

7.5 12.5

18.7 40.5

73.8 47.0

Ethanol Acetonitrile Acrylonitrile Benzene Butylamine Butyl methyl ether Carbon disulfide Carbon tetrachloride Chloroform Crotonaldehyde Cyclohexane 1,2-Dichloroethane 1,1-Diethoxyethane Diethoxymethane Ethyl acetate Heptane Hexane Toluene Trichloroethylene Triethylamine

72.9 69.5 64.9 81.8 62 41.3 62 55.3 78.0 62.6 66.7 77.8 73.2 70.2 68.8 56.0 74.4 67.0 74.7 1-Propanol

Benzene Carbon tetrachloride Cyclohexane 1,1-Dipropoxyethane Dipropoxymethane Dipropyl ether 3-Pentanone Propyl acetate Propyl formate Tetrachloroethylene

67 65.4 66.6 87.6 86.4 74.8 81.2 82.5 70.8 81.2 2-Propanol

Benzene Butylamine

66.5 83

4.47

PHYSICAL PROPERTIES

TABLE 4.8 Ternary Azeotropic Mixtures (continued ) Composition, wt %

System

BP of azeotrope, C

Other component

Water

Alcohol

7.5 13.1 7

18.5 38.2 20

74.0 48.7 73

37.3 21.3 29.9 41.4 19.2 69.9 60.0

27.4 10.0 34.6 7.6 2.9 18.3 14.6

35.3 68.7 35.5 51.0 77.9 11.8 25.4

4.05 8.9 9

4.95 10.8 19

91.00 80.3 72

30.4 17.3 17.9

23.1 6.7 16.4

46.5 76.0 65.7

8.1 3.1 8

21.4 11.9 21

70.5 85.0 71

44.8 32.4

31.2 19.6

24.0 48.0

8.6 5 8 8.5

9.2 11 11 5.1

82.2 84 81 86.4

2-Propanol (continued ) Cyclohexane Toluene Trichloroethylene

64.3 76.3 69.4 1-Butanol

Butyl acetate Butyl formate Dibutyl ether Heptane Hexane Nonane Octane

89.4 83.6 90.6 78.1 61.5 90.0 86.1 2-Butanol

Carbon tetrachloride Cyclohexane Isooctane

65 69.7 76.3 2-Methyl-1-propanol

Isobutyl acetate Isobutyl formate Toluene

86.8 80.2 81.3 2-Methyl-2-propanol

Benzene Carbon tetrachloride Cyclohexane

67.3 64.7 65.0 3-Methyl-1-butanol

Isopentyl acetate Isopentyl formate

93.6 89.8 Allyl alcohol

Benzene Carbon tetrachloride Cyclohexane Hexane

68.2 65.2 66.2 59.7

4.48

TABLE 4.8 Ternary Azeotropic Mixtures (continued) B. Other ternary azeotropes

System

BP of azeotrope, C

Composition, wt %

System

BP of azeotrope, C

Composition, wt %

Water Acetone 2-Methyl-1,3-butadiene

32.5

0.4 7.6 92.0

Water Nitromethane Heptane

71.4

7.9 29.7 62.4

Water Acetonitrile Benzene

66

8.2 23.3 68.5

Water Nitromethane Nonane

80.7

17.4 58.3 24.3

Water Acetronitrile Trichloroethylene

67

6.4 20.5 73.1

Water Nitromethane Octane

77.4

12.4 44.3 43.3

Water Acetonitrile Triethylamine

68.6

3.5 9.6 86.9

Water Nitromethane Pentane

33.1

2.1 6.5 91.4

Water 2-Butanone Cyclohexane

63.6

5 35 60

Water Nitromethane Undecane

82.8

20.6 73.3 6.1

Water Butyraldehyde Hexane

55.0

4 21 75

Water Pyridine Dodecane

93.5

40.5 54.5 5.0

Water Formic acid Isopentanoic acid

107.6

21.3 76.3 2.4

Water Pyridine Undecane

93.1

38.5 51.0 10.5

Water Formic acid Isobutyric acid

107.0

15.5 66.8 17.7

Water Pyridine Decane

92.3

35.5 45.5 19.0

4.49

Water Formic acid Butyric acid

107.6

19.5 75.9 4.6

Water Pyridine Nonane

90.5

30.5 37.0 32.5

Water Formic acid Propionic acid

107.2

18.6 71.9 9.5

Water Pyridine Octane

86.7

22.4 25.5 52.0

Water Hydrogen bromide Chlorobenzene

105

11.0 10.4 78.6

Water Pyridine Heptane

78.6

14.0 15.5 70.5

Water Hydrogen chloride Chlorobenzene

96.9

20.2 5.3 74.5

Acetic acid Pyridine Acetic anhydride

134.4

23 55 22

Water Hydrogen chloride Phenol

107.3

64.8 15.8 19.4

Acetic acid Pyridine Decane

134.1

31.4 38.2 30.4

Water Hydrogen fluoride Fluorosilic acid

116.1

54 10 36

Acetic acid Pyridine Ethylbenzene

129.1

13.5 25.2 61.3

Water Nitroethane Heptane

75.1

11.5 75.1 64.0

Acetic acid Pyridine Heptane

98.5

3.4 10.6 86.0

Water Nitroethane Hexane

59.5

8.4 9.3 82.3

Acetic acid Pyridine Nonane

128.0

20.7 29.4 49.9

Water Nitromethane Decane

82.4

19.1 68.1 12.8

Acetic acid Pyridine Octane

115.7

10.4 20.1 69.5

Water Nitromethane Dodecane

83.1

21.5 75.3 3.2

Acetic acid Pyridine o-Xylene

132.2

17.7 30.5 51.8

4.50

TABLE 4.8 Ternary Azeotropic Mixtures (continued) BP of azeotrope, C

Composition, wt%

Acetic acid Pyridine p-Xylene

129.2

10.2 22.5 67.3

Methanol Methyl acetate Hexane

47.4

14.6 36.8 48.6

Acetic acid 2,6-Dimethylpyridine Undecane

163.0

75.0 13.8 11.2

Ethanol Acetone Chloroform

63.2

10.4 24.3 65.3

Acetic acid 2,6-Dimethylpyridine Decane

147.0

12.6 74.3 13.1

Ethanol Acetonitrile Triethylamine

70.1

8 34 58

Acetic acid 2-Methylpyridine Decane

141.3

19.9 46.8 33.3

Ethanol Benzene Cyclohexane

64.7

29.6 12.8 57.6

Acetic acid 2-Methylpyridine Nonane

135.0

12.8 38.4 48.8

Ethanol Chloroform Hexane

57.3

9.5 56.1 34.4

Acetic acid 2-Methylpyridine Octane

121.3

3.6 24.8 71.6

1-Propanol Benzene Cyclohexane

73.8

15.5 30.4 54.2

Acetic acid Benzene Cyclohexane

77.2

7.6 34.4 58.0

2-Propanol Benzene Cyclohexane

69.1

31.1 15.0 53.9

Acetic acid 2-Methyl-1-butanol Isopentyl acetate

132

15 54 31

1-Butanol Benzene Cyclohexane

77.4

4 48 48

Propionic acid 2-Methylpyridine Decane

149.3

29.5 32.0 38.5

1-Butanol Pyridine Toluene

108.7

11.9 20.7 76.4

System

System

BP of azeotrope, C

Composition, wt%

Propionic acid 2-Methylpyridine Nonane

140.1

16.5 21.5 42.0

1,2-Ethanediol Phenol 2,6-Dimethylpyridine

185.0

8.7 74.6 16.7

Propionic acid 2-Methylpyridine Octane

123.7

4.5 10.5 85.0

1,2-Ethanediol Phenol 2-Methylpyridine

185.1

5.9 79.1 15.0

Propionic acid 2-Methylpyridine Undecane

153.4

43.0 40.0 17.0

1,2-Ethanediol Phenol 3-Methylpyridine

186.4

15.9 67.7 16.4

Propionic acid Pyridine Undecane

147.1

55.5 26.4 18.1

1,2-Ethanediol Phenol 2,4,6-Trimethylpyridine

188.6

29.5 54.8 15.7

Methanol Acetone Chloroform

57.5

23 30 47

Acetone Chloroform Hexane

60.8

3.6 68.8 27.6

Methanol Acetone Hexane

47

14.6 30.8 59.6

Acetone Methyl acetate Hexane

49.7

51.1 5.6 43.3

Methanol Acetone Methyl acetate

53.7

17.4 5.8 76.8

Chloroform Ethyl formate 2-Bromopropane

62.0

79.7 5.3 15.7

Methanol Methyl acetate Cyclohexane

50.8

17.8 48.6 33.6

1,4-Dioxane 2-Methyl-1-propanol Toluene

101.8

44.3 26.7 29.0

4.51

4.52

SECTION 4

FREEZING POINTS Crystalline organic compounds typically have a characteristic melting point. In some cases, a compound may have more than one arrangement in the crystal and such polymorphs will exhibit differences in melting behavior. For the most part, however, the melting point of a compound is characteristic and invariant for a pure sample. When contaminated by a second substance, however, the melting (or freezing) point is typically lowered. A classical test used to determine if two samples that have the same melting point are identical is to intimately mix them and record the melting point of the mixture. If the melting point of the blend is identical to that of each individual compound prior to mixing, the two substances are judged to be identical. When the two compounds are not the same, the melting point of the mixture is typically lowered and broadened. The melting or freezing point depression can be used to determine an approximate molecular weight for a given substance. The cryoscopic constant Kf gives the depression of the melting point T (in degrees Celsius) produced when 1 mol of solute is dissolved in 1000 g of a solvent. It is applicable only to dilute solutions for which the number of moles of solute is negligible in comparison with the number of moles of solvent. Because camphor is conveniently available and has a large Kf value, it is often used in this application. A known amount of the substance whose molecular weight is to be determined (the solute) is mixed with a larger amount of camphor (the solvent). Melting the mixture permits intimate mixing. The lowering or depression of the freezing point is then used to calculate the molecular weight from the following equation M2 

1000w2Kf w1 T

where M2 is the molecular weight to be determined of the solute, w1 is the exact weight of the solvent, w2 is the exact weight of the added compound of unknown molecular mass,

T is the change in temperature, and Kf is the cryoscopic constant given in the Table 4.9A. In Table 4.9A, a range of compounds and their cryoscopic constants are recorded. All of the same data are included in Table 4.9B but they are rearranged in order of increasing melting point at the left and decreasing Kf at the right.

TABLE 4.9A Molecular Lowering of the Melting of Freezing Point Compound

Kf

MP

Acetamide Acetic acid Acetone Ammonia Aniline Antimony(III) chloride

4.04 3.90 2.40 0.957 5.87 17.95

80.1 16.63 95.35 77.75 5.98 73.4

Benzene Benzonitrile Benzophenone Bicyclohexane Biphenyl Borneol Bornylamine Butanedinitrile

5.12 5.34 9.8 14.52 8.0 35.8 40.6 18.26

5.53 12.75 48.1 3–4 68.8 204 163 57.9

Compound

Kf

MP

Camphene Camphorquinone D-()-Camphor Carbon tetrachloride o-Cresol p-Cresol Cyclohexane Cyclohexanol Cyclohexylcyclohexane Cyclopentadecanone

31.08 45.7 39.7 29.8 5.60 6.96 20.0 39.3 14.52 21.3

51–52 199 178.8 22.9 30.9 34.8 6.5 25.2 3–4 64–66

Z-Decahydronaphthalene E-Decahydronaphthalene Dibenz[de,kl)anthracene Dibenzyl ether

19.47 20.81 25.7 6.27

43.0 30.4 273–274 3.5

4.53

PHYSICAL PROPERTIES

TABLE 4.9A Molecular Lowering of the Melting of Freezing Point (continued ) Compound

Kf

MP

1,2-Dibromoethane Diethyl ether 1,2-Dimethoxybenzene N, N-Dimethylacetamide 2,2-Dimethyl-1-propanol Dimethyl sulfoxide 1,4-Dioxane Diphenylamine Diphenyl ether

12.5 1.79 6.38 4.46 11.0 4.07 4.63 8.60 7.88

10.0 116.3 22.5 20.0 52–54 18.5 11.7 53–54 26.9

1,2-Ethanediamine Ethoxybenzene

2.43 7.15

8.5 29.5

Formamide Formic acid

3.85 2.77

2.6 8.5

Glycerol

3.3–3.7

18.18

Hexamethylphosphoramide N-Methylacetamide 2-Methyl-2-butanol Methylcyclohexane Methyl Z-9-octadecenoate 2-Methyl -2-propanol

6.93 6.65 10.4 14.13 3.4 8.37

7.2 30.6 9.0 126.6 19.9 25.8

Naphthalene

6.94

80.2

Compound

Kf

MP

Nitrobenzene

6.852

5.8

Octadecanoic acid 2-Oxohexamethyleneimine

4.50

70

7.30

69.2

Phenol Pyridine

7.40 4.75

40.9 41.6

Quinoline

1.95

14.9

Succinonitrile Sulfuric acid

18.26 1.86

46–48 10.38

21.7 37.7

0.0 26.0

64.1 5.372 14.4 6.7

27.6 43.8 8.1 1–2

12.45

93.4

1,1,2,2,-Tetrabromoethane 1,1,2,2,-Tetrachloro1,2difluoroethane Tetramethylene sulfone p-Toluidine Tribromomethane 1,3,3-Trimethyl-2oxabicyclo[2.2.2]octane Triphenylmethane Water

1.86

0.000

p-Xylene

4.3

13.3

The same data are presented in Table 4.9B but the information is rearranged at the left in order of increasing melting point and at the right in order of decreasing Kf. TABLE 4.9B Molecular Lowering of the Melting of Freezing Point Compound

Kf

MP

Compound

Kf

MP

Methylcyclohexane Diethyl ether Acetone Ammonia Z-Decahydronaphthalene Pyridine E-Decahydronaphthalene Ethoxybenzene Carbon tetrachloride N, N- Dimethylacetamide Quinoline Benzonitrile 2-Methyl-2-butanol Aniline 1,1,2,2-Tetrabromoethane Water 1,3,3-Trimethyl-2oxabicyclo[2.2.2]octane

14.13 1.79 2.4 0.957 19.47 4.75 20.81 7.15 29.8 4.46 1.95 5.34 10.4 5.87 21.7 1.86 6.7

126.6 116.3 95.35 77.75 43 41.6 30.4 29.5 22.9 20 14.9 12.75 9 5.98 0 0 1–2

Tetramethylene sulfone Camphorquinone Bornylamine D-()-Camphor Cyclohexanol 1,1,2,2-Tetrachloro-1,2difluoroethane Borneol Camphene Carbon tetrachloride Dibenz[de,kl)anthracene 1,1,2,2-Tetrabromoethane Cyclopentadecanone E- Decahydronaphthalene Cyclohexane Z-Decahydronaphthalene Succinonitrile Butanedinitrile

64.1 45.7 40.6 39.7 39.3 37.7

27.6 199 163 178.8 25.2 26

35.8 31.08 29.8 25.7 21.7 21.3 20.81 20 19.47 18.26 18.26

204 51–52 22.9 273–274 0 64–66 30.4 6.5 43 46–48 57.9

4.54

SECTION 4

TABLE 4.9B Molecular Lowering of the Melting of Freezing Point (continued ) Compound

Kf

MP

Compound

Kf

MP

Formamide Bicyclohexane Dibenzyl ether Benzene Nitrobenzene Cyclohexane Cyclohexylcyclohexane Hexamethylphosphoramide Tribromomethane 1,2-Ethanediamine Formic acid 1,2-Dibromoethane Sulfuric acid 1,4-Dioxane p-Xylene Acetic acid Glycerol Dimethyl sulfoxide Methyl Z-9-octadecenoate 1,2-Dimethoxybenzene Cyclohexanol 2-Methyl-2-propanol 1,1,2,2-Tetrachloro-1,2difluoroethane Diphenyl ether Tetramethylene sulfone N-Methylacetamide o-Cresol p-Cresol Phenol p-Toluidine Succinonitrile Benzophenone Camphene 2,2-Dimethyl-1-propanol Diphenylamine Butanedinitrile Cyclopentadecanone Biphenyl 2-Oxohexamethylene imine Octadecanoic acid Antimony(III) chloride Acetamide Naphthalene Triphenylmethane Bornylamine D-()-Camphor Camphorquinone Borneol Dibenz[de,kl) anthracene

3.85 14.52 6.27 5.12 6.852 20 14.52

2.6 3–4 3.5 5.53 5.8 6.5 6.5

Antimony(III) chloride Bicyclohexane Cyclohexylcyclohexane Tribromomethane Methylcyclohexane 1,2-Dibromoethane Triphenylmethane

17.95 14.52 14.52 14.4 14.13 12.5 12.45

73.4 3–4 6.5 8.1 126.6 10 93.4

6.93 14.4 2.43 2.77 12.5 1.86 4.63 4.3 3.9 3.3–3.7 4.07 3.4 6.38 39.3 8.37 37.7

7.2 8.1 8.5 8.5 10 10.38 11.7 13.3 16.63 18.18 18.5 19.9 22.5 25.2 25.8 26

11 10.4 9.8 8.6 8.37 8 7.88 7.4 7.3 7.15 6.96 6.94 6.93 6.852

52–54 9 48.1 53–54 25.8 68.8 26.9 40.9 69.2 29.5 34.8 80.2 7.2 5.8

7.88 64.1 6.65 5.6 6.96 7.4 5.372 18.26 9.8 31.08 11 8.6 18.26 21.3 8 7.3 4.5 17.95 4.04 6.94 12.45 40.6 39.7 45.7 35.8 25.7

26.9 27.6 30.6 30.9 34.8 40.9 43.8 46–48 48.1 51–52 52–54 53–54 57.9 64–66 68.8 69.2 70 73.4 80.1 80.2 93.4 163 178.8 199 204 273–274

2,2-Dimethyl-1-propanol 2-Methyl-2-butanol Benzophenone Diphenylamine 2-Methyl-2-propanol Biphenyl Diphenyl ether Phenol 2-Oxohexamethylene imine Ethoxybenzene p-Cresol Naphthalene Hexamethylphosphoramide Nitrobenzene 1,3,3-Trimethyl-2oxabicyclo[2.2.2]octane N-Methylacetamide 1,2-Dimethoxybenzene Dibenzyl ether Aniline o-Cresol p-Toluidine Benzonitrile Benzene Pyridine 1,4-Dioxane Octadecanoic acid N, N- Dimethylacetamide p-Xylene Dimethyl sulfoxide Acetamide Acetic acid Formamide Glycerol Methyl Z-9-octadecenoate Formic acid 1,2-Ethanediamine Acetone Quinoline Water Sulfuric acid Diethyl ether Ammonia

6.7 6.65 6.38 6.27 5.87 5.6 5.372 5.34 5.12 4.75 4.63 4.5 4.46 4.3 4.07 4.04 3.9 3.85 3.3–3.7 3.4 2.77 2.43 2.4 1.95 1.86 1.86 1.79 0.957

1–2 30.6 22.5 3.5 5.98 30.9 43.8 12.75 5.53 41.6 11.7 70 20 13.3 18.5 80.1 16.63 2.6 18.18 19.9 8.5 8.5 95.35 14.9 0 10.38 116.3 77.75

4.55

PHYSICAL PROPERTIES

VISCOSITY, DIELECTRIC CONSTANT, DIPOLE MOMENT, SURFACE TENSION, AND REFRACTIVE INDEX Several additional physical properties are summarized in Table 4.10. These are viscosity, dielectric constant, dipole moment, and surface tension for selected common organic compounds.

Viscosity Viscosity may be thought of as a fluid’s resistance to flow or internal friction. It is characterized by the property called viscosity, which is designated  (eta). A fluid passing through a tube will flow more freely if its viscosity is low and more slowly if it is more viscous. Viscosity is given in Table 4.10 in units of milliNewton·second·meter2 or mN·s · m2. In fluid mechanics, the unit “poise” is equal to a force of 1 dyne · cm2 for two fluids passing each other at a rate of 1 cm · s1. Viscosity is typically greater at lower temperatures; temperatures (in C) are given in parentheses in the table. Dielectric Constant The dielectric constant (or relative permittivity) is usually expressed using the symbol . The dielectric  is defined as the ratio of electric fields E0/E for a vacuum and a substance placed between the plates of a capacitor. The dielectric constant of a vacuum is 1 and substances that can orient to greater or lesser extents in the applied field will have higher dielectric constants. The dielectric constant of heptane at 20 C is 1.9. Acetonitrile, CH3C ˜ N:, has a dielectric constant at 20 C of 37.5. The dielectric constant for water is near 80. The choice of a solvent for a particular reaction will usually depend on more than one variable. These include the liquid temperature range, the dielectric constant, and whether or not the solvent is reactive in the chemical reaction. The most important consideration in the latter context is often the presence of an easily transferred proton. Certain solvents, such as acetone, are considered aprotic but may transfer a proton under basic conditions. Thus the designations given below are general and approximate. They are intended to guide the reader to the more detailed information contained in the full tables. Common Solvents Listed in Order of Increasing Dielectric Constant (Ascending Polarity) Aprotic Solvents Dielectric constants 15 carbon disulfide carbon tetrachloride tetrachloroethylene 1,2-dichloroethylene chlorobenzene dichloromethane chloroform 1,4-dioxane diphenyl ether diethyl ether

Dielectric constants  15 acetone benzonitrile hexamethylphosphoramide N-methylpyrrolidone nitrobenzene nitromethane N,N-dimethylformamide (DMF) acetonitrile dimethyl sulfoxide (DMSO)

Protic Solvents Dielectric range 6–80 acetic acid trifluoroacetic acid phenols butanols propanols ethanol 2,2,2-trifluoroethanol methanol various glycols water

4.56

SECTION 4

Aprotic Solvents Dielectric constants 15

Protic Solvents

Dielectric constants  15

Dielectric range 6–80

tetrahydrofuran (THF) 1,2-dimethoxyethane (DME) ethyl acetate butyl acetate N,N-dimethylaniline pyridine

Dipole Moment The dipole moment of a molecule is the vectorial sum of the individual dipoles within it. Bond dipoles are usually represented using the symbol  and are expressed in units of Debye. The dipoles result from charge separation. The carbon–carbon bond in ethane, H3CˆCH3 is symmetrical and not expected to have a dipole moment. The carbon–oxygen bond of methanol (CH3OH), on the other hand, links two elements of differing electronegativity and is expected to have a significant molecular dipole. Methanol’s molecular dipole is 1.7 whereas, for ethane, it is 0. Experimentally, the molecular dipole can be measured. Individual bond dipoles cannot be measured but they have been inferred from experimental data for a variety of compounds. Estimates of the molecular dipole can be made by vector addition of individual moments. Such estimates (calculations) are indicative but may differ significantly from the measured values. The latter are recorded in Table 4.10. Four examples of dipole moments are instructive. First, the dipoles for chloromethane and dichloromethane are 1.87 D and 1.60 D, respectively. Although two chlorine–carbon bonds are present in the latter, the dipole is not along either but rather bisects the angle between them. This is illustrated schematically using the stylized arrow with its positive end in the form of a cross. The orientation question is shown clearly in the rigid dichlorobenzene framework. The dipole is 2.13 D for the ortho-isomer and 0 D when the dipoles exactly oppose each other. The orientation of dipoles can be assessed by comparing otherwise identical molecules. For example, amino is electron releasing and nitro is electron withdrawing. The molecular dipoles (1.53 D for aniline and 4.22 D for nitrobenzene) add to give an overall molecular dipole of 6.3 D for 4-nitroaniline. The importance of two polar CˆO bonds should be large Cl

Cl Cl H H3C

Cl

1.87 D

NH2

Cl

C

H

Cl

Cl

1.60 D

NO2

Cl

2.13 D

NH2

Cl 0D

1.50 D

OH

H

H

H

OH

OH NO2 1.53 D

4.22 D

6.3 D

H C

C

C

C H

OH

H

H 2.20 D

H

4.57

PHYSICAL PROPERTIES

if they are added and small if they oppose. The dynamics of the system must be taken into account for structures such as 1,2-dihydroxyethane (ethylene glycol), which is illustrated in the eclipsed and staggered conformers.

Surface Tension The surface tension is the force that acts on the surface of a liquid that tends to minimize the surface area of the liquid. Surface tension is also sometimes referred to as interfacial force or interfacial tension. The property of surface tension is temperature dependent. For the majority of compounds the dependence of the surface tension  on the temperature can be given as   a  bt where a and b are constants and t is the temperature in C. TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances States:

[g], gas [lq], liquid

Solvents:

[B], benzene, [C], carbon tetrachloride, [D], 1,4-dioxane, [H], hexane, [cH], cyclohexane,

C6H6 CCl4 C4H8O2 C6H14 C6H12

The temperature in degrees Celsius at which the viscosity, dielectric constant, dipole moment, and surface tension of a substance were measured is shown in this table in parentheses after the value. The solvent used or the physical state of the substance are also shown in parentheses after the temperature in square brackets, for example, [g] or [b] Alternate names for entries are listed in Table 1-14 at the bottom of each double page.

Surface tension, dyn · cm1 Substance

Acetaldehyde

Acetaldoxime Acetamide Acetanilide Acetic acid

Viscosity , mN · s · m2

Dielectric constant 

Dipole moment, D

0.280 (0) 0.256 (10) 0.22 (20) 1.415 (20)

21.8(10) 21.1 (21) 3 (23)

1.32 (105) 1.06 (120) 2.22 (120) 1.90 (130) 1.232 (20) 0.796 (50)

a

b

2.71 [g]

23.90

0.1360

30.1 (35)

59.2 (83) 60.6 (94) 3.65 (25) [B]

0.830 (20) [lq] 0.90 (25) [B] 3 90 (25) [B] 2.44 (30) [B] 46.21

6.15 (20) 6.29 (40)

1 76[g] 1.92 (20) [B]

29.58

47.66

0.102 1

0.091 2 0.009 4

4.58

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Acetic anhydride Acetone [lq] [g] Acetonitrile Acetophenone

Viscosity , mN · s · m2

Acrylic acid Acrylonitrile

Dipole moment, D

a

b

0.907 (20) 0.699 (40)

23.3 (0) 21.2 (20)

2.8 [g] 3.15 (20) [B]

35.52

0.143 6

0.391 (0) 0.318 (20) 0.009 33 (100) 0.012 8 (225) 0.397 (10) 0.329 (30) 2.015 (15) 1.511 (30)

20.7 (25) 17.6 (56) 1.015 9 (100)

2.77 (22) [B]

26.26

0.112

37.5 (20) 26.6 (82) 17.39 (25) 8.64 (202) 16.2 (20)

3.97 [g] 3.47 (20) [B] 2.96 (30) [B]

29.58

0.117 8

41.92

0.115 4

16.9 (2) 15.8 (22) 1.0217 (20) 1.001 34 (0)

2.47 (20) [B]

26.7 (15)

2.71 0

3.42

Acetyl bromide Acetyl chloride [lq] [g] Acetylene [g]

Dielectric constant, 

0.010 2 (30) 0.012 6 (101) 1.3 (20) 1.16 (25) 0.35 (20) 0.34 (25) 0.207 (30) 0.375 (25)

Allyl acetate Allylamine Allyl isothiocyanate 2-Aminoethanol 30.85 (15) 19.35 (25) Aniline 5.30 (15) 4.40 (20) 3.18 (30) Benzaldehyde 1.321 (25) Benzaldehyde oxime (mp 30) (mp 128) Benzene 0.649 (20) 0.566 (30) 0.395 (60) Benzamide Benzenesulfonyl chloride Benzenethiol 1.239 (20) 1.144 (25)

2.87

2.45 (20) [B]

0.193 5 [lq]

28.1 (30) 33.0 (20)

29.58

0.117 8

17.2 (18)

1.3 (25) [B] 3.2 (20) [B]

28.73 27.49 36.76

0.118 6 0.128 7 0.107 4

37.72 (25)

2.59 (25) [D]

51.11

0.111 7

6.89 (20) 5.93 (70)

1.53 (20) [B]

44.83

0.108 5

19.7 (0) 17.8 (20) 3.8 (20)

2.77 (20) [lq]

40.72

0.109 0

1.5 (25) [B] 0

28.88 (20)

27.56 (30)

3.42 (25) [B] 4.50 (20) [B]

47.26 45.48

0.070 5 0.111 7

1.13 (25) [lq] 1.19 (20) [B]

41.41

0.120 2

2.292 (15) 2.274 (25) 1.002 8 [g]

4.38 (25)

3.91 [g] 3.54 (25) [B]

1.2 (25) [B]

4.59

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Benzonitrile Benzophenone Benzoyl bromide

Viscosity , mN · s · m2 1.447 (15) 1.111 (30) 4.79 (55) 1.38 (120) 1.956 (20) 1.798 (25)

Benzoyl chloride Benzyl acetate Benzyl alcohol

Benzylamine Benzyl benzoate Benzyl butyl o-phthalate Benzyl chloride Benzylethylamine Benzyl ethyl ether Biphenyl Bis(2-ethoxyethyl)ether Bis(2-hydroxyethyl)ether 1,2-Bis(methoxyethoxy)-ethane Bis(2-methoxyethyl) ether DL-Bornyl acetate 3-Bromoaniline

1.399 (45) 5.58 (20) 4.65 (30) 3.01 (45) 1.59 (25) 8.51 (25) 65 (20) 1.400 (20) 1.290 (25)

38.0 (20) 30.0 (25)

Dipole moment, D

a

b

26.5 (20) 24.0 (40) 14.60 (18) 11.4 (50) 21.33 (20) 20.74 (25) 29 (0) 23 (20) 5.1 (21) 13.0 (20) 9.5 (70)

4.40 [g] 3.9 (20) [B] 3.09 (50) [lq] 2.98 (25) [B] 3.40 (20) [B]

41.69

0.115 9

46.31

0.112 8

45.85

0.139 7

3.16 (25) [B]

41.34

0.108 4

1.80 (25) [B] 1.67 (25) [B]

38.25

0.138 1

5.5 (1) 4.6 (21) 4.9 (20)

1.15 (20) [lq] 1.38 (25) [B] 2.06 (30) [B]

42.33

0.121 3

48.07

0.106 5

7.0 (13)

1.83 (20) [B]

39.92

0.122 7

0 1.92 (25) [B]

32.83 (20) 41.52 29.74

29.97 (40) 0.093 1 0.117 6

2.31 (20) [B]

46.97

0.088 0

1.97 (25) [B]

32.47

0.116 4

38.14

0.116 0

28.71

0.112 6

27.48

0.110 7

40.03

0.100 2

4.3 (20) 3.9 (20) 2.53 (75)

31.69 (20)

3.76 (20) 1.99 (20)

0.981 (25) 6.81(20) 3.70 (40) 4-Bromoaniline 1.81 (80) Bromobenzene 1.196 (15) 0.985 (30) 1-Bromobutane 0.633 (20) 0.597 (25) DL-2-Bromobutane 1.434 (20) 1-Bromo-2chlorobenzene 1-Bromo-3chlorobenzene 1-Bromo-4chlorobenzene

Dielectric constant, 

4.6 (21) 13.0 (19)

1.89 (22) 2.67 (20) [B]

7.06 (30) 5.40 (25)

6.80 (20)

2.88 (25) [B] 1.70 [g] 1.50 (20) [lq] 2.17 [g] 2.04 (20) [lq] 2.22 [g] 2.14 (25) [lq] 2.15 (20) [B]

4.58 (20)

1.52 (22) [B]

7.88 (10) 7.07 (20) 8.64 (25)

0.1 (25) [B]

4.60

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

Bromochloromethane Bromocyclohexane 1-Bromodecane

Viscosity , mN · s · m2

1-Bromo-2ethoxyethane 1-Bromo-2ethoxypentane 2-Bromo-2ethoxypentane 3-Bromo-3ethoxypentane Bromoethylene Bromoform

b

1.66 (25) [B]

33.32 (20)

2.0 (25)

11 (65) 7.9 (25) 4.75 (1) 4.44 (25)

1.08 (25) [lq] 2.3 (25) [B] 2.08 (20) [lq] 1.90 (25) [lq] 1.31 (25) [B]

36.13

0.111 7

31.26

0.085 6

35.11

0.129 4

32.58

0.088 2

26.52

0.115 9

31.98

0.112 9

48.14

0.130 8

30.74

0.098 2

33.37

0.086 1

29.81

0.096 7

26.52

0.115 9

28.10

0.099 6

4.07 (25) 0.397 (20) 0.348 (30)

2.152 (15) 1.741 (30)

13.6 (60) 9.39 (20)

2.01 (25) [lq] 1.89 (25) [B] 2.03 [g] 2.04 (20) [lq]

6.45 (25)

2.32 (25) [B]

6.40 (25)

2.07 (25) [B]

8.24 (25)

2.15 (25) [B]

4.78 (25) 4.39 (20)

1.42 [g] 1.00 [g] 0.92 (25) [lq] 2.17 [g] 2.02 (20) [lq] 2.08 (20) [B] 2.06 (20) [B] 2.06 (20) [B] 1.98 (20) [lq] 1.96 (25) [C] 2.06 (20) [lq]

5.33 (25) 4.48 (90) 6.46 (22) 6.93 (22) 6.81 (22) 3.71 (25)

2-Bromoheptane 3-Bromoheptane 4-Bromoheptane 1-Bromohexadecane 1-Bromohexane

6.30 (1) 5.82 (25) 9.82 (0) 1.79 [g] 1.006 8 (100) [g] 8.04 (56) 1.95 (20) [B] 6.05 (20) 6.5 (20)

Bromomethane

1-Bromonaphthalene 1-Bromononane

a

7.79

1-Bromoheptane

1-Bromo-3methylbutane 2-Bromo-3methylbutyric acid 1-Bromo-2methylpropane

Dipole moment, D

0.670 (20)

Bromodichloromethane 1-Bromododecane Bromoethane

Dielectric constant, 

0.643 (20) 0.518 (40) 3.26 (90) 5.99 (15) 3.20 (40)

7.70 (0) 7.2 (25)

1.92 (25) [lq] 1.99 (20) [B]

26.96

0.105 9

5.83 (25) 5.12 (20) 5.42 (20) 4.74 (25)

1.29 (25) [lq]

46.44

0.101 8

1.95 (25) [lq]

31.36

0.089 4

4.61

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Viscosity , mN · s · m2

Dielectric constant, 

Dipole moment, D

1-Bromooctane

6.35 (50)

1.99 (20) [lq] 1.88 (25) [lq]

31.00

0.092 8

1-Bromopentadecane 1-Bromopentane

3.9 (20) 9.9 (90) 6.32 (25)

2.21 [g] 2.09 (20) [lq]

29.51

0.104 9

8.09 (25)

2.17 [g] 3.16 (20) [lq] 2.21 [g] 2.10 (25) [lq] 1.92 (20) [lq] 1.83 (25) [lq] 1.45 (20) [B] 1.77 (20) [B] 1.95 (20) [B] 0.65 [g]

48.88 28.30

0.107 0 0.121 8

26.21

0.118 3

32.93

0.087 8

36.62

0.099 8

36.40 4 (25)

0.099 7

31.94 14.87

0.086 1 0.120 6

Substance

p-Bromophenol 1-Bromopropane 0.539 (15) 0.459 (30) 2-Bromopropane 0.536 (15) 0.437 (30) 1-Bromotetradecane o-Bromotoluene 1.3 (25) m-Bromotoluene p-Bromotoluene Bromotrifluoro- 0.15 (25) methane 1-Bromoundecane Butane 0.007 39 (20) [g] 0.008 39 (60) [g] 1,3-Butanediol 130.3 (20) 89 (25) 1,4-Butanediol 65–70 (25) 2,3-Butanediol Butanesulfonyl chloride 1-Butanethiol

9.46 (25) 3.84 (25) 4.28 (58) 5.36 (58) 5.49 (58)

4.73 (9) 0 28.8 (25) 33 (15) 30 (30)

3-Butenenitrile 2-Butoxyethanol 3.15 (25) 1.51 (60) Butoxyethyne

b

37.8 (25) 3.93 (20) [lq] 2.4 (15) [D]

121 (25)

0.501 (20) 0.450 (30) 1,2,4-Butanetriol 1227 (25) 1-Butanol 2.948 (20) 1.782 (40) DL-2-Butanol 3.907 (20) 0.527 (100) 2-Butanone 0.428 (20) 0.349 (40) 2-Butanone oxime 1-Butene [g] 0.007 6 (20) 0.010 0 (120) 2-Butene

a

3.94 (25) [D]

36 (25) 37.33

0.097 7

5.07 (25) 4.59 (50)

1.54 (25) [lq] or [B]

28.07

0.114 2

17.8 (20) 8.2 (118) 16.6 (25)

1.66 [g] 20 [B] 1.66 (30) [B]

27.18

0.089 8

23.47 (20)

22.62 (30)

18.5 (20) 15.3 (60) 3.4 (20) 1.003 2 (20)

3.2 (30) [lq] 2.76 (25) [B]

26.77

0.112 2

31.89 15.19

0.102 2 0.132 3[lq]

16.11

0.128 9

31.40 28.18

0.108 5 0.081 6

0.30

28.1 (20) 9.30 (25)

0.33 [g, cis] 0 [g, trans] 4.53 [g] 2.08 (25) [B]

6.62 (25)

2.05 (25) [Iq]

4.62

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance 2-(2-Butoxyethoxy)ethanol 1-Butoxy-2propanol Butyl acetate

Viscosity , mN · s · m2

Dielectric constant, 

Dipole moment, D

4.76 (25)

30.0 (25)

2.55 (25)

26.5 (25)

0.734 (20) 0.688 (25)

6.85 (73) 5.01 (20)

1.86 (22) [B]

DL-sec-Butyl

acetate tert-Butyl acetate Butylamine sec-Butylamine tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl butyrate Butyl decyl o-phthalate N-Butyldiethanolamine 4-tert-Butyl-2,5dimethylphenol 4-tert-Butyl-2,6dimethylphenol 6-tert-Butyl-2,4dimethylphenol 6-tert-butyl-3,4dimethylphenol N-Butylethanolamine Butyl ethyl ether Butyl formate

a

0.681 (20)

27.55

0.106 8

23.33 (22)

21.24 (42)

24.69 26.24

0.110 2 0.112 2

23.75 19.44 31.28

0.105 7 0.102 8 0.102 5

2.36 (20)

1.91 (25) [B] 1.00 [g] 1.22 (20) [lq] 1.28 (25) [B] 1.29 (25) [B] 0.36 (20) [lq]

2.36 (20) 2.37 (20)

0.37 (20) [lq] 0.36 (20) [lq]

30.48 30.10 27.65

0.097 9 0.098 5 0.096 5

1.24

22.75

0.104 9

2.08 (26) [lq] 2.03 (25) [B] 1.25 (25) [B] 1.31 (20) [B]

27.08

0.102 6

22.17

0.105 7

2.99 (20) [B]

30.35

0.112 6

1.79 (22) [B]

27.37

0.099 3

4.88 (20) 4.4 (21)

1.035 (20) 0.960 (25)

b

0.84 (25) 55 (20) 55 (25) 8.30 (80) 2.72 (80) 2.10 (80) 3.50 (80) 17.4 (25) 0.421 (20) 0.397 (25) 0.691 (20) 0.940 (0)

Butyl methyl ether 2-tert-Butyl-42.55 (80) methylphenol Butyl nitrate 2-(2-sec-Butylph- 65.1 (25) enoxy)ethanol 2-(4-tert-Butylph- 122.5 (25) enoxy)ethanol Butyl propionate

2.43 (80)

13 (20)

4.63

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance 4-tert-Butylpyridine Butyl stearate Butyl vinyl ether Butyraldehyde Butyric acid Butyric anhydride 4-Butyrolactone Butyronitrile

Viscosity , mN · s · m2

8.26 (25) 4.9 (50) 0.5 (20) 0.455 (20) 0.367 (39) 1.540 (20) 0.980 (40) 1.615 (20) 1.486 (25) 1.75 (25) 0.624 (15) 0.515 (30)

Carbon disulfide

0.363 (20)

Carbon tetrachloride Carbon tetrafluoride Carvone Chloroacetic acid

0.965 (20) 0.793 (25) 0.020 (25)

3.15 (50) 1.92 (75) 0.925 (25)

1-Chlorobutane

0.799 (20) 0.631 (40) 0.469 (15)

2-Chlorobutane

0.439 (15)

Chlorocyclohexane Chlorodifluoromethane 1-Chlorododecane

Dipole moment, D

a

2.87 (25) [C]

35.48

0.095 1

3.11 (30)

1.88 (24) [B]

33.0 (25)

32.7 (30)

13.4 (26)

1.25 (25) [H] 2.45 (40) [lq]

21.99 (20) 26.67

0.092 5

2.97 (20)

1.65 (30) [B]

28.35

0.092 0

28.93 (20)

28.44 (25)

1.495 (20)

Camphor

o-Chloroaniline m-Chloroaniline p-Chloroaniline Chlorobenzene

Dielectric constant, 

0.23 (25) 0.013 (25) [g]

13 (20) 39.1 (20) 20.3 (21)

4.12 (25) [B] 4.07 [g] 3.6 (20) [B]

29.51

0.103 7

11.35 (20)

2.91 (20) [B] 3.10 (25) [B] 0 [g] 0.12 (20) [lq] 0

35.29

0.148 4

29.49

0.122 4

0

14 (73)

2.8 (15) [B] 2.31 (30) [B]

36.54 43.27

0.092 0 0.111 7

1.78 (20) [B] 2.68 (20) [B] 2.99 (25) [B] 1.72 [g] 1.56 (20) [lq] 2.13 [g] 2.0 (20) [B] 2.14 [g] 2.1 (20) [B] 2.2 (25) [B]

43.41

0.090 4

48.69 35.97

0.109 9 0.119 1

25.97

0.111 7

24.40

0.111 8

33.90

0.110 1

3.0 (112) 2.64 (20) 2.24 (20) 2.23 (25) 1.000 6 (25) [g] 11 (22) 20 (20) 12.3 (60) 13.4 (25) 13.4 (19) 5.71 (20) 4.2 (120) 9.07 (30) 7.39 (20) 7.09 (30) 10.9 (47) 7.6 (25) 6.11 (24) 4.2 (20)

1-Chloro-2-2,3epoxypropane Chloroethane

1.03 (25)

2-Chloroethanol

3.913 (15)

0.279 (10)

b

25.6 (1) 22.6 (22) 1.013 (19) [g] 25.8 (25) 13 (132)

1.4 [g]

8 (25)

2.11 (25) [lq] 1.94 (20) [B] 1.8 (25) [C]

31.56

0.090 4

39.76

0.136 0

21.18 (5)

20.58 (10)

2.0 [g] 1.96 (20) [lq] 1.77 [g] 1.90 (25) [B]

38.9 (20)

4.64

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Chloroform 1-Chloroheptane 2-Chloroheptane 3-Chloroheptane 4-Chloroheptane 1-Chlorohexane Chloromethane [g] [lq] 1-Chloro-3methylbutane Chloromethyl methyl ether l-Chloro-2methylpropane 2-Chloro-2methylpropane 1-Chloronaphthalene o-Chloronitrobenzene m-Chloronitrobenzene p-Chloronitrobenzene 1-Chlorooctane Chloropentafluoroethane 1-Chloropentane o-Chlorophenol m-Chlorophenol p-Chlorophenol 1-Chloropropane 2-Chloropropane 1-Chloro-2propanone 3-Chloro-1propene

Viscosity , mN · s · m2 0.596 (15) 0.514 (30)

0.0106 (20) 0.012 9 (80)

Dielectric constant,  4.81 (20) 4.31 (50) 4.48 (20) 6.52 (22) 6.70 (22) 6.54 (22)

Dipole moment, D 1.1 [g] 1.1 (25) [lq] 1.86 (22) [B] 2.05 (22) [B] 2.06 (22) [B] 2.06 (22) [B] 1.94 (20) [B]

a

b

29.91

0.129 5

28.94

0.096 1

28.32

0.103 8

19.5 25.51

0.165 0 0.107 6

2.06 [g] 2.0 (25) [B] 2.11 [g] 2.13 (25) [B] 1.33 (25) [lq] 1.52 (25) [B] 4.62 [g] 6.22 (50) [lq] 3.72 [g] 3.30 (50) [lq] 2.81 [g] 2.83 (90) [lq] 2.14 (25) [lq] 0.5 [g]

24.40

0.109 9

20.06 (15)

18.35 (30)

44.12

0.103 5

48.10

0.117 1

49.71

0.141 7

45.84

0.104 6

29 64 5 (25)

0.096 1

2.14 [g] 1.94 (20) [B] 2.19 [g] 1.46 (20) [lq] 2.19 (25) [B]

27.09

0.107 6

42.5

0.112 2

43.7

0.100 9

2.09 (20) [B] 2.05 [g] 1.96 (20) [B] 2.17 [g] 2.1 (20) [B] 2.22 [g] 2.37 (20), [H] 2.0 [g] 1.8 (20) [B]

19.51 24.41

0.087 5 0.124 6

21.37

0.088 3

25.50

0.094 6

1.006 9 (100)

1.87

12.6 (20) 7.63 (70) 6.05 (20)

1.86 (20) 1.94 (20) [B] 1.88 [C]

0.462 (20) 0.373 (40) 0.543 (15) 2.940 (25)

7.87 (38) 6.49 (14) 10.95 (0) 9.96 (20) 5.04 (25) 38 (50) 32 (80) 21 (50) 18 (80) 8 (120) 5.05 (25)

0.26 (25) 0.013 (25) [g] 0.580 (20) 2.250 (45) 4.11 (25) 4.722 (45) 11.55 (25) 4.99 (50) 0.372 (15) 0.318 (30) 0.335 (15) 0.299 (30)

6.6 (11) 6.31 (25)

7.7 (20) 9.82 (20) 30 (19)

0.347 (15)

8.2 (20)

4.65

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

Viscosity , mN · s · m2

o-Chlorotoluene m-Chlorotoluene p-Chlorotoluene Chlorotrifluoromethane Chlorotrimethylsilane Cinnamaldehyde

0.016 (25)

o-Cresol

3.506 (46)

m-Cresol

18.42 (20) 5.057 (45) 5.607 (45)

p-Cresol Crotonic acid Cyanoacetic acid Cycloheptanol 1,3-Cyclohexadiene Cyclohexane Cyclohexanecarboxylic acid 1,4-Cyclohexanedione Cyclohexanol Cyclohexanone Cyclohexanone oxime Cyclohexene Cyclohexylamine Cyclohexylbenzene Cyclohexylmethanol o-Cyclohexylphenol

Dielectric constant, 

Dipole moment, D

4.45 (20) 4.2 (55) 5.5 (20) 5.0 (60) 6.08 (20) 5.6 (55) 1.001 3 (29) [g]

1.57 [g] 1.41 (20) [lq] 1.77 (20) [lq] 1.8 (22) [B] 2.21 [g] 1.90 (20) [lq] 0.50 [g]

14 (73)

2.09 (20) [B]

19.51

0.087 5

39.43

0.101 1

38.00

0.092 4

38.58

0.096 2

35.02

0.092 3

17 (20) 16.9 (24) 11.5 (25) 11.8 (25) 9.91 (58)

3.74 [g] 3.30 (30) [lq] 2.32 (25) [lq] 1.45 (25) [B] 2.39 (20) [lq] 1.61 (25) [B] 2.35 (20) [lq] 1.54 (20) [B] 2.13 (30) [B]

a

34.93

b

0.108 2

33.4 (19)

0.980 (20) 0.534 (60)

2.6 (89)

0.38 (20) [B]

2.05 (15) 2.02 (25) 2.6 (31)

0

27.62

0.118 8

15.0 (25)

1.41 [g] 1.3 (30) [B] 1.86 (25) [C]

35.33

0.096 6

3.11 (20) [B] 3.01 (25) [B] 0.83 (25) [B]

37.67

0.124 2

29.23

0.122 3

34.19

0.118 8

41.07 (30) 17.19 (45) 2.453 (15) 1.803 (30)

15.0 (25) 7.24 (100) 20 (40) 18.2 (20) 3.0 (89)

0.650 (20)

2.6 (105) 2.22 (25) 4.73 (20)

0.61 [g] 0.28 (20) [lq] 1.22 (20) [lq] 1.26 (20) [B] 0.62 (20) [B]

9.7 (60) 8.1 (80) 3.97 (55)

1.68 (20) [B]

1.662 (20) 1.16 (49) 3.681 (0)

4.66

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance p-Cyclohexylphenol Cyclooctane Cyclopentane Cyclopentanol

Viscosity , mN · s · m2

cis-Decahydronaphthalene trans-Decahydronaphthalene Decamethylcyclopentasiloxane Decamethyltetrasiloxane Decane

0.439 (20)

a

b

1.965 (20) 25 (20) 18 (20) 16 (51)

0 0 1 72 (25) [C]

32.02 25.53 35.04

0.109 0 0.146 2 0.101 1

35.55

0.110 0

25.94 28.83

0.149 5 0.087 7

3.402 (20)

2.243 (20)

3.30 [g] 2.93 (25) [B] 0.98 (25) [H] 0 [lq]

3.381 (20)

2.18 (20)

0

32.18 (20)

31.01 (30)

2.128 (20)

2.17 (20)

0

29.89 (20)

28.87 (30)

19.56

0.056 5

2.5 (20) 1.28 (20)

2.4 (20)

0.79 (25) [lq]

86.20 (25)

0.928 (20) 0.775 (22)

1.991 (20) 1.844 (130) 8.1 (20)

0

25.67

0.092 0

1.71 (20) [B] 1.62 (25) [B] 0.42 (20) [B] 1.33 (25) [B] 0.88 (25) [B] 0.97 (20) [lq] 1.02 (20) [B]

30.34

0.073 2

25.84

0.091 9

43.27

0.108 6

1-Decanol 1-Decene Diallyl sulfide Dibenzofuran Dibenzylamine

Dipole moment, D

4.42 (131)

Cyclopentanone Cyclopentene p-Cymene

Dielectric constant, 

0.805 (20) 4.9 (20) 3.0 (100) 3.6 (20)

Dibenzyl decanedioate Dibenzyl ether 3.711 (25) o-Dibromobenzene m-Dibromobenzene p-Dibromobenzene 1,4-Dibromobutane

4.6 (25)

2,3-Dibromobutane

5.75 (25)

1,2-Dibromoethane 1.721 (20) 1.286 (40) cis-1,2-Dibromoethylene trans-1,2-Dibromoethylene 1,2-Dibromoheptane

4.78 (25) 4.09 (131) 7.7 (0) 7.08 (25) 2.9 (0) 2.88 (25)

7.35 (20) 3.80 (20) 2.57 (95)

3.8 (25)

1.39 (21) [B] 2.13 (20) [B] 1.5 (20) [B] 0 2.16 (20) [lq] 2.06 (20) [B] 2.20 [g] 1.7 (25) [lq] 1.11 [g] 1.14 (20) [lq] 1.35 (B) 0

1.78 (25) [D]

38.2 (35)

41.84 48.24

0.100 7 0.119 0

35.43

0.142 8

4.67

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

Viscosity , mN · s · m2

2,3-Dibromoheptane 3,4-Dibromoheptane Dibromomethane

Dielectric constant, 

Dipole moment, D

5.1 (25)

2.15 (25) [B]

4.7 (25)

2.15 (25) [B]

1.5 (25)

7.77 (10) 6.7 (40) 4.3 (20)

1.43 [g] 1.85 (20) [lq] 1.43 (25) [B]

0.72 (25)

2.34 (25)

0.95 (20)

2.978 (20)

Dibutyl decanedioate Dibutyl ether

9.03 (25)

4.54 (30)

0.602 (30)

3.06 (25)

Dibutyl maleate

5.62 (20) 4.76 (25) 3.47 (80)

1,2-Dibromopropane Dibromotetrafluoroethane Dibutylamine

2,6-Di-tert-butyl4-methylphenol Dibutyl o-phthalate Dichloroacetic acid o-Dichlorobenzene

19.91 (20) 7.85 (45) 3.23(50) 1.92 (75) 1.324 (25)

m-Dichlorobenzene 1.045 (23) 0.955 (33) p-Dichlorobenzene 0.839 (55) 0.668 (79) 1,4-Dichlorobutane Dichlorodifluoro0.26 (25) methane 0.013 (25) [g] 1,1-Dichloroethane 0.505 (25) 0.430 (30) 1,2-Dichloroethane 0.887 (15) 0.730 (30) 1,1-Dichloroe0.442 (0) thylene 0.358 (20) cis-1,2-Dichlo0.467 (20) roethylene 0.444 (25) trans-1,2-Dichlo0.423 (15) roethylene 0.404 (20)

a

b

42.77

0.148 8

36.81

0.115 5

18.9 (20)

18.1 (25)

1.06 (20) [lq] 1.05 (20) [B] 2.64 (25) [B]

26.50

0.095 2

1.18 [g] 1.19 (20) [lq] 2.70 (25) [B]

24.78

0.093 4

32.46

0.086 5

1.68 (20) [B] 6.436 (30) 5.99 (45) 8.2 (22) 7.8 (61) 9.93 (25) 7.10 (90) 5.04 (25) 4.22 (90) 2.41 (50)

2.97 (20) [lq] 2.85 (30) [B]

8.9 (25) 2.13 (29)

2.22 [g] 2.13 (25) [lq] 0.51 [g]

10.1 (18) 10.86 (16) 12.7 (10) 10.65 (20) 4.67 (16)

2.06 [g] 2.00 (25) [B] 1.48 [g] 1.7 (20) [B] 1.30 (25) [B]

27.03

0.118 6

35.43

0.142 8

9.20 (25)

2.95 [g] 1.90 (25) [B] 0.70 (25) [B]

28 (20)

2.14 (25)

2.51 [g] 2.26 (24) [B] 1.68 [g] 1.38 (24) [B] 0

33.40 (20) 37.8

0.092 7

26.84 (20)

35.55 (30)

38.30

0.114 7

34.66

0.087 9

37.79

0.117 4

9 (25)

25 (20)

4.68

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance 2,2 -Dichloroethyl ether Dichlorofluoromethane Dichloromethane 2,4-Dichlorophenol 1,2-Dichloropropane 1,3-Dichloropropane 2,2-Dicloropropane 1,1-Dichloro-2propanone 1,2-Dichlorotetrafluoroethane ,-Dichlorotoluene Diethanolamine

Viscosity , mN · s · m2 2.41 (20) 2.065 (25) 0.34 (25) 0.011 (25) [g] 0.449 (15) 0.393 (30)

0.865 (20) 0.700 (25)

0.769 (15) 0.619 (30)

Dielectric constant, 

Dipole moment, D 2.61 (20) [B]

40.57

5.34 (28)

1.3 [g]

18 (25)

9.14 (20) 1.006 5 (100) [g]

1.60 [g] 1.90 (20) [B] 1.60 (25) [B]

30.41

0.128 4

46.59

0.122 1

8.925 (26) 7.90 (35)

1.87 (25) [B]

31.42

0.124 0

2.08 [g] 2.2 (25) [B] 2.62 [g] 2.20 (25) [B]

36.40

0.123 3

23.60 (20)

22.53 (30)

11.37 (20)

0.38 (25) 0.011 (25) [g]

2.26 (25)

0.53 [g]

12 (25)

6.9 (20)

2.07 (20) [B] 2.05 (25) [B] 2.84 (25) [B]

41.26

0.103 5

23.46

0.103 0

23.87 22.71

0.129 1 0.114 3

36.59

0.104 0

28.62

0.110 0

34.68

0.095 9

18.92

0.090 8

30.63

0.097 5

34.34

0.101 0

1,1-Diethoxyethane 1,2-Diethoxyethane 0.65 (20)

3.80 (25)

1.08 [g] 1.99 (20) [B] 1.65 (25) [B]

3.6 (22)

0.92 [g] 1.11 (25) [lq] 1.40 (20) [lq] 1.80 (20) [B] 1.07 [g] 0.91 (25) [B] 2.38 (20) [lq] 2.52 (20) [B] 1.15 [g] 1.22 (16) [lq] 2.95 (32) [lq] 2.91 (20) [C] 2.40 (20) [B] 2.46 (30) [lq]

Diethyl decanedioate Diethyl ether Diethyl ethyl phosphonate Diethyl fumarate Diethyl glutarate Di(2-ethylhexyl)2-ethylhexylphosphonate Di(2-ethylhexyl) o-phthalate

0.130 6

14 (20)

2.81 (25)

N, N-Diethylaniline Diethyl carbonate

b

21.2 (20)

368 (30) 196 (40)

Diethoxymethane Diethylamine

a

0.388 (10) 0.273 (38) 1.15 (30) 0.750 (75) 0.868 (15) 0.748 (25)

5.5 (19) 2.82 (20) 5.0 (30)

0.247 (15) 0.245 (20) 1.627 (15) 0.969 (45)

6.00 (45) 3.61 (65)

4.335 (20) 3.97 (40) 11.00 (15) 9.86 (45) 6.5 (23) 6.7 (30) 4.09 (45) 3.94 (65)

33.67 (35) 21.40 (45)

4.91 (35) 4.77 (45)

4.69

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Diethyl maleate Diethyl malonate Diethyl nonanedioate Diethyl oxalate Diethyl o-phthalate Diethyl succinate Diethyl sulfate Diethyl sulfide

Viscosity , mN · s · m2 3.57 (20) 3.14 (25) 2.15 (20) 1.94 (25)

Dipole moment, D

a

8.58 (23)

2.56 (25) [B]

34.67

0.103 9

8.03 (25)

2.49 (20) [lq] 2.54 (25) [B]

33.91

0.104 2

8.1 (21)

2.49 (20) [D]

34.32

0.111 9

7.34 (35) 7.13 (45) 6.64 (30)

2.8 (25) [B]

38.47

0.096 3

2.3 [g] 2.37 (30) [lq] 4.46 (25) [D] 1.52 [g] 1.58 (20) [B]

33.97

0.104 1

35.47 27.33

0.097 6 0.110 6

2.60 (25) [B]

47.6

0.084 9

2.09 (44) [B]

54.8

0.071 7

b

5.13 (30) 2.311 (15) 1.618 (30) 9.18 (35) 6.41 (45)

0.446 (20) 0.422 (25)

Diethyl sulfite Diethylzinc 1,1-Difluoroethane 0.243 (21) 1,2-Dihydroxybenzene 1,3-Dihydroxybenzene 1,4-Dihydroxybenzene 1,2-Diiodobenzene 1,3-Diiodobenzene 1,4-Diiodobenzene cis-1,2-Diiodoethylene trans-1,2-Diiodoethylene Diiodomethane 3.043 (15) 2.392 (30) Diisobutylamine Diisobutyl 30 (20) o-phthalate Diisopentylamine Diisopentyl ether 1.40 (11) 1.012 (20) Diisopropylamine 0.40 (25) Diisopropyl ether 0.379 (25) 1,2-Dimethoxybenzene

Dielectric constant, 

3.281 (25) 2.184 (40)

29 (20) 5.72 (25) 5.24 (50) 16 (20) 14 (50) 2.5 (20) 2.30 [g] 2.6 (89) 3.2 (18)

0.62 (25) [B]

1.4 (44) [B] 5.7 (20) 4.3 (25) 2.9 (120) 4.46 (83)

1.70 (20) [B] 1.22 (20) [B] 0.19 (20) [B] 0.71 [B]

2.19 (83)

0

5.316 (25)

1.08 (25) [B]

70.21

0.161 3

2.7 (22)

1.10 (25) [B]

24.00

0.091 2

2.5 (18) 2.82 (20)

1.48 (30) [B] 0.98 (20) [lq] 1.23 (25) [B] 1.26 (25) [B] 1.13 [g] 1.26 (25) [B] 1.32 (25) [B]

26.04 24.76

0.085 8 0.087 1

21.83 19.89

0.107 7 0.104 8

34.4

0.064 2

3.88 (25) 4.09 (25)

4.70

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance 1,1-Dimethoxyethane 1,2-Dimethoxyethane Dimethoxymethane N,N-Dimethy lacetamide Dimethylamine N,N-Dimethylaniline 2,4-Dimethylaniline 2,2-Dimethylbutane 2,3-Dimethylbutane 2,3-Dimethyl-1butanol N,N-Dimethylbutyramide Dimethyl carbonate 1,1-Dimethylcyclopentane 2,2-Dimethyl-1, 3-dioxolane4-methanol Dimethyl ether N,N-Dimethylformamide 2,4-Dimethylheptane 2,5-Dimethylheptane 2,6-Dimethylheptane 2,6-Dimethyl-4heptanone Dimethyl hexanedioate Dimethyl hydrogen phosphonate

Viscosity , mN · s · m2

Dielectric constant, 

Dipole moment, D

a 23.90

0.530 (10) 0.455 (25) 0.340 (15) 0.325 (20) 2.141 (20) 0.838 (30) 0.207 (15) 0.186 (25) 1.285 (25) 0.91 (50)

0.351 (25) 0.330 (30) 0.361 (25) 0.342 (30)

1.271

0.845 (20) 0.598 (50)

1.71 (25) [B]

48.0 (25)

0.74 [g]

23.59

0.119 9

37.78 (25)

3.80 [g] 4.60 (20) [lq] 1.03 [g] 1.14 (25) [lq] 1.61 [g] 1.55 (25) [B] 1.40 (25) [B]

32.43 (30)

29.50 (50)

29.50

0.126 5

38.14

0.104 9

39.34

0.099 6

6.32 (0) 5.26 (25) 4.9 (20) 4.4 (70)

1.873 (25)

0

18.29

0.099 0

1.890 (25)

0

19.38

0.100 0

26.22

0.099 2

31.94

0.134 3

23.78

0.101 6

2.00

5.02 (25) 2.97 (110) 38.3 (20) 36.71 (25) 1.9 (20)

1.30 [g] 1.25 (25) [B] 3.86 (25) [B]

14.97

0.147 8

36.76 (20)

34.40 (40)

0

23.21

0.092 9

1.9 (20)

0

23.21

0.092 9

2 (20)

0

22.77

0.088 7

38.26

0.113 8

1.03 (20)

2.66 (25) [C]

14 (20)

2.28 (20) [B]

1.08 (25)

0.115 9

7.60 (10) 7.20 (25) 2.65 (20)

0.90 [g] 0.96 (25) [B] 0

11 (20) 0.010 4 (60)

b

4.71

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Dimethyl maleate Dimethyl malonate 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,4-Dimethylphenol 2,5-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol Dimethyl o-phthalate 2,2-Dimethylpropane N,N-Dimethylpropionamide 2,5-Dimethylpyrazine 2,3-Dimethylquinoxaline Dimethyl succinate Dimethyl sulfate Dimethyl sulfide Dimethyl sulfite Dimethyl sulfoxide 2,4-Dimethyltetrahydrothiophene-1, 1dioxide

Viscosity , mN · s · m2

Dielectric constant, 

Dipole moment, D

a

2.48 (25) [C]

40.73

0.122 0

10 (20) 1.91 (20)

2.41 (20) [B] 0

39.72 19.94

0.120 8 0.095 7

0.406 (20)

1.939 (20)

0

21.96

0.099 5

0.361 (20)

1.914 (20)

0

20.09

0.097 2

1.94 (20)

0

21.59

0.099 6

34.57

0.086 9

36.72

0.085 0

4.8 (17)

1.48 (20) [B] 1.98 (60) [B] 1.43 (20) [B] 1.52 (60) [B] 1.77 (20) [B]

35.75

0.091 0

1.76 (20) [B]

34.09

0.080 7

12.05 (20)

10.98 (30)

3.54 (20) 3.21 (25)

1.55 (80) 3.00 (80) 2.42 (80) 17.2 (25) 6.41 (45) 0.328 (0) 0.303 (5) 0.935

b

8.25 (25) 8.11 (45) 1.80 (20) 1.678 (98) 33.1

2.8 (25) [B] 0

2.43 (20)

0

2.3 (25)

0

5.1 (20)

2.09 (20) [B]

39.00

0.119 1

48.3 (20) 46.4 (20) 6.2 (20)

4.31 (25) [D]

41.26

0.116 3

1.45 (25) [B]

26.07

0.080 5

0.289 (20) 0.265 (36) 0.715 (30) 0.436 (80) 2.47 (20) 1.192 (55)

22.5 (23)

2.93 (20) [B]

36.48

0.125 3

48.9 (20) 41.9 (55)

3.9 (25) [B]

43.54 (20)

42.41 (30)

9.04

29.5

4.72

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance N,N-Dimethylo-toluidine N,N-Dimethylp-toluidine Dinonyl hexanedioate Dinonyl o-phthalate Dioctyl decanedioate Dioctyl o-phthalate 1,4-Dioxane Dipentyl ether Dipentyl o-phthalate Dipentyl sulfide Diphenylamine 1,2-Diphenylethane Diphenyl ether

Viscosity , mN · s · m2

Dipropyl carbonate Dipropylene glycol butyl ether Dipropylene glycol ethyl ether Dipropylene glycol isopropyl ether

Dipole moment, D

3.4 (20)

0.88 (25) [B]

3.9 (20)

1.29 (25) [B]

37 (20)

a

b

2.53 (25) [B] 4.65 (35) 4.52 (45) 4.0 (27)

1.439 (15) 1.087 (30) 1.188 (15) 0.922 (30) 17.03 (35) 11.51 (45) 4.66 (55) 1.04 (130)

5.1 (25)

3.06 (25) [C]

2.24 (20) 2.21 (25) 2.77 (25)

0

36.23

0.139 1

0.98 (20) [lq] 1.24 (25) [B] 2.71 (20) [lq]

26.66

0.092 5

32.56

0.073 9

29.55 45.36

0.087 6 0.101 7

3.65 (30)

1.59 (25) [B] 1.31 (20) [C] 1.01 (25) [B] 0 (110) [lq] 0.45 (25) [B] 1.16

28.70

0.078 0

2.7 (18) 2.57 (26)

0.26 (30) [lq] 0.3 (25) [B] 25.03

0.097 2

25.17

0.095 3

24.86

0.102 2

28.94

0.101 5

5.79 (35) 5.62 (45) 3.83 (25) 3.3 (52) 2.4 (110)

2.61 (40) 2.09 (50)

Diphenylmethane 1,1-Dipropoxyethane Dipropoxymethane Dipropylamine

Dielectric constant, 

0.534 (20) 0.427 (37)

3.07 (20)

1.01 (20) [lq] 1.03 (20) [B]

4.23 (25)

28.2 (25)

3.11 (25)

27.7 (25)

386 (25)

25.9 (25)

4.73

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Dipropylene glycol methyl ether Dipropyl ether Divinyl ether Dodecamethylcyclohexasiloxane Dodecamethylpentasiloxane Dodecane

Viscosity , mN · s · m2

0.448 (15) 0.376 (30)

1,2-Ethanediamine 1,2-Ethanediol 1,2-Ethanediol diacetate Ethanesulfonic acid Ethanesulfonyl chloride Ethanethiol Ethanol Ethoxybenzene 2-Ethoxyethanol 2-(2-Ethoxyethoxy)ethanol 2-Ethoxyethyl acetate

3.39 (26)

1.21 [g] 1.17 (30) [H] 1.07 (20) [lq]

2.5 (20) 1.508 (20) 1.378 (25)

2.05 (10) 2.01 (20) 5.15 (20) 6.5 (25) 2.17 (25)

22.60

0.104 7

17.08 (25) 27.12

0.088 4

1.52 (20) [B]

31.25

0.0748

2.01 (20) [B]

23.9 (20)

28 (128) 1.001 5 (0)

0

1.24

0.166 0 [lq]

16.8 (18) 14.2 (20) 38.66 (20) 37.7 (25) 13 (30)

1.96 [g] 1.92 (25) [B] 2.28 [g] 2.3 (25) [D] 2.34 (30) [B]

44.77

0.139 8

50.21

0.089 0

45.74

0.082 4

3.89 (25) [B]

43.43

0.117 7

1.57 [g] 1.40 (20) [B] 1.69 [g] 1.71 (25) [B] 1.41 [g] 1.36 (25) [CS2] 2.24 (30) [B]

25.06

0.079 3

24.05

0.083 2

35.17

0.110 4

30.59

0.089 7

31.8 (25)

27.2 (75)

0.003 16 [g]

6.9 (15)

1.209 (19) 0.991 (30) 1.364 (15) 1.040 (30) 2.04 (20) 1.85 (25) 3.71 (25)

25.00 (20) 20.21 (55) 4.22 (20)

1.025 (25)

b

0

0.41 (20) 0.40 (25) 0.009 0 (20) 0.011 4 (100) 1.54 (20) 1.226 (30) 26.09 (15) 13.55 (30) 3.13 (20)

a

28.8 (25)

3.9 (20) 2.6 (20)

6-Dodecyne

Erythritol Ethane [g]

Dipole moment, D

3.1 (25)

1-Dodecanol

1,2-Epoxybutane

Dielectric constant, 

29.6 (24)

7.567 (30)

2.25 (30) [B]

31.8 (25)

4.74

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance 1-Ethoxy-2methylbutane 1-Ethoxynaphthalene 1-Ethoxypentane 1-Ethoxy-2propanol -Ethoxytoluene Ethyl acetate Ethyl acetoacetate

Ethylamine 2-(Ethylamino) ethanol N-Ethylaniline Ethylbenzene Ethyl benzoate Ethyl bromobutyrate 2-Ethyl-1-butanol Ethyl butyrate 2-Ethylbutyric acid Ethyl carbamate Ethyl chloroacetate Ethyl chloroformate Ethyl cinnamate Ethyl crotonate Ethyl cyanoacetate Ethylcyclohexane Ethyl dichloroacetate

Viscosity , mN · s · m2

Dielectric constant, 

Dipole moment, D

a

b

3.96 (20) 3.3 (19) 3.6 (23) 1.68 (25)

0.473 (15) 0.426 (25) 1.419 (20) 1.508 (25)

25.9 (25) 3.9 (20) 6.11 (20) 5.30 (77) 15.7 (22)

6.94 (10)

1.78 [g] 1.84 (25) [lq] 3.22 (18) [B keto form] 2.04 (80) [CS2, enol form] 1.40 (25) [B]

26.29

0.116 1

34.42

0.101 5

22.63

0.137 2

39.00

0.107 0

12.40 (25) 2.04 (25) 1.08 (55) 0.669 (20) 0.531 (40) 2.407 (15) 1.751 (30)

5.76 (20) 2.41 (20)

0.37 (25) [lq]

31.48

0.109 4

6.02 (20)

1.95 [g] 1.93 (25) [B] 2.40 (25) [B]

37.16

0.105 9

25.06 (15)

24.32 (25)

26.55

0.104 5

8 (20) 8.021 (15) 5.892 (25) 0.771 (15) 0.613 (25) 3.3 (20)

6.19 (90)

0.916 (105) 0.715 (120)

14.2 (50)

2.59 (30) [D]

11.4 (21)

2.65 (25) [B]

34.18

0.117 7

11 (20)

2.56 (35) [B]

28.90

0.108 4

6.1 (18) 5.4 (20) 26.9 (20)

1.86 (20) [B] 1.95 (24) [B] 4.04 (30) [B]

39.99 29.31 38.80

0.104 5 0.106 6 0.109 2

2.054 (20)

0 [g]

27.78

0.105 4

12 (2) 10 (22)

2.63 (25) [B]

34.89

0.115 8

8.7 (20) 3.256 (15) 2.148 (30) 0.843 (20) 0.787 (25)

5.10 (18)

1.74 (22) [B]

26.3 (20)

4.75

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Viscosity , mN · s · m2

Dielectric constant, 

Dipole moment, D

a

1.3 (20) [lq]

30.05

0.086 3

0 [g] 4.87 (25) [B]

2.7

0.185 4

1.98 [g] 1.92 (25) [B] 3.58 (25) [B] 5.58 [lq]

44.77

0.139 8

38 (20)

3.4 (20) 2.7 (143) 1.001 44 (0) 89.6 (40) 69.4 (91) 16.0 (18) 14.2 (20) 28.3 (20) 23.69 (20)

49.1 (0) 47.33

46.7 (45) 0.088 0

41.2 (20) 37.7 (25) 14 (1)

0.089 0

27.66

0.166 4

Ethyleneimine

0.418 (25)

18.3 (25)

Ethyl formate

0.419 (15) 0.358 (30)

7.16 (25)

2.27 [g] 2.20 (15) [lq] 1.88 [g] 1.92 (20) [lq] 1.89 [g] 1.77 (25) [B] 1.94 [g] 1.96 (25) [lq]

50.21

Ethylene oxide

26.09 (15) 13.35 (30) 0.3 (0)

Substance N-Ethyldiethanolamine Ethyl dodecanoate Ethylene Ethylene carbonate Ethylenediamine Ethylene dinitrate 2,2 -(Ethylenedioxy)diethanol Ethylene glycol

Ethyl fumarate Ethyl hexadecanoate 2-Ethyl-1, 3hexanediol Ethyl hexanoate 2-Ethylhexanoic acid 2-Ethyl-1-hexanol 2-Ethylhexyl acetate Ethyl isobutyrate Ethyl isopentyl ether Ethyl isothiocyanate Ethyl lactate Ethyl maleate Ethyl 3methylbutyrate Ethyl methyl ether Ethyl methyl sulfide Ethyl nitrate

b

53 (25)

1.85 (40) 1.540 (18)

6.5 (23) 3.2 (20) 2.71 (104)

7.9 (20) 26.47

0.131 5

1.2 [lq]

33.90 32.86

0.105 6 0.085 9

1.80 (20) [B]

27.73

0.096 0

1.74 (25) [B]

30.0 (22)

323 (20)

7.7 (20) 9.8 (20) 1.5 (20)

4.41 (90)

25.33

0.104 6

3.96 (20)

2.44 (25)

19.5 (21)

3.67 (20) [B]

38.69

0.132 6

13.1 (25) 8.6 (23) 4.71 (18)

2.4 (20) [B]

30.72

0.098 3

25.79

0.100 6

18.56

0.131 7

27.63

0.128 6

30.81

0.134 5

1.22 [g] 0.373 (20) 0.354 (25) 19.4 (20)

2.93 (20) [B]

4.76

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

Viscosity , mN · s · m2

Ethyl 9octadecenoate Ethyl 4oxopentanoate 3-Ethylpentane Ethyl pentanoate 0.847 (20) Ethyl pentyl ether Ethyl phenylacetate 5.3 (21) Ethyl phenyl sulfide Ethyl propionate 0.564 (15) 0.473 (30) Ethyl propyl ether 0.323 (20) 0.225 (60) Ethyl salicylate 1.772 (45) Ethyl stearate Ethyl thiocyanate o-Ethyltoluene p-Ethyltoluene Ethyl trichloroacetate Ethyl vinyl ether Ethynyl acetate Fluorobenzene 1-Fluorohexane 2-Fluoro-2methylbutane 1-Fluoropentane o-Fluorotoluene m-Fluorotoluene p-Fluorotoluene Formamide Formanilide Formic acid 2-Furaldehyde Furan

Dielectric constant,  3.2 (25)

0.680 (20) 0.601 (30) 0.608 (20) 0.534 (30) 0.622 (20) 0.522 (30) 4.320 (15) 2.296 (30) 1.65 (120) 1.966 (15) 1.219 (40) 2.475 (0) 1.494 (25) 0.380 (20) 0.361 (25)

a

b

1.83 (20) [lq]

12 (21) 1.94 (20) 4.7 (18) 3.6 (23) 1.82 (30)

0 1.76 (28) [B] 1.2 (20) [B]

22.52 27.15 24.19

0.103 2 0.099 9 0.099 2

4.08 (25) [B]

39.30

0.113 1

1.75 (22) [B]

26.72

0.116 8

1.16 (25) [B]

21.92

0.105 4

7.99 (30) 2.98 (40) 2.69 (100) 29.3 (21)

2.85 (25) [B] 1.65 (40) [lq]

31.00

0.109 1

3.33 (20) [B]

2.24 (25) 7.8 (20)

0 2.56 (25) [B]

37.28 32.33 30.98 32.97

0.122 6 0.106 0 0.107 5 0.107 3

5.65 (19)

0.2 0.620 (15) 0517 (30)

Dipole moment, D

1.26 (20) [B]

19.00 (20) 32.81 (20)

30.20 (40)

5.42 (25) 4.7 (60)

1.61 [g]

29.67

0.120 4

23.41

0.100 1

5.89 (20)

1.92 (25) [B]

4.24 (20) 4.22 (30) 3.9 (60) 5.42 (30) 4.9 (60) 5.86 (30) 5.3 (60) 111.0 (20) 103.5 (40)

1.85 (25) [B] 1.35 [g] 1.26 (30) [lq] 1.86 [g] 1.66 (30) [lq] 2.00 [g] 1.76 (30) [lq] 3.73 [g]

22.81

0.131 5

32.31

0.125 7

30.44

0.110 9

59.13

0.084 2

44.30 39.87

0.087 5 0.109 8

46.41

0.132 7

24.10 (20)

23.38 (25)

58.5 (15) 57.0 (21) 41.9 (20) 34.9 (50) 2.95 (25)

3.37 (25) [C] 1.35 [g] 1.20 (25) [B] 2.13 (25) [lq] 3.63 (25) [B] 0.66 [g] 0.67 (20) [B]

4.77

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

Viscosity , mN · s · m2

Furfuryl alcohol

4.62 (25)

Glycerol

945 (25) 134 (50)

Glycerol triacetate Glycerol trinitrate

36.0 (20) 13.6 (40)

Glycerol trioleate Glycerol tripalmitate Glycerol tristearate

Dielectric constant, 

Dipole moment, D

a

1.92 (25) [lq]

ca 38 (20)

42.5 (25)

2.68 (25) [D]

63.14 (17)

62.5 (25)

7.2 (20) 19 (20)

2.73 (25) [B] 3.38 (25) [B]

37.88 55.74

0.081 0.250 4

3.2 (26) 2.9 (65)

3.11 (23) [B] 2.80 (23) [B]

36.03 32.26

0.069 9 0.067 2

2.8 (70)

2.86 (23) [B]

32.73

0.068 5

2.26 (40) [lq] 2.58 (22) [B] 0

28.64

0.092 0

22.10

0.098 0

29.88

0.084 8

1.73 (20) [B] 1.73 (20) [B] 1.72 (20) [B] 2.61 (22) [B]

28.76

0.105 6

2.81 (22) [B] 2.74 (20) [B]

28.24 28.11

0.101 5 0.106 0

0.34 (20) [lq]

22.28

0.099 1

0 1.67 (25) [B]

29.18

0.085 4

Heptanaldehyde

0.977 (15)

9.1 (20)

Heptane

0.416 (20) 0.341 (40) 3.40 (30) 7.014 (20) 8.53 (15) 5.06 (25)

1.924 (20) 1.85 (70) 2.6 (71) 12.1 (22)

Heptanoic acid 1-Heptanol DL-2-Heptanol DL-3-Heptanol

4-Heptanol 2-Heptanone 3-Heptanone 4-Heptanone 1-Heptene Hexadecamethylcyclooctasiloxane Hexadecane 1-Hexadecanol 1,5-Hexadiene 2,4-Hexadiene Hexafluorobenzene Hexamethyldisiloxane Hexamethylphosphoramide Hexane Hexanedinitrile

0.854 (15) 0.686 (30) 0.736 (20) 0.35 (20) 0.34 (25)

9.21 (22) 6.9 (22) 6.2 (22) 11.95 (20) 8.27 (100) 12.9 (22) 12.60 (20) 9.46 (80) 2.07 (20)

b

1.73 (20) [B]

2.7 (20)

3.591 (22) 3.8 (50) 0.275 (20) 0.244 (36) 2.2 (25)

0.31 (25) [B] 0

22.6 (20)

2.2 (20)

0.37 (25) [lq]

17.01

3.47 (20)

30 (20)

4.31 (25) [lq]

33.8 (20)

0.313 (20) 0.271 (40) 5.99

1.904 (15) 1.890 (20) 32.45

0

20.44

0.102 2

3.8 (25) [B]

47.88

0.097 3

0.076 3

4.78

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

2,4-Hexanedione Hexanenitrile Hexanoic acid 1-Hexanol 2-Hexanone 1-Hexene Hexyl acetate 4-Hydroxy-4methyl-2pentanone Iodobenzene

Viscosity , mN · s · m2

1.041 (15) 0.830 (30) 3.525 (15) 2.511 (3) 6.203 (15) 3.872 (30) 0.584 (25) 0.26 (20) 0.25 (25)

17.26 (25)

1-Iodoheptane 3-Iodoheptane 1-Iodohexadecane 1-Iodohexane Iodomethane 1-Iodo-3methylbutane 2-Iodo-2methylbutane 1-Iodo-2methylpropane 1-Iodooctane 2-Iodooctane 1-Iodopentane 1-Iodopropane 2-Iodopropane p-Iodotoluene -Ionone -Ionone

Dipole moment, D

a

b

32.22 29.64

0.100 2 0.090 7

2.63 (71)

1.13 (25) [lq]

28.05 (20)

27.55 (25)

13.3 (25) 8.5 (75) 14.6 (15) 2.051 (20)

1.55 (20) [B]

27.81

0.080 1

2.68 (22) [B] 0.34 (20) [lq]

28.18 20.47

0.109 2 0.102 7

18.2 (25)

3.24 (20) [B]

28.44 31.0 (20)

0.097 0

2.9 (25)

1.774 (17) 0.488 (149)

4.62 (20)

1.71 [g] 1.3 (20) [B] 2.10 [g] 1.90 (20) [B] 2.06 (20) [B] 1.87 (20) [C] 1.91 [g] 1.69 (20) [lq] 1.86 (22) [B] 1.95 (22) [B]

41.52

0.112 3

30.82

0.013 1

30.32

0.105 6

31.67

0.128 6

32.18

0.088 7

34.49 31.63 33.42

0.088 0 0.084 5 0.123 4

30.37

0.091 5

1-Iodobutane 2-Iodobutane 1-Iodododecane Iodoethane

Dielectric constant, 

6.22 (20) 4.52 (130)

0.617 (15) 0.540 (30)

0.500 (20) 0.424 (40)

0.875 (20) 0.697 (40)

0.837 (15) 0.670 (30) 0.732 (15) 0.620 (30)

3.9 (20) 10.2 (50) 7.82 (20) 4.9 (22) 6.4 (22) 3.5 (20) 5.37 (20) 7.00 (20) 5.6 (19)

1.94 (20) [C] 1.64 [g] 1.42 (20) [B] 1.85 (20) [B]

8.19 (20)

2.20 (20) [B]

6.5 (20)

1.89 (20) [B]

30.26

0.017 2

4.6 (25)

1.80 (25) [lq] 1.90 (20) [C] 2.07 (20) [C] 1.90 (20) [B] 2.03 [g] 1.86 (20) [B] 2.01 (20) [B]

32.51

0.091 5

31.41 31.64

0.101 4 0.113 6

29.35

0.1107

39.23 34.10 35.36

0.096 5 0.094 9 0.095 0

5.8 (20) 5.81 (20) 7.00 (20) 7.87 (20) 4.4 (35) 11 (18) 12 (20)

1.72 (22) [B]

4.79

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Iron pentacarbonyl Isobutyl acetate Isobutylamine Isobutylbenzene Isobutyl butyrate Isobutyl formate Isobutyl isobutyrate Isobutyl nitrate Isobutyl pentanoate Isobutyl propionate Isobutyric acid Isobutyric anhydride Isobutyronitrile Isopentyl acetate Isopentyl butyrate Isopentyl pentanoate Isopentyl propionate Isopropyl acetate Isopropylamine Isopropylbenzene Isopropyl formate 1-Isopropyl-4methylbenzene Isoquinoline Lactamide Lactic acid Lactonitrile D-Limonene DL-Limonene DL-Mandelonitrile Menthol 2-Mercaptoethanol Methacrylic acid Methacrylonitrile Methane [g]

Viscosity , mN · s · m2

0.553 (25)

0.680 (20)

Dielectric constant,  2.6 (20) 5.29 (20) 4.43 (21) 2.319 (20) 2.298 (30) 4.1 (20) 6.41 (19)

Dipole moment, D

a

1.87 (22) [B] 1.27 (25) [B] 0.31 (20) [lq]

25.59 24.48 29.39

0.101 3 0.109 2 0.096 1

1.89 (20) [B]

24.47 26.14 30.92

0.084 3 0.112 2 0.127 0

28.97

0.116 6

b

2.7 (20) 3.8 (19)

1.44 (15) 14 (20)

2.7 (20)

1.09 (25) [lq]

26.88

0.092 0

0.551 (15) 0.456 (30) 0.872 (20) 0.790 (25)

20.4 (24)

3.61 (25) [B]

24.93 (20)

23.84 (30)

4.81 (20) 4.63 (30) 4.0 (20) 3.6 (19)

1.84 (22) [B] 1.76 (30) [lq]

26.75

0.098 9

27.32

0.091 8

24.44 19.91 30.32

0.107 2 0.097 2 0.105 4

24.56 29.44 (20)

0.114 7

38.31 29.50 29.11

0.096 0 0.092 9 0.091 3

45.90

0.098 8

1.8 (28) [B]

4.2 (20) 0.559 (20) 0.36 (25) 0.791 (20) 0.739 (25) 0.512 (20) 3.402 (20) 1.600 (30) 3.253 (30)

40.33 (25) 2.01 (30)

5.45 (20) 2.39 (20)

1.86 (22) [B] 1.45 (25) [B] 0.65 [g] 0.39 (20) [lq]

2.24 (20)

0

10.7 (20)

2.75 [g] 2.55 (25) [B]

22 (17) 38 (20) 2.4 (20) 2.3 (20)

1.57 (25) [B] 0.63 (25) [B]

17.8 (23) 6.89 (35) 3.4 (20) 1.32 (20) 0.392 (20) 0.010 9 (20) 0.013 3 (100)

Methanesulfonic acid * 38.6180.1873T0.000356T2

1.55 (20) [B]

1.000 94 (0)

1.65 3.69 [g] 0

26.5 (25) 24.4 (20) * 52.28

0.089 3

4.80

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Methanethiol Methanol o-Methoxybenzaldehyde p-Methoxybenzaldehyde Methoxybenzene 2-Methoxyethanol 2-(2-Methoxyethoxy)ethanol 2-Methoxyethyl acetate 1-Methoxy-2nitrobenzene o-Methoxyphenol 2-Methoxy-4(2-propenyl) phenol o-Methoxytoluene m-Methoxytoluene p-Methoxytoluene N-Methylacetamide Methyl acetate Methyl acetoacetate Methyl acrylate Methylamine N-Methylaniline Methyl benzoate 2-Methyl-1, 2-butadiene 2-Methylbutane 2-Methyl-1butanol 2-Methyl-2butanol

Viscosity , mN · s · m2

0.676 (10) 0.544 (25)

1.152 (15) 0.789 (30) 1.72 (20) 1.60 (25) 3.48 (25) 1.61 (60)

Dielectric constant, 

Dipole moment, D

28.09 24.00

0.169 6 0.077 3

45.34

0.110 5

3.26 (35) [B]

44.69

0.104 7

1.36 [g] 1.24 (20) [B] 2.04 (25) [B]

38.11

0.120 4

33.30

0.098 4

34.8 (25)

29.9 (75)

48.62

0.118 5

41.2

0.094 3

36.20 33.67 (30)

0.107 1 30.62 (50)

27.95

0.128 9

34.98

0.094 4

1.77 (25) [B] 1.29 [g]

22.87

0.148 8

1.67 (25) [B]

39.32

0.097 0

6.59 (20)

1.86 (25) [B]

40.10

0.117 1

2.1 (25)

0.15 [g]

1.871 (0) 1.845 (20) 14.7 (25)

0.13 [g]

17.20

0.110 3

5.82 (25)

1.72 (20) [B]

22.3 (22) 10.4 (248) 4.33 (25) 3.9 (70) 16.93 (25) 16.0 (30)

2.13 (30) [B] 4.83 [g]

12 (25) 6.931 (25)

1.398 (20) 0.285 (15) 0.236 (0) 2.02 (25) 1.084 (55) 2.298 (15) 1.673 (30) 0.266 (0.3) 0.223 (20) 0.237 (15) 0.215 (25) 5.50 (20) 1.44 (60) 5.48 (15) 2.81 (30)

b

1.26 [g] 1.69 [g] 1.68 (22) [B] 4.34 (20) [B]

41.8 (20) 33.62 (20)

8.25 (20)

3.88 (30) 2.54 (45) 0.388 (20) 0.320 (40) 1.704 (20)

a

2.46 (25) [B]

3.5 (20) 3.5 (20) 4.0 (20) 178.9 (30) 138.6 (60) 7.03 (20) 6.68 (25)

11.4 (10) 10.0 (18)

4.39 (20) [D] 1.70 [g] 1.75 (25) [B]

21.5 (25) 24.18

0.074 8

4.81

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

Viscosity , mN · s · m2

3-Methyl-14.81 (15) butanol 2.96 (30) 3-Methyl-2-butanol 3.51 (25) 2-Methyl-1-butene 2-Methyl-2-butene 3-Methyl-1-butene 2-Methylbutyl 0.872 (20) acetate Methyl butyrate 0.580 (20) 0.459 (40) 3-Methylbutyric 2.731 (15) acid 2.411 (20) 3-Methylbutyronitrile Methyl chloroacetate Methyl 3.82 (50) cyanoacetate 2.69 (65) Methyl0.734 (20) cyclohexane 0.685 (25) cis-2-Methyl18.08 (25) cyclohexanol 13.60 (30) trans-2-Methyl37.13 (25) cyclohexanol 25.14 (30) cis-3-Methyl19.7 (25) cyclohexanol 17.23 (30) trans-3-Methyl25.52 (16) cyclohexanol 15.60 (30) cis-4-Methyl0.247 (25) cyclohexanol trans-4-Methyl0.385 (25) cyclohexanol 2-Methylcyclohexanone 3-Methylcyclohexanone 4-Methylcyclohexanone Methylcyclo0.507 (20) pentane 0.478 (25) Methyl decanoate Methyl dichloroacetate * Mixed isomers.

Dielectric constant,  14.7 (25) 5.82 (130)

Dipole moment, D

a

1.82 (25) [B]

25.76

0.082 0

23.0 (25) 18.81 19.70

0.1148 0.127 1

16.42 26.75

0.103 1 0.098 9

2.20 (20)

0.52 (20) [lq] 0.11 (25) [lq] 0.34 (25) [B] 1.002 8 (100) [g] 0.25 [g] 4.63 (30) 1.82 (22)

b

5.6 (20)

1.72 (22) [B]

27.48

0.114 5

2.64 (20)

0.63 (25)

27.28

0.088 6

18 (220)

3.62 (25) [C]

27.58

0.082 7

12.9 (21)

37.90

0.130 4

19.23 (50) 17.57 (65) 2.02 (20) 2.07 (25) 13.3*

41.32

0.107 4

0

26.11

0.113 0

2.58 (30) [lq]* 1.95 (25) [B]*

32.45

0.077 0*

16.47 (20)

1.91

29.08

0.062 9*

8.05

1.75

28.80 (30)

13.3*

2.70 (30) [lq]* 1.9 (25) [B]*

29.07

0.069 0*

16 (15) 14 (20) 18 (80) 12 (20) 15 (41) 12 (20) 1.985 (20)

2.98 (25) [B]

34.06

0.102 7

3.06 (25) [B]

33.06

0.092 5

3.07 (25) [B]

32.83

0.093 5

0

24.63

0.116 3

1.65 (20) [H]

30.33 37.00

0.091 2 0.121 9

4.82

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Methyl dodecanoate N-Methylformamide Methyl formate Methyl heptanoate 2-Methyl-2heptanol 2-Methyl-3heptanol 2-Methyl-4heptanol 3-Methyl-3heptanol 3-Methyl-4heptanol 4-Methyl-3heptanol 4-Methyl-4heptanol Methyl hexadecanoate 2-Methylhexane 3-Methylhexane Methyl hexanoate Methyl isobutyrate Methyl methacrylate Methyl o-methoxybenzoate Methyl p-methoxybenzoate 1-Methylnaphthalene Methyl o-nitrobenzoate Methyl octadecanoate 2-Methyloctane 4-Methyloctane Methyl octanoate Methyl oleate 2-Methylpentane

Viscosity , mN · s · m2

1.99 (15) 1.65 (25) 0.360 (15) 0.319 (29)

Dielectric constant, 

200.1 (15) 182.4 (25) 8.5 (20)

3.38 (7) 2.46 (25) 3.37 (20) 3.75 (60) 3.30 (20) 3.65 (60) 3.74 (20) 2.89 (60) 9.1 (20) 7.4 (20) 5.25 (20) 4.62 (55) 2.87 (20) 3.27 (60)

Dipole moment, D

a

1.70 (20) [H]

31.37

0.089 3

3.86 (25) [B]

37.96 (30)

35.02 (50)

1.77 [g]

28.29

0.157 2

28.29

0.157 2

31.50

0.077 5 0.096 64 0.097 0 0.104 5 0.113 1

b

1.63 (20) [B]

0.378 (20) 0.372 (20)

1.92 (20) 1.93 (20)

0.523 (20) 0.419 (40) 0.632 (20)

0 0 1.70 (20) [H] 1.98 (20) [B]

21.22 21.73 28.47 25.99

2.9 (20)

1.68 (25) [B]

28–29 (30)

2.7 (20)

0.23 (20) [B]

39.96

0.0934

28 (25)

3.67 (30) [B] 32.20

0.77 5

23.76 24.22 29.93 31.3 (25) 19.37

0.094 0 0.094 0 0.100 2 25.4 (100) 0.099 7

7.7 (21) 4.3 (33)

4.88 (20) 0.310 (20) 0.295 (25)

1.97 (20) 1.97 (20)

0 0

3.211 (20) 1.88 (20)

0

4.83

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance 3-Methylpentane 2-Methyl-2, 4-pentanediol 4-Methylpentanenitrile Methyl pentanoate 2-Methyl-1pentanol 3-Methyl-1pentanol 4-Methyl-1pentanol 2-Methyl-2pentanol 3-Methyl-2pentanol 4-Methyl-2pentanol 2-Methyl-3pentanol 3-Methyl-3pentanol 4-Methyl-2pentanone 4-Methyl-3penten-2-one 1-Methyl-1phenylhydrazine Methyl phenyl sulfide 2-Methylpropane 2-Methylpropanenitrile 2-Methyl-1propanol 2-Methyl-2propanol 2-Methylpropene N-Methylpropionamide Methyl propionate 2-Methylpropionic acid

Viscosity , mN · s · m2

Dielectric constant, 

0.307 (25) 0.292 (30) 34.4 (20)

1.895 (20)

0.980 (20) 9.843 (30) 0.713 (20)

Dipole moment, D

0.007 44 (20) [g] 0.551 (15) 0.456 (30) 4.70 (15) 2.876 (30) 3.316 (20) 2.039 (40) 6.06 (20) 3.56 (40) 0.477 (15) 1.213 (25) 1.126 (30)

b

0

20.26

2.9 (0)

33.1 (20)

15.5 (22)

3.53 (25) [B]

28.89

0.091 7

4.3 (19)

1.62 (22) [B]

27.85 26.98

0.104 4 0.081 9

26.92

0.078 9

25.93

0.074 3

25.07

0.086 1

27.14

0.091 9

24.67

0.082 1

26.43

0.091 4

25.48

0.088 8

23.64 (20)

19.62 (60)

1.38 (20) [B]

42.81

0.123 8

0 4.07 [g] 3.60 (20) [B] 2.96 (30) [lq] 1.78 (20) [B] 1.67 (22) [B]

12.83

0.123 6

24.53

0.079 5

20.02 (15)

19.10 (30)

0.50 [g] 3.59 [g]

14.84 31.20 (20)

0.131 9 29.12 (50)

1.70 (22) [B] 1.08 (25) [lq]

27.58 25.55 (20)

0.125 8 25.13 (25)

4.074 (25)

0.585 (20) 0.522 (30) 0.879 (25)

a

13.11 (20) 11.78 (40) 15.6 (0) 15.1 (20) 7.3 (19)

20.2 26 (34) 17.93 (25) 10.9 (30) 8.49 (50) 185 (20) 151 (40) 6.21 2.73 (40)

0.106 0

3.20 (25) [B] 1.84 (15) [B]

4.84

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance 1-Methylpropyl acetate 2-Methylpropyl acetate 2-Methylpropylamine 2-Methylpropyl formate Methyl propyl ketoxime 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine N-Methyl-2pyrrolidinone Methyl salicylate Methyl tetradecanoate 2-Methyltetrahydrofuran Methyl thiocyanate Morpholine Naphthalene 1-Naphthonitrile 2-Naphthonitrile o-Nitroaniline p-Nitroaniline o-Nitroanisole Nitrobenzene m-Nitrobenzyl alcohol 2-Nitrobiphenyl Nitroethane Nitromethane 1-Nitro-2methoxybenzene o-Nitrophenol 1-Nitropropane

Viscosity , mN · s · m2

Dielectric constant, 

Dipole moment, D

a

b

25.72

0.105 4

0.702 (20) 0.366 (78) 21.7 (25)

5.29 (20)

1.87 (22) [B]

25.59

0.101 3

4.43 (21)

1.27 (27)

24.48

0.109 2

0.680 (20)

6.41 (19)

1.88 (22)

26.14

0.112 2

9.8 (20)

1.96 (25) [B]

36.11

0.124 3

37.35 37.71

0.115 3 0.114 1

32.0 (25)

2.41 (25) [B] 2.60 (25) [B] 4.09 (30) [B] 2.47 (25) [B] 1.62 (25) [B]

42.15 31.00

0.117 4 0.080 0

3.34 (20) [B]

40.66

0.130 5

3.3 (20) 0.805 (20) 0.710 (30)

1.666 (25)

9.41 (30)

0.601 (0) 0.536 (10) 64.3 (0)

6.92 (0) 6.63 (10) 4.3 (19)

2.53 (15) 1.79 (30)

7.33 (25)

1.75 (25) [lq] 1.52 (25) [B]

37.63 (20)

36.24 (30)

0.780 (100) 0.967 (80)

2.54 (85)

0

42.84

0.110 7

4.28 (20) [B] 6.3 (25) [B] 4.83 [g] 4.22 [g] 3.96 (25) [B]

60.62 48.62 46.34

0.092 3 0.118 5 0.115 7

3.82 (20) [B] 3.61 [g]

35.27

0.125 5

3.46 [g]

40.72

0.167 8

4.83 [g]

48.62

0.118 5

3.14 (25) [B] 3.60 [g]

47.35 32.62

0.117 4 0.100 9

16 (70) 17 (70) 34.5 (90) 56.3 (160) 2.165 (15) 1.55 (35)

12 (45) 0.677 (20) 0.63 (35) 0.692 (15) 0.596 (30)

2.343 (45) 0.798 (25) 0.70 (35)

34.82 (25) 24.9 (90) 22 (20)

28.06 (30) 27.4 (35) 35.87 (30) 35.1 (35)

17 (50) 23.24 (30) 22.7 (35)

4.85

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance 2-Nitropropane N-Nitrosodimethylamine o-Nitrotoluene m-Nitrotoluene p-Nitrotoluene Nonane 1-Nonanol 1-Nonene (Z,Z)-9,12Octadecadienoic acid Octamethylcyclotetrasiloxane Octamethyltrisiloxane Octane Octanenitrile Octanoic acid 1-Octanol

Viscosity , mN · s · m2

Oxalyl chloride 2-Oxohexamethyleneimine 4-Oxopentanoic acid Palmitic acid Paraldehyde Parathion

a

b

25.52 (30) 53 (20)

3.76 [g] 4.01 (20) [B]

32.18

0.115 8

2.37 (20) 1.63 (40) 2.33 (20) 1.60 (40) 1.20 (60) 0.713 (20) 0.666 (25) 14.3 (20) 0.620 (20) 0.586 (25)

27.4 (20) 22.0 (58) 24 (20) 22 (58) 22 (52) 1.972 (20) 1.85 (110)

3.72 (20) [B]

44.10

0.117 4

4.20 (20) [B]

43.54

0.111 8

4.47 (25) [B] 0

42.26 24.72

0.097 4 0.093 5

1.72 (20) [B] 0.59 (20) [B]

29.79 24.90

0.078 9 0.093 8

0.081 1

2.70 (70) 2.60 (120)

1.40 (18) [Hx]

2.20 (20)

2.4 (20)

20.19

0.82 (20)

2.3 (20)

0.42 (25) [lq] 0.67 (25) [B] 0.64 (25) [lq]

0.546 (20) 0.433 (40) 1.811 (15) 1.356 (30) 5.828 (20) 4.690 (25) 10.64 (15) 6.125 (30)

1.95 (20) 1.83 (110) 13.90 (25)

0

23.52

0.095 1

29.61

0.080 2

2.45 (20)

1.15 (25) [lq]

29.2 (20)

28.7 (25)

11.3 (10) 10.34 (20) 8.20 (20) 6.52 (40) 10.39 (20) 7.42 (100) 2.084 (20)

1.72 (20) [B]

29.09

0.079 5

1.65 (20) [B]

27.96

0.082 0

0.34 (20) [lq]

23.68

0.095 8

1.44 (25) [lq]

32.80 (20)

27.94 (90)

41.69

0.076 3

28.28 39.2 (25)

0.106 2

2-Octanone

Oleic acid

Dipole moment, D

0.750 (25)

2-Octanol

1-Octene

Dielectric constant, 

0.470 (20) 0.447 (25) 38.80 (20) 27.64 (25)

2.46 (20) 2.45 (60) 3.5 (21)

9 (78)

2.3 (70) 13.9 (25) 15.30 (25)

67.56 (25)

2.72 (15) [B]

0.93 (20) [B] 3.88 (25) [B]

1.91 (25) [lq] 4.98 (25) [B]

4.86

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Pentachloroethane Pentadecane cis-1,3-Pentadiene Pentanaldehyde Pentane 1,5-Pentanediol 2,4-Pentanedione Pentanenitrile

Viscosity , mN · s · m2 2.741 (15) 2.070 (30) 2.814 (22)

0.237 (15) 0.215 (25) 128 (20) 0.6 (20) 0.779 (15) 0.637 (30)

1-Pentanethiol Pentanoic acid 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone 3-Pentanone 1-Pentene cis-2-Pentene trans-2-Pentene Pentyl acetate Pentylamine Pentyl formate Pentyl nitrate Phenanthrene Phenol Phenoxyacetaldehyde Phenoxyacetylene 2-Phenylacetamide Phenyl acetate Phenylacetonitrile

2.359 (15) 1.774 (30) 4.650 (15) 2.987 (20) 5.130 (15) 2.780 (30) 7.337 (15) 3.306 (30) 0.473 (25) 0.493 (15) 0.423 (30) 0.24 (0)

0.924 (20) 0.862 (25) 1.018 (20)

6.024 (35) 3.421 (50)

Dielectric constant,  3.73 (20)

2.32 (25) 10.1 (17) 2.011 (90) 1.84 (20) 25.7 (20) 17.39 (25) 17.4 (21) 4.55 (25) 4.23 (50) 2.66 (20)

Dipole moment, D

a

b

0.92 [g] 0.98 (25) [lq] 0 0.50 (25) [B] 2.59 (20) [B] 0

37.09

0.117 8

28.78

0.085 7

27.96 18.25

0.101 0 0.112 1

2.45 (20) [D] 3.03 [g] 2.5 (20) [B] 3.57 (25) [B]

43.2 (20) 33.28

0.1144

27.44 (20)

26.33 (30)

1.61 (20) [D]

28.90

0.088 7

1.54 (25) [lq]

16.9 (20) 13.9 (25) 13.82 (22)

1.71 (20) [B]

27.54

0.087 4

1.66 (22) [B]

25.96

0.100 4

13.02 (22)

1.64 (22) [B]

24.60 (20)

23.76 (30)

15.45 (20) 11.73 (80) 19.4 (20) 17.00 (20) 2.10 (20)

2.72 (22) [B]

24.89

0.065 5

2.72 (20) [B]

27.36

0.104 7

0.34 (20) [lq]

4.75 (20)

1.72 [g] 1.91 (25) [B] 1.55 (30) [B]

18.20 19.73 18.90 27.66

0.109 9 0.117 2 0.099 7 0.099 4

24.4 (13) 28.09

0.102 3

43.54

0.106 8

46.26

0.078 8

44.57

0.115 5

4.5 (22) 6.5 (20) 9 (18) 2.8 (20) 9.78 (60)

0 1.53 (20) [B]

4.8 (20) 4.8 (20)

1.799 (45) 1.93 (25)

5.23 (20) 19.0 (25) 8.5 (234)

1.42 (25) [lq]

1.54 (22) [B] 3.47 (27) [B]

4.87

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

Viscosity , mN · s · m2

Phenylacetylene 1-Phenylethanol

Piperidine Propane [g] 1,2-Propanediamine 1,3-Propanediamine 1,2-Propanediol 1,3-Propanediol 1-Propanethiol 2-Propanethiol 1-Propanol 2-Propanol

Dipole moment, D

a

0.72 (20) [B] 1.51 (20) [B]

42.88

0.103 8

1.67 (25) [B]

48.14

0.129 2

42.73

0.108 6

34.27

0.105 6

45.20

0.097 6

0.60 (25) [B]

28.35 28.26

0.094 4 0.093 4

5.8 (20)

1.19 (25) [B]

31.79

0.115 3

1.6 (0)

0

9.22

0.087 4 [lq]

3.0 (20) 13 (20) 7.6 (90) 7.2 (21) 8.8 (20) 10 (20)

Phenylhydrazine Phenyl isocyanate Phenyl isothiocyanate 1-Phenylpropene 2-Phenylpropene 3-Phenylpropene Phenyl propyl ether Phenyl salicylate Phosgene Phthalide DL--Pinene L--Pinene

Dielectric constant, 

2.7 (20) 2.3 (20) 2.6 (20)

1.61 (25) 1.70 (20) 1.41 (25) 1.679 (15) 1.224 (30) 0.008 1 (20) 0.010 7 (125) 1.46

6.3 (50) 4.7 (0) 4.3 (22) 36 (75) 2.64 (25) 2.76 (20)

10.2

17.85

9.55

1.96 (25) [B]

56.0 (20) 18.0 (40) 56.0 (20) 18.0 (40)

32.0 (20)

2.27 (25) [D]

72.0 (25)

35.0 (20)

2.52 (25) [D]

47.43

0.090 3

1.55 (25) [lq] 1.64 (25) [lq] 1.67 [g] 1.75 (25) [B] 1.69 [g] 1.66 (30) [B] 3.04 [g] 2.90 (25) [B] 0.35 [g]

27.38 24.26 25.26

0.127 2 0.117 4 0.077 7

22.90

0.078 9

9.99

0.142 7 [lq]

1.63 [g]

27.53

0.090 2

2.522 (15) 1.722 (30) 2.859 (15) 1.765 (30)

22.2 (20) 20.33 (25) 18.3 (25) 16.24 (40)

0.008 43 (20) 0.009 33 (50) 1.363 (20) 0.914 (40) 0.357 (15) 0.317 (27)

1.88 (20) 1.44 (90) 21.6 (15)

2-Propenaldehyde Propene [g] 2-Propen-1-ol Propionaldehyde

b

18.5 (17)

2.75 [g] 2.57 (20) [B]

4.88

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Propionamide Propionic acid Propionic anhydride Propionitrile Propyl acetate Propylamine

Viscosity , mN · s · m2

1.175 (15) 0.956 (30) 1.144 (20) 1.061 (25) 0.454 (15) 0.389 (30) 0.585 (20) 0.460 (40) 0.343 (25)

Propylbenzene Propyl benzoate Propyl butyrate Propyl chloroacetate Propylene carbonate Propylene oxide Propyleneimine Propyl formate Propyl isobutyrate Propyl nitrate Propyl pentoate Propyl propionate Propyne 2-Propyn-1-ol Pulegone Pyradazine Pyrazine Pyridine Pyrimidine Pyrrole Pyrrolidine 2-Pyrrolidone

Dielectric constant, 

3.30 (10) 3.44 (40) 18.3 (16)

64.4

0.327 (20) 0.28 (25) 0.491 (25)

1.68 (20)

30.30 (20)

29.70 (25)

29.63

0.115 3

26.60

0.112 0

24.86

0.124 3

31.13

0.107 5

36.55 27.06 32.91

0.106 9 0.100 0 0.108 3

26.77

0.111 9

25.83 29.67 27.72 26.85 14.51 38.59

0.101 5 0.123 7 0.098 4 0.105 9 0.148 2 0.127 0

50.55

0.103 6

39.82

0.130 6

32.85 39.81

0.101 0 0.110 0

1.58 (20) [B] 3.55 (25) [B]

31.48

0.090 0

2.18 (25) [B]

45.25

0.106 3

3.1 (30) [lq] 2.86 (20) [B]

45.38

0.124 2

1.17 [g] 1.36 (20) [B] 0.35 (25) [lq]

2.53

b 0.090 9 0.099 3

5.31 (20)

4.3 (20)

a 39.05 28.68

4.06 [g] 3.60 (20) [B] 1.86 (25) [B]

0.831 (20)

1.053 (20) 0.673 (20)

3.4 (30) [B] 1.76 [g] 1.77 (25) [D]

22.2 (20) 24.2 (50) 5.69 (19)

2.37 (20) 2.351 (30)

0.574 (20) 0.417 (40) 0.831 (20)

Dipole moment, D

2.00 [g]

7.72 (19)

14 (18) 4 (19) 4.7 (20) 24.5 (20) 9.5 (20)

1.130 (10) 0.829 (30)

2.8 (54) 12.3 (25) 9.4 (116)

1.352 (20) 1.233 (25)

7.48 (18) 8.13 (25)

13.3 (25)

Quinoline

4.354 (15) 3.37 (25)

9.00 (25)

Safrole Salicylaldehyde

2.294 (25) 2.90 (20) 1.67 (45)

3.1 (21) 13.9 (20)

1.77 [g, cis] 1.60 [g, trans] 1.91 (22) [B]

3.01 (20) [B] 1.79 (22) [B] 0.75 [g] 1.78 (25) [B] 2.00 (25) [B] 3.97 (35) [D] 0 2.20 (20) [B] 2.25 [g] 2.44 (35) [D] 1.80 (25) [B]

4.89

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance

Viscosity , mN · s · m2

Squalane Squalene D-Sorbitol Stearic acid

6.08 (20) 12 (25)

Styrene

0.751 (20) 0.696 (25) 2.591 (60) 2.008 (75) 13.950 (11) 9.797 (20)

Succinonitrile 1, 1,2,2Tetrabromoethane 1, 1,2,2Tetrachlorodifluoroethane 1, 1,2,2-Tetrachloroethane Tetrachloroethylene Tetradecamethylcycloheptasiloxane Tetradecamethylhexasiloxane Tetradecane Tetradecanoic acid 1-Tetradecanol Tetraethylene glycol Tetraethyllead Tetraethylsilane Tetraethyl silicate Tetrahydrofuran 2,5-Tetrahydrofurandimethanol Tetrahydro-2furanmethanol 1,2,3,4-Tetrahydronaphthalene 1,2,3,4Tetrahydro2-naphthol

11.6 (70)

Dielectric constant, 

Dipole moment, D

a

b

0.13 (25) [lq]

32.0 (20)

30.98 (30)

3.68 (30) [toluene] 1.29 (20) [H]

53.26

0.107 9

52.37

0.146 3

26.13

0.113 3

1.29 [g] 1.45 (25) [H] 0

38.75

0.126 8

32.86 (15)

31.27 (30)

2.5 (20)

1.58 (20) [lq]

17.42 (25)

0 33.90

28.30 0.093 2

0.086 9

0.76 (25) [B]

1.69 (25) [C]

32.72

0.070 3

5.84 (20) [lq]

45 (25)

0.3 (20) [B] 0 1.72 (32) [B] 1.75 (25) [B]

30.50 25.22 23.63 26.5 (25)

0.096 9 0.107 9 0.097 9

0 0.68 (25) [B] 33 (80) 2.29 (70) 2.26 (100) 2.43 (25) 2.32 (75) 56.5 (57) 54 (68) 8.6 (3) 7.0 (22)

1.21 (25) 1.208 (30)

2.52 (25)

1.844 (15) 1.456 (30) 1.932 (15) 0.798 (30)

8.20 (20) 2.30 (25)

1.76 (25) [D]

2.7 (20)

2.131 (22)

4.72 (38) 4.40 (48) 44.9 (25)

0.55 (20) 0.460 (25) 225 (25)

4.1 (20) 11.6 (70) 7.58 (25)

6.24 (20)

13.61 (23)

2.12 (35) [lq]

39.96

0.100 8

2.202 (20) 2.003 (25)

2.76 (20)

0.60 (25) [lq]

35.55

0.095 4

11.7 (20) 6.7 (90)

4.90

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Tetrahydropyran Tetrahydropyran2-methanol Tetrahydrothiophene-1, 1-dioxide Tetrahydrothiophene oxide 1,1,2,2-Tetramethylurea Tetranitromethane Tetrathiomethylmethane Thiacyclohexane Thiacyclopentane

Viscosity , mN · s · m2

Dielectric constant, 

0.826 (20) 0.764 (25) 11.0 (20)

5.61 (25)

9.87 (30)

43.3 (30)

52 (30) 19 (80)

42.5 (30)

1.76 (20)

a

b

1.55 (25) [B] 34.1 (25) 4.81 (25) [B]

23.06

3.47 (25) [B]

2.32 (20) 2.82 (70)

0

1.042 (20) 0.971 (25)

Thioacetic acid 2,2 -Thiodiethanol 65.2 (20) Thiophene 0.662 (20) 0.353 (82) Thymol Toluene 0.623 (15) 0.523 (30) p-Toluenesulfonyl chloride o-Toluidine 5.195 (15) 4.39 (20) m-Toluidine 4.418 (15) 2.741 (30) p-Toluidine 1.945 (45) 1.557 (60) m-Tolunitrile p-Tolunitrile Tribenzylamine Tributyl 1.9 (25) phosphite 2,2,2-Tribromoacetaldehyde Tribromoethane 2.152 (15) 1.741 (30) 1,2,3-Tribromopropane Tributylamine 1.35 (25) Tributyl borate 1.776 (20) 1.601 (25)

Dipole moment, D

35.5 (30)

36.06 (20) 38.44

33.74 (40) 0.134 2

53.8 (20) 34.00

0.132 8

33.95 30.90

0.082 1 0.118 9

42.41

0.090 3

1.60 (25) [B]

42.87

0.109 4

1.45 (25) [B]

40.33

0.097 9

1.52 (25) [B]

39.58

0.095 7

4.21 (22) [B] 4.47 (20) [B] 0.65 (20) [B] 1.92 (20) [C]

38.85 39.79 42.41 27.57

0.101 3 0.110 0 0.095 3 0.086 5

1.90 (25) [B] 12.8 (20) 2.76 (16) 2.57 (25) 2.385 (20) 2.364 (30)

6.34 (18) 5.71 (58) 5.95 (18) 5.45 (58) 4.98 (54)

0.55 [g] 0.52 (25) [B] 1.55 (25) [B] 0.45 (20) [lq]

7.6 (20)

1.70 (20) [B]

4.39 (20)

0.99 [g]

48.14

0.130 8

6.45 (20)

1.59 (25) [B]

47.99

0.126 7

0.78 (25) [B] 0.78 (25) [C]

26.47 26.2 (20)

0.083 1 25.8 (25)

4.91

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Tributyl phosphate Trichloroacetaldehyde Trichloroacetic acid Trichloroacetonitrile 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichloromethylsilane 2,4,6-Trichlorophenol 1,2,3-Trichloropropane Trichlorosilane ,,-Trichlorotoluene 1,1,2-Trichloro1,2,2,-trifluoroethane Tridecane 1-Tridecene Triethanolamine Triethylaluminum Triethylamine Triethylene glycol Triethyl phosphate Triethyl phosphite

Viscosity , mN · s · m2 l 11.1 (15)

0.903 (15) 0.725 (30) 0.119 (20) 0.110 (25) 0.566 (20) 0.532 (25) 0.42 (25) 0.011 (25) [g] 0.47 (20)

0.332 (20) 0.316 (25) 3.07 (10) 2.55 (17) 0.711 (20) 0.627 (30)

Dielectric constant,  3.39 (25)

7.96 (30) [B]

7.6 (40) 4.9 (20) 4.6 (60)

1.96 (25) [B]

0.394 (15) 0.363 (30) 49.0 (20) 8.5 (60) 1.684 (40) 1.376 (55) 0.72 (25)

a

b

3.07 (25) 28.71 27.66

0.066 6

35.4

0.089 5

7.85 (19)

1.1 (25) [B, dimer] 1.93 (19) [lq]

7.1 (7) 7.52 (20) 8.78 (23)

1.79 [g] 1.6 (25) [B] 1.45 [g]

28.28

0.124 2

37.40

0.135 1

3.42 (16)

0.77 (30) [lq] 0.95 (30) [B] 0.45 [g] 0.49 [lq] 1.87 (25) [B]

29.5 (20)

28.8 (25)

18 (25)

1.88 (25) [D]

43.13

0.095 5

7.5 (20)

1.61 [g]

37.8 (20)

37.05 (25)

20.43

0.107 6

6.9 (21)

0.86 [g] 0.98 (25) [B] 2.17 (20) [B]

17.75 (20)

16.56 (30)

27.73

0.087 2

28.01

0.088 4

2.28 (29)

2.41 (25)

1.883 (20) 1.55 (23) 613.6 (25) 208.1 (40)

Dipole moment, D

0

29.36 (25) 2.9 (20) 2.42 (25) 23.7 (20) 13.43 (15) 10.93 (65) 5.0

9.119 7

20.3 (20)

3.57 (25) [B]

0.66 [g] 0.9 (25) [B] 5.58 (20) [lq]

22.70

0.099 2

47.33

0.088 0

3.08 (25) [B]

31.81

0.092 8

1.82 (25) [D]

25.73

0.087 8

4.92

SECTION 4

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Trifluoroacetic acid 2,2,2-Trifluoroethanol ,,-Trifluorotoluene Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Trimethyl borate 2,2,3-Trimethylbutane cis, cis-1,3,5Trimethylcyclohexane trans-1,3,5Trimethylcyclohexane Trimethylene sulfide 3,5,5-Trimethyl1-hexanol 2,6,8-Trimethyl4-nonanone 1,3,5-Trimethyl2-oxabicyclo[2.2.2]octane 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane Trimethyl phosphite 2,4,6-Trimethylpyridine Triphenylamine Triphenyl phosphite Tripropylamine

Viscosity , mN · s · m2 0.926 (20) 0.653 (40) 1.996 (20)

Dielectric constant,  8.55 (20) 5.76 (50)

Dipole moment, D

a

b

2.28 [g]

15.64

2.03 (25) [cH]

20.6 (33)

0.56 (20) [lq]

16.24 30.91

0.113 3 0.104 0

0.30 (20) [lq]

31.76

0.102 5

0

29.79

0.089 7

0.82 (25) [C] 0

20.70

0.097 3

1.78 (25) [B]

36.3 (20)

35.0 (30)

4.57 (24)

1.54 (25) [C]

32.1 (20)

31.1 (25)

0.598 (20)

1.962 (20)

0

22.46

0.089 5

0.502 (20)

1.940 (20)

0

20.55

0.088 8

1.83 (20) [C]

27.18 (20)

24.88 (40)

46.2

0.095 5

24.58

0.087 8

0.894 (15) 0.730 (30) 1.154 (20)

9.2 (30) 8.1 (60) 2.4 (25) 2.636 (20) 2.609 (30) 2.38 (20) 2.36 (30) 2.28

0.579 (20)

8 (20) 1.93 (20)

0.321 (33)

0.184 4

0.632 (20) 0.558 (30) 0.714 (20) 0.624 (30) 0.638 (20) 0.607 (25) 11.06 (25) 1.9 (20)

0.61 (20) 1.498 (20) 1.496 (25)

6.6

1.95 (25) [B]

25.18 (15) 6.95 (45)

3.67 (45) 3.57 (65)

2.04 (25) [B] 0.58 (20) [lq] 0.76 (20) [B]

4.93

PHYSICAL PROPERTIES

TABLE 4.10 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Organic Substances (continued ) Surface tension, dyn · cm1 Substance Tripropylene glycol Tripropylene glycol butyl ether Tripropylene glycol ethyl ether Tripropylene glycol isopropyl ether Tripropylene glycol methyl ether Tris(dimethylamino) phosphine oxide Tris(4-ethylphenyl) phosphite Tris(m-tolyl) phosphite Tris(p-tolyl) phosphite Tritolyl phosphate Undecane 2-Undecanone Urea

Viscosity , mN · s · m2

6.58 (25)

28.8 (25)

5.17 (25)

28.2 (25)

7.7 (25)

27.4 (25)

5.96 (25)

30.0 (25)

3.34 (30)

30 (20)

30.22 (15) 9.047 (45)

3.74 (15) 3.61 (45)

2.08 (25) [B]

37.55 (15) 9.132 (45) 35.52 (15) 8.794 (45) 38.8 (35) 16.8 (55)

3.67 (15) 3.53 (45) 3.88 (15) 3.74 (45) 6.92 (40)

1.62 (25) [B]

1.186 (20) 0.761 (50) 1.61 (30)

2.00 (20) 1.84 (150)

0.421 (20) 0.809 (20) 0.627 (40) 0.617 (20) 0.497 (40) 0.644 (20) 0.513 (40)

Xylitol

a 34 (25)

o-Xylene

p-Xylene

Dipole moment, D

56.1 (25)

Vinyl acetate

m-Xylene

Dielectric constant, 

b

1.77 (25) [B] 2.84 (40) [C]

40.9 (20)

0

26.26

0.090 1

2.71 (15) [B] 4.59 (25) [D] 2.57 (20) 2.54 (30) 2.37 (20) 2.35 (30) 2.26 (20) 2.22 (50) 40 (20)

1.79 (25) [B]

23.95 (20)

22.54 (30)

0.62 [g] 0.52 (25) [lq] 0.33 (20) [lq] 0.37 (20) [B] 0

32.51

0.110 1

31.23

0.110 4

30.69

0.107 4

4.94

SECTION 4

TABLE 4.11 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substance Temperature in degree celsius are indicated in parentheses. The physical state of the substance is indicated in square brackets

Substance Air (20 C) AlBr3 Ar [g] (20 C) [lq] AsBr3 AsCl3 AsH3 (arsine) BBr3 BCl3 BF3 B2H6 (diborane) B5H9 B3H6N3 (triborotriazine) Br2 [g] (20 C) [lq] BrF3 BrF5 Cl2 [g] (20 C) [lq] ClF3 ClO3F (perchloryl fluoride) Co [g] [lq] CO2 [g] (20 C) [lq] COCl2 COF2 COS COSe CS CS2 [g] [lq] CrO2Cl2 [chromyl(VI) chloride] D2 (deuterium) DH D2O

Viscosity, mN · s · m2

Dielectric constant, 

Dipole moment, D

0.018 2

1.000 536 4 3.38100

5.2

0.022 3

1.000 517 2 1.538191 8.8335 12.620 2.0520 2.580 1.87292.5

1.0316 2.2220 0.6224

1.012 8 3.0920 7.9124.5

0.013 2 0.4812

0.017 520

1.000 700

1.000 922 1.600 C, 50 atm 4.3422

3.4710

0.37520

a

b

0 1.61 1.59 0.20 0 0 0 0 2.13 0

34.28 54.51 41.67

0.249 3 0.1043 0.097 81

31.90

0.128 0

2.92 3.13

0.230 0 0.178 5

0 1.1 1.51

45.5 38.30 25.24

0.182 0 0.099 9 0.109 8

26.9 12.24

0.166 0 0.157 6

30.20

0.207 3

22.59

0.145 6

12.12

0.177 9

6.537 (71.7220)*

0.188 3 (68.3840)*

0 1.9114 4.2925

0.014 7 0.07120

Surface tension, dyn · cm1

1.002 90 2.620 2.620

0.554 0.023

0.112

0 1.17 0.95 0.712 0.73 1.98 0 0.47

1.277253 1.09825

*Actual values of surface tension.

78.2525

1.87

4.95

PHYSICAL PROPERTIES

TABLE 4.11 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances (continued )

Substance F2 GaCl3 GeCl4 H2 [g] (20 C) [lq] HBr [g] [lq] HCl [g] [lq] HCN HCNO (isocyanate) HCNS (isothiocyanate) HF HI [g] [lq] NH3 (azide) H2O (see Table 4.12) H2O2 HNO3 H2S [g] [lq] H2Se H2SO4 HSO3Cl (chlorosulfonic acid) HSO2F (fluorosulfonic acid H2Te He [g] (20 C) Hg I2 IF5 Kr [g] (20 C) [lq] Ne[g] (20 C) N2 [g] (20 C) [lq]

Viscosity, mN · s · m2

Dielectric constant, 

Dipole moment, D

1.54202 2.43025 0.008 8

0.85 0

1.000 253 8 1.22820.4 K

0

1.003 130 3.8225

0.82

0.8367

1.004 60 4.6028 11620

1.08

0.5195 0.20618

0.2560

83.60 1.002 340 2.9022

Surface tension, dyn · cm1 a

16.10 0.164 6 35.0 0.100 0 (22.4430)*

13.10

2.98 1.6 1.7 1.82

b

0.207 9

(19.4510)* (18.3320)*

10.41

0.078 67

78.97

0.154 9

0.24

48.95 22.32

0.175 8 0.148 2

0.2

29.03

0.261 9

490.6

0.204 9

33.16

0.131 8

40.576

0.289 0

26.42

0.226 5

0.44 0.8

1.2520

84.20

2.2 2.17

1.00 4 00 5.9310

0.97

0.4120 24.5425 2.4320

10025 6020

1.5625

12025

0.019 6 1.55220 1.98116

1.000 065 0 11.1118

0 0 0 2.18 0.05

0.025 0 0.031 3

1.000 063 9

0

0.017 6

1.000 548 0 1.454203

0

*Actual values of surface tension.

4.96

SECTION 4

TABLE 4.11 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances (continued )

Substance NH3 [g] [lq] N2H4 (hydrazine) NO N2O [g] [lq] NO2 N2O4 NOBr (nitrosyl bromide) NOCl NOF NO2F (nitryl fluoride) O2 [g] (20 C) [lq] O3 OF2 (oxygen difluoride) OsO4 PBr3 PCl3 PCl5 PF5 PH3 PI3 POCl3 POF3 PSCl3 PbCl4 S2Cl2 dimer S2F2 FSSF isomer S¨SF2 isomer SF4 SF6 S2F10 SO2 [g] [lq] SO3 SOBr2 (thionyl bromide) SOCl2

Viscosity, mN · s · m2

Dielectric constant, 

0.25433.5 0.9720

1.007 20 22.433.4 52.920

0.014 620

1.001 130 1.5215 2.5615

0.020 4

0.012 629

*Actual values of surface tension.

1.009 30 15.00 3.1118 9.0620 9.2520

67.48

0.585 3

5.09

0.203 2

29.49 14.00 8.26

0.149 3 0.116 5 0.185 4

33.72 (38.1183)*

0.256 1

45.34 31.14

0.128 3 0.126 6

61.66 35.22

0.067 71 0.127 5

37.00

0.127 2

46.23

0.146 4

12.87 5.66

0.173 4 0.119 0

26.58

0.194 8

36.10

0.141 6

0.316 0.5

0

2.02020

b

0.167

1.000 494 7 1.507193

5.822 2.7820 4.7915

a

(37.9150)* (35.3840)* 1.75 0.153

1.8 1.9 1.81 0.47

2.915 4.1265 13.725

Surface tension, dyn · cm1

1.47

13.415 18.212

3.920 3.4325 2.7165

1.06525

Dipole moment, D

0.53 0.297 0 0.5 0.78 0.9 0 0.58 0 2.41 1.76 1.42 1.0 1.45 1.03 0.632 0 0 1.63 0 9.11 1.45

4.97

PHYSICAL PROPERTIES

TABLE 4.11 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances (continued )

Substance SO2Cl2 (sulfuryl chloride) SbCl3 SbCl5 SbF5 SbH3 SeF4 SeF6 SeOCl2 SiCl4 SiF4 SiH4 SiHCl3 SnBr4 SnCl4 TeF6 TiCl4 UF6 [g] [lq] VCl4 VOBr3 VOCl3 Xe [g] (20 C)

Viscosity, mN · s · m2

Dielectric constant, 

Dipole moment, D

Surface tension, dyn · cm1 a

b

9.1520

1.81

32.10

0.132 8

33.275 3.2220

3.93 0

47.87

0.123 8

49.07

0.193 7

38.61

0.127 4

20.78

0.099 62

20.43

0.107 6

29.92

0.113 4

0.12

5525 2.4016

2.8920 2.8020

0.022 8

*Actual values of surface tension.

1.002 9267 2.1865 3.0525 3.625 3.425 1.001 23

0 2.64 0 0 0 0.86 0 0 0 0

(33.5420)* (31.0640)*

0 25.5

0.124 0

0 0.3 0

(36.3620)* (33.6040)*

4.98

SECTION 4

TABLE 4.12 Refractive Index, Viscosity, Dielectric Constant, and Surface Tension of Water at Various Temperatures

Temperature, C

Refractive index, nD

Viscosity, mn · s · m2

0 5 10 15 20 21 22 23 24 25 26 27 28 29 30 35 40 45 50 55 60 65 70 75 80 85 90 95 100

1.333 95 1.333 88 1.333 69 1.333 39 1.333 00 1.332 90 1.332 80 1.332 71 1.332 61 1.332 50 1.332 40 1.332 29 1.332 17 1.332 06 1.331 94 1.331 31 1.330 61 1.329 85 1.329 04 1.328 17 1.327 25 1.326 16 1.325 11 1.323 99

1.770 2 1.510 8 1.303 9 1.137 4 1.001 9 0.976 4 0.953 2 0.931 0 0.910 0 0.890 3 0.870 3 0.851 2 0.832 8 0.814 5 0.797 3 0.719 0 0.652 6 0.597 2 0.546 8 0.504 2 0.466 9 0.434 1 0.405 0 0.379 2 0.356 0 0.335 2 0.316 5 0.299 5 0.284 0

Dielectric constant, 

Surface tension, dyn · cm1

87.74 85.76 83.83 81.95 80.10 79.73 79.38 79.02 78.65 78.30 77.94 77.60 77.24 76.90 76.55 74.83 73.15 71.51 69.91 68.35 66.82 65.32 63.86 62.43 61.03 59.66 58.32 57.01 55.72

75.83 75.09 74.36 73.62 72.88 72.73 72.58 72.43 72.29 72.14 71.99 71.84 71.69 71.55 71.40 70.66 69.92 69.18 68.45 67.71 66.97 66.23 65.49 64.75 64.01 63.28 62.54 61.80 61.80

4.99

PHYSICAL PROPERTIES

COMBUSTIBLE MIXTURES TABLE 4.13 Properties of Combustible Mixtures in Air Additional compounds can be found in National Fire Protection Association, Fire Protection Handbood, 14th ed., 1976. Flammable limits, percent by volume of fuel (25 C, 760 mm) Autoignition temperature, C

Lower

Acetaldehyde Acetic acid, glacial Acetic anhydride Acetone Acetonitrile Acetylene Acrolein Acrylonitrile Allyl alcohol Allylamine Ammonia, anhydrous Aniline

175 465 390 465 524 305 235* 481 378 374 651 615

4.0 5.4 2.9 2.6 4.4 2.5 2.8 3.0 2.5 2.2 16 1.3

6.0 16.0 10.3 12.8 16.0 100 31.0 17 18.0 22 25

Benzene Biscyclohexyl 1-Bromobutane 3-Bromopropene Butane Butanol 2-Butanone 1-Butene 3-Buten-1-ol Butyl acetate Butylamine Butylbenzene Butylene oxide Butyl formate Butyraldehyde Butyric acid

560 245 265 295 405 365 516 385

1.3 0.7 (100 C) 2.6 (100 C) 4.4 1.9 1.4 1.8 1.6 4.7 1.7 1.7 0.8 1.5 1.7 2.5 2.0

7.1 5.1 (150 C) 6.6 (100 C) 7.3 8.5 11.2 10 10.0 34 7.6 9.8 5.8 18.3 8.2 12.5 10.0

Carbon disulfide Carbon monoxide Carbonyl sulfide Chlorobenzene 2-Chloro-1,3-butadiene 1-Chlorobutane 2-Chloro-2-butene 1-Chloro-1,1-difluoroethane 2-Chloroethanol Chloromethane

90 609

1.3 12.5 12 1.3 4.0 1.8 2.3 6.2 4.9 10.7

50.0 74 29 7.1 20.0 10.1 9.3 17.9 15.9 17.4

Substance

*Unstable.

425 312 410 322 230 450

640

425 632

Upper

4.100

SECTION 4

TABLE 4.13 Properties of Combustible Mixtures in Air (continued ) Flammable limits, percent by volume of fuel (25 C, 760 mm) Substance

Autoignition temperature, C

1-Chloropentane 2-Chloropropane 1-Chloro-1-propene 3-Chloro-1-propene Chlorotrifluoroethylene Crotonaldehyde Cumene Cyanogen Cyclohexane Cyclopropane

260 593

Decahydronaphthalene Decane Diborane Dibutyl ether o-Dichlorobenzene 1,2-Dichloroethylene Dichloropropane Diisopropyl ether Diethylamine Diethyl ether 2,2-Dimethylbutane Dimethyl ether N,N-Dimethylformamide 1,1-Dimethylhydrazine 2,3-Dimethylpentane 2,2-Dimethylpropane Dimethyl sulfide Dimethyl sulfoxide 1,4-Dioxane Divinyl ether

250 210 38–52† 194 648

Ethane Ethanol 2-Ethoxyethanol 1-Ethoxypropane Ethyl acetate Ethylamine Ethylbenzene Ethylcyclobutane Ethylene Ethyleneimine Ethylene oxide Ethyl formate 1,3-Ethylidene dichloride Ethyl nitrite †

Ignites in moist air.

485 232 425 245 500

557 443 312 160 425 445 249 335 450 206 215 180 360 515 365 235 427 385 432 210 490 320 429 455 440 90

Lower

Upper

1.6 2.8 4.5 2.9 8.4 2.1 0.9 6.6 1.3 2.4

8.6 10.7 16 11.1 38.7 15.5 6.5 42.6 8 10.4

0.7 0.8 0.8 1.5 2.2 9.7 3.4 1.4 1.8 1.9 1.2 3.4 1.2 2 1.1 1.4 2.2 2.6 2.0 1.7

4.9 5.4 88 7.6 9.2 12.8 14.5 7.9 10.1 36.0 7.0 27.0 7.0 95 6.7 7.5 19.7 28.5 22.0 27

3.0 3.3 1.8 1.7 2.2 3.5 1.0 1.2 2.7 3.6 3.6 2.8 6.2 3.0

12.5 19 14.0 9.0 11.0 14.0 6.7 7.7 36.0 46 100 16.0 16 50

4.101

PHYSICAL PROPERTIES

TABLE 4.13 Properties of Combustible Mixtures in Air (continued ) Flammable limits, percent by volume of fuel (25 C, 760 mm) Autoignition temperature, C

Lower

Upper

Ethyl propionate Ethyl vinyl ether

440 202

1.9 1.7

11 28

Formaldehyde 2-Furaldehyde Furan Furfuryl alcohol

429 316 491

7.0 2.1 2.3 1.8

73 19.3 14.3 16.3

Gasoline, 92 octane

~280

1.4

7.6

Heptane Hexane 2-Hexanone Hydrocyanic acid, 96% Hydrogen 4-Hydroxy-4-methyl-2pentanone

215 225 533 538 400 603

1.0 1.1 1.2 5.6 4.0 1.8

6.7 7.5 8 40.0 75 6.9

Isobutyl acetate Isobutylbenzene Isopentane Isopentyl acetate Isoprene Isopropyl acetate Isopropyl alcohol

421 430 420 360 220 460 399

2.4 0.8 1.4 1.0 2 1.8 2.0

10.5 6.0 7.6 7.5 9 8 12

Methane Methanethiol Methanol 2-Methoxyethyl acetate Methyl acetate Methyl acrylate Methylamine 2-Methyl-2-butanol 3-Methyl-1-butene Methylcyclohexane Methyl formate 2-Methylpropene 4-Methyl-2-pentanone 2-Methylpropene -Methylstyrene Methyl propionate

540

430 437 365 250 465 465 460 465 574 469

5.4 3.9 6.7 1.7 3.1 2.8 4.9 1.2 1.5 1.2 5.0 1.8 1.4 1.8 1.9 2.5

15.0 21.8 36.0 8.2 16 25 20.6 9.0 9.1 6.7 23 9.6 7.5 9.6 6.1 13

Nicotine Nitrobenzene Nonane

244 482 205

0.7 1.8 (93 C) 0.8

4.0

Octane

220

1.0

6.5

Substance

385 502

2.9

4.102

SECTION 4

TABLE 4.13 Properties of Combustible Mixtures in Air (continued ) Flammable limits, percent by volume of fuel (25 C, 760 mm) Substance

Autoignition temperature, C

Lower

Upper

175 482

2.2 1.5 1.5 1.1 1.1 2.2 2.6 2.1 2.0 2.0 2.9 2.0 2.8 2 1.8

22 7.8 8.2 7.5 5.9 9.5 12.5 13.5 11.1 10.4 17.0 8 37.0 100 12.4

Styrene

490

1.1

6.1

Tetrahydrofuran Tetrahydrofurfuryl alcohol Tetrahydronaphthalene Toluene Trichlorothylene Triethylamine Triethylene glycol Trimethylamine Trioxane

321 282 385 480 420

2 1.5 0.8 1.2 12.5 1.2 0.9 2.0 3.6

11.8 9.7 5.0 7.1 90 8.0 9.2 11.6 29

2.6 1.4 3.6 2.6

13.4 8.8 33.0 21.7

1.1 1.0

7.0 6.0

Pentanamine Pentane 2-Pentanone Pentyl acetate Petroleum ether Propane 1,3-Propanediol Propanol Propene Propanamine Propionaldehyde Propyl acetate Propylene oxide Propyl nitrate Pyridine

Vinyl acetate Vinyl butyrate Vinyl chloride Vinyl fluoride Xylene, m- and pXylene, o-

260 505 360 550 450 371 440 460 318 207 450

371 190 414 427 461 530 465

SECTION 5

THERMODYNAMIC PROPERTIES

ENTHALPIES AND GIBBS (FREE) ENERGIES OF FORMATION, ENTROPIES, AND HEAT CAPACITIES . . . . . . . . . . . . . . . Table 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds . . . . . . . . . . . . . . . . . . . . . . Table 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds . . . . . . . . . . . . . . . . . CRITICAL PHENOMENA . . . . . . . . . . . . . . . . . . . . . . Table 5.3 Critical Properties . . . . . . . . . . . . . . . . . . Table 5.4 Group Contributions for the Estimation of Critical Properties . . . . . . . . . . . . . . . . . .

5.1

. .

5.2

. .

5.3

. . . . . .

5.44 5.75 5.75

. .

5.88

5.2

SECTION 5

ENTHALPIES AND GIBBS (FREE) ENERGIES OF FORMATION, ENTROPIES, AND HEAT CAPACITIES The tables in this section contain values of the enthalpy (Hf) and Gibbs (Gf, free) energy of formation, entropy (S), and heat capacity (Cp) at 298.15 K (25 C). The tables cover common organic compounds. No values are given in these tables for metal alloys or other solid solutions, for fused salts, or for substances of undefined chemical composition. For a more complete listing of compounds see the tables in Selected Values of Chemical Thermodynamical Properties, by D. D. Wagman et al., National Bureau of Standards Technical Notes 270-3, 270-4, 270-5, 270-6, 270-7, and 270-8, Washington; JANAF Thermochemical Tables, by D. R. Stull and H. Prophet, National Bureau of Standards Publication 37, Washington; supplements to JANAF appearing in J. Phys. Chem. Ref. Data; D. R. Stull, E. F. Westrum, Jr., and G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, Wiley-Interscience, New York, 1969; and I. Barin and O. Knacke, Thermochemical Properties of Inorganic Substances, Springer-Verlag, Berlin, 1973. The values of the thermodynamic properties of the pure substances given in these tables are, for the substances in their standard states, defined as follows: Pure solid (c) or liquid (liq). The substance is in the condensed phase under a pressure of 1 atm. Gas (g). The standard state is the hypothetical ideal gas at unit fugacity, in which state the enthalpy is that of the real gas at the same temperature and at zero pressure. The values of Hf  and Gf  given in the tables represent the change in the appropriate thermodynamic quantity when one gram formula weight of the substance in its standard state is formed, isothermally at the indicated temperature, from the elements, each in its appropriate standard reference state. The standard reference state at 25 C for each element has been chosen to be the standard state that is thermodynamically stable at 25 C and 1 atm pressure. The standard reference states are indicated in the tables by the fact that the values of Hf  and Gf  are exactly zero. The values of S  represent the virtual or “thermal” entropy of the substance in the standard state at 298.15 K, omitting contributions from nuclear spins. Isotope mixing effects are also excluded except in the case of the 1H–2H system. The physical state of each substance is indicated in the column headed “State” as crystalline solid (c), liquid (liq), gaseous (g), or amorphous (amorp). Solutions in water are listed as aqueous (aq). Solutions in water are designated as aqueous, and the concentration of the solution is expressed in terms of the number of moles of solvent associated with 1 mol of the solute. If no concentration is indicated, the solution is assumed to be dilute. The standard state for a solute in aqueous solution is taken as the hypothetical ideal solution of unit molality (indicated as std state, m1). In this state the partial molal enthalpy and the heat capacity of the solute are the same as in the infinitely dilute real solution (aq. m).

5.3

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds

Substance Acenaphthene Acenaphthylene Acetaldeyde Acetaldoxime Acetamide Acetamidoguanidine nitrate 1-Acetamido-2nitroguanidine 5-Acetamidotetrazole Acetanilide Acetic acid Ionized; std state, m  1 Nonionized; std state, m1 Acetic anhydride Acetone Acetone glyceraldehyde Acetonitrile Acetophenone Acetyl radical N-Acetylbenzidine Acetyl bromide Acetyl chloride Acetylene Std state, m  1 Acetylenedicarbonitrile Acetylene dicarboxylic acid Acetyl fluoride N-Acetylhydrazobenzene o-Acetylhydroxybenzoic acid N-Acetylimidazole Acetyl iodide 4-Acetylresorcinol

State

Hf , kcal · mol1

c c liq g c liq c c

16.8 44.7 45.96 39.76 18.6 19.5 76.0 118.1

c

46.3

c c liq g aq aq

1.2 50.3 115.71 103.93 116.16 116.70

liq g liq g liq liq g liq g g c liq liq g g aq liq g c

149.14 137.60 59.18 51.78 180 12.8 21.00 34.07 20.76 4.0 38.0 53.5 65.44 58.30 54.19 50.54 119.6 127.50 138.1

liq c c

112.4 2.0 194.93

c liq c

28.6 39.3 137.1

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

30.64 31.86

38.3 63.15

65.6 13.06

93.2 90.03 88.29 94.78

38.2 67.52 20.7 42.7

29.7 15.90 1.5

116.82 113.93 37.22 36.58

64.2 93.20 47.9 70.49

23.7 25.24 4.06 0.44

35.76 58.19 59.62 89.12

21.86 12.48

49.73 46.29 50.00 51.88

48.0 70.47 48.00 29.5

28 16.21 10.50

122.10

69.31

20.53

23.78 30.22 17.90

5.4

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance N-Acetyltetrazole Acridine Acrolein Acrylic acid Acrylonitrile Adenine Adipic acid Aetioporphyrin I Aetioporphyrin II -Alanine D L DL

Alanine anhydride -Alanylglycine DL L DL-Alanylphenylalanine Alanylphenylalanyl anhydride Allantoin (5-ureidohydantoin) Allomucic acid Alloxan monohydrate Alloxantin dihydrate Allyl radical 1-Allyl-5-allylaminotetrazole 1-Allyl-5-aminotetrazole 2-Allyl-5-aminotetrazole Allyl chloride Allylcyclopentane Allyl ethyl sulfoxide Allyl trichloroacetate Amalic acid Amarine p-Aminoacetophenone 3-Aminoacridine 5-Aminoacridine 2-Aminobenzoic acid 3-Aminobenzoic acid

State

Hf , kcal · mol1

Gf , kcal · mol1

S , cal · deg1 · mol1

c c liq g liq g liq g c c liq c c

19.49 44.8 29.97 20.50 91.8 80.36 36.1 44.20 23.21 237.60 235.51 6.0 0.4

c c c c

134.03 133.96 134.55 128.0

88.23 88.49 88.92

31.6 30.88 31.6

c c c c

185.64 197.52 170.2 89.3

117.00 127.30

51.0 46.62

c

171.50

106.65

46.6

c c c g c

142 239.08 510.3 38 83.7

182.08

44.6

c c g liq liq liq c c c c c c c

63.4 67.6 0.15 15.74 41.83 94.5 367.0 63 70.2 39.8 38.1 95.8 98.2

10.42

73.29

C p, cal · deg1 · mol1

16.17 15.45 68.37

75.29

18.59

46.68 71.58

65.47 36.1

15.24

177.17

18.01

5.5

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 4-Aminobenzoic acid 2-Aminobiphenyl 4-Aminobiphenyl 1-Aminobutane (butylamine) 2-Aminobutane (sec- butylamine) 4-Aminobutanoic acid 2-Aminoethanesulfonic acid Ionized; std state, m  1 Nonionized; std state, m1 2-Aminohexanoic acid (norleucine) 4-Aminohexanoic acid 5-Aminohexanoic acid 6-Aminohexanoic acid 3-Amino-2-methylpropane (2-butylamine) 5-Aminopentanoic acid 5-Aminotetrazole 5-Aminotetrazole nitrate 3-Amino-1,2,4-triazole Amygdalin 1,2-Anyhydroglucose3,5,6-triacetate Aniline Anisine Anisoyl glycine Anthracene 9,10-Anthracenedione -D-Arabinose -L-Arabinose D-Arabonic acid--lactone L-Arginine D-Arginine L-Ascorbic acid (vitamin C) L-Asparagine L-Aspartic acid Azobenzene cis trans

State

Hf , kcal · mol1

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

c c c liq

98.8 26.8 19.4 30.52

g g

22.00 24.90

11.76 9.71

86.76 83.90

28.33 27.99

c c

138.1 187.7

134.3

36.8

33.6

aq aq

171.92 181.92

121.76 134.12

47.8 55.7

c

152.7

c c c liq

154.5 153.7 152.7 31.68

c c c c c c

144.5 49.7 6.6 18.4 455 411.7

liq g c c c c c c c c c c

7.55 20.76 51 180.9 29.0 49.6 252.84 252.84 238.2 148.66 149.05 278.34

35.63 39.84

45.72 76.28

45.90 25.91

68.30

49.58

49.7

57.43

59.9

c c

188.50 232.47

126.73 174.53

41.7 40.66

c c

86.7 76.6

5.6

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

State

Hf , kcal · mol1

Gf , kcal · mol1

84.10

Azodicarbamide Azulene

c g

69.90 66.90

Barbituric acid Benzaldehyde

c liq g c c c c c

152.2 21.23 9.57 48.42 22.3 41 38.3 55.4

liq g liq g c c c c g c c c c liq liq liq c c c g liq liq

11.71 19.82 15.32 26.66 16.9 36.8 92.03 103.0 52.30 8.0 44.33 59.74 147.9 25.58 39.17 12.31 129.6 135.7 44.2 45 38.49 5.6

liq c liq liq liq liq liq g g g g

7.8 44.2 1.17 13.8 10.4 36.30 6.27 0.33 9.09 6.39 3.85

Benzamide Benzanilide 1,2-Benzanthracene 2,3-Benzanthracene 1,2-Benzanthra-9,10quinone Benzene Benzenethiol (thiophenol) Benzidine Benzil Benzoic acid Benzoic anhydride Benzonitrile Benzophenone p-Benzoquinone Benzotriazole DL-Benzoylalanine Benzoyl bromide Benzoyl chloride Benzoyl iodide Benzoylphenylalanine Benzoyl sarcosine 3,4-Benzphenanthrene Benzyl radical Benzyl alcohol Benzyl bromide (2-bromotoluene) Benzyl chloride N-Benzyldiphenylamine Benzyl ethyl sulfide Benzyl iodide Benzyl mercaptan Benzyl methyl ketone Benzyl methyl sulfide Bicyclo[4.1.0]heptane Bicyclo[3.1.0]hexane Bicyclo[4.2.0]octane Bicyclo[5.1.0]octane

S , cal · deg1 · mol1

80.75

C p, cal · deg1 · mol1

30.69

2.24 5.85

85.79

51.48

29.72 30.99 32.02 35.28

41.41 64.34 53.25 80.51

41.40 25.07

58.62

40.05

34.97

62.33 33.5

76.73 58.6

26.07

6.57

51.8

19.52

5.7

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Bicyclopropyl Biphenyl Biphenylene N,N-Bisuccinimide Brassidic acid Bromal Bromal hydrate Bromobenzene 4-Bromobenzoic acid 1-Bromobutane 2-Bromobutane Bromochlorodifluoromethane Bromochlorofluoromethane Bromochloromethane Bromodichlorofluoromethane Bromodichloromethane Bromodifluoromethane Bromoethane Bromoethene (vinyl bromide) Bromofluoromethane 1-Bromoheptane 1-Bromohexane Bromoiodomethane Bromomethane 2-Bromo-2-methylpropane 1-Bromooctane 1-Bromopentane 1-Bromopropane 2-Bromopropane N-Bromosuccinimide Bromotrichloromethane Bromotrifluoromethane Brucine 1,2-Butadiene 1,3-Butadiene Butadiyne (biacetylene)

State

Hf , kcal · mol1

g c liq liq c c liq c liq c g liq g g

30.9 24.02 28.5 84.4 169.5 214 31.13 112 14.5 90.4 25.65 37.2 28.70 112.7

g

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

60.75 62.07

49.2 59.8

38.80

30.12

52.0

37.17

3.08 4.60 6.16 107.18

88.39

26.13

88.50 76.14

26.48

70.5

66.58

72.88

g g

12.0 64.4

9.39 58.98

68.67 78.87

g g liq g g

14.0 110.8 21.99 15.30 18.73

10.16 106.90 6.64 6.29 19.30

75.56 70.51 47.5 68.71 65.83

g liq liq g g liq g liq liq g g g c g g c g g g

60.4 52.21 46.42 12.0 9.02 39.3 32.00 58.57 40.68 30.87 21.00 23.20 80.35 8.9 155.1 188.6 38.77 26.33 113.00

57.71

65.97

9.36 6.75

73.49 58.76

10.15

6.73

79.34

27.85

1.37 5.37 6.51

97.70 79.08 75.53

31.60 20.66 21.37

2.96 148.8

79.55 71.16

16.57

47.43 36.01 106.11

70.03 66.62 59.76

19.15 19.01 17.60

24.1 15.45 13.26

5.8

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Butane 1,2-Butanediamine 2,3-Butanedione (diacetyl) 1,4-Butanedithiol 1-Butanethiol (butyl mercaptan) 2-Butanethiol 1-Butanol 2-Butanol 2-Butanone (methyl ethyl ketone) 1-Butene 2-Butene cis trans 1-Buten-3-yne tert-Butoxy radical tert-Butyl radical N-Butylacetamide Butyl acetate tert-Butylamine Butylbenzene sec-Butylbenzene tert-Butylbenzene sec-Butyl butyrate Butyl chloroacetate Butyl 2-chlorobutyrate Butyl 3-chlorobutyrate Butyl 4-chlorobutyrate Butyl 2-chloropropionate Butyl 3-chloropropionate Butyl crotonate Butylcyclohexane Butylcyclopentane Butyl dichloroacetate Butyl ether tert- Butyl hydroperoxide

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

liq g liq liq liq liq

35.29 30.15 28.74 87.44 25.11 29.79

3.60 4.10

55.2 74.12

0.97

65.96

g liq g liq g liq g liq

21.05 31.13 23.00 78.18 65.65 81.88 69.94 65.29

2.64 0.04 1.29 38.84 36.04 42.31 40.06 36.18

89.68 64.87 87.65 54.1 86.7 53.8 85.6 57.08

28.24

g g

56.26 0.03

34.91 17.04

80.81 73.04

24.59 20.47

g g g g g liq liq liq g liq g liq liq liq liq liq liq liq liq liq liq g g liq liq g liq

1.67 2.67 72.80 24.7 6.7 91.02 126.52 35.97 28.65 18.67 18 C 3.30 15.87 16.90 141.6 128.7 156.6 146.0 147.7 136.7 133.4 111.8 50.95 40.22 131.5 156.1 87.2 70.2

15.74 15.05 73.13

71.90 70.86 66.77

18.86 20.99 17.49

6.90 27.50 34.58

80.76

28.67

105.04

41.85

13.49 14.67

109.58 109.04

49.50 42.42

114.96

48.82

State

23.29

28.51 42.31 26.29 47.5 27.08 37.98

5.9

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Butyllithium Butyl trichloroacetate 1-Butyne (ethyl acetylene) 2-Butyne (dimethylacetylene) Butyraldehyde Butyramide Butyric acid Butyronitrile Caffeine (methyl theobromine) Capric acid (decanoic acid) Caproic acid (hexanoic acid) -Caprolactam Caprylic acid (octanoic acid) Carbazole Carboxyl radical CCH radical Cellobiose Chloroacetamide Chloroacetic acid Ionized Nonionized; std state, m1 Chloroacetyl chloride 2-Chlorobenzaldehyde 3-Chlorobenzaldehyde 4-Chlorobenzaldehyde Chlorobenzene 2-Chlorobenzoic acid 3-Chlorobenzoic acid 4-Chlorobenzoic acid Chlorobenzoquinone 1-Chlorobutane 2-Chlorobutane 2-Chlorobutyric acid 3-Chlorobutyric acid 4-Chlorobutyric acid Chlorocyclohexane 2-Chloro-1,1difluoroethylene Chlorodifluoromethane

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

liq liq g g

31.6 130.6 39.48 34.97

48.30 44.32

69.51 67.71

19.46 18.63

g c liq g

49.00 87.5 127.59 8.14

27.43

82.44

24.52

90.27 25.97

54.1 77.98

42.1 23.19

c

76.2

c

170.59

liq

139.71

c liq

78.54 151.93

22.72

40.3

c g g c c c, l aq aq

30.3 54 114 532.5 80.9 122.3 119.81 118.92

105

49.6

8.87

liq liq liq c liq c c c c g g liq liq liq liq g

68.0 28.4 30.2 35.1 2.58 95.3 101.2 102.19 52.7 35.20 38.60 137.6 133.0 135.4 49.54 79.2

21.32

50.0

35.9

9.27 12.78

85.58 85.94

25.71 25.93

72.90

72.28

g

115.6

108.1

67.12

State

13.35

5.10

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Chloroethane (ethyl chloride) Chloroethylene (vinyl chloride) Chloroethyne Chlorofluoromethane Chloroform Chloroiodomethane Chloromethane (methyl chloride) Chloromethyloxirane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane 1-Chloronaphthalene 2-Chloronaphthalene 1-Chloropentane 3-Chorophenol 4-Chlorophenol 1-Chloropropan-2,3-diol 2-Chloropropan-1,3-diol 1-Chloropropane 2-Chloropropane 3-Chloro-1-propene (allyl chloride) 2-Chloropropionic acid 3-Chloropropionic acid N-Chlorosuccinimide Chlorotrifluoromethane Chlorotrinitromethane Chrysene Cinchonamine Cinchonidine Cinchonine Cinnamic acid cis trans Cinnamic anhydride Citraconic acid Citric acid Citric acid monohydrate Codeine monohydrate Coniine Creatine Creatine hydrate Creatinine

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g

26.83

14.46

65.91

14.97

g

8.5

12.4

63.07

12.84

g g liq g g g

51 63.2 31.6 24.60 3.0 19.59

47 57.11 17.17 16.76 3.69 13.97

57.81 63.16 48.5 70.63 70.78 55.97

12.98 11.24

liq g g liq c g c c liq liq g g g

35.48 38.10 43.80 13.0 13.2 41.80 49.4 47.3 125.58 123.71 31.10 35.00 0.15

11.87 15.32

84.56 77.00

25.93 27.30

8.94

94.89

31.18

12.11 14.94 10.42

76.27 72.70 73.29

20.23 20.87 18.01

liq c c g liq c c c c

125.0 131.4 85.58 169.20 6.54 34.7 10.4 7.1 7.4

159.38

68.16

15.98

c c c c c c c liq c c c

72.0 80.53 83.1 197.04 369.0 439.4 151.2 57.6 128.16 199.1 56.77

295.5 352.0

39.73 67.74

1.276

63.32

45.3

6.97

40.10

State

15.63 9.74

5.11

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance o-Cresol (2-methylphenol) m-Cresol (3-methylphenol) p-Cresol (4-methylphenol) m-Cresol acetate Crotonic acid cis trans trans-Crotononitrile Cyanamide 1-Cyanoguanidine 3-Cyanopyridine 5-Cyanotetrazole 4-Cyanothiazole Cyclobutane Cyclobutene Cyclododecane Cycloheptane Cycloheptanone 1,3,5-Cycloheptatriene 1,3-Cyclohexadien-5-yl radical Cyclohexane Cyclohexane- 1,2dicarboxylic acid cis trans Cyclohexanethiol Cyclohexanol Cyclohexanone Cyclohexene Cyclohexen-3-yl radical 1-Cyclohexenylmethanol Cyclohexyl radical Cyclooctane Cyclooctanone 1,3,5,7-Cyclooctatetraene Cyclopentadiene Cyclopentane Cyclopentane-1,2-diol cis trans

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g

30.74

8.86

85.47

31.15

g

31.63

9.69

85.27

29.27

g

29.97

7.38

83.09

29.75

liq

89.41

liq c g c c c c c g g c liq liq liq g

83 102.9 35.77 14.05 5.4 46.23 96.1 52.63 6.37 31.00 73.29 37.47 71.5 34.22 49.4

46.22

71.31

19.62

42.9

30.90

28.40

26.30 41.76

63.43 62.98

17.26 16.03

12.92

57.97

29.42

58.09

51.30

38.90

liq g

37.34 29.43

6.37 7.59

48.84 71.28

37.4 25.40

c c g liq g liq g g liq g liq liq liq g liq g

229.7 232.0 22.80 83.22 55.00 9.28 1.28 29 91.4 13 40.58 77.9 60.93 32.00 25.28 18.46

31.87 21.69 24.28 25.54

47.7 77.00 51.67 74.27

26.21 34.9 25.10

18.60

62.62

85.70 42.86 8.70 9.23

52.65 64.00 48.82 70.00

c c

115.9 117.1

State

30.80 19.84

5.12

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Cyclopentanethiol Cyclopentanol Cyclopentanone Cyclopentene 1-Cyclopentenylmethanol Cyclopentyl-1-thiaethane Cyclopropane Cyclopropene Cyclopropyl radical L-Cysteine L-Cystine Decahydronaphthalene (decalin) cis trans Decanal Decane 1,10-Decanediol 1-Decanethiol 1-Decanoic acid 1-Decanol 1-Decene 1-Decyne Deoxybenzoin Desoxyamalic acid Diacetamide Diacetyl peroxide o-Diallyl phthalate Dialuric acid 2,6-Diaminopyridine Diamylose Diazomethane Dibenzoylethane Dibenzoylethylene Dibenzoylmethane Dibenzoyl peroxide Dibenzyl Dibenzyl ketone Dibenzyl sulfide Dibenzyl sulfone

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g liq liq g liq g liq g g g g c c

11.45 71.74 56.24 46.03 1.02 7.87 8.2 15.41 12.74 66.0 55 124.5 245.7

13.63 30.55

86.38 49.2

25.79

25.93 26.48

48.10 69.23

29.24 17.95

24.95 68.42

56.75 58.38

13.37

liq liq g liq c liq g c liq g liq g c c c liq liq c c c g c c c c c c c c

52.45 55.14 79.09 71.95 165.74 66.07 50.54 170.59 114.6 96.0 41.73 9.85 16.96 285.7 117 127.9 131.6 314.4 1.56 850 46.0 61.1 27.4 53.6 100 10.53 20.1 23.74 42.1

16.47 13.79 15.90 4.19

63.34 63.32 138.28 101.70

55.45 54.61 57.29 75.16

14.68

145.82

61.08

31.6 24.9 25.10 60.28

10.2.9 142.8 101.58 125.36

52.06

58.02

12.55

62.15

64.4

61.0

State

59.1 52.51

5.13

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 1,2-Dibromobutane Dibromochlorofluoromethane Dibromochloromethane 1,2-Dibromocycloheptane 1,2-Dibromocyclohexane 1,2-Dibromocyclooctane Dibromodichloromethane Dibromodifluoromethane 1,2-Dibromoethane Dibromofluoromethane Dibromomethane 1,2-Dibromopropane Dibutylborinic acid Dibutyl ether Dibutylmercury Di-tert-butyl peroxide Dibutyl o-phthalate Dibutyl sulfate Dibutyl sulfite Dibutyl sulfone Dichloroacetic acid Ionized Nonionized Dichloroacetylene 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene Dichlorodifluoromethane 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene Dichlorofluoromethane Dichloromethane 1,2-Dichloropropane 1,3-Dichloropropane 2,2-Dichloropropane Dicyanoacetylene

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g g

23.70 55.4

3.14 53.40

97.70 81.99

g liq liq liq g g liq g g g liq g liq liq c liq liq c liq aq aq g g g g g liq g liq g liq g liq g g g liq g g g g liq

5.0 37.67 38.8 41.41 7.0 102.7 19.4 53.4 3.53 17.40 146.3 79.80 23.4 91.0 201 216.1 165.6 145.76 119.0 122.4 120.4 50 7.16 6.32 5.50 117.90 38.3 31.10 39.49 31.00 5.8 0.30 6.6 0.45 1.00 68.10 29.7 22.80 39.60 38.60 42.00 119.6

4.50

78.31

4.67 100.16 5.0 52.84 3.87 4.22

83.23 77.66 53.37 75.70 70.10 89.90

13.04 24.57

21.16

119.60

48.76

47 19.76 18.78 18.44 108.51 18.1 17.52 19.03 17.65 5.85 5.78 5.27 5.82 6.35 60.77 16.83 16.46 19.86 19.74 20.21

65 81.61 82.09 80.47 71.91 50.61 72.91 49.84 73.66 48.17 68.85 47.42 69.20 69.29 70.04 42.7 64.61 84.80 87.76 77.92

15.67 27.12 27.20 27.22 17.31 30.18 18.25 30.9 18.80 26.60 16.02 27 15.55 15.93 14.58

State

30.38

32.51

12.16 23.47 23.81 25.30

5.14

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 1,4-Dicyano-2-butyne Dicyclohexadiene Dicyclopentadiene Dicyclopentyl 2,2-Diethoxypropane Diethylamine Diethylbarbituric acid (veronal) 1,2-Diethylbenzene 1,3-Diethylbenzene 1,4-Diethylbenzene Diethylenediamine Diethylene glycol Diethyl ether (ethyl ether) Diethylmercury Diethylmethyl phosphonate Diethylnitramine Diethyl oxalate Diethyl peroxide Diethyl o-phthalate Diethyl selenide Diethyl sulfate Diethyl sulfite Diethyl sulfone Diethyl sulfoxide Diethylzinc 1,2-Difluorobenzene 1,3-Difluorobenzene 1,4-Difluorobenzene 2,2-Difluorobiphenyl 4,4-Difluorobiphenyl 2,2-Difluorochloroethylene 1,1-Difluoroethane 1,1-Difluoroethylene Difluoromethane 9,10-Dihydroanthracene 1,2-Dihydronaphthalene 1,4-Dihydronaphthalene 4H-Dihydropyran 5,12-Dihydrotetracene 2,3-Dihydrothiophene

State

Hf , kcal · mol1

c liq c liq liq g c

87.6 6.3 27.9 41.8 128.83 17.30 178.7

g g g c liq g liq

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

17.23

84.18

27.66

4.53 5.22 5.32 3.2 150.2 136.5 65.30

33.72 32.67 32.95 57.4

103.81 104.99 103.73 20.5

43.63 42.27 42.10

27.88

105.4 60.5

32.3 40.8

g liq liq

60.26 7.1 245.3

29.24

81.90

26.89

liq liq liq liq liq liq liq c liq liq liq g g c c g g g g c liq liq liq c liq

25.4 192.51 53.4 186 23.0 194.28 143.50 123.13 63.97 4.0 79.04 74.09 73.43 70.73 70.91 75.4 119.70 82.50 108.24 15.87 18.0 21.0 37.5 25.44 12.73

59.41 61.43 60.43

53.20 76.57 75.43

38.01 25.40 25.55

69.1 105.87 76.84 101.66

72.39 67.50 63.38 58.94

17.23 16.24 14.14 10.25

5.15

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 2,5-Dihydrothiophene 1,2-Dihydroxybenzene 1,3-Dihydroxybenzene 1,2-Diiodobenzene 1,3-Diiodobenzene 1,4-Diiodobenzene 1,2-Diiodoethane Diiodomethane Diisopropyl ether Diisopropyl ketone Diisopropylmercury 1,2-Dimethoxybenzene Dimethoxyborane 1,2-Dimethoxyethane 2,2-Dimethoxypropane cis-,-Dimethylacrylic acid Dimethyl adipate Dimethylamine Std state, m  1 (CH3)2NH2; std state, m  1 Dimethylaminotrimethylsilane N,N-Dimethylaniline 2,2-Dimethylbutane 2,3-Dimethylbutane 2,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene 3,3-Dimethyl-1-butene 2,3-Dimethyl-2-butenoic acid Dimethylcadmium Dimethylchlorosilane 1,1-Dimethylcyclohexane 1,2-Dimethylcyclohexane cis trans 1,3-Dimethylcyclohexane cis trans 1,4-Dimethylcyclohexane cis trans

State

Hf , kcal · mol1

liq c c c c c g g liq g g liq liq liq liq liq c

11.31 86.3 87.95 41.2 44.7 38.4 15.90 28.30 83.94 76.20 74.40 3.1 69.4 144.5 90.02 108.92 117.3

liq g aq aq

211.9 4.50 16.88 28.74

liq

66.8

liq g g g g g c

8.2 44.35 42.49 13.32 14.15 10.31 108.9

g liq liq g

9.528 79.8 52.31 43.26

g g

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

50.20 50.00

35.9 35.3

31.6 31.3

18.76 24.24 21.1 29.13

83.30 73.95 70.4 93.27

19.67 13.80

16.25 13.85 0.80

65.24 31.8 41.2

16.50

2.20 0.98 18.89 18.18 23.46

85.62 87.42 87.39 87.15 82.16

33.91 33.59 34.29 29.54 30.23

72.40

31.5

6.34 8.42

63.87 87.24

36.90

41.15 43.02

9.85 8.24

89.51 88.65

37.40 38.00

g g

44.16 42.20

7.13 8.68

88.54 89.92

37.60 37.60

g g

42.22 44.12

9.07 7.58

88.54 87.19

37.60 37.70

37.83

5.16

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 1,1-Dimethylcyclopentane 1,2-Dimethylcyclopentane cis trans 1,3-Dimethylcyclopentane cis trans Dimethyldichlorosilane cis-2,4-Dimethyl-1,3dioxane 4,5-Dimethyl-1,3-dioxane 5,5-Dimethyl-1,3-dioxane 4,4-Dimethyldiphenylamine Dimethyl ether N,N-Dimethylformamide Dimethylfulvene Dimethyl fumarate Dimethyl glutarate Dimethylglyoxime 2,2-Dimethylhexane 2,3-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane 2,2-Dimethyl-3-hexene cis trans 5,5-Dimethylhydantoin 1,1-Dimethylhydrazine 1,2-Dimethylhydrazine Dimethyl maleate Dimethylmaleic anhydride Dimethyl malonate Dimethylmercury Dimethylnitramine Dimethyl oxalate 2,2-Dimethylpentane

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g

33.05

9.33

85.87

31.86

g g

30.96 32.67

10.93 9.17

87.51 87.67

32.06 32.14

g g g liq

32.47 31.93 110.2 111.79

9.37 9.91

87.67 87.67 80.16

32.14 32.14 24.17

liq liq c

108.32 110.53 2.8

g liq liq liq liq c liq g liq g liq g liq g liq g liq g

43.99 57.2 21.5 174.3 205.9 42.51 62.63 53.71 60.40 51.13 61.47 52.44 62.26 53.21 61.58 52.61 60.23 50.91

26.99

63.83 28.5

15.73 37.45

0.71 2.56 2.17 4.23 0.89 2.80 0.60 2.50 1.23 3.17 2.03 4.14

79.33 103.06 81.91 106.11 82.62 106.51 80.96 104.93 81.12 104.70 82.97 107.15

liq liq c liq liq liq c liq liq c liq g

30.22 34.64 126.4 11.8 13.3 168.2 139.0 190.2 14.0 16.9 181.0 49.27

49.4 50.8

47.32 47.60

39.21 40.88

0.02

93.90

39.67

State

5.17

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,7-Dimethylphenanthrene 4,5-Dimethylphenanthrene 9,10-Dimethylphenanthrene Dimethyl m-phthalate Dimethyl o-phthalate Dimethyl p-phthalate 2,2-Dimethylpropane 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,5-Dimethylpyridine 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine Dimethyl succinate 1,1-Dimethylsuccinic acid 1,2-Dimethylsuccinic acid cis trans Dimethyl sulfate Dimethyl sulfite Dimethyl sulfone Dimethyl sulfoxide 3,3-Dimethyl-2-thiabutane 2,2-Dimethylthiacyclopropane 2,2-Dimethyl-3-thiapentane 2,4-Dimethyl-3-thiapentane 2,3-Dinitroaniline 2,4-Dinitroaniline 2,5-Dinitroaniline 2,6-Dinitroaniline 3,4-Dinitroaniline 3,5-Dinitroaniline 2,4-Dinitroanisole 2,6-Dinitroanisole 1,2-Dinitrobenzene 1,3-Dinitrobenzene 2,4-Dinitrophenol 2,6-Dinitrophenol 2,4-Dinitroresorcinol

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g g g c c c

47.62 48.28 48.17 8.70 21.26 11.4

0.16 0.74 0.63

98.96 94.80 95.53

39.67 39.67 39.67

c liq c g liq liq liq liq liq liq liq c

171 162 170 39.67 4.62 3.85 4.45 3.02 4.36 5.36 199.6 236.08

0.364

73.23

29.07

c c liq liq c liq liq liq

233.6 235.1 175.23 125.07 107.8 48.6 37.49 5.78

72.3 23.7

34.77 45.0

35.2

liq g c c c c c c c c c c c c c

44.7 33.76 2.8 16.3 10.6 12.1 7.8 9.3 44.6 45.2 2.06 4.04 55.6 50.2 99.3

6.48

99.30

40.45

50.56 44.13

51.7 52.8

State

5.18

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 4,6-Dinitroresorcinol 2,4-Dinitrotoluene 2,6-Dinitrotoluene 1,4-Dioxane 1,3-Dioxane 1,4-Dioxatetralin Dioxindole 1,3-Dioxolane Dipentene N,N-Diphenylacetamide Diphenylamine 1,4-Diphenylbutadiene cis,cis trans,trans Diphenylbutadiyne 1,4-Diphenylbutane 1,4-Diphenyl1,4-butanedione 1,4-Diphenyl-2-butene1,4-dione Diphenylcarbinol Diphenyl carbonate Diphenyldichlorosilane Diphenyl disulfide Diphenyl disulfone 1,1-Diphenylethane 1,2-Diphenylethane 1,1-Diphenylethene Diphenyl ether Diphenylethyne Diphenylfulvene Diphenylmercury Diphenylmethane Diphenyl sulfide Diphenyl sulfone Diphenyl sulfoxide Dipropyl ether Dipropylmercury Dipropyl sulfate Dipropyl sulfite Dipropyl sulfone Dipropyl sulfoxide 2,3-Dithiabutane 5,6-Dithiadecane

State

Hf , kcal · mol1

c c c liq g liq liq c g liq c c

105.1 17.1 12.2 84.47 75.30 89.99 60.9 76.9 71.1 12.1 10.3 31.07

c c c c c

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

44.96 43.21

46.67 71.65

47.51 42.73 123.91 2.36 61.24

1.87

77.6

c

27.55

26.64

76.3

c c liq c c liq liq liq liq c c c liq liq c c g liq liq liq liq liq liq g

25.04 95.93 66.5 35.8 153.59 11.7 12.31 41.21 3.48 74.66 7.1 66.8 21.25 39.1 53.71 2.40 70.00 5.0 205.22 154.52 130.94 78.65 14.82 37.86

42.05

66.54

58.58 63.87

80.28 64.6

34.47

69.62

66.19

57.2

55.7

25.23

100.98

37.83

1.67 12.87

56.26 136.91

34.92 55.23

22.48

5.19

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

State

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1 2.28

72.90

4.56

89.28

6.71

117.26

89.86

32.96 64.22

147.78 143.98

64.43 63.44

3,4-Dithiahexane 1,3-Dithian-2-thione 4,5-Dithiaoctane N,N-Dithiodiethylamine 1,3-Dithiolan-2-thione Di-p-tolyl sulfone Divinyl ether Divinyl sulfone Dodecane Dodecanoic acid 1-Dodecene 1-Dodecyne Dulcitol

liq c liq liq c c g liq liq c g g c

28.69 3.1 40.95 29.1 3.1 74.32 9.53 49.5 84.16 185.14 39.52 0.01 321.9

Eicosane Eicosanoic acid (arachidic acid) 1-Eicosene Ergosterol meso-Erythritol Ethane 1,2-Ethanedithiol Ethanethiol Ethanol

g c

108.93 241.9

28.04

223.26

110.73

g c c g liq g liq g g g liq g liq g liq liq g g c

78.93 188.8 127.56 20.24 12.83 11.02 66.20 56.03 6 26.0 114.49 105.86 96.95 11.00 0.9 2.98 7.12 12.32 124.4

49.03

222.26

108.15

152.12 7.84

39.9 54.76

12.54

1.12 41.63 40.13

70.77 38.49 67.54

17.37 26.76 15.64

31 79.52 78.25

59.2 62.0 86.70

27.16

8.91 45.10 28.61 31.21 19.11

68.08 57.2 60.99 86.15 90.01

17.36

g liq liq liq liq g liq g c

26.83 100.4 50.72 25.50 39.08 30.37 141.6 12.50 138.9

14.46

65.91

14.97

6.95

67.14

8.92 10.65

67.00 90.42

31.49

16.31

52.39

10.24

Ethoxy radical Ethyl radical Ethyl acetate Ethyl allyl sulfone Ethylamine N-Ethylaniline Ethylbenzene 2-Ethyl-1-butene Ethyl carbamate (urethane) Ethyl chloride Ethyl crotonate Ethylcyclohexane 1-Ethylcyclohexene Ethylcyclopentane Ethyldiethylcarbamate Ethylene Ethylene carbonate

30.69 31.92

5.20

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

State

Ethylene chlorohydrin 1,2-Ethylenediamine

liq liq aq, 200 Ethylenediaminetetraacetic c acid (EDTA) Ethylenediammonium c chloride aq, 5000 Ethylene glycol liq (2,1-ethanediol) g aq, 1 Ethyleneimine (azirane) g Ethylene oxide g 2-Ethyl-1-hexanal liq 2-Ethyl-2-hexanal liq 3-Ethylhexane liq Ethylidenecyclohexane liq Ethyl isovalerate liq Ethyllithium c Ethylmercury bromide c Ethylmercury chloride c Ethylmercury iodide c Ethyl methyl ether g Ethyl nitrate g Ethyl nitrite g 3-Ethylpentane g Ethyl pentanoate liq Ethyl peroxyl radical g 2-Ethylphenol c 3-Ethylphenol c 4-Ethylphenol c Ethylphosphonic acid c Ethyl propanoate liq 2-Ethylpyridine liq Ethylsuccinic acid c Ethyl thioacetate liq Ethyl -vinylacrylate liq Ethyl vinyl ether g Ethynylbenzene (phenylg acetylene) Fluoranthene Fluoroacetamide Fluoroacetic acid Fluorobenzene 2-Fluorobenzoic acid

c c c g c

Hf , kcal · mol1

Gf , kcal · mol1

70.6 15.06 13.32 420.5

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

50

122.7 115.92 108.70

77.25

39.9

35.8

93.05 109.01 29.50 12.58 83.30 62.44 59.88 21.19 136.5 14.0 25.7 33.7 15.7 51.73 36.80 24.9 45.33 132.2 (2) 49.91 51.21 53.63 251.3 122.16 1.2 236.4 64.01 80.8 33.63 78.22

72.77

77.33

23.20

42.54 3.13

59.90 57.94

12.55 11.54

1.79

84.95

28.12 8.81

74.24 83.25 24.74 98.35

21.45 23.27 23.71 39.67

86.46

76.88

27.46

45.75 118.7 164.5 27.86 135.67

82.60

55.09

16.50

72.33

2.63

79.16

22.57

5.21

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

State

Hf , kcal · mol1

c c g liq g g g liq liq g aq liq g c liq g aq aq

139.13 140.00 62.90 111.3 56.80 67.20 69.00 44.80 52.8 27.70 35.9 60.7 44.5 36.2 101.51 90.49 101.71 101.68

g

195.08

g g g c c c c c c g liq liq c

10.4 204 90 222.1 118 302.2 262.7 193.84 64.11 8.23 47.8 66.05 119.12

c liq

109.7 2.5

c c c

384.8 304.1 343.2

D-Glucaric acid-

c

343.6

3,6-lactone D-Gluconic acid D-Gluconic acid-lactone

c c

379.3 300.3

3-Fluorobenzoic acid 4-Fluorobenzoic acid Fluoroethane 2-Fluoroethanol Fluoromethane 1-Fluoropropane 2-Fluoropropane 4-Fluorotoluene Fluorotrinitromethane Formaldehyde unhydrolyzed Formamide Formanilide Formic acid Ionized; std state, m  1 Nonionized; std state, m1 Dimer Formyl HCO HCO Formyl fluoride N-Formyl-DL-leucine Formyl urea -D-Fructose D-Fucose Fumaric acid Fumaronitrile Furan Furfural Furfuryl alcohol 2-Furoic acid (pyromucic acid) Furylacrylic acid Furylethylene D-Galactonic acid D-Galactose D-Glucaric acid-

1,4-lactone

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

50.44

63.34

14.21

51.09 47.87 48.81 19.06

53.25 72.71 69.82 56.67

8.96 19.75 19.60

26.27 31.02

52.29

8.46

33.71

59.41

10.84

86.38 83.89 83.9 89.0

30.82 59.45 22 39

23.67 10.81 21.0

6.76 201 88

53.66 48.3 59.0

8.27 8.62 9.66

156.70

39.7

0.21

63.86

36.85

51.50

219.60

49.1

15.64

5.22

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

c c c c c c liq liq liq c c c c liq c c c c c liq c c liq c aq aq

304.26 302.76 240.19 241.32 197.3 229.44 143 159.76 217.5 185.80 184.71 265.05 261.90 268.2 277.46 275.48 292.31 306.28 319.64 318.3 489 520 88.6 126.22 112.28 122.85

217.6

50.7

173.87 174.78

45.7 44.98

114.01

48.87

35.9

88.09 75.28 88.62

24.74 26.54 37.84

23.71

aq

123.78

91.82

45.46

liq c

91.1 158.6

c c c g c c c c c c c

178.51 163.9 200.0 50.66 21.63 199.7 13.39 232.10 92.5 288.0 43.72

117.25

45.4

133.23

70.6

11.33

38.3

State

D-Glucose

  D-Glutamic acid L-Glutamic acid L-Glutamine Glutaric acid Glyceraldehyde Glycerol Glyceryl-1-acetate Glyceryl-l-benzoate Glyceryl-2-benzoate Glyceryl-1-caprate Glyceryl-2-caprate Glyceryl-1,3-diacetate Glyceryl-1-laurate Glyceryl-2-laurate Glyceryl-2-myristate Glyceryl-1-palmitate Glyceryl-1-stearate Glyceryl triacetate Glyceryl trilaurate Glyceryl trimyristate Glyceryl trinitrate Glycine Ionized; std state, m  1 Nonionized; std state, m1 NH3CH2COOH; std state, m  1 Glycol acetal Glycolic acid (hydroxyacetic acid) Glycylglycine Glycylphenylalanine Glycylvaline Glyoxal Glyoxime Glyoxylic acid Guanidine Guanidine carbonate Guanidine nitrate Guanidine sulfate Guanine

61.87

5.23

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

State

Hf , kcal · mol1

Guanylurea nitrate

c

102.1

Heptadecane Heptadecanoic acid 1-Heptadecene 1-Heptanal Heptane Heptanedioic acid 1-Heptanethiol

g c g g liq g g liq c

94.15 220.9 64.15 63.10 53.63 44.88 35.76 145.75 241.75

liq g liq g g c g g liq

Heptanoic acid (enanthic acid) 1-Heptanol 1-Heptene 1-Heptyne Hexachlorobenzene Hexachloroethane Hexadecafluoroethylcyclohexane Hexadecafluoroheptane Hexadecane Hexadecanoic acid (palmitic acid) 1-Hexadecanol (cetyl alcohol) 1-Hexadecene Hexafluorobenzene Hexafluoroethane Hexahydroindane cis trans Hexamethylbenzene Hexamethyldisiloxane Hexamethylenetetramine (urotropine) Hexanal Hexanamide Hexane 1-Hexanethiol Hexanoic acid

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

22.01

195.33

94.33

43.00 20.71 0.42 1.91 8.65

194.33 110.34 77.92 102.27 117.89

91.76 40.89 53.76 39.67 44.68

95.8 79.3 23.41 14.89 24.62 31.30 8.10 33.20 799.1

34.0 28.9 21.22 22.90 54.18 0.25 10.56 13.13

76.5 114.8 78.31 101.24 97.44 62.20 105.45 95.30

66.5 42.7 50.62 37.10 36.11 48.11 41.40 32.68

liq g g c

817.6 808.9 89.23 213.3

739.24 737.87 20.00 75.54

134.28 158.88 186.02 108.12

c, II

163.4

23.6

108.0

104.8

liq g liq g g

151.86 59.23 237.27 228.64 320.90

23.08 40.99 211.43 210.18 300.15

145.0 185.02 66.90 91.59 79.30

86.29 52.96 37.43 25.43

g g c liq c liq g c liq g g liq

30.4 31.4 39.19 194.7 30.0 18.7 59.37 101.48 47.52 39.96 30.83 139.71

28.06 129.5 103.92 28.65 23.93

71.66 103.69 39.05 73.28 101.07

61.5 74.42

0.91 0.06 6.65

70.76 92.83 108.58

45.2 34.20 39.21

88.86

35.43

5.24

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Hf , kcal · mol1

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Substance

State

1-Hexanol

liq g liq g

90.7 75.9 17.30 9.96

36.4 32.4 19.93 20.90

69.2 105.5 70.55 91.93

56.6 37.2 43.81 31.63

g g

12.51 12.27

18.22 18.27

92.37 90.97

30.04 31.64

g g g c

11.38 13.01 29.55 145.63

19.84 18.55 52.24 88.33

90.73 89.59 88.13 57.2

29.55 31.75 30.65

c c c c liq c c c c liq c c c c

179 107.2 52.9 87.08 110.2 158.6 140.64 139.8 139.7 162.3 177.9 158.1 19.9 26.47

49.48

33.5

33.9

100.7 99.74 99.55

42.6 42.3 42.0

38.03 37.59 37.08

18.39

34.8

c liq liq c g c c c liq liq g liq g g liq c c

14.5 2.56 26.39 29.8 38.85 72.2 75.7 75.5 23.5 9.6 2.00 3.29 3.29 17.60 38.6 34.5 22.9

36.04 52.00

56.01 51.19

45.47 44.68

44.88

79.84

24.08

3.5 5.10 3.61 3.72 5.65

50.6 70.82 38.9 60.64 81.79

27.5 15.76

1-Hexene 2-Hexene cis trans 3-Hexene cis trans 1-Hexyne Hippuric acid (benzoylglycine) Hydantoic acid Hydantoin Hydrazobenzene Hydroquinone Hydrosorbic acid Hydroxyacetic acid o-Hydroxybenzoic acid m-Hydroxybenzoic acid p-Hydroxybenzoic acid -Hydroxybutyric acid Hydroxyisobutyric acid L-Hydroxyproline 8-Hydroxyquinoline Hypoxanthene (6-oxypurine) Imidazole Indane Indene Indole Iodobenzene 2-Iodobenzoic acid 3-Iodobenzoic acid 4-Iodobenzoic acid Iodocyclohexane Iodoethane Iodomethane 2-Iodo-2-methylpropane 1-Iodonaphthalene 2-Iodonaphthalene 2-Iodophenol

10.54 28.27

5.25

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

State

Hf , kcal · mol1

3-Iodophenol 4-Iodophenol 1-Iodopropane 2-Iodopropane 3-Iodopropene (allyl iodide) 3-Iodopropionic acid 2-Iodotoluene 3-Iodotoluene 4-Iodotoluene Isatin Isobutylbenzene Isobutyl dichloracetate Isobutyl phenyl ketone Isobutyl trichloroacetate Isobutyronitrile L-Isoleucine Isopropenyl acetate Isopropyl radical Isopropyl acetate lsopropylbenzene (cumene) Isopropyl nitrate Isopropyl thiolacetate Isopropyl trichloroacetate Isoquinoline L-Isoserine Isothiocyanic acid Itaconic acid

c c g g liq

22.6 22.8 7.30 10.00 13.7

c liq liq liq c liq liq liq liq g c liq g liq liq g g liq liq c c g c

109.9 18.7 18.9 16.1 62.7 16.68 132.4 52.63 132.4 6.07 151.8 92.31 17.6 124.01 9.85 0.94 45.65 71.26 128.2 37.9 177.8 30.50 201.06

Ketene -Ketoglutaric acid

g c

14.60 245.35

D-Lactic acid

c c liq c

165.88 165.89 161.2 534.1

c

185.14

c c c c c c liq liq c

152.36 154.6 153.14 205.7 259.6 166.6 76.2 13.0 162.2

L-Lactic acid

-Lactose Lauric acid (dodecanoic acid) D-Leucine L-Leucine DL-Leucine DL-Leucylglycine Leucylglycylglycine Levulinic acid Levulinic lactone ()-Limonene DL-Lysine

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

6.68 4.80

80.32 77.55

21.48 21.53

24.76 82.97

74.88 49.71

23.04 45.00

29.70 32.74 9.72

66.87 92.87 89.20

36.26 28.84

26.98

59.28

11.09

14.41

57.79

12.37

124.98 123.84 374.52

34.3 34.00 45.9 92.3

82.97 82.76 83.54 112.14

49.71 50.62 49.5 67.2

48.03

5.26

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Maleic acid Maleic anhydride L-Malic acid DL-Malic acid Malonamide Malonic acid Malonic diamide Malononitrile Maltose L-Mandelic acid D-Mannitol D-Mannose Melamine (triaminotraizine) Melezitose 2-Mercaptopropionic acid Mesaconic acid Mesoxalic acid 2,2-Metacyclophane Methane Methanethiol (methyl mercaptan) Methanol Std state, m  1 L-Methionine Methoxyl radical 2-Methoxybenzaldehyde 3-Methoxybenzaldehyde 4-Methoxybenzaldehyde Methoxybenzene (anisole) Methoxymethyl radical 2-Methoxytetrahydropyran 5-Methoxytetrazole Methyl (CH3) radical Methyl acetate Methyl acrylate Methyl allantoin (pyvurile) Methyl allyl sulfone Methylamido radical (CH3NH) Methylamine Std state, m  1 Methylaminolithium N-Methylaniline

Hf , kcal · mol1

Gf , kcal · mol1

c c c c c c c c c c c c c

188.94 112.08 263.78 264.27 130.5 212.96 130.52 44.6 530.8 138.8 139.61 301.9 17.3

149.40

c liq c c g g g

815 111.9 197 290.7 40.8 17.89 5.49

liq g aq c g c liq liq g g liq c g liq g c liq g

57.13 48.06 58.78 180.4 (2) 63.7 66.0 63.9 17.3 (4) 105.7 16.6 34.82 106.4 70.10 177.0 91.95 35

g aq c liq

5.50 16.77 22.92 7.7

State

S , cal · deg1 · mol1 38.1

C p, cal · deg1 · mol1 32.36

211.45

412.60 225.20

57.0

44.10

35.63

82.19

54.70

12.15 2.37

44.52 60.96

8.54 12.01

39.87 38.82

30.41 57.29

19.40 10.49

120.88

55.32

35.35

46.38

9.25

57.98 29.5

11.97

56.78

7.71 4.94

5.27

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Methyl benzoate Methyl benzyl sulfone 2-Methylbiphenyl 3-Methylbiphenyl 4-Methylbiphenyl 2-Methyl-1,3-butadiene (isoprene) 3-Methyl-1,2-butadiene 2-Methylbutane 3-Methyl-1-butanethiol 2-Methyl-2-butanethiol 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol 3-Methyl-2-butanol 2-Methyl-1-butene 3-Methyl-1-butene 2-Methyl-2-butene Methyl butyl sulfone Methyl tert-butyl sulfone 3-Methyl-1-butyne Methyl caprate Methyl caproate (methyl hexanoate) N-Methylcaprolactam 5-Methylcaprolactam 7-Methylcaprolactam Methyl caprylate (methyl octanoate) Methyl chloride Methyl crotonate Methylcyclohexane 2-Methylcyclohexanol cis trans 3-Methylcyclohexanol cis trans 4-Methylcyclohexanol cis trans 2-Methylcyclohexanone Methylcyclopentane

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

liq c liq liq c g

79.8 88.65 25.8 20.4 13.2 18.10

34.86

75.44

25.00

g g g liq g liq liq liq g liq g g g liq c g liq liq

31.00 36.92 27.44 38.90 30.36 85.2 85.2 90.7 78.8 87.5 8.68 6.92 10.17 128.00 132.8 32.60 153.07 129.10

47.47 3.54

76.40 82.12

25.20 28.39

0.56 2.20

69.34 92.48

41.9 39.5

54.8 86.7

15.68 17.87 14.26

81.15 79.70 80.92

55.5 26.28 28.35 25.10

49.12

76.23

25.02

liq c c liq

73.3 86.9 86.5 141.07

g liq liq g

19.59 91.5 45.45 36.99

13.97

55.97

9.74

4.86 6.52

59.26 82.06

32.27

liq liq

93.3 99.4

liq liq

99.5 94.3

liq liq liq g

98.8 103.6 68.8 25.50

8.55

81.24

26.24

State

34.30 52.6 50.3 59.2

5.28

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 1-Methylcyclopentanol 2-Methylcyclopentanone 1-Methylcyclopentene 3-Methylcyclopentene 4-Methylcyclopentene Methyldichlorosilane 2-Methyl-1,3-dioxane 4-Methyl-1,3-dioxane N-Methyldiphenylamine 4-Methyldiphenylamine Methylene 2-Methylenecyclohexanol 2-Methylenecyclopentanol -Methylene--propiolactone (diketene) Methylene sulfate 1-Methyl-2-ethylbenzene 1-Methyl-3-ethylbenzene 1-Methyl-4-ethylbenzene 2-Methyl-3-ethylpentane 3-Methyl-3-ethylpentane 2-Methyl-3-ethyl-1pentene Methyl ethyl sulfite Methyl ethyl sulfone Methyl formate Methylglyoxal Methylglyoxime 2-Methylheptane 3-Methylheptane 4-Methylheptane Methyl heptanoate 2-Methylhexane 3-Methylhexane Methyl hexanoate 5-Methylhydantoin Methylhydrazine

State

Hf , kcal · mol1

liq liq g g g liq liq liq liq c g liq liq liq

82.3 63.4 1.30 2.07 3.53 105.9 104.60 99.80 28.8 11.7 92.35 66.3 11.2 55.72

c g g g liq g liq g g

164.6 0.29 0.46 0.78 59.69 50.48 60.46 51.28 23.97

liq c liq g g c liq g liq g liq g liq liq g liq g liq c liq g

135.55 116.17 90.60 83.70 64.8 30.3 60.98 51.50 60.34 50.82 60.17 50.69 135.54 54.93 46.59 54.35 45.96 129.11 116.3 12.9 22.55

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

24.41 27.48 29.06

78.00 79.00 78.60

24.10 23.90 23.90

88.25

46.32

8.27

31.33 30.22 30.28 3.03 5.08 2.69 4.76

95.42 96.60 95.34 81.41 105.43 79.97 103.48

37.74 36.38 36.22

71.53 71.03

29 72.00

0.92 3.05 1.12 3.28 1.87 4.00

84.16 108.81 85.66 110.32 83.72 108.35

0.69 0.77 0.39 1.10

77.28 100.38 78.23 101.37

53.28 39.67

43.0 44.66

39.66 66.61

32.25 17.0

15.90

39.67

5.29

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Methylidyne CH CH -Methylindole Methyl isocyanide 1-Methyl-2-isopropylbenzene (o-cymene) 1-Methyl-3-isopropylbenzene Methyl isopropyl ether Methyl isopropyl ketone Methyl isopropyl sulfone Methyl isothiocyanate (CH3NCS) 3-Methylisoxazole 5-Methylisoxazole Methyl laurate Methylmercury bromide Methylmercury chloride Methylmercury iodide Methyl myristate 1-Methylnaphthalene 2-Methylnaphthalene Methyl nitrate Methyl nitrite Methyl oleate Methyl pelargonate 2-Methylpentane 3-Methylpentane Methyl pentanoate 2-Methyl-1-pentene 3-Methyl-1-pentene 4-Methyl-1-pentene 2-Methyl-2-pentene 3-Methyl-2-pentene cis trans 4-Methyl-2-pentene cis trans Methyl pentanoate Methyl phenyl sulfone (2-Methyl phenol)

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g g c g liq

142.00 388.8 14.5 35.6 18.19

134.02 380.1

43.72 41.00

6.97 6.97

39.6

58.99

12.65

liq

18.69

g g liq g

60.24 62.76 120.44 31.3

28.89

80.86

26.55

34.5

69.29

15.65

liq liq liq c c c liq liq c liq g g liq liq g g liq g g g g

5.0 6.4 165.66 20.6 27.8 10.4 177.80 13.43 10.72 38.0 29.8 15.30 174.2 147.29 41.66 41.02 122.90 12.49 10.76 10.54 14.28

46.26 46.03 10.4 9.4 0.24

60.90 52.58 51.9 76.1 67.95

53.63 46.84 37.6

1.20 0.51

90.95 90.77

34.46 34.20

18.55 20.66 21.52 17.02

91.34 90.06 87.89 90.45

32.41 34.04 30.23 30.26

g g

13.80 14.02

17.50 17.04

90.45 91.26

30.26 30.26

g g liq c g

12.03 12.99 122.89 82.49 30.74

19.63 19.03

89.23 88.02

31.92 33.80

8.86

85.47

31.15

State

15.11

5.30

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance (3-Methyl phenol) (4-Methyl phenol) Methylphosphonic acid 2-Methylpropanal 2-Methylpropane 2-Methyl1,2-propanediamine 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol 2-Methyl-1-propanol 2-Methyl-2-propanol 2-Methylpropene Methyl propyl ether 7-Methylpurine 2-Methylpyridine (2-picoline) 3-Methylpyridine 4-Methylpyridine N-Methylpyrrolidone Methyl salicylate -Methylstyrene -Methylstyrene cis trans Methylsuccinic acid 3-Methyl-2-thiabutane 2-Methylthiacyclopentane 2-Methyl-3-thiapentane 4-Methylthiazole 2-Methylthiophene 3-Methylthiophene 4-Methyluracil Methyl valerate (methyl pentanoate) Morphine monohydrate Mucic acid Murexide Myrcene Myristic acid (tetradecanoic acid) Naphthalene 1-Naphthol

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g g c g g liq

31.63 29.97 252 52.25 32.15 32.00

9.69 7.38

85.27 83.09

29.27 29.75

4.99

70.42

23.14

g g g liq g g g c liq

23.24 26.17 67.69 85.86 74.67 4.04 56.82 51.3 13.83

1.33 0.17 39.99 44.14 42.46 13.88 26.27

86.73 80.79 85.81 46.10 77.98 70.17 83.52

28.28 28.91 26.6 52.61 27.10 21.30 26.89

39.80

52.07

37.86

g liq liq liq liq liq g

24.05 15.57 13.58 62.64 127.1 16.8 27.00

42.32 41.16

77.68 51.70

23.90 37.93

49.84

91.70

34.70

g g c g g liq liq liq liq c liq

29.00 28.00 229.02 21.61 15.12 37.3 16.31 10.75 10.38 109.2 122.89

51.84 51.08

91.70 90.90

34.70 34.90

3.21

85.87

28.00

27.35 27.00

52.22 52.19

29.43 29.38

c c c liq c

170.1 423 289.7 3.5 199.21

c g g

18.0 35.6 5.1

48.05 53.44

39.89 80.22

31.68

State

5.31

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 2-Naphthol 1,4-Naphthoquinone 1-Naphthyl acetate 2-Naphthyl acetate 1-Naphthylamine 2-Naphthylamine Narceine dihydrate Narcotine Nicotine Nitrilotriacetic acid 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline Nitrobenzene 2-Nitrobenzoic acid 3-Nitrobenzoic acid 4-Nitrobenzoic acid 3-Nitrobiphenyl 4-Nitrobiphenyl 1-Nitrobutane 2-Nitrobutane 3-Nitro-2-butanol 2-Nitrodiphenylamine Nitroethane aci form nitro form 2-Nitroethanol Nitroguanidine Nitromethane

State

Hf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

10.1 43.83 68.89 72.72 16.2 14.4 421.2 210.9 9.4

1-Nonanethiol Nonanoic acid 1-Nonanol 1-Nonene

g c c c c c c c liq c c c c liq c c c c c g g liq c g aq aq liq c liq g c g g c g g g liq g g liq liq g

3.45 4.46 9.91 3.80 94.25 100.25 101.25 15.6 9.7 34.40 39.10 93.2 15.4 24.4 30.7 32 83.8 22.1 27.03 17.86 10.2 30.00 33.21 50.9 104.00 74.00 74.16 65.84 54.74 45.61 157.68 109.2 24.74

Octadecane Octadecanoic acid

g c

99.08 226.5

1-Nitronaphthalene 1-Nitropropane 2-Nitropropane 4-Nitrosodiphenylamine Nonadecane 1-Nonadecene 1-Nonanal Nonane

Gf , kcal · mol1

312.5 42.60 41.60 36.10 34.95 46.95 52.71 53.07

42.1 42.1 42.1 53.6 49.8 49.0 50.2

39.3 40.2 40.4 44.4

2.42 1.49

94.28 91.62

29.85 29.51

1.17

75.39

18.69

3.47 1.66

41.05 65.73

25.33 13.70

0.08 3.06

85.00 83.10

24.41 24.26

26.03 47.02 17.91 2.81 5.93 12.67

213.95 212.95 128.97 94.09 120.86 136.51

105.26 102.69 51.82

32.4 26.93

91.3 119.86

67.50 48.03

24.02

204.64

99.80

43.3

50.60 55.61

5.32

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 1-Octadecene Octafluorocyclobutane 1-Octanal Octanamide Octane 1-Octanethiol Octanoic acid (caprylic acid) 1-Octanol 2-Octanone 1-Octene 1-Octyne Oleic acid DL-Ornithine Oxacyclobutane (trimethylene oxide) Oxalic acid Std state, m  1 Oxalic acid dihydrate Oxalyl chloride Oxamic acid Oxamide Oxindole 8-Oxypurine Palmitic acid (hexadecanoic acid) Papaverine Parabanic acid [1,8]-Paracyclophane [2,2]-Paracyclophane [6,6]-Paracyclophane Paraldehyde Pentachloroethane Pentachlorofluoroethane Pentachlorophenol Pentadecane 1-Pentadecene 1-Pentadecyne 1,2-Pentadiene 1,3-Pentadiene cis trans 1,4-Pentadiene

Hf , kcal · mol1

Gf , kcal · mol1

S , cal · deg1 · mol1

g g g c liq g g liq

69.08 365.20 69.23 113.1 59.74 49.82 40.68 151.93

45.01 334.33 19.91

203.64 95.69 119.66

97.22 37.32 46.36

1.77 3.92 10.67

85.50 111.55 127.20

45.14 45.14 50.14

liq liq liq g g c c g

101.6 91.9 29.52 19.82 19.70 187.2 156.0 19.25

34.2 33.54 22.49 24.91 56.26

90.2 89.35 86.15 110.55 106.75

77.7 65.31 57.65 42.56 41.58

2.33

65.46

c aq c liq c c c c

197.7 197.2 341.0 85.6 160.4 123.0 41.2 15.4

166.8 161.1

28.7 10.9

81.9

28.2

c

213.10

c c c g c liq g g c g g g g

120.2 138.0 19.6 59.9 46.1 164.2 34.8 75.8 70.6 84.31 54.31 14.78 34.80

16.79 55.93 34.44 17.98 38.97 70.25 50.29

91.17 93.54 60.21 176.71 175.71 171.91 79.70

28.22

g g g

18.70 18.60 25.20

34.84 35.07 40.69

77.50 76.40 79.70

22.60 24.70 25.10

State

C p, cal · deg1 · mol1

48.27 83.40 80.82 79.84 25.20

5.33

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 2,3-Pentadiene Pentaerythritol Pentaerythritol tetranitrate Pentafluorobenzoic acid Pentafluoroethane Pentafluorophenol Pentamethylbenzene Pentamethylbenzoic acid 1-Pentanal Pentanamide Pentan-2,4-dione (acetylacetone) Pentan-1,5-dithiol Pentane 1-Pentanethiol Pentanoic acid (valeric acid) 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone 3-Pentanone 1-Pentene 2-Pentene cis trans 2-Pentenoic acid 3-Pentenoic acid 4-Pentenoic acid 1-Pentyne 2-Pentyne Perfluoropiperidine Perylene -Phellandrene Phenacetin 9,10-Phenanthraquinone Phenanthrene Phenazine Phenol

Phenoxy radical Phenoxyacetic acid Phenyl radical Phenyl acetate

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g c c c g c liq c g c liq g liq g liq liq

33.10 220.0 128.8 296.34 264.00 244.86 32.33 128.13 54.45 90.70 101.33 90.47 30.99 35.00 35.72 133.71

49.21 146.73

77.60 47.34

24.20 45.51

246.00

79.76

22.88

25.64

70.22

51.74

25.88

91.53

29.96

95.1

28.7

2.00 2.28 89.10

83.40 74.18 62.10

28.73

liq liq liq g liq g

85.0 87.7 88.5 61.82 70.87 5.00

38.3

62.0

49.8

40.4 32.76

57.4 89.91

60.0 28.91

18.91

82.65

26.19

g g liq liq liq g g liq c liq c c c c c liq g g c g liq

6.71 7.59 106.7 103.9 102.9 34.50 30.80 482.9 43.69 14.3 101.1 55.18 27.3 56.4 39.44 37.80 23.03 10 122.8 71 80.02

17.17 16.71

82.76 81.36

24.32 25.92

50.25 46.41 422.67

78.82 79.30 94.02

25.50 23.59 70.93

64.12

50.6

12.05 11.02 7.86

34.42

State

75.43

50.48

32.2 30.46 24.75

5.34

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Phenylacetic acid Phenylacetylene -Phenyl-1-alanine, DL- and LPhenyl benzoate 2-Phenylbenzoic acid Phenylboronic acid 1-Phenylcyclohexene Phenylcyclopropane N-Phenyldiacetimide p-Phenylenediamine Phenyl ethyl sulfide DL-Phenylglyceric acid N-Phenylglycine a-Phenylglycine Phenylglyoxime   Phenylglyoxylic acid Phenylhydrazine Phenyl methyl sulfide N-Phenyl-2-naphthylamine N-Phenylpyrrole 2-Phenylpyrrole Phenyl salicylate Phenyl thiolacetate Phosgene Phthalamide m-Phthalic acid o-Phthalic acid p-Phthalic acid Phthalic anhydride Phthalonitrile Pimelic acid (heptanedioic acid) Pinene   Piperazine Piperidine -Piperidone DL-Proline Propadiene Propane 1,2-Propanediamine

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

c g c

95.3 78.22 111.9

86.46 50.6

76.88 51.06

27.46 48.52

c c c liq liq c c liq c c c

57.7 83.4 172.0 4.0 24.7 86.63 0.73 5.29 178.5 96.2 103.2

c c c liq liq c c c c liq g c c c c c c c

4.9 10.1 115.3 34.03 11.5 38.2 38.1 34.5 104.3 29.16 52.80 104.4 191.91 186.91 195.05 110.1 65.82 241.25

49.42

67.82

13.79

141.39

49.7

45.0

79.12

42.9

38.5

liq liq c liq c c g g liq

3.9 1.8 10.90 21.05 73.3 125.7 45.92 24.82 23.38

26.79

39.4

48.37 5.63

58.30 64.58

State

14.10 17.59

5.35

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 1,2-Propanediol 1,3-Propanediol 1,3-Propanedithiol 2,3-Propanedithiol 1-Propanethiol 2-Propanethiol 1-Propanol 2-Propanol 1,2,3-Propenetricarboxylic acid cis trans 2-Propen-1-ol (allyl alcohol) Propionaldehyde Propionamide Propionic acid Propionic anhydride Propionitrile 1-Propylamine 2-Propylamine Propylbenzene Propylcarbamate Propyl chloroacetate Propylcyclohexane Propylcyclopentane Propylene (propene) Propylene oxide Propyl nitrate Propyl phenyl ketone Propyl thiolacetate Propyl trichloroacetate Propyne (methyl acetylene) Pyrazine Pyrazole Pyrene Pyridazine Pyridine Pyrimidine Pyrrole

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

liq liq liq liq g g liq g liq g

119.6 124.4 18.83 18.82 16.22 18.22 72.66 61.28 75.97 65.11

0.52 0.61 40.78 38.67 43.09 41.44

80.40 77.51 46.5 77.61 43.16 74.07

22.65 22.94 33.7 20.82 36.06 21.21

c c g

292.7 294.7 31.55

17.03

73.51

18.17

g c liq liq liq g g liq g c liq g g g g g liq liq liq g

45.90 81.7 122.07 161.53 3.5 12.10 17.30 26.83 1.87 132.07 123.3 46.20 35.39 4.88 22.17 41.60 45.14 70.29 122.7 44.32

31.18

72.83

18.80

91.65 113.66 21.31 22.98 9.51

45.25 68.50 77.48

17.46 22.89

32.80

95.76

36.41

11.31 12.57 15.02 6.16 6.53

100.27 99.73 63.72 68.53 92.10

44.03 36.96 15.37 17.29 28.99

46.47

59.30

14.50

c c c liq liq g liq liq

33.41 28.3 27.44 53.74 23.96 33.61 35.04 15.08

64.40

53.75

56.4

43.34 45.46

42.52 67.59

31.72 18.67

State

5.36

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued ) S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

24.8 2.9 9.84 0.86 68.3 139.7

25.94 27.41

48.76 73.97

2-Pyrrolidone Pyruvic acid

c c liq g c liq

110.75

42.9

Quinaldine Quinhydrone Quinidine Quinine Quinoline p-Quinone

c c c c liq c

39.3 19.79 38.3 37.1 37.33 44.10

77.19

77.9

65.90 20.0

51.9 38.9

Raffinose

c c c c

761 256.5 455.4 251.16

c liq c c c c

249.6 66.9 43.91 140.9 121.2 258.8

99.93

42.6

aq

39.9

9.7

71.2

c c c c c g c

173.6 281.8 93.4 303.68 167.8 44.27 226.5

217.10

52.8

63.41

67.45

liq c c liq g c

43.81 32.27 41.0 24.83 35.22 248.1

75.90

60.0

48.37 51.10

56.78 82.48

43.64 29.18

c c c

138.9 224.79 2531.9

178.64 2369.18

42.0 86.1

35.8

Substance Pyrrole-2-aldehyde Pyrrole-2-aldoxime Pyrrolidine

L-Rhamnose

Rhamnose triacetate D-Ribose

Saccharinic acid lactone Salicylaldehyde Salicylaldoxime Salicyclic acid Sarcosine Sebacic acid (decanedioic acid) Semicarbazide, std state, m1 L-Serine Serylserine Sorbic acid L-Sorbose 5,5-Spirobis(1,3-dioxane) Spiropentane Stearic acid (octadecanoic acid) Stilbene cis trans Strychnine Styrene Suberic acid (octanedioic acid) Succinamide Succinic acid Sucrose

State

19.39

66.2

21.06

5.37

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance L-Tartaric acid DL-Tartaric acid

meso-Tartaric acid Tetrabromomethane Tetracene Tetrachlorobenzoquinone 1,1,1,2-Tetrachlorodifluoroethane 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrachloromethane 1,1,2,2-Tetracyanocyclopropane Tetracyanoethylene Tetradecane Tetradecanoic acid 1-Tetradecene Tetraethylene glycol Tetraethyllead 1,1,1,2-Tetrafluoroethane Tetrafluoroethylene Tetrafluoromethane Tetrahydrofuran Tetrahydrofurfuryl alcohol 1,2,3,4-Tetrahydronaphthalene (Tetralin) Tetrahydropyran 1,2,5,6-Tetrahydropyridine Tetraiodomethane 1,2,3,4-Tetramethylbenzene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane Tetramethyllead Tetramethylsilane Tetramethylsuccinic acid Tetramethylthiacyclopropane Tetranitromethane 1,1,1,2-Tetraphenylethane

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

c c c g c c g

306.5 308.5 305.9 19.00 37.95 69.0 117.1

15.61

85.53

21.78

97.3

91.5

29.5

g liq g g liq g c

35.7 47.0 36.50 3.40 31.75 22.90 141

19.2 22.7 20.45 4.90 14.97 12.80

85.05 59.0 86.69 81.46 51.67 74.07

24.67 39.6 24.09 22.69

c g c g liq liq g g g g liq liq liq

149.1 79.38 199.2 49.36 234.6 12.7 26.3 214.10 157.40 223.0 51.67 104.1 6.1

15.97

167.40

77.93

36.99

166.40

75.36

80.4

112.92

197.46 149.07 212.3

75.58 71.69 62.45

20.62 19.24 14.59

liq liq g liq liq liq g liq g g c c

61.1 8.0 62.84 23.0 23.54 29.48 53.99 23.5 32.6 68.50 242.0 19.84

51.89 25.49 23.58 24.20 5.26 62.8 64.7 23.92

93.60 69.45 99.55 71.83 93.06 76.5 100.5 86.30

22.91

liq c

8.9 53.31

State

19.94

57.5 51.6

34.42 31.12

5.38

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

State

Hf , kcal · mol1

1,1,2,2-Tetraphenylethane Tetraphenylethene Tetraphenylhydrazine Tetraphenylmethane Tetrazole Thebaine Theobromine Thiaadamantane 2-Thiabutane

c c c c c c c c liq g g g liq g liq g liq g liq

51.63 74.46 109.4 59.1 56.7 63.0 86.4 34.22 21.89 14.25 14.61 14.66 25.32 15.12 17.39 8.08 12.41 19.65 21.68

g g liq g liq g liq g liq g liq g liq g g liq g c c liq liq liq g c c aq, 100

29.34 29.92 40.62 29.96 34.15 24.42 34.58 25.00 52.74 39.99 28.21 19.54 28.43 19.95 8.97 63.61 43.49 132.6 59.5 52.39 111.6 19.24 27.66 6.0 21.13 15.6

Thiacyclobutane Thiacycloheptane Thiacyclohexane Thiacyclopentane Thiacyclopropane 4-Thia-5,5-dimethylhex1-ene 2-Thiaheptane 3-Thiaheptane 4-Thiaheptane 2-Thiahexane 3-Thiahexane 5-Thianonane 2-Thiapentane 3-Thiapentane 2-Thiapropane 6-Thiaundecane Thioacetic acid Thiohydantoic acid Thiohydantoin Thiolacetic acid -Thiolactic acid Thiophene Thiosemicarbazide Thiourea

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

137.20

1.79 2.73 25.69 20.09 9.96 12.68 8.97 11.00 22.52 23.16

57.14 79.62 68.17 86.50 52.16 77.26 49.67 73.94 38.84 61.01

8.39 7.65 5.12 7.94 4.08 6.37 3.50 5.63 7.66 11.76 2.79 4.40 2.81 4.25 1.66

107.73 108.27 80.85 107.16 73.49 98.43 73.98 98.97 96.82 125.76 65.14 88.84 64.36 87.96 68.32

39.10 38.71

36.81

74.86

19.33

28.97 30.30

43.30 66.65

17.42

5.2

27.7

22.73 16.57 29.78 25.86 21.72 12.83

38.53 33.64 33.25 49.46 28.05 40.97 27.97 17.71

5.39

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Threonine, L- and DLThymine Thymol Tiglic acid Toluene 2-Toluenethiol m-Toluic acid o-Toluic acid p-Toluic acid o-Toluic anhydride p-Toluic anhyride Trehalose 2,4,6-Triamino1,3,5-triazine (triaminotriazine) 2-Triazoethanol Tribenzylamine Tribromochloromethane Tribromofluoromethane Tribromomethane Tributylamine Tributyl borate Tributylboron Tributyl phosphate Tributylphosphine oxide Trichloroacetaldehyde Trichloroacetamide Trichloroacetic acid Ionized Trichloroacetyl chloride Trichlorobenzoquinone 1,1,1-Trichloroethane 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichloromethyl 1,2,3-Trichloropropane 1,1,1-Tricyanoethane Tricyanoethylene Tridecane Tridecanoic acid 1-Tridecene Triethylaluminum

State

Hf , kcal · mol1

c c c c liq g liq c c c c c c c g

181.4 111.9 74.0 117.3 2.87 11.95 10.57 101.85 99.55 102.59 127.5 124.5 531.3 17.3 17.13

liq c g g g liq liq liq liq c liq c c aq liq c g g g g g g c c g c g liq

22.6 33.6 3.0 45.4 4.00 67.32 286.7 83.4 348 110 56.1 85.6 120.7 123.4 66.4 64.5 34.01 33.10 1.40 68.10 19 44.40 83.9 105.0 74.45 192.8 44.45 56.6

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

27.19 29.16

52.81 76.64

37.58 24.77

44.10 42.33

35.63 74.10

20.93

2.17 46.14 1.78

85.36 82.65 79.01

16.96

18.21 18.52 4.75 58.68 22 23.37

76.49 80.57 77.63 74.06 70.9 91.52

22.07 21.47 19.17 18.66 15.21 26.82

13.97

158.09

72.47

34.96

157.09

69.89

5.40

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance Triethylamine Triethylaminoborane Triethyl arsenite Triethylarsine Triethyl borate Triethylenediamine Triethylene glycol Triethyl phosphate Triethylphosphine Triethyl phosphite Triethylstibine Triethylsuccinic acid Triethyl thionophosphate Trifluoroacetic acid Trifluoroacetonitrile 1,1,1-Trifluoroethane 2,2,2-Trifluoroethanol Trifluoroethylene Trifluoroiodomethane Trifluoromethane Trifluoromethyl CF3 · CF3 Trifluoromethylbenzene Trifluoromethylhypofluorite (CF3OF) DL-Trihydroxyglutaric acid Triiodomethane Trimethylacetic acid Trimethylacetic anhydride 2,4,5-Trimethylacetophenone 2,4,6-Trimethylacetophenone Trimethylaluminum Trimethylamine Std state, molarity  1 Trimethylamine aluminum chloride adduct Trimethylammonium ion Std state, molarity  1 Trimethyl arsenite Trimethylarsine

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

g liq liq liq liq c liq liq liq liq liq c liq liq g g liq g g g

23.80 47.47 168.9 3.1 250.4 3.4 192.2 297 21.3 205.9 1.2 254.9 232.5 255.4 118.4 178.20 207.4 118.50 141.0 165.71

26.36

96.90

57.28

37.67

110.4 162.11

71.3 68.67

18.70 18.76

112.22 136.70 157.48

69.94 73.50 62.04

16.54

g g liq g g

112.4 100.6 152.40 143.42 183

109.2 103.1 123.98 122.20 169

63.3 60.8 64.89 89.05 77.06

11.90 11.87

c

356

g liq liq liq

50.40 134.9 186.4 60.3

42.54

84.97

17.94

liq

63.9

liq g aq c

36.1 5.70 18.17 210.1

23.64 22.22

50.05 69.02 31.9

37.19 21.93

aq

26.99

8.90

47.0

liq liq

141.2 3.9

State

38.46

12.22

31.17 18.97

5.41

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 1,2.3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Trimethyl borate Trimethylboron 2,2,3-Trimethylbutane Trimethylchlorosilane cis,cis-1,3,5-Trimethylcyclohexane 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane 2,3,4-Trimethylpentane 2,4,4-Trimethyl-1-pentene 2,4,4-Trimethyl-2-pentene Trimethylphosphine TrimethylphosphineN-ethylimine Trimethylphosphine oxide Trimethyl phosphite Trimethylsilanol Trimethylstibine Trimethylsuccinic acid Trimethylsuccinic anhydride Trimethylthiacyclopropane Trimethylurea 2,4,6-Trinitroanisole 1,3,5-Trinitrobenzene Trinitromethane 1,4,5-Trinitronaphthalene 1,3,8-Trinitronaphthalene 2,4,6-Trinitrophenetole 2,4,6-Trinitrophenol 2,4,6-Trinitrophenylhydrazine 2,4,6-Trinitrotoluene 2,4,6-Trinitro-m-xylene Triphenylamine Triphenylarsine Triphenylcarbinol

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1

liq liq liq liq liq g liq g

14.01 14.79 15.18 222.9 34.1 48.95 91.8 51.48

25.68 24.46 24.83

66.40 67.93 65.38

1.02

91.61

39.33

8.10

93.30

42.93

liq g liq g liq g liq g liq liq liq liq

61.44 52.61 61.97 53.57 60.63 51.73 60.98 51.97 35.21 34.44 29.2 35.8

2.21 4.09 1.65 3.27 2.54 4.52 2.55 4.52 20.66 21.04

78.30 101.62 78.40 101.15 79.93 103.14 78.71 102.31 73.2 74.5

c liq liq liq c c

114.2 177.1 130.3 0.2 239.2 164.5

liq c c c c c c c c c

14.47 79.0 37.6 10.40 11.50 8.7 5.8 48.9 51.23 8.8

c c c c c

16.0 24.5 58.7018 C 74.1 0.80

State

120.50 65.2

78.7

5.42

SECTION 5

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance

State

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

Hf , kcal · mol1

Gf , kcal · mol1 78.68

60.87

123.00 98.60

74.6

70.5

28.54 92.18

60.00 51.15

56.92 51.73 61.53 58.96 22.26

Triphenylene 1,1,1-Triphenylethane 1,1,2-Triphenylethane Triphenylethylene Triphenylmethane Triphenyl phosphate Triphenylphosphine Triphenylphosphine oxide Tripropylamine Tris(acetylacetonato)chromium 1,1,1-Tris(hydroxymethyl)ethane Tropolone L-Tryptophan L-Tyrosine

c c c c c c c c liq c

33.72 37.56 31.11 55.8 38.71 181 55.5 14.4 49.51 366.4

c

177.96

c c c

57.18 99.8 163.4

Undecane 1-Undecene Urea Std state, m  1 Urea nitrate Urea oxalate Uric acid

liq g g c aq c c c

78.05 64.60 34.60 79.71 75.95 134.8 365.3 147.73

5.44 9.94 30.94 47.19

109.49 139.48 138.48 25.00

85.75

41.4

Valeric acid Valine, L and DLValylphenylalanine Veronal Vinyl radical Vinyl bromide Vinyl chloride Vinylcyclohexane Vinylcyclopropane 2-Vinylpyridine

liq c c c g g g liq liq liq

133.71 148.2 183.5 178.7 63 18.7 8.5 21.19 29.3 37.2

89.10 85.80

62.10 42.75

50.48 40.35

19.3 12.4

65.90 63.07

13.27 12.84

Xanthine o-Xylene

c liq g liq g liq g g g g

90.49 5.84 4.54 6.08 4.12 5.84 4.29 37.57 38.93 38.63

39.64 26.37 29.18 25.73 28.41 26.31 28.95

38.5 58.91 84.31 60.27 85.49 59.12 84.23

m-Xylene p-Xylene 2,3-Xylenol 2,4-Xylenol 2,5-Xylenol

44.9 31.85 43.8 30.49 30.32

5.43

THERMODYNAMIC PROPERTIES

TABLE 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds (continued )

Substance 2,6-Xylenol 3,4-Xylenol 3,5-Xylenol Xylitol D-Xylose

State g g g c c

Hf , kcal · mol1 38.66 37.42 38.61 267.32 252.8

Gf , kcal · mol1

S , cal · deg1 · mol1

C p, cal · deg1 · mol1

5.44

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds Abbreviations Used in the Table Hm, enthalpy of melting (at the melting point) in kcal · mol1 Hv, enthalpy of vaporization (at the boiling point) in kcal · mol1 Hs, enthalpy of sublimation (at 298 K) in kcal · mol1 Cp, specific heat (at temperature specified, measured on the Kelvin scale) for physical state in existence at that temperature, expressed in cal · K1 · mol1 Ht, enthalpy of transition (at temperature specified, measured in degrees Celsius) in kcal · mol1 Cp Substance Acenaphthene Acenaphthylene Acetaldehyde Acetanilide Acetic acid Acetic anhydride Acetone Acetonitrile (Ht, 0.215 at 56 C) Acetophenone Acetyl bromide Acetyl chloride Acetylene Acetylenedicarbonitrile Acetyl fluoride Acetyl iodide Acrylic acid Acrylonitrile Adenine

Hm

Hv

Hs

400 K

600 K

800 K

1000 K

15.73

20.52

24.20

29.96

19.52 30.86 22.00 14.62

25.15 41.62 29.34 18.35

29.08 48.91 34.93 21.26

31.99 54.11 39.15 23.50

18.86 11.97 22.66

23.18 13.73 25.37

26.30 14.93 27.26

28.60 15.92 28.62

22.94 18.36

29.50 23.11

33.93 26.43

37.12 28.88

20.6 17.0 0.770

6.24 19.3

2.80 2.51 1.366 1.952

5.663 9.85 6.952 7.3 9.275

0.900

4.05

11.21 7.8

11.54 7.94 13.4 7.9 7.2 5.1 6.88 6.0 7.9 12.98 25.8

Adipic acid -Alanine Allyl ethyl sulfoxide Allyl trichloroacetate 1-Aminobutane 2-Aminobutane Aniline Anthracene 9,10-Anthracenedione Azoisopropane Azulene

5.45

Benzaldehyde 1,2-Benzanthra-9,10-quinone Benzene Benzenethiol Benzil Benzoic acid Benzoic anhydride Benzonitrile Benzophenone 1,4-Benzoquinone Benzoyl bromide Benzoyl chloride Benzoyl iodide 3,4-Benzophenanthrene Benzyl bromide Benzyl chloride Benzyl ethyl sulfide Benzyl iodide Benzyl methyl ketone Benzyl methyl sulfide Bicyclo[4.1.0]heptane Bicyclo[3.1.0]hexane

2.519

10.643 13.5

2.89

13.26

2.358 2.736

7.352 9.53

4.32

12.10

2.60

11.0

30.8 33.0 17.1 12.5 8.50 7.5 13.325 24.7 26.8 8.5 22.8 12 19.8 8.090 11.64 23.5 22.70 23 13.26 22.5 15.00 14.0 13.1 14.8 25.4 11.3 12.3 13.6 11.3 12.78 12.8 9.14 7.85

35.44 35.40 34.17

47.30 47.55 46.09

56.01 56.42 53.79

62.54 62.54 69.18

42.15

59.32

70.59

78.24

26.74 32.76

37.73 44.13

45.06 51.59

50.16 56.79

33.65

44.80

52.08

57.08

5.46

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance Bicyclo[4.2.0]octane Bicyclo[5.1.0]octane Bicyclopropyl Biphenyl Biphenylene Bromobenzene 4-Bromobenzoic acid 1-Bromobutane 2-Bromobutane Bromoethane Bromoethene 1-Bromoheptane 1-Bromohexane Bromomethane Ht, 0.113 at 99.4 C 2-Bromo-2-methylpropane Ht, 1.35 at 64.5 C; 0.25 at 41.6 C 1-Bromooctane 1-Bromopentane 1-Bromopropane 2-Bromopropane 1,2-Butadiene 1,3-Butadiene n-Butadiene sulfone Butadiyne Butane Ht, 0.494 at 165.60 C 2,3-Butanedione 1,4-Butanedithiol 1-Butanethiol

Hm

Hv

Hs

400 K

600 K

800 K

1000 K

9.85 10.42 8.0 4.44

10.9

2.54

9.05

1.6

7.78

1.4

6.41

52.83

73.54

86.92

96.00

30.8 10.62 21.0

30.44

40.99

47.78

52.40

8.45 6.57

32.64 33.09 18.93 15.91

43.00 43.76 24.56 19.83

50.48 51.31 28.58 22.50

56.03 56.93 31.59 24.46

11.94 34.93

14.98 45.58

17.26 52.65

19.01 57.74

39.58 25.70 26.34 23.54 24.29

52.34 33.66 34.42 30.72 31.84

61.55 39.41 40.09 36.01 36.84

68.36 43.70 44.26 40.02 40.52

20.17 29.60

23.14 40.30

25.11 48.23

26.61 54.22

34.95

46.54

55.68

62.95

12.05 10.91 1.429 0.47

5.715

2.74 1.56 1.665 1.908

8.24 7.14 6.79 5.82 5.42

1.114

5.352

2.500

7.702

7.4 13.14

5.71 5.03 14.7 5.035 9.25 13.22 8.73

5.47

2-Butanethiol 1-Butanol 2-Butanol 2-Butanone 1-Butene 2-Butene cis trans 1-Buten-3-yne N-Butylacetamide Butyl acetate tert-Butylamine Butylbenzene stable(I) metastable(II) sec-Butylbenzene tert-Butylbenzene sec-Butyl butyrate Butyl chloroacetate Butyl 2-chlorobutyrate Butyl 3-chlorobutyrate Butyl 4-chlorobutyrate Butyl 2-chloropropionate Butyl 3-chloropropionate Butyl crotonate sec-Butyl crotonate Butylcyclohexane Butylcyclopentane N- Butyldiacetimide Butyl dichloroacetate tert- Butyl hydroperoxide Butylisobutylamine Butyl lithium Butyl trichloroacetate

1.548 2.24 2.017 0.920 1.747 2.332

7.312 10.31 9.75 7.475 5.238

5.580 5.439

8.58 2.682(I) 2.691(11)

3.384 2.704

8.14 12.52 11.87 8.34 4.81

35.38 32.80 33.70 29.81 26.04

46.42 43.90 44.72 39.09 35.14

54.29 52.11 52.68 46.08 41.80

60.02 58.26 58.62 51.33 46.82

5.29 5.10

24.33 26.02 21.26

33.80 34.80 26.67

40.87 44.20 30.40

46.15 46.58 33.16

18.2 10.42 7.10

36.46

48.87

57.49

63.79

11.98

54.75

75.20

89.37

99.49

66.00 57.77

93.10 80.38

112.30 97.35

125.70 114.80

9.38

9.20 8.69

11.72 11.50 11.3 12.2 12.6 12.7 13.0 13.0 13.3 12.4 11.8 11.96 11.00 15.4 12.5 11.41 10.73 25.6 12.8

5.48

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance

Hm

1-Butyne 2-Butyne Butyraldehyde Butyric acid Butyronitrile

1.441 2.207 2.654 2.50 1.2

D-Camphor

1.635

-Caprolactam Carbazole Carbon disulfide Chloroacetic acid Chloroacetyl chloride 2-Chlorobenzaldehyde Chlorobenzene 2-Chlorobenzoic acid 3-Chlorobenzoic acid 4-Chlorobenzoic acid Chlorobenzoquinone 1-Chlorobutane 2-Chlorobutane Chlorocyclohexane Chlorodifluoromethane Chloroethane 1-Chloro-2-ethylbenzene 1-Chloro-4-ethylbenzene Chloroethylene Chloroethyne Chlorofluoromethane

1.049

2.28

Hv

5.861 6.340 10.04 8.13 14.22

400 K

600 K

800 K

1000 K

5.67 6.38 8.05 15.2 9.53

23.87 22.62 30.20

30.83 29.68 39.60

35.95 35.14 46.60

39.84 39.29 51.70

28.39

37.07

43.48

48.22

30.62

41.16

47.89

52.48

32.30 32.52

42.77 43.18

50.31 50.84

55.92 56.60

15.63 18.54

18.87 24.28

20.84 28.39

22.10 31.48

15.56 14.39 13.29

19.61 15.97 16.57

22.35 16.98 18.81

24.35 17.75 20.39

19.9 20.2

6.401

8.73

7.38 6.98 0.985 1.064

Hs

18 9.3 13.3 9.81 19.0 19.6 21.0 16.5 8.0 7.60 10.4

4.833 5.892 11.3 11.5

5.49

Chloroform Chloromethane Chloromethyloxirane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane Ht, 0.41 at 90.1 C; 1.39 at 53.6 C 1-Chloronaphthalene 2-Chloronaphthalene 1-Chloropentane 3-Chlorophenol 4-Chlorophenol 1-Chloropropane 2-Chloropropane 3-Chloro-1-propene Chlorotrifluoromethane Chlorotrinitromethane Chrysene o-Cresol m-Cresol p-Cresol m-Cresyl acetate Cubane 4-Cyanothiazole Cyclobutane Ht, 1.38 at 126.79 C Cyclobutene Cyclododecane Cycloheptane Ht, 1.187 at 138.4 C; 0.069 at 75.0 C; 0.108 at 60.8 C Cycloheptanone 1,3,5-Cycloheptatriene Ht, 0.561 at 118.19 C Cyclohexane Ht, 1.611 at 87 C Cyclohexanol Ht, 1.96 at 9.7 C Cyclohexanone Cyclohexene Ht, 1.016 at 134.4 C

2.28 1.537

7.08 5.147

7.48 9.7 7.57

0.48

6.6

7.93

6.62 6.34

15.6 19.6 9.1 12.7 12.4 6.9 6.47

0.260

5.781

10.86 28.1 18.17 14.75 17.67 14.51 19.2 17.67 5.65

0.450

7.93

18.26 9.21

0.277

9.250

0.640 0.406

7.160 10.875 9.00 7.285

10.20 10.32 10.32

17.75 11.52

20.38 14.66

21.87 17.04

22.83 18.86

32.52 34.00

43.18 44.20

50.84 51.50

56.60 57.00

39.24

52.11

61.38

68.25

25.36 25.99 22.12 18.53

33.43 34.20 28.43 21.60

39.24 39.94 32.93 23.17

43.59 44.16 36.30 24.03

39.74 38.74 38.65

52.77 52.26 52.10

61.55 61.27 61.11

68.82 68.50 68.48

23.89 21.59

34.76 30.30

42.42 36.26

47.96 40.53

41.82

62.42

77.03

87.40

37.13

50.07

58.58

64.58

35.82 41.14 36.00 34.64

53.83 59.29 52.90 49.45

66.76 72.18 65.00 59.49

75.80 81.13 73.00 66.62

12.4

0.787

7.896 12.820 10.77 8.00

5.50

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance

Hm

Hv

Hs

400 K

600 K

800 K

1000 K

Cyclooctane Ht, 1.507 at 106.7 C; 0.114 at 89.35 C Cyclooctanone 1,3,5,7-cyclooctatetraene Cyclopentadiene Cyclopentane Ht, 1.167 at 150.76 C; 0.823 at 135.08 C Cyclopentanethiol Cyclopentanol Cyclopentanone Cyclopentene Ht, 0.115 at 186.08 C Cyclopropane Decahydronaphthalene cis Ht, 0.511 at 57.1 C trans Decanal Decane 1-Decanethiol Decanoic acid 1-Decanol 1-Decene Ht, 1.90 at 74.8 C 1-Decyne Deoxybenzoin Dibenzilidene azine Dibenzyl ketone Dibenzyl sulfide Dibenzyl sulfone

0.576

8.58

10.36

47.82

71.00

87.30

99.01

2.695

8.700

38.45

52.77

62.23

68.88

0.1455

6.524

28.38

42.57

52.60

59.84

1.872

8.443

34.53

48.65

58.61

65.84

0.804 1.301

4.793

25.08 18.31

37.19 26.15

45.78 33.57

51.94 35.39

2.268 3.455

9.940 9.260

6.863 7.4 7.0 9.0 3.300

9.388 11.1

56.64 56.78 71.80 71.24 76.63

84.14 84.20 95.70 96.36 102.63

103.36 103.40 113.00 114.92 122.10

116.91 116.93 125.70 128.20 136.98

74.44 67.79 65.64

99.94 91.27 86.96

118.53 108.28 102.42

132.24 120.90 113.90

11.9 9.24

13.0 10.30 6.78 6.818 9.93 13.74 10.21 6.71

12.0 11.6 12.277 15.5 28.4 18.6 12.06 22.3 22.3 21.3 22.3 27.8

5.51

1,2-Dibromobutane 1,2-Dibromocycloheptane 1,2-Dibromocyclohexane 1,2-Dibromocyclooctane 1,2-Dibromoethane 1,2-Dibromoheptane 1,2-Dibromopropane Dibutylborinic acid Dibutyl ether Dibutyl mercury Di-tert-butyl peroxide Dibutyl o-phthalate Dibutyl sulfate Dibutyl sulfite Dibutyl sulfone Dichloroacetyl chloride 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene 2,6-Dichlorobenzoquinone 2,2-Dichlorobiphenyl 4,4-Dichlorobiphenyl Dichlorodifluoromethane 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene 1,2-Dichloroethylene cis trans Dichlorofluoromethane Dichloromethane 1,2-Dichloropropane 1,3-Dichloropropane 2,2-Dichloropropane

2.62

8.69

8.83

10.8 12.43 12.07 13.04 9.86 13.01 15 10.5 15.6 7.6 21.9 18.1 16.2 24.0 9.4 11.56 11.44 15.5 16.7 23.0 24.8

3.19

9.7

4.34

9.5

1.881 2.112 1.557

6.97 7.65 6.26

7.36 8.47 6.328

1.72 1.72

7.08 6.65

7.43 6.92

1.1

6.74 7.59 8.10 7.0

6.94 8.68 9.66 7.8

36.77

46.70

53.60

58.50

23.83

29.24

32.94

35.80

29.74

37.63

42.91

46.74

60.78

81.29

96.52

107.86

34.12 34.18 34.24

44.07 44.09 44.16

50.28 50.29 50.35

54.42 54.42 54.46

19.69 21.85 22.00 18.80

22.37 27.18 26.90 22.44

23.69 30.79 30.40 24.71

24.39 33.40 33.00 26.29

18.41 18.58 16.78 14.24 28.60 28.69 30.56

22.23 22.28 19.70 17.30 36.47 36.22 38.06

24.60 24.62 21.41 19.32 41.97 41.56 43.00

26.23 26.24 22.51 20.76 46.08 45.50 46.56

5.52

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance Dicyanoacetylene 2,2-Diethoxypropane Diethylamine 1,2-Diethylbenzene 1,3-Diethylbenzene 1,4-Diethylbenzene Diethylene glycol Diethyl ether Diethylmercury Diethylmethyl phosphonate Diethylnitramine Diethyl oxalate Diethyl peroxide Diethyl o-phthalate Diethyl selenide Diethyl sulfate Diethyl sulfite Diethyl sulfone Diethyl sulfoxide 1,2-Difluorobenzene 1,3-Difluorobenzene 1,4-Difluorobenzene 2,2-Difluorobiphenyl 4,4-Difluorobiphenyl 1,1-Difluoroethane 1,1-Difluoroethylene Difluoromethane

Hm

4.01 2.62 2.53 1.745

Hv

9.42 9.41 9.41 12.50 6.38

10.04

2.640

7.699

5.1

Hs 6.88 7.61 7.6 12.61 12.55 12.54 13.7 6.516 10.7 13.5 12.7 15.2 7.3 21.1 9.3 13.6 11.6 20.6 14.9 8.65 8.29 8.51 22.7 21.8

400 K

600 K

800 K

1000 K

34.88 56.01 55.01 54.68

47.14 75.66 75.19 74.84

56.16 89.54 89.31 89.04

62.91 99.49 99.37 99.16

33.01

43.92

52.26

58.51

32.76 32.72 32.84

43.33 43.13 43.20

50.12 49.67 49.68

54.72 53.93 53.99

19.93 17.16 12.22

25.70 21.32 15.72

29.70 23.95 18.22

32.57 25.74 19.98

9,10-Dihydroanthracene 4H-Dihydropyran 5,12-Dihydrotetracene 2,3-Dihydrothiophene 2,5-Dihydrothiophene 1,2-Diiodobenzene 1,2-Diiodoethane Diiodomethane Diisopropyl ether Diisopropyl ketone Diisopropylmercury 1,2-Dimethoxybenzene Dimethoxyborane 2,2-Dimethoxypropane Dimethylamine Dimethylaminotrimethylsilane 2,2-Dimethylbutane Ht, 1.289 at 147.34 C; 0.068 at 132.28 C 2,3-Dimethylbutane Ht, 1.552 at 137.08 C 2,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene a. Ht, b. 0.844 at76.34 C 3,3-Dimethyl-1-butene Ht, 1.037 at 148.3 C Dimethylcadmium 1,1-Dimethylcyclohexane Ht, 1.430 at 120.01 C 1,2-Dimethylcyclohexane cis Ht, 1.974 at 100.6 C trans 5.53

1,3-Dimethylcyclohexane cis trans

22.3 7.7 27.7 9.02 9.55 15.5 15.7 12.2

3.02(I) 2.88(II) 2.635

6.95

1.420

6.330

0.138

22.94 15.74

27.92 18.37

31.37 20.06

33.84 21.29

46.90

62.61

74.39

83.17

20.89

28.41

33.94

38.19

6.287

7.75 9.93 12.8 16.0 6.14 7.03 6.07 7.6 6.618

43.70

60.00

71.40

79.70

0.194

6.519

6.96

43.30

59.20

75.20

79.10

1.542

6.55 7.083

6.97 7.776

42.60 37.48

55.40 51.78

65.00 62.78

72.20 71.14

0.261

6.13

6.36

38.90

53.40

63.60

71.00

0.495

7.79

9.07 9.043

50.70

74.10

90.70

102.20

0.393 2.491(I) 2.508(II)

8.04 7.86

9.492 9.168

51.10 51.90

74.00 74.60

90.10 90.50

101.40 101.70

2.586 2.358

7.84 8.09

9.137 9.369

51.20 51.10

74.20 73.80

90.50 89.80

102.00 101.10

5.54

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance 1,4-Dimethylcyclohexane cis trans 1,1-Dimethylcyclopentane Ht, 1.551 at 126.36 C 1,2-Dimethylcyclopentane cis Ht, 1.594 at 131.66 C trans 1,3-Dimethylcyclopentane cis trans Dimethyldichlorosilane cis-2,4-Dimethyl-1,3-dioxane 4,5-Dimethyl-1,3-dioxane 5,5-Dimethyl-1,3-dioxane Dimethyl ether N,N-Dimethylformamide Dimethylfulvene Dimethylglyoxime 2,2-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane 2,2-Dimethyl-3-hexene cis trans

Hm

Hv

2.225 2.947 0.258

8.07 7.79 7.239

0.396 1.713

Hs

400 K

600 K

800 K

1000 K

9.329 9.053 8.079

51.10 51.60 43.55

73.80 74.60 62.78

89.80 90.60 76.18

101.10 101.90 85.83

7.576 7.375

8.549 8.259

43.67 43.71

62.72 62.66

75.98 75.84

85.57 85.43

1.761 1.738

7.265 7.361

8.200 8.248 8.2 9.53 10.16 9.86

43.71 43.71

62.66 62.66

75.84 75.84

85.43 85.43

1.180

5.141

19.02

25.16

30.04

33.79

1.62

3.096 1.7

7.71 7.94 7.79 7.80 7.76 7.95

11.4 10.6 23.2 8.91 9.27 9.03 9.05 8.97 9.32 8.88 8.91

1,1-Dimethylhydrazine 1,2-Dimethylhydrazine Dimethylmercury Dimethylnitramine 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,7-Dimethylphenanthrene 4,5-Dimethylphenanthrene 9,10-Dimethylphenanthrene 2,2-Dimethylpropane Ht, 0.616 at 133.14 C 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,5-Dimethylpyridine 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine Dimethyl sulfate Dimethyl sulfite Dimethyl sulfone Dimethyl sulfoxide 3,3-Dimethyl-2-thiabutane

5.55

2,2-Dimethylthiacyclopropane 2,2-Dimethyl-3-thiapentane 2,4-Dimethyl-3-thiapentane 1,3-Dinitrobenzene 2,4-Dinitrophenol 2,6-Dinitrophenol 1,1-Dinitropropane 1,4-Dioxane Ht, 0.562 at 0.3 C 1,3-Dioxolan

1.636 1.689

6.97 7.26 7.05 7.09

0.752

5.438

8.37 9.40 8.26 16.7 7.75 8.19 7.86 7.89 25.5 25.0 28.6 5.205

12.66 7.523

11.70 11.42 11.43 11.01 12.38 12.04 11.6 9.6 18.4 12.64 8.57

1.392

1.56 2.011(I) 1.83(II) 1.69 2.49

3.07

8.00 8.04

8.55 9.4 9.44 14.3 25 26.8 14.93 9.20 8.5

50.42 50.42 50.42 50.42

68.33 68.33 68.33 68.33

81.43 81.43 81.43 81.43

91.20 91.20 91.20 91.20

37.55

51.21

60.78

67.80

50.64

66.22

77.12

85.24

30.23

43.44

52.15

58.05

5.56

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance Dipentene Diphenylamine Diphenylchlorosilane Diphenyl disulfide Diphenyl disulfone 1,2-Diphenylethane 1,1-Diphenylethene Diphenyl ether Diphenylfulvene Diphenylmercury Diphenylmethane Diphenyl sulfide Diphenyl sulfone Diphenyl sulfoxide Dipropyl ether Dipropylmercury Dipropyl sulfate Dipropyl sulfite Dipropyl sulfone Dipropyl sulfoxide 2,3-Dithiabutane 5,6-Dithiadecane 3,4-Dithiahexane 1,3-Dithian-2-thione 4,5-Dithiaoctane N,N-Dithiodiethylamine 1,3-Diothiolan-2-thione Di-p-tolyl sulfone

Hm

Hv

12.3 4.115

2.197

15.525

2.248

8.05 11.2 9.01

3.30

10.02

Hs 11.5 23.1 16.6 22.7 38.7 20.1 17.5 19.6 25 26.95 19.7 16.2 25.4 23.2 8.6 13.2 16.0 14.0 19.1 17.8 9.17 15.2 10.89 21.85 12.55 12.6 19.56 26.2

400 K

600 K

800 K

1000 K

46.90

62.61

74.39

83.17

26.36 68.38 40.90

32.83 89.98 52.24

37.66 105.83 60.19

41.31 117.86 65.97

44.50

71.30

83.70

93.20

Divinyl ether Divinyl sulfone Dodecane Dodecanedioic acid 1-Dodecene Ht, 1.088 at 60.2 C Eicosane Eicosanoic acid 1-Eicosene meso-Erythritol Ethane 1,2-Ethanedithiol Ethanethiol Ethanol Ethyl acetate Ethyl allyl sulfone Ethylamine N-Ethylaniline Ethylbenzene 3-Ethyl-1-butene Ethyl crotonate Ethylcyclohexane 1-Ethylcyclohexene Ethylcyclopentane

5.57

Ethylene Ethylene carbonate Ethylene glycol Ethyleneimine Ethylene oxide Ethyl formate 2-Ethyl-1-hexanal 3-Ethylhexane Ethylisovalerate Ethyllithium

8.57

10.43

4.76

10.27

16.70 17.2 8.2

13.74 13.35

0.683

3.517

1.189 1.198 2.505

6.401 9.255 7.720 6.7

2.195

8.50 6.88

1.992

8.20

1.642(I) 1.889(II) 0.801 2.41 2.78

7.715

1.236 2.20

6.26 13.5 14.65 36.6 14.42 24.1 48 23.86 32.3 1.200 10.68 6.526 10.11 8.63 20.0 6.7 12.5 10.10 7.41 10.6 9.67 10.34 8.72

3.237 11.86 7.24 6.101 7.201 8.03

17.5 15.68 7.55 5.96 11.70 9.48 10.5 27.9

85.13

115.04

136.76

152.90

8.68

109.95

130.41

145.50

140.65

189.78

225.28

251.60

137.20

184.69

218.93

244.20

15.65

21.35

25.81

29.30

21.08 19.36 32.84

27.21 25.69 43.65

31.83 30.33 51.01

35.38 33.83 56.05

21.65

28.68

33.89

37.88

40.76 40.70

56.44 54.50

67.15 64.40

74.77 71.90

51.60

74.10

90.10

101.30

43.89

61.70

75.22

85.16

12.67

17.87

20.03

22.43

27.06 16.83 14.95

32.72 23.56 20.62

36.90 28.14 24.60

39.88 31.45 27.47

5.58

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance Ethylmercury bromide Ethylmercury chloride Ethylmercury iodide Ethyl methyl ether Ethyl nitrate 3-Ethylpentane Ethyl pentanoate 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol Ethylphosphonic acid Ethyl propanoate Ethyl -vinylacrylale Ethyl vinyl ether Ethynylbenzene Fluoranthrene Fluorobenzene 4-Fluorobenzoic acid Fluoroethane Fluoromethane 1-Fluoropropane 2-Fluoropropane 4-Fluorotoluene Fluorotrinitromethane Formaldehyde Formic acid Formyl HCO · HCO

Hm

Hv

Hs

400 K

600 K

800 K

1000 K

26.08 28.73 50.42

34.58 37.07 68.33

41.19 42.72 81.43

46.18 46.69 91.20

35.95

48.01

55.79

61.17

29.99

40.86

47.83

52.58

17.71 10.56 24.55 24.72 36.43

23.56 13.83 32.82 33.14 49.70

27.82 16.45 38.88 39.14 58.60

31.00 18.44 43.37 43.55 64.84

9.38 12.85

11.52 16.02

13.37 18.35

14.81 19.95

8.73 9.39

9.79 10.39

10.75 11.14

11.49 11.78

18.3 18.2 19.0 2.04 2.282

7.92 7.40

8.178

2.702

7.457

2.235

8.144

3.035

5.85 5.24

8.67 8.42 11.0 15.20 16.30 19.20 12.1 9.0 11.6 6.35 24.65 8.27 21.8

9.42 8.3 11.03

Fumaric acid Fumaronitrile Furan Ht, 0.489 at 123.2 C Furfuryl alcohol 2-Furoic acid Furylethylene Glycerol Glyceryl triacetate Glyceryl trinitrate Heptadecane Ht, 2.62 at 11.1 C Heptadecanoic acid 1-Heptadecene 1-Heptanal Heptane 1-Heptanethiol Heptanoic acid 1-Heptanol 1-Heptene Ht, 0.07 at 1.36 C

5.59

Hexachlorobenzene Hexachloroethane Ht, 1.9 at 71.3 C Hexadecafluoroethylcyclohexane Hexadecafluoroheptane Hexadecane Hexadecanoic acid 1-Hexadecanol Ht, 4.8 at 44.0 C; 5.7 at 49.1 C 1-Hexadecene Hexafluorobenzene Hexafluoroethane Ht, 0.893 at 169.17 C Hexahydroindane cis trans

0.909 3.12

6.474

4.416

9.67 12.3 7.5 5.637 3.359 6.067 3.16 2.964(I) 3.021(II) 6.1 2.33

12.39 12.8 7.8 7.216 2.770 0.642

32.5 17.2 6.61 15.4 25.92 9.1

21.20

29.31

34.41

37.89

20.5 19.6 23.9 12.64

20.6

119.83

161.75

192.08

214.60

12.39

20.32 11.40 8.74 12.06 18.0 16.5 8.52

116.38 51.00 50.42 55.81

156.66 67.70 68.33 74.60

185.74 79.80 81.43 88.91

207.20 88.70 91.20 99.98

53.62 46.97

71.92 63.24

85.32 75.09

95.25 83.90

23.2 16.5 9.20 8.7 19.38 36.9 40.5

48.08 36.21

55.78 39.82

59.96 41.48

62.34 42.38

112.89

152.41

181.02

202.20

116.09

156.00

184.90

206.30

109.44 43.88 30.01

147.32 52.55 35.60

174.67 57.62 38.40

194.80 60.63 39.87

7.575 9.5 11.5 7.43

12.2

12.24

12.05 7.571 3.860

19.14 8.61

11.0 10.7

5.60

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance

Hm

Hexamethylbenzene Ht, 0.269 at 156.67 C; 0.422 at 110.7 C Hexmethyldisiloxane Hexanal Hexanamide Hexane 1-Hexanethiol Hexanoic acid 1-Hexanol 1-Hexene 2-Hexene cis trans 3-Hexene cis trans 1-Hexyne Hydroquinone 8-Hydroxyquinoline

4.93

Indane Indene Indole Iodobenzene 4-Iodobenzoic acid Iodocyclohexane Iodoethane Iodomethane

Hv

Hs

400 K

600 K

800 K

1000 K

17.9

74.18

97.13

113.51

125.55

44.00

58.30

68.70

76.40

8.9

3.126 4.305 6.98 3.68 2.234

6.896 8.9 15.45 11.6 6.76

22.72 7.54 11.14 17.3 14.8 7.32

43.47 48.87

58.99 65.26

70.36 77.84

78.89 87.65

46.68 40.03

62.58 53.90

74.25 64.02

82.92 71.54

6.96 6.91

7.52 7.54

38.60 39.70

53.00 53.40

63.40 63.60

71.20 71.20

6.86 6.92

7.47 7.54

38.50 40.20 37.87

53.20 53.90 49.59

63.50 63.90 58.16

71.20 71.40 64.56

31.10

41.43

48.07

52.60

19.18 12.33

24.64 15.28

28.65 17.47

31.65 19.17

23.7 26.0

2.33

9.44

7.115 6.52

11.8 12.64 16.7 11.85 21.0 11.3 7.7 6.63

2-Iodo-2-methylpropane 1-Iodonaphthalene 2-Iodonaphthalene 1-Iodopropane 2-Iodopropane 3-Iodopropene Iodotoluene, 3- and 4Isobutylbenzene Isobutyl dichloroacetate Isobutyl phenyl ketone Isobutyl trichloroacetate Isobutyronitrile Isopropyl acetate Isopropylbenzene Isopropyl nitrate Isopropyl trichloroacetate Isothiocyanic acid

3.47

7.754

8.99

1.86

8.97 8.35

Ketene Lauric acid Leucine ()-Limonene

5.61

Maleic acid Maleic anhydride Malononitrile D-Mannitol Melamine 2,2-Metacyclophane Methane Ht, 0.0187 at 248 to 252.7 C Methanethiol Ht, 0.0525 at 135.6 C Methanol Ht, 0.152 at 115.8 C 4-Methoxybenzaldehyde Methoxybenzene 2-Methoxytetrahydropyran Methyl (CH3)

8.46 17.3 21.7 8.6 8.14 9.1 13.0 11.54 12.5 14.22 12.7 28.56 8.89 10.79 9.27 12.4 4.18

8.8

35.27

45.82

52.85

57.91

26.27 26.59

34.11 34.58

39.80 40.21

44.03 44.34

37.39

43.74

48.40

48.00 35.96

66.20 46.81

78.60 54.13

87.30 59.26

12.71

14.57

15.74

16.57

14.22

16.89

18.80

20.25

9.71

12.55

15.18

17.40

14.04 12.29

17.57 16.02

20.32 19.04

22.48 21.38

10.05

11.54

12.89

14.09

31.7 36.0 11.5 26.3 17.1 18.9

5.39 29.7 22.0 0.225

1.953

1.411 0.768

5.872 8.24

5.7 8.94 15.42 11.18 10.2

5.62

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance Methyl allyl sulfone Methylamine Methyl benzyl sulfone 2.Methyl-1,3-butadiene 3-Methyl-1,2-butadiene 2-Methylbutane 2-Methyl-1-butanethiol 3-Methyl-1-butanethiol 2-Methyl-2-butanethiol Ht, 1.907 at 114.0 C 3-Methylbutanoic acid 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol Ht, 0.47 at 127.2 C 3-Methyl-2-butanol 2-Methyl-1-butene 3-Methyl-1-butene 2-Methyl-2-butene Methyl butyl sulfone Methyl tert-butyl sulfone 3-Methyl-1-butyne Methyl crotonate Methylcyclohexane 2-Methylcyclohexanol, cis- and trans3-Methylcyclohexanol cis trans

Hm

Hv

1.466

6.169

1.155

6.191 6.51 5.901 8.0

1.231 1.78 0.1454 1.750

1.06

1.891 1.281 1.816

7.50 10.32 10.5 10.54 9.6 9.9 6.094 5.750 6.287

6.25 1.614

7.44

Hs

400 K

600 K

800 K

1000 K

19.0 5.80 23.7 6.32 6.68 5.94

14.38

18.86

22.44

25.26

31.80 31.00 36.49

41.40 40.30 49.89

48.00 47.20 59.71

52.90 52.40 67.12

8.51

42.79

56.58

66.28

73.30

33.20 35.26 31.93

44.72 45.90 43.42

53.15 53.85 52.05

59.43 59.83 58.55

31.10

40.60

47.40

52.40

44.35

64.46

78.74

88.79

12.9 13.0 11.9 12.4 6.181 5.70 6.468 18.2 19.7 6.16 9.8 8.45 15.1 15.6 15.7

4-Methylcyclohexanol cis trans Methylcyclopentane 1-Methylcyclopentene 3-Methylcyclopentene 4-Methylcyclopentene Methyldichlorosilane 2-Methyl-1,3-dioxane 4-Methyl-1,3-dioxane Methylene (CH2) 1-Methyl-2-ethylbenzene 1-Methyl-3-ethylbenzene

5.63

1-Methyl-4-ethylbenzene 2-Methyl-3-ethylpentane 3-Methyl-3-ethylpentane 2-Methyl-3-ethyl-1-pentene Methyl ethyl sulfite Methyl ethyl sulfone Methyl formate Methylglyoxal 2-Methylheptane 3-Methylheptane 4-Methylheptane Methyl heptanoate 2-Methylhexane 3-Methylhexane Methyl hexanoate Methylhydrazine Methylidyne CH CH 1-Methyl-2-isopropylbenzene

1.656

6.95

2.38 2.28 1.82 1.79 3.19 2.71 2.59

9.29

1.800

6.75

36.11 32.50 32.60 32.60

52.43 46.80 47.10 47.00

64.00 57.00 57.20 57.10

72.44 64.30 64.50 64.40

11.40

8.64 48.50

9.37 65.80

10.14 78.10

10.89 86.90

9.21

11.21

47.50

65.40

77.80

86.80

9.18 7.88 7.84

11.14 9.20 9.08 8.98 10.4 18.6

47.20

65.00

77.60

86.60

19.50

25.20

29.10

32.00

50.42 50.42

68.33 68.33

81.43 81.43

91.20 91.20

6.98 6.98

7.11 7.10

7.40 7.36

7.78 7.65

2.839 2.779 2.59

8.08 8.10 8.10

2.195

7.33 7.36

2.39

15.7 15.8 7.55 7.55 7.7 7.7 6.7 9.23 9.36

9.17

9.1 9.48 9.52 9.48 12.0 8.32 8.39 11.1 9.65

12.10

5.64

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance

Hm

Hv

Hs

1-Methyl-3-isopropylbenzene 1-Methyl-4-isopropylbenzene Methyl isopropyl ether Methyl isopropyl ketone Methyl isopropyl sulfone 3-Methylisoxazole 5-Methylisoxazole Methylmercury bromide Methylmercury chloride Methylmercury iodide 1-Methylnaphthalene Ht, 1.190 at 32.37 C 2-Methylnaphthalene Ht, 1.34 at 15.4 C Methyl nitrate Methyl nitrite 2-Methylpentane 3-Methylpentane Methyl pentanoate 2-Methyl-1-pentene 3-Methyl-1-pentene 4-Methyl-1-pentene 2-Methyl-2-pentene 3-Methyl-2-pentene cis trans 4-Methyl-2-pentene cis trans

3.27 2.31

9.11 9.12

11.94 12.02 6.27 8.82 16.8 9.8 10.0 16.2 15.5 15.6

400 K

600 K

800 K

1000 K

32.97

44.17

52.67

59.08

1.160

11.0

50.74

69.79

82.48

91.21

2.808

11.0

50.50

69.31

82.03

90.86

21.87 18.24 44.00 43.47

27.54 23.35 59.60 59.00

31.47 26.97 70.80 70.40

34.19 29.52 79.20 78.90

6.71 6.43 6.47 6.93

8.1 5.4 7.138 7.236 10.2 7.29 6.83 6.86 7.55

40.80 42.50 38.90 39.00

54.40 55.60 52.90 53.20

64.40 65.20 63.10 58.60

71.80 72.30 70.70 71.10

6.89 7.00

7.49 7.67

39.00 39.00

53.20 53.20

63.40 63.40

71.10 71.10

6.59 6.68

7.04 7.16

40.05 41.90

54.10 54.80

64.00 64.50

71.50 71.80

1.97 1.498

7.54 5.0 6.643 6.711

Methyl phenyl sulfone Methylphosphonic acid 2-Methylpropanal 2-Methylpropane 2-Methyl-1-propanethiol 2-Methyl-2-propanethiol Ht, 0.972 at 121.6 C; 0.155 at 116.2 C; 0.232 at 73.8 C 2-Methyl-1-propanol 2-Methyl-2-propanol Ht, 0.20 at 12.99 C 2-Methylpropene Methyl propyl ether 2-Methylpyridine 3-Methylpyridine -Methylstyrene -Methylstyrene cis trans 3-Methyl-2-thiabutane 2-Methylthiacyclopentane 2-Methyl-3-thiapentane 4-Methylthiazole 2-Methylthiophene 3-Methylthiophene

5.65

Naphthalene 1-Naphthol 2-Naphthol 1,4-Naphthoquinone 1-Naphthylamine 2-Naphthylamine p-Nitroaniline Nitrobenzene 1-Nitrobutane 2-Nitrobutane

1.085 1.191

5.089 7.412

22.0 11.5 7.5 4.57 8.28

0.593

6.80

7.36

36.13

47.60

55.53

61.24

1.602

9.80 9.33

12.04 12.73

34.16

45.37

53.28

59.16

1.418

5.286

2.324 3.389

8.654 8.932

4.92 6.6 10.15 10.62

26.57 33.01 31.92 31.82 44.80

35.30 43.92 44.55 44.47 60.70

41.86 52.26 53.21 53.12 71.80

46.85 58.51 59.34 59.23 79.80

44.80 45.20 34.69

60.70 61.20 46.01

71.80 72.20 54.95

79.80 80.00 62.29

29.43 29.38

39.57 39.34

46.43 45.95

51.30 50.59

17.6 21.9 19.8 17.3 21.5 21.1 26

42.83

59.67

70.77

78.38

11.6 10.48

37.65 37.61

50.21 50.46

59.03 59.44

65.39 65.96

2.236

7.338 8.7

2.08 2.263 2.518 4.536

5.04 2.78

8.103 8.186 10.34

9.744 9.3 8.8

8.15 10.1 9.2 10.48 9.26 9.44

29.77 35.31

40.62 46.26

48.49 53.77

54.40 59.17

5.66

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance Nitroethane Nitromethane 1-Nitronaphthalene 1-Nitropropane 2-Nitropropane Nonadecane Ht, 3.30 at 22.8 C 1-Nonadecene 1-Nonanal Nonane Ht, 1.50 at 55.97 C 1-Nonanethiol Nonanoic acid 1-Nonanol 1-Nonene Octadecane Octadecanoic acid 1-Octadecene Octafluorocyclobutane 1-Octanal Octanamide Octane 1-Octanethiol Octanoic acid 1-Octanol 1-Octene 1-Octyne Oxalic acid Ht, 0.3( → ) Oxalyl chloride Oxamide

Hm

Hv

Hs

400 K

600 K

800 K

1000 K

2.319

8.4 8.12

9.9 9.17 25.6 10.37 9.88 22.9 22.68 17.28 11.10

23.66 16.80

31.45 21.92

36.81 25.56

40.67 28.17

30.72 30.89 133.71 130.26 64.80 64.30 69.69

40.87 41.19 180.43 175.35 86.40 87.01 93.28

47.96 48.22 214.21 207.86 101.90 103.56 111.04

53.06 53.24 239.20 231.80 113.40 115.90 124.65

67.50 60.85

90.60 81.93

107.46 97.22

119.91 108.50

126.77

171.09

203.15

226.90

123.32 44.50 57.90

166.00 53.85 77.00

196.80 58.65 90.90

219.50 61.50 101.00

57.35 62.75

77.67 83.94

92.50 99.97

103.60 112.31

60.56 53.91 51.75

81.26 72.58 68.28

96.39 86.15 80.30

107.58 96.20 89.20

10.95 8.0

8.8 8.4 13.39 13.06

3.72 8.0

8.82 10.6

4.3

13.0 8.68

14.81 15.1 7.8 0.662

4.957 58 3.30 10.1 3.660

13.02 12.74 5.58

8.225 10.1 16.73 11.2 8.07

19.7 18.6 10.88 21.7 39.8 21.50 16.28 26.4 9.916 19.2 15.6 9.70 23.4 7.6 26.8

5.67

Palmitic acid [1.8]-Paracyclophane [2.2]-Paracyclophane [6.6]-Paracyclophane Paraldehyde Pentachloroethane Pentachlorofluoroethane Pentachlorophenol Pentadecane Ht, 2.19 at 2.25 C 1-Pentadecene 1,2-Pentadiene 1,3-Pentadiene cis trans 1,4-Pentadiene 2,3-Pentadiene Pentaerythritol Pentaerythritol tetranitrate Pentafluorobenzoic acid Pentafluoroethane Pentafluorophenol Pentamethylbenzene Ht, 0.473 at 23.7 C 1-Pentanal Pentanamide Pentan-2,4-dione Pentane Pentan-1,5-dithiol Pentanenitrile 1-Pentanethiol Pentanoic acid 1-Pentanol 2-Pentanol 3-Pentanol 2-Pentanone

10.30

2.7 0.449

8.9

37 26.5 23.0 27.5 9.9 10.9

8.31 6.9

11.82 11.63 6.59

16.1 18.20 17.96 6.85

1.468

6.60 6.46 6.01 6.75

6.77 6.64 6.01 7.05 34.4 36.3 21.9

31.96

36.35

38.71

40.17

105.95 102.50 31.40

143.07 137.98 40.80

169.95 163.60 47.70

189.90 182.50 52.80

29.50 31.20 31.30 29.90

39.90 40.90 40.80 39.40

47.00 47.70 47.60 46.60

52.20 52.60 52.70 52.00

27.20

32.94

36.12

37.98

65.00

86.08

101.29

112.33

37.10

49.00

57.70

64.00

36.53

49.64

59.30

66.55

41.93

55.92

66.78

75.32

39.74

53.24

63.18

70.59

36.42

48.32

57.13

63.61

16.1 2.95

2.008

6.16

1.130 4.19 3.850 2.34

7.98 8.34 10.53 10.6 10.3 10.1 7.98

21.34 10.82 6.32 14.17 9.83 16.6 13.61 12.7 12.8 9.89

5.68

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance

Hm

Hv

Hs

400 K

600 K

800 K

1000 K

1-Pentene 2-Pentene cis trans 1-Pentyne 2-Pentyne Perylene -Phellandrene 9,10-Phenanthraquinone Phenanthrene Phenol Phenyl acetate -Phenyl-1-alanine, DL- and LPhenyl benzoate N-Phenyldiacetimide Phenyl ethyl sulfide Phenylhydrazine 1-Phenyl-2-methylpropane Phenyl methyl sulfide Phenyl salicylate Phosgene

1.388

6.02

6.09

33.10

44.56

52.95

59.21

1.700 1.996

6.24 6.23 6.63 6.99

6.41 6.38 6.79 7.35 30.0 12.1 21.9 21.1 16.41 13.0 36.8 23.0 21.5 13.2 14.69 11.82 12.1 22.0

31.57 32.67 31.10 29.20

43.62 44.02 40.40 38.70

52.29 52.45 47.10 45.90

58.78 58.81 52.20 51.40

32.45

43.54

50.62

55.49

15.28

16.98

17.92

18.49

m-Phthalic acid p-Phthalic acid Phthalic anhydride -Pinene

2.752

13.3 9.73

2.99

9.04

1.372 1.335 1.131

5.832

25.5 23.5 21.19 10.7

-Pinene Propadiene 1-Propanal Propane Propane-2,3-dithiol 1-Propanethiol Ht, 0.949 at 131.06 C 2-Propanethiol Ht, 0.013 at 160.6 C 1-Propanol 2-Propanol 2-Propen-1-ol Propionic acid Propionic anhydride Propionitrile Ht, 0.408 at 96.19 C 1-Propylamine Propylbenzene

5.69

Propyl carbamate Propyl chloroacetate Propylcyclohexane Propylcyclopentane Propylene Propylene oxide Propyl nitrate Propyl phenyl ketone Propyl trichloroacetate Propyne Pyrazine Pyrene Pyridazine Pyridine Pyrimidine Pyrrole Pyrrolidine Ht, 0.129 at 66.01 C Salicyclic acid Sebacic acid

11.1 4.45 0.842

4.487

1.309 1.371 1.242 1.293

7.059 6.670 9.982 9.510

1.800

7.716

1.202

7.353

2.215 2.03

9.14

2.479 2.398 0.718 1.561

8.62 8.15 4.40 6.87 8.58

7.09 3.605 11.87 7.62 7.039 11.36 10.85 11.3 13.7 12.6 8.632 7.46 11.05 19.4 11.6 10.78 9.82 6.67 9.70 14.51 12.7

5.29

1.979

8.39

2.050

7.89

13.45 22.5 12.78 9.61 11.95 10.80 8.98 22.74 38.4

17.21 23.09 22.47

22.00 30.22 30.76

25.42 35.45 36.99

28.00 39.27 41.73

27.86 28.35 25.86 26.78 22.81

36.72 37.02 34.56 35.76 30.11

43.60 43.26 41.04 42.13 35.28

49.01 47.92 45.93 46.82 39.06

21.18 28.51 47.82

27.42 37.99 65.86

32.14 44.94 78.30

35.70 50.21 87.16

59.10 50.83 19.23 22.16 35.79

83.80 71.04 25.81 30.07 46.49

101.20 86.28 30.77 35.68 53.87

113.40 97.50 34.52 39.79 59.08

17.33

21.80

25.14

27.71

25.42

35.72

42.49

47.17

27.33

40.31

49.35

55.84

5.70

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance 5,5-Spirobis(1,3-dioxane) Spiropentane cis-Stilbene Styrene Suberic acid Succinic acid Tetrabromomethane Tetracene Tetrachlorobenzoquinone 1,1,1,2-Tetrachloroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetrachloromethane Ht, 1.095 at 47.9 C Tetracyanoethylene Tetradecane Tetradecanoic acid 1-Tetradecene Tetraethylene glycol Tetraethyllead 1,1,1,2-Tetrafluoroethane Tetrafluoroethylene Tetrafluoromethane Ht, 0.353 at 196.92 C Tetrahydrofuran Tetrahydrofurfuryl alcohol 1,2,3,4-Tetrahydronaphthalene Tetrahydropyran

Hm

Hv

1.538

6.39

2.617

8.85

Hs 17.4 6.58 16.5 10.50 34.2 28.1

400 K

600 K

800 K

1000 K

28.55

40.10

47.91

53.51

38.32

52.14

61.40

67.92

23.20

24.51

25.51

25.32

28.36 27.90 25.10

33.28 32.91 27.86

36.24 35.85 29.29

38.17 37.76 30.07

21.92

23.82

24.64

25.05

99.01

133.72

158.89

177.60

95.56

128.64

152.54

170.20

24.90 21.97

30.76 25.53

34.20 27.61

36.36 28.86

17.30

20.74

22.58

23.61

30 23.6

2.5

9.24 8.3

10.7 9.4

0.601

7.16

7.79 19.4 17.01 33.4 16.78 24 13.6

10.90

11.38

6.6

11.21

1.844

4.02

0.167 7.65 15.9 13.4 8.35

5.71

Tetraiodomethane 1,2,3,4-Tetramethylbenzene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane Ht, 0.478 at 120.66 C Tetramethyllead Tetranitromethane Tetrazole 2-Thiabutane Thiacyclobutane Ht, 0.160 at 96.45 C Thiacycloheptane Thiacyclohexane Ht, 0.262 at 71.75 C; 1.858 at 33.14 C Thiacyclopentane Thiacyclopropane 4-Thia-5,5-dimethyl-1-hexene 2-Thiaheptane 3-Thiaheptane 4-Thiaheptane 2-Thiahexane 3-Thiahexane 5-Thianonane 2-Thiapentane 3-Thiapentane 2-Thiapropane 6-Thiaundecane Thioacetic acid Thiophene Ht, 0.152 at 101.6 C Thymol Toluene 2-Toluenethiol 2,4,6-Triamino-1,3,5-triazine

24.00 56.81 55.76 55.50

24.94 75.68 74.81 74.38

25.31 89.42 88.79 88.41

25.49 99.47 99.01 98.71

9.1 10.3 23 7.61

27.81

36.41

42.93

47.94

7.7

8.56 11.30

21.89 42.0

30.45 65.0

36.40 79.0

40.67 88.0

0.585

8.60

10.22

35.71

52.37

64.00

72.34

1.757

8.28 6.98

28.95 16.53

40.04 21.99

47.66 25.61

53.14 28.21

2.96 2.90 2.976 2.529 4.64 2.369 2.845 1.908

8.78 8.76 8.2 8.3

9.28 7.24 10.6 10.88 10.74 10.64 9.8 9.58 12.75 8.65 8.55 6.61 14.7

48.67 48.37 48.21 41.73 41.43 62.09 34.64 34.65 21.12

65.02 64.96 65.13 55.68 55.62 83.81 45.86 46.11 27.01

77.59 77.74 78.45 66.53 66.68 100.58 54.45 54.91 31.58

87.41 87.75 89.05 75.08 75.42 113.71 61.14 61.79 35.17

1.216

7.52

22.25 23.02

26.72 30.95

30.41 36.01

32.62 39.54

1.586

7.93

33.48

47.20

56.61

63.32

2.684 2.561 5.02 1.802

10.76 10.47 10.88 7.51

13.66 13.34 18 10.24

2.333

7.06

1.971

7.62 7.59 6.45

8.27 21.8 9.08 12.3 29.5

5.72

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance Tribromomethane Tributyl phosphate Trichloroacetyl chloride Trichlorobenzoquinone 1,1,1-Trichloroethane Ht, 1.79 at 48.95 C 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane Trichloromethyl (CCl3) 1,2,3-Trichloropropane Tricyanoethylene Tridecane Ht, 1.831 at 18.2 C Tridecanoic acid 1-Tridecene Trimethylaluminum Triethylamine Triethylaminoborane Triethyl arsenite Triethylarsine Triethyl borate Triethylenediamine Ht, 2.30 at 79.8 C Triethylene glycol Triethyl phosphate Triethylphosphine Triethyl phosphite Triethylstibine

Hm

Hv

Hs

400 K

600 K

800 K

1000 K

18.80

21.03

22.29

23.12

25.72 25.03 21.80 20.84 16.66 31.71

30.68 30.13 25.06 23.13 18.16 38.87

33.73 33.28 26.94 24.19 18.83 43.79

35.81 35.42 28.15 24.74 19.18 47.34

92.07

124.38

147.82

165.20

88.62

119.29

141.48

157.80

48.70

66.10

78.56

87.80

17.2 9.8 21.2 0.45 2.7

6.81 8.2 6.2

7.96 8.3 7.52

7.76 9.4 8.2

8.87

11.22 19.4 15.83 35.0 15.60 17.5 8.29 14.5 12.1 10.3 10.5

10.91 10.75

1.45 17.07

14.8 18.9 13.7 9.5 10.0 10.4

1,1,1-Trifluoroethane Trifluoroethylene Trifluoromethane Trifluoromethyl CF2 CF3 Trifluoromethylbenzene Triodomethane 2,4,5-Trimethylacetophenone 2,4,6-Trimethylacetophenone Trimethylaluminum Trimethylamine Trimethyl arsenite Trimethylarsine 1,2,3-Trimethylbenzene Ht, 0.157 at 54.46 C; 0.319 at 42.89 C 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene

5.73

Trimethyl borate Trimethylboron 2,2,3-Trimethylbutane Ht, 0.586 at 157.8 C Trimethylchlorosilane cis,cis-1,3,5-Trimethylcyclohexane 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane Ht, 1.850 at 109.01 C 2,3,4-Trimethylpentane 2,4,4-Trimethyl-1-pentene 2,4,4-Trimethyl-2-pentene Trimethylphosphine Trimethylphosphine oxide

1.480

4.58

0.970

3.99

3.29 3.9

7.80

1.564

5.48

1.955

9.57

8.98 16.7 15.1 14.9 15.1 5.26 10.1 6.9 11.73

3.153 2.274 1.932 1.892

9.38 9.33

11.46 11.35

22.75 19.39 14.61

28.38 23.30 18.16

31.98 25.69 20.35

34.44 27.23 21.76

13.74 13.62 40.59 19.60

16.17 16.00 54.20 21.52

17.50 17.35 62.75 22.64

18.25 18.13 68.45 23.38

28.08

38.34

45.62

50.98

46.90

64.00

76.70

85.90

46.96 46.41

64.29 64.08

76.93 76.84

86.10 86.07

50.83

69.61

82.73

92.32

58.05

83.94

102.20

115.21

8.3 4.83 0.540

6.92

7.65 7.2

2.06 2.20 0.205

7.65 7.41 7.73

8.82 8.40 8.90

2.215

7.82 7.5 7.8

9.01 8.5 8.9 6.7 12.0

5.74

TABLE 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds (continued ) Cp Substance

Hm

Hv

Trimethyl phosphite Trimethylsilanol Trimethylstibine Trimethylsuccinic anhydride Trimethylthiacyclopropane 2,4,6-Trinitroanisole 1,3,5-Trinitrobenzene Trinitromethane 2,4,6-Trinitrophenetole 2,4,6-Trinitrotoluene Triphenylarsine Triphenylene Triphenylmethane Triphenylphosphine Tropolone

Hs

400 K

600 K

800 K

1000 K

13.47 29.0 13.24 21.0

78.18

105.80

125.69

140.60

74.74

100.61

119.34

133.20

10.38 10.20 10.13 20.1 15.74 20.31 18.07 20.49 19.80

41.03 40.03 39.70

55.98 55.51 55.16

66.64 66.41 66.14

74.35 74.23 74.02

8.8 10.9 7.5 17.7 9.40 31.8 23.8 11.15 28.8 28.3 23.5 28.2 23.9 23 20.0

Undecane Ht, 1.64 at 36.55 C Undecanoic acid 1-Undecene Ht, 2.202 at 55.8 C Urea

5.28 6.2 4.06

9.92

o- Xylene m-Xylene p-Xylene 2,3-Xylenol 2,4-Xylenol 2,5-Xylenol 2,6-Xylenol 3,4-Xylenol 3,5-Xylenol

3.25 2.765 4.09

8.80 8.69 8.60

9.77

5.75

THERMODYNAMIC PROPERTIES

CRITICAL PHENOMENA The critical temperature Tc of a gas is the temperature above which the gas cannot be liquefied no matter how high the pressure. The critical pressure Pc is the lowest pressure which will liquefy the gas at its critical temperature. The critical molar volume Vc is the volume of 1 mol at the critical temperature and the critical pressure. It can be computed from the critical density c as follows: Molecular weight in g·mol1 c in g ·cm3

 Vc in cm3 · mol1

The critical pressure, critical molar volume, and critical temperature are the values of the pressure, molar volume, and thermodynamic temperature at which the densities of coexisting liquid and gaseous phases just become identical. At this critical point the critical compressibility factor Zc is Zc 

PcVc RTc

Since pressure, volume, and temperature are related to the corresponding critical properties, the function connecting the reduced properties becomes the same for each substance. The reduced property is expressed as a fraction of the critical property. Pr 

V P T ¬ Vr  ¬ Tr  Pc Vc Tc

TABLE 5.3 Critical Properties Substance

Tc, K

Pc, atm

Vc, cm3 · mol1

Acetaldehyde Acetic acid Acetic anydride Acetone Acetonitrile Acetophenone Acetyl chloride Acetylene Acrylic acid Acrylonitrile Air Allene Allyl alcohol Allyl sulfide Aluminum trichloride Aminoethanol Ammonia Aniline Anisole Anthracene Antimony tribromide Antimony trichloride

461 594.4 569 508.1 548 701 508 308.3 615 536 132.5 393 545 653 629 614 405.6 699 368 883 904.5 794

55 57.1 46.2 46.4 47.7 38 58 60.6 56 45 37.2

154 171.3 290 209 173 376 204 113 210 210 92.7

56.4

203

26 44 111.3 52.4 41.2

261 196 72.5 270

56 270

5.76

SECTION 5

TABLE 5.3 Critical Properties (continued ) Substance

Tc, K

Pc, atm

Vc, cm3 · mol1

Argon Arsine

150.8 373.0

48.1

74.9

Benzaldehyde Benzene Benzoic acid Benzonitrile Benzyl alcohol Biphenyl Bismuth tribromide Bismuth trichloride Boron pentafluoride Boron tribromide Boron trichloride Boron trifluoride Bromine Bromobenzene Bromoethane Bromomethane Bromopentafluorobenzene Bromotrifluoromethane 1,2-Butadiene 1,3-Butadiene Butane 1-Butanol 2-Butanol 2-Butanone 1-Butene cis-2-Butene trans-2-Butene 3-Butenenitrile 1-Buten-3-yne Butyl acetate 1-Butylamine N-Butylaniline Butylbenzene sec-Butylbenzene tert-Butylbenzene Butyl benzoate Butylcyclohexane sec-Butylcyclohexane tert-Butylcyclohexane Butyl ethyl ether 1-Butyne 2-Butyne Butyraldehyde Butyric acid Butyronitrile

695 562.1 752 699.4 677 789 1219 1179 470 573 451.9 260.8 584 670 503.8 464 670 340.2 443.7 425 425.2 562.9 536.0 535.5 419.6 435.6 428.6 585 455 579 524 72 660.5 664 660 723 667 669 659 531 463.7 488.6 524 628 582.2

46 48.3 45 41.6 46 38

Carbon dioxide Carbon disulfide

304.2 552

72.8 78.0

118

259 341 334 502 301 261 280

38.2 49.2 102 44.6 61.5 85 44.6 39.2 44.4 42.7 37.5 43.6 41.4 41.0 39.7 41.5 40.5 39 49 31 41 28 28.5 29.1 29.3 26 31.1 26.4 26.3 30 46.5 502 40 52.0 37.4

127 324 215

200 219 221 255 274 268 267 240 234 238 265 202 400 288 518 497

561

390 220 221 278 292 285 94.0 170

5.77

THERMODYNAMIC PROPERTIES

TABLE 5.3 Critical Properties (continued ) Substance

Tc, K

Pc, atm

Vc, cm3 · mol1

Carbon monoxide Carbon tetrachloride Carbon tetrafluoride Carbonyl chloride (phosgene) Carbonyl sulfide Chlorine Chlorine pentafluoride Chlorine trifluoride Chlorobenzene 1-Chlorobutane 2-Chlorobutane 1-Chloro-1, 1-difluoroethane 2-Chloro-1,l-difluoroethylene Chlorodifluoromethane Chloroethane Chloroform Chloromethane 2-Chloro-2-methylpropane Chloropentafluoroacetone Chloropentafluoroethane 1-Chloropropane 2-Chloropropane 3-Chloropropene Chlorotrifluoromethane Chlorotrifluorosilane o-Cresol m-Cresol p-Cresol Cyanogen Cyclobutane Cycloheptane Cyclohexane Cyclohexanol Cyclohexanone Cyclohexene Cyclopentane Cyclopentanone Cyclopentene Cyclopropane Cymene

132.9 556.4 227.6 455 375 417 415.7 426.6 632.4 542 520.6 410.2 400.5 369.2 460.4 536.4 416.3 507 410.7 353.2 503 485 514 302.0 308.5 697.6 705.8 704.6 400 459.9 589 553.4 625 629 560.4 511.6 626 506.0 397.8 658

34.5 45.0 36.9 56 58 76.1 51.9

93.1 276 140 190 140 124 230.9

44.6 36.4 39 40.7 44.0 49.1 52.0 54.0 65.9 39 28.4 31.2 45.2 46.6 47 38.7 34.2 49.4 45.0 50.8 59 49.2 36.7 40.2 37 38 42.9 44.5 53

308 312 305 231 197 165 199 239 139 295

210 390 308 327 312 292 260 268

54.2

170

cis-Decalin trans-Decalin Decane Decanenitrile 1-Decanol 1-Decene Decylcyclohexane Decylcyclopentane

702.2 690.0 617.6 621.9 700 615 750 723.8

31 31 20.8 32.1 22 21.8 13.4 15.0

252 254 230 234 180 282 310 277

603 600 650

5.78

SECTION 5

TABLE 5.3 Critical Properties (continued ) Substance

Tc, K

Deuterium (equilibrium) (normal) Deuterium bromide Deuterium chloride Deuterium hydride Deuterium iodide Deuterium oxide Diborane 1,2-Dibromoethane Dibromomethane Dibromotetrafluoroethane Dibutylamine Dibutyl ether 1,2-Dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene Dichlorodifluoromethane 1,1-Dichloroethane 1,2-Dichloroethane 1,1-Dichloroethylene 1,2-Dichloroethylene Dichlorofluoromethane Dichloromethane 1,2-Dichloropropane Dichlorosilane 1,1-Dichloro-1,2,2,2-tetrafluoroethane 1,2-Dichloro-1,1,2,2-tetrafluoroethane Diethylamine 1,4-Diethylbenzene Diethyl disulfide Diethylene glycol Diethyl ether 3,3-Diethylpentane Diethyl sulfide Difluoroamine (HNF2) cis-Difluorodiazine (N2F2) trans-Difluorodiazine 1,1-Difluoroethane 1,1-Difluoroethylene Dihexyl ether Dihydrogen disulfide Dihydrogen heptasulfide Dihydrogen hexasulfide Dihydrogen octasulfide Dihydrogen pentasulfide Dihydrogen tetrasulfide Dihydrogen trisulfide Diisopropyl ether

38.3 38.4 361.9 328.4 35.8 421.7 644.0 289.0 582.9 583 487.6 596 580 697.3 684 685 385.0 523 561 544 516.5 451.6 510 577 449 418.6 418.9 496.6 657.9 642 681 466.7 610 557 403 272 260 386.6 302.8 657 572 1015 980 1040 930 855 738 500

Pc, atm

Vc, cm3 · mol1

16.28 16.43

60.4 60.3

14.64

62.8

213.8 39.5 70.6 71 34 25 25 40.5 38 39 40.7 50 53

55.6

54.4 51.0 60.0 44 46.1 32.6 32.6 36.6 27.7 46 35.9 26.4 39.1 93 70 55 44.4 44.0 18 58.3 33 36 32 38.4 43.1 50.6 28.4

329 517 500 360 359 372 217 240 220

197 193 226 294 293 301 480 316 280 318

181 154 720

385

5.79

THERMODYNAMIC PROPERTIES

TABLE 5.3 Critical Properties (continued ) Vc, cm3 · mol1

Substance

Tc, K

Pc, atm

1,2-Dimethoxyethane Dimethoxymethane Dimethylamine N,N-Dimethylaniline 2,2-Dimethylbutane 2,3-Dimethylbutane 2,3-Dimethyl-1-butene 2,3-Dimethyl-2-butene 3,3-Dimethyl-1-butene 1,1-Dimethylcyclohexane cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane cis-1,3-Dimethylcyclohexane trans-1,3-Dimethylcyclohexane 1,1-Dimethylcyclopentane cis-1,2-Dimethylcyclopentane trans-1,2-Dimethylcyclopentane Dimethyl ether 2,2-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane Dimethyl oxalate 2,2-Dimethylpentane 2,3-Dimethylpentane 2,4-Dimethylpentane 3,3-Dimethylpentane 2,2-Dimethylpropane 2,2-Dimethyl-1-propanol 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,5-Dimethylpyridine 2,6-Dimethylpyridine 3,4-Dimethylpyridine 3,5-Dimethylpyridine N,N-Dimethyl-o-toluidine 1,4-Dioxane Diphenyl ether Diphenylmethane Dipropylamine Dodecane 1-Dodecanol 1-Dodecene Dodecylcyclopentane

536 497 437.6 687 488.7 499.9 501 524 490 591 606 596 591 598 547 564.8 553.2 400.0 549.8 563.4 553.5 550.0 562.0 568.8 628 520.4 537.3 519.7 536.3 433.8 549 655.4 644.2 644 623.7 683.8 667.2 668 587 766 767 550 658.3 679 657 750

38.2

271

52.4 35.8 30.4 30.9 32.0 33.2 32.1 29.3 29.3 29.3 29.3 29.3 34.0 34.0 34.0 53.0 25.0 25.9 25.2 24.5 26.2 26.6 39.2 27.4 28.7 27.0 29.1 31.6 39

187

30.8 51.4 31 29.4 31 18.0 19 18.3 12.8

Ethane Ethanethiol

305.4 498.6

48.2 54.2

359 358 343 351 340 416

360 368 362 178 478 468 472 482 443 466 416 393 418 414 303 319

238

407 713 718

148 207

5.80

SECTION 5

TABLE 5.3 Critical Properties (continued ) Vc, cm3 · mol1

Substance

Tc, K

Pc, atm

Ethanol Ethoxybenzene Ethyl acetate Ethyl acetoacetate Ethyl acrylate Ethylamine Ethylbenzene Ethyl benzoate 2-Ethyl-1-butanol Ethyl butyrate Ethyl crotonate Ethylcyclohexane Ethylcyclopentane Ethylene Ethylenediamine Ethylene glycol Ethylene oxide Ethyl formate 3-Ethylhexane 2-Ethylhexanol 2-Ethyl-1-methylbenzene 3-Ethyl-1-methylbenzene 4-Ethyl-1-methylbenzene Ethyl 3-methylbutyrate 1-Ethyl-1-methylcyclopentane Ethyl methyl ether Ethyl methyl ketone 3-Ethyl-2-methylpentane 3-Ethyl-2-methylpentane 3-Ethyl-3-methylpentane Ethyl-2-methylpropanoate Ethyl methyl sulfide 3-Ethylpentane o-Ethylphenol m-Ethylphenol p-Ethylphenol Ethylpropanoate Ethyl propyl ether o-Ethyltoluene m-Ethyltoluene p-Ethyltoluene Ethyl vinyl ether

516.2 647.1 523.2 673 552 456 617.1 697 418.8 565.9 599 609 369.5 282.4 592.9 645 469 508.4 565.4 613 651 637 640 588.0 592 437.8 535.6 567.0 576.5 576.4 553 533 540.6 703.0 716.4 716.4 546.0 500.6 653 636 636 475

63.0 33.8 37.8

167

37.0 55.5 35.6 32

320 178 374 451

30.2

395

29.9 33.5 49.7 62.1 76 71.0 46.8 25.7 27.2 30.0 28.0 29.0

450 375 129 206 186 140 229 455 494 460 490 470

33.2 32.1 31 31 31 40.2

345 244 461 461 461 260

Fluorine Fluorobenzene Fluoroethane Fluoromethane Fluorotrichloromethane Formaldehyde

144.3 560.1 375.3 317.8 471.1 408

51.5 44.9 49.6 58.0 43.2 65

66.2 271 169 124 248

29.5 43.4 41.0 26.7 27.7 27.7 30 42 28.5

286

221 267 443 455 455 410 416

5.81

THERMODYNAMIC PROPERTIES

TABLE 5.3 Critical Properties (continued ) Vc, cm3 · mol1

Substance

Tc, K

Pc, atm

Formic acid Furan

580 490.2

54.3

218

Germanium tetrachloride Glycerol

550.0 726

38 66

330 255

Hafnium tetrabromide Hafnium tetrachloride Hafnium tetraiodide Helium-3 Helium-4 Heptadecane 1-Heptadecanol Heptane 1-Heptanol 1-Heptene Heptylcyclopentane Hexadecane 1-Hexadecene Hexadecylcyclopentane 1,5-Hexadiene Hexafluoroethane Hexamethylbenzene Hexane 1-Hexanol 1-Hexene cis-2-Hexene trans-2-Hexene cis-3-Hexene trans-3-Hexene Hexylcyclopentane Hydrazine Hydrogen (equilibrium) (normal) Hydrogen bromide Hydrogen chloride Hydrogen cyanide Hydrogen deuteride, see Deuterium hydride Hydrogen fluoride Hydrogen iodide Hydrogen selenide Hydrogen sulfide

746 723 916 3.30 5.19 733 736 540.2 633 537.2 679 717 717 791 507 292.8 767 507.4 610 504.3 518 516 517 519.9 660.1 653

Icosane 1-Icosanol Iodine Iodobenzene Iodomethane

57.0 1.167 2.24 13 14 27.0 30 28 19.2 14 13.2 9.6 34 29.4

415 304 528 73.2 57.3 1000 432 435 440

328 223.7

29.3 40 31.3 32.4 32.3 32.4 32.1 21.1 145

370 381 350 351 351 350 350 96.1

32.9 33.2 363.2 324.6 456.8

12.77 12.8 84.4 82.0 53.2

65.4 65.0 100.0 81.0 139

461 424.0 411 373.2

64 82.0 88 88.2

69 131 98.5

767 770 819 721 528

11.0 12.0 115 44.6 65

155 351 190

5.82

SECTION 5

TABLE 5.3 Critical Properties (continued ) Vc, cm3 · mol1

Substance

Tc, K

Pc, atm

Isobutyl acetate Isobutylamine Isobutylbenzene Isobutyl butyrate lsobutylcyclohexane Isobutyl formate Isobutyl 3-methylbutyrate Isobutyl propanoate Isobutyric acid Isopropylamine lsopropylbenzene lsopropylcyclohexane Isopropylcyclopentane 2-Isopropyl-1-methylbenzene 3-Isopropyl-l-methylbenzene 4-Isopropyl-1-methylbenzene Isoquinoline Isoxazole

561 516 650 611 659 551 621 592 609 476 631.0 640 601 670 666 653 803 552.0

30 42 31

414 284 480

30.8 38.3

350

40 50 31.7 28 29.6 28.6 290 27.9

292 229 428

Ketene Krypton

380 209.4

64 54.3

145 91.2

Mercury Methane Methanethiol Methanol Methoxybenzene (anisole) Methyl acetate Methyl acrylate Methylamine N-Methylaniline Methyl benzoate 2-Methyl-1,3-butadiene 3-Methyl-1,2-butadiene 2-Methylbutane 2-Methyl-1-butanol 3-Methyl-1-butanol 2-Methyl-2-butanol 3-Methyl-2-butanone 2-Methyl-1-butene 2-Methyl-2-butene 3-Methyl-1-butene Methyl butyrate 3-Methylbutyric acid Methylcyclohexane Methylcyclopentane N-Methylethylamine Methyl formate 2-Methylheptane

1173 190.6 470.0 512.6 641 506.8 536 430 701 692 484 496 460.4 571 579.5 545 553.4 465 470 450 554.4 634 572.1 532.7 496.6 487.2 559.6

180 45.4 71.4 79.9 41.2 46.3 42 73.6 51.3 36 38.0 40.6 33.3 38 38 39 38.0 34.0 34.0 34.7 34.3 34.3 37.4 36.6 59.2 24.5

99.0 145 118 228 265 140 396 276 267 306 322 329 319 310 294 318 300 340 368 319 243 172 488

5.83

THERMODYNAMIC PROPERTIES

TABLE 5.3 Critical Properties (continued ) Vc, cm3 · mol1

Substance

Tc, K

Pc, atm

3-Methylheptane 4-Methylheptane 2-Methylhexane 3-Methylhexane Methylhydrazine Methyl isobutyrate Methyl isocyanate 1-Methylnaphthalene 2-Methylnaphthalene 2-Methylpentane 3-Methylpentane 2-Methyl-2,4-pentanediol 4-Methyl-2-pentanone 2-Methyl-2-pentene cis-3-Methyl-2-pentene trans-3-Methyl-2-pentene cis-4-Methyl-2-pentene trans-4-Methyl-2-pentene Methyl phenyl ether 2-Methylpropanal 2-Methylpropane Methyl propanoate 2-Methyl-1-propanol (isobutyl alcohol) 2-Methyl-2-propanol 2-Methylpropene 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine -Methylstyrene Methyl vinyl ether Morpholine

563.6 561.7 530.3 535.2 567 540.8 491 772 761 497.5 504.4 678 571 518 518 521 490 493 641 513 408.1 530.6 547.7 506.2 417.9 621 645 646 654 436 618

25.1 25.1 27.0 27.8 79.3 33.9 55 35.2 34.6 29.7 30.8 33.9 32.3 32.4 32.4 32.3 30 30 41.2 41 36.0 39.5 42.4 39.2 39.5

274 263 282 273 275 239

44 33.6 47 54

311 397 205 253

Naphthalene Neon Niobium pentabromide Niobium pentachloride Niobium pentafluoride Nitric oxide Nitrobenzene Nitrogen-14 Nitrogen-15 Nitrogen dioxide (equilibrium) Nitrogen trifluoride Nitromethane Nitrosyl chloride Nitrous oxide Nitryl fluoride Nonadecane Nonane 1-Nonanol

748.4 44.4 1010 807 737 180 732 126.2 126.3 431.4 234.0 588 440 309.6 349.4 756 594.6 677

40.0 27.2

410 41.7 469 400 155 58

62 64 33.5 33.5 100 44.7 62.3 90 71.5 11.0 22.8

464 476 421 404 271 339 445 462 367 367 371 351 351 350 360 360

89.5 90.4 170 173 139 97.4

548 546

5.84

SECTION 5

TABLE 5.3 Critical Properties (continued ) Substance

Tc, K

Pc, atm

1-Nonene Nonylcyclopentane

592 710.5

23.1 16.3

Octadecane 1-Octadecanol 1-Octadecene Octane 1-Octanol 2-Octanol 1-Octene trans-2-Octene Octylcyclopentane Oxygen Oxygen difluoride Ozone

745 747 739 568.8 658 637 566.6 580 694 154.6 215.2 161.3

11.9 14 11.2 24.5 34 27 25.9 27.3 17.7 49.8 48.9 55.0

Paraldehyde Pentachloroethane Pentadecane 1-Pentadecene Pentadecylcyclopentane 1,2-Pentadiene trans-1,3-Pentadiene 1,4-Pentadiene Pentafluorobenzene 1,1,2H-Pentafluoropropane Pentanal Pentane Pentanoic acid 1-Pentanol 2-Pentanone 3-Pentanone 1-Pentene cis-2-Pentene trans-2-Pentene Pentyl formate 1-Pentyne Perchloryl fluoride Perfluoroacetone Perfluorobenzene Perfluorobutane Perfluoro-(2-butyltetrahydrofuran) Perfluorocyclobutane Perfluorocyclohexane Perfluorocyclohexene Perfluorodecene Perfluoroethane Perfluoroheptane Perfluoroheptene Perfluorohexane

563 646.1 707 704 780 503 496 478 532.0 380.11 554 469.6 651 586 564.0 561.0 464.7 476 475 576 493.4 368.4 357.3 516.7 386.4 500.3 388.4 457.2 461.8 542.3 292.8 474.8 478.1 451.7

15 14.4 10.1 40.2 39.4 37.4 34.7 31.0 35 33.3 38 38 38.4 36.9 40.0 36.0 36.1 40 53.0 28.0 32.6 22.9 15.9 27.41 24

Vc, cm3 · mol1 580

492 490 494 464

73.4 97.7 88.9

880

276 275 276 273 333 304 340 326 301 336 300 300 300 278 161

378 588 260

14.3 29.4 16.0

223.7 664

18.8

442

5.85

THERMODYNAMIC PROPERTIES

TABLE 5.3 Critical Properties (continued ) Substance

Tc, K

Perfluorohexene Perfluoromethylcyclohexane Perfluoronaphthalene Perfluorononane Perfluorooctane Perfluoropentane Perfluoropropane Phenanthrene Phenetole Phenol Phosgene Phosphine Phosphonium chloride Phosphorus bromide difluoride Phosphorus chloride difluoride Phosphorus dibromide fluoride Phosphorus dichloride fluoride Phosphorus pentachloride Phosphorus trichloride Phosphorus trifluoride Phosphoryl chloride difluoride Phosphoryl trichloride Phosphoryl trifluoride Phthalic anhydride Piperidine Propadiene Propane 1,2-Propanediol 1,3-Propanediol Propanoic acid 1-Propanol 2-Propanol 2-Propenal Propionaldehyde Propionitrile Propyl acetate Propylamine Propylbenzene Propylcyclopentane Propylcyclohexane Propylene Propylene oxide Propyl formate Propyl propanoate 1-Propyne Pyridine Pyrrole Pyrrolidine

454.3 486.8 673.1 524.0 502 422 345.1 878 647 694.2 455 324.4 322.2 386 362.32 527 463.0 645 563 271.2 423.8 602 346.5 810 594.0 393 369.8 625 658 612 536.7 508.3 506 496 564.4 549.4 497.0 638.3 603 639 365.0 482.2 538.0 578 402.4 620.0 639.6 568.6

Pc, atm

Vc, cm3 · mol1

23 15.4 16.4 20.1 26.5 33.8 60.5 56 64.5 72.7

299

229 190

44.6 49.3 260 42.7 43.4 41.8 47 47 54.0 41.9 60 59 53.0 51.0 47.0 51 47 41.3 23.9 46.8 31.6 29.6 27.7 45.6 48.6 40.1 55.5 55.6 56 55.4

368 289 162 203 237 241 230 218.5 220 223 230 345 233 440 425 181 186 285 164 254 249

5.86

SECTION 5

TABLE 5.3 Critical Properties (continued ) Substance

Tc, K

Quinoline

794.4

Radon Rhenium(VII) oxide

376.9 942

Selenium Silane Silicon chloride trifluoride Silicon tetrachloride Silicon tetrafluoride Silicon trichlorofluoride Styrene Sulfur Sulfur dioxide Sulfur hexafluoride Sulfur tetrafluoride Sulfur trioxide

1766 269.6 307.6 507 259.1 438.5 647 1314 430.8 318.7 364.0 491.0

Tantalum pentabromide Tantalum pentachloride o-Terphenyl m-Terphenyl p-Terphenyl 1,1,2,2-Tetrachloro-1,2-difluoroethane 1,1,2,2-Tetrachloroethane Tetrachloroethylene Tetradecane 1-Tetradecene Tetradecylcyclopentane Tetrafluoroethylene Tetrafluorohydrazine Tetrahydrofuran 1,2,3,4-Tetrahydronaphthalene Tetrahydrothiophene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane 2,2,3,3-Tetramethylhexane 2,2,5,5-Tetramethylhexane 2,2,3,3-Tetramethylpentane 2,2,3,4-Tetramethylpentane 2,2,4,4-Tetramethylpentane 2,3,3,4-Tetramethylpentane 2-Thiapropane Thiophene Thymol Tin(IV) chloride Titanium tetrachloride Toluene o-Toluidine m-Toludine p-Toluidine Toluonitrile

974 767 891.0 924.8 926.0 551 661.1 620 694 689 772 306.4 309.4 540.2 719 631.9 675 567.8 623.1 581.5 607.6 592.7 574.7 607.6 503.1 579.4 698 591.8 638 591.7 694 709 667 723

Pc, atm

62

47.8 34.2 37 36.7 35.3 39.4

Vc, cm3 · mol1

139 334

326

77.8 37.1

122 198

81

130

38.5 34.6 32.8 34

461 400 769 784 779 370

44 16 15.4 11.1 38.9 37 51.2 34.7

290 830

29 28.3 24.8 21.6 27.0 25.7 24.5 26.8 54.6 56.2

480 461

201 219

37.0 46 40.6 37 41

351 340 316 343 343

175 224

5.87

THERMODYNAMIC PROPERTIES

TABLE 5.3 Critical Properties (continued ) Pc, atm

Vc, cm3 · mol1

Substance

Tc, K

Tributylamine 1,1,2-Trichloroethane Trichloroethylene Trichlorofluoromethane 1,2,3-Trichloropropane 1,2,2-Trichloro-1,1,2-trifluoroethane Tridecane 1-Tridecene Tridecylcyclopentane Triethanolamine Triethylamine Trifluoroacetic acid 1,1,1-Trifluoroethane Trifluoromethane Trimethylamine 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene 2,2,3-Trimethylbutane 2,2,3-Trimethyl-1-butene Trimethylchlorosilane 1,1,2-Trimethylcyclopentane 1,1,3-Trimethylcyclopentane cis,cis,trans1,2, 4-Trimethylcyclopentane cis,trans,cis1,2, 4-Trimethylcyclopentane 3,3,5-Trimethylheptane 2,2,3-Trimethylhexane 2,2,4-Trimethylhexane 2,2,5-Trimethylhexane 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane 2,3,4-Trimethylpentane 2,2,4-Trimethyl-1,3-pentanediol

643 602 571 471.2 651 487.2 675.8 674 761 787.4 535 491.3 346.2 298.89 433.2 664.5 649.1 637.3 531.1 533 497.7 579.5 569.5

18 41 48.5 43.5 39 33.7 17.0 16.8 11.9 24.2 30 32.2 37.1 47.7 40.2 34.1 31.9 30.9 29.2 28.6 31.6 29.0 27.9

579

28.4

571 609.6 588 573.7 567.9 563.4 543.9 573.5 566.3 671

27.7 22.9 24.6 23.4 23.0 26.9 25.3 27.8 26.9 25.6

1H-Undecafluoropentane Undecane 1-Undecene Uranium hexafluoride

443.9 638.8 637 505.8

19.4 19.7 45.5

250

Vinyl acetate Vinyl chloride Vinyl fluoride Vinyl formate

525 429.7 327.8 475

43 55.3 51.7 57

265 169 114 210

Water

647.3

217.6

56.0

Xenon o-Xylene

289.7 630.2

57.6 36.8

118 369

294 256 248 348 304 780

390 204 221 133.3 254 430 430 433 398 400

519 436 468 455 461 364.6

660

5.88

SECTION 5

TABLE 5.3 Critical Properties (continued ) Vc, cm3 · mol1

Substance

Tc, K

Pc, atm

m-Xylene p-Xylene 2,3-Xylenol 2,4-Xylenol 2,5-Xylenol 2,6-Xylenol 3,4-Xylenol 3,5-Xylenol

617.0 616.2 722.6 707.6 723.0 700.9 729.8 715.6

35.0 347 48 43 48 42 49 36

376 379 470 509 470 509 552 611

Zirconium tetrabromide Zirconium tetrachloride Zirconium tetraiodide

805 778 960

56.9

415 319 528

Zirconium tetraiodide

960

528

Estimation of Critical Properties When the critical properties are unavailable, they may be estimated employing structural contributions to estimate Tc, Pc, and Vc. Lydersen’s critical-property increments* provide good estimates for Tc and Pc; Vetere’s group contributions† yield reasonable estimates for Vc. The units employed are kelvins, atmospheres, and cubic centimeters per mole. Typical errors in estimated values are less than 2% for Tc but may rise up to 5% for higher-molecular-weight (greater than 100) nonpolar materials; errors are uncertain for molecules with multifunctional polar groups. Errors for estimated values of Pc and Vc are about double those for Tc. The relations are 1 Tc  Tb 0.567  T   T2





Pc  M0.34 

 





2

M  

1.029

Vc33

i

v

i

where Tb is the normal boiling point and M is the molular weight. Group contributions are listed in Table 5.4. TABLE 5.4 Group Contributions for the Estimation of Critical Properties There are no increments for hydrogen. All bonds shown as free are connected with atoms other than hydrogen. Values in parentheses are based upon very few experimental values.

Group

T, K

P, atm

V, cm3 · mol1

Nonring increments ˆ CH3, ˆ CH2 ˆ

0.020

0.227

3.360 (linear chain) 2.888 (side chain)

* A. L. Lydersen, Univ. Wisconsin Coll. Eng., Eng. Exp. Stn, Rep 3, Madison, April 1955. † A Vetere, cited in R. C. Reid, J. M. Prausnitz, and T. K Sherwood, The Properties of Gases and Liquids, 3d ed., McGraw-Hill, New York, 1977, p. 17.

5.89

THERMODYNAMIC PROPERTIES

TABLE 5.4 Group Contributions for the Estimation of Critical Properties (continued ) Group

T, K

P, atm

| — CH |

0.012

0.210

ˆCˆ

0.0

0.210

¨ CH2 , ¨ CH

0.018

0.198

2.940

¨ Cˆ

0.0

0.198

2.940

, cm3 · mol1

V

3.360 (linear chain) 2.888 (side chain) 3.360 (linear chain) 2.888 (side chain)

¨C¨

0.0

0.198

2.908

˜ CH, ˜ C ˆ ˆOˆ aC ¨ O aNH aN ˆ ˆSˆ

0.005 0.021 0.040 0.031 0.014 0.015

0.153 0.16 0.29 0.135 0.17 0.27

2.648 1.075 1.765 2.333 1.793 0.591

Ring increments 0.013

0.184

2.813

ˆC ˆ

0.012 (0.007)

0.192 (0.154)

2.813 2.813

¨ CH, ¨ C, ¨ C¨ ˆOˆ aC ¨ O aNH aN ˆ ˆSˆ

0.011 (0.014) (0.033) (0.024) (0.007) (0.008)

0.154 (0.12) (0.2) (0.09) (0.13) (0.24)

2.538 0.790 1.500 1.736 1.883 0.911

ˆ CH2 ˆ ˆ CH ˆ

General substituents ˆF ˆ Cl ˆ Br ˆI ˆ OH Alcohols Phenols

0.018 0.017 0.010 0.012

0.224 0.320 (0.50) (0.83)

0.770 1.237 0.899 0.702

0.082 0.031

0.06 (0.02)

0.704 1.553

HC ¨ O (aldehyde) ˆ COOH ˆ COO ˆ (ester) ˆ NH2 ˆ CN ˆ NO2 ˆ SH

0.048 0.085 0.047 0.031 (0.060) (0.055) 0.015

0.33 (0.4) 0.47 0.095 (0.36) (0.42) 0.27

2.333 1.652 1.607 2.184 2.784 1.559 1.537

ˆ Si ˆ

0.03

(0.54)

SECTION 6

SPECTROSCOPY

ULTRAVIOLET-VISIBLE SPECTROSCOPY . . . . . . . . . . . . . Table 6.1 Electronic Absorption Bands for Representative Chromophores . . . . . . . . . . . . . . . . . . . . . Table 6.2 Ultraviolet Cutoffs of Spectrograde Solvents . . . . . Table 6.3 Absorption Wavelength of Dienes . . . . . . . . . . Table 6.4 Absorption Wavelength of Enones and Dienones . . Table 6.5 Solvent Correction for UV–VIS Spectroscopy . . . . Table 6.6 Primary Band of Substituted Benzene and Heteroaromatics . . . . . . . . . . . . . . . . . . . . Table 6.7 Wavelength Calculation of the Principal Band of Substituted Benzene Derivatives . . . . . . . . . . . PHOTOLUMINESCENCE . . . . . . . . . . . . . . . . . . . . . . . Table 6.8 Fluorescence Spectroscopy Data of Some Organic Compounds . . . . . . . . . . . . . . . . . . . . . . Table 6.9 Fluorescence Quantum Yield Values . . . . . . . . . Table 6.10 Phosphorescence Spectroscopy of Some Organic Compounds . . . . . . . . . . . . . . . . . . . . . . INFRARED SPECTROSCOPY . . . . . . . . . . . . . . . . . . . . . Table 6.11 Absorption Frequencies of Single Bonds to Hydrogen Table 6.12 Absorption Frequencies of Triple Bonds . . . . . . . Table 6.13 Absorption Frequencies of Cumulated Double Bonds Table 6.14 Absorption Frequencies of Carbonyl Bonds . . . . . Table 6.15 Absorption Frequencies of Other Double Bonds . . . Table 6.16 Absorption Frequencies of Aromatic Bonds . . . . . Table 6.17 Absorption Frequencies of Miscellaneous Bands . . Table 6.18 Absorption Frequencies in the Near Infrared . . . . . Table 6.19 Infrared Transmitting Materials . . . . . . . . . . . . Table 6.20 Infrared Transmission Characteristics of Selected Solvents . . . . . . . . . . . . . . . . . . . RAMAN SPECTROSCOPY SPECTROSCOPY . . . . . . . . . . . . Table 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon . . . . . . . . . . . . . . . . . Table 6.22 Raman Frequencies of Triple Bonds . . . . . . . . . Table 6.23 Raman Frequencies of Cumulated Double Bonds . . Table 6.24 Raman Frequencies of Carbonyl Bonds . . . . . . . Table 6.25 Raman Frequencies of Other Double Bonds . . . . . Table 6.26 Raman Frequencies of Aromatic Compounds . . . . Table 6.27 Raman Frequencies of Sulfur Compounds . . . . . . Table 6.28 Raman Frequencies of Ethers . . . . . . . . . . . . . Table 6.29 Raman Frequencies of Halogen Compounds . . . . . Table 6.30 Raman Frequencies of Miscellaneous Compounds . . NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY . . . . . Table 6.31 Nuclear Properties of the Elements . . . . . . . . . .

6.1

.

6.3

. . . . .

6.5 6.6 6.7 6.7 6.8

.

6.9

. .

6.9 6.10

. .

6.11 6.17

. . . . . . . . . . .

6.17 6.21 6.21 6.28 6.29 6.31 6.35 6.39 6.40 6.47 6.49

. .

6.51 6.54

. . . . . . . . . . . .

6.54 6.59 6.60 6.61 6.63 6.66 6.67 6.69 6.70 6.71 6.71 6.73

6.2

SECTION 6

Table 6.32 Proton Chemical Shifts of Reference compounds Relative to Tetramethylsilane . . . . . . . . . . . . Table 6.33 Common NMR Solvents . . . . . . . . . . . . . . Table 6.34 Proton chemical shifts . . . . . . . . . . . . . . . . Table 6.35 Estimation of Chemical Shift for Proton of ˆ CH2 ˆ and aCH ˆ Groups . . . . . . . . . Table 6.36 Estimation of Chemical Shift of Proton Attached to a Double Bond . . . . . . . . . . . . . Table 6.37 Chemical Shifts in Monosubstituted Benzene . . . Table 6.38 Proton Spin Coupling Constants . . . . . . . . . . Table 6.39 Carbon-13 Chemical Shifts . . . . . . . . . . . . . Table 6.40 Estimation of Chemical Shifts of Alkane Carbons . . . . . . . . . . . . . . . . . . . Table 6.41 Effect of Substituent Groups on Alkyl Chemical Shifts . . . . . . . . . . . . . . . . . . . Table 6.42 Estimation of Chemical Shift of Carbon Attached to a Double Bond . . . . . . . . . Table 6.43 Carbon-13 Chemical Shifts in Substituted Benzenes Table 6.44 Carbon-13 Chemical Shifts in Substituted Pyridines . . . . . . . . . . . . . . . . . . . . . . . Table 6.45 Carbon-13 Chemical Shifts of Carbonyl Group . . Table 6.46 One-Bond Carbon–Hydrogen Spin Coupling Constants . . . . . . . . . . . . . . . . . . . . . . Table 6.47 Two-Bond Carbon–Hydrogen Spin Coupling Constants . . . . . . . . . . . . . . . . . . . . . . Table 6.48 Carbon–Carbon Spin Coupling Constants . . . . . Table 6.49 Carbon–Fluorine Spin Coupling Constants . . . . . Table 6.50 Carbon-13 Chemical Shifts of Deuterated Solvents . . . . . . . . . . . . . . . . . . . . . . . Table 6.51 Carbon-13 Spin Coupling Constants with Various Nuclei . . . . . . . . . . . . . . . . . . . . Table 6.52 Boron-11 Chemical Shifts . . . . . . . . . . . . . Table 6.53 Nitrogen-15 (or Nitrogen-14) Chemical Shifts . . . Table 6.54 Nitrogen-15 Chemical Shifts in Monosubstituted Pyridine . . . . . . . . . . . . . . . . . . . . . . . Table 6.55 Nitrogen-15 Chemical Shifts for Standards . . . . . Table 6.56 Nitrogen-15 to Hydrogen-1 Spin Coupling Constants . . . . . . . . . . . . . . . . . . . . . . Table 6.57 Nitrogen-15 to Carbon-13 Spin Coupling Constants . . . . . . . . . . . . . . . . . . . . . . Table 6.58 Nitrogen-15 to Fluorine-19 Spin Coupling Constants . . . . . . . . . . . . . . . . . Table 6.59 Fluorine-19 Chemical Shifts . . . . . . . . . . . . Table 6.60 Fluorine-19 Chemical Shifts for Standards . . . . . Table 6.61 Fluorine-19 to Fluorine-19 Spin Coupling Constants Table 6.62 Silicon-29 Chemical Shifts . . . . . . . . . . . . . Table 6.63 Phosphorus-31 Chemical Shifts . . . . . . . . . . . Table 6.64 Phosphorus-31 Spin Coupling Constants . . . . . . ELECTRON SPIN RESONANCE . . . . . . . . . . . . . . . . . . Table 6.65 Spin–Spin Coupling (Hyperfine Splitting Constants) . . . . . . . . . . . . . . . . IONIZATION POTENTIALS . . . . . . . . . . . . . . . . . . . . . Table 6.66A Ionization Potentials of Molecular Species . . . Table 6.66B Alphabetical Listing of Ionization Potentials of Molecular Species . . . . . . . . . Table 6.67 Ionization Potentials of Radical Species . . . . . X-RAY DIFFRACTION . . . . . . . . . . . . . . . . . . . . . . . .

. . . . . .

6.74 6.75 6.76

. .

6.79

. . . .

. . . .

6.80 6.81 6.82 6.83

. .

6.86

. .

6.87

. . . .

6.88 6.89

. . . .

6.90 6.91

. .

6.92

. . . . . .

6.93 6.93 6.94

. .

6.95

. . . . . .

6.96 6.96 6.97

. . . .

6.100 6.101

. .

6.101

. .

6.102

. . . . . . . . . . . . . . .

6.102 6.103 6.104 6.104 6.104 6.105 6.109 6.110

. . . . . .

6.111 6.113 6.113

. . . . . .

6.119 6.121 6.121

6.3

SPECTROSCOPY

For more than half a century, spectroscopy has been the key structural tool for organic chemistry and biochemistry. This remains the case today although the availability of enhanced methods of X-ray analysis has somewhat altered the balance in both disciplines. A vast array of specialized texts are available that survey spectroscopic techniques in general or individual methods in particular. It would be folly to try to duplicate those efforts here. A brief overview of the methods may prove helpful and serve as a reminder for the practitioner who consults this handbook.

ULTRAVIOLET–VISIBLE SPECTROSCOPY Generally, spectroscopic methods involve the absorption of radiation at certain wavelengths (and therefore certain energies) by molecules. For the techniques of ultraviolet–visible (UV–VIS) and infrared spectroscopy, there is an inverse proportionality between the amount of energy absorbed and the structural information that is revealed. The UV–VIS wavelength range is generally considered to be 200–800 nm. At the lower end, oxygen absorbs energy and the lowest end of the range is called the “vacuum UV.” Relatively limited structural information may be obtained from the typically broad bands that are observed. Even so, the electronic transitions that are observed are sensitive to structure. Individual absorbing groups or chromophores absorb light at a characteristic wavelength. The absorption usually shifts when two or more chromophores are linked or in conjugation. The UV–VIS technique may be used quantitatively by application of Beer’s law:   abc. In this relationship,  is the extinction coefficient that is characteristic of a given compound. The values a and c represent absorption and concentration, respectively. The

1.0

Absorbance

0.8

0.6

0.4

0.2

0.0 200 UV Sprectrum of Napthalene.

300 nm

400

6.4

SECTION 6

variable b is the pathlength of light through the sample, usually 1 cm. If the extinction coefficient is known, the measured absorption will give the compound’s concentration. The spectrum of naphthalene is shown above. Its broad bands reflect the absorption of energy by the extended pi-electron system. The tables in this section present the essential data required for interpretation of UV–VIS spectra. Table 6.1 lists representative chromophores. These are identified by max, the maximum height of any given peak, and by max, the extinction coefficient at the maximum wavelength. Both the wavelength and absorption intensity are characteristic of individual chromophores. Table 6.2 lists the ultraviolet cutoff for a variety of solvents commonly used in UV–VIS spectroscopy. The solvent chosen must dissolve the sample, yet be relatively transparent in the spectral region of interest. Typically, very low concentrations of sample will be present in the solvent. It is therefore important to avoid solvents that have even weak absorptions near the solute’s bands of interest. Methanol and ethanol are two of the most commonly used solvents. Care must be exercised when using the latter that no benzene (an azeotropic drying agent) is present as this will alter the solvent’s transparency. Normally, this will not be a problem in spectral grade solvents. Tables 6.3–6.5 record data developed to undertake structural analysis in systems possessing chromophores that are conjugated or otherwise interact with each other. Chromophores within a molecule interact when linked directly to each other or when they are forced into proximity owing to structural constraints. Certain combinations of functional groups comprise chromophoric systems that exhibit characteristic absorption bands. In the era when UV–VIS was one of the principal spectral methods available to the organic chemist, sets of empirical rules were developed to extract as much information as possible from the spectra. The correlations referred to as Woodward’s rules or the Woodward–Fieser rules, enable the absorption maxima of dienes (Table 6.3) and enones and dienones (Table 6.4) to be predicted. When this method is applied, wavelength increments correlated to structural features are added to the respective base values (absorption wavelength of parent compound). The data refer to spectra determined in methanol or ethanol. When other solvents are used, a numerical correction must be applied. These corrections are recorded in Table 6.5. The benzene ring is a common structural element in organic chemistry. It is rigid and substituents are arranged in a fixed orientation. Shifts in the wavelength are expected for substituents that can interact electronically with the aromatic ring. Typically, shifts to longer wavelength (and intensification of the absorption band) are observed for any ring substitution. In the absence of conjugation, the shifts are small. Also, interposition of a single methylene group, or meta orientation within the aromatic ring, is sufficient to insulate chromophores almost completely from each other. With electron-withdrawing substituents, practically no change in the maximum position is observed. Directly conjugated groups may produce quite large spectral shifts. Examples include double and triple bonds and carbonyl groups. The spectra of heteroaromatics are related to their isocyclic analogs, but only in a general way. As with benzene, the magnitude of substituent shifts can be estimated, but tautomeric possibilities may invalidate the empirical method. Table 6.6 records data for substituents bonded directly to a benzene ring. When electronically complementary groups are situated para to each other in disubstituted benzenes, there is a more pronounced shift to a longer wavelength than would be expected from the additive effect due to the extension of the chromophore from the electron-donating group through the ring to the electron-withdrawing group. When the para groups are not complementary, or when the groups are situated ortho or meta to each other, disubstituted benzenes show a more or less additive effect of the two substituents on the wavelength maximum. Calculation of the principal band of selected substituted benzenes is illustrated in Table 6.7.

6.5

SPECTROSCOPY

TABLE 6.1 Electronic Absorption Bands for Representative Chromophores Chromophore

System

Acetylene (ethynyl) Aldehyde

ˆC˜Cˆ ˆ CHO

Amine Azido Azo Bromide Carbonyl

ˆ NH2 aC ¨ N ˆ ˆN¨Nˆ ˆ Br aC ¨ O

Carboxyl Disulfide

ˆ COOH ˆSˆSˆ

Ester Ether Ethylene Iodide Nitrate ester Nitrile Nitrite ester

ˆ COOR ˆOˆ ˆC¨Cˆ ˆI ˆ ONO2 ˆC˜N ˆ ONO

Nitro Nitroso Oxime Sulfone Sulfoxide Thiocarbonyl Thioether

ˆ NO2 ˆ NO ˆ NOH ˆ SO2 ˆ aS ¨ O (aS→O) aC ¨ S ˆSˆ

Thiol

ˆ SH ˆ (C ¨ C)2 ˆ (acyclic) ˆ (C ¨ C)3 ˆ ˆ (C ¨ C)4 ˆ ˆ (C ¨ C)5 ˆ ˆ (C ¨ C)2 ˆ (alicyclic) C¨CˆC˜C C¨CˆC¨N C¨CˆC¨O C ¨ C ˆ NO2

Benzene

Diphenyl Naphthalene

Anthracene Phenanthrene

max

max

175–180 210 280–300 195 190 285–400 208 195 270–285 200–210 194 255 205 185 190 260 270 (shoulder) 160 220–230 300–400 210 302 190 180 210 205 194 215 195 210–230 260 300 330 230–260 219 220 210–250 300–350 229 184 204 255 246 222 275 312 252 375 251 292

6 000 strong 11–18 2 800 5 000 3–25 300 1 000 18–30 50–70 5 500 400 50 1 000 8 000 400 12 — 1 000–2 000 10 strong 100 5 000 — 1 500 strong 4 600 1 600 1 400 21 000 35 000 52 000 118 000 3 000–8 000 6 500 23 000 10 000–20 000 weak 9 500 46 700 6 900 170 20 000 112 000 5 600 175 199 000 7 900 66 000 14 000

6.6

SECTION 6

TABLE 6.1 Electronic Absorption Bands for Representative Chromophores (continued) Chromophore

max

System

Naphthacene

272 473 310 585 174 195 257 227 270 314 218 266 317

Pentacene Pyridine

Quinoline

Isoquinoline

max 180 000 12 500 300 000 12 000 80 000 6 000 1 700 37 000 3 600 2 750 80 000 4 000 3 500

TABLE 6.2 Ultraviolet Cutoffs of Spectrograde Solvents Absorbance of 1.00 in a 10.0 mm cell vs. distilled water

Solvent Acetic acid Acetone Acetonitrile Benzene 1-Butanol 2-Butanol Butyl acetate Carbon disulfide Carbon tetrachloride 1-Chlorobutane Chloroform (stabilized with ethanol) Cyclohexane 1,2-Dichloroethane Diethyl ether 1,2-Dimethoxyethane N,N-Dimethylacetamide N,N-Dimethylformamide Dimethylsulfoxide 1,4-Dioxane Ethanol 2-Ethoxyethanol Ethyl acetate Ethylene chloride Glycerol Heptane

Wavelength, nm 260 330 190 280 210 260 254 380 265 220 245 210 226 218 240 268 270 265 215 210 210 255 228 207 197

Solvent Hexadecane Hexane Isobutyl alcohol Methanol 2-Methoxyethanol Methylcyclohexane Methylene chloride Methyl ethyl ketone Methyl isobutyl ketone 2-Methyl-1-propanol N-Methylpyrrolidone Nitromethane Pentane Pentyl acetate 1-Propanol 2-Propanol Pyridine Tetrachloroethylene (stabilized with thymol) Tetrahydrofuran Toluene 1,1,2-Trichloro-1,2,2trifluoroethane 2,2,4-Trimethylpentane o-Xylene Water

Wavelength, nm 200 210 230 210 210 210 235 330 335 230 285 380 210 212 210 210 330 290 220 286 231 215 290 191

6.7

SPECTROSCOPY

TABLE 6.3 Absorption Wavelength of Dienes Heteroannular and acyclic dienes usually display molar absorptivities in the 8 000–20 000 range, whereas homoannular dienes are in the 5 000–8 000 range. Poor correlations are obtained for cross-conjugated polyene systems such as

The correlations presented here are sometimes referred to as Woodward’s rules or the Woodward-Fieser rules. Base value for heteroannular or open chain diene, nm Base value for homoannular diene, nm Increment (in nm) for double bond extending conjugation Alkyl substituent or ring residue Exocyclic double bond Polar groupings: -O-acyl -O-alkyl -S-alkyl -Cl, -Br -N (alkyl)2 Solvent correction (see Table 6.5)

214 253 30 5 5 0 6 30 5 60 Calculated wavelength 

total

TABLE 6.4 Absorption Wavelength of Enones and Dienones  O

C

C


C

O


Base values, nm Acyclic ,-unsaturated ketones Acyclic ,-unsaturated aldehyde Six-membered cyclic ,-unsaturated ketones Five-membered cyclic ,-unsaturated ketones ,-Unsaturated carboxylic acids and esters Increments (in nm) for Double bond extending conjugation: Heteroannular Homoannular Alkyl group or ring residue:   , 

C








C

C

C


C


215 210 215 214 195

30 69 10 12 18

6.8

SECTION 6

TABLE 6.4 Absorption Wavelength of Enones and Dienones (continued) Polar groups: ˆ OH    ˆ O ˆ CO ˆ CH3 and ˆ O ˆ CO ˆ C6H5: , , ,  ˆ OCH3     ˆ S ˆ alkyl,  ˆ Cl   ˆ Br   ˆ N(alkyl)2,  Exocyclic double bond Solvent correction (see Table 6.5)

35 30 50 6 35 30 17 31 85 15 12 25 30 95 5 Calculated wavelength  total

TABLE 6.5 Solvent Correction for UV–VIS spectroscopy Solvent Chloroform Diethyl ether 1,4-Dioxane Ethanol Hexane Methanol Water

Correction, nm 1 11 5 0 11 0 8

6.9

SPECTROSCOPY

TABLE 6.6 Primary Band of Substituted Benzene and Heteroaromatics In methanol Base value: 203.5 nm

Substituent

Wavelength shift, nm

ˆ CH3 ˆ CH ¨ CH2 ˆ C ˜ CH ˆ C6H5 ˆF ˆ Cl ˆ Br ˆI ˆ OH ˆ O ˆ OCH3 ˆ OC6H5 ˆ CHO ˆ CO ˆ CH3 ˆ CO ˆ C6H5

3.0 44.5 44 48 0 6.0 6.5 3.5 7.0 31.5 13.5 51.5 46.0 42.0 48

Heteroaromatic

Base value, nm

Furan Pyrazine Pyrazole Pyridazine

200 257 214 ca 240

Substituent

Wavelength shift, nm

ˆ COOH ˆ COO ˆ CN ˆ NH2 ˆNH 3 ˆ N(CH3)2 ˆ NH ˆ CO ˆ CH3 ˆ NO2 ˆ SH ˆ SO ˆ C6H5 ˆ SO2CH3 ˆ SO2NH2 ˆ CH ¨ CH ˆ C6H5 cis (Z ) trans (E) ˆ CH ¨ CH ˆ COOH, trans

Heteroaromatic Pyridine Pyrimidine Pyrrole Thiophene

25.5 20.5 20.5 26.5 0.5 47.0 38.5 57 32 28 13 14.0 79 92.0 69.5

Base value, nm 257 ca 235 209 231

TABLE 6.7 Wavelength Calculation of the Principal Band of Substituted Benzene Derivatives In ethanol Base value of parent chromophore, nm C6H5COOH or C6H5COO ˆ alkyl C6H5 ˆ CO ˆ alkyl (or aryl) C6H5CHO Increment (in nm) for each substituent on phenyl ring ˆ Alkyl or ring residue o-, mpˆ OH and ˆ O ˆ alkyl o-, mpˆ O omp-

230 246 250

3 10 7 25 11 20 78*

* Value may be decreased markedly by steric hindrance to coplanarity.

6.10

SECTION 6

TABLE 6.7 Wavelength Calculation of the Principal Band of Substituted Benzene Derivatives (continued) ˆ Cl o-, mpˆ Br o-, mpˆ NH2 o-, mpˆ NHCO ˆ CH3 o-, mpˆ NHCH3 pˆ N(CH3)2 o-, mp-

0 10 2 15 13 58 20 45 73 20 85

PHOTOLUMINESCENCE Luminescence processes may be categorized by the excitation method used with any particular luminescent molecule. Photoluminescence is the excitation process that involves the interaction of electromagnetic radiation with photons. The process is termed chemiluminescence when the exciting energy results from a chemical reaction. Any luminescence arising from an organism is referred to as bioluminescence. The most common application of photoluminescence is found in fluorescence spectroscopy. Fluorescence is the immediate release of electromagnetic energy from an excited molecule or release of the energy from the singlet state. If the emitted energy arises from the triplet state or is delayed, the process is referred to as phosphorescence. A fluorescence spectrum is characteristic of a given compound. It is observed as a result of radiative emission of the energy absorbed by the molecule. The observed spectrum does not depend on the wavelength of the exciting light, except that the spectrum will be more intense if irradiation occurs at the absorption maximum. The spectral intensity is called the quantum efficiency and is usually abbreviated as . The quantum yield or quantum efficiency, , which is solvent dependent, is the ratio:   number of quanta emitted/number of quanta absorbed. Approximate values of quantum efficiencies are as follows: naphthalene, ~0.1; anthracene, ~0.3; indole, ~0.5; and fluorescein, ~0.9. An equation similar to Beer’s law applies to fluorescence spectroscopy at dilute concentrations. In its most general form, it is given as F  I0(1  ebc). In this equation, F is the observed fluorescence,  is the quantum efficiency (see above), I0 is the intensity of the incident radiation,  is the molar absorptivity, b is the cell’s path length, and c is the compound’s molar concentration. The appearance of a fluorescence spectrum is reminiscent of a UV–VIS spectrum. The fluorescence spectrum for a 3-substituted indole derivative is shown in Figure 6.1. The

6.11

SPECTROSCOPY

800.0 700 600 500 400

Int

300 200 100 0.4 200.0 FIGURE 6.1

300

400

500 nm

600

700

800.0

Fluorescence Spectrum for a 3-substituted indole derivative.

compound concentration was approximately 105 M in acetonitrile (CH3CN). The sample was irradiated at a wavelength of 283 nm. The abscissa shows the wavelength in nanometers (nm) and the intensity (“int”) is recorded on the ordinate. The maximum emission intensity is observed at 356 nm. The longest wavelength peak (max) is observed at approximately 680 nm. TABLE 6.8 Fluorescence Spectroscopy Data for Selected Organic Compounds

pH

Excitation wavelength, nm

Emission wavelength, nm

Compound

Solvent

Acenaphthene

Pentane

291

341

Acridine

CF3COOH

358

475

N

Adenine

Water

1

280

375

Adenosine

Water

1

285

395

Water

1

285

395

8

295 295

335 345

NH2 N N

N

OH O OH HO

Adenosine triphosphate Adrenalin p-Aminobenzoic acid

Water

6.12

SECTION 6

TABLE 6.8 Fluorescence Spectroscopy Data for Selected Organic Compounds (continued )

Compound Aminopterin HOOC

HOOC H

Solvent

pH

Water

7

Excitation Emission wavelength, nm wavelength, nm 280, 370

460

O H N

NH2 N N

H N N

NH2

1-Aminopyrene

CF3COOH

p-Aminosalicylic acid

Water

11

330, 342

415

300

405

Amobarbital

Water

14

265

410

Anilines (aminobenzenes) Anthracene

Water Pentane

7

280, 291 420

344, 361 430

Anthranilic acid (2-aminobenzoic acid)

Water

7

300

405

Azaindoles

Water

10

290, 299

310, 347

Benz[c]acridine

CF3COOH

295, 380

480

Benz[a]anthracene

Pentane

284

382

280, 340

390, 410

1,2-Benzanthracene Benzanthrone

CF3COOH

370, 420

550

Benzo[b]chrysene

Pentane

283

398

11-H-Benzo[a]fluorene

Pentane

317

340

Benzoic acid

70% H2SO4

285

385

3,4-Benzopyrene (benzo[a]pyrene)

Benzene

365

390, 480

4,5-Benzopyrene (benzo[e]pyrene)

Pentane

329

389

Benzoquinoline

CF3COOH

280

425

Benzoxanthane

Pentane

363

418

Bromolysergic acid diethylamide

Water

1

315

460

Brucine

Water

7

305

500

6.13

SPECTROSCOPY

TABLE 6.8 Fluorescence Spectroscopy Data for Selected Organic Compounds (continued )

pH

Excitation wavelength, nm

Emission wavelength, nm

Compound

Solvent

Carbazole

N,NDimethylformamide

291

359

Solvent

000

000

355

445

250, 300, 310

260, 380

N H

Carboxyfluorescein HOOC

COOH

O

HO

O

Chlortetracycline Chrysene

Pentane

Cinchonine

Water

320

420

Coumarin

Ethanol

280

352

Dibenzo[a,c]anthracene

Pentane

280

381

Dibenzo[b,k]chrysene

Pentane

308

428

Dibenzo[a,e]pyrene

Pentane

370

401

370, 335, 390, 410

480, 510

O

1

O

3,4,8,9-Dibenzopyrene 5,12-Dihydronaphthacene

Pentane

282

340

1,4-Diphenylbutadiene

Pentane

328

370

Epinephrine

Water

7

295

335

Ethacridine

Water

2

370, 425

515

Fluoranthrene

Pentane

354

464

Fluorene

Pentane

300

321

6.14

SECTION 6

TABLE 6.8 Fluorescence Spectroscopy Data for Selected Organic Compounds (continued )

Compound

Solvent

pH

Fluorescein

Water

7–11

Excitation Emission wavelength, nm wavelength, nm 490

515

NH2

COOH

O

HO

O

Folic acid

Water

7

365

450

Gentisic acid

Water

7

315

440

Griseofulvin Guanine

Water Water

7 1

295, 335 285

450 365

Water

1

300, 365

400

O N

HN

H2N

N H

N

Harmine N H3CO

N H

CH3

Hippuric acid

70% H2SO4

270

370

Homovanillic acid

Water

7

270

315

m-Hydroxybenzoic acid

Water

12

314

430

p-Hydroxycinnamic acid

Water

7

350

440

7-Hydroxycoumarin

Ethanol

325

441

5-Hydroxyindole

Water

1

290

355

5-Hydroxyindoleacetic acid

Water

7

300

355

3-Hydroxykynurenine

Water

11

365

460

p-Hydroxymandelic acid

Water

7

300

380

p-Hydroxyphenylacetic acid

Water

7

280

310

p-Hydroxyphenylpyruvic acid

Water

7

290

345

p-Hydroxyphenylserine

Water

1

290

320

5-Hydroxytryptophan

Water

7

295

340

Imipramine

Water

14

295

415

N CH2CH2CH2N(CH3)2

Indoleacetic acid

Water

8

285

360

Indoles

Water

7

269, 315

355

N H

6.15

SPECTROSCOPY

TABLE 6.8 Fluorescence Spectroscopy Data for Selected Organic Compounds (continued )

Compound

Solvent

pH

Excitation Emission wavelength, nm wavelength, nm

Indomethacin

Water

13

300

410

Kynurenic acid

Water

7

325

405

11

325

440

Lysergic acid diethylamide

Water

1

325

445

Menadione

Ethanol

335

480

9-Methylanthracene

Pentane

382

410

3-Methylcholanthrene

Pentane

297

392

7-Methyldibenzopyrene

Pentane

460

467

2-Methylphenanthrene

Pentane

257

357

3-Methylphenanthrene

Pentane

292

368

1-Methylpyrene

Pentane

336

394

4-Methylpyrene

Pentane

Naphthacene (2,3-benzanthracene) 1-Naphthol

0.1 M NaOH

338

386

290, 310

480, 515

365

480

356

426

20% ethanol 2-Naphthol

0.1 M NaOH 20% ethanol

Oxytetracycline

390

520

Phenanthrene

Pentane

252

362

Phenylalanine

Water

215, 260

282

o-Phenylenepyrene

Pentane

360

506

270

305

Phenylephrine Picene

Pentane

Procaine

Water

Pyrene

Pentane

Pyridoxal

11

281

398

275

345

330

382

Water

12

310

365

Quinacrine

Water

11

285

420

Quinidine

Water

1

350

450

Quinine

Water

1

250, 350

450

CH

O

HO OH H3C

N

6.16

SECTION 6

TABLE 6.8 Fluorescence Spectroscopy Data for Selected Organic Compounds (continued )

Compound

Solvent

pH 1

Reserpine

Water

Resorcinol

Water

Riboflavin

Water

Rutin

Water

Salicylic acid Scoparone

Excitation wavelength, nm

Emission wavelength, nm

300

375

265

315

7

270, 370, 445

520

1

430

520

Water

11

310

435

Water

10

350, 365

430

10

Scopoletin

Water

Serotonin

3 M HCl

Skatole

Water

Streptomycin

Water

p-Terphenyl

Pentane

13

Thiopental Thymol

Water

Tocopherol

Hexane–

7

365, 390

460

295

550

290

370

366

445

284

338

315

530

265

300

295

340

ethanol Tribenzo[a,e,i]pyrene

Pentane

384

448

Triphenylene

Pentane

288

357

360

Tryptamine

Water

7

290

Tryptophan

Water

11

285

365

Tyramine

Water

1

275

310 310

Tyrosine

Water

7

275

Uric acid

Water

1

325

370

Vitamin A

1-Butanol

340

490

Vitamin B12

Water

Warfarin

Methanol

Xanthine

Water

7 1

275

305

290, 342

385

315

435

O N

HN O

N H

N H

2,6-Xylenol

275

305

3,4-Xylenol

280

310

Yohimbine

Water

1

270

360

Zoxazolamine

Water

11

280

320

6.17

SPECTROSCOPY

TABLE 6.9 Fluorescence Quantum Yield Values

Compound

QF value vs. QF standard

Solvent QF standard

9-Aminoacridine Anthracene POPOP* Quinine sulfate dihydrate

Water Ethanol Toluene 1 N H2SO4

0.99 0.30 0.85 0.55

Secondary standards Acridine orange hydrochloride

Ethanol

1,8-ANS† (free acid)

Ethanol

1,8-ANS (magnesium salt)

Ethanol

Fluorescein

0.1 N NaOH

Fluorescein, ethyl ester

0.1 N NaOH

Rhodamine B

Ethanol

2,6-TNS‡ (potassium salt)

Ethanol

0.54 0.58 0.38 0.39 0.29 0.31 0.91 0.94 0.99 0.99 0.69 0.70 0.48 0.51

Quinine sulfate Anthracene Anthracene POPOP Anthracene POPOP Quinine sulfate POPOP Quinine sulfate POPOP Quinine sulfate Anthracene Anthracene POPOP

* POPOP p-bis[2-(5-phenyloxazoyl)]benzene. † ANS, anilino-8-naphthalenesulfonic acid. ‡ TNS, 2-p-toluidinylnaphthalene-6-sulfonate.

TABLE 6.10 Phosphorescence Spectroscopy of Some Organic Compounds Abbreviation Used in the Table EPA: diethyl ether, isopentane, and ethanol (5:5:2) volume ratio

Compound

Solvent

Acenaphthene 3-Acetylpyridine Adenine

Ethanol Ethanol Water–methanol (9:1) Ethanol Ethanol Ethanol Water–methanol (9:1) Ethanol

Adenosine p-Aminobenzoic acid 2-Aminofluorene 6-Amino-6-methylmercaptopurine 2-Amino-4-methylpyrimidine

Lifetime, s

Excitation wavelength, nm

Emission wavelength, nm

300 395 278

515 525 406

4.6 0.66

280 305 380 321

422 425 590 456

2.1

302

438

0.5 2.9 0.8

6.18

SECTION 6

TABLE 6.10 Phosphorescence Spectroscopy of Some Organic Compounds (continued )

Compound 2-Amino-5-nitrobenzothiazole 2-Amino-5-nitrobiphenyl 3-L-Aminotyrosine · 2HCl Anthracene Aspirin Atropine 8-Azaguanine Benzaldehyde 1,2-Benzanthracene Benzimidazole Benzocaine 1,2-Benzofluorene Benzoic acid 3,4-Benzopyrene Benzyl alcohol 6-Benzylaminopurine Biphenyl 6-Bromopurine Brucine Caffeine Carbazole 2-Chloro-4-aminobenzoic acid p-Chlorophenol o-Chlorophenoxyacetic acid p-Chlorophenoxyacetic acid 6-Chloropurine Chlorpromazine · HCl Chlorotetracycline Cocaine · HCl Codeine Cytidine Desoxypyridoxine · HCl Diacetylsulfanilamide 2,6-Diaminopurine 2,6-Diaminopurine sulfate 1,2,5,6-Dibenzanthracene 2,6-Dichloro-4-nitroaniline 2,4-Dichlorophenoxyacetic acid 2,6-Diethyl-4-nitroaniline 3,4-Dihydroxymandelic acid 3,4-Dihydroxyphenylacetic acid

Solvent EPA EPA Ethanol Ethanol EPA Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol EPA Ethanol Ethanol Water–methanol (9:1) Ethanol Water–methanol (9:1) Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Water–methanol (9:1) Ethanol Ethanol Ethanol Ethanol Water–methanol (9:1) Ethanol Ethanol Water–methanol (9:1) Ethanol Ethanol EPA Ethanol EPA Ethanol Ethanol

Lifetime, s 0.41 0.56 0.8

Excitation wavelength, nm

2.8

282 254 310 280 310 315 240 325 219 286

515 520 398 462 380 410 442 433 510 406 430 502 400 508 393 413

1.0 0.5

270 273

385 420

0.9 2.0 7.8 1.0  0.2 0.7  0.5 0.64

305 285 341 312 290 280 283 273

435 440 436 337 505 518 396 419

0.3 2.7 2.7 0.3

320 280 240 270 290

490 410 400 505 420

1.4 1.3 2.7

290 280 288

442 405 410

1.7 1.3 0.5  0.5 0.66 1.1 0.9

294 340 368 289 388 294 295

424 550 525 490 525 412 430

2.1 1.4 1.8 3.4 2.2 2.3 3.4 2.4

375 380 286 300 240

Emission wavelength, nm

6.19

SPECTROSCOPY

TABLE 6.10 Phosphorescence Spectroscopy of Some Organic Compounds (continued )

Compound 2,5-Dimethoxy-4-methylamphetamine 5,7-Dimethyl-1,2-benzacridine N,N-Dimethyl-4-nitroaniline N,N-Dimethyltryptamine Dopamine Ephedrine Epinephrine N-Ethylcarbazole Ethyl 3-indoleacetate Folic acid Hippuric acid Homovanillic acid DL-5-Hydroxytryptophan Indole-3-acetic acid 3-Indoleacetonitrile Indole-3-butonoic acid Indolecarboxylic acid Indole-2-propanoic acid D-Lysergic acid 2-Methylcarbazole N-Methylcarbazole 6-Methylmercaptopurine N-Methyl-4-nitroaniline 6-Methylpurine Morphine Naphthacene Naphthalene 1-Naphthaleneacetic acid 1-Naphthol 2-Naphthoxyacetic acid 2-Naphthylamine Niacinamide Nicotine 5-Nitroacenaphthene 4-Nitroaniline 9-Nitroanthracene 1-Nitroanthraquinone 4-Nitrobiphenyl 3-Nitro-N-ethylcarbazole 2-Nitrofluorene 6-Nitroindole 1-Nitronaphthalene

Solvent Water–methanol (9:1) Ethanol EPA Water-methanol (9:1) Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol EPA Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Water–methanol (9:1) Ethanol Ethanol Water–methanol (9:1) EPA Water–methanol (9:1) Ethanol Ethanol EPA Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol EPA EPA EPA EPA EPA EPA EPA EPA EPA

Lifetime, s

Excitation wavelength, nm

Emission wavelength, nm

3.9

289

411

0.6 0.54 6.9

310 398 286

555 525 434

0.9 3.6 1.0 7.8 3.3 4.9 0.8 6.3  0.5 7.1 0.6 5.5 0.6 0.1

285 225 283 340 290 367 311 289 315 290 285 284 290 290 310

430 390 425 437 440 425 450 435 435 438 438 510 429 440 518

8.1 8.4 0.6

333 336 291

442 437 420

0.5 3.2

390 272

522 405

0.3

285 300 310 295 320 328 270 270 270 380 380 248 250 330 315 340 372 340

500 518 475 510 475 497 303 410 390 540 510 488 490 480 475 517 520 520

1.8 2.8 1.1 2.6 2.3 5.2 0.6 0.3 0.4 0.4 0.4

6.20

SECTION 6

TABLE 6.10 Phosphorescence Spectroscopy of Some Organic Compounds (continued )

Compound 2-Nitronaphthalene 4-Nitro-1-naphthylamine 4-Nitrophenol 4-Nitrophenylhydrazine 4-Nitro-2-toluidine Papaverine · HCl Phenacetin Phenanthrene Phenobarbital Phenylalanine DL-2-Phenyllactic acid Phthalylsulfathiazole Procaine · HCl Purine Pyrene Pyridine Pyridine-3-sulfonic acid Pyridoxine · HCl Quercetin Quinidine sulfate Quinine · HCl Salicyclic acid Strychnine phosphate Sulfabenzamide Sulfadiazine Sulfanilamide Sulfapyridine Sulfathiazole 1,2,4,5-Tetramethylbenzene 2-Thiouracil 2,4,5-Trichlorophenol 2,4,5-Trichlorophenoxyacetic acid Triphenylene Tryptophan Tyrosine Vitamin K1 Vitamin K3 Vitamin K5 Warfarin Yohimbine · HCl

Solvent EPA EPA Ethanol EPA EPA Ethanal EPA EPA Ethanol Ethanol Ethanol Ethanol Ethanol Water–methanol (9:1) Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol EPA Ethanol Ethanol Ethanol Ethanol Ethanol Ethanol Hexane Hexane Water–methanol (9:1) Ethanol Ethanol

Lifetime, s 0.4

Excitation wavelength, nm

340 240 270 262 305 310 272

500 578 520 520 520 480 410 465 380 385 383 405 430 405

2.1 1.3 1.3 6.2 1.2 0.7 0.7 2.9 1.4 0.9 4.5  0.5  0.2 1.1

330 310 272 290 345 340 340 315 290 305 275 300 310 310 275 310 305 295

515 440 408 425 480 500 500 430 440 405 410 410 440 420 390 430 485 475

15 1.5 2.8 0.4 0.5 1.3

290 295 290 345 335 310

460 440 390 570 510 535

0.8 7.4

305 290

460 410

 0.2 0.5 0.5 1.5 2.6 1.8 5.4 0.9 3.5 2.2

1.4 1.2

260 400 355 390 375 260

Emission wavelength, nm

6.21

SPECTROSCOPY

INFRARED SPECTROSCOPY Infrared (IR) and Raman spectroscopy rely on the interaction of a bond between two elements and IR radiation in the 400–4 000 cm1 range. The two techniques are distinct but closely related. Historically, infrared analysis has been the more widely used in organic chemistry but much of the brief discussion that follows applies equally to both methods. A chemical bond may be considered as a spring to which two weights are attached. The weights are atoms of different atomic masses. The length and strength of the spring may be correlated to the length and strength of the chemical bond. Each bond will vibrate at a frequency that is characteristic of the attached atoms and the type of bond (i.e., single, double, or triple) between them. Radiation of an appropriate frequency will be absorbed by the bond and the wavelength at which this occurs will be detected and recorded by the instrument in the spectrum. Indeed, most molecules have many bonds so multiple peaks are observed in an IR spectrum. An electrical dipole is required for IR energy to be efficiently absorbed by a molecule. Thus, bonds between different elements will give more prominent absorption peaks than will symmetrical bonds. This is because the bond’s dipole moment changes as the bond stretches and contracts. Symmetrical bonds do not change dipole moment even if the bond distance changes. Usually, the most prominent peaks are observed when the electronegativity difference between the bound elements is greatest. Thus, a C ˆ O bond will usually be more prominent than a C ˆ H bond. The position (frequency) of the absorption depends on the strength of the bond linking them. Thus, single, double, and triple bonds are observed in characteristic ranges. In addition, the frequency is related to the masses of the attached atoms. The largest mass differences occur when an element is attached to hydrogen. Such bonds as C ˆ H, O ˆ H, and N ˆ H typically are observed in the 2 900–3 600 cm1 range. The remarkable versatility of NMR as an analytical method has diminished the importance of IR analysis in modern laboratories but it remains a very useful technique. The very small amount of sample required and the prominence of functional group absorption means that the progress of a reaction can be monitored very conveniently. For example, the reduction of an aldehyde to an alcohol will be accompanied by the disappearance of the prominent C ¨ O peak and the appearance of a C ˆ OH absorption. Because both peaks are so readily identifiable in a small sample, the reaction is easy to follow and its completeness can be assayed.

TABLE 6.11 Absorption Frequencies of Single Bonds to Hydrogen Abbreviations Used in the Table m, moderately strong var, of variable strength m–s, moderate to strong w, weak s, strong w–m, weak to moderately strong Group

Band, cm1

Remarks

Saturated C ˆ H 2 975–2 950 (s) 2 885–2 865 (w)

Two or three bands usually; asymmetrical and symmetrical CH stretching, respectively. In

6.22

SECTION 6

TABLE 6.11 Absorption Frequencies of Single Bonds to Hydrogen (continued ) Group

Band, cm1

Remarks

Saturated C ˆ H (continued)

1 450–1 260 (m)

ca 2 930 (s) 2 870–2 840 (w)

1 480–1 440 (m) ca 720 (w)

presence of double bond adjacent to CH3 group symmetrical band splits into two. Sensitive to adjacent negative substituents Frequency increased in strained systems. Symmetrical band splits into two bands when double bond adjacent. Scissoring mode Rocking mode

Alkane residues attached to carbon Cyclopropane

ca 3 050 (w) 540–500 470–460 (s)

CH stretching

Cyclobutanes Cyclopentanes

580–490 (s) 595–490 (s)

Alkyl derivatives: 550–530 cm1 Alkyl derivatives: 585–530 cm1

aC(CH3)2

ca 1 380 (m) 1 175–1 165 (m) 1 150–1 130 (m)

A roughly symmetrical doublet If no H on central carbon, then one band at ca 1 190 cm1

ˆ C(CH3)3

1 395–1 385 (m) 1 365 (s)

Split into two bands

Aryl-CH3 Aryl-C2H5 Aryl-C3H7 (or C4H9) ˆ (CH2)n ˆ n1 n2 n3 n4

390–260 (m) 565–540 (m–s) 585–565 (m) 785–770 (w–m) 745–735 (w–m) 735–725 (w–m) 725–720 (w–m)

Aliphatic cyclopropanes

Two bands Rocking vibrations

Alkane residues attached to miscellaneous atoms ca 3 050 (m–s) ca 3 050 (m–s) ˆ CH2 ˆ halogen

ca 3 050 (m–s) 1 435–1 385 (m) 1 300–1 240 (s)

Halogens except fluorine

6.23

SPECTROSCOPY

TABLE 6.11 Absorption Frequencies of Single Bonds to Hydrogen (continued ) Band, cm1

Group

Remarks

Alkane residues attached to miscellaneous atoms (continued ) ˆ CHO

2 900–2 800 (w) 2 775–2 700 (w) 1 420–1 370 (m)

ˆ CO ˆ CH3

3 100–2 900 (w) 1 450–1 400 (s) 1 360–1 355 (s)

ˆ O ˆ CH3 ethers

2 835–2 810 (s) 1 470–1 430 (m–s) ca 1 030 (w–m)

ˆ O ˆ C(CH3)3

1 200–1 155 (s)

ˆ O ˆ CH2 ˆ O ˆ

2 790–2 770 (m)

ˆ O ˆ CH2 ˆ esters

1 475–1 460 (m–s) 1 470–1 435 (m–s)

ˆ O ˆ CO ˆ CH3

1 450–1 400 (s) 1 385–1 365 (s) 1 360–1 355 (s)

ˆ CH2 ˆ C ¨ Cb

1 445–1 430 (m)

ˆ CH2 ˆ SO2 ˆ

ca 1 250 (m)

P ˆ CH3 Se ˆ CH3 B ˆ CH3

1 320–1 280 (s) ca 1 280 (m) 1 460–1 405 (m) 1 320–1 280 (m) 1 265–1 250 (m–s) 1 200–1 180 (m) 1 170–1 155 (m) 1 265–1 240 (m) 1 240–1 230 (m) 1 215–1 195 (m) 1 165–1 145 (m) 1 430–1 415 (m)

Si ˆ CH3 Sn ˆ CH3 Pb ˆ CH3 As ˆ CH3 Ge ˆ CH3 Sb ˆ CH3 Bi ˆ CH3 ˆ CH2 ˆ (Cd, Hg, Zn, Sn) N ˆ CH3 and N ˆ CH2 ˆ N ˆ CH2 ˆ CH2 ˆ N

2 820–2 780 (s) 1 440–1 390 (m) 1 480–1 450 (s)

Two bands

Acyclic esters. Frequency increased ca 30 cm1 for cyclic and small ring systems. Acetate esters The high intensity of these bands often dominates this region of the spectrum.

Ethylenediamine complexes Ethylenediamine complexes

6.24

SECTION 6

TABLE 6.11 Absorption Frequencies of Single Bonds to Hydrogen (continued ) Group

Band, cm1

Remarks

Alkane residues attached to miscellaneous atoms (continued ) N ˆ CH3 Amine · HCl Amino acid · HCl Amides N ˆ CH2 ˆ amides

1 475–1 395 (m) 1 490–1 480 (m) 1 420–1 405 (s) ca 1 440 (m)

S ˆ CH3

2 990–2 955 (m–s) 2 900–2 865 (m–s) 1 440–1 415 (m) 1 325–1 290 (m) 1 030–960 (m) 710–685 (w–m)

S ˆ CH2 ˆ

2 950–2 930 (m) 2 880–2 845 (m) 1 440–1 415 (m) 1 270–1 220 (s)

ˆ C ˜ CH

ca 3 300 (s) 700–600

Sharp Bending

3 040–3 010 (m) 3 095–3 075 (m) 2 985–2 970 (m)

995–980 (s) 940–900 (s) ca 635 (s) 485–445 (m–s) 895–885 (s) 560–530 (s) 470–435 (m) 980–955 (s) 455–370 (m–s)

730–655 (m) 670–455 (s) 850–790 (m) 570–515 (s) 525–470 (s)

CH stretching sometimes obscured by much stronger bands of saturated CH groups

6.25

SPECTROSCOPY

TABLE 6.11 Absorption Frequencies of Single Bonds to Hydrogen (continued ) Band, cm1

Group

Remarks

Alkane residues attached to miscellaneous atoms (continued ) ˆ O ˆ CH ¨ CH2

965–960 (s) 945–940 (m) 820–810 (s)

ˆ S ˆ CH ¨ CH2

ca 965 (s) ca 860 (s)

ˆ CO ˆ CH ¨ CH2

995–980 (s) 965–955 (m) 950–935 (s) 870–850 (s) ca 930 (s) 880–865 940–920 (s) ca 990 (s)

ˆ CO ˆ OCH ¨ CH2 ˆ CO ˆ C ¨ CH2 ˆ CO ˆ OC ¨ CH2 ˆ O ˆ CH ¨ CH ˆ trans ˆ CO ˆ CH ¨ CH ˆ trans

Hydroxyl group O ˆ H compounds Primary aliphatic alcohols

3 640–3 630 (s) 1 350–1 260 (s) 1 085–1 030 (s)

Secondary aliphatic alcohols

3 625–3 620 (s) 1 350–1 260 (s) 1 125–1 085 (s)

Tertiary aliphatic alcohols

3 620–3 610 (s)

Only in very dilute solutions in nonpolar solvents OH bending Also broad band at 700–600 cm1 See comments under primary aliphatic alcohols Also for -unsaturated and cyclic tertiary aliphatic alcohols See comments under primary aliphatic alcohols

1 410–1 310 (s) 1 205–1 125 (s) Aryl ˆ OH

ca 3 610 (s) 1 410–1 310 (s) 1 260–1 180 (s) 1 085–1 030 (s)

Carboxylic acids Enol form of -diketones

3 300–2 500 (w–m) 995–915 (s) 2 700–2 500 (var)

See comments under primary aliphatic alcohols

Also for unsaturated secondary aliphatic alcohols Broad Broad diffuse band Broad

6.26

SECTION 6

TABLE 6.11 Absorption Frequencies of Single Bonds to Hydrogen (continued ) Group

Band, cm1

Remarks

Hydroxyl group O ˆ H compounds (continued ) Free oximes

3 600–3 570(w–m)

Free hydroperoxides

3 560–3 530 (m)

Peroxy acids

ca 3 280 (m)

Phosphorus acids

2 700–2 560 (m)

Broad

Water in solution

3 710

When solution is damp

Intermolecular H bond Dimeric

3 600–3 500

Rather sharp. Absorptions arising from H bond with polar solvents also appear in this region. Broad

Polymeric Intramolecular H bond Polyvalent alcohols Chelation

Water of crystallation (solid state spectra)

3 400–3 200 (s)

Shoulder

3 600–3 500 (s) 3 200–2 500

Sharper than dimeric band above Broad and occasionally weak; the lower the frequency, the stronger the intramolecular bond

3 600–3 100 (w)

Usually a weak band at 1 640– 1 615 cm1 also. Water in trace amounts in KBr disks shows a broad band at 3 450 cm1.

Amine, imine, ammonium, and amide N ˆ H Primary amines Aliphatic

Aromatic Amino acids

Amino salts

3 550–3 300 (m) 1 650–1 560 (m) 1 090–1 020 (w–m) 850–810 (w–m) 495–445 (m–s) ca 290 (s) 1 350–1 260 (s) 445–345 3 100–3 030 (m)

2 800–2 400 (m) 1 625–1 560 (m) 1 550–1 550 (m) 3 550–3 100 (m) ca 3 380 ca 3 280

Two bands in this range With -carbon branching at 795 cm1 and strong Broad Broad Also for secondary aryl amines Values for solid states; broad bands also (but not always) near 2 500 and 200 cm1 Number of sharp bands; dilute solution

Values for solid state Dilute solutions

6.27

SPECTROSCOPY

TABLE 6.11 Absorption Frequencies of Single Bonds to Hydrogen (continued ) Group

Band, cm1

Remarks

Amine, imine, ammonium, and amide N ˆ H (continued ) Secondary amines

Salts

Tertiary amines R1R2R3NH

3 550–3 400 (w) 1 580–1 490 (w) 1 190–1 170 (m) 1 145–1 130 (m) 455–405 (w–m) ca 2 500 ca 2 400 1 620–1 560 (m–s)

Only one band, whereas primary amines show two bands Often too weak to be noticed

Sharp; broad values for solid state Sharp; broad values for solid state

2 700–2 250

Group of relatively sharp bands; broad bands in solid state

Ammonium ion

3 300–3 030 (s) 1 430–1 390 (s)

Group of bands

Imines ¨ N ¨ H

3 350–3 310 (w) 3 490 (s) 3 490 (s)

Aliphatic Aryl Pyrroles, indoles; band sharp

Imine salts

2 700–2 330 (m–s) 2 200–1 800 (m)

Dilute solutions One or more bands; useful to distinguish from protonated tertiary amines

Primary amide ˆ CONH2

ca 3 500 (m) ca 3 400 (m)

Lowered ca 150 cm1 in the solid state and on H bonding; often several bands 3 200–3 050 cm1

Secondary amide ˆ CONH ˆ

3 460–3 400 (m)

Two bands; lowered on H bonding and in solid state. Only one band with lactams Extra band with bonded and solidstate samples

3 100–3 070 (w)

Miscellaneous R ˆ H ˆSˆH

2 600–2 550 (w)

PˆH

2 440–2 350 (m) 2 700–2 560 (m) 100/137 times the

O P

Weaker than OH and less affected by H bonding Sharp Associated OH

OH

R ˆD

corresponding RH frequency

Useful when assigning RH bands; deuteration leads to a known shift to lower frequency

6.28

SECTION 6

TABLE 6.12 Absorption Frequencies of Triple Bonds Abbreviations Used in the Table m, moderately strong var, of variable strength m–s, moderate to strong w–m, weak to moderately strong s, strong Band, cm1

Group Alkynes Terminal

3 300 (s) 2 140–2 100 (w–m)* 1 375–1 225 (w–m) 695–575 (m–s) ca 630 (s) 2 260–2 150 (var)*

Nonterminal

R1 ˆ C ˜ C ˆ R2

540–465 (m)

Aryl ˆ C ˜ C ˆ

ca 550 (m) ca 350 (var)

ˆ C ˜ C ˆ halogen (Cl, Br, I)

185–160 (var)

Nitriles ˆ C ˜ N

2 260–2 200 (var)

Aliphatic

Remarks

CH stretching C ˜ C stretching Two bands if molecule has axial symmetry Alkyl monosubstituted Symmetrical or nearly symmetrical substitution makes the C ˜ C stretching frequency inactive. When more than one C ˜ C linkage is present, and sometimes when there is only one, there are frequently more absorption bands in this region than there are triple bonds to account for them. The longer the chain, the lower the frequency

Stronger and toward the lower end of the range when conjugated; occasionally very weak or absent

580–555 (m–s) 560–525 (m–s) 390–350 (s) 580–540 (s) 430–380 (m)

Aromatic 



Isonitriles R ˆ N ˜ C or R ˆ N ¨ C:

Cyanamides   aN ˆ C ˜ N7aN ˆ C ¨ N

2 175–2 150 (s) 2 150–2 115 (s) 1 595

Very sensitive to changes in substituents Not found for nitriles

2 225–2 210 (s)

* Conjugation with olefinic or acetylenic groups lowers the frequency and raises the intensity. Conjugation with carbonyl groups usually has little effect on the position of absorption.

6.29

SPECTROSCOPY

TABLE 6.12 Absorption Frequencies of Triple Bonds (continued ) Group Thiocyanates RˆSˆC˜N

Band, cm1

2 175–2 140 (s)

404–400 (s) ca 600 (m–s) Nitrile N-oxides ˆ C ˜ N→O

Diazonium salts R ˆ N ˜ N Selenocyanates R ˆ Se ˆ C ˜ N

2 305–2 285 (s) 1 395–1 365 (s)

Remarks

Aryl thiocyanates at the upper end of the range, alkyl at the lower end Aliphatic derivatives

Aryl derivatives

2 300–2 230 (m–s)

ca 2 160 (m–s) 545–520 ca 390 ca 350

TABLE 6.13 Absorption Frequencies of Cumulated Double Bonds Abbreviations Used in the Table m–s, moderate to strong vs, very strong s, strong w, weak Group

Band, cm1

Carbon dioxide O¨C¨O

2 349 (s)

Isocyanates ˆN¨C¨O Isoselenocyanates ˆ N ¨ C ¨ Se

Azides   ˆ N3 or ˆ N ¨ N¨ N

ˆN¨C¨Nˆ

Remarks

Appears in many spectra as a result of inequalities in path length

2 275–2 250 (vs)

Position unaffected by conjugation

2 200–2 000 (s) 675–605

Broad; usually two bands

2 140–2 030 (s) 1 340–1 180 (w) 2 155–2 130 (s)

Not observed for ionic azides Split into unsymmetrical doublet by conjugation with aryl groups: 2 145–2 125 (vs) and 2 115– 2 105 (vs)

6.30

SECTION 6

TABLE 6.13 Absorption Frequencies of Cumulated Double Bonds (continued ) Group Isothiocyanates ˆN¨C¨S

Band, cm1

2 140–1 990 (vs) 649–600 (m–s) 565–510 (m–s) 470–440 (m–s)

Ketenes aC ¨ C ¨ O

ca 2 150 (s)

Ketenimines C¨C¨Nˆ

2 050–2 000 (s)

Allenes aC ¨ C ¨ Cb

2 000–1 915 (m–s)

Thionylamines ˆN¨S¨O

Diazoalkanes   R2C ¨ N ¨ N   ˆ CH ¨ N ¨ N Diazoketones   ˆ CO ˆ CH ¨ N ¨ N

Remarks

Broad; usually a doublet

Two bands when terminal allene or when bonded to electronattracting groups

1 300–1 230 (s) 1 180–1 110 (s)

2 030–2 000 (s) 2 050–2 035 (s)

2 100–2 080 2 075–2 050

Monosubstituted Disubstituted

Position of Carbonyl Absorption Because the carbonyl absorption is one of the most prominent and identifiable bands in the IR spectrum, it is often used diagnostically. The general trends of structural variation on the position of C ¨ O stretching frequencies are summarized in six principles, as follows. Details of carbonyl absorptions are recorded in Table 6.14 and for other double bonds in Table 6.15, for aromatic bonds in Table 6.16 and other miscellaneous bonds in Table 6.17. 1. The more electronegative the group X in the system R ˆ CO ˆ X ˆ , the higher is the frequency. 2. ,-Unsaturation lowers the frequency by 15–40 cm1, except in amides, where little shift is observed; if present it is usually to higher frequency. 3. Further conjugation has relatively little effect.

6.31

SPECTROSCOPY

4. Ring strain in cyclic compounds causes a relatively large shift to higher frequency. This phenomenon provides a remarkably reliable test of ring size, distinguishing clearly between four-, five-, and larger-membered-ring ketones, lactones, and lactams. Six-membered-ring and larger ketones, lactones, and lactams show the normal frequency found for the open-chain compounds. 5. Hydrogen bonding to a carbonyl group causes a shift to lower frequency of 40–60 cm1. Acids, amides, enolized -keto carbonyl systems, and o-hydroxyphenol and o-aminophenyl carbonyl compounds show this effect. All carbonyl compounds tend to give slightly lower values for the carbonyl stretching frequency in the solid state compared with the value for dilute solutions. 6. Where more than one of the structural influences on a particular carbonyl group is operating, the net effect is usually close to additive. An especially convenient aspect of IR spectroscopy is its practice. A small amount of sample can be pressed between two NaCl or KBr (Table 6.19) disks and the spectrum can be determined without further preparation. A spectrum so obtained is recorded as “neat” or “between salts.” If the sample is a solid, it may be mixed in a mortar and pestle with KBr and then pressed into a disk. The salt disk may be placed directly in the IR beam. In neither case is there a concern about solvent peaks. Of course, solvents may be used. Carbon tetrachloride and chloroform are the most commonly used solvents when the compound requires dissolution. Alternately, the sample may be intimately mixed (mulled) with mineral oil (a hydrocarbon oil). The thick slurry may then be smeared on a salt disk and placed in the spectrometer. The brand of mineral oil used historically is Nujol and such slurries are still called “Nujol mulls.” The transmission characteristics of potential solvents for IR spectroscopy may be found in Table 6.20. Traditional analog spectrometers were calibrated by taking a second spectrum of polystyrene. The sharp 1 641 cm1 band was recorded on the same sheet as the original spectrum. Modern Fourier transform instruments do not usually require this step but still require calibration. TABLE 6.14 Absorption Frequencies of Carbonyl Bands All bands quoted are strong.

Groups Acid anhydrides ˆ CO ˆ O ˆ CO ˆ Saturated

Aryl and ,-unsaturated Saturated five-ring All classes

Band, cm1

1 850–1 800 1 790–1 740

1 830–1 780 1 700–1 710 1 870–1 820 1 800–1 750 1 300–1 050

Remarks

Two bands usually separated by about 60 cm1. The higherfrequency band is more intense in acyclic anhydrides, and the lower-frequency band is more intense in cyclic anhydrides.

One or two strong bands due to CO stretching

6.32

SECTION 6

TABLE 6.14 Absorption Frequencies of Carbonyl Bands (continued ) Groups Acid chlorides ˆ COCl Saturated Aryl and ,-unsaturated Acid peroxide CO ˆ O ˆ O ˆ CO ˆ Saturated Aryl and ,-unsaturated Esters and lactones ˆ CO ˆ O ˆ Saturated Aryl and ,-unsaturated Aryl and vinyl esters C ¨ C ˆ O ˆ CO ˆ alkyl Esters with electronegative  substituents; e.g., aCCl ˆ CO ˆ O ˆ -Keto esters Six-ring and larger lactones

Five-ring lactone ,-Unsaturated five-ring lactone

Band, cm1

1 815–1 790

Acid fluorides higher, bromides and iodides lower

1 790–1 750

1 820–1 810 1 800–1 780 1 805–1 780 1 785–1 755

1 750–1 735 1 730–1 715 1 800–1 750

The C ¨ C stretching band also shifts to higher frequency.

1 770–1 745 1 755–1 740 Similar values to the corresponding open-chain esters 1 780–1 760 1 770–1 740

,-Unsaturated five-ring lactone, vinyl ester type Four-ring lactone -Keto ester in H bonding enol form

ca 1 800 ca 1 820

All classes

1 300–1 050

Aldehydes ˆ CHO (See also Table 6.39 for C ˆ H.) All values given below are lowered in liquidfilm or solid-state spectra by about 10–20 cm1. Vaporphase spectra have values raised about 20 cm1.

Remarks

ca 1 650

When -CH is present, there are two bands, the relative intensity depending on the solvent.

Keto from normal; chelate-type H bond causes shift to lower frequency than the normal ester. The C ¨ C band is strong and is usually near 1 630 cm1. Usually two strong bands due to CO stretching

6.33

SPECTROSCOPY

TABLE 6.14 Absorption Frequencies of Carbonyl Bands (continued ) Groups

Band, cm1

Aldehydes ˆ CHO (continued) Saturated Aryl

1 740–1 720 1 715–1 695

,-Unsaturated ,,,-Unsaturated -Ketoaldehyde in enol form

1 705–1 680 1 680–1 660 1 670–1 645

Ketones aC ¨ O All values given below are lowered in liquid-film or solid-state spectra by about 10–20 cm1. Vapor-phase spectra have values raised about 20 cm1. Saturated Aryl ,-Unsaturated ,, , -Unsaturated and diaryl Cyclopropyl Six-ring ketones and larger

Five-ring ketones

1 725–1 705 1 700–1 680 1 685–1 665 1 670–1 660 1 705–1 685 Similar values to the corresponding open-chain ketones 1 750–1 740

Four-ring ketones -Halo ketones

ca 1 780 1 745–1 725

, -Dihaloketones

1 765–1 745

1,2-Diketones, syn-transopen chains

1 730–1 710

syn-cis-1,2-Diketones, six-ring syn-cis-1,2-Diketones, five ring o-Amino-aryl or o-hydroxyaryl ketones

Remarks

o-Hydroxy or amino groups shift this value to 1 655–1 625 cm1 because of intramolecular H bonding.

Lowering caused by chelate-type H bonding

, Unsaturation, ,, , unsaturation, etc., have a similar effect on these values as on those of open-chain ketones. Affected by conformation; highest values are obtained when both halogens are in the same plane as the C ¨ O. Anti-symmetrical stretching frequency of both C ¨ O’s. The symmetrical stretching is inactive in the infrared but active in the Raman.

1 760 and 1 730 1 775 and 1 760 1 655–1 635

Low because of intramolecular H bonding. Other substituents and steric hindrance affect the position of the band.

6.34

SECTION 6

TABLE 6.14 Absorption Frequencies of Carbonyl Bands (continued ) Groups Ketones aC ¨ O (continued) Quinones Extended quinones Tropone Carboxylic acids ˆ CO2H All types

Saturated

,-Unsaturated Aryl -HaloCarboxylate ions ˆCO 2 Most types Amides ˆ CO ˆ Nb (See also Table 6.39 for NH stretching and bending.) Primary ˆ CONH2 In solution Solid state In solution Solid state

Band, cm1

1 690–1 660 1 655–1 635 1 650

3 000–2 500

1 725–1 700

Remarks

C ¨ C band is strong and is usually near 1 600 cm1. Near 1 600 cm1 when lowered by H bonding as in tropolones OH stretching; a characteristic group of small bands due to combination bands The monomer is near 1 760 cm1, but is rarely observed. Occasionally both bands, the free monomer, and the H-bonded dimer can be seen in solution spectra. Ether solvents give one band near 1 730 cm1.

1 715–1 690 1 700–1 680 1 740–1 720 1 610–1 550 1 420–1 300

Anti-symmetrical and symmetrical stretching, respectively

ca 1 690 ca 1 650 ca 1 600 ca 1 640

Amide I; C ¨ O stretching Amide II: mostly NH bending Amide I is generally more intense than amide II. (In the solid state, amides I and II may overlap.)

Secondary ˆ CONH ˆ In solution Solid state In solution Solid state

1 700–1 670 1 680–1 630 1 550–1 510 1 570–1 515

Tertiary

1 670–1 630

Lactams Six-ring and larger rings Five-ring Four-ring

ca 1 670 ca 1 700 ca 1 745

Amide I Amide II; found in open-chain amides only Amide I is generally more intense than amide II. Since H bonding is absent, solid and solution spectra are much the same.

Shifted to higher frequency when the N atom is in a bridged system

6.35

SPECTROSCOPY

TABLE 6.14 Absorption Frequencies of Carbonyl Bands (continued ) Band, cm1

Groups

Remarks Shifted 15 cm1 by the additional double bond Shifted by up to 15 cm1 by the additional double bond. This is an unusual effect by , unsaturation. It is said to be due to the inductive effect of the C ¨ C on the well-conjugated CO ˆ N system, the usual conjugation effect being less important in such a system.

R ˆ CO ˆ N ˆ C ¨ C C ¨ C ˆ CO ˆ N

Imides ˆ CO ˆ N ˆ CO ˆ Cyclic six-ring Cyclic five-ring

ca 1 710 and ca 1 700 ca 1 770 and ca 1 700

Shift of 15 cm1 with , unsaturation

Ureas N ˆ CO ˆ N RNHCONHR Six-ring Five-ring

ca 1 660 ca 1 640 ca 1 720

Urethanes R ˆ O ˆ CO ˆ N

1 740–1 690

Also shows amide II band when nonsubstituted on N

Thioesters and Acids RCO ˆ S ˆ R RCOSH

ca 1 720

,-Unsaturated or aryl acid or ester shifted about 25 cm1

RCOS ˆ alkyl RCOS ˆ aryl

ca 1 690 ca 1 710

TABLE 6.15 Absorption Frequencies of Other Double Bonds Abbreviations Used in the Table m, moderately strong vs, very strong m-s, moderate to strong w, weak var, of variable strength Group

Band, cm1

Remarks

Alkenes aC ¨ Cb Nonconjugated

1 680–1 620 (w-m)

Conjugated with aromatic ring

1 640–1 610 (m)

May be very weak if symmetrically substituted More intense than with unconjugated double bonds

6.36

SECTION 6

TABLE 6.15 Absorption Frequencies of Other Double Bonds Alkenes aC ¨ Cb (continued) Internal (ring)

3 060–2 995 (m)

Carbons: n  3 n4 n5

ca 1 665 (w-m) ca 1 565 (w-m) ca 1 610 (w-m) 1 370–1 340 (s) 1 650–1 645 (w-m)

n6

Highest frequencies for smallest ring

Characteristic

Exocyclic C ¨ C(CH2)n n  2 n3 n4

1 780–1 730 (m) ca 1 680 (m) 1 655–1 650 (m)

Fulvene

1 645–1 630 (m) 1 370–1 340 (s) 790–765 (s)

Dienes, trienes, etc.

1 650 (s) and 1 600 (s)

Lower-frequency band usually more intense and may hide or overlap the higher-frequency band

,-Unsaturated carbonyl compounds

1 640–1 590 (m)

Usually much weaker than the C ¨ O band

Enol esters, enol ethers, and enamies

1 700–1 650 (s) Imines, oximes, and amidines aC ¨ N ˆ

Imines and oximes Aliphatic ,-Unsaturated and aromatic Conjugated cyclic systems

1 690–1 640 (w) 1 650–1 620 (m) 1 660–1 480 (var) 960–930 (s)

NO stretching of oximes

Imino ethers ˆ O ˆ C ¨ N ˆ

1 690–1 640 (var)

Usually a strong doublet

Imino thioethers ˆ S ˆ C ¨ N ¨

1 640–1 605 (var)





Imine oxides aC ¨ Nˆ O

1 620–1 550 (s)

Amidines aN ˆ C ˆ N ˆ

1 685–1 580 (var)

Benzamidines Aryl ˆ C ¨ N ¨ N

1 630–1 590

6.37

SPECTROSCOPY

TABLE 6.15 Absorption Frequencies of Other Double Bonds (continued) Band, cm1

Group

Remarks

Imines, oximes, and amidines aC ¨ N ˆ (continued ) Guanidine

1 725–1 625 (s)

Azines aC¨NˆN¨Cb

1 670–1 600

Hydrazoketones ˆ CO ˆ C ¨ N ˆ N

1 600–1 530 (vs)

Azo compounds ˆ N ¨ N ˆ Azo ˆ N ¨ N ˆ Aliphatic Aromatic cis (Z ) trans (E ) Azoxy Aliphatic

ca 1 575 (var) ca 1 510 (w) 1 440–1 410 (w)

+

N

O

N

–

Aromatic 

Very weak or inactive



Azothio ˆ N ¨ Nˆ S ˆ

1 590–1 495 (m-s) 1 345–1 285 (m-s) 1 480–1 450 (m-s) 1 340–1 315 (m-s) 1 465–1 445 (w) 1 070–1 055 (w) Nitro compounds N ¨ O

Nitro C ˆ NO2 Aliphatic

Aromatic

ca 1 560 (s) 1 385–1 350 (s)

1 570–1 485 (s) 1 380–1 320 (s)

865–835 (s)

The two bands are due to asymmetrical and symmetrical stretching of the N ¨ O bond. Electron-withdrawing substituents adjacent to nitro group increase the frequency of the asymmetrical band and decrease that of the symmetrical frequency. See above remark; also bulky orthosubstituents shift band to higher frequencies. Strong H bonding shifts frequency to lower end of range. Strong and sometimes at ca 750 cm1

6.38

SECTION 6

TABLE 6.15 Absorption Frequencies of Other Double Bonds Band, cm1

Group

Remarks

Nitro compounds N ¨ O (continued )

,-Unsaturated Nitroalkenes

580–520 (var) 1 530–1 510 (s) 1 360–1 335 (s)

Nitrates ˆ O ˆ NO2

1 650–1 625 (vs) 1 285–1 275 (vs) 870–855 (vs) 760–755 (w-m) 710–695 (w-m)

Nitramines aN ˆ NO2

1 630–1 550 (s) 1 300–1 250 (s) 1 680–1 610 (vs) 815–750 (s) 850–810 (s) 690–615 (s)

Nitrates ˆ O ˆ N ¨ O

Thionitrites ˆ S ˆ N ¨ O

730–685 (m-s)

Nitroso cC ˆ N ¨ O

1 600–1 500 (s)



Two bands Trans (E ) form Cis (Z ) form



N ˆ N¨ O Aliphatic Aromatic

Nitrogen oxides N→O Pyridine Pyrazine

1 530–1 495 (m-s) 1 480–1 450 (m-s) 1 335–1 315 (m-s)

1 320–1 230 (m-s) 1 190–1 150 (m-s) 1 380–1 280 (m-s) 1 040–990 (m-s) ca 850 (m)

Affected by ring substituents

6.39

SPECTROSCOPY

TABLE 6.16 Absorption Frequencies of Aromatic Bands Abbreviations Used in the Table

m, moderately strong m-s, moderate to strong s, strong Group Aromatic rings

Band, cm1 ca 1 600 (m) ca 1 580 (m) ca 1 470 (m) ca 1 510 (m)

Five adjacent H

900–860 (w-m) 770–730 (s) 720–680 (s) 625–605 (w-m) ca 550 (w-m)

1,2-Substitution

770–735 (s) 555–495 (w-m) 470–415 (m-s)

1,3-Substitution

810–750 (s) 560–505 (m) 460–415 (m-s)

1,4-Substitution

860–800 (s) 650–615 (w-m) 520–440 (m-s)

1,2,3-Trisubstitution

800–760 (s) 720–685 (s) 570–535 (s) ca 485

1,2,4-Trisubstitution

900–885 (m) 780–760 (s) 475–425 (m-a)

1,3,5-Trisubstitution

950–925 (var) 865–810 (s) 730–680 (m-s) 535–495 (s) 470–450 (w-m)

Pentasubstitution

900–860 (m-s) 580–535 (s)

Hexasubstitution

415–385 (m-s)

var, of variable strength w-m, weak to moderately strong

Remarks Stronger when ring is further conjugated When substituent on ring is electron acceptor When substituent on ring is electron donor

Substituents: C ¨ C, C ˜ C, C ˜ N

490–460 cm1 when substituents are electron-accepting groups

520–490 cm1 when substituents are electron-donating groups

6.40

SECTION 6

TABLE 6.17 Absorption Frequencies of Miscellaneous Bands Abbreviations Used in the Table m, moderately strong vs, very strong m-s, moderate to strong w, weak s, strong w-m, weak to moderately strong var, of variable strength Group

Band, cm1

Remarks

Ethers Saturated aliphatic cC ˆ O ˆ Cd

1 150–1 060 (vs)

1 140–900 (s)

Two peaks may be observed for branched chain, usually 1 140– 1 110 cm1. Usually 930–900 cm1; may be absent for symmetric ethers

Alkyl-aryl

Vinyl

1 270–1 230 (vs) 1 120–1 020 (s)

¨ CO stretching CO stretching

1 225–1 200 (s)

Usually about 1 205 cm1

Diaryl 1 200–1 120 (s) 1 100–1 050 (s) Cyclic

1 270–1 030 (s)

Epoxides

Ketals and acetals

1 260–1 240 (m-s) 880–805 (m) 950–860 (var) 865–785 (m) 770–750 (m)

Monosubstituted Trans (E ) form Cis (Z ) form Trisubstituted

1 190–1 140 (s) 1 195–1 125 (s) 1 100–1 000 (s) 1 060–1 035 (s)

Strongest band Sometimes obscured

Phthalanes

915–895 (s)

Aromatic methylenedioxy

1 265–1 235 (s) Peroxides

ˆOˆOˆ

900–830 (w) 1 150–1 030 (m-s) ca 1 000 (m)

Alkyl Aryl

6.41

SPECTROSCOPY

TABLE 6.17 Absorption Frequencies of Miscellaneous Bands (continued ) Group

Band, cm1

Remarks

Sulfur compounds Thiols ˆSˆH ˆ CO ˆ SH ˆ CS ˆ SH

2 600–2 450 (w) 840–830 (m) ca 860 (s)

Broad

Thiocarbonyl 1 200–1 050 (s)

Behaves generally in a manner similar to carbonyl band

1 570–1 395 1 420–1 260 1 140–940 ca 580 (s)

Sulfoxides aS ¨ O

1 075–1 040 (vs)

Halogen or oxygen atom bonded to sulfur increases the frequency.

730–690 (var) 395–360 (var) Sulfones aSO2

1 360–1 290 (vs)

Halogen or oxygen atom bonded to sulfur increases the frequency.

1 170–1 120 (vs) 610–545 (m-s) 525–495 (m-s) Sulfonamides ˆ SO2 ˆ Nb

Sulfonates ˆ SO2 ˆ O ˆ

Thiosulfonates ˆ SO2 ˆ S ˆ Sulfates ˆ O ˆ SO2 ˆ O ˆ Primary alkyl salts

1 380–1 330 (vs) 1 170–1 140 (vs) 950–860 (m) 715–700 (w-m)

1 420–1 330 (s) 1 200–1 145 (s)

May appear as doublet

ca 1 340 (vs) 1 415–1 380 (s) 1 200–1 185 (s) 1 315–1 220 (s) 1 140–1 075 (m)

Electronegative substituents increase frequencies. Strongly influenced by metal ion

6.42

SECTION 6

TABLE 6.17 Absorption Frequencies of Miscellaneous Bands (continued ) Group

Band, cm1

Remarks

Sulfur compounds (continued ) Sulfates ˆ O ˆ SO2 ˆ O (continued ) Secondary alkyl salts

Stretching frequencies of C ˆ S and S ˆ S bonds ˆ S ˆ CH3 ˆ S ˆ CH2 ˆ ˆ S ˆ CHb ˆ S ˆ Cd ˆ S ˆ aryl RˆSˆSˆR Aryl ˆ S ˆ S ˆ aryl Polysulfides CH2 ˆ S ˆ CH2 ˆ (R ˆ S)2C ¨ O

1 270–1 210 (vs) 1 075–1 050 (s)

710–685 (w-m) 660–630 (w-m) 630–600 (w-m) 600–570 (w-m) 1 110–1 070 (m) 710–685 (w-m) 705–570 (w) 520–500 (w) 500–430 (w-m) 500–470 (w-m) 695–655 (w-m) 880–825 (s) 570–560 (var) 1 035–935 (s) ca 580 (s) 1 050–900 (m-s) 980–850 (m-s) 900–800 (m-s)

Doublet; both bands strongly influenced by metal ion

CSC stretching

Monoionic Ionic 1,1-dithiolates

Phosphorus compounds PˆH

2 455–2 265 (m)

Sharp. Phosphines lie in the region 2 285–2 265 cm1.

1 150–965 (w-m) ˆ PH2

1 100–1 085 (m) 1 065–1 040 (w-m) 940–910 (m)

P ˆ alkyl

795–650 (m-s)

P ˆ aryl

1 130–1 090 (s) 750–680 (s)

P ˆ O ˆ alkyl

1 050–970 (s)

P ˆ O ˆ aryl

1 240–1 190 (s)

PˆOˆP

970–910

Broad

Broad

6.43

SPECTROSCOPY

TABLE 6.17 Absorption Frequencies of Miscellaneous Bands (continued ) Group

Band, cm1

Remarks

Phosphorus compounds (continued ) P¨O

1 350–1 150 (s)

May appear as doublet

2 725–2 520 (w-m) 2 350–2 080 (w-m)

H-bonded; broad Broad; may be doublet for aryl acids

1 740–1 600 (w-m) 1 335 (s) 1 090–910 (s) 540–450 (w-m) P¨S

P ¨ O stretching

865–655 (m-s) 595–530 (var) 3 100–3 000 (w) 2 360–2 200 (w) 935–910 (s) 810–750 (m-s) 6 55–585 (var)

PO stretching P ¨ S stretching P ¨ S stretching

Silicon compounds Si ˆ H

2 250–2 100 (s) 985–800

SiH3 has two bands.

Si ˆ Cd

860–760

Accompanied by CH2 rocking

Si ˆ CH3

1 280–1 250 (s)

Sharp

Si ˆ C2H5

1 250–1 220 (m) 1 020–1 000 (m) 970–945 (m)

Si ˆ Aryl

1 125–1 090 (vs)

Splits into two bands when two aryl groups are attached to one silicon atom, but has only one band when three aryl groups attached

cSi ˆ OH

870–820

OH deformation band

cSi ˆ O ˆ Sid

1 100–1 000

cSi ˆ N ˆ Sid

940–870 (s)

cSi ˆ Cl

550–470 (s) 250–150

6.44

SECTION 6

TABLE 6.17 Absorption Frequencies of Miscellaneous Bands (continued ) Group

Band, cm1

Remarks

Silicon compounds (continued ) aSiCl2

595–535 (s) 540–460 (m)

ˆ SiCl3

625–570 (s) 535–450 (m) Boron compounds

Boranes aBH or ˆ BH2

2 640–2 450 (m-s) 2 640–2 570 (m-s) 2 535–2 485 (m-s) 2 380–2 315 (s)

Free H in BH Free H in BH2 plus second band In complexes; second band for BH2

2 285–2 265 (s) 2 140–2 080 (w-m) 2 580–2 450 (m)

Bridged H Borazoles and borazines

BH4

2 310–2 195 (s)

Two bands

BˆN

1 550–1 330 750–635

Borazines and borazoles

BˆO

1 390–1 310 (s) 1 280–1 200

BO stretching Metal orthoborates

B ˆ Cl B ˆ Br

1 090–890 (s)

Plus other bands at lower frequencies for BX2 and BX3

BˆF

1 500–840 (var)

Isotope splitting present

XBF2

1 500–1 410 (s) 1 300–1 200 (s)

X2BF

1 360–1 300 (s)

BF3 complexes

1 260–1 125 (s) 1 030–800 (s)

BF4

ca 1 030 (vs)

Band splitting may be added to isotopic splittings.

6.45

SPECTROSCOPY

TABLE 6.17 Absorption Frequencies of Miscellaneous Bands (continued ) Group

Band, cm1

Remarks

Halogen compounds CˆF Aliphatic, mono-F Aliphatic, di-F Aliphatic, poly-F Aromatic

ˆ CF3 Aliphatic

Aromatic

C ˆ Cl Primary alkanes

Secondary alkanes

Tertiary alkanes Poly-Cl Aryl: 1,21,31,4-

1 110–1 000 (vs) 780–680 (s) 1 250–1 050 (vs) 1 360–1 090 (vs) 1 270–1 100 (m) 680–520 (m-s) 420–375 (var) 340–240 (s)

1 350–1 120 (vs) 780–680 (s) 680–590 (s) 600–540 (s) 555–505 (s) 1 330–1 310 (m-s) 600–580 (s)

730–720 (s) 685–680 (s) 660–650 (s) ca 760 (m) 675–655 (m-s) 615–605 (s) 635–610 (m-s) 580–560 (m-s) 800–700 (vs) 1 060–1 035 (m) 1 080–1 075 (m) 1 100–1 090 (m)

Chloroformates

ca 690 (s) 485–470 (s)

Axial Cl Equatorial Cl

730–580 (s) 780–740 (s)

C ˆ Br Primary alkanes

Secondary alkanes

645–635 (s) 565–555 (s) 440–430 (var) 620–605 (s) 590–575 (m-w) 540–530 (s)

Two bands Number of bands

6.46

SECTION 6

TABLE 6.17 Absorption Frequencies of Miscellaneous Bands (continued ) Group

Band, cm1

Remarks

Halogen compounds (continued ) C ˆ Br (continued) Tertiary alkanes Axial Equatorial Aryl: 1,21,3-; 1,4Other bands

CˆI Primary alkanes Secondary alkanes

Tertiary alkanes

Aromatic

Axial Equatorial

600–595 (m-s) 525–505 (s) 690–550 (s) 750–685 (s) 1 045–1 025 (m) 1 075–1 065 (m) 400–260 (s) 325–175 (m-s) 290–225 (m-s)

600–585 (s) 515–500 (s) ca 575 (s) 550–520 (s) 490–480 (s) 580–560 (s) 510–485 (m) 485–465 (s) 1 060–1 055 (m-s) 310–160 (s) 265–185 ca 640 (s) ca 655 (s) Inorganic ions

Ammonium

3 300–3 030

Cyanate

2 220–2 130 (s)

Cyanide

2 200–2 000

Carbonate

1 450–1 410

Hydrogen sulfate

1 190–1 160 (s) 1 180–1 000 (s) 880–840 (m)

Nitrate

1 410–1 350 (vs) 860–800 (m)

Nitrite

1 275–1 230 (s) 835–800 (m)

Several bands, all strong

Shoulder

6.47

SPECTROSCOPY

TABLE 6.17 Absorption Frequencies of Miscellaneous Bands (continued ) Group

Band, cm1

Remarks

Inorganic ions (continued ) Phosphate

1 100–1 000

Sulfate

1 130–1 080 (s)

Thiocyanate

ca 2 050 (s)

TABLE 6.18 Absorption Frequencies in the Near Infrared Values in parentheses are molar absorptivity

Class Acetylenes

Band, cm1

Remarks

9 800–9 430 6 580–6 400 (1.0)

Overtone of ˜ CH stretching

Alcohols (nonhydrogen-bonded)

7 140–7 010 (2.0)

Overtone of OH stretching

Aldehydes Aliphatic

4 640–4 520 (0.5)

Combination of C ¨ O and CH stretchings

Aromatic

Formate Alkanes ˆ CH3

ˆ CH2 ˆ

c CH

Cyclopropane

ca 8 000 ca 4 525 ca 4 445 4 775–4 630 (1.0)

9 000–8 350 (0.02) 5 850–5 660 (0.1) 4 510–4 280 (0.3) 9 170–8 475 (0.02) 5 830–6 640 (0.1) 4 420–4 070 (0.25) 8 550–8 130 7 000–6 800 5 650–5 560 6 160–6 060 4 500–4 400

Alkenes 6 850–6 370 (1.0)

7 580–7 300 (0.02) 6 140–5 980 (0.2) 4 760–4 700 (1.2)

All bands very weak

6.48

SECTION 6

TABLE 6.18 Absorption Frequencies in the Near Infrared (continued ) Class

Band, cm1

Remarks

Alkenes (continued)

4 760–4 660 (0.15)

Trans (E ) isomers have no unique bands.

6 250–6 040 (0.3) 7 580–7 410 (0.02) 6 190–5 990 (0.3) 4 820–4 750 (0.2–0.5) Amides Primary

7 400–6 540 (0.7) 5 160–5 060 (3.0) 5 040–4 990 (0.5) 4 960–4 880 (0.5)

Secondary

Amines, aliphatic Primary

7 330–7 140 (0.5) 5 050–4 960 (0.4)

9 710–9 350 6 670–6 450 (0.5) 5 075–4 900 (0.7)

Secondary

Amines, aromatic Primary

Secondary

Aryl-H

9 800–9 350 6 580–6 410 (0.5)

Two bands; overtone of NH stretch Second overtone of C ¨ O stretch; second overtone of NH deformation; combination of C ¨ O and NH Overtone of NH stretch Combination of NH stretch and NH bending

Second overtone of NH stretch Two bands; overtone of NH stretch Two bands; combination of NH stretch and NH bending Second overtone of NH stretch Overtone of NH stretch

9 950–9 520 (0.4) 7 040–6 850 (0.2) 6 760–6 580 (1.4) 5 140–5 040 (1.5) 10 000–9 710 6 800–6 580 (0.5) 7 660–7 330 (0.1) 6 170–5 880 (0.1)

Carbonyl

5 200–5 100

Carboxylic acids

7 000–6 800

Epoxide (terminal)

6 135–5 960 (0.2) 4 665–4 520 (1.2)

Overtone of CH stretch

Cyclopropane bands in same region

6.49

SPECTROSCOPY

TABLE 6.18 Absorption Frequencies in the Near Infrared (continued ) Class Glycols Hydroperoxides Aliphatic Aromatic

Band, cm1 7 140–7 040

6 940–6 750 (2.0) 4 960–4 880 (0.8) 7 040–6 760 (1.0) 4 950–4 850 (1.3)

Imides

9 900–9 620 6 540–6 370

Nitriles

5 350–5 200 (0.1)

Oximes

7 140–7 050

Phosphines

5 350–5 260 (0.2)

Phenols Nonbonded Intramolecularly bonded Thiols

Remarks

Two bands

7 140–6 800 (3.0) 5 000–4 950 7 000–6 700 5 100–4 950 (0.05)

TABLE 6.19 Infrared Transmitting Materials

Material NaCl, rock salt KBr, potassium bromide KCl, potassium chloride AgCl, silver chloride* AgBr, silver bromide* CaF2, calcium fluoride (Irtran-3) BaF2, barium fluoride MgO, magnesium oxide (Irtran-5) CsBr, cesium bromide CsI, cesium iodide TlBr–TlI, thallium bromide–iodide (KRS-5)* ZnS, zinc sulfide (Irtran-2) * Useful for internal reflection work.

Wavelength range,

m

Wavenumber range, cm1

Refractive index at 2 m

0.25–17 0.25–25 0.30–20 0.40–23 0.50–35 0.15–9 0.20–11.5 0.39–9.4 1–37 1–50 0.50–35

40 000–590 40 000–400 33 000–500 25 000–435 20 000–286 66 700–1 110 50 000–870 25 600–1 060 10 000–270 10 000–200 20 000–286

1.52 1.53 1.5 2.0 2.2 1.40 1.46 1.71 1.67 1.74 2.37

0.57–14.7

17 500–680

2.26

6.50

SECTION 6

TABLE 6.19 Infrared Transmitting Materials (continued )

Material ZnSe, zinc selenide* (vacuum deposited) (Irtran-4) CdTe, cadmium telluride (Irtran-6) Al2O3, sapphire* SiO2, fused quartz Ge, germanium* Si, silicon* Polyethylene * Useful for internal reflection work.

Wavelength range,

m

Wavenumber range, cm1

Refractive index at 2 m

1–18

10 000–556

2.45

2–28 0.20–6.5 0.16–3.7 0.50–16.7 0.20–6.2 16–300

5 000–360 50 000–1 538 62 500–2 700 20 000–600 50 000–1 613 625–33

2.67 1.76 4.0 3.5 1.54

TABLE 6.20 Infrared Transmission Characteristics of Selected Solvents

6.51

6.52

TABLE 6.20 Infrared Transmission Characteristics of Selected Solvents (continued)

6.53

6.54

SECTION 6

RAMAN SPECTROSCOPY Infrared and Raman spectroscopy are related by the fact that both permit the detection of bond vibrations. Like IR spectroscopy, the spectral bands are reported in cm1. An important difference is that the wavelength and intensity of inelastically scattered light is measured in the Raman spectroscopic method. The “Raman effect” causes the scattered radiation to shift according to the energies of molecular vibrations. Although Raman spectroscopy involves a physical principle different from that in IR spectroscopy, the two techniques are complementary. Infrared spectroscopy relies on a changing dipole during a bond vibration for absorption of energy to occur. In Raman, it is a change in polarizability in the bond that permits absorption. The simple molecule carbon dioxide, O ¨ C ¨ O, is an instructive example. Both C ¨ O bonds have dipoles but they oppose each other and the net dipole is 0 Debye (0 D). The symmetrical stretch in which both C ¨ O bonds simultaneously extend and contract does not change the dipole but is detectable by Raman because the polarizability of the system alters. Raman scattering is not a very efficient process and an energy source of considerable power is required. This is typically an argon (Ar) laser. A variety of chemical bonds and systems can be detected by modern Raman spectrometers and typical data are summarized in Tables 6.21–6.30.

TABLE 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon Abbreviations Used in the Table m, moderately strong vw, very weak m-s, moderate to strong w, weak m-vs, moderate to very strong w-m, weak to moderately strong s, strong w-m, weak to moderately strong vs, very strong w-vs, weak to very strong Group

Band, cm1

Remarks

Saturated C ˆ H and C ˆ C ˆ CH3

ˆ CH2 ˆ

2 969–2 967 (s) 2 884–2 883 (s) ca 1 205 (s) 1 150–1 135 1 060–1 056 975–835 (s) 280–220 2 949–2 912 (s) 2 861–2 849 (s) 1 473–1 443 (m-vs) 1 305–1 295 (s) 1 140–1 070 (m) 888–837 (w) 425–150 500–490

In aryl compounds In unbranched alkyls In unbranched alkyls Terminal rocking of methyl group CH2 ˆ CH3 torsion

Intensity proportional to number of CH2 groups Often two bands; see above

Substituent on aromatic ring

6.55

SPECTROSCOPY

TABLE 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon (continued ) Group

Band, cm1

Remarks

Saturated C ˆ H and C ˆ C (continued ) ˆ CH(CH3)2

ˆ C(CH3)3

Internal tertiary carbon atom

Internal quaternary carbon atom

Two adjacent tertiary carbon atoms

Dialkyl substitution at -carbon atom

Cyclopropane

1 350–1 330 (m) 835–750 (s)

1 265–1 240 (m) 1 220–1 200 (m) 760–685 (vs)

If attached to C ¨ C bond, 870–800 cm1. If attached to aryl ring, 740 cm1 Not seen in tert-butyl bromide Not seen in tert-butyl bromide If attached to C ¨ C or aromatic ring, 760–720 cm1

855–805 (w) 455–410

710–680 (vs) 490–470

730–920 770–725

Often a band at 530–524 cm1 indicates presence of adjacent tertiary and quaternary carbon atoms.

800–700 (m-s) 680–650 (vs) 605–550 3 101–3 090 3 038–3 019 1 210–1 180 (s)

Cyclobutane

1 001–960 (vs)

Cyclopentane

900–800 (s)

Cyclohexane

825–815 (vs) 810–795 (vs)

Shifts to 1 200 cm1 for monoalkyl or 1,2-dialkyl substitution and to 1 320 cm1 for gem-1,1dialkyl substitution Shifts to 933 cm1 for monoalkyl, to 887 cm1 for cis-1,3-dialkyl, and to 891 cm1 plus 855 cm1 (doublet) for trans-1,3-dialkyl subsition

Boat configuration Chair configuration

6.56

SECTION 6

TABLE 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon (continued ) Band, cm1

Group

Remarks

Saturated C ˆ H and C ˆ C (continued ) Cycloheptane

ca 733

Cyclooctane

ca 703

CH3

1 392–1 377

C

450–400 (vw) 270–250 (m)

CH3 CH3

H C

C CH3

H CH3

CH3 C

C H

H CH3

1 372–1 368 970–952 (m) 592–545 (vw) 420–400 (m) 310–290 (m)

CH3 C

1 385–1 375 522–488 (w)

C

CH3

H

CH3

CH3 C

C

CH3 C

1 380–1 379 492–455 (vw) 220–200 (m)

CH3 C

C

O

1 392–1 386 690–678 (m-s) 510–485 (m) 424–388 (w) 1 170–1 100 (w-m) 600–580 (m-s) 1 120–1 090 (m-vs)

C

C O

Tertiary or quaternary carbon adjacent to carbonyl group lowers the frequency 300 cm1

600–510 (w-m)

ˆ CH2 ˆ CO ˆ

1 420–1 410 (s)

ˆ CHO

2 850–2 810 (m) 2 720–2 695 (vs)

Often appears as a shoulder

6.57

SPECTROSCOPY

TABLE 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon (continued ) Group

Band, cm1

Remarks

Unsaturated C ˆ H ˆC˜CˆH

3 340–3 270 (w-m)

Alkyl substituents at higher frequencies; unsaturated or aryl substituents at lower frequencies

3 040–2 995 (m)

3 095–3 050 (m) 2 990–2 983 (s)

Asymmetric ¨ CH2 stretch Symmetric ¨ CH2 stretch

1 419–1 415 (m) 1 309–1 2 888 (m)

Plus ¨ CH and ¨ CH stretching bands

1 413–1 399 (m) 909–885 (m) 711–684 (w)

Plus ¨ CH2 stretching bands

1 270–1 251 (m)

Plus ¨ CH stretching band

1 314–1 290 (m)

Plus ¨ CH stretching band

1 360–1 322 (w) 830–800 (vw)

Plus ¨ CH stretching band

Hydroxy O ˆ H Free ˆ OH Intermolecularly bonded Aromatic ˆ OH

3 650–3 250 (w) 3 400–3 300 (w) ca 3 160 (s)

ˆ OH

1 460–1 320 (w) 1 276–1 205 (w-m) 1 260 (w-m)

Common to all OH substituents Primary Secondary

6.58

SECTION 6

TABLE 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon (continued ) Group

Band, cm1

Remarks

Hydroxy O ˆ H (continued ) C ˆ C ˆ OH primary

C ˆ C ˆ OH Secondary

Tertiary

ˆ CO ˆ O ˆ H

1 070–1 050 (m-s) 1 030–960 (m-s) 480–430 (w-m)

CCO stretching CCO deformation

1 135–1 120 (m-s) 825–815 (vs) 500–490 (w-m) 1 210–1 200 (m-s) 755–730 (vs) 360–350 (w-m) 1 305–1 270

CO stretching

N ˆ H and C ˆ N bonds Amine aN ˆ H Associated Nonbonded Salts ˆ NH2 Amides Primary

Secondary

3 400–3 250 (s) 3 550–3 250 (s) 2 986–2 974 1 650–1 590 (w-vs)

3 540–3 500 (w) 3 400–3 380 (w) 1 310–1 250 (s)

1 150–1 095 (m) 3 491–3 404 (m-s)

Primary amines show two bands. Often obscured by intense CH stretching bands Bending Both bands lowered ca 150 cm1 in solid state and H bonding Interaction of NH bending and CN stretching; lowered 50 cm1 in nonbonded state Rocking of NH2 Two bands; lowered in frequency on H bonding and in solid state

1 190–1 130 (m) 931–865 (m-s) 430–395 (w-m) ˆ CO ˆ N

607–555 (m)

O ¨ CN bending

1 070–1 045 (m)

Stretching

cC ˆ Nb Primary carbon Secondary  carbon

1 090–1 060 (m) 1 140–1 035 (m)

Tertiary  carbon

1 240–1 020 (m)

CN stretching Two bands but often obscured. Strong band at 800 cm1 Two bands. Strong band also at 745 cm1

6.59

SPECTROSCOPY

TABLE 6.22 Raman Frequencies of Triple Bonds Abbreviations Used in the Table m, moderately strong s-vs, strong to very strong m-s, moderate to strong vs, very strong s, strong Group

Band, cm1

R ˆ C ˜ CH

2 160–2 100 (vs) 650–600 (m) 356–335 (s)

R1 ˆ C ˜ C ˆ R2

2 300–2 190 (vs)

ˆC˜CˆC˜Cˆ

2 264–2 251 (vs)

ˆC˜N

2 260–2 240 (vs)

2 234–2 200 (vs) 840–800 (s-vs) 385–350 (m-s) 200–160 (vs) HˆC˜N Azides   ˆ Nˆ N ˜ N

Diazonium salts  R ˆ N˜ N Isonitriles  ˆ N ˜ C

Thiocyanates ˆSˆC˜N

Remarks Monoalkyl substituted; C ˜ C stretch C ˜ CH deformation C ˜ C ˆ C bending of monoalkyls C ˜ C stretching of disubstituted alkyls; sometimes two bands

Unsaturated nonaryl substituents lower the frequency and enhance the intensity. Lowered ca 30 cm1 with aryl and conjugated aliphatics CCCN symmetrical stretching Aliphatic nitriles

2 094 (vs)

2 170–2 080 (s) 1 258–1 206 (s)

Asymmetric NNN stretching Symmetric NNN stretching; HN3 at 1 300 cm1

2 300–2 240 (s)

2 146–2 134 2 124–2 109

Stretching of aliphatics Stretching of aromatics

2 260–2 240 (vs) 650–600 (s)

Stretching of C ˜ N Stretching of SC bond

6.60

SECTION 6

TABLE 6.23 Raman Frequencies of Cumulated Double Bonds Abbreviations Used in the Table s, strong vw, very weak vs, very strong w, weak Group Allenes C¨C¨C

Carbodiimides (cyanamides) ˆN¨C¨Nˆ

Band, cm1

2 000–1 960 (s) 1 080–1 060 (vs) 356

Pseudo-asymmetric stretching Symmetric stretching C ¨ C ¨ C bending

2 140–2 125 (s)

Asymmetric stretching of aliphatics Asymmetric stretching of aromatics; two bands Symmetrical stretching of aliphatics Symmetric stretching of aryls

2 150–2 100 (vs) 1 460 1 150–1 140 (vs) Cumulenes (trienes) C¨C¨C¨C

Isocyanates ˆN¨C¨O

Isothiocyanates ˆN¨C¨S

Ketenes C¨C¨O

Sulfinylamines RˆN¨S¨O

Remarks

2 080–2 030 (vs) 878

2 300–2 250 (vw) 1 450–1 400 (s)

Asymmetric stretching Symmetric stretching

2 220–2 100 690–650

Two bands Alkyl derivatives

2 060–2 040 (vs) 1 130 (s) 1 374 (s) 1 120 (s)

Pseudo-asymmetric stretching Pseudo-symmetric stretching Alkyl derivatives Aryl derivatives

1 306–1 214 (w) 1 155–989 (s)

Asymmetric stretching Symmetric stretching

6.61

SPECTROSCOPY

TABLE 6.24 Raman Frequencies of Carbonyl Bonds Abbreviations Used in the Table m, moderately strong s-vs, strong to very strong m-s, moderate to strong vs, very strong s, strong w, weak Group Acid anhydrides ˆ CO ˆ O ˆ CO ˆ Saturated Conjugated, noncyclic

Acid fluorides ˆ CO ˆ F Alkyl Aryl Acid chlorides ˆ CO ˆ Cl Alkyl Aryl

Band, cm1

1 850–1 780 (m) 1 771–1 770 (m) 1 775 1 720

1 840–1 835 1 812–1 800

1 810–1 770 (s) 1 774 1 731

Acid bromides ˆ CO ˆ Br Alkyl Aryl

1 812–1 788 1 775–1 754

Acid iodides ˆ CO ˆ I Alkyl Aryl

ca 1 806 ca 1 752

Lactones

1 850–1 730 (s)

Esters Saturated

1 741–1 725

Aryl and ,-unsaturated Diesters Oxalates Phthalates C ˜ C ˆ CO ˆ O ˆ Carbamates

Remarks

1 727–1 714 1 763–1 761 1 738–1 728 1 716–1 708 1 694–1 688

Aldehydes

1 740–1 720 (s-vs)

Ketones Saturated Aryl

1 725–1 700 (vs) 1 700–1 650 (m)

Alkyl branching on carbon adjacent to C ¨ O lowers frequency by 5–15 cm1.

6.62

SECTION 6

TABLE 6.24 Raman Frequencies of Carbonyl Bonds (continued ) Group

Band, cm1

Ketones (continued) Alicyclic n 4 n 5 n6

1 782 (m) 1 744 (m) 1 725–1 699 (m)

Carboxylic acids Mono-

1 686–1 625 (s)

PolyAmino acids Carboxylate ions Amino acid anion

Amides (see also Table 6.21) Primary Associated Nonbonded Secondary Associated

Nonbonded Tertiary Lactams

1 782–1 645 1 750–1 710 1 743–1 729 1 690–1 550 (w) 1 440–1 340 (vs) 1 743–1 729 1 600–1 570 (w)

Remarks

These -substituents increase the frequency: F, Cl, Br, OH. Solid state; often two bands In solution; very broad band

Often masked by water deformation band near 1 630 cm1

1 686–1 576 (m-s) 1 650–1 620 (m) 1 715–1 675 (m) 1 620–1 585 (m) 1 680–1 630 (w) 1 570–1 510 (w) 1 490–1 440 1 700–1 650 1 550–1 500 1 670–1 630 (m) 1 750–1 700 (m)

Both cis (Z) and trans (E ) forms Trans (E ) form Cis (Z ) form Both cis (Z ) and trans (E ) forms Trans (E ) form (no cis band)

6.63

SPECTROSCOPY

TABLE 6.25 Raman Frequencies of Other Double Bonds Abbreviations Used in the Table m, moderately strong vs, very strong m-s, moderate to strong w, weak s, strong s-vs, strong to very strong w-m, weak to moderately strong Band, cm1

Group

Remarks

Alkenes aC ¨ Cb aC ¨ Cb

Haloalkene

X  fluorine

1 680–1 576 (m-s)

General range

1 648–1 638 (vs)

C ¨ C stretching

ca 1 650 (vs) 270–252 (w)

C ¨ C stretching C ¨ C ˆ C skeletal deformation

ca 1 660 (vs) 970–952 (w)

C ¨ C stretching Asymmetric CC stretching

1 676–1 665 (s)

C ˆ C stretching

1 678–1 664 (vs) 522–488 (w)

C ¨ C stretching C ¨ C ˆ C skeletal deformation

1 680–1 665 (s) 690–678 (m-s) 510–485 (m) 424–388 (w)

C ¨ C stretching Symmetrical CC stretching Skeletal deformation Skeletal deformation

X  chlorine

X  bromine

X-iodine

aC ¨ Cb stretch of haloalkanes H2C ¨ CHX HXC ¨ CHX cis (Z) trans (E ) H2C ¨ CX2 X2C ¨ CHX X2C ¨ CX2

1 654

1 603–1 601

1 596–1 593

1 581

1 712 1 694 1 728 1 792 1 872

1 590–1 587 1 578–1 576 1 616–1 611 1 589–1 582 1 577–1 571

1 587–1 583 1 582–1 581 1 593 1 552 1 547

1 543 1 537

1 465 (solid)

6.64

SECTION 6

TABLE 6.25 Raman Frequencies of Other Double Bonds (continued ) Group

Band, cm1

Remarks

aC ˆ N ˆ bonds Aldimines (azomethines) 1 673–1 639

Dialkyl substituents at higher frequency; diaryl substituents at lower end of range

1 405–1 400 (s) Aldoximines and Ketoximes aC ˆ N ˆ OH

Azines aC ¨ N ˆ N ¨ Cb

1 680–1 617 (vs) 1 335–1 330 (w)

1 625–1 608 (s)

Hydrazones

1 660–1 610 (s-vs)

Imido ethers 1 658–1 648

NH stretching at 3 360–3 327 cm1

1 665–1 642 (vs)

Aliphatic. Thiosemicarbazones fall in lower end of range. Aromatic derivatives

Semicarbazones and thiosemicarbazones

1 620–1 610 (vs)

Azo compounds ˆ N ¨ N ˆ ˆN¨Nˆ

1 580–1 570 (vs) 1 442–1 380 (vs) 1 060–1 030 (vs)

Nonconjugated Conjugated to aromatic ring CN stretching in aryl compounds

Nitro compounds N ¨ O Alkyl nitrites

1 660–1 620 (s)

N ¨ O stretching

Alkyl nitrates

1 635–1 622 (w-m) 1 285–1 260 (vs) 610–562 (m)

Asymmetric NO2 stretching Symmetric NO2 stretching NO2 deformation

6.65

SPECTROSCOPY

TABLE 6.25 Raman Frequencies of Other Double Bonds (continued ) Group

Band, cm1

Remarks

Nitro compounds N ¨ O (continued ) Nitroalkanes Primary

1 560–1 548 (m-s) 1 395–1 370 (s) 915–898 (m-s) 894–873 (m-s) 618–609 (w) 640–615 (w) 494–472 (w-m)

Secondary

Tertiary

Nitrogen oxides   cN →O

1 553–1 547 (m) 1 375–1 360 (s) 908–868 (m) 863–847 (s) 625–613 (m) 560–516 (s) 1 543–1 533 (m) 1 355–1 345 (s)

1 612–1 602 (s) 1 252 (m) 1 049–1 017 (s) 835 (s) 541 (w) 469 (w)

Sensitive to substituents attached to CNO2 group

Shoulder Broad; useful to distinguish from secondary nitroalkanes

Sharp band

6.66

SECTION 6

TABLE 6.26 Raman Frequencies of Aromatic Compounds Abbreviations Used in the Table m, moderately strong var, of variable strength m-s, moderate to strong vs, very strong m-vs, moderate to very strong w, weak s, strong w-m, weak to moderately strong s-vs, strong to very strong Group

Band, cm1

Remarks

Common features Aromatic compounds

3 070–3 020 (s) 1 630–1 570 (m-s)

CH stretching C ˆ C stretching

Substitution patterns of the benzene ring Monosubstituted

1 180–1 170 (w-m) 1 035–1 015 (s) 1 010–990 (vs)

Characteristic feature; found also with 1,3- and 1,3,5-substitutions

630–605 (w) 1,2-Disubstituted

1 230–1 215 (m) 1 060–1 020 (s) 740–715 (m)

1,3-Disubstituted

1 010–990 (vs) 750–640 (s)

1,4-Disubstituted

1 230–1 200 (s-vs) 1 180–1 150 (m) 830–750 (vs)

Characteristic feature Lowered 60 cm1 for halogen substituents Characteristic feature

Lower frequency with Cl substituents

650–630 (m-w) Isolated hydrogen

1,2,3-Trisubstituted

1 379 (s-vs) 1 290–1 200 (s) 745–670 (m-vs) 580–480 (s) 1 100–1 050 (m) 670–500 (vs)

Characteristic feature

The lighter the mass of the substituent, the higher the frequency

490–430 (w) 1,2,4-Trisubstituted

750–650 (vs) 580–540 (var) 500–450 (var)

Lighter mass at higher frequencies

6.67

SPECTROSCOPY

TABLE 6.26 Raman Frequencies of Aromatic Compounds (continued) Band, cm1

Group

Remarks

Substitution patterns of the benzene ring (continued) 1,3,5-Trisubstituted

1 010–990 (vs)

Completely substituted

1 296 (s) 550 (vs) 450 (m) 361 (m) Other aromatic compounds

Naphthalenes

1 390–1 370 1 026–1 012 767–762 535–512 519–512

Ring breathing  or  substituents  substituents  substituents  substituents

Disubstituted naphthalenes

773–737 (s) 726–705 (s)

608 575–569 544–537

1,2-; 1,3-; 2,3-; 2,6-; 2,71,3-; 1,4-(two bands); 1,6-; 1,7(two bands) 1,2-; 1,4-(two bands); 1,5-; 1,8(two bands) 1,31,2-; 1,3-; 1,61,2-; 1,7-; 1,8-

1 415–1 385

Ring breathing

690–634 (s)

Anthracenes

TABLE 6.27 Raman Frequencies of Sulfur Compounds Abbreviations Used in the Table m, moderately strong s-vs, strong to very strong m-s, moderate to strong vs, very strong s, strong w-m, weak to moderately strong Group

Band, cm1

Remarks

ˆSˆH

2 590–2 560 (s)

SH stretching for both aliphatic and aromatic

aC ¨ S

1 065–1 050 (m) 735–690 (vs)

aS ¨O In (RO2)2SO In (R2N)2SO

1 209–1 198 1 108

Solid state

One or two bands

6.68

SECTION 6

TABLE 6.27 Raman Frequencies of Sulfur Compounds (continued ) Band, cm1

Group a S ¨ O (continued ) In R2SO SOF2 SOCl2 SOBr2

Remarks

1 070–1 010 (w-m) 1 308 1 233 1 121

Broad

ˆ SO2 ˆ

1 330–1 260 (m-s) 1 155–1 110 (s) 610–540 (m) 512–485 (m)

Asymmetric SO2 stretching Symmetric SO2 stretching Scissoring mode of aryls Scissoring mode of alkyls

ˆ SO2 ˆ Nb

ca 1 322 (m) 1 163–1 138 (s) 524–510 (s)

Asymmetric SO2 stretching Symmetric SO2 stretching Scissoring mode

ˆ SO2 ˆ O

1 363–1 338 (w-m)

SO2 stretching. Aryl substituents occur at higher range.

1 192–1 165 (vs) 589–517 (w-m)

ˆ SO2 ˆ S ˆ

1 334–1 305 (m-s) 1 128–1 126 (s) 559–553 (m-s)

X ˆ SO2 ˆ X

1 412–1 361 (w-m) (F) (Cl) 1 263–1 168 (s) (F) (Cl) 596–531 (s)

ˆ O ˆ SO2 ˆ O ˆ

1 388–1 372 (s) 1 196–1 188 (vs)

O

C

S

Scissoring (two bands). Aryl substituents occur at higher range of frequencies.

670–620 (vs) 480–450 (vs)

C ¨ S stretching CS stretching

cC ˆ SH

920 (m) 850–820 (m)

C ˆ SH deformation of aryls

cC ˆ S ˆ

752 (vs), 731 (vs) 742–722 (m-s) 698 (w), 678 (s) 693–639 (s) 651–610 (s-vs) 589–585 (vs)

With vinyl group attached With CH3 attached With allyl group attached Ethyl or longer alkyl chain Isopropyl group attached tert-Butyl group attached

S

6.69

SPECTROSCOPY

TABLE 6.27 Raman Frequencies of Sulfur Compounds (continued ) Band, cm1

Group

Remarks

cC ˆ S ˆ (continued )

n2 n4 n5

1 112 688 659

cC ˆ (S ˆ S)n ˆ Cd Didi-n-alkyl disulfides Di-tert-butyl disulfide Trisulfides

715–620 (vs) 525–510 (vs) 576 (s) 543 (m) 510–480 (s)

Two bands; CS stretching Two bands; SS stretching CS stretching SS stretching SS stretching

TABLE 6.28 Raman Frequencies of Ethers Abbreviations Used in the Table m, moderately strong var, of variable strength s, strong vs, very strong Band, cm1

Group cC ˆ O ˆ Cd Aliphatic

1 200–1 070 (m)

930–830 (s) 800–700 (s)

Remarks

Asymmetrical COC stretching. Symmetrical substitution gives higher frequencies Symmetrical COC stretching Branching at  carbon gives higher frequencies.

550–400 1 310–1 210 (m) 1 050–1 010 (m)

Aromatic

1 145–1 129 (m) 900–800 (vs) 537–370 (s) 396–295 1 280–1 240 (s) ˆOˆOˆ

800–770 (var) n3 n4 n5

1 040–1 010 (s) 920–900 (s) 820–800 (s)

Ring breathing

6.70

SECTION 6

TABLE 6.29 Raman Frequencies of Halogen Compounds Abbreviations Used in the Table m-s, moderate to strong var, of variable strength s, strong vs, very strong Group

Band, cm1

Remarks

CˆF

1400–870

Correlations of limited applicability because of vibrational coupling with stretching

C ˆ Cl Primary Secondary Tertiary

350–290 (s) 660–650 (vs) 760–605 (s) 620–540 (var)

CCCl bending; general

¨ C ˆ Cl

844–564 438–396 381–170

¨ CCl2

601–441 300–235

C ˆ Br

690–490 (s)

May be one to four bands May be one to three bands

Often several bands; primary at higher range of frequencies. Tertiary has very strong band at ca 520 cm1.

305–258 (m-s) ¨ C ˆ Br

745–565 356–318 240–115

¨ CBr2

467–265 185–145

CˆI

663–595 309 154–85

¨CˆI

ca 180

Solid state

¨ CI2

ca 265 ca 105

Solid state Solid state

6.71

SPECTROSCOPY

TABLE 6.30 Raman Frequencies of Miscellaneous Compounds Abbreviations Used in the Table m, moderately strong vs, very strong s, strong vvs, very very strong Group

Band, cm1

C ˆ As

570–550 (vs) 240–220 (vs) 480–420 (s) 570–510 (vvs) 1300–1200 (s) 600–450 (s) 2350–2240 (m)

C ˆ Pb C ˆ Hg C ˆ Si C ˆ Sn PˆH

Remarks CAs stretching CAsC deformation CPb stretching CHg stretching CSi stretching CSn stretching PH stretching

Heterocyclic rings Trimethylene oxide Trimethylene imine Tetrahydrofuran Pyrrolidine 1,3-Dioxolane 1,4-Dioxane Piperidine Tetrahydropyran Morpholine Piperazine Furan Pyrazole Pyrrole Thiophene

Pyridine

1029 1026 914 899 939 834 815 818 832 836 1515–1460 1140 1040–990 1420–1360 (vs) 1144 1410 (s) 1365 (s) 1085 (vs) 1035 (s) 832 (vs) 610 (s) 1030 (vs) 990 (vs)

2-Substituted

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY Nuclear Magnetic Resonance (NMR) Spectroscopy is by far the most widely used analytical technique in the modern organic chemistry lab. Numerous monographs have been written on this subject. It would be impossible to cover all of the significant points here. The reader who is interested in knowing what the proton (1H) or carbon (13C) spectrum of a particular compound is directed to the Aldrich Library of NMR Spectra or the Sadtler Library.

6.72

SECTION 6

A number of resources are also available online. These include software for the prediction and analysis of spectral data and databases. Resources include: Proton NMR basics: http://jchemed.chem.wisc.edu/JCESoft/Programs/PNMRB/ NMR database: www.acornnmr.com/database.htm NMR prediction: www.acdlabs.com/products/spec_lab/predict_nmr/ NMR library: www.acdlabs.com/products/spec_lab/exp_spectra/spec_libraries/aldrich.html NMR Periodic Table for half-integer quadrupole spins: www.pascal-man.com/periodic-table/periodictable.html

Nuclear Magnetic Resonance Table 6.31 presents the nuclear properties of the elements. Hydrogen (1H) is an almost ideal nucleus for NMR spectroscopy. First, its natural abundance is high so most of the nuclei present in the sample will be detected in the NMR experiment. Second, its sensitivity is high meaning that its signal is readily detected. The nuclei that have been most generally used in organic chemistry are 1H and 13C although the natural abundance of the latter is low. Advances in instruments have made the acquisition of 13C-NMR spectra routine. Several other nuclei have high natural abundance and occur frequently in organic compounds. These include 7Li, 11B, 14N, 19F, 23Na, and 35Cl, which are shown in bold type in Table 6.31. Modern NMR spectrometers permit the acquisition of NMR spectra from many nuclei depending on the probe. The most favorable nuclei are those that have spin 1/2, high natural abundance, high sensitivity, and no quadrupole moment. Of course, the importance of the problem under study will ultimately dictate whether the investigator will invest the time and effort to obtain the spectrum when the experiment is difficult. Table 6.31 Nuclear properties of the elements In the following table the magnetic moment  is in multiples of the nuclear magneton N (eh/4Mc) with diamagnetic correction, the spin I is in multiples of h/2, and the electric quadrupole moment Q is in multiples of 1028 square meters. Nuclei with spin 12 have no quadrupole moment. The sign of  and Q is uncertain for those nuclides for which no sign is given. Sensitivity is for equal number of nuclei at constant field. NMR frequency at any magnetic field is the entry for column 5 multiplied by the value of the magnetic field in kilogauss. For example, in a magnetic field of 14.0924 kG, protons (1H) will precess at a frequency of 4.25760  14.0924 kG  60.000 MHz. In a magnetic field of 23.4924 kG, protons will precess at 4.25760  23.4924 kG  100.00 MHz.

6.73

SPECTROSCOPY

TABLE 6.31 Nuclear Properties of the Elements

Nuclide 1

n H 2 H 3 H 3 He 6 Li 7 Li 9 Be 10 B 11 B 13 C 14 N 15 N 17 O 19 F 21 Ne 22 Na 23 Na 24 Na 25 Mg 27 Al 29 Si 31 P 33 S 35 S 35 Cl 36 Cl 37 Cl 39 K 40 K 41 K 43 Ca 45 Sc 47 Ti 49 Ti 50 V 51 V 53 Cr 55 Mn 57 Fe 59 Co 61 Ni 63 Cu 65 Cu 67 Zn 69 Ga 1

Natural abundance, %

Spin I

— 99.985 0.015 — 0.000 13 7.42 92.58 100 19.7 80.3 1.108 99.635 0.365 0.037 100 0.257 — 100 — 10.11 100 4.71 100 0.76 — 75.53 — 24.47 93.22 0.011 8 6.77 0.145 100 7.32 5.46 0.25 99.75 9.55 100 2.17 100 1.25 69.1 30.9 4.11 60.2

1/2 1/2 1 1/2 1/2 1 3/2 3/2 3 3/2 1/2 1 1/2 5/2 1/2 3/2 3 3/2 4 5/2 5/2 1/2 1/2 3/2 3/2 3/2 2 3/2 3/2 4 3/2 7/2 7/2 5/2 7/2 6 7/2 3/2 5/2 1/2 7/2 3/2 3/2 3/2 5/2 3/2

Sensitivity at constant field relative to 1H 0.322 1.000 0.009 64 1.21 0.443 0.008 51 0.294 0.013 9 0.019 9 0.165 0.015 9 0.001 01 0.001 04 0.029 1 0.834 0.027 2 0.018 1 100 0.001 15 0.026 8 0.207 0.078 5 0.066 4 0.002 26 0.008 50 0.004 71 0.012 1 0.002 72 0.000 508 0.005 21 0.000 083 9 0.063 9 0.301 0.002 10 0.003 76 0.055 3 0.383 0.000 10 0.178 0.000 033 3 0.281 0.003 50 0.093 8 0.116 0.002 86 0.069 3

NMR frequency for a 1000 G field, MHz 2.916 70 4.257 60 0.653 57 4.541 31 3.243 38 0.626 55 1.654 65 0.598 27 0.457 4 1.365 95 1.070 54 0.307 6 0.431 5 0.577 39 4.005 43 0.336 11 0.443 4 1.126 21 0.322 0.260 6 1.109 40 0.845 8 1.723 8 0.326 6 0.508 0.417 1 0.489 3 0.347 2 0.198 64 0.247 0 0.109 03 0.286 54 1.034 34 0.239 97 0.240 04 0.424 3 1.119 22 0.240 63 1.055 42 0.138 1.007 2 0.380 48 1.128 5 1.209 0 0.266 3 1.021 88

Magnetic moment /N, J·T1

Electric quadrupole moment Q, 1028m2

1.913 12 2.792 78 0.857 42 2.978 9 2.127 6 0.822 03 3.256 36 1.177 45 1.800 6 2.688 5 0.702 4 0.403 75 0.283 1 1.893 7 2.628 8 0.661 76 1.746 2.217 40 1.690 0.855 4 3.641 3 0.555 26 1.131 7 0.643 5 — 0.821 81 1.285 3 0.684 07 0.391 43 1.298 1 0.214 9 1.317 2 4.755 9 0.788 46 1.104 14 3.347 0 5.148 5 0.473 5 3.449 0.090 42 4.616 0.749 8 2.222 8 2.381 2 0.875 24 2.014 5

— — 0.002 8 — — 0.000 8 0.04 0.05 0.111 0.041 — 0.01 — 0.004 — 0.09 — 0.10 — 0.22 0.15 — — 0.055 0.038 0.080 0.10 0.006 2 0.049 0.061 0.060 — 0.22 0.29 0.24 0.06 0.05 0.03 0.4 — 0.38 0.16 0.211 0.195 0.16 0.19

6.74

SECTION 6

TABLE 6.31 Nuclear Properties of the Elements 9 (continued)

Nuclide 71

Ga As 77 Se 79 Br 81 Br 87 Rb 93 Nb 113 In 119 Sn 121 Sb 123 Sb 125 Te 127 I 129 Xe 195 Pt 199 Hg 203 Tl 207Pb 75

Natural abundance, %

Spin I

Sensitivity at constant field relative to 1H

39.8 100 7.58 50.52 49.48 27.85 100 4.23 8.58 57.25 42.75 6.99 100 26.44 33.8 16.84 29.50 21.7

3/2 3/2 1/2 3/2 3/2 3/2 9/2 1/2 1/2 5/2 7/2 1/2 5/2 1/2 1/2 1/2 1/2 1/2

0.142 0.025 1 0.006 97 0.078 6 0.098 4 0.177 0.482 0.345 0.051 8 0.160 0.045 7 0.031 6 0.093 5 0.021 2 0.009 94 0.005 72 0.187 0.009 13

NMR frequency for a 1000 G field, MHz 1.298 40 0.729 2 0.811 8 1.066 9 1.149 8 1.292 3 1.040 48 0.931 2 1.586 8 1.019 2 0.551 9 1.345 3 0.851 7 1.177 79 0.915 23 0.761 2 2.433 2 0.889 8

Magnetic moment /N, J·T1

Electric quadrupole moment Q, 1028m2

2.559 7 1.439 0.534 2.105 5 2.269 6 2.750 0 6.167 0.622 5 1.046 1 3.359 2 2.546 6 0.887 2 2.809 1 0.776 8 0.602 2 0.504 15 1.611 5 10.578 3

0.12 0.29 — 0.37 0.31 0.13 0.22 — — 0.28 0.36 — 0.79 — — — — —

Chemical Shifts In essence, the chemical shift of a nucleus such as proton (1H) is its resonance frequency. It is usually expressed in parts per million (ppm) relative to a standard. The most common standard is tetramethylsilane [(CH3)4Si, TMS] which defines 0 on the delta () scale and 10 on the older, less used scale. A small amount of TMS is typically added to the NMR solution to be examined. The presence of an internal standard minimizes experimental variations. This is particularly important because the chemical shift is typically a change of only a few hertz per megahertz, hence the part per million (ppm) scale. The separation of peaks will be greater in hertz at higher field but spectra obtained at different field strengths are comparable on the ppm scale. Common reference standards are listed in Table 6.32.

TABLE 6.32 Proton Chemical Shifts of Reference Compounds Relative to Tetramethylsilane

Compound Tetramethylsilane, (CH3)4Si 3-(Trimethylsilyl)-1-propanesulfonic acid, sodium salt (DSS), (CH3)3SiCH2CH2COONa Sodium acetate 1,2-Dibromoethane

Chemical shift , ppm*

Solvent(s)

0.0 0.0

CDCl3, CCl4 D2O

1.90 3.63

D 2O CDCl3

6.75

SPECTROSCOPY

TABLE 6.32 Proton Chemical Shifts of Reference Compounds Relative to Tetramethylsilane (continued)

Compound

Chemical shift , ppm*

1,1,2,2-Tetrachloroethane, Cl2HCCHCl2 1,4-Benzoquinone 1,4-Dichlorobenzene Chloroform, CHCl3 Benzene 1,3,5-Trinitrobenzene

5.95 6.78 7.23 7.27 7.37 9.21

Solvent(s) CDCl3, CCl4 CDCl3, CCl4 CCl4 CDCl3, CCl4 CDCl3, CCl4 DMSO-d6† CDCl3

*Shift relative to TMS, first entry in table; † Dimethylsulfoxide-d6

A typical solution prepared for NMR analysis rarely contains more than a few percent of solute. Thus, protons on the solvent could significantly distort the spectrum. When 1 H-NMR are desired, solvents having no protons (CS2 or CCl4) or deuterated solvents are used. Table 6.33 gives the common NMR solvents used. Although modern manufacturing methods typically produce NMR solvents having high isotopic purity, incomplete deuteration of a protonic solvent will result in a residual signal.

TABLE 6.33 Common NMR Solvents Solvent

Detail

Group*

 (ppm)

Acetic acid-d4

D3C ˆ COOD

Acetone-d6 Acetonitrile-d3 Benzene-d6 tert-Butanol-d1 Chloroform-d1 Cyclohexane-d12 Deuterium oxide Dimethylformamide-d7

CD3COCD3 CD3C ˜ N C6D6 (CH3)3COD Cl3CD C6D12 D2O (CD3)2N ˆ CD ¨ O

Dimethylsulfoxide-d6 (DMSO-d6)

CD3SOCD3

CD2H OH CD2H CD2H CˆH CD2H Cl3CH CHD HOD CD2H ˆ CH ¨ O CD2H

2.05 11.5† 2.057 1.95 6.78 1.28 7.25 1.40 4.7† 2.75; 2.95 8.05 2.51

Absorbed H2O Methylene

3.3† 3.55

Methyl

2.60

CD2H OH

3.35 4.8†

D2 C

1,4-Dioxane-d8

D2 C

O O

Hexamethylphosphoramide-d18, HMPA-d18, (D3 C) 2 N HMPT-d18 Methanol-d4

CD3 OD

CD 2 CD 2

O P

N(CD 3 )2

N(CD 3 )2

*Impurity peak resulting from incomplete deuteration or exchange. †These values may vary greatly depending on the solute and its concentration.

6.76

SECTION 6

TABLE 6.33 Common NMR Solvents (continued ) Solvent

Detail

Group*

(ppm)

Dichloromethane-d2 Pyridine-d5

Cl2CD2

Cl2CDH C-2 ˆ H

5.35 8.5

C-3 ˆ H C-4 ˆ H

7.0 7.35

CD-2 ˆ H CD-3 ˆ H

3.58 1.73

CD2H Ring CD

2.3 7.1

Hydroxyl

11.3†

D(4) D

D(3)

D

N

CD2

D2C

Tetrahydrofuran-d6

D2C Toluene-d8

D(2)

O

D

CD2 D

D

CD 3 D

Trifluoroacetic acid-d1

D

F3C ˆ COOD

*Impurity peak resulting from incomplete deuteration or exchange. †These values may vary greatly depending on the solute and its concentration.

TABLE 6.34 Proton Chemical Shifts Values are given on the  scale;  10.00  . Abbreviations Used in the Table R, alkyl group Ar, aryl group Substituent group

Methyl protons

Methylene protons

Methine proton

HC ˆ C ˆ CH2 HC ˆ C ˆ NR2 HC ˆ C ˆ C ¨ C HC ˆ C ˆ C ¨ O HC ˆ C ˆ NRAr HC ˆ C ˆ H(C ¨ O)R HC ˆ C ˆ (C ¨ O)NR2 HC ˆ C ˆ (C ¨ O)Ar HC ˆ C ˆ (C ¨ O)OR HC ˆ C ˆ Ar HC ˆ C ˆ OH HC ˆ C ˆ OR HC ˆ C ˆ C ˜ CR HC ˆ C ˆ C ˜ N HC ˆ C ˆ SR HC ˆ C ˆ OAr HC ˆ C ˆ O(C ¨ O)R HC ˆ C ˆ SH HC ˆ C ˆ (S ¨ O)R and HC ˆ C ˆ SO2R HC ˆ C ˆ NR3

0.95 1.05 1.00 1.05 1.10 1.10 1.10 1.15 1.15 1.15 1.20 1.20 1.20 1.25 1.25 1.30 1.30 1.30

1.20 1.45 1.35 1.55 1.50 1.50 1.50 1.55 1.70 1.55 1.50 1.50 1.50 1.65 1.60 1.55 1.60 1.60

1.55 1.70 1.70 1.95 1.80 1.90 1.80 1.90 1.90 1.80 1.75 1.75 1.80 2.00 1.90 2.00 1.80 1.65

1.35 1.40

1.70 1.75

2.05

6.77

SPECTROSCOPY

TABLE 6.34 Proton Chemical Shifts (continued) Substituent group

Methyl protons

HC ˆ C ˆ O ˆ N ¨ O HC ˆ C ˆ O(C ¨ O)CF3 HC ˆ C ˆ Cl HC ˆ C ˆ F HC ˆ C ˆ NO2 HC ˆ C ˆ O(C ¨ O)Ar HC ˆ C ˆ I HC ˆ C ˆ Br HC ˆ CH2 HC ˆ C ¨ C HC ˆ C ˜ C HC ˆ (C ¨ O)OR HC ˆ (C ¨ O)NR2 HC ˆ SR HC ˆ O ˆ O HC ˆ (C ¨ O)R HC ˆ C ˜ N HC ˆ I HC ˆ CHO HC ˆ Ar HC ˆ NR2 HC ˆ SSR HC ˆ (C ¨ O)Ar HC ˆ SAr HC ˆ NRAr HC ˆ SO2R and HC ˆ (SO)R HC ˆ Br HC ˆ NR3 HC ˆ NH(C ¨ O)R HC ˆ SO3R HC ˆ Cl HC ˆ OH and HC ˆ OR HC ˆ PAr3 HC ˆ NH2 HC ˆ O(C ¨ O)R HC ˆ OAr HC ˆ O(C ¨ O)Ar HC ˆ O(C ¨ O)CF HC ˆ F HC ˆ NO2 Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane

1.40 1.40 1.55 1.55 1.60 1.65 1.75 1.80 0.90 1.60 1.70 2.00 2.00 2.05 2.10 2.10 2.15 2.15 2.20 2.25 2.25 2.35 2.40 2.40 2.60 2.60 2.70 2.95 2.95 2.95 3.05 3.20 3.20 3.50 3.65 3.80 3.80 3.95 4.25 4.30

Methylene protons

1.65 1.80 1.85 2.05 1.75 1.80 1.85 1.30 2.05 2.20 2.25 2.25 2.55 2.30 2.35 2.45 3.15 2.40 2.45 2.40 2.70 2.70

Methine proton

1.95 2.15 2.50 1.85 2.10 1.90 1.50 2.80 2.50 2.40 3.00 2.55 2.65 2.90 4.25 2.85 2.80 3.40

3.10 3.05 3.40 3.10 3.35

3.60

3.45 3.40 3.40 3.75 4.10 4.00 4.20 4.30 4.50 4.35 0.20 2.45 1.65 1.50 1.25

4.05 3.60

4.10 3.60 3.85

4.05 4.95 4.60 5.05 4.80 4.60 0.40

1.80

6.78

SECTION 6

TABLE 6.34 Proton Chemical Shifts (continued)

Substituent group

Proton shift

Substituent group

Proton shift

HC ˜ CH HC ˜ CAr HC ˜ C ˆ C ¨ C HAr HCO ˆ O HCO ˆ R HCO ˆ Ar HO ˆ N ¨ C (oxime)

2.35 2.90 2.75 7.20 8.1 9.4–10.0 9.7–10.5 9–12

HO ˆ C ¨ O HO ˆ SO2 HO ˆ Ar HO ˆ R HS ˆ Ar HS ˆ R HN ˆ Ar HN ˆ R

10–12 11–12 4.5–6.5 0.5–4.5 2.8–3.6 1–2 3–6 0.5–5

Saturated heterocyclic ring systems

1.8

1.6 2.7

3.7

O

2.2

1.9

2.8

2.8

N H

S

S

2.0 1.6

O

1.5 1.6

1.5

3.6

2.7

O

2.6

S

N H

1.9

H N

2.2–2.5 2.2

O

O

1.6

2.9

3.4

N H

O

2.6

1.8

4.3

O

1.5–1.9

N H 0.0

3.6

O

O

7.7 3.3 4.1

O

O

R 3.2

N H 8.1

O

H 4.7– 4.9

O

2.3 3.9 – 4.1

O

S

6.79

SPECTROSCOPY

TABLE 6.34 Proton Chemical Shifts (continued) Substituent group

Methyl protons

Methylene protons

Methine proton

Unsaturated cyclic systems

TABLE 6.35 Estimation of Chemical Shift for Protons of ˆ CH2 ˆ and aCH ˆ Groups CH2  0.23  C1  C2

X* ˆ CH3 ˆ CF3 aC ˆ Cb ˆC˜CˆR ˆ COOR ˆ NR2 ˆ CONR2

CH  0.23  C1  C2  C3

C 0.5 1.1 1.3 1.4 1.5 1.6 1.6

X* ˆ SR ˆ C ˜ C ˆ Ar ˆ CN ˆ CO ˆ R ˆI ˆ Ph ˆ Br

*R, alkyl group; Ar, aryl group; Ph, phenyl group.

C 1.6 1.7 1.7 1.7 1.8 1.8 2.3

X*

C

ˆ OR ˆ Cl ˆ OH ˆN¨C¨S ˆ OCOR ˆ OPh

2.4 2.5 2.6 2.9 3.1 3.2

6.80

SECTION 6

TABLE 6.36 Estimation of Chemical Shift of Proton Attached to a Double Bond Positive Z values indicate a downfield shift, and an arrow indicates the point of attachment of the substituent group to the double bond.

R

Zgem, ppm

Zcis, ppm

Ztrans, ppm

→H →alkyl →alkyl ˆ ring (5- or 6-member) →CH2O ˆ →CH2S ˆ →CH2X (X: F, Cl, Br) →CH2Nb ] C ¨ C (isolated) c

0 0.45 0.69 0.64 0.71 0.70 0.58 1.00

0 0.22 0.25 0.01 0.13 0.11 0.10 0.09

0 0.28 0.28 0.02 0.22 0.04 0.08 0.23

] c

C ¨ C (conjugated) →C ˜ N →C ˜ C ˆ ] C ¨ O (isolated) c

1.24 0.27 0.47 1.10

0.02 0.75 0.38 1.12

0.05 0.55 0.12 0.87

] c

1.06 0.97 0.80 0.80 0.78

0.91 1.41 0.98 1.18 1.01

0.74 0.71 0.32 0.55 0.46

1.02

0.95

1.17

1.37

0.98

0.46

1.11

1.46

1.01

1.22 1.21 2.11

1.07 0.60 0.35

1.21 1.00 0.64

0.69

0.08

0.06

1.05 1.54 1.08 1.07 1.14 0.80

0.29 0.40 0.18 0.45 0.81 1.26

0.32 1.02 0.13 0.55 0.88 1.21

C ¨ O (conjugated) →COOH (isolated) →COOH (conjugated) →COOR (isolated) →COOR (conjugated)

→OR (R: aliphatic) →OR (R: conjugated) →OCOR

→CH2 ˆ aromatic ring →F →Cl →Br →I →N ˆ R (R: aliphatic)

6.81

SPECTROSCOPY

TABLE 6.36 Estimation of Chemical Shift of Proton Attached to a Double Bond (continued ) R

→aromatic →CF3 →aromatic (o-substituted) →SR →SO2

Zgem, ppm

Zcis, ppm

Ztrans, ppm

1.17

0.53

0.99

2.08 1.38 0.66 1.65 1.11 1.55

0.57 0.36 0.61 0.19 0.29 1.16

0.72 0.07 0.32 0.09 0.13 0.93

TABLE 6.37 Chemical Shifts in Monosubstituted Benzene   7.27  i

Substituent

ortho

meta

NO2 CHO COOH COOCH3 COCl CCl3 COCH3 CN CONH 2 + N H3 CH2X* CH3 CH2CH3 CH(CH3)2 C(CH3)2 F Cl Br I NH2 OCH3 OH OCOR NHCH3 N(CH3)2

0.94 0.58 0.80 0.71 0.82 0.8 0.62 0.26 0.65 0.4 0.0–0.1 0.16 0.15 0.14 0.09 0.30 0.01 0.19 0.39 0.76 0.46 0.49 0.2 0.8 0.60

0.18 0.20 0.16 0.08 0.21 0.2 0.10 0.18 0.20 0.2 0.0–0.1 0.09 0.06 0.09 0.05 0.02 0.06 0.12 0.25 0.25 0.10 0.13 0.1 0.3 0.10

*X  Cl, alkyl, OH, or NH2.

para 0.39 0.26 0.25 0.20 0.35 0.2 0.25 0.30 0.22 0.2 0.0–0.1 0.17 0.18 0.18 0.23 0.23 0.08 0.05 0.02 0.63 0.41 0.2 0.2 0.6 0.62

6.82

SECTION 6

TABLE 6.38 Proton Spin Coupling Constants Structure

J, Hz

12–15

Structure

J, Hz cis (Z) trans (E) gem

6–8 5 4–8 6–8

1–3

8–16 0–3 gem cis (Z)

6–14 11–18

8–10 2–3 2–3

trans (E) cis (Z) trans (E) gem

0.5–3 0.5–3 4–10 10–13 6

cis (Z) trans (E) gem cis (Z) trans (E) gem

0–3 0–3 0–2 2–4 5–7 6–9 10–13 4–5 3 5–6 0 7 6

2 6 4 1.8 3.5 0–1 1–2 5–6 3.5–5.0 1.5 3.4 6–12 4–8 1.5–2.5 2.5 1.5 0

Cyclopentane cis (Z) trans (E) Cyclobutane cis (Z) trans (E) Cyclopropane cis (Z) trans (E) gem

4–6 4–6 8 8 9–11 6–8 4–6 6–10 1–3 0–1

8–9 6 5–6 7–9 1–2 1–2 0–1 0–1

6.83

SPECTROSCOPY

TABLE 6.38 Proton Spin Coupling Constants (continued) Structure

J, Hz

Structure

J, Hz gem cis (Z) trans (E)

2–3 2–3 2–3 3–4 1–2 1–3

72–90 3 to 20 12–40 2–4

45–52

0–6 21 34 12

gauche trans (Z)

 5–8

0–12 10–45

TABLE 6.39 Carbon-13 Chemical Shifts Values given in ppm on the  scale, relative to tetramethylsilane Primary carbon

Secondary carbon

Tertiary carbon

Quaternary carbon

Alkanes CˆC CˆO CˆN CˆS C ˆ halide (I to Cl)

5–30 45–60 13–45 10–30 3–25

25–45 42–71 44–58 22–42 3–40

23–58 62–78 50–70 55–67 34–58

28–50 73–86 60–75 53–62 35–75

Substituent group

, ppm

Substituent group

, ppm

Cyclopropane Cycloalkane C4–C10 Mercaptanes Amines R2N ˆ C Aryl ˆ N Sulfoxides, sulfones Thiocyanates R ˆ SCN Alkenes H2C ¨ R2C ¨

5–5 5–25 5–70

Alcohols R ˆ OH Ethers R ˆ O ˆ R Nitro R ˆ NO2 Alkynes HC ˜ CR RC ˜ CR Acetals, ketals Esters Saturated ,-Unsaturated Isocyanides R ˆ NC

45–87 57–87 60–78

Substituent group

20–70 128–138 35–55 96–118 100–122 110–150

63–73 72–95 88–112 158–165 165–176 162–175

6.84

SECTION 6

TABLE 6.39 Carbon-13 Chemical Shifts (continued ) Substituent group Heteroaromatics C¨N C Cyanates R ˆ OCN Isocyanates R ˆ NCO Isothiocyanates R ˆ NCS Nitriles, cyanides Aromatics Aryl-C Aryl-P Aryl-N Aryl-O Azomethines Carbonates Ureas Anhydrides Amides Oximes

, ppm

100–152 142–160 105–120 115–135 115–142 117–124 125–145 119–128 128–138 133–152 145–162 159–162 150–170 150–175 154–178 155–165

Substituent group Carboxylic acids Nonconjugated Conjugated Salts (anion) Ketones -Halo Nonconjugated ,-Unsaturated Imides Acyl chlorides R ˆ CO ˆ Cl Thioureas Aldehydes -Halo Nonconjugated Conjugated Thioketones R ˆ CS ˆ R Carbonyl M(CO)n Allenes ¨ C ¨

Saturated heterocyclic ring systems

, ppm

162–165 165–184 175–195 160–200 192–202 202–220 165–180 165–183 165–185 170–190 182–192 192–208 190–202 190–218 197–205

6.85

SPECTROSCOPY

TABLE 6.39 Carbon-13 Chemical Shifts (continued ) Unsaturated cyclic systems CH2 107.1

149.7

30.2

130.8

137.2

36.2

127.3

32.6

28.9

24.5

22.1

22.1

26.9

128.1 165.1

150.7

133.8

125.9

129.3

O

O

133.7

126.3 126.3

128.3 132.6

130.1

122.2 125.5

131.9 126.6

132.2

121.7

112.9

106.2

110.9

109.6

130.1 108.0 153.3

152.2 142.7

141.2

105.9

108.1

129.0

124.7

136.4

139.0 124.4

CHO

N H

12.4

128.1

126.4

143.2 134.0

CH3

N H

N H

178.2

123.0

112.0

118.4

CHO

O

13.4

127.2 116.7

148.5

CH3

O

O

142.4

122.6

S

S

122.3

N

CHO

S

182.8

118.5

152.2

N

122.1

127.6

N H

159.3

157.4

N

121.3

N

152.8

136.2

122.3

S

14.8

157.4

N

143.4 134.6

CH3

128.8 102.6

122.3 125.2

N

N

120.3

145.6

N

111.8

N H 136.1

122.8

127.6 111.4

128.3

128.7 136.0

126.8

121.2

126.8 121.5

130.5

150.9

127.5

144.7 124.2

O 106.5 155.1

129.7 130.1

N 149.0

136.0 120.8 143.8

N 127.9

153.1 129.0

6.86

SECTION 6

TABLE 6.39 Carbon-13 Chemical Shifts (continued ) Saturated alicyclic ring systems

TABLE 6.40 Estimation of Chemical Shifts of Alkane Carbons Relative to tetramethylsilane Positive terms indicate a downfield shift. C  2.6  9.1n  9.4n  2.5n  0.3n  0.1n (plus any correction factors) where n is the number of carbons bonded directly to the ith carbon atom and n, n, n, and nε are the number of carbon atoms two, three, four, and five bonds removed. The constant is the chemical shift for methane. Chain branching* 1(3) 1(4) 2(3) 3(2)

Correction factor 1.1 3.4 2.5 3.7

Chain branching*

Correction factor

4(1) 2(4) 3(3) 4(2)

1.5 7.2 9.5 8.4

*1 signifies a CH3 ˆ group; 2, a ˆ CH2 ˆ group; 3, a aCH ˆ group; and 4, a aCb group. 1(3) signifies a methyl group bound to a aCH ˆ group, and so on. Examples: For 3-methylpentane, CH3 ˆ CH2 ˆ CH(CH3) ˆ CH2 ˆ CH3, C  2  2.6  9.1(2)  9.4(2)  2.5  1(1)[2(3)]  29.4 C  3  2.6  9.1(3)  9.4(2)  (2)[3(2)]  36.2

6.87

SPECTROSCOPY

TABLE 6.41 Effect of Substituent Groups on Alkyl Chemical Shifts

These increments are added to the shift value of the appropriate carbon atom as calculated from Table 6.40.

 carbon Substituent group Y*

 carbon

Straight

Branched

Straight

Branched

20.9 24.4 20.5 33 22 31 30 48.3 58 51 51 53 68 31.2 20.0 8 29.3 26 36.9 42 31 63 4 11 20 20 23 4.5

16 20 17 28 2.5

2.5 4.1 2.5

2 3 2 2

ˆ CO ˆ OH ˆ COO (anion) ˆ CO ˆ OR ˆ CO ˆ Cl ˆ CO ˆ NH2 ˆ CHO ˆ CO ˆ R ˆ OH ˆ OR ˆ O ˆ CO ˆ NH2 ˆ O ˆ CO ˆ R ˆ C ˆ CO ˆ Ar ˆF ˆ Cl ˆ Br ˆI ˆ NH2 ˆ NH3 ˆ NHR ˆ NR2 ˆ NR3 ˆ NO2 ˆ CN ˆ SH ˆ SR ˆ CH ¨ CH2 ˆ C6H5 ˆ C ˜ CH *R, alkyl group; Ar, aryl group.

24 40.8 51 45 63 32 25 4 24 24 31

57 1 11

17

0 1 10.2 8 8 6 9 10.5 10.6 11.3 11.3 8 8.3 6 5 4 3 12 7 6 9 5.5

 carbon 2.2 1.6 2

1 7.7 5

0.5 2 2 5.8 4

5

3

6 10 10 12 10 6 6

4 4.6 3.1 1.0 4.6 5 3.5 3 7

4 3 11

7

3 6 3 0.5 2 3.5

6.88

SECTION 6

TABLE 6.42 Estimation of Chemical Shift of Carbon Attached to a Double Bond The olefinic carbon chemical shift is calculated from the equation C  123.3  10.6n  7.2n  7.9n  1.8n (plus any steric correction terms) where n is the number of carbon atoms at the particular position, namely,     CˆC¨CˆC Substituents on both sides of the double bond are considered separately. Additional vinyl carbons are treated as if they were alkyl carbons. The method is applicable to alicyclic alkenes; in small rings carbons are counted twice, that is, from both sides of the double bond where applicable. The constant in the equation is the chemical shift for ethylene. The effect of other substituent groups is tabulated below. Substituent group ˆ OR ˆ OH ˆ O ˆ CO ˆ CH3 ˆ CO ˆ CH3 ˆ CHO ˆ CO ˆ OH ˆ CO ˆ OR ˆ CN ˆF ˆ Cl ˆ Br ˆI ˆ C6H5

 2 6 3

1 0



29

39

18 15 13.6 5.2 6 15.4 24.9 3.3 7.2 37.4 12

27 6 13.2 9.1 7 14.3 34.3 5.4 0.7 7.7 11 Steric correction term

Substituent pair , , ,  , ,



trans (E ) cis (Z ) gem

0 1.1 4.8 2.5 2.3

 1 1 4

2 2

6.89

SPECTROSCOPY

TABLE 6.43 Carbon-13 Chemical Shifts in Substituted Benzenes C  128.5 

Substituent group ˆ CH3 ˆ CH2CH3 ˆ CH(CH3)2 ˆ C(CH3)3 ˆ CH2O ˆ CO ˆ CH3 ˆ C6H5 ˆ CH ¨ CH2 ˆ C ˜ CH ˆ CH2OH ˆ CO ˆ OH ˆ COO (anion) ˆ CO ˆ OCH3 ˆ CO ˆ CH3 ˆ CHO ˆ CO ˆ Cl ˆ CO ˆ CF3 ˆ CO ˆ C6H5 ˆ CN ˆ OH ˆ OCH3 ˆ OC6H5 ˆ O ˆ CO ˆ CH3 ˆ NH2 ˆ N(CH3)2 ˆ N(C6H5)2 ˆ NHC6H5 ˆ NH ˆ CO ˆ CH3 ˆ NO2 ˆF ˆ Cl ˆ Br ˆI ˆ CF3 ˆ NCO ˆ SH ˆ SCH3 ˆ SO2 ˆ NH2 ˆ Si(CH3)3

C  1

ortho

meta

para

9.3 15.6 20.2 22.4 7.7 13.1 9.5 6.1 12.3 2.1 8 2.1 9.1 8.6 4.6 5.6 9.4 15.4 26.9 31.4 29.2 23.0 18.0 22.4 19 14.6 11.1 20.0 34.8 6.2 5.5 32.2 9.0 5.7 2.3 10.2 15.3 13.4

0.8 0.4 2.5 3.1 0 1.1 2.0 3.8 1.4 1.5 1 1.1 0.1 1.3 2.4 1.8 1.7 3.6 12.7 14.0 9.4 6.4 13.3 15.7 4 10.7 9.9 4.8 12.9 0.4 3.4 9.9 2.2 3.6 1.1 1.8 2.9 4.4

0.1 0 0.1 0.1 0 0.4 0.2 0.4 1.4 0 0 0.1 0 0.6 1 0.7 0.2 0.6 1.4 1.0 1.6 1.3 0.9 0.8 1 0.7 0.2 0.9 1.4 1.3 1.7 2.6 0.3 1.2 1.1 0.4 0.4 1.1

2.9 2.6 2.4 2.9 0 1.2 0.5 0.2 1.4 5.1 3 4.5 4.2 5.5 6.2 6.7 3.6 3.9 7.3 7.7 5.1 2.3 9.8 11.5 6 7.7 5.6 5.8 4.5 1.9 1.6 1.4 3.2 2.8 3.1 3.6 3.3 1.1

6.90

SECTION 6

TABLE 6.44 Carbon-13 Chemical Shifts in Substituted Pyridines* c(k)  Ck  i

Substituent group

C2  C6  149.6

C  2 or C  6

ˆ CH3 ˆ CH2CH3 ˆ CO ˆ CH3 ˆ CHO ˆ OH ˆ OCH3 ˆ NH2 ˆ NO2 ˆ CN ˆF ˆ Cl ˆ Br

9.1 14.0 4.3 3.5 14.9 15.3 11.3 8.0 15.8 14.4 2.3 6.7

Substituent group

32

ˆ CH3 ˆ CH2CH3 ˆ CO ˆ CH3 ˆ CHO ˆ OH ˆ NH2 ˆ CN ˆ Cl ˆ Br ˆI

Substituent group ˆ CH3 ˆ CH2CH3 ˆ CH ¨ CH2 ˆ CO ˆ CH3 ˆ CHO ˆ NH2 ˆ CN ˆ Br

23

24

25

1.0 2.1 2.8 2.6 17.2 13.1 14.7 5.1 5.0 14.7 0.7 4.8

0.1 0.1 0.7 1.3 0.4 2.1 2.3 5.5 1.7 5.1 3.3 3.3

3.4 3.1 3.0 4.1 3.1 7.5 10.6 6.6 3.6 2.7 1.2 0.5

C3  C5  124.2

C  3 or C  5

1.3 0.3 0.5 2.4 10.7 11.9 3.6 0.3 2.1 7.1

9.0 15.0 0.3 7.9 31.4 21.5 13.7 8.2 2.6 28.4

42  46 0.5 0 0.3 1.6 1.7 0.9 2.1 3.0

34

35

0.2 1.5 3.7 0 12.2 14.2 4.4 0.2 2.9 9.1

0.8 0.3 2.7 0.6 1.3 0.9 0.6 0.7 1.2 2.4

43  45 0.8 0.3 2.9 2.6 0.6 13.8 2.2 3.4

26 0.1 0.2 0.2 0.7 6.8 2.2 0.9 0.4 1.9 1.7 0.6 1.4

2.3 1.8 4.2 5.4 8.6 10.8 4.2 1.4 0.9 0.3 C4  136.2

C  4 10.8 15.9 8.6 6.8 5.5 19.6 15.7 3.0

*May be used for disubstituted, polyheterocyclic, and polynuclear systems if deviations due to steric and mesomeric effects are allowed for.

6.91

SPECTROSCOPY

TABLE 6.45 Carbon-13 Chemical Shifts of Carbonyl Group

X

Y

C

X CH3 ˆ CH3 ˆ CH3 ˆ

ˆ CH ¨ CH2 ˆ C6H5 ˆ CH2 ˆ CO ˆ CH3

CH3 ˆ CH3 ˆ

ˆ CH2CHO ˆ C6H5 ˆ CH3

CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ CH3 ˆ

ˆ 2,6-(CH3)2C6H5 ˆ OH ˆ O (anion) ˆ OCH3 ˆ O ˆ CH ¨ CH2 ˆ O ˆ CH(CH3)2 ˆ O ˆ CO ˆ CH3 ˆ NH2 ˆ NHCH3 ˆ N(CH3)2 ˆ Cl ˆ Br ˆI

Hˆ Hˆ Hˆ

ˆ CH3 ˆ CCl3 ˆ NH2

199.7 175.3 165.5

Hˆ

ˆ N(CH3)2

162.4

Hˆ Hˆ Hˆ (CH3)2CH ˆ C6H5 ˆ CF3 ˆ CCl3 ˆ CH3CH(NH2) ˆ CF3 ˆ H2N ˆ 2-Furyl (CH3)2N ˆ CH2 ¨ CHCH2O CO ˆ CH3CH2 ˆ CH3 ˆ CH2 ˆ CH3 ˆ CH3 ˆ

2-Furyl 2-Pyrrolyl 2-Thienyl ˆ OH ˆ OH ˆ OH ˆ OH ˆ OH ˆ OCH2CH3 ˆ OCH2CH3 ˆ OCH3 ˆ C6H5

153.3 134.0 143.3 184.8 172.6 163.0 168.0 176.5 158.1 157.8 159.1 170.8

ˆ OCH2CH ¨ CH2 ˆ CH2CH3 ˆ O ˆ CO ˆ CH2CH3 ˆ CH3 ˆ CH2CH3

157.6 211.4 170.3 205.8 207

n

C

3 4 5 6 7

207.9 218.2 211.3 211.4 216.0

Y

C 196.9 197.6 201.9 (keto) 191.4 (enol) 167.7 196 (m, p) 199 (o) 206 178 181.5 170.7 167.7 170.3 167.3 172.7 172 169.5 169.6 165.6 158.9

6.92

SECTION 6

TABLE 6.46 One-Bond Carbon–Hydrogen Spin Coupling Constants Structure

JCH, Hz

H ˆ CH3 H ˆ CH2CH3 CH3 ˆ CH2 ˆ CH3 H ˆ C(CH3)2 H ˆ CH2CH2OH H ˆ CH2CH ¨ CH2 H ˆ CH2C6H5 H ˆ CH2C ˜ CH H ˆ CH2CN H ˆ CH(CN)2 H ˆ CH2 ˆ halogen H ˆ CHF2 H ˆ CHCl2 H ˆ CH2NH2 H ˆ CH2NH3 H ˆ CH2OH (or H ˆ CH2OR) H ˆ CH(OR)2 H ˆ C(OR)3 H ˆ C(OH)R2 H ˆ CH2NO2 H ˆ CH(NO2)2 H ˆ CH2COOH H ˆ CH(COOH)2 H ˆ CH ¨ CH2 H ˆ C(CH3) ¨ C(CH3)2 H ˆ CH ¨ C(tert-C4H9)2 H ˆ C(tert-C4H9) ¨ C(tert-C4H9)2 Methylenecycloalkane C4–C7 H ˆ CH ¨ C ¨ CH2 H ˆ C(C6H5) ¨ CH(C6H5) cis (Z ) trans (E) Cyclopropene

125.0 124.9 119.2 114.2 126.9 122.4 129.4 132.0 136.1 145.2 149–152 184.5 178.0 133.0 145.0 140–141 161–162 186 143 146.0 169.4 130.0 132.0 156.2 148.4 152

gem

143 153–155 168 155 151 220 200

Structure

JCH, Hz gem cis (Z)

177 163

trans (E)

165

cis (Z)

163

trans (E)

177

H ˆ CH ¨ O; CH3 ˆ CH ¨ O H2N ˆ CH ¨ O (CH3)2N ˆ CH ¨ O H ˆ COOH H ˆ COO (anion) H ˆ CO ˆ OCH3 H ˆ CO ˆ F CH3CH2 ˆ O ˆ CHO Cl3 ˆ CHO H ˆ C ˜ CH H ˆ C ˜ CCH3 H ˆ C ˜ CC6H5 H ˆ C ˜ CCH2OH H ˆ CN Cyclopropane Cyclobutane Cyclopentane Cyclohexane Tetrahydrofuran 2,5 3,4 1,4-Dioxane Benzene Fluorobenzene 2,6 3,5 4 Bromobenzene 2,6 3,5

172 188.3 191 222 195 226 267 225.6 207 249 248 251 241 269 161 136 131 123 149 133 145 159 155 163 161 171 164

cis (Z)

159

4

161

trans (E)

162

gem

195

Benzonitrile 2,6 3,6 4 Nitrobenzene 2,6 3,5 4 Mesitylene 2,6 3,5 4

173 166 163 171 167 163 154 170 163 152

cis (Z) trans (E)

163 161

gem

162

cis (Z) trans (E)

157 162

6.93

SPECTROSCOPY

TABLE 6.46 One-Bond Carbon–Hydrogen Spin Coupling Constants (continued ) Structure

JCH, Hz

2,4,6-Trimethylpyridine

Structure

JCH, Hz

158

2,5 3,4

183 170

2,5 3,4

201 175

2,5 3,4

185 167

3,5 4

190 178

2 4

208 199

205

216

TABLE 6.47 Two-Bond Carbon–Hydrogen Spin Coupling Constants Structure

2

CH3 ˆ CH2 ˆ H CCl3 ˆ CH2 ˆ H ClCH2 ˆ CH2Cl Cl2CH ˆ CHCl2 CH3 ˆ CHO CH2 ¨ CH2 (CH3)2C ¨ O CH2 ¨ CH ˆ CH ¨ O (C2H5)2CH ˆ CHO H2NCH ¨ CH ˆ CHO H2NCH ˆ CH ˆ CHO C6H6

4.5 5.9 3.4 1.2 26.7 2.4 5.5 26.9 26.9 6.0 20.0 1.0

JCH, Hz

2

Structure

JCH, Hz

n4 n5 n6

4.2 5.2 5.5

cis (Z ) trans (E )

16.0 0.8 49.3 61.0 33.2 32.5 35.3 46.3 10.8

HC ˜ CH C6H5O ˆ C ˜ CH HC ˜ C ˆ CHO ClCH2 ˆ CHO Cl2CH ˆ CHO Cl3C ˆ CHO C6H5 ˆ C ˜ C ˜ CH3

TABLE 6.48 Carbon–Carbon Spin Coupling Constants Structure*

JCC, Hz

H3C ˆ CH3 H3C ˆ CHR2 H3C ˆ CH2Ar H3C ˆ CH2CN H3C ˆ CH2 ˆ CH2OH C-1, C-2 C-2, C-3

35 37 34 33 38 34

Structure*

JCC, Hz

H3C ˆ CH2NH2 CˆC¨O CˆCˆC¨O C ˆ C ˆ Ar C ˆ CO ˆ O (anion) C ˆ CO ˆ N C ˆ CO ˆ OH

37 38–40 36 43 52 52 57

6.94

SECTION 6

TABLE 6.48 Carbon–Carbon Spin Coupling Constants (continued) Structure*

JCC, Hz

C ˆ CO ˆ OR C ˆ CN C ˆ C ˜ C 2JCC  11.8 H2C ¨ CH2 aC ¨ C ˆ CO ˆ OH aC ¨ C ˆ CN aC ¨ C ˆ Ar C6H6 C6H5NO2 1–2 2–3, 3–4 3 J2–5 C6H5I 1–2 2–3 3–4 3 J2–5 C6H5 ˆ OCH3 2–3 3–4

59 52–57 67 68 70–71 71 67–70 57 55 56 7.6 60 53 58 8.6 58 56

Structure* C6H5NH2 1–2 2–3 3–4 3 J2–5 C6H5CH3 Pyridine 2–3 3–4 3 J2–5 Furan Pyrrole Thiophene H2C ¨ C ¨ C(CH3)2 ˆC˜Cˆ Structure CH3 ˆ CO ˆ CH3 CH3 ˆ C ˜ CH CH3CH2 ˆ CN

JCC, Hz

61 58 57 7.9 44 54 56 14 69 69 64 100 170–176 2

JCC, Hz 16 11.8 33

* R, alkyl group; Ar, aryl group.

TABLE 6.49 Carbon–Fluorine Spin Coupling Constants Structure*

JCF, Hz

Structure*

158

JCF, Hz

271

165 235

274

259

F ˆ CH2CH2 ˆ or F ˆ CR3 p-F ˆ C6H4 ˆ OR p-F ˆ C6H4 ˆ R p-F ˆ C6H4 ˆ CF3 p-F ˆ C6H4 ˆ CO ˆ CH3 p-F ˆ C6H4 ˆ NO2 F ˆ C6H5 2 JCF  21.0 3 JCF  7.7 4 JCF  3.4

167 237 241 252 253 257 244

6.95

SPECTROSCOPY

TABLE 6.49 Carbon–Fluorine Spin Coupling Constants (continued ) Structure*

Structure*

JCF, Hz

JCF, Hz

287

241

308

278

353

265

369

289

* Ar, aryl group; R, alkyl group.

TABLE 6.50 Carbon-13 Chemical Shifts of Deuterated Solvents Relative to tetramethylsilane

Solvent

Group

, ppm

Acetic-d3 acid-d1

Methyl Carbonyl Methyl Carbonyl Methyl Carbonyl

20.0 205.8 28.1 178.4 1.3 117.7 128.5 193 97 77 25.2 39.5 67 165.5 47–49 53.8 57.3 123.5 135.5 149.9

Acetone-d6 Acetonitrile-d3 Benzene-d6 Carbon disulfide Carbon tetrachloride Chloroform-d1 Cyclohexane-d12 Dimethyl sulfoxide-d6 1,4-Dioxane-d6 Formic acid-d1 Methanol-d4 Methylene chloride-d2 Nitromethane-d3 Pyridine-d5

Carbonyl

C3, C5 C4 C2, C6

6.96

SECTION 6

TABLE 6.51 Carbon-13 Spin Coupling Constants with Various Nuclei Nuclei

Structure

1

2

CDCl3 CD3 ˆ CO ˆ CD3 (CD3)2SO C6D6 CH3Li (C6H5)4B (CH3)4N CH3NC (CH3)4Si (CH3)3P (C4H9)3P (C6H5)3P (CH3)4P (C4H9)4P (C6H5)4P R(RO)2P  O (C4H9O)3P ¨ O (CH3)2Se (CH3)3Se (CH3)2Cd (CH3)4Sn (CH3)3SnC6H5 (CH3)2Te (CH3)2Hg (C6H5)2Hg (CH3)2Pb (C6H5)4Pb

32 20 22 26 15 49 10 8 52 14 11 12 56 48 88 142

H

7

Li B 14 N 11

29

Si P

31

77

Se

113 119

Cd Sn

125

Te 199 Hg 207

Pb

2

J, Hz

J, Hz

3

J, Hz

4

J, Hz

3

62 50 513, 537 340 474 162 687 1186 250 481

12 20

5 7

0

4 11 5–7 6

15 13

3

7

37

47

11

88

102

18

68

81

20

TABLE 6.52 Boron-11 Chemical Shifts Values given in ppm on the  scale, relative to B(OCH3)3

Structure

, ppm

R3B Ar3B BF3 BCl3 BBr3 BI3 B(OH)3 B(OR)3 B(NR2)3

67 to 68 43 24 12 6 41 36 0–1 13

Structure

, ppm

C6H5BCl2 C6H5B(OH)2 C6H5B(OR)2 M(BH4) B(BF4)

36 14 10 55–61 19–20

NH

BH

NH

BH

HB

NH

12

6.97

SPECTROSCOPY

TABLE 6.52 Boron-11 Chemical Shifts (continued) , ppm

Structure H

H B H

H B H

N R2 NR2

H B H

37

H

, ppm

Structure

7 to 8 23–24 74–82

R2O(or ROH) · BCl3 R2O(or ROH) · BBr3 R2O(or ROH) · BI3

15

24

B NR2

H

(CH3)2N ˆ B(CH3)2 Addition complexes R2O · BH3 R3N · BH3 R2NH · BH3

62 18–19 25 33

31 R2O(or ROH) · BF3

17–19

Boranes B2H6

1

B4H10 (BH2) (BH)

25 60 Base

B5H9 B5H11 B10H14

31 16 7

Apex 70 50 54

TABLE 6.53 Nitrogen-15 (or Nitrogen-14) Chemical Shifts Values given in ppm on the  scale, relative to NH3 liquid Substituent group Aliphatic amines Primary Secondary Tertiary Cyclo, primary Aryl amines Aryl hydrazines Piperidines, decahydroquinolines Amine cations Primary Secondary Tertiary Quaternary Enamines, tertiary type Alkyl Cycloalkyl Aminophosphines Amine N-oxides

, ppm

1–59 7–81 14–44 29–44 40–100 40–100 30–82 19–59 40–74 30–67 43–70 29–82 55–104 59–100 95–122

Substituent group Ureas Aliphatic Aryl Sulfonamides Amides HCO ˆ NHR R  primary R  secondary R  tertiary HCO ˆ NH ˆ Aryl RCO ˆ NHR or RCO ˆ NR2 RCO ˆ NH ˆ Aryl Aryl ˆ CO ˆ H ˆ Aryl Guanidines Amino Imino Thioureas Thioamides

, ppm

63–84 105–108 79–164

100–115 104–148 96–133 138–141 103–130 131–136 ca 126 30–60 166–207 85–111 135–154

6.98

SECTION 6

TABLE 6.53 Nitrogen-15 (or Nitrogen-14) Chemical Shifts (continued ) Substituent group Cyanamides R2N ˆ ˆ CN Carbodiimides Isocyanates Alkyl, primary Alkyl, secondary and tertiary Aryl Isothiocyanates Azides

Lactams Hydrazones Amino Imino Cyanates Nitrile N-oxides, fulminates Isonitriles Alkyl, primary Alkyl, secondary Aryl Nitriles Alkyl Aryl Thiocyanates Diazonium Internal Terminal

, ppm

12 to 38 175–200 95–120 14–32 54–57 ca 46 90–107 52–80 108–122 240–260 113–122 141–167 319–327 155–182 195–225 162–178 191–199 ca 180 235–241 258–268 265–280 222–230 315–322

Substituent group Diazo Internal Terminal Nitrilium ions Azinium ions Azine N-oxides Nitrones Imides Imimes Oximes Nitramines Amine ˆ NO2 Nitrates gem-Polynitroalkanes Nitro Aryl Alkyl Hetero, unsaturated Azoxy Azo Nitrosamines Nitrites Thionitrites Nitroso Aliphatic amines, NO Aryl

, ppm

226–303 315–440 123–150 185–220 230–300 270–285 170–178 310–359 340–380 252–280 328–355 310–353 310–353 350–382 372–410 354–367 330–356 504–570 222–250 525–550 555–582 720–790 535–560 804–913

6.99

SPECTROSCOPY

TABLE 6.53 Nitrogen-15 (or Nitrogen-14) Chemical Shifts (continued ) Substituent group

, ppm

Substituent group

, ppm

Saturated cyclic systems 35.5 n2 n3 n4 n5

8.5 25.3 36.7 37.7

7.5 (in C6H6) 18.0 (in H2O)

32.1

cis (Z ) trans (E ) Unsaturated cyclic systems

42.4 52.9

6.100

SECTION 6

TABLE 6.53 Nitrogen-15 (or Nitrogen-14) Chemical Shifts (continued ) Unsaturated cyclic systems (continued) N

N N

N

236

O

N H

S

N N

316

291

X

257

N

S

X

,ppm

O S Se

517 331 373 N

293

N 316 N

N

316

281

N

N 330

361

N

N

N

N

412

N

N

N H

283

N

N

N 114

N

280

308 301

N N H

N

N

399

N 351

261

TABLE 6.54 Nitrogen-15 Chemical Shifts in Monosubstituted Pyridine   317.3  i

Substituent ˆ CH3 ˆ CH2CH3 ˆ CH(CH3)2 ˆ C(CH3)3 ˆ CN ˆ CHO ˆ CO ˆ CH3 ˆ CO ˆ OCH2CH3 ˆ OCH3 ˆ OH ˆ NO2 ˆ NH2 ˆF ˆ Cl ˆ Br

C-2

0.4 1.8 5.1 2.5 0.9 10 9 11.8 49 126 23 45 42 4 2

C-3

0.3

0.8 11 15 0 2 1 10 18 4 8

C-4

8.0 6.6 5.9 5.8 10.6 29 11 5 23 118 22 46 6 7

6.101

SPECTROSCOPY

TABLE 6.55 Nitrogen-15 Chemical Shifts for Standards Values given in ppm, relative to NH3 liquid at 23 °C

Substance

, ppm

Conditions

Nitromethane (neat)

380.2

Potassium (or sodium) nitrate (saturated aqueous solution) C(NO2)4 (CH3)2 ˆ CHO (neat)

376.5

For organic solvents and acidic aqueous solutions For neutral and basic aqueous solutions For nitro compounds For organic solvents and aqueous solutions Saturated aqueous solution Saturated aqueous solution Saturated aqueous solution Saturated aqueous solution Liquid, 25 C Vapor, 5 atm

(C2H5)4NCl (CH3)4NCl NH4Cl NH4NO3 NH3

331 103.8 64.4 43.5 27.3 20.7 0.0 15.9

TABLE 6.56 Nitrogen-15 to Hydrogen-1 Spin Coupling Constants Structure

J, Hz

R ˆ NH2 and R2NH Aryl ˆ NH2 p-CH3O ˆ aryl ˆ NH2 p-O2N ˆ aryl ˆ NH2 Amine salts (alkyl and aryl) Aryl ˆ NHOH Aryl ˆ NHCH3 Aryl ˆ NHCH2F Aryl ˆ NHNH2 p-O2N ˆ aryl ˆ NHNH2 Aryl ˆ SO2 ˆ NH2 Aryl ˆ SO2 ˆ NHR

61–67 78 79 90–93 73–76 79 87 90 90 99 81 86 88

92–93

Structure

J, Hz

88–92 Pyrrole HC ˜ NH aP ˆ NH2 (R3Si)2NH CF3 ˆ S ˆ NH2 (CF3 ˆ S)2NH Pyridinium ion Quinolinium ion

97 133–136 82–90 67 81 99 90 96

6.102

SECTION 6

TABLE 6.57 Nitrogen-15 to Carbon-13 Spin Coupling Constants Structure

J, Hz

Structure

J, Hz

Alkyl amines Cyclic alkyl amines Alkyl amines protonated Aryl amines Aryl amines protonated CH3CO ˆ NH2 H2N ˆ CO ˆ NH2 Aryl ˆ NO2

4–4.5 2–2.5 4–5 10–14 9 14–15 20 15

Alkyl ˆ NO2 R ˆ CN  CH3 ˆ N ˜ C H3C ˆ N ˆN˜C Diaryl azoxy anti syn

11 18 10 9 18 13

TABLE 6.58 Nitrogen-15 to Fluorine-19 Spin Coupling Constants Structure

J, Hz

NF3 F4N2 FNO2 F3NO F3C ˆ O ˆ NF2 FCO ˆ NF2 (NF4)SbF6 (NF4)AsF6 (N2F)AsF6 F3C ˆ NO2 (2J  10)

Structure

155 164 158 190 164–176 221 323 328 459 215

Pyridine 2-F 3-F 2,6-di-F Pyridinium ion 2-F 3-F Quinoline, 8-F Aniline 2-F 3-F 4-F Anilinium ion 2-F 3-F 4-F 203

190

(2J  52)

J, Hz

52 4 37 23 3 3 0 0 1.5 1.4 0.2 0

TABLE 6.59 Fluorine-19 Chemical Shifts Values given in ppm on the  scale, relative to CCl3F Substituent group ˆ SO2 ˆ F ˆ CO ˆ F aN ˆ CO ˆ F Aryl ˆ CF2Cl ˆ CF2I ˆ CF2Br

, ppm 67 to 42 (aryl) (alkyl) 29 to 20 5 49 56 63

Substituent group R ˆ CF2Cl aC ˆ CF3 and aryl ˆ CF3 ˆ CS ˆ CF3 aCF ˆ CF3 ˆ S ˆ CF3 ˆ S ˆ CF2 ˆ S ˆ aP ˆ CF3

, ppm 61–71 56–73 70 71–73 41 39 46–66

6.103

SPECTROSCOPY

TABLE 6.59 Fluorine-19 Chemical Shifts (continued) Substituent group

, ppm

Substituent group

, ppm

aN ˆ CF3 aN ˆ CF2 ˆ C ˆ O ˆ CF2 ˆ R ˆ O ˆ CF2 ˆ CF3 ˆ CH2 ˆ CF3 HO ˆ CO ˆ CF3 ˆ CHF ˆ CF3 ˆ CF2 ˆ CF3 ˆ CS ˆ F CF3 ˆ C ˆ Nb ˆ CO ˆ CF2 ˆ CF3 ˆ CF2 ˆ ˆ CF2Br ˆ C ˆ CF2 ˆ S ˆ ˆ CF ¨ ˆ CF2 ˆ CF3 ˆ CO ˆ CF2 ˆ ˆ C(halide) ˆ CF2 ˆ ˆ CF2 ˆ CF3 ˆ CF2 ˆ CF2 ˆ ˆ CF2 ˆ CH2 ˆ ˆ CF2 ˆ CHF2 ˆ CF2H

40–58 85–127 70–91 70–91 76–77 77 81 78–88 81 84–96 83 86–126 91 91–98 180–192 111 116–131 119–128 121–125 121–129 122–133 128–132 136–143

Perfluorocycloalkane aCF ˆ CF3 aCF(CF3)2 ˆ CFH ˆ ˆ CFH2 F2C ¨ CF2

131–138 163–198 180–191 198–231 235–244 133

151–156

F2

F2 F2

F Cyclohexane-F

147

96–133

159 210 (axial) to 240 (equatorial)

cis (Z) trans (E) gem

F-1 F-2 F-3 ClFC ¨ CH ˆ CF3 Cycloalkenes ¨ CF ˆ CF2 ˆ C(CF3 or H) ˆ ˆ CF2 ˆ CF2 ˆ C(CF3 or CH3) ¨ ˆ CF2 ˆ CF2 ˆ CH ¨ ˆ CF2 ˆ CF2 ˆ CF ¨ Aryl ˆ F C10H7 ˆ F F-1 F-2 C6H5 ˆ C6H4 ˆ F F-2 F-3 F-4 C6F6

108 92 192

126 155 162 61

101–113 110–114 113–116 119–122 113 127 114 117 113 109 163

6.104

SECTION 6

TABLE 6.60 Fluorine-19 Chemical Shifts for Standards Substance

Formula

Trichlorofluoromethane ,,-Trifluorotoluene Trifluoroacetic acid Carbon tetrafluoride Fluorobenzene Perfluorocyclobutane

CFCl3 C6H5CF3 CF3COOH CF4 C6H5F C4F8

, ppm 0.0 63.8 76.5 76.7 113.1 138.0

TABLE 6.61 Fluorine-19 to Fluorine-19 Spin Coupling Constants Structure

JFF, Hz

F2C cycloalkane gem Unsaturated compounds aC ¨ Cb gem trans cis Aromatic compounds, monocyclic ortho meta para Alkanes CFCl2 ˆ CF2 ˆ CFCl2 CFCl2 ˆ CF2 ˆ CCl3 CF2Cl ˆ CF2 ˆ CF2Cl CF3 ˆ CF2 ˆ CF2Cl (or ˆ CF3) CF3 ˆ CF2 ˆ CF2Cl CF3 ˆ CF2 ˆ CF2Cl CF3 ˆ CF2 ˆ CF3

212–260 30–90 115–130 9–58 18–22 0–7 12–15 6 5 1 1 2 9 7

TABLE 6.62 Silicon-29 Chemical Shifts Values given in ppm on the  scale relative to tetramethylsilane n Substituent group X in (CH3)4  nSiXn ˆF ˆ Cl ˆ Br ˆI ˆH ˆ C2H5

1 35 30 26 9 19 2

2 9 32 20 34 42 5

3 52 13 18 18 65 7

4 109 19 94 346 93 8

6.105

SPECTROSCOPY

TABLE 6.62 Silicon-29 Chemical Shifts (continued) n Substituent group X in (CH3)4  nSiXn ˆ C6H5 ˆ CH ¨ CH2 ˆ Oalkyl ˆ Oaryl ˆ O ˆ CO ˆ alkyl ˆ N(CH3)2

1

2

3

4

5 7 14–17 17 22 6

9 14 3 to 6 6 4 2

12 21 41 to 45 54 43 18

23 79 to 83 101 75 28

, ppm

Structure Hydrides H3Si ˆ ˆ H2Si ˆ HSid Silicates Orthosilicate anions Silicon in end position Silicon in middle Branching silicons Cross-linked silicons Methyl siloxanes (CH3)2Si ˆ O ˆ (end position)

(middle)

(middle)

Structure

39 to 60 5 to 37 2 to 39

(branching)

69 to 72 77 to 81 85 to 89 93 to 97 107 to 120

, ppm

65 to 66

(cross-linked) 105 to 110 Polysilanes F3Si ˆ SiF3 74 Cl3Si ˆ SiCl3 (CH3O)3Si ˆ Si(OCH3)3 (CH3)3Si ˆ Si(CH3)3 (CH3)2Si[Si(CH3)3]2 HSi[Si(CH3)3]3 Si[Si(CH3)3]4

6–8 18 to 23

8 53 20 48 117 135

35 to 36

TABLE 6.63 Phosphorus-31 Chemical Shifts Values given in ppm on the  scale, relative to 85% H3PO4

Structure P4 PR3 PHR2 PH2R PH3 PF3 PRF2

Identical atoms attached directly to phosphorus

Non-identically substituted phosphorus R  CH3

R  C2H5

R  C6H5

62 99 164

20 56 128

6 41 122

168

207

461

241 97

6.106

SECTION 6

TABLE 6.63 Phosphorus-31 Chemical Shifts (continued)

Structure PCl3 PRCl2 PR2Cl PBr3 PRBr2 PR2Br PI3 P(CN)3 P(SiR3)3 P(OR)3 P(OR)2Cl P(OR)Cl2 P(SR)3 P(SR)2Cl P(SR)Cl2 P(SR)2Br P(SR)Br2 P(NR2)3 P(NR2)Cl2 PR(NR2)2 PR2(NR2) F2P ˆ PF2 Cl2P ˆ PCl2 I2P ˆ PI2 PH2K P(CF3)3 P4O6

Structure P(NCO)3 P(NCO)2X P(NCO)X2 P(NCS)3 P(NCS)2X P(NCS)X2 Structure

O ¨ PR3 O ¨ PHR2 O ¨ PF3

Identical atoms attached directly to phosphorus 220 227 178 136

226 155 170 255 3 113 Identical atoms attached directly to phosphorus 97 86

Identical atoms attached directly to phosphorus

Non-identically substituted phosphorus R  CH3

R  C6H5

192 94

196 119

162 81

184 91

194 116

152 71

251 141 169 114 125 188 206

139 165 177 115 186 211

204 123 166 86 39

127 157 173 132 183 204 184

118 162 100 62

151 100

Non-identically substituted phosphorus XF

128 131

X  Cl

X  Br

128 166

127

114 155

112 153

Non-identically substituted phosphorus R  CH3 36 63

36

R  C2H5

R  C2H5

R  C6H5

48

25 23

6.107

SPECTROSCOPY

TABLE 6.63 Phosphorus-31 Chemical Shifts (continued ) Identical atoms attached directly to phosphorus

Structure O ¨ PRF2 O ¨ PCl3 O ¨ PRCl2 O ¨ PR2Cl O ¨ P(OR)3 O ¨ P(OR)2Cl O ¨ P(OR)Cl2 O ¨ PH(OR)2 O ¨ PR2(OC2H5) O ¨ PR(OC2H5)2 O ¨ P(NR2)3 O ¨ PR2(NR2) O ¨ P(OR)2NH2 O ¨ P(OR)2(NCS) O ¨ P(SR)3 O ¨ PBr3 O ¨ P(NCO)3 O ¨ P(NCS)3 O ¨ P(NH2)3

PF5 PF6H PBr5 P(OC2H5)5 PO43 O ¨ P[OSi(CH3)3]3 H4P2O7 Phosphonates Phosphonium cations Alkyl Aryl (O3P ˆ PO3)4 Polyphosphates P

(end group)

R  C2H5

R  C6H5

27

29

11

45 65 1 6 6 19 50 30 23 44 15

53 77 1 3 6 15 52 33 24

34 43 18 6 2 31 17 2 26 3 29 55

12 19 61

66

35 144 101 71 6 33 11 24 to 2 43 to 32 35 to 18 9

O

(OR)2

R  CH3

103 41 62 22 Identical atoms attached directly to phosphorus

Structure

O

2

Non-identically substituted phosphorus

ca 6

Structure

Identical atoms attached directly to phosphorus

(middle group)

ca 18

(branch group)

ca 30

6.108

SECTION 6

TABLE 6.63 Phosphorus-31 Chemical Shifts (continued ) Identical atoms attached directly to phosphorus

Structure S ¨ PR3 S ¨ PCl3 S ¨ PRCl2 S ¨ PR2Cl S ¨ PBr3 S ¨ PRBr2 S ¨ PR2Br S ¨ P(OR)3 S ¨ P(OR)Cl2 S ¨ P(OR)2Cl S ¨ PH(OR)2 S ¨ P(SR)3 S ¨ P(NH2)3 S ¨ P(NR2)3 Se ¨ P(OR)3 Se ¨ P(SR)3 P(OR)5 PRF4 PR2F3

29

Non-identically substituted phosphorus R  CH3

R  C2H5

R  C6H5

59

55

43

80 87

94 109

75 80

21 64 73 59 73 74 98

42 98 68 56 68 69 92

20

82 78 82

78 71 76 71 30 6

112

60

30 9

53 54 59 59 92 58 86 42

TABLE 6.64 Phosphorus-31 Spin Coupling Constants Substituent group

JPH, Hz

Substituent group

JPH, Hz

aPH ˆ PH2 RPH2 aP ˆ CH3 aP ˆ CH2 ˆ

180–225 134 160–210 1–6 14

aP ˆ N ˆ CH aP ˆ C ˆ CH

8–25 0–4

H

H
C

P

P ortho meta

7–10 2–4

O ¨ PHR2 O ˆ PH(S)R O2PHR O2PH(N) O2PH(S or Se) O3PH H

210–500 490–540 500–575 560–630 630–655 630–760 490–650

S(or Se) ¨ PHR2

420–454

C H

   (Halogen)2P ¨ CH aP ˆ NH aP ˆ O ˆ CH3 aP ˆ O ˆ CH2 ˆ R aP ˆ O ˆ CHR2 aP ˆ SCH

12–22 30–40 14–20 16–20 10–28 11–15 6–10 3–7 5–20

S(or Se)

P

6.109

SPECTROSCOPY

TABLE 6.64 Phosphorus-31 Spin Coupling Constants Substituent group

JPH, Hz

Substituent group

7–15

JPH, Hz

axial

600–860

equatorial

800–1 000

15–30

110–113

15–30

980–1 190

9–18

2

11–15

JPB, Hz

Substituent group

12–17

80

490–600 Substituent group

JPP, Hz

aP ˆ F

1 320–1 420 (1F) (3F) 1 140–1 290 1 020–1 110 920–985 (alkyl) (aryl)

RPF2 R2PF RP(N)F

Substituent group P

P

220–400

O

P

P

O

S

P

P

S

1 225–1 305

1 310

1 100–1 200

JPP, Hz

330–500 15–500

P

C

P

ca 70

P

O

P

20–40

P

S

P

86–90

O

P

O

P

O

15–25

O

P

N H

P

O

8–30

P

N

P

N

60–90

ortho meta para

0–60 1–7 0–3

P

5–66

P

N

N

P

N

5–65

6.110

SECTION 6

ELECTRON SPIN RESONANCE Electron paramagnetic resonance (EPR) is also referred to as electron spin resonance (ESR). In many respects, it is similar to NMR and the corresponding principles, discussed in the previous section, apply. The critical difference is that an unpaired electron spin is detected in this method instead of a nuclear spin. The method applies only to paramagnetic systems. The electron spin is more readily detected than is a nuclear spin and magnets on EPR instruments are correspondingly smaller and less expensive. Certain transition metals such as cobalt (Co), copper (Cu), iron (Fe), manganese (Mn), nickel (Ni), and vanadium (V) have unpaired spins and are readily detectable by EPR. Likewise, organic radicals can be detected and studied. Numerous organic radicals have been studied by this method. When an unpaired electron spin is present, it will be observed at a characteristic resonance position. The resonance line is split by nuclei such as protons resulting in spin–spin coupling as observed in NMR. The coupling constant is referred to as “g” in EPR rather than “J ” as in NMR. It is referred to as the hyperfine splitting or hyperfine coupling constant. Certain radicals are especially stable and are of biological consequence or have been used as antioxidants. TEMPO radicals (TEMPO  2,2,6,6-tetramethylpiperidin-1-oxyl) have been particularly well studied because they are readily prepared and extremely stable.

NO2 N· N

O2 N

O = N· N

NO2

nitrous oxide radical

O.

TEMPO diphenylpicrylhydrazyl DPPH radical

A noticeable difference between NMR and EPR is that NMR is typically presented in absorption mode whereas EPR normally is presented in derivative mode. The EPR spectrum may be analyzed mathematically to determine the coupling pattern and thus the structural relationships. A database of software useful in EPR research is available at http://epr.niehs.nih.gov/software.html.

SPECTROSCOPY

TABLE 6.65 Spin–Spin Coupling (Hyperfine Splitting Constants) Values of coupling constant ai given in gauss Involves protons unless otherwise indicated.

6.111

6.112

SECTION 6

TABLE 6.65 Spin–Spin Coupling (Hyperfine Splitting Constants) (continued) 3.8

H

C

H

CH3

16.4

8.0

CH2

CH3

CH2

CH3

5.2 1.8 6.2

CH3 H

O H

15.2

C

OH

5.2

3.4

4.6

1.6

O

8.7

CH3

0.7

1.6

O

5.6

H C

4.7

3.7

4.3

2.7

3.1

1.3

0.9

1.1

0.7

0.2

6.6

6.5

5.9

6.7

C

C

0.5

CN O

CH3

3.9

O

C

CH3

O

CH3

C

2.2

2.6

0.7

0.4

1.2

NC

CH3

O

C 5.7

4.7

1.9

0.9

2.8

8.0

CN

4.7

0.5

0.5

2.9

2.7

CN

O C 1.3

NO2(14N) CH3

2.8

O C

1.7

C O

CH3

CH3

2.9 1.4

H

O

0.4

0.2

0.5

0.5

1.0

2.3

3.0

2.7

2.9

NO2

NO2

5.1

O

O

5.9

0.8

1.7

O

H3C

O

C

O

C

C CH3

0.8

C

5.9

O

1–2 1–2

CH3

CH2

12.0

CH2

CH3

H2C

O H3C

CH3

H3C

CH2

C

3.4

O

CH3

CH2

HC

5.7

C O

H3C

CH3

CH

H3C 1.5

C O

CH

CH3 H3C

CH3

O

H2C

6.5

CH2

8.7

10.2

C O

O

6.0

CH3

CH3 CH

3.7

CH3

14N

.

O

(14N) 14.3

.C14N (14N) 174

6.113

SPECTROSCOPY

TABLE 6.65 Spin–Spin Coupling (Hyperfine Splitting Constants) (continued)

10.0

NO2

32

NO2

3.4

NO2

0.4

–

4.2

4.0

1.1

– 0.1

1.6

–

1.0

1.6

NO2

4.2

4.7

14.9

NO2

tert-butyl

tert-butyl

2.5

NO2

17.8

NO2

1.1

H3C

tert-butyl

CH3

0.9

–

0.9

1.1

17.8

NO2

–

–

1.7

NO2

3.1

– 1.1

4.7

NO2

0.9

0.9

0.9 1.4

2.5

tert-butyl

N

1.7

NO2

12.2

NO2

3.3 3.4

N

–

–

(1H) 2.6 (14H) 7.1

–

1.1 1.1

N

N

1.1

H

H

1.1

H3C

1.1

CH3

N

0.7

(1H) 3.3 (14H) 7.6

+ N –

H C

4.4

C

N

0.8

C

C

137

0.8

C HOOC

CH3

C HOOC

17.1

CH2OH 10.1

H

OH C

HOOC

2.8

HO

HO OH

1–2.5

HO

0.8

2.0

3.9

O H

4.8 2.8

0.3

3.0

C

N

1.9

H

O

–

H 3.9

COOH

CH3

NO2

CH3

11.4

25.8

8.3

CH2

NO2

9.8

25.5

CH3

4.6

C

CH3 1.8

NO2 25.2

O R

H C

26.2 (anti) 29.2

6.2 (syn) 31.6

O

–

–

13.5 1.2

3.7

N O

O

33.0

7.5 10.6

N O

(all positions)

CH3

axial equatorial

6.114

SECTION 6

TABLE 6.65 Spin–Spin Coupling (Hyperfine Splitting Constants) (continued)

IONIZATION POTENTIALS The ionization potential is the energy required to remove an electron from an element or compound. Table 6.66A presents the ionization potentials for molecular species. The values are given in electron volts (eV). The values in parentheses are uncertainties in the final figure(s). Smaller numbers indicate lower energies or greater ease of electron removal. Table 6.66B is arranged alphabetically by element. Within an element, the compounds are arranged by increasing molecular weight.

TABLE 6.66A Ionization Potentials of Molecular Species 1 eV  23.061 kcal·mol1 Values in parentheses are uncertainties in the final figure(s).

Species

Ionization potential, eV

Diborane(6) Pentaborane(9) Hexaborane(10) Trimethylborane Triethylborane Methane CD4 Acetylene C2D2 Ethylene Ethane Propyne Allene Cyclopropene Cyclopropane Propane 1,2-Butadiene 1,3-Butadiene 1-Butyne 2-Butyne 1-Butene

12.0 10.5 9.3(1) 8.8(2) 9.0(2) 12.6 12.888 11.4 11.416(6) 10.5 11.5 10.36 10.16(2) 9.95 10.09(2) 11.1 9.57(2) 9.07 10.18(1) 9.9(1) 9.6

Species 2-Methyl-1-propene Cyclobutane Butane Isobutane Cyclopentadiene 1,2-Pentadiene 1,3-Pentadiene 1,4-Pentadiene 2,3-Pentadiene 2-Methyl-1,4-butadiene Cyclopentene 1-Pentene cis-2-Pentene trans-2-Pentene 2-Methyl-1-butene 3-Methyl-1-butane 3-Methyl-2-butene Cyclopentane Pentane Isopentane Neopentane

Ionization potential, eV 9.23(2) 10.58 10.63(3) 10.57 8.97 9.42 8.68 9.58 8.68 8.845(5) 9.01(1) 9.50(2) 9.11 9.06 9.12(2) 9.51(3) 8.69(2) 10.53(5) 10.35 10.32 10.35

6.115

SPECTROSCOPY

TABLE 6.66A Ionization Potentials of Molecular Species (continued )

Species cis-2-Butene trans-2-Butene 1,3-Hexadiyne 1,4-Hexadiyne 1,5-Hexadiyne 2,4-Hexadiyne 1-Methylcyclopentadiene 2-Methylcyclopentadiene Cyclohexene 1-Hexene 2,3-Dimethyl-2-butene Cyclohexane Hexane 2-Methylpentane 3-Ethylbutane 2,2-Dimethylbutane 2,3-Dimethylbutane Toluene Cycloheptatriene Bicyclo[2.2.1]heptane Bicyclo[3.2.0]heptane 1,2-Dimethylcyclopentadiene 5,5-Dimethylcyclopentadiene 1,3-Cycloheptadiene Norbornene 4-Methylcyclohexene Methylcyclohexane Heptane Phenylacetylene Styrene Cyclooctatetraene Cubane Ethylbenzene o-Xylene m-Xylene p-Xylene 7-Methylcycloheptatriene 1-Methylspiroheptadiene 6-Methylspiroheptadiene 1,2,3-Trimethylcyclopentadiene 1,5,5-Trimethylcyclopentadiene 4-Vinylcyclohexene cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane

Ionization potential, eV 9.13 9.13 9.25 9.75 10.35 9.75 8.43(5) 8.46(5) 8.72 9.45(2) 8.30 9.8 10.18 10.12 10.08 10.06 10.02 8.82(1) 8.5 8.67 9.37 8.1(1) 8.22(5) 8.55 8.95(15) 8.91(1) 9.85(3) 9.90(5) 8.815(5) 8.47(2) 8.0 8.74(15) 8.76(1) 8.56 8.58 8.44 8.39(10) 8.02(10) 8.4(1) 7.96(5) 8.0(1) 8.93(2) 10.08(2) 10.08(3)

Species Benzene Hexa-1,3-diene-5-yne 2,2,4-Trimethylpentane 2,2,3,3-Tetramethylbutane Indene -Methylstyrene Propylbenzene Isopropylbenzene 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Naphthalene Azulene Butylbenzene sec-Butylbenzene tert-Butylbenzene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene cis-Decalin trans-Decalin 1-Methylnaphthalene 2-Methylnaphthalene Pentamethylbenzene Hexamethylcyclopentadiene Biphenyl Hexamethylbenzene Fluorene Diphenylacetylene Anthracene Phenanthrene 1,2-Benzanthracene 1-Phenyldodecane 3-Phenyldodecane 7-Phenyltridecane 1-Phenylicosane 2-Phenylicosane 3-Phenylicosane 4-Phenylicosane 5-Phenylicosane 7-Phenylicosane 9-Phenylicosane N2 NH3 N2H2 N2H4 HCN C2N2

Ionization potential, eV 9.24 9.50 9.86 9.79 8.81 8.35(1) 8.72(1) 8.69(1) 8.48 8.27 8.4 8.12 7.42 8.69(1) 8.68(1) 8.68(1) 8.47(5) 8.03 9.61(2) 9.61(2) 7.96(1) 7.955(10) 7.92(2) 7.74(5) 8.27(1) 7.85(2) 8.63 8.85(5) 7.55 8.1 8.01 9.05(10) 8.95(10) 8.91(10) 9.34(10) 9.22(10) 8.95(10) 9.01(10) 9.04(10) 8.97(10) 9.06(10) 15.576 10.2 9.85(10) 8.74(6) 13.8 13.6

6.116

SECTION 6

TABLE 6.66A Ionization Potentials of Molecular Species (continued )

Species Methylamine Acetonitrile Ethyleneimine Ethylamine Dimethylamine Acrylonitrile Propionitrile Propylamine Isopropylamine Trimethylamine 3-Butenonitrile Pyrrole Butyronitrile Pyrrolidine Butylamine sec-Butylamine Isobutylamine tert-Butylamine Diethylamine Pyridine Aniline 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine Cyclohexylamine Dipropylamine Diisopropylamine Triethylamine Benzonitrile N-Methylaniline m-Toluidine 2,3-Dimethylpyridine 2,4-Dimethylpyridine 2,6-Dimethylpyridine Phenylacetonitrile 3-Methylbenzonitrile 4-Methylbenzonitrile N-Ethylcyclohexylamine N,N-Dimethylcyclohexylamine Dibutylamine N-Propylaniline N-Ethyl-N-methylaniline N,N-Dimethyl-o-toluidine N,N-Dimethyl-m-toluidine Propionaldehyde

Ionization potential, eV 8.97 12.2 9.94(15) 8.86(2) 8.24(2) 10.91(1) 11.84(2) 8.78(2) 8.72(3) 7.82(2) 10.39(1) 8.20(1) 11.67(5) 8.41 8.71(3) 8.70 8.70 8.64 8.01(1) 9.3 7.7 9.02(3) 9.04(3) 9.04(3) 8.86 7.84(2) 7.73(3) 7.50(2) 9.705(10) 7.32 7.50(2) 8.85(2) 8.85(3) 8.85(2) 9.4(5) 9.66(5) 9.76 7.56 7.12 7.69(3) 7.54 7.37 7.37 7.35 9.98

Species N,N-Dimethyl-p-toluidine Tripropylamine N-Butylaniline N,N-Diethylaniline N,N-Dimethyl-4-ethylaniline N,N-2,4-Tetramethylaniline N,N-2,6-Tetramethylaniline N,N-3,5-Tetramethylaniline N,N-Diethyl-4-toluidine N,N-Dimethyl-4isopropylaniline Diphenylamine N,N-Dipropylaniline N,N-Dimethyl-4-tertbutylaniline N,N-Dibutylaniline Triphenylamine Diazirine Diazomethane Methylhydrazine 1,1-Dimethylhydrazine 1,2-Dimethylhydrazine o-Diazine m-Diazine p-Diazine 1,1-Diethylhydrazine 1-Butyl-1-methylhydrazine p-Bis(dimethylamino)benzene Methyl azide O2 O3 Water (and D2O) H2O2 CO CO2 NO N2O NO2 Formaldehyde Methanol Acetaldehyde Ethylene oxide Ethanol Dimethyl ether Propenal Diphenyl ether

Ionization potential, eV 7.33 7.23 7.53 6.99 7.38 7.17 7.22 7.25 6.93 7.41 7.25(3) 6.96 7.43 6.95 6.86(3) 10.18(5) 8.999(1) 8.00(6) 7.67(5) 7.75(10) 9.9 9.9 9.8 7.59(5) 7.62(5) 6.9 9.5(1) 12.063(1) 12.3(1) 12.6 11.0 14.013(4) 13.769(30) 9.25 12.894 9.79 10.88 10.84 10.2 10.6 10.49 9.98 10.10(1) 8.82(5)

6.117

SPECTROSCOPY

TABLE 6.66A Ionization Potentials of Molecular Species (continued)

Species Acetone Allyl alcohol Methyl vinyl ether Propylene oxide Trimethylene oxide 1-Propanol 2-Propanol Furan 2-Butenal Butyraldehyde 2-Methylpropionaldehyde 2-Butanone Tetrahydrofuran 1-Butanol Diethyl ether Cyclopentanone Dihydropyran Pentanal 3-Methylbutyraldehyde 2-Pentanone 3-Methyl-2-butanone 3-Pentanone Cyclopentanone Phenol 4-Methyl-3-penten-2-one Cyclohexanone 2-Hexanone 4-Methyl-2-pentanone 3,3-Dimethyl-2-butanone Dipropyl ether Diisopropyl ether Benzaldehyde Tropone Benzyl alcohol Methoxybenzene m-Cresol 2-Heptanone Acetophenone 4-Methylbenzaldehyde Benzyl methyl ether Ethyl phenyl ether 3-Methylanisole Propiophenone 3-Methylacetophenone Phenyl benzoate Benzil Methyl methoxyacetate Methyl p-methoxybenzoate

Ionization potential, eV 9.69 9.67(5) 8.93(2) 10.22(2) 9.667(5) 10.1 10.15 8.89 9.73(1) 9.86(2) 9.74(3) 9.5 9.42 10.04 9.6 9.26(1) 8.34(1) 9.82(5) 9.71(5) 9.37(2) 9.30(2) 9.32(1) 9.25(1) 8.51 9.08(3) 9.14(1) 9.35 9.30 9.17(3) 9.27(5) 9.20(5) 9.52 9.68(2) 9.14(5) 8.21(2) 8.52(5) 9.33(3) 9.27(3) 9.33(5) 8.85(3) 8.13(2) 8.31(5) 9.27(5) 9.15(5) 8.98(5) 8.78(5) 9.56(5) 8.43(4)

Species Benzophenone 4-Methylbenzophenone Formic acid Acetic acid Methyl formate Propionic acid Ethyl formate Methyl acetate Dimethoxymethane Vinyl acetate 2,3-Butanedione Butanoic acid Isobutyric acid Propyl formate Ethyl acetate Methyl propionate 1,4-Dioxane 1,1-Dimethoxyethane 2-Furaldehyde 2,4-Pentanedione Butyl formate Isobutyl formate Propyl acetate Isopropyl acetate Ethyl propionate Methyl butyrate Methyl isobutyrate Diethoxymethane 1,4-Quinone Butyl acetate Isobutyl acetate sec-Butyl acetate Benzoic acid p-Hydroxybenzaldehyde -Hydroxyacetophenone Methyl benzoate p-Methoxybenzaldehyde m-Hydroxyacetophenone p-Hydroxyacetophenone -Methoxyacetophenone m-Methoxyacetophenone p-Methoxyacetophenone Methyl p-methylbenzoate p-Hydroxybenzophenone N2F4 OF2 XeF2 Fluoromethane

Ionization potential, eV 9.4 9.13(5) 11.05(1) 10.69(3) 10.815(5) 10.24(1) 10.61(1) 10.27(2) 10.00(5) 9.19(5) 9.24(3) 10.16(5) 10.02(5) 10.54(1) 10.11(2) 10.15(3) 9.13(3) 9.65(3) 9.21(1) 8.87(3) 10.50(2) 10.46(2) 10.04(3) 9.99(1) 10.00(2) 10.07(3) 9.98(2) 9.70(5) 9.67(2) 9.56(3) 9.97 9.91(3) 9.73(9) 9.32(2) 9.33(5) 9.35(6) 8.60(3) 8.67(5) 8.70(3) 8.60(5) 8.53(5) 8.62(5) 8.94(4) 8.59(5) 12.04(10) 13.6 11.5(2) 12.85(1)

6.118

SECTION 6

TABLE 6.66A Ionization Potentials of Molecular Species (continued)

Species Diphenyl carbonate Acetamide N,N-Dimethylformamide N-Methylacetamide NN-Dimethylacetamide N,N-Diethylformamide 2-Pyridinecarboxaldehyde 4-Pyridinecarboxaldehyde N,N-Diethylacetamide Phenyl isocyanate Benzamide p-Aminobenzaldehyde p-Methoxyaniline Acetanilide m-Aminoacetophenone p-Aminoacetophenone -Cyanoacetophenone Nitromethane Nitroethane 1-Nitropropane 2-Nitropropane Nitrobenzene m-Nitrotoluene p-Nitrotoluene o-Nitroaniline m-Nitroaniline p-Nitroaniline Ethyl nitrate Propyl nitrate p-Nitrophenol p-Nitrobenzaldehyde m-Nitroacetophenone p-Nitroacetophenone Methyl p-nitrobenzoate F2 HF BF3 C2F4 Hexafluorobenzene trans-N2F2 NF3 Methyl isothiocyanate Methyl thiocyanate Ethyl isothiocyanate Ethyl thiocyanate Phenyl isothiocyanate Tolyl thiocyanate Thiourea

Ionization potential, eV 9.01(5) 9.77(2) 9.12(2) 8.90(2) 8.81(3) 8.89(2) 9.75(5) 10.12(5) 8.60(2) 8.77(2) 9.4(2) 8.25(2) 7.82 8.39(10) 8.09(5) 8.17(2) 9.56(5) 11.1 10.88(5) 10.81(3) 10.71(5) 9.92 9.65(5) 9.87 8.66 8.7 8.85 11.22 11.07(2) 9.52 10.27(1) 9.89(5) 10.07(2) 10.20(3) 15.7 15.77(2) 15.5 10.12 9.97 13.1(1) 13.2(2) 9.25(3) 10.065(10) 9.14(3) 9.89(1) 8.520(5) 9.06(5) 8.50(5)

Species Fluoroethylene Fluorobenzene 1,2-Difluorobenzene 1,4-Difluorobenzene Trifluoroethylene 3,3,3-Trifluoro-1-propene o-Fluorophenol PH3 PF3 Methylphosphine Ethylphosphine Trimethylphosphine Triphenylphosphine S6 S7 Hydrogen sulfide Carbon disulfide Sulfur dioxide Methanethiol Ethylene sulfide Ethanethiol Dimethyl sulfide Propylene sulfide 1-Propanethiol Ethyl methyl sulfide Thiophene Methyl 1-propenyl sulfide 1-Butanethiol Diethyl sulfide Methyl propyl sulfide Isopropyl methyl sulfide Thiophenol 2-Ethylthiophene Dipropyl sulfide Methyl phenyl sulfide 2-Propylthiophene 2-Butylthiophene Dimethyl disulfide Diethyl disulfide COS SO2F2 p-Dichlorobenzene Chloroform Trichloroethylene 1,1,2,2-Tetrachloroethane CNCl CF3Cl Chlorotrifluoroethylene

Ionization potential, eV 10.37 9.2 9.31 9.15 10.14 10.9 8.66(1) 9.98 9.71 9.72(15) 9.47(50) 8.6(2) 7.36(5) 9.7 9.2(3) 10.4 10.080 12.34(2) 9.440(5) 8.87(15) 9.285(5) 8.685(5) 8.6(2) 9.195 8.55(1) 8.860(5) 8.7(2) 9.14(2) 8.430(5) 8.80(15) 8.7(2) 8.32(1) 8.8(2) 8.5 8.9 8.6(2) 8.5(2) 8.46(3) 8.27(3) 11.17(1) 13.3(1) 8.95 11.42(3) 9.45 11.10(5) 12.49(4) 12.91(3) 10.4(2)

6.119

SPECTROSCOPY

TABLE 6.66A Ionization Potentials of Molecular Species (continued)

Species 1-Methylthiourea 1-Vinylthiourea 1,1-Dimethylthiourea 1,3-Dimethylthiourea 1,1,3-Trimethylthiourea Tetramethylthiourea CH3COSH Cl2 HCl CCl4 Tetrachloroethylene PCl3 Chloromethane Chloroethane Chloroethylene 1-Chloro-1-propyne 1-Chloropropane 2-Chloropropane 1-Chlorobutane 2-Chlorobutane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane Chlorobenzene -Chlorotoluene o-Chlorotoluene m-Chlorotoluene p-Chlorotoluene endo-5-Chloro-2-norbornene exo-5-Chloro-2-norbornene Dichloromethane cis-1,2-Dichloroethylene trans-1,2-Dichloroethylene 1,2-Dichloroethane 2,3-Dichloro-1-propene 1,2-Dichloropropane 1,3-Dichloropropane o-Dichlorobenzene m-Dichlorobenzene HI ICI IBr Iodomethane Iodoethane 1-Iodopropane 2-Iodopropane 1-Iodobutane 2-Iodobutane 1-Iodo-2-methylpropane

Ionization potential, eV 8.29(5) 8.29(5) 8.34(5) 8.17(5) 7.93(5) 7.95(5) 10.00(2) 11.48(1) 12.74 11.47(1) 9.32(1) 9.91 11.3 10.97 9.996 9.9(1) 10.82(3) 10.78(2) 10.67(3) 10.65(3) 10.66(3) 10.61(3) 9.07 9.19(5) 8.83(2) 8.83(2) 8.69(2) 9.10(15) 9.15(15) 11.35(2) 9.65 9.64 11.12(5) 9.82(3) 10.87(5) 10.85(5) 9.06 9.12(1) 10.39 10.31(2) 9.98(3) 9.54 9.33 9.26(1) 9.17(2) 9.21(1) 9.09(2) 9.18(2)

Species Chloropentafluorobenzene Dichlorodifluoromethane CF3CCl ¨ CClCF3 Trichlorofluoromethane CF3CCl3 CFCl2CF2Cl ClO3F 1-Bromo-1-propene 1-Bromopropane 2-Bromopropane 1-Bromobutane 2-Bromobutane 1-Bromo-2-methylpropane 2-Bromo-2-methylpropane 1-Bromopentane Bromobenzene o-Bromotoluene m-Bromotoluene p-Bromotoluene Dibromomethane cis-1,2-Dibromoethylene trans-1,2-Dibromoethylene 1,1-Dibromoethane 1,3-Dibromopropane Bromoform Tribromoethylene Cyanogen bromide Bromotrifluoromethane 2-Bromopyridine 4-Bromopyridine Acetyl bromide Methyl bromoacetate CF2BrCH2Br Bromochloromethane 1-Bromo-2-chloroethane Bromodichloromethane Bromotrimethylsilane I2 CF3CF2CF2CH2Cl Dichlorofluoromethane Chlorotrimethylsilane Trichloromethylsilane Trichlorovinylsilane Trichloroethylsilane Trichloroisopropylsilane C2H5V(CO)4 Cr(CO)6 C2H5Mn(CO)3

Ionization potential, eV 10.4(1) 12.31(5) 10.36(1) 11.77(2) 11.78(3) 11.99(2) 13.6(2) 9.30(5) 10.18(1) 10.075(10) 10.125(10) 9.98(1) 10.09(2) 9.89(3) 10.10(2) 8.98(2) 8.78(1) 8.81(2) 8.67(2) 10.49(2) 9.45 9.46 10.19(3) 10.07(2) 10.51(2) 9.27 11.95(8) 11.89 9.65(5) 9.94(5) 10.55(5) 10.37(5) 10.83(1) 10.77(1) 10.63(3) 10.88(5) 10.24(2) 9.28(2) 11.84(2) 12.39(20) 10.58(4) 11.36(3) 10.79(2) 10.74(4) 10.28(10) 8.2(3) 8.03(3) 8.3(4)

6.120

SECTION 6

TABLE 6.66A Ionization Potentials of Molecular Species

Species

Ionization potential, eV

2-Iodo-2-methylpropane 1-Iodopentane Iodobenzene o-Iodotoluene m-Iodotoluene p-Iodotoluene RuO4 2-Chloropyridine 4-Chloropyridine Acetyl chloride 1-Chloro-2-propanone 2-Chlorophenol 4-Chlorophenol Benzoyl chloride 4-Chlorobenzaldehyde -Chloroacetophenone p-Chloroacetophenone Methyl chloroacetate 4-Methoxybenzoyl chloride 4-Chlorobenzoyl chloride cis-Chlorofluoroethylene trans-Chlorofluoroethylene o-Chlorofluorobenzene m-Chlorofluorobenzene p-Chlorofluorobenzene Chlorodifluoromethane 1-Chloro-1,1-difluoroethane

9.02(2) 9.19(1) 8.73 8.62(1) 8.61(3) 8.50(1) 12.33(23) 9.91(5) 10.15(5) 11.02(5) 9.99 9.28 9.07 9.70(1) 9.61(1) 9.5 9.47(5) 10.53(5) 8.87(5) 9.58(3) 9.86 9.87 9.155(10) 9.21(1) 9.43(2) 12.45(5) 11.98(1)

Species Fe(CO)5 Ni(CO)4 Mo(CO)6 W(CO)6 As4 Arsine AsCl3 Trimethylarsine Triphenylarsine Br2 HBr BrCl Bromomethane Bromoethylene Bromoethane 1-Bromo-1-propyne OsO4 Dimethylmercury Diethylmercury Diisopropylmercury CH3HgCl Triphenylbismuth Stibine Triphenylstibine Tetramethylstannane Tetramethylplumbane Tetramethylgermane

Ionization potential, eV 7.95(3) 8.28(3) 8.12(3) 8.18(3) 9.07(7) 10.03 11.7(1) 8.3(1) 7.34(7) 10.54(3) 11.62(3) 11.1(2) 10.53 9.80 10.29 10.1(1) 12.97(12) 9.0 8.5(1) 7.6(1) 11.5(2) 7.3(1) 9.58 7.3(1) 8.25(15) 8.0(4) 9.2(2)

TABLE 6.66B Alphabetical Listing of Ionization Potentials of Molecular Species Species

IP (eV)

Acetylene Acetylene-d2; C2D2 Allene Ammonia (NH3) Anthracene Azine (N2H2) Azulene 1,2-Benzanthracene Benzene Bicyclo[2.2.1]heptane Bicyclo[3.2.0]heptane Biphenyl 1,2-Butadiene 1,3-Butadiene

11.4 11.416 10.16 10.2 7.55 9.85(10) 7.42 8.01 9.24 8.67 9.37 8.27(1) 9.57(2) 9.07

Species Butane 1-Butene cis-2-Butene trans-2-Butene 1-Butyne 2-Butyne Butylbenzene sec-Butylbenzene tert-Butylbenzene Carbon dioxide, CO2 Cubane Cyclobutane 1,3-Cycloheptadiene Cycloheptatriene

IP (eV) 10.63(3) 9.6 9.13 9.13 10.18(1) 9.9(1) 8.69(1) 8.68(1) 8.68(1) 12.888 8.74(15) 10.58 8.55 8.5

6.121

SPECTROSCOPY

TABLE 6.66B Alphabetical Listing of Ionization Potentials of Molecular Species (continued) Species

IP (eV)

Species

IP (eV)

Cyclohexane Cyclohexene Cyclooctatetraene Cyclopentadiene Cyclopentane Cyclopentene Cyclopropane Cyclopropene cis-Decalin trans-Decalin Diazomethane (C2N2) Diborane 2,2-Dimethylbutane 2,3-Dimethylbutane 2,3-Dimethyl-2-butene cis-1,2-Dimethylcyclohexane trans-1,2-Dimethylcyclohexane 1,2-Dimethylcyclopentadiene 5,5-Dimethylcyclopentadiene Diphenylacetylene Ethane Ethylbenzene 3-Ethylbutane Ethylene Fluorene Heptane Hexaborane Hexa-1,3-diene-5-yne 1,3-Hexadiyne 1,4-Hexadiyne 1,5-Hexadiyne 2,4-Hexadiyne Hexamethylbenzene Hexamethylcyclopentadiene Hexane 1-Hexene Hydrazine (N2H4) Hydrocyanic acid (HCN) Indene Isobutane Isopentane Isopropylbenzene Methane 2-Methyl-1,4-butadiene 3-Methyl-1-butane 2-Methyl-1-butene 3-Methyl-2-butene 7-Methylcycloheptatriene Methylcyclohexane

9.8 8.72 8 8.97 10.53(5) 9.01(1) 10.09 9.95 9.61(2) 9.61(2) 13.6 12 10.06 10.02 8.3 10.08(2) 10.08(3) 8.1(1) 8.22(5) 8.85(5) 11.5 8.76(1) 10.08 10.5 8.63 9.90(5) 9.3 9.5 9.25 9.75 10.35 9.75 7.85(2) 7.74(5) 10.18 9.45(2) 8.74(6) 13.8 8.81 10.57 10.32 8.69(1) 12.6 8.845(5) 9.51(3) 9.12(2) 8.69(2) 8.39(10) 9.85(3)

4-Methylcyclohexene 1-Methylcyclopentadiene 2-Methylcyclopentadiene 1-Methylnaphthalene 2-Methylnaphthalene 2-Methylpentane 2-Methyl-l-propene 1-Methylspiroheptadiene 6-Methylspiroheptadiene -Methylstyrene Naphthalene Neopentane Nitrogen (N2) Norbornene Pentaborane(9) 1,2-Pentadiene 1,3-Pentadiene 1,4-Pentadiene 2,3-Pentadiene Pentamethylbenzene Pentane 1-Pentene cis-2-Pentene trans-2-Pentene Phenanthrene Phenylacetylene 1-Phenyldodecane 3-Phenyldodecane 1-Phenylicosane 2-Phenylicosane 3-Phenylicosane 4-Phenylicosane 5-Phenylicosane 7-Phenylicosane 9-Phenylicosane 7-Phenyltridecane Propane Propylbenzene Propyne Styrene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene 2,2,3,3-Tetramethylbutane Toluene Triethylborane 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Trimethylborane

8.91(1) 8.43(5) 8.46(5) 7.96(1) 7.955(10) 10.12 9.23(2) 8.02(10) 8.4(1) 8.35(1) 8.12 10.35 15.576 8.95(15) 10.5 9.42 8.68 9.58 8.68 7.92(2) 10.35 9.50(2) 9.11 9.06 8.1 8.815(5) 9.05(10) 8.95(10) 9.34(10) 9.22(10) 8.95(10) 9.01(10) 9.04(10) 8.97(10) 9.06(10) 8.9100) 11.1 8.72(1) 10.36 8.47(2) 8.47(5) 8.03 9.79 8.82(1) 9 8.48 8.27 8.4 8.8

6.122

SECTION 6

TABLE 6.66B Alphabetical Listing of Ionization Potentials of Molecular Species (continued) Species

IP (eV)

1,2,3-Trimethylcyclopentadiene 1,5,5-Trimethylcyclopentadiene 2,2,4-Trimethylpentane 4-Vinylcyclohexene

7.96(5) 8.0(1) 9.86 8.93(2)

Species

IP (eV)

m-Xylene o-Xylene p-Xylene

8.58 8.56 8.44

TABLE 6.67 Ionization potentials of radical species 1 eV  23.061 kcal·mol1 Values in parentheses are uncertainties in the final figure(s).

Species

Ionization potential, eV

BH BH2 BF C2 C3 CH CH2 CH3 CD3 C2H3 C2H5 HC˜CCH2 Allyl Cyclopropyl C3H6 Propyl Isopropyl C4H2 C4H4 Cyclobutyl CH3CH ¨ CHCH2 CH2 ¨ C(CH3)CH2 Butyl sec-Butyl Isobutyl tert-Butyl Cyclopentyl

9.77(5) 11.4(2) 11.3 12.0(6) 12.6 11.1(2) 10.396(3) 9.83 9.832(2) 9.4 8.4 8.25 8.15 8.05 9.73 8.1 7.5 10.2(1) 9.87 7.88(5) 7.71(5) 8.03(5) 8.64(5) 7.93(5) 8.35(5) 7.42(7) 7.79(2)

Species tert-Pentyl Neopentyl Benzyne Cyclohexyl Benzyl Cycloheptatrienyl 1-Methylnaphthyl 2-Methylnaphthyl (CH3)2CCN m-Nitrobenzyl OH HO2 CHO CH3CO C6H5O CF2 NF2 CH2F CHF2 HS CH3S C6H5S CCl3 CH2Cl CHCl2 NH2

Ionization potential, eV 7.1(1) 8.3(1) 9.6 7.7 7.76(8) 6.24(1) 7.35 7.56(5) 9.15(10) 8.56(10) 13.17(10) 11.53(2) 9.8 10.3 8.84 11.8 11.9 9.35 9.45 10.5(1) 8.06(10) 8.63(10) 8.78(5) 9.32 9.30 11.3

X-RAY DIFFRACTION The X-ray diffraction method utilizes a monochromatic beam of X-rays to which a solid material is exposed. The beam of radiation interacts with the solid, and is both reflected and diffracted. The reflection pattern is recorded by a detector system sensitive to the X-radiation. Until recently, this involved an intricate mechanical device whose complex

SPECTROSCOPY

6.123

motion permitted X-rays to be recorded over a range of positions, as the detector position changed. Automated instruments using this technology are often referred to as “4-circle diffractometers,” a term that refers to this complex detector motion. Newer X-ray instruments use charge coupled devices (CCDs) to simultaneously detect X-ray diffraction position and intensity over a much broader area. This enhanced detection technology reduces, often dramatically, the time required for data acquisition. The Bragg equation describes the relationship between the impinging X-radiation, the diffraction angle, and the separation between lattice planes in the crystal under study. The Bragg equation is generally written as  sin1 (/2d) where is the angle of the diffracted beam (usually called a reflection),  is the wavelength of the incident X-ray beam, and d is the inter-planar spacing. From the diffraction pattern, both position and intensity, one can obtain structural information about the crystal under study. Two types of X-ray studies are commonplace: X-ray powder analysis and crystal structure determination. Even in powders, the regular arrangement of atoms within the solid leads to characteristic diffraction patterns. X-ray powder patterns may therefore be used to characterize solids in much the same way that a UV or IR spectrum will give useful information but not necessarily a definitive structure. The X-ray powder pattern obtained for the sodium salt of 2-propylpentanoic acid – (CH3CH2CH2)2CHCOO Na is shown in Figure 6.2. The X-ray powder pattern was detected over a range 2 , in this case 2–40 from the incident beam. This is a typical range although other ranges are used as well. The peak intensities are expressed in counts per second (cps) and may vary from experiment to experiment. However, the ratios of the peak heights are characteristic. Thus, X-ray powder patterns obtained from different samples of the same compound should give very similar, if not identical, patterns. Because the X-ray powder patterns are complex, the identity of two spectra suggests that the compounds producing them are also identical.

27500 25000 22500 20000

CPS

17500 15000 12500 10000 7500 5000 2500 0 2

4

6

8

10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40 –2

FIGURE 6.2

X-ray powder pattern of 2-propylpentanoic acid, (CH3CH2CH2)2CHCOONa.

6.124

SECTION 6

The determination of a molecular structure from X-ray diffraction data is of critical importance to modern chemical and biological sciences. For small molecules, the structure is normally determined by direct methods. The X-ray diffraction pattern resulting from the interaction of X-rays with the electron clouds of different elements gives a pattern from which the elements present and their connectivity may be deduced. The expected diffraction pattern calculated for an apparent structure is then compared with the observed data to refine the result. Refinement factors (usually expressed as Rw) of 1–3% are common in modern small molecule structure determinations. The Cambridge Structural Database is a repository for more than 250 000 (as of 2002) small molecule crystal structures. It is accessible at http:// www.ccdc.cam.ac.uk/ by subscription. The process is more complex for such large molecules as proteins. Typically, a model of the amino acid backbone will be constructed first to obtain a general sense of the overall structure. Amino acid sidechains will then be added and the experimental data are again compared with the calculated diffraction pattern. This process is repeated until the complete structure is obtained. Because the uncertainties are larger in these systems, the resolution of the structure is typically reported in Ångstroms. Structures that have a resolution of 3 Å can and do give important information, especially when the gross structure of a protein was previously unknown. Recent improvements in chemical and biological techniques, computers, and X-ray instrumentation (especially in detectors) have made resolutions in the 1–2 Å range more common. A database, called the Protein Data Bank or “PDB,” is a repository for protein structures. The database may be consulted at no charge and gives access to structures obtained by X-ray methods as well as by NMR and theoretical techniques. The Internet address is http://www.rcsb.org/pdb.

SECTION 7

PHYSICOCHEMICAL RELATIONSHIPS

LINEAR FREE ENERGY RELATIONSHIPS . . . . . . . . . Table 7-1 Hammett and Taft Substituent Constants . . . . Table 7-2 pKA and Rho Values for the Hammett Equation Table 7-3 pKA and Rho Values for the Taft Equation . . . Table 7-4 Special Hammett Sigma Constants . . . . . . .

7.1

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

. . . . .

7.2 7.3 7.8 7.10 7.10

7.2

SECTION 7

LINEAR FREE ENERGY RELATIONSHIPS Organic chemists have studied the influence of substituents on various reactions for the better part of a century. Linear free energy relationships have played an important role in this pursuit by correlating equilibrium and rate processes. One of the earliest examples is now known as the Hammett equation. It emerged from the observation that the acidities of benzoic acids correlated with the rates at which ethyl esters of benzoic acids hydrolyzed. The relationship was expressed as follows in which K represents an equilibrium constant and k is a rate constant. The proportionality constant, m, is the slope of the log–log data plot for the two processes. m log

k K  log K0 k0

When H and S vary linearly for two processes or when H or S is constant, the free energy relationship will be linear. The common form of the relationship is either log

k K   or log    K0 k0

for equilibrium or rate processes, respectively. The Greek letters rho () and sigma () symbolize the reaction and substituent constants, respectively. These equations may be used to describe and understand the influence of substituents on a reaction. Separate sigma values are defined by this reaction for meta and para substituents and provide a measure of the total electronic influence (polar, inductive, and resonance effects) in the absence of conjugation effects. The correlation is not as useful for ortho-substituted aromatic compounds because steric or other proximity effects intercede. Typically in aromatic systems, the inductive effect is transmitted about equally to the meta and para positions. Consequently, m is an approximate measure of a substituent’s inductive effect whereas p gives an approximate measure of a substituent’s resonance effect. Consider the dissociation of benzoic acids in water. This process is assigned a reaction constant  of 1. The reaction is illustrated using “Sub” to represent a substituent. Sub

O C OH

H2O

O H+ +

Sub

C O–

We may compare three para-substituted benzoic acids. The reference point is parahydrogen, which has a p constant of 0, by definition. The methoxy group is electron donating and has a p constant of 0.27. Adding electrons to the benzoate anion (structure at right, above) should make the anion less stable. Thus, the ability to dissociate a cation (the acidity) should be diminished. The pKA is log KA so the higher the pKA, the lower the acidity (the weaker the acid). In contrast, the nitro group is electron withdrawing. Its p constant is 0.78 and its presence in the benzoate anion should be stabilizing. A more stable conjugate base implies a stronger acid and, indeed, the pKA for 4-nitrobenzoic acid is 3.44. Because these values are logarithmic, there is an order of magnitude difference in the acidities as a result of these substituents.

7.3

PHYSICOCHEMICAL RELATIONSHIPS

Comparison of acidities and sigma constants for three benzoic acids COOH

COOH

COOH

Compound OCH3

Substituent p pKA

H

NO2

H 0.00 4.20

OCH3 0.27 4.49

NO2 0.78 3.44

Values of Hammett sigma constants are listed in Table 7.1. Taft sigma* (*) values may be used similarly with respect to aliphatic and alicyclic systems. Values of * constants are also listed in Table 7.1. The reaction constant  is related to the reaction process rather than to the substituents present. A somewhat oversimplified way of considering  is to say that it indicates the demand the process makes on the substituents. The acidity of a benzoic acid, C6H5COOH, derivative is affected directly by substituents in the aromatic ring. Substituents exert somewhat less influence in phenylacetic acids, C6H5CH2COOH, because the methylene group between carboxylate and the aromatic ring tends to insulate the latter from the former. This “insulation” is even greater for phenyipropanoic acids, C6H5CH2CH2COOH. The reaction constant  for dissociation of benzoic acid in water is set at 1.0. The reaction constants for dissociation of phenylacetic and phenylpropanoic acids are 0.49 and 0.21, respectively, under the same conditions. Values of the reaction parameter for some aromatic and aliphatic systems are given in Tables 7.2 and 7.3. Since substituent effects in aliphatic systems and in meta positions in aromatic systems are essentially inductive in character, * and m values are related by the expression m  0.217*  0.106. Substituent effects fall off with increasing distance from the reaction center. The decline is generally a factor of 0.36 for the interposition of a ˆ CH2 ˆ group. This enables * values to be estimated for R ˆ CH2 ˆ groups not otherwise available. Modified sigma constants have been formulated for situations in which the substituent enters into resonance with the reaction center in an electron-demanding transition state () or for an electron-rich transition state (). Generally,  constants give better correlations in reactions involving phenols, anilines, pyridines, and in nucleophilic substitutions. Values for some modified sigma constants are given in Table 7.4.

TABLE 7.1 Hammett and Taft Substituent Constants Hammett constants Substituent ˆ AsO3H ˆ B(OH)2 ˆ Br ˆ CH2Br m- BrC6H4 ˆ

m

p

0.09 0.01 0.39

0.02 0.45 0.23 0.09

Taft constant * 0.06 2.84 1.00

7.4

SECTION 7

TABLE 7.1 Hammett and Taft Substituent Constants (continued ) Hammett constants Substituent p-BrC6H4 ˆ ˆ CH3 ˆ CH2CH3 ˆ CH2CH2CH3 ˆ CH(CH3)2 (isopropyl) ˆ CH2CH2CH2CH3 ˆ CH2CH(CH3)2 (isobutyl) ˆ CH(CH3)CH2CH3 (sec-butyl) ˆ C(CH3)3 (t-butyl) ˆ CH2CH2CH2CH2CH3 (n-pentyl) ˆ CH2CH2CH(CH3)2 (isopentyl) ˆ CH2C(CH3)3 (t-amyl) ˆ CH2CH2CH2CH2CH2CH2CH3 ˆ CH(CH2)2 (cyclopropyl) ˆ CH(CH2)5 (cyclohexyl)

m 0.07 0.07 0.05 0.07 0.07 0.07 0.10

p 0.08 0.17 0.15 0.15 0.15 0.16 0.12 0.12 0.20 0.23

0.07

0.21 0.26

Taft constant *

0.0 0.10 0.12 0.19 0.13 0.13 0.19 0.30 0.25 0.17 0.12 0.37 0.15

0.48

ˆ CH ¨ CH2 (vinyl, ethenyl) ˆ CH ¨ C(CH3)2 ˆ CH ¨ CHCH3, trans ˆ CH2CH ¨ CH2 ˆ CH ¨ CHC6H5 ˆ C ˜ CH ˆ C ˜ CC6H5 ˆ CH2C ˜ CH ˆ C6H5 (phenyl) p ˆ CH3C6H4 ( p-tolyl)

0.06 0.02

0.04

0.14 0.21 0.14

0.05 0.23 0.16

0.06

0.01 0.5

(1-naphthyl) (2-naphthyl) ˆ CH2C6H5 (benzyl) ˆ CH2CH2C6H5 (2-phenylethyl) ˆ CH(CH3)C6H5 (-phenylethyl) ˆ CH(C6H5)2 (benzhydryl) H2 C

O

(2-furoyl)

(3-indolyl)

0.56 0.19 0.36 0.0 0.41 2.18 1.35 0.81 0.60

0.75

0.46

0.75 0.22 0.06 0.37 0.41 0.44

0.25 0.06

7.5

PHYSICOCHEMICAL RELATIONSHIPS

TABLE 7.1 Hammett and Taft Substituent Constants (continued ) Hammett constants m

Substituent ( S S

p

y)

Taft constant * 1.31

(2-thienyl) CH2

0.31

(2-thienylmethylene)

ˆ CHO (formyl) ˆ COCH3 (acetyl) ˆ COCH2CH3 (propionyl) ˆ COCH(CH3)2 ˆ COC(CH3)3 ˆ COCF3 (trifluoroacetyl) ˆ COC6H5 (benzoyl) ˆ CONH2 ˆ CONHC6H5 ˆ CH2COCH3 (acetonyl) ˆ CH2CONH2 (acetamido) ˆ CH2CH2CONH2 ˆ CH2CH2CH2CONH2 ˆ CH2CONHC6H5 ˆ COO (carboxylate) ˆ COOH (carboxyl) ˆ CO ˆ OCH3 (carbomethoxy) ˆ CO ˆ OCH2CH3 (carbethoxy) ˆ CH2CO ˆ OCH3 ˆ CH2CO ˆ OCH2CH3 ˆ CH2COOH ˆ CH2CH2COOH ˆ Cl ˆ CCl3 (trichloromethyl) ˆ CHCl2 (dichloromethyl) ˆ CH2Cl (chloromethyl) ˆ CH2CH2Cl ˆ CH2CCl3 ˆ CH2CH2CCl3 ˆ CH ¨ CCl2 ˆ CH2CH ¨ CCl2 p-ClC6H4 ˆ (p-chlorophenyl) ˆF ˆ CF3 (trifluoromethyl) ˆ CHF2 (difluoromethyl) ˆ CH2F (fluoromethyl) ˆ CH2CF3 ˆ CH2CF2CF2CF3 ˆ C6F5 (pentafluorophenyl) ˆ Ge(CH3)3 (trimethylgermyl) ˆ Ge(CH2CH3)3 (triethylgermyl) ˆH ˆI ˆ CH2I (iodomethyl) ˆ N2 (diazonio)

0.36 0.38

0.22 0.50 0.48 0.47 0.32

0.65 0.34 0.28

0.46 0.36

0.1 0.36 0.32 0.37

0.0 0.43 0.39 0.45

0.03 0.37 0.47

0.07 0.23

0.12

0.18

0.34 0.43

0.08 0.06 0.54

0.12

0.00 0.35

0.03 0.0 0.0 0.00 0.28

1.76

1.91

1.65

3.7 2.2 1.68 1.56 0.60 0.31 0.19 0.12 0.0 1.06 2.08 2.00 2.12 1.06 0.82 0.06 2.96 2.65 1.94 1.05 0.38 0.75 0.25 1.00 0.19 3.21 2.61 2.05 1.10 0.90 0.87

0.49 2.46 0.85

7.6

SECTION 7

TABLE 7.1 Hammett and Taft Substituent Constants (continued ) Hammett constants Substituent

m

ˆ N3 (azido) ˆ NH2 (amino) ˆ NH3 ˆ CH2 ˆ NH2 (aminomethyl) ˆ CH2 ˆ NH3 ˆ NH ˆ CH3 (methylamino) ˆ NH ˆ C2H5 (ethylamino) ˆ NH ˆ C4H9 (butylamino) ˆ NH(CH3)2 ˆ NH2 ˆ CH3 ˆ NH2 ˆ C2H5 ˆ N(CH3)3 (trimethylammonium) ˆ N(CH3)2 (dimethylamino) ˆ CH2 ˆ N(CH3)3 ˆ N(CF3)2 [bis(trifluoromethyl)amino] p- H2N ˆ C6H5 ˆ ( p-aminophenyl) ˆ NH ˆ CO ˆ CH3 ˆ NH ˆ CO ˆ C2H5 ˆ NH ˆ CO ˆ C6H5 ˆ NH ˆ CHO ˆ NH ˆ CO ˆ NH2 ˆ NH ˆ OH (hydroxylamino) ˆ NH ˆ CO ˆ OC2H5 ˆ CH2 ˆ NH ˆ CO ˆ CH3 ˆ NH ˆ SO2 ˆ C6H5 ˆ NH ˆ NH2 (hydrazido) ˆ C ˜ N (cyano) ˆ CH2 ˆ CN (cyanomethyl) ˆ N ¨ O (nitroso) ˆ NO2 (nitro) ˆ CH2 ˆ NO2 (nitromethyl) ˆ CH2 ˆ CH2 ˆ NO2 (2-nitroethyl) ˆ CH ¨ CHNO2 (2-nitroethylenyl) m- O2N ˆ C6H4 ˆ (m-nitrophenyl) p- O2N ˆ C6H4 ˆ (p-nitrophenyl)

0.33 0.16 1.13

0.08 0.66 1.70

0.30 0.24 0.34

0.84 0.61 0.51

0.96 0.96 0.88 0.2 0.45 0.21 0.22 0.25 0.18 0.04 0.33 0.02 0.56 0.17 0.71

p

0.82 0.83 0.53 0.30 0.00 0.08

Taft constant * 2.62 0.62 3.76 0.50 2.24

4.36 3.74 3.74 4.55 0.32 1.90

1.40 1.56 1.68 1.62 1.31

0.34 1.99 0.43 1.99 0.55 0.66 0.01 0.12 0.78

0.33

0.26 0.18 0.24

0.43

0.41

3.30 1.30 4.0 1.40 0.50

NO2 O2N NO2 (picryl)

1.37 1.65

CO-CH3 N CO-C6H5

N

CO-CH3

ˆ O ˆ OH (hydroxy) ˆ O ˆ CH3 (methoxy) ˆ O ˆ C2H5 (ethoxy)

0.71 0.12 0.12 0.10

0.52 0.37 0.27 0.24

1.34 1.81 1.68

7.7

PHYSICOCHEMICAL RELATIONSHIPS

TABLE 7.1 Hammett and Taft Substituent Constants (continued ) Hammett constants Substituent



ˆ O ˆ C3H7 (propoxy) ˆ O ˆ CH(CH3)2 (isopropoxy) ˆ O ˆ C4H9 (butoxy) ˆ O ˆ C5H9 (cyclopentyloxy) ˆ O ˆ C6H11 (cyclohexyloxy) ˆ O ˆ CH2 ˆ C6H11 (cyclohexylmethoxy) ˆ O ˆ C6H5 (phenoxy) ˆ O ˆ CH2 ˆ C6H5 (phenylmethoxy) ˆ OCF3 (trifluoromethoxy)

0.00 0.05 0.05 0.29 0.18 0.25 0.40

p 0.25 0.45 0.32

0.32 0.42 0.35

Taft constant * 1.68 1.62 1.68 1.62 1.81 1.31 2.43

O O

0.27

(3,4- methylenedioxyphenyl, piperonyl)

O

(3,4-ethylenedioxyphenyl) O ˆ O ˆ CO ˆ CH3 (acetoxy) ˆ ONO2 (nitrate ester) ˆ O ˆ N ¨ C(CH3)2 ˆ ONH3 ˆ CH2 ˆ O ˆ CH2 ˆ OH ˆ CH2 ˆ O ˆ CH3 ˆ CH(OH) ˆ CH3 ˆ CH(OH) ˆ C6H5 p-HO ˆ C6H4 ˆ (p-hydroxyphenyl) p-CH3O ˆ C6H4 ˆ (p-methoxyphenyl) ˆ CH2 ˆ CH(OH) ˆ CH3 ˆ CH2 ˆ C(OH)(CH3)2 ˆ P(CH3)2 (dimethylphosphino) ˆ P(CH3)3 (trimethylphosphino) ˆ P(CF3)2 ˆ PO3H ˆ PO(OC2H5)2 ˆ SH (thio, mercapto) ˆ SCH3 (methylthio) ˆ S(CH3)2 (dimethylsulfonium) ˆ SCH2CH3 (ethylthio) ˆ SCH2CH2CH3 (propylthio) ˆ SCH2CH2CH2CH3 (butylthio) ˆ SC6H11 (cyclohexylthio) ˆ SC6H5 (phenylthio) ˆ SC(C6H5)3 (triphenylmethylthio) ˆ SCH2C6H5 (benzylthio) ˆ SCH2CH2C6H5 (phenethylthio) ˆ CH2SH (thiomethyl) ˆ CH2SCH2C6H5 ˆ SCF3 (trifluoromethylthio) ˆ SCN (thiocyanato)

0.39

0.08

0.12 0.31

0.08

0.24 0.10

0.1 0.8 0.6 0.2 0.55 0.25 0.15 1.0 0.23

0.05 0.9 0.7 0.26 0.60 0.15 0.00 0.9 0.03

0.30

0.03 0.40 0.63

0.50 0.52

3.86 1.81 2.92 0.27 0.31 0.52 0.12 0.50 0.06 0.25

1.68 1.56 1.56 1.49 1.44 1.93 1.87 0.69 1.56 1.44 0.62 0.37 3.43

7.8

SECTION 7

TABLE 7.1 Hammett and Taft Substituent Constants (continued ) Hammett constants 

Substituent ˆ S ˆ CO ˆ CH3 ˆ S ˆ CO ˆ NH2 ˆ SO ˆ CH3 (methylsulfoxy) ˆ SO ˆ C6H5 (phenylsulfoxy) ˆ CH2 ˆ SO ˆ CH3 ˆ SO2 ˆ CH3 (methylsulfonyl) ˆ SO2 ˆ CH2CH3 (ethylsulfonyl) ˆ SO2 ˆ CH2CH2CH3 (propylsulfonyl) ˆ SO2 ˆ C6H5 (phenylsulfonyl) ˆ SO2 ˆ CF3 (trifluoromethylsulfonyl) ˆ SO2 ˆ NH2 ˆ CH2 ˆ SO2 ˆ CH3 ˆ SO3 ˆ SO3H ˆ SeCH3 ˆ Se ˆ C6H11 (cyclohexylselenyl) ˆ SeCN ˆ Si (CH3)3 ˆ Si(CH2CH3)3 ˆ Si(CH3)2C6H5 ˆ Si(CH3)2 ˆ O ˆ Si(CH3)3 ˆ CH2Si(CH3)3 ˆ CH2CH2Si(CH3)3 ˆ Sn(CH3)3 ˆ Sn(CH2CH3)3

p

0.39 0.34 0.52

Taft constant *

0.44 2.07 0.49

0.60

0.68

0.67 0.79 0.46

0.93 0.57

0.05

0.09 0.50 0.0

0.1 0.67 0.04

0.66 0.07 0.0

0.16

0.22

3.24 1.33 3.68 3.74 3.68 3.55

1.38 0.81

2.37 3.61 0.81 0.87 0.81 0.25 0.25

0.0 0.0

TABLE 7.2 pKA and Rho () Values for the Hammett Equation Acid

pKA



3.54 8.49

1.05 0.87

9.70

2.15

1.84 6.97

0.76 0.95

10.70 4.78 10.00

0.86 1.03 1.06

8.31

1.16

AsO3H2 Y

(arenearsonic acids) pK1 pK2 B(OH)2

(areneboronic acids, in aqueous 25% ethanol)

Y

PO3H2 Y

(arenephosphonic acids) pK1 pK2 H C

Y

N

OH

(-arylaldoximes) Ar ˆ Se(O)OH (benzeneseleninic acids) Ar ˆ SO2 ˆ NH2 (benzenesulfonamides, 20 C) Ar1 ˆ SO2 ˆ NHAr2 (benzenesulfonanilides, 20 C) Y ˆ C6H4 ˆSO2 ˆNH ˆ C6H5

7.9

PHYSICOCHEMICAL RELATIONSHIPS

TABLE 7.2 pKA and Rho () Values for the Hammett Equation (continued) Acid

pKA



C6H5 ˆ SO2 ˆ NH ˆ C6H4 ˆ Y Ar ˆ CO ˆ OH (benzoic acids)

8.31 4.21

1.74 1.00

Y

H C

C H

COOH

(cinnamic acids)

4.45

0.47

9.92

2.23

4.30

0.49

3.24

0.81

4.45

0.21

11.90

1.01

(pyridine-1-oxides, pyridine-N-oxides)

0.94

2.09

(2-pyridones, 2-hydroxypyridines)

11.65

4.28

(4-pyridones, 4-hydroxypyridines)

11.12

4.28

(pyrroles)

17.00

4.28

2.82

1.40

2.61 6.50

1.0 2.2

(trifluoroacetophenone hydrates)

10.00

1.11

(5-substituted tropolones)

6.42

3.10

6.0 4.60

2.6 2.90

(C-aryl-N,N-dibutylamidines, in aqueous 50% ethanol) N,N-Dimethylanilines

11.14

1.41

5.07

3.46

N (isoquinolines) 1-Naphthylamines 2-Naphthylamines Pyridines

5.32 3.85 4.29 5.18

5.90 2.81 2.81 5.90

4.88

5.90

Ar ˆ OH (phenols) Y CH2COOH

(phenylacetic acids)

Y C

C

COOH

(phenylpropiolic acids, in aqueous 35% dioxane)

(CH2)2COOH Y

(phenylpropionic acids)

Ar ˆ CHOH ˆ CF3 (phenyltrifluoromethylcarbinols) N+ O–

Y N

OH

HO Y

N

Y

NH

Y

COOH

(5-substituted pyrrole-2-carboxylic acids) Ar ˆ CO ˆ SH (thiobenzoic acids) Ar ˆ SH (thiophenols) N H

HO

C

Y

Y

OH CF3

O OH

Cations resulting from protonation of Ar ˆ CO ˆ CH3 (acetophenones) Ar ˆ NH2 (anilines) HN Bu C N Bu

Y

N

(quinolines)

7.10

SECTION 7

TABLE 7.3 pKA and Rho ( ) Values for the Taft Equation Acid

pKA

RCOOH RCH2COOH RC ˜ C ˆ COOH H2C ¨ C(R) ˆ COOH (CH3)2C ¨ C(R) ˆ COOH Z-C6H5 ˆ CH ¨ C(R) ˆ COOH E-C6H5 ˆ CH ¨ C(R) ˆ COOH R ˆ CO ˆ CH2 ˆ COOH HO ˆ N ¨ CR ˆ COOH RCH2OH RCH(OH)2 R1CO ˆ NHR2 CH3CO ˆ CR ¨ C(OH)CH3 CH3CO ˆ CHR ˆ CO ˆ OC2H5 R ˆ CO ˆ NHOH R1R2C ¨ N ˆ OH (R1, R2 are not acyl groups) HO R

Rho ()

4.66 4.76 2.39 4.39 4.65 3.77 4.61 4.12 4.84 15.9 14.4 22.0 9.25 12.59 9.48 12.35 9.00

1.62 0.67 1.89 0.64 0.47 0.63 0.47 0.43 0.34 1.42 1.42 3.1* 1.78 3.44 0.98 1.18 0.94

5.24 10.22 10.54 3.52

3.60 3.50 1.47 1.62

10.15 10.59 9.61 3.59 7.85

3.14 3.23 3.30 2.61 2.67

N C

C

CH3

O

RCH(NO2)2 RSH RCH2SH R ˆ CO ˆ SH Cations resulting from protonation of RNH2 R1R2NH R1R2R3N R1R2PH R1R2R3P ** for R1CO and R2

TABLE 7.4 Special Hammett Sigma Constants Substituent

m

ˆ CH3 ˆ C(CH3)3 ˆ C6H5 ˆ CF3 ˆF ˆ Cl ˆ Br ˆI ˆC˜N ˆ CH ¨ O

0.07 0.06 0.11 0.52 0.35 0.40 0.41 0.36 0.56

p

p

0.31 0.26 0.18 0.61 0.07 0.11 0.15 0.14 0.66

0.17

0.74 0.02 0.23 0.26 0.88 1.13

7.11

PHYSICOCHEMICAL RELATIONSHIPS

TABLE 7.4 Special Hammett Sigma Constants (continued ) Substituent ˆ CO ˆ NH2 ˆ CO ˆ CH3 ˆ COOH ˆ CO ˆ OCH3 ˆ CO ˆ OCH2CH3 ˆ N2 ˆ NH2 ˆ N(CH3)2 ˆ N(CH3)3 ˆ NH ˆ CO ˆ CH3 ˆ NO2 ˆ OH ˆ O ˆ OCH3 ˆ SF5 ˆ SCF3 ˆ SO2CH3 ˆ SO2CF3

m

p

p

0.32 0.37 0.37

0.42 0.49 0.48

0.16

1.3 1.7 0.41 0.60 0.79 0.92

0.63 0.85 0.73 0.66 0.68 3.2 0.66

0.36 0.67

0.05

0.78

1.25 0.81 0.27 0.70 0.57 1.05 1.36

SECTION 8

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

EQUILIBRIUM CONSTANTS . . . . . . . . . . . . . . . . . . . . . . . . Table 8.1 pKA Values of Organic Materials in Water at 25 C . . . . Table 8.2 Proton-Transfer Reactions of Inorganic Materials in Water at 25 C . . . . . . . . . . . . . . . . . . . . . . Table 8.3 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures . . . . . . . . Table 8.4 Indicators for Aqueous Acid–Base Titrations . . . . . . . BUFFER SOLUTIONS . . . . . . . . . . . . . . . . . . . . . . . . . . . . Table 8.5 National Institute of Standards and Technology (formerly National Bureau of (Standards U.S.) Reference pH Buffer Solutions . . . . . . . . . . . . . . . . . . . . . . . . . . Table 8.6 Compositions of National Institute of Standards and Technology. Standard PH Buffer Solutions . . . . . . . . Table 8.7 pH Values of Buffer Solutions for Control Purposes . . . REFERENCE ELECTRODES . . . . . . . . . . . . . . . . . . . . . . . . Table 8.8 Potentials of Reference Electrodes (in Volts) as a Function of Temperature . . . . . . . . . . . . . . . . . . Table 8.9 Potentials of Reference Electrodes (in Volts) at 25 C for Water–Organic Solvent Mixtures . . . . . . . ELECTRODE POTENTIALS . . . . . . . . . . . . . . . . . . . . . . . . . Table 8.10 Potentials of Selected Half-Reactions at 25 C . . . . . . Table 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C . . . . . . . .

8.1

. . . . . .

8.2 8.3

. . .

8.61

. . . . . . . . .

8.64 8.72 8.74

. . .

8.74

. . . . . . . . .

8.75 8.76 8.77

. . .

8.77

. . . . . . . . .

8.79 8.80 8.80

. . .

8.82

8.2

SECTION 8

EQUILIBRIUM CONSTANTS The acidities of organic compounds are typically expressed by citing their pKA values. These are defined as log10 KA for the reaction HA 7 H  A The equilibrium constant KA is defined as KA 

[H] [A] [HA]

Thus, for example, the pKA of water is log10 ([H ][HO]/[H2O]) or (107) · (107)/55.5. The concentration of protons or hydroxide ions in water is 107 M and the concentration of water in water is 55.5 M. The equilibrium constant KA is therefore 1015.74. The operator “p” means “log” so the pKA of water is 15.7. The equilibrium constant KW for water is 1014 and is simply the product of [H ] · [HO].

O N N H 3-acetamidopyridine

Acidity constants are given for a range of compounds in Table 8.1. When more than one ionizable proton is present, pK1, pK2, etc. values are given. Cations formed from the indicated compound by protonation are indicated by “(1)” or “(2)” for a dication. For example, the dissociation of 3-acetamidopyridine is reported in Table 8.1 as “4.37(1).” This means dissociation of the compound that is protonated (at the pyridine nitrogen atom). Temperature values different from 25 C are given in parentheses as are other relevant variations. For example, the dissociation constant for acetic acid-d1 is reported in D2O.

8.3

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C Ionic strength  is zero unless otherwise indicated. The protonation state of cations is designated by a value (1), (2), etc. that follows the pKA value. Neutral species are indicated by (0), if it is not obvious otherwise. The charge state of anionic species is designated by (1), (2), etc. Substance Abietic acid Acetamide Acetamidine N-(2-Acetamido)-2aminoethanesulfonic acid (20 C) 2-Acetamidobenzoic acid 3-Acetamidobenzoic acid 4-Acetamidobenzoic acid 2-(Acetamido)butanoic acid N-(2-Acetamido)iminodiacetic acid (20 C) 3-Acetamidopyridine Acetanilide Acetic acid Acetic acid-d (in D2O) Acetoacetic acid (18 C) Acetohydrazine Acetone oxime 2-Acetoxybenzoic acid (acetylsalicylic acid) 3-Acetoxybenzoic acid 4-Acetoxybenzoic acid Acetylacetic acid (18 C) N-Acetyl--alanine N-Acetyl--alanine 2-Acetylaminobutanoic acid 3-Acetylaminopropionic acid 2-Acetylbenzoic acid 3-Acetylbenzoic acid 4-Acetylbenzoic acid 2-Acetylcyclohexanone N-Acetylcysteine (30 C) Acetylenedicarboxylic acid N-Acetylglycine

pK1

pK2

7.62 0.37(1) 1.60(1)

6.88 3.63 4.07 4.28 3.716 6.62 4.37(1) 0.4(1) 4.756 5.32 3.58 3.24(1) 12.2 3.48 4.00 4.38 3.58 3.715 4.455 3.72 4.445 4.13 3.83 3.70 14.1 9.52 1.75 3.670

H

O HO Abietic acid

13.39(0)40 C

4.40

pK3

pK4

8.4

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

N-Acetylguanidine N--Acetyl-L-histidine Acetylhydroxamic acid (20 C) N-Acetyl-2-mercaptoethylamine 4-Acetyl--mercaptoisoleucine (30 C) 2-Acetyl-1-naphthol (30 C) N-Acetylpenicillamine (30 C) 2-Acetylphenol 4-Acetylphenol 2-Acetylpyridine 3-Acetypyridine 4-Acetylpyridine Aconitine Acridine Acrylic acid Adenine Adeninedeoxyriboside-5phosphoric acid Adenine-N-oxide Adenosine Adenosine-5-diphosphoric acid Adenosine-2-phosphoric acid Adenosine-3-phosphoric acid Adenosine-5-phosphoric acid Adenosine-5-triphosphoric acid Adipamic acid (adipic acid monoamide) Adipic acid -Alanine -Alanine -Alanine, methyl ester (  0.10) -Alanine, methyl ester (  0.10) N-D-Alanyl--D-alanine (  0.1) N-L-Alanyl--L-alanine (  0.1) N-L-Alanyl--D-alanine N--Alanylglycine

pK2

pK3

8.23(1) 7.08 9.40 9.92(SH) 10.30 13.40 9.90 9.19 8.05 2.643(1) 3.256(1) 3.505(1) 8.11(1) 5.60(1) 4.26 4.17(1)

9.75(0) 4.4 8.49(0) 12.34(0) 4.2(1) 6.17(0) 5.88(1) 6.05(1) 4.00(1)

2.69(1) 3.5(1) 3.81(1) 3.65(0) 3.74(0)

4.629 4.418 2.34(1) 3.55(1) 7.743(1) 9.170(1) 3.32(1) 3.32(1) 3.12(1) 3.11(1)

6.4

7.20(2)

13.06(2) 6.48(2)

5.412 9.87(0) 10.238(0)

8.13(0) 8.13(0) 8.30(0) 8.11(0) O

OMe

O

O

H H

Ph OH

Et

HO

N

NH

HO

O HS N-Acetylpenicillamine

MeO

OMe OAc OH H OMe

N Acridine

Aconitine

pK4

8.5

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Alanylglycylglycine -Alanylhistidine Albumin (bovine serum,   0.15) 2-Aldoxime pyridine Alizarin Black SN Alizarin-3-sulfonic acid Allantoin Allothreonine Alloxanic acid Allylacetic acid Allylamine 5-Allylbarbituric acid 5-Allyl-5-(-methylbutyl)barbituric acid 2-Allylphenol 1-Allylpiperidine 2-Allylpropionic acid 3-Amidotetrazoline 2-Aminoacetamide Aminoacetonitrile 9-Aminoacridine (20 C) 4-Aminoantipyrine 2-Aminobenzenesulfonic acid 3-Aminobenzenesulfonic acid 4-Aminobenzenesulfonic acid 2-Aminobenzoic acid 3-Aminobenzoic acid 4-Aminobenzoic acid 2-Aminobenzoic acid, methyl ester 3-Aminobenzoic acid, methyl ester 4-Aminobenzoic acid, methyl ester

HN

3.190(1) 2.64 10–10.3 3.42(1) 5.79 5.54 8.96 2.108(1) 6.64 4.68 9.69(1) 4.78(1) 8.08 10.28 9.65(1) 4.72 3.95(1) 7.95(1) 5.34(1) 9.95(1) 4.94(1) 2.459(0) 3.738(0) 3.227(0) 2.09(1) 3.07(1) 2.41(1) 2.36(1) 3.58(1) 2.45(1)

NH2

NH2

HO O

Allothreonine

Allantoin

10.22(0) 12.8 11.01 9.096(0)

4.79(0) 4.79(0) 4.85(0)

O

N

NH N

O

O

O

N N

9-Aminoacridine

N NH

3-Aminotetrazoline

Alloxanic acid

O

H2N

N H

O

NH2

N

pK4

9.40

HO

O N H

pK3

8.15(0) 6.86

OH

O

O N H

pK2

NH2

4-Aminoantipyrine

8.6

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 3-Aminobenzonitrile 4-Aminobenzonitrile 4-Aminobenzophenone 2-Aminobenzothiazole (20 C) 2-Aminobenzoylhydrazide 2-Aminobiphenyl 3-Aminobiphenyl 4-Aminobiphenyl 4-Amino-3-bromomethylpyridine 4-Amino-3-bromopyridine (20 C) 2-Aminobutanoic acid 3-Aminobutanoic acid 4-Aminobutanoic acid 2-Aminobutanoic acid, methyl ester (  0.1) 4-Aminobutanoic acid, methyl ester (  0.1) D-()-2-Amino-1-butanol 3-Amino-N-butyl-3-methyl-2butanone oxime 4-Aminobutylphosphonic acid 2-Amino-N-carbamoylbutanoic acid 4-Amino-N-carbamoylbutanoic acid 2-Amino-N-carbamoyl-2methylpropanoic acid 1-Amino-1-cycloheptanecarboxylic acid 1-Amino-1-cyclohexanecarboxylic acid 2-Amino-1-cyclohexanecarboxylic acid 1-Aminocyclopentane 1-Aminocyclopropane 10-Aminodecylphosphonic acid 10-Aminodecylsulfonic acid 1-Amino-2-di(aminomethyl)butane 2-Amino-N,N-dihydroxyethyl2-hydroxyl-1,3-propanediol 2-Amino-N,N-dimethylbenzoic acid 4-Amino-2,5-dimethylphenol 4-Amino-3,5-dimethylpyridine (20 C) 12-Aminododecanoic acid 2-Aminoethane-1-phosphoric acid 1-Aminoethanesulfonic acid 2-Aminoethanesulfonic acid 2-Aminoethanethiol (cysteamine) (  0.01) 2-Aminoethanol (ethanolamine) 2-[2-(2-Aminoethyl) aminoethyl] pyridine

pK1 2.75(1) 1.74(1) 2.15(1) 4.48(1) 1.85 3.78(1) 4.18(1) 4.27(1) 7.47(1) 7.04(1) 2.286(1) 4.031(1)

pK2

3.47

pK3

12.80

9.830(0) 10.14(0) 10.556(0)

7.640(1) 9.838(1) 9.52(1) 9.09(1) 2.55 3.886(1) 4.683(1)

7.55

4.463 2.59(1)

10.46(0)

2.65(1)

10.03(0)

3.56(1)

10.21(0)

10.9

10.65(1) 9.10(1) 2.65(1) 3.58(3)

8.0

11.25

8.59(2)

9.66(1)

6.484(1) 1.63(1) 5.28(1) 9.54(1) 4.648(1) 5.838 0.33 1.5

10.64 9.06 9.061

8.23(1) 9.50(1) 3.50

6.59

8.42(0) 10.40(0)

9.51

pK4

8.7

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

2-Amino-2-ethyl-1-butanol 3-(2-Aminoethyl)indole 3-Amino-N-ethyl-3-methyl-2butanone oxime N-(2-Aminoethyl)morpholine p-(2-Aminoethyl)phenol 2-Aminoethylphosphonic acid N-(2-Aminoethyl)piperidine (30 C) 2-(2-Aminoethyl)pyridine (  0.5) 4-Amino-3-ethylpyridine (20 C) N-(2-Aminoethyl)pyrrolidine (30 C) 2-Aminofluorine 2-Amino-D--glucose (  0.05) 2-Amino-N-glycylbutanoic acid 7-Aminoheptanoic acid 2-Aminohexanoic acid 6-Aminohexanoic acid C-Amino-Chydrazine carbonylmethane 2-Amino-3-hydroxybenzoic acid L-2-Amino-3-hydroxybutanoic acid (threonine) DL-2-Amino-4-hydroxybutanoic acid (  0.1) DL-4-Amino-3-hydroxybutanoic acid (  0.1) 2-Amino-2-hydroxydiethyl sulfide 4-Amino-2-hydroxypyrimidine (cytosine) 3-Amino-N-isopropyl-3-methyl2-butanone oxime 4-Amino-3-isopropylpyridine (20 C) 1-Aminoisoquinoline (20 C,   0.01) 3-Aminoisoquinoline (20 C,   0.005) 4-Aminoisoxazolidine-3-one Aminomalonic acid DL-2-Amino-4-mercaptobutanoic acid

pK2

pK3

9.82(1) 10.2 9.23(1) 4.06(2) 9.3 2.45(1) 6.38 4.24(2) 9.51(1) 6.56(2) 10.34(1) 2.20(1) 3.155(1) 4.502 2.335(1) 4.373(1)

9.15(1) 10.9 7.0(0) 9.89 9.78(1) 9.74(1) 9.08(0) 8.331(0) 9.834(0) 10.804(0)

2.38(2)

7.69(1)

2.5(1)

5.192(0)

2.088(1)

9.100(0)

2.265(1)

9.257(0)

3.834(1) 9.27(1)

9.487(0)

4.58(1)

12.15(0)

10.118(OH)

9.09(1) 9.54(1) 7.62(1) 5.05(1) 7.4(1) 3.32(1)

9.83(0)

2.22(1)

8.87(0)

10.86(SH)

NH2

N H2N

2-Aminofluorene

10.8(1)

N

OH

4-Amino-2-hydroxypyrimidine (cytosine)

pK4

8.8

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2-Amino-3-mercapto3-Methylbutanoic acid 2-Amino-6-methoxybenzothiazole 3-Amino-4-methylbenzenesulfonic acid 4-Amino-3-methylbenzenesulfonic acid 2-Amino-4-methylbenzothiazole 1-Amino-3-methylbutane 3-Amino-3-methyl-2-butanone oxime 3-Amino-N-methyl-3-methyl-2butanone oxime 2-Amino-3-methylpentanoic acid 3-Aminomethyl-6-methylpyridine (30 C) Aminomethylphosphonic acid 2-Amino-2-methyl-1,3-propanediol 2-Amino-2-methyl-1-propanol 2-Amino-2-methylpropanoic acid (2-Aminomethyl)pyridine (  0.5) 2-Amino-3-methylpyridine 4-Amino-3-methylpyridine 2-Amino-4-methylpyridine 2-Amino-5-methylpyridine 2-Amino-6-methylpyridine 2-Amino-4-methylpyrimidine (20 C) Aminomethylsulfonic acid N-Aminomorpholine 4-Amino-1-naphthalenesulfonic acid 1-Amino-2-naphthalenesulfonic acid 1-Amino-3-naphthalenesulfonic acid 1-Amino-5-naphthalenesulfonic acid 1-Amino-6-naphthalenesulfonic acid 1-Amino-7-naphthalenesulfonic acid 1-Amino-8-naphthalenesulfonic acid 2-Amino-1-naphthalenesulfonic acid 2-Amino-4-naphthalenesulfonic acid 2-Amino-6-naphthalenesulfonic acid 2-Amino-8-naphthalenesulfonic acid 3-Amino-1-naphthoic acid 4-Amino-2-naphthoic acid 8-Amino-2-naphthol DL-2-Aminopentanoic acid (DL-norvaline) 3-Aminopentanoic acid 4-Aminopentanoic acid 5-Aminopentanoic acid 5-Aminopentanoic acid, ethyl ester 2-Aminophenol

pK1

pK2

pK3

1.8(1) 4.50(1)

7.9(0)

10.5(SH)

3.633 3.125 4.7(1) 10.64(1) 9.09(1) 9.23(1) 2.320(1) 8.70(1) 2.35 8.801 9.694(1) 2.357(1) 2.31(2) 7.24(1) 9.43(1) 7.48(1) 7.22(1) 7.41(1) 4.11(1) 5.75(1) 4.19(1) 2.81 1.71 3.20 3.69 3.80 3.66 5.03 2.35 3.79 3.79 3.89 2.61 2.89 4.20(1) 2.318(1) 4.02(1) 3.97(1) 4.20(1) 10.151 9.28

9.758(0)

5.9

10.205(0) 8.79(1)

8.94 4.39 4.46

9.808 10.399(0) 10.46(0) 9.758(0) 9.72

10.8

pK4

8.9

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

pK2

3-Aminophenol 4-Aminophenol 4-Aminophenylacetic acid (20 C) 2-Aminophenylarsonic acid 3-Aminophenylarsonic acid 4-Aminophenylarsonic acid 3-Aminophenylboric acid 4-Aminophenylboric acid 4-Aminophenyl (4-chlorophenyl) sulfone 2-Aminophenylphosphonic acid 3-Aminophenylphosphonic acid 4-Aminophenylphosphonic acid 1-Amino-1,2,3-propanetricarboxylic acid (  2.2) 3-Aminopropanoic acid 1-Amino-1-propanol DL-2-Amino-1-propanol 3-Amino-1-propanol 3-Aminopropene 3-Amino-N-propyl-3-methyl2-butanone oxime 2-Aminopropylsulfonic acid 2-Aminopyridine 3-Aminopyridine 4-Aminopyridine 2-Aminopyridine-1-oxide 3-Aminopyridine-1-oxide 4-Aminopyridine-1-oxide 8-Aminoquinaldine 2-Aminoquinoline (20 C,   0.01) 3-Aminoquinoline (20 C,   0.01) 4-Aminoquinoline (20 C,   0.01) 5-Aminoquinoline (20 C,   0.01) 6-Aminoquinoline (20 C,   0.01) 8-Aminoquinoline (20 C,   0.01) 4-Aminosalicylic acid 5-Aminosalicylic acid 2-Amino-3-sulfopropanoic acid 4-Amino-2,3,5,6tetramethylpyridine (20 C)

9.83 8.50 3.60 ca 2 ca 2 ca 2 4.46 3.71

9.87 10.30 5.26 3.77 4.02 4.02 8.81 9.17

pK3

8.66 8.92 8.62

1.38

2.10(1) 3.551(1) 9.96(1) 9.469(1) 9.96(1) 9.691(1)

4.10

7.29 7.16 7.53

3.60(0) 10.235(0)

4.60(1)

9.09(1) 9.15 6.71(1) 6.03(1) 9.114(1) 2.58(1) 1.47(1) 3.54(1) 4.86(1) 7.34(1) 4.95(1) 9.17(1) 5.46(1) 5.63(1) 3.99(1) 1.991(1) 2.74(1) 1.89(1)

3.917(0) 5.84(0) 8.70(0)

13.74

10.58(1) NH2 N

N+ H2N

pK4

O–

2-Aminopyridine-1-oxide

8-Aminoquinaldine

9.82(2)

8.10

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

5-Amino-1,2,3,4-tetrazole (20 C) 2-Aminothiazole (20 C) 1-Amino-3-thiobutane (30 C) 5-Amino-3-thio-1-pentanol (30 C) 2-Aminothiophenol 2-Amino-4,4,4-trifluorobutanoic acid 3-Amino-4,4,4-trifluorobutanoic acid 3-Amino-2,4,6-trinitrotoluene Angiotensin II Anhydroplatynecine Aniline 2-Anilinoethylsulfonic acid 3-Anilinoethylsulfonic acid Anthracene-1-carboxylic acid Anthracene-2-carboxylic acid Anthracene-9-carboxylic acid Anthraquinone-1-carboxylic acid (20 C) Anthraquinone-2-carboxylic acid (20 C) 9,10-Anthraquinone monoxime 9,10-Anthraquinone-1-sulfonic acid 9,10-Anthraquinone-2-sulfonic acid Antipyrine Apomorphine (15 C) D-()-Arabinose L-()-Arginine Arsenazo III [pK5  10.5(4); pK6  12.0(5)] Arsenoacetic acid Arsenoacrylic acid Arsenobutanoic acid 2-Arsenocrotonic acid 3-Arsenocrotonic acid Arsenopentanoic acid L-()-Ascorbic acid (vitamin C) L-()-Asparagine L-Asparaginylglycine D-Aspartic acid Aspartic diamide (  0.2)

1.76 5.36(1) 9.18(1) 9.12(1)  2(1)

pK2

pK3

pK4

6.07

7.90(0) 8.171(0) 5.831(0) 9.5(1)

10.37 9.40 4.60(1) 3.80(1) 4.85(1) 3.68 4.18 3.65 3.37 3.42 9.78 0.27 0.38 1.45(1) 8.92 12.34

4.17

8.994(1)

12.47(1)

1.2 4.67 4.23 4.92 4.61 4.03 4.89 11.57 8.80(0) 4.53 3.87(0)

2.7 7.68 8.60 7.64 8.75 8.81 7.75

9.07 10.00()

7.00

N N O Anhydroplatynecine

N O Antipyrine

7.9(3)

8.11

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Aspartylaspartic acid -Aspartylhistidine (38 C,   0.1) -Aspartylhistidine (38 C,   0.1) N-Aspartyl-p-tyrosine (  0.01) Aspidospermine Atropine (17 C) 1-Azacycloheptane 1-Azacyclooctane Azetidine Aziridine

pK2 3.40 3.02 2.95 3.57

pK3 4.70 6.82 6.93 8.92

pK4 8.26 7.98 8.72 10.23(OH)

7.65 4.35(1) 11.11(1) 11.1(1) 11.29(1) 8.04(1)

Barbituric acid m-Benzbetaine p-Benzbetaine Benzenearsonic acid (22 C) Benzene-1-arsonic acid-4-carboxylic acid

8.372(0) 3.217(1) 3.245(1) 8.48(1)

Benzeneboronic acid Benzene-1-carboxylic acid2-phosphoric acid Benzene-1-carboxylic acid3-phosphoric acid Benzene-1-carboxylic acid4-phosphoric acid Benzenediazine 1,3-Benzenedicarboxylic acid (isophthalic acid) 1,4-Benzenedicarboxylic acid (terephthalic acid) 1,3-Benzenedicarboxylic acid mononitrile 1,4-Benzenedicarboxylic acid mononitrile Benzenehexacarboxylic acid (pK5  6.32; pK6  7.49) Benzenepentacarboxylic acid (pK5  6.46) Benzenesulfinic acid Benzenesulfonic acid 1,2,3,4-Benzenetetracarboxylic acid

4.22 (COOH)

5.59

3.78

9.17

4.03

7.03

1.50 11.08(1)

3.95

6.89

3.62(0)

4.60(1)

3.54(0)

4.46(1)

13.7

3.60(0) 3.55(0)

NH Azetidine

0.68

2.21

3.52

5.09

1.80 1.50 2.554 2.05

2.73

3.96

5.25

3.25

4.73

6.21

HN Aziridine (ethyleneimine)

8.12

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

1,2,3,5-Benzenetetracarboxylic acid 1,2,4,5-Benzenetetracarboxylic acid 1,2,3-Benzenetricarboxylic acid 1,2,4-Benzenetricarboxylic acid 1,3,5-Benzenetricarboxylic acid Benzil--dioxime Benzilic acid Benzimidazole Benzohydroxamic acid (20 C) Benzoic acid 5,6-Benzoquinoline (20 C) 7,8-Benzoquinoline (20 C) 1,4-Benzoquinone monoxime Benzosulfonic acid 1,2,3-Benzotriazole 1-Benzoylacetone Benzoylamine 2-Benzoylbenzoic acid Benzoylglutamic acid N-Benzoyglycine (hippuric acid) Benzoylhydrazine Benzoylpyruvic acid 3-Benzoyl-1,1,1-trifluoroacetone Benzylamine Benzylamine-4-carboxylic acid 2-Benzyl-2-phenylsuccinic acid (20 C) 2-Benzylpyridine 4-Benzylpyridine-1-oxide 1-Benzylpyrrolidine 2-Benzylpyrrolidine Benzylsuccinic acid (20 C) 3-(Benzylthio)propanoic acid Berberine (18 C) Betaine Biguanide 2,2-Biimidazolyl (  0.3) 2-Biphenylcarboxylic acid

pK2

2.38 1.92 2.88 2.52 2.12 12.0 3.09 5.53(1) 8.89(0) 4.204 5.00(1) 4.15(1) 6.20 0.70 8.38(1) 8.23 9.34(1) 3.54 3.49 3.65 3.03(2) 6.40 6.35 9.35(1) 3.59

3.51 2.87 4.75 3.84 4.10

3.69 5.13(1) 1.018() 9.51(1) 10.31(1) 4.11 4.463 11.73(1) 1.832(1) 2.96(2) 5.01(1) 3.46

6.47

pK3 4.44 4.49 7.13 5.20 5.18

5.81 5.63

12.3(0)

4.99 12.45(1) 12.10

9.64

5.65

11.51(1)

NH

NH

N

HO HO

pK4

H2N

O

Benzilic acid

5,6-Benzoquinoline

N H Biguanide

NH2

8.13

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

(1,1-Biphenyl)-4,4-diamine Bis(2-aminoethyl) ether (30 C) N,N-Bis(2-aminoethyl)ethylenediamine (20 C) N,N-Bis(2-hydroxyethyl)-2aminoethane sulfonic acid (BES) (20 C) N,N-Bis(2-hydroxyethyl)glycine (bicine) (20 C) Bis(2-hydroxyethyl)iminotris (hydroxymethyl)methane (bis-tris) 1,3-Bis[tris(hydroxymethyl) methylamino]propane (20 C) Bromoaetic acid 2-Bromoaniline 3-Bromoaniline 4-Bromoaniline 2-Bromobenzoic acid 3-Bromobenzoic acid 4-Bromobenzoic acid 2-Bromobutanoic acid (35 C) erythro-2-Bromo-3-chlorosuccinic acid (19 C,   0.1) threo-2-Bromo-chlorosuccinic acid (19 C,   0.1) trans-2-Bromocinnamic acid 3-Bromo-4-(dimethylamino)pyridine (20 C) 2-Bromo-4,6-dinitroaniline 3-Bromo-2-hydroxymethylbenzoic acid (20 C) 6-Bromo-2-hydroxymethylbenzoic acid (20 C) 7-Bromo-8-hydroxyquinoline5-sulfonic acid 3-Bromomandelic acid 3-Bromo-4-methylaminopyridine (20 C) (2-Bromomethyl)butanoic acid Bromomethylphosphonic acid

pK2

3.63(2) 8.62(2)

4.70(1) 9.59(1)

3.32(4)

6.67(3)

7.15 8.35

6.46(1) 6.80(1) 2.902 2.53(1) 3.53(1) 3.88(1) 2.85 3.810 3.99 2.939 1.4

2.6

1.5 4.41

2.8

6.52(1) 6.94(1) 3.28 2.25 2.51 3.13

6.70

7.49(1) 3.92 1.14

6.52 O

Br

OH OH 3-Bromomandelic acid

pK3

pK4

9.20(2)

9.92(1)

8.14

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2-Bromo-6-nitrobenzoic acid 2-Bromophenol 3-Bromophenol 4-Bromophenol 2-(2-Bromophenoxy)acetic acid 2-(3-Bromophenoxy)acetic acid 2-(4-Bromophenoxy) acetic acid 2-Bromo-2-phenylacetic acid 2-(Bromophenyl)acetic acid 4-(Bromophenyl)acetic acid 4-Bromophenylarsonic acid 4-Bromophenylphosphinic acid (17 C) 2-Bromophenylphosphonic acid 3-Bromophenylphosphonic acid 4-Bromophenylphosphonic acid 3-Bromophenylselenic acid 4-Bromophenylselenic acid 2-Bromopropanoic acid 3-Bromopropanoic acid Bromopropynoic acid 2-Bromopyridine 3-Bromopyridine 4-Bromopyridine 3-Bromoquinoline Bromosuccinic acid 2-Bromo-p-tolylphosphonic acid Brucine (15 C) 2-Butanamine (sec-butylamine) 1,2-Butanediamine 1,4-Butanediamine 2,3-Butanediamine 1,2,3,4-Butanetetracarboxylic acid cis-2-Butenoic acid (isocrotonic acid) trans-2-Butenoic acid (transcrotonic acid) (35 C) 3-Butenoic acid (vinylacetic acid) 3-Butoxybenzoic acid (20 C) Butylamine tert-Butylamine 4-tert-Butylaniline N-tert-Butylaniline Butylarsonic acid (18 C) 2-tert-Butylbenzoic acid 3-tert-Butylbenzoic acid 4-tert-Butylbenzoic acid N-Butylethylenediamine N-Butylglycine

pK1 1.37 8.452 9.031 9.34 3.12 3.09 3.13 2.21 4.054 4.188 3.25 2.1 1.64 1.45 1.60 4.43 4.50 2.971 3.992 1.855 0.71(1) 2.85(1) 3.71(1) 2.69(1) 2.55 1.81 2.50(2) 10.56(1) 6.399(2) 9.35(2) 6.91(2) 3.43

pK2

pK4

8.19

7.00 6.69 6.83

4.41 7.15 8.16(1) 9.388(1) 10.82(1) 10.00(1) 4.58

4.44 4.676 4.68 4.25 10.64(1) 10.685(1) 3.78(1) 7.10(1) 4.23 3.57 4.199 4.389 7.53(2) 2.35(1)

pK3

8.91

10.30(1) 10.25(0)

5.85

7.16

8.15

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

tert-Butylhydroperoxide 1-(tert-Butyl)-2-hydroxybenzene 1-(tert-Butyl)-3-hydroxybenzene 1-(tert-Butyl)-4-hydroxybenzene Butylmethylamine 2-Butyl-1-methyl-2-pyrroline 4-tert-Butylphenylactic acid Butylphosphinic acid tert-Butylphosphinic acid tert-Butylphosphonic acid 1-Butylpiperidine (  0.02) 2-tert-Butylpyridine 3-tert-Butylpyridine 4-tert-Butylpyridine 2-tert-Butylthiazole (  0.1) 4-tert-Butylthiazole (  0.1) 2-Butyn-1,4-dioic acid 2-Butynoic acid (tetrolic acid) Butyric acid 4-Butyrobetaine (20 C)

12.80 10.62 10.119 10.23 10.90(1) 11.84(1) 4.417 3.41 4.24 2.79 10.43(1) 5.76(1) 5.82(1) 5.99(1) 3.00(1) 3.04(1) 1.75 2.620 4.817 3.94(1)

Caffeine (40 C) Calcein (pK5  12) Calmagite D-Camphoric acid Canaline Canavanine N-Carbamoylacetic acid N-Carbamoyl--D-alanine N-Carbamoyl--alanine DL-N-Carbamoylalanine N-Carbamoylglycine 2-Carbamoylpyridine (20 C) 3-Carbamoylpyridine 4-Carbamoylpyridine (20 C) -Carboxymethylaminopropanoic acid Chloroacetic acid N-(2-Chloroacetyl)glycine cis-3-Chloroacrylic acid (18 C,   0.1) trans-3-chloroacrylic acid (18 C,   0.1) 2-Chloroaniline 3-Chloroaniline 4-Chloroaniline 2-Chlorobenzoic acid 3-Chlorobenzoic acid 4-Chlorobenzoic acid 2-Chlorobutanoic acid

10.4 4 8.14 4.57 2.40 2.50(2) 3.64 3.89(1) 4.99(1) 3.892(1) 3.876 2.10(1) 3.328(1) 3.61(1) 3.61(1) 2.867 3.38(0) 3.32 3.65 2.64(1) 3.52(1) 3.99(1) 2.877 3.83 3.986 2.86

pK2

pK3

pK4

8.88

4.40

5.4 12.35 5.10 3.70 6.60(1)

9.46(0)

9.0

9.20 9.25(0)

10.5

8.16

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 3-Chlorobutanoic acid 4-Chlorobutanoic acid 2-Chloro-3-butenoic acid 3-Chlorobutylarsonic acid (18 C) trans-2-Chlorocinnamic acid trans-3-Chlorocinnamic acid trans-4-Chlorocinnamic acid 2-Chlorocrotonic acid 3-Chlorocrotonic acid Chlorodifluoroacetic acid 1-Chloro-1,2-dihydroxybenzene 1-Chloro-2,6-dimethyl4-hydroxybenzene 4-Chloro-2,6-dinitrophenol 2-Chloroethylarsonic acid 3-Chlorohexyl-1-arsonic acid (18 C) 2-Chloro-3-hydroxybutanoic acid 3-Chloro-2-(hydroxymethyl)benzoic acid (20 C) 6-Chloro-2-(hydroxymethyl)benzoic acid (20 C) 7-Chloro-8-hydroxyquinoline5-sulfonic acid 2-Chloroisocrotonic acid 3-Chloroisocrotonic acid 3-Chlorolactic acid 3-Chloromandelic acid 3-Chloro-4-methoxyphenylphosphonic acid 3-Chloro-4-methylaniline 4-Chloro-N-methylaniline 4-Chloro-3-methylphenol Chloromethylphosphonic acid 2-Chloro-2-methylpropanoic acid 2-Chloro-6-nitroaniline 4-Chloro-2-nitroaniline 2-Chloro-3-nitrobenzoic acid 2-Chloro-4-nitrobenzoic acid 2-Chloro-5-nitrobenzoic acid 2-Chloro-6-nitrobenzoic acid 4-Chloro-2-nitrophenol

pK1

pK2

4.05 4.50 2.54 3.95 4.234 4.294 4.413 3.14 3.84 0.46 8.522

8.85

9.549 2.97 3.68 3.51 2.59

8.37 8.31

3.27 2.26 2.92 2.80 4.02 3.12 3.237

6.80

2.25 4.05(1) 3.9(1) 9.549 1.40 2.975 2.41(1) 1.10(1) 2.02 1.96 2.17 1.342 6.48

6.7

6.30

HO O Cl

2-Chloroisocrotonic acid

pK3

pK4

8.17

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2-Chlorophenol 3-Chlorophenol 4-Chlorophenol (4-Chloro-3-nitrophenoxy)acetic acid 2-Chloro-4-nitrophenylphosphonic acid 3-Chloropentyl-l-arsonic acid (18 C) 2-Chlorophenoxyacetic acid 3-Chlorophenoxyacetic acid 4-Chlorophenoxyacetic acid 4-Chlorophenoxy-2-methylacetic acid 2-Chlorophenylacetic acid 3-Chlorophenylacetic acid 4-Chlorophenylacetic acid 2-Chlorophenylalanine 3-Chlorophenylalanine DL-4-Chlorophenylalanine 4-Chlorophenylarsonic acid 2-Chlorophenylphosphonic acid 3-Chlorophenylphosphonic acid 4-Chlorophenylphosphonic acid 3-(2-Chlorophenyl)propanoic acid 3-(3-Chlorophenyl)propanoic acid 3-(4-Chlorophenyl)propanoic acid 3-Chlorophenylselenic acid 4-Chlorophenylselenic acid 4-Chloro-1,2-phthalic acid 2-Chloropropanoic acid 3-Chloropropanoic acid 2-Chloropropylarsonic acid (18 C) 3-Chloropropylarsonic acid (18 C) Chloropropynoic acid 2-Chloropyridine 3-Chloropyridine 4-Chloropyridine 7-Chlorotetracycline 4-Chloro-2-(2-thiazolylazo)phenol 4-Chlorothiophenol N-Chloro-p-toluenesulfonamide 3-Chloro-o-toluidine 4-Chloro-o-toluidine 5-Chloro-o-toluidine 6-Chloro-o-toludine Chrome Azurol S Chrome Dark Blue Cinchonine

pK1

pK2

pK3

8.55 9.10 9.43 2.959 1.12

6.14

3.71 3.05 3.07 3.10

8.77

3.26 4.066 4.140 4.190 2.23(1) 2.17(1) 2.08(1) 3.33 1.63 1.55 1.66 4.577 4.585 4.607 4.47 4.48 1.60 2.84 3.992 3.76 3.63 1.845 0.49(1) 2.84(1) 3.83(1) 3.30(1) 7.09 5.9 4.54(1) 2.49(1) 3.385(1) 3.85(1) 3.62(1) 2.45 7.56 5.85(2)

8.94(0) 8.91(0) 8.96(0) 8.25 6.98 6.65 6.75

8.39 8.53

7.44

9.27

4.86 9.3 9.92(1)

11.47 12.4

pK4

8.18

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

cis-Cinnamic acid trans-Cinnamic acid Citraconic acid Citric acid L-()-Citrulline Cocaine Codeine Colchicine Coniine (  0.5) Creatine (40 C) Creatinine o-Cresol m-Cresol p-Cresol Cumene hydroperoxide Cupreine Cyanamide Cyanoacetic acid Cyanoacetohydrazide 2-Cyanobenzoic acid 3-Cyanobenzoic acid 4-Cyanobenzoic acid 4-Cyanobutanoic acid trans-1-Cyanocyclohexane2-carboxylic acid 4-Cyano-2,6-dimethylphenol 4-Cyano-3,5-dimethylphenol 2-Cyanoethylamine N-(2-Cyano)ethylnorcodeine Cyanomethylamine 2-Cyano-2-methyl-2-phenylacetic acid 1-Cyanomethylpiperidine 2-Cyano-2-methylpropanoic acid 3-Cyanophenol o-Cyanophenoxyacetic acid m-Cyanophenoxyacetic acid p-Cyanophenoxyacetic acid 2-Cyanopropanoic acid 3-Cyanopropanoic acid 2-Cyanopyridine

3.879 4.438 2.29(0) 3.128 2.43(1) 8.41(1) 7.95(1) 1.65(1) 11.24(1) 3.28(1) 3.57(1) 10.26 10.00 10.26 12.60 7.63(1) 10.27 2.460 2.34(2) 3.14 3.60 3.55 4.44

pK2

6.15(1) 4.761 9.41(0)

O

cis -Cinnamic acid

6.396

3.865 8.27 8.21 7.7(1) 5.68(1) 5.34(1) 2.290 4.55(1) 2.422 8.61 2.98 3.03 2.93 2.37 3.99 0.26(1) OH

OH

HO HO

O

HO

pK4

11.17(1)

O

O

pK3

OH

OOH

O

OH

Citraconic acid

O

Citric acid

Cumene hydroperoxide

8.19

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 3-Cyanopyridine 4-Cyanopyridine Cyanuric acid Cyclobutanecarboxylic acid 1,1-Cyclobutanedicarboxylic acid cis-1,2-Cyclobutanedicarboxylic acid trans-1,2-Cyclobutanedicarboxylic acid cis-1,3-Cyclobutanedicarboxylic acid trans-1,3-Cyclobutanedicarboxylic acid Cyclohexanecarboxylic acid 1,1-Cyclohexanediacetic acid cis-1,2-Cyclohexanediacetic acid (20 C) trans-1,2-Cyclohexanediacetic acid (20 C) cis-1,2-Cyclohexanediamine trans-1,2-Cyclohexanediamine 1,1-Cyclohexanedicarboxylic acid cis-1,2-Cyclohexanedicarboxylic acid (20 C) trans-1,2-Cyclohexanedicarboxylic acid (20 C) cis-1,3-Cyclohexanedicarboxylic acid (16 C) trans-1,3-Cyclohexanedicarboxylic acid (19 C) trans-1,4-Cyclohexanedicarboxylic acid (16 C) 1,3-Cyclohexanedione cis,cis-1,3,5-Cyclohexanetriamine Cyclohexanonimine cis-4-Cyclohexene-1,2-dicarboxylic acid (20 C) trans-4-Cyclohexene-1,2-dicarboxylic acid (20 C) Cyclohexylacetic acid Cyclohexylamine 2-(Cyclohexylamino)ethanesulfonic acid (CHES) (20 C)

pK1

pK2

1.45(1) 1.90(1) 6.78 4.785 3.13 3.90

5.88 5.89

3.79 4.04

5.61 5.31

3.81 4.90 3.49

5.28 6.96

4.42

5.45

4.38 6.43(2) 6.34(2) 3.45

5.42 9.93(1) 9.74(1) 4.11

4.34

6.76

4.18

5.93

4.10

5.46

4.31

5.73

4.18 5.26 6.9(3) 9.15

5.42

3.89

6.79

3.95 4.51 10.64(1)

5.81

8.7(2)

9.55 OH N HO

N N OH

Cyanuric acid

pK3

10.4(1)

pK4

8.20

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

3-Cyclohexylamino1-propanesulfonic acid (CAPS) (20 C) 4-Cyclohexylbutanoic acid Cyclohexylcyanoacetic acid 1,2-Cyclohexylenedinitriloacetic acid (  0.1) 3-Cyclohexylpropanoic acid 2-Cyclohexylpyrrolidine 2-Cyclohexyl-2-pyrroline Cyclohexylthioacetic acid Cyclopentanecarboxylic acid cis-Cyclopentane-1-carboxylic acid2-acetic acid trans-Cyclopentane-1-carboxylic acid-2-acetic acid Cyclopentane-1,2-diamine-N,N,Ntetraacetic acid (  0.1) Cyclopentane-1,1-dicarboxylic acid cis-Cyclopentane-1,2-dicarboxylic acid trans-Cyclopentane-1,2-dicarboxylic acid cis-Cyclopentane-1,3-dicarboxylic acid trans-Cyclopentane-1,3-dicarboxylic acid Cyclopentylamine 1,1-Cyclopentyldiacetic acid cis-Cyclopentyl-1,2-diacetic acid trans-Cyclopentyl-1,2-diacetic acid Cyclopropanecarboxylic acid Cyclopropane-1,1-dicarboxylic acid cis-Cyclopropane-1,2-dicarboxylic acid trans-Cyclopropane-1,2-dicarboxylic acid Cyclopropylamine 5-Cyclopropyl-1,2,3,4-tetrazole L-Cysteic acid (3-sulfo-L-alanine) L-()-Cysteine

pK2

pK3

pK4

10.40 4.95 2.367 2.4 4.91 10.76(1) 7.91(1) 3.488 4.905

3.5

4.40

5.79

4.39

5.67

3.23

4.08

4.43

6.67

3.96

5.85

4.26

5.51

4.32 10.65(1) 3.80 4.42 4.43 4.827 1.82

5.42

5.43

3.33

6.47

3.65 9.10(1) 4.90(1) 1.89(1) 1.71(1)

5.13

6.16

12.35

10.20

6.77 5.42 5.43

8.7(0) 8.39(0)

H N N

N N

5-Cyclopropyl-1,2,3,4-tetrazole

10.70(SH)

8.21

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

L-()-Cysteine, ethyl ester

6.69 (NH3) 6.56 (NH3) 2.97 1.6(2) 3.12 4.08(1) 0.8(1) 0.80(1)

L-()-Cysteine, methyl ester L-Cysteinyl-L-asparagine L-Cystine (35 C)

Cystinylglycylglycine (35 C) Cytidine Cytidine-2-phosphoric acid Cytidine-3-phosphoric acid Cytidine-5-phosphoric acid Cytosine

4.58(1)

Decanedioic acid (sebacic acid) Dehydroascorbic acid (20 C) 2-Deoxyadenosine (  0.1) Deoxycholic acid 2-Deoxyglucose 2-Deoxyguanosine (  0.1) 5-Desoxypyridoxal (  0) 1,1-Diacetic acid semicarbazide (30 C,   0.1) Diacetylacetone Diallylamine (  0.02) 5,5-Diallylbarbituric acid 1,3-Diamino-2-aminomethylpropane 3,5-Diaminobenzoic acid 1,3-Diamino-N,N-bis(2-aminoethyl)propane (  0.5) 2,4-Diaminobutanoic acid (20 C) 2,2-Diaminodiethyl sulfide (30 C) 1,8-Diamino-3,6-dithiooctane (30 C) 2,7-Diaminooctanedioic acid (20 C,   0.1) 1,8-Diamino-3,6-octanedione (30 C) 1,8-Diamino-3-oxa-6-thiooctane 2,3-Diaminopropanoic acid (  0.1) 2,3-Diaminopropanoic acid, methyl ester (  0.1)

pK2

pK3

pK4

9.17(SH) 8.99(SH) 7.09 2.1(1) 3.21 12.24(0) 4.36(0) 4.31(0) 4.39(0) 12.15(0)

4.59 3.21 3.8(1) 6.58 12.52 2.5(1) 4.17(1)

5.59 7.92

2.96 7.42 9.29(1) 7.78(0) 6.44(3) 5.30

4.04

8.47 8.02(0) 6.01

8.71(1) 6.87

6.17(1) 6.04(1) 6.62(1)

13.2(sugar)

10.3

8.14(OH)

8.56(2)

10.38(1)

6.01(4) 1.85(2) 8.84(2) 8.43(2)

7.26(3) 8.24(1) 9.64(1) 9.31(1)

9.49(2) 10.40(0)

10.23(1)

1.84(2) 8.60(2) 8.54(2) 1.33(2)

2.64(1) 9.57(1) 9.46(1) 6.674(1)

9.23(0)

9.89(1)

4.412(1)

8.250(0)

9.623(0)

OH O OH

OH

HO

O

HO O

N

Cytidine

H

N

H

NH2

HO

H

H

Deoxycholic acid

8.22

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 1,3-Diamino-2-propanol (20 C) 2,5-Diaminopyridine (20 C) 1,4-Diazabicyclo[2.2.2]octane Dibenzylamine Dibenzylsuccinic acid (20 C) Dibromoacetic acid 3,5-Dibromoaniline 3,5-Dibromophenol 2,2-Dibromopropanoic acid 2,3-Dibromopropanoic acid rac-2,3-Dibromosuccinic acid (20 C) meso-2,3-Dibromosuccinic acid (20 C) 3,5-Dibromo-p-L-tyrosine Dibutylamine Di-sec-butylamine 2,6-Di-tert-butylpyridine rac-2,3-Di-tert-butylsuccinic acid (  0.1) 1,12-Dicarboxydodecaborane Dichloroacetic acid Dichloroacetylacetic acid 3,5-Dichloroaniline 1,3-Dichloro-2,5-dihydroxybenzene (  0.65) 2,5-Dichloro-3,6-dihydroxyp-benzoquinone Dichloromethylphosphonic acid 2,4-Dichloro-6-nitroaniline 2,5-Dichloro-4-nitroaniline 2,6-Dichloro-4-nitroaniline 2,3-Dichlorophenol 2,4-Dichlorophenol 2,6-Dichlorophenol 3,4-Dichlorophenol 3,5-Dichlorophenol 2,4-Dichlorophenoxyacetic acid (2,4-D) 4,6-Dichlorophenoxy-2-methylacetic acid 3,6-Dichlorophthalic acid 2,2-Dichloropropanoic acid 2,3-Dichloropropanoic acid rac-2,3-Dichlorosuccinic acid (20 C) meso-2,3-Dichlorosuccinic acid 3,5-Dichloro-p-tyrosine 2-Dicyanoethylamine 2,2-Dicyanopropanoic acid

pK1

pK2

7.93(2) 2.13(2) 2.90(2) 8.52(1) 3.96 1.39 2.35(1) 8.056 1.48 2.33

9.69(1) 6.48(1) 8.60(1)

1.43

2.24

1.51 2.17(1) 11.25(1) 10.91(1) 3.58(1)

2.71 6.45(0)

3.58 9.07 1.26 2.11 2.37(1)

10.2 10.23

7.30

9.99

1.09 1.14 3.00(1) 1.74(1) 3.31(1) 7.44 7.85 6.78 8.630 8.179

2.42 5.61

pK3

6.66

7.60(1)

2.64 3.13 1.46 2.06 2.85 1.43 1.49 2.12 5.14(1) 2.8

2.81 2.97 6.47

7.62

pK4

8.23

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Dicyclohexylamine Dicyclopentylamine Didodecylamine Diethanolamine Di(ethoxyethyl)amine 3,5-Diethoxyphenol 3-(Diethoxyphosphinyl)benzoic acid 4-(Diethoxyphosphinyl)benzoic acid 3-(Diethoxyphosphinyl)phenol 4-(Diethoxyphosphinyl)phenol Diethylamine 2-(Diethylamino)ethyl4-aminobenzoate -(Diethylamino)toluene N,N-Diethylaniline 5,5-Diethylbarbituric acid (veronal) N,N-Diethylbenzylamine Diethylbiguanide (30 C) Diethylenetriamine Diethylenetriaminepentaacetic acid (pK5  10.58) N,N-Diethylethylenediamine 2,2-Diethylglutaric acid N,N-Diethylglycine Diethylglycolic acid (18 C) Diethylmalonic acid Diethylmethylamine rac-2,3-Diethylsuccinic acid meso-2,3-Diethylsuccinic acid N,N-Diethyl-o-toluidine Difluoroacetic acid 3,3-Difluoroacrylic acid Diglycolic acid Diguanidine Dihexylamine Dihydroarecaidine Dihydroarecaidine, methyl ester Dihydrocodeine Dihydroergonovine -Dihydrolysergic acid

pK2

pK3

pK4

11.25(1) 10.93(1) 10.99() 8.88(1) 8.47(1) 9.370 3.65 3.60 8.66 8.28 10.8(1) 8.85(1) 9.44(1) 6.56(1) 8.020(0) 9.48(1) 2.53(1) 4.42(3)

11.68(0) 9.21(2)

1.80(0) 7.70(2) 3.62 2.04(1) 3.804 2.151 10.43(1) 3.63 3.54 7.18(1) 1.33 3.17 2.96 12.8 11.0(1) 9.70 8.39 8.75(1) 7.38(1) 3.57

2.55(1) 10.46(1) 7.12 10.47(0) 7.417 6.46 6.59

8.45

O MeO

N

Dihydroarecaidine

10.02(1) 4.33(2)

8.60(3)

8.24

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance -Dihydrolysergic acid -Dihydrolysergol -Dihydrolysergol Dihydromorphine 3,4-Dihydroxyalanine 1,2-Dihydroxyanthraquinone3-sulfonic acid (alizarin-3-sulfonic acid) 3,4-Dihydroxybenzaldehyde 1,2-Dihydroxybenzene (pyrocatechol) (  0.1) 1,3-Dihydroxybenzene (resorcinol) 1,4-Dihydroxybenzene (hydroquinone) 4,5-Dihydroxybenzene-1,3-disulfonic acid 2,3-Dihydroxybenzoic acid (30 C) 2,4-Dihydroxybenzoic acid (-resorcyclic acid) 2,5-Dihydroxybenzoic acid 2,6-Dihydroxybenzoic acid 3,4-Dihydroxybenzoic acid 3,5-Dihydroxybenzoic acid 2,5-Dihydroxy-p-benzoquinone 3,4-Dihydroxy-3-cyclobutene1,2-dione 2,3-Dihydroxy-2-cyclopenten-1-one (20 C) 1,4-Dihydroxy-2,6-dinitrobenzene Di(2,2-hydroxyethyl)amine N,N-Di(2-hydroxyethyl)glycine Dihydroxymaleic acid Dihydroxymalic acid 1,3-Dihydroxy-2-methylbenzene (  0.65) 2,2-Di(hydroxymethyl)3-hydroxypropanoic acid 2,4-Dihydroxy-5-methylpyrimidine 2,4-Dihydroxy-6-methylpyrimidine 1,4-Dihydroxynaphthalene (26 C,   0.65) 1,2-Dihydroxy-3-nitrobenzene 1,2-Dihydroxy-4-nitrobenzene (  0.1) 2,4-Dihydroxy-1-phenylazobenzene (  0.1) 2,4-Dihydroxyoxazolidine 2,4-Dihydroxypteridine 2,6-Dihydroxypurine

pK1 3.60 8.30 8.23 9.35 2.32(1)

pK2

pK3

pK4

8.71

8.68(0)

9.87(1)

5.54(1)

11.01(2)

7.55 9.356(0) 9.44(0)

12.98(1) 12.32(1)

9.91(0)

12.04(1)

2.98

10.14

3.29 2.97 1.30 4.48 4.04 2.71

8.98 10.50

0.541

3.480

7.66(2)

4.72 4.42 8.8(1) 8.333 1.10 1.92 10.05

8.67 5.18

9.14

11.64

4.460 9.90 9.52 9.37 6.68

10.93

6.701 11.98 6.11(1)  1.3 7.53(0)

7.92 11.84(1)

11.74

12.6(3)

8.25

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2,4-Dihydroxypyridine (20 C) Dihydroxytartaric acid 1,4-Dihydroxy-2,3,5,6tetramethylbenzene (  0.65) 3,5-Diiodoaniline 2,5-Diiodohistamine 2,5-Diiodohistidine (  0.1) 3,5-Diiodophenol 3,5-Diiodotyrosine Diisopropylmalonic acid Dilactic acid threo-1,4-Dimercapto-2,3-butanediol meso-2,3-Dimercaptosuccinic acid 3,5-Dimethoxyaniline 2,6-Dimethoxybenzoic acid 1,10-Dimethoxy-3,8-dimethyl4,7-phenanthroline Di(2-methoxyethyl)amine 3,5-Dimethoxyphenol (3,4-Dimethoxy)phenylacetic acid Dimethylamine 4-Dimethylaminobenzaldehyde N,N-Dimethylaminocyclohexane 4-Dimethylamino-2,3-dimethyl1-phenyl-3-pyrazolin-5-one 4-Dimethylamino3,5-dimethylpyridine (20 C) 2-(Dimethylamino)ethanol 2-[2-(Dimethylamino)ethyl]pyridine 3-(Dimethylaminoethyl)pyridine 4-(Dimethylaminoethyl)pyridine 4-(Dimethylamino)-3-ethylpyridine (20 C) 4-(Dimethylamino)3-isopropylpyridine (20 C) 2-(Dimethylaminomethyl)pyridine 3-(Dimethylaminomethyl)pyridine 4-(Dimethylaminomethyl)pyridine 4-(Dimethylamino)-3-methylpyridine (20 C) 4-(Dimethylaminophenyl)phosphonic acid 3-(Dimethylamino)propanoic acid 4-(Dimethylamino)pyridine (20 C) N,N-Dimethylaniline 2,3-Dimethylaniline 2,4-Dimethylaniline 2,5-Dimethylaniline 2,6-Dimethylaniline

pK1

pK2

pK3

1.37(1) 1.95

6.45(0) 4.00

13(1)

11.25 2.37(1) 2.31(2) 2.72 8.103 2.117(1) 2.124 2.955 8.9 2.71 3.86(1) 3.44

12.70 8.20(1) 8.18

10.11(0) 9.76

6.479(0) 8.848

7.821(1)

3.48

8.89(SH)

7.21 9.51(1) 9.345 4.333 10.77(1) 1.647(1) 10.72(1) 4.18(1) 8.15(1) 9.26(1) 3.46(2) 4.30(2) 4.66(2)

8.75(1) 8.86(1) 8.70(1)

8.66(1) 8.27(1) 2.58(2) 3.17(2) 3.39(2)

8.12(1) 8.00(1) 7.66(1)

8.68(1) 2.0(1) 9.85(1) 6.09(1) 5.15(1) 4.70(1) 4.89(1) 4.53(1) 3.95(1)

4.2

7.35

pK4

10.79(SH)

8.26

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 3,4-Dimethylaniline 3,5-Dimethylaniline N,N-Dimethylaniline-4-phosphonic acid (17 C) Dimethylarsinic acid (cacodylic acid) 1,3-Dimethylbarbituric acid 2,3-Dimethylbenzoic acid 2,4-Dimethylbenzoic acid 2,5-Dimethylbenzoic acid 2,6-Dimethylbenzoic acid 3,4-Dimethylbenzoic 3,5-Dimethylbenzoic acid N,N-Dimethylbenzylamine Dimethylbiguanide 2,2-Dimethylbutanoic acid (18 C) Dimethylchlorotetracycline (  0.01) 2,6-Dimethyl-4-cyanophenol 3,5-Dimethyl-4-cyanophenol 5,5-Dimethyl-1,3-cyclohexanedione cis-3,3-Dimethyl-1,2cyclopropanedicarboxylic acid trans-3,3-Dimethyl1,2-cyclopropanedicarboxylic acid 3,5-Dimethyl-4-(dimethylamino)pyridine (20 C) 2,2-Dimethyl-1,3-dioxane-4,6-dione 1,1-Dimethylethanethiol (  0.1) N,N-DimethylethylenediamineN,N-diacetic acid N,N-DimethylethylenediamineN,N-diacetic acid N,N-DimethylethylenediamineN,N-diacetic acid N,N-Dimethylglycine Dimethylglycolic acid (18 C) N,N-Dimethylglycylglycine Dimethylglyoxime 5,5-Dimethyl-2,4-hexanedione 5,5-Dimethylhydantoin 2,4-Dimethyl-8-hydroxyquinoline 3,4-Dimethyl-8-hydroxyquinoline

pK1

pK2

pK3

5.17(1) 4.765(1) 2.0(1) 6.273 4.68(1) 3.771 4.217 3.990 3.362 4.41 4.302 9.02(1) 2.77(1) 5.03 3.30(1) 8.27 8.21 5.15

4.2

2.34

8.31

3.92

5.32

7.39

11.52

8.12(1) 5.1 11.22 6.63

9.53

7.40

10.16

5.99 2.146(1) 4.04 3.11(1) 10.60 10.01 9.19 6.20(1) 5.80(1)

9.97 9.940(0) 8.09(0)

10.60(0) 10.05(0) N

HO

N

Dimethylglyoxime

OH

pK4

8.27

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2,4-Dimethyl-8-hydroxyquinoline7-sulfonic acid Dimethylhydroxytetracycline 2,4-Dimethylimidazole Dimethylmalic acid 2,2-Dimethylmalonic acid 3,5-Dimethyl-4-(methylamino) pyridine (20 C) 2,3-Dimethylnaphthalene1-carboxylic acid 2,6-Dimethyl-4-nitrophenol 3,5-Dimethyl-4-nitrophenol ,-Dimethyloxaloacetic acid 3,3-Dimethylpentanedioic acid 2,2-Dimethylpentanoic acid 4,4-Dimethylpentanoic acid (18 C) 2,3-Dimethylphenol 2,4-Dimethylphenol 2,5-Dimethylphenol 2,6-Dimethylphenol 3,4-Dimethylphenol 3,5-Dimethylphenol 2,6-Dimethylphenoxyacetic acid Dimethylphenylsilylacetic acid N,N-Dimethylpiperazine 1,2-Dimethylpiperidine cis-2,6-Dimethylpiperidine 2,2-Dimethylpropanoic acid (pivalic acid) 2,2-Dimethylpropylphosphonic acid 2,4-Dimethylpyridine (2,4-lutidine) 2,5-Dimethylpyridine (2,5-lutidine) 2,6-Dimethylpyridine (2,6-lutidine) 3,4-Dimethylpyridine (3,4-lutidine) 3,5-Dimethylpyridine (3,5-lutidine) 2,4-Dimethylpyridine-1-oxide 2,5-Dimethylpyridine-1-oxide 2,6-Dimethylpyridine-1-oxide 3,4-Dimethylpyridine-1-oxide 3,5-Dimethylpyridine-1-oxide 2,3-Dimethylquinoline 2,6-Dimethylquinoline meso-2,2-Dimethylsuccinic acid rac-2,2-Dimethylsuccinic acid D-2,3-Dimethylsuccinic acid meso-2,3-Dimethylsuccinic acid rac-2,3-Dimethylsuccinic acid 2,4-Dimethylthiazole (  0.1)

pK1

3.20 (NH) 7.5 8.38(1) 3.17 3.17

pK2

10.14(OH) 9.4 6.06 6.06

9.96(1) 3.33 7.190 8.245 1.77 3.70 4.969 4.79 10.50 10.58 10.22 10.59 10.32 10.15 3.356 5.27 4.630(2) 10.22 11.07(1) 5.031 2.84 6.74(1) 6.43(1) 6.71(1) 6.47(1) 6.09(1) 1.627(1) 1.208(1) 1.366(1) 1.493(1) 1.181(1) 4.94(1) 5.46(1) 3.77 3.93 3.82 3.67 3.94 3.98

4.62 6.34

8.539(1)

8.65

5.936 6.20 5.93 5.30 6.20

pK3

pK4

8.28

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

2,5-Dimethylthiazole (  0.1) 4,5-Dimethylthiazole (  0.1) N,N-Dimethyl-o-toluidine N,N-Dimethyl-p-toluidine 2,4-Dinitroaniline 2,6-Dinitroaniline 3,5-Dinitroaniline 2,3-Dinitrobenzoic acid 2,4-Dinitrobenzoic acid 2,5-Dinitrobenzoic acid 2,6-Dinitrobenzoic acid 3,4-Dinitrobenzoic acid 3,5-Dinitrobenzoic acid 1,1-Dinitrobutane (20 C) 1,1-Dinitrodecane 1,1-Dinitroethane (20 C) Dinitromethane (20 C) 1,1-Dinitropentane 2,4-Dinitrophenol 2,5-Dinitrophenol 2,6-Dinitrophenol 3,4-Dinitrophenol 3,5-Dinitrophenol 2,4-Dinitrophenylacetic acid 1,1-Dinitropropane (20 C) 2,6-Dioxo-1,2,3,6-tetrahydro4-pyrimidinecarboxylic acid (orotic acid) Diphenylacetic acid Diphenylamine 2,2-Diphenylglutaric acid (20 C) 1,3-Diphenylguanidine 2,2-Diphenylheptanedioic acid (20 C) 2,2-Diphenylhexanedioic acid (20 C) 3,3-Diphenylhexanedioic acid Diphenylhydroxyacetic acid (35 C) Diphenylketimine 2,2-Diphenylnonanedioic acid (20 C) O

pK2

3.91 3.73 5.86(1) 7.24(1) 4.25(1) 5.23(1) 0.229(1) 1.85 1.43 1.62 1.14 2.82 2.85 5.90 3.60 5.21 3.60 5.337 4.08 5.216 3.713 5.424 6.732 3.50 5.5

1.8(1) 3.939 0.9(1) 3.91 10.12 4.28 4.17 4.22 3.05 6.82 4.33

9.55(0)

5.38

5.39 5.40 5.19

5.38

OH O OH

2,2-Diphenylglutaric acid

NH

Diphenylketimine

pK3

pK4

8.29

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

meso-2,2-Diphenylsuccinic acid rac-2,2-Diphenylsuccinic acid 2,2-Diphenylsuccinic acid, 1-methyl ester (20 C) 2,2-Diphenylsuccinic acid, 4-methyl ester (20 C) Diphenylthiocarbazone Dipropylamine Dipropylenetriamine 2,2-Dipropylglutaric acid Dipropylmalonic acid 2,2-Dipyridyl 2,3-Dipyridyl (20 C) 2,4-Dipyridyl (20 C) 3,3-Dipyridyl (20 C,   0.2) 3,4-Dipyridyl (20 C,   0.2) 4,4-Dipyridyl Dithiodiacetic acid (18 C) 1,4-Dithioerythritol Dithiooxamide (rubeanic acid) Dulcitol

3.48 3.58

Ecgonine Emetine Epinephrine enantiomorph Epinephrine, pseudo Ergometrinine Ergonovine Eriochrome Black T 1,2-Ethanediamine Ethane-1,2-diamino-N,N-dimethylN,N-diacetic acid (20 C) 1,2-Ethanedithiol Ethanethiol (  0.015) Ethoxyacetic acid (18 C) 2-Ethoxyaniline (o-phenetidine) 3-Ethoxyaniline 4-Ethoxyaniline 2-Ethoxybenzoic acid (20 C) 3-Ethoxybenzoic acid (20 C) 4-Ethoxybenzoic acid (20 C) Ethoxycarbonylethylamine 2-Ethoxyethanethiol 2-Ethoxyethylamine 2-Ethoxyphenol 3-Ethoxyphenol (4-Ethoxyphenyl)phosphonic acid 4-Ethoxypyridine Ethyl acetoacetate 3-Ethylacrylic acid

10.91 7.36(1) 9.39(1) 9.53(1) 7.32(1) 6.73(1) 6.3 6.85(2)

pK2

pK3

9.56(2) 7.31 7.51 4.352(1) 4.42(1) 4.77(1) 4.60(1) 4.85(1) 4.82(1) 4.201

10.65(1)

4.47 3.900 4.50 10.91(1) 7.72(3) 3.688 2.04 0.52(2) 1.52(2) 1.19(2) 3.0(2) 3.0(2) 3.17(2) 3.075 9.5 10.89 13.46

6.047(0) 8.96 10.61 3.65 4.47(1) 4.17(1) 5.25(1) 4.21 4.17 4.80 9.13(1) 9.38 6.26(1) 10.109 9.655 2.06 6.67(1) 10.68 4.695

15

8.23(0)

11.55 9.92(1) 10.068(1) 10.54

7.28

pK4

8.30

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

N-Ethylalanine Ethylamine (3-Ethylamino)phenylphosphonic acid N-Ethylaniline 2-Ethylaniline 3-Ethylaniline 4-Ethylaniline Ethylarsonic acid (18 C) Ethylbarbituric acid 2-Ethylbenzimidazole (  0.16) 2-Ethylbenzoic acid 4-Ethylbenzoic acid Ethylbiguanide 2-Ethylbutanoic acid (20 C) S-Ethyl-L-cysteine (  0.1) Ethylenebiguanide (30 C) Ethylenebis(thioacetic acid) (18 C) Ethylenediamine-N,N-diacetic acid Ethylenediamine-N,N-dimethylN,N-diacetic acid Ethylenediamine-N,N-dipropanoic acid (30 C) Ethylenediamine-N,N,N,Ntetraacetic acid (  0.1) Ethylenediamine-N,N,N,Ntetrapropanoic acid (30 C) Ethylene glycol Ethyleneimine cis-Ethylene oxide dicarboxylic acid trans-Ethylene oxide dicarboxylic acid N-Ethylethylenediamine N-Ethylglycine (  0.1) 3-Ethylglutaric acid Ethyl hydroperoxide Ethyl hydrogen malonate 3-Ethyl-2-hydroxypyridine Ethylmalonic acid

pK2

2.22(1) 10.63(1)

10.22(0)

1.1(1) 5.11(1) 4.42(1) 4.70(1) 5.00(1) 3.89 3.69(1) 6.27(1) 3.79 4.35 2.09(1) 4.710 2.03(1) 1.74 3.382(0) 6.42

4.90(0)

8.60(0) 2.88 4.352(1) 9.46

6.047

10.068

6.87

9.60

1.99

pK3

7.24(1)

8.35

11.47(0)

11.34

11.76

2.67

6.16

10.26

3.00 14.22 8.04(1) 1.93

3.43

6.77

9.60

1.93 7.63(2) 2.34(1) 4.28 11.80 3.55 5.00(1) 2.90(0)

3.25 10.56(1) 10.23(0) 5.33

3.92

5.55(1) OH O

NH

NH

O

H2N

N H

pK4

N

Ethylenebiguanide

OH

3-Ethylglutaric acid

8.31

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

N-Ethyl mercaptoacetamide Ethyl 2-mercaptoacetate Ethyl 3-mercaptopropanoate 3-Ethyl-4-(methylamino)pyridine (20 C) 5-Ethyl-5-(1-methylbutyl)barbituric acid Ethyl methyl ketoxime Ethylmethylmalonic acid 1-Ethyl-2-methylpiperidine 3-Ethyl-6-methylpyridine (20 C) 3-Ethyl-4-methylpyridine-1-oxide 5-Ethyl-2-methylpyridine-1-oxide 1-Ethyl-2-methyl-2-pyrroline Ethylmorphine (15 C) Ethyl nitroacetate 3-Ethylpentane-2,4-dione 2-Ethylpentanoic acid (18 C) 5-Ethyl-5-pentylbarbituric acid 2-Ethylphenol 3-Ethylphenol 4-Ethylphenol 4-Ethylphenylacetic acid 5-Ethyl-5-phenylbarbituric acid Ethylphosphinic acid Ethylphosphonic acid 1-Ethylpiperidine (  0.01) 2,2-Ethylpropylglutaric acid Ethylpropylmalonic acid 2-Ethylpyridine 3-Ethylpyridine (20 C) 4-Ethylpyridine Ethyl 3-pyridinecarboxylate Ethyl 4-pyridinecarboxylate 2-Ethylpyridine-1-oxide 3-Ethylpyridine-1-oxide Ethylpyrrolidine 2-Ethyl-2-pyrroline Ethylsuccinic acid S-Ethylthioacetic acid N-Ethyl-o-toluidine N-Ethylveratramine -Eucaine

8.11(0) 12.45 2.86(0) 10.66(1) 6.51(1) 1.534(1) 1.288(1) 11.84(1) 8.08 5.85 11.34 4.71 7.960 10.2 10.07 10.0 4.373 7.445 3.29 2.43 10.45(1) 3.511 3.14 5.89(1) 5.80(1) 5.87(1) 3.35(1) 3.45(1) 1.19(1) 0.965(1) 10.43(1) 7.87(1) 4.08(0) 5.06 4.92(1) 7.40(1) 9.35(1)

Fluoroacetic acid 2-Fluoroacrylic acid 2-Fluoroaniline 3-Fluoroaniline 4-Fluoroaniline 2-Fluorobenzoic acid

2.586 2.55 3.20(1) 3.58(1) 4.65(1) 3.27

pK2

8.14(SH) 7.95(SH) 9.48(SH) 9.90(1)

6.41(1)

8.05

7.43

pK3

pK4

8.32

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

3-Fluorobenzoic acid 4-Fluorobenzoic acid Fluoromandelic acid 2-Fluorophenol 3-Fluorophenol 4-Fluorophenol 2-Fluorophenoxyacetic acid 3-Fluorophenoxyacetic acid 4-Fluorophenoxyacetic acid 4-Fluorophenylacetic acid 2-Fluorophenylalanine 3-Fluorophenylalanine 4-Fluorophenylalanine 2-Fluorophenylphosphonic acid 3-Fluorophenylselenic acid 4-Fluorophenylselenic acid 2-Fluoropyridine 3-Fluoropyridine 5-Fluorouracil Folic acid (pteroylglutamic acid) Formic acid N-Formylglycine 2-Formyl-3-hydroxypyridine (20 C) 4-Formyl-3-hydroxypyridine 2-Formyl-3-methoxypyridine (20 C) Formyl-3-methoxypyridine (20 C) D-()-Fructose Fumaric acid 2-Furancarboxylic acid (2-furoic acid)

pK2

3.865 4.14 4.244 8.73 9.29 9.89 3.08 3.08 3.13 4.25 2.14(1) 2.10(1) 2.13(1) 1.64 4.34 4.50 0.44(1) 2.97(1) 8.00(0) 8.26 3.751 3.43 3.40(1) 4.05(1) 3.89(1) 4.45(1) 12.03 3.10

12.35

Galactose-1-phosphoric acid Glucoascorbic acid D-Gluconic acid -D-()-Glucose -D-Glucose-1-phosphate trans-Glutaconic acid D-()-Glutamic acid L-Glutamic acid Glutamic acid, 1-ethyl ester

1.00 4.26 3.86 12.28 1.11(0) 3.77 2.162(1) 2.13(1) 3.85(1)

O

N H

O

5-Fluorouracil

9.01(0) 8.98(0) 9.05(0) 6.80

ca 13(1)

6.95(OH) 6.77(OH) 12.95 11.7 4.60

6.17 11.58

6.504(1) 5.08 4.272(0) 4.31(0) 7.84(0)

9.358(1) 9.76(1)

OH HO

HO

OHO

HO

NH

OH O

HO

O HO

pK4

3.164

D-()-Galactose

F

pK3

OH

D-(+)-Galactose

OH

HO

OHO D-Gluconic

OH acid

OH

OH


-D-(+)-Glucose

8.33

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Glutamic acid, 5-ethyl ester L-Glutamine (  0.2) Glutaric acid Glutaric acid monoamide Glutarimide Glutathione DL-Glyceric acid Glycerol Glyceryl-1-phosphoric acid Glyceryl-2-phosphoric acid Glycine Glycine amide Glycine, ethyl ester Glycine hydroxamic acid Glycine, methyl ester Glycine-O-phenylphosphorylserine Glycolic acid N-Glycyl--alanine Glycylalanylalanine N-Glycylasparagine Glycylaspartic acid Glycyl-DL-glutamine (18 C) N-Glycylglycine Glycylglycylcysteine (35 C) Glycylglycylglycine Glycyl-L-histidine (  0.16) Glycylisoleucine N-Glycyl-L-leucine Glycyl-O-phosphorylserine L-Glycylproline (  0.1) N-Glycylsarcosine (  0.1) N-Glycylserine Glycylserylglycine Glycyltyrosine Glycylvaline Glyoxaline Glyoxylic acid Guanidineacetic acid

pK2

2.15(1) 2.15(1) 3.77 4.600(0) 11.43 2.12(1) 3.64 14.15

pK3

pK4

9.19(0) 9.00(0) 6.08

3.53(0)

8.66

9.12

6.656(1) 6.650(1) 9.70(0)

1.335(0) 2.351(1) 8.03(1) 7.66(1) 7.10 7.59(1) 2.96 3.831 3.15(1) 3.38(1) 2.942 2.81(1) 2.88(1) 3.126(1) 2.71 3.225(1) 6.79 8.00 3.180(1) 2.90 2.81(1) 2.98(1) 2.98(1) 3.32 2.93 3.15 7.03(1) 3.30(0) 2.82(1)

9.10 8.07 8.33(0) 8.10(0) 4.45(0) 8.33(0) 8.252(0) 2.71 8.090(0) 8.20

8.60(1)

7.94

8.327(0) 6.02 8.65(0) 8.55(0) 8.38(0) 7.99 8.45 8.18

7.94

8.43

10.49

O O

HO

NH2 O NH

HO

O

HN

O

O O

O

S

NH

OH HN

OH

HO

S

O H2N

HO

Glutaric acid Glutathione

O

8.34

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance Guanine Guanine deoxyriboside3-phosphoric acid Guanosine Guanosine-5-diphosphoric acid (  0.1; pK5  59.6) Guanosine-3-phosphoric acid Guanosine-5-phosphoric acid (  0.1) Guanosine-5-triphosphoric acid [  0.1; pK5  7.10(3); pK6  9.3(4)] Guanylurea Harmine (20 C) Heptafluorobutanoic acid 4,4,5,5,6,6,6-Heptafluorohexanoic acid 4,4,5,5,6,6,6-Heptafluoro-2-hexenoic acid Heptanedioic acid (pimelic acid) 2,4-Heptanedione Heptanoic acid Heroin 2,4-Hexadienoic acid (sorbic acid) 1,1,1,3,3,3-Hexafluoro2,2-propanediol 1,1,1,3,3,3-Hexafluoro-2-propanol Hexahydroazepine Hexamethyldisilazine 1,2,3,8,9,10-Hexamethyl4,7-phenanthroline (20 C) 1,6-Hexanediamine 1,6-Hexanedioic acid 2,4-Hexanedione 2,2,4,4,6,6-Hexanitrodiphenylamine Hexanoic acid (20 C) trans-2-Hexenoic acid trans-3-Hexenoic acid 3-Hexen-4-oic acid 4-Hexen-5-oic acid Hexylamine Hexylarsonic acid Hexylphosphonic acid DL-Histidine

pK1

pK2

pK3

pK4

3.3(1)

9.2

12.3

2.9 9.25(0)

6.4 12.33 (OH)

9.7

1.9(1)

0.7

2.3

2.9 5.92

6.3 9.38

2.4

6.1

9.4

3.0(2) 1.80

8.20

7.61(1) 0.17 4.18 3.23 4.484 8.43(keto): 9.15(enol) 4.893 7.6(1)

5.424

4.77 8.801 9.42 11.07 7.55 7.26 9.830(2) 4.418 8.49 (enol); 9.32 (keto) 5.42 (1) 4.849 4.74 4.72 4.58 4.74 10.64(1) 4.16 2.6 1.82(2)

10.930(1) 5.412

9.19 7.9 6.00(1)

9.16(0)

8.35

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Histidine amide (  0.2) Histidine, methyl ester (  0.1) Histidylglycine Histidylhistidine (  0.16) DL-Homatropine DL-Homocysteine Homocysteine (  0.1) Hydantoin Hydrastine Hydrazine-N,N-diacetic acid Hydrazine-N,N-diacetic acid 4-Hydrazinocarbonylpyridine (20 C) N-Hydroxyacetamide 2-Hydroxyacetophenone 3-Hydroxyacetophenone 4-Hydroxyacetophenone 1-Hydroxyacridine (15 C) 2-Hydroxyacridine (15 C) 3-Hydroxyacridine (15 C) -Hydroxyasparagine -Hydroxyasparagine Hydroxyaspartic acid 2-Hydroxybenzaldehyde (salicylaldehyde) 3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde 2-Hydroxybenzaldehyde oxime 2-Hydroxybenzamide 2-Hydroxybenzenemethanol (2-hydroxybenzyl alcohol) 3-Hydroxybenzenemethanol 4-Hydroxybenzenemethanol 4-Hydroxybenzenesulfonic acid 2-Hydroxybenzohydroxamic acid 2-Hydroxybenzoic acid (salicylic acid) 3-Hydroxybenzoic acid 4-Hydroxybenzoic acid 4-Hydroxybenzonitrile 2-Hydroxy-5-bromobenzoic acid 2-Hydroxybutanoic acid (30 C)

pK2

5.78(2) 5.01(2) 2.40(2) 5.40(2) 9.7(1) 2.222(1) 1.593(2) 9.12 6.23(1)  0.1 2.40 1.82 9.40 9.90 9.19 8.05 5.72 5.62 5.30 2.28(1) 2.09(1) 1.91(1) 8.34 9.00 7.620 1.37(1) 8.36

7.64(1) 7.23(1) 5.80(1) 6.80(1)

7.82(0) 7.95(0)

8.87 2.523(1)

10.86 8.676(0)

2.8 3.12 3.52

3.8 7.32 10.79

7.20(0) 8.29(0) 3.51(0)

9.11(1)

9.18

12.11

9.92 9.83 9.82 9.055(1) 5.19 2.98 4.076 4.582 7.95 2.61 3.65

12.38 9.85 9.23

NH O N H Hydantoin

pK3

O

pK4

9.413(1)

8.36

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance L-3-Hydroxybutanoic acid (30 C)

4-Hydroxybutanoic acid (30 C) 2-Hydroxy-5-chlorobenzoic acid trans-2-Hydroxycinnamic acid trans-3-Hydroxycinnamic acid 10-Hydroxycodeine cis-2-Hydroxycyclohexane1-carboxylic acid trans-2-Hydroxycyclohexane1-carboxylic acid cis-3-Hydroxycyclohexane1-carboxylic acid trans-3-Hydroxycyclohexane1-carboxylic acid cis-4-Hydroxycyclohexane1-carboxylic acid trans-4-Hydroxycyclohexane1-carboxylic acid 1-Hydroxy-2,4dihydroxymethylbenzene N-(Hydroxyethyl)biguanide N-(2-Hydroxyethyl)ethylenediamine N-(2-Hydroxyethyl)ethylenediamine-N,N,N-triacetic acid N-(2-Hydroxyethyl)iminodiacetic acid (  0.1) N-(2-Hydroxyethyl)piperazine-Nethanesulfonic acid (20 C) 4-(2-Hydroxyethyl)-1-piperazinepropanesulfonic acid (20 C) 2-Hydroxyethyltrimethylamine L--Hydroxyglutamic acid 1-Hydroxy-4-hydroxymethylbenzene 5-Hydroxy-2-(hydroxymethyl)4H-pyran-4-one 3-Hydroxy-2-hydroxymethylpyridine (20 C,   0.2) 3-Hydroxy-4-hydroxymethylpyridine (20 C,   0.2) 8-Hydroxy-7-iodoquinoline5-sulfonic acid Hydroxylysine (38 C,   0.1) 2-Hydroxy-3-methoxybenzaldehyde 3-Hydroxy-4-methoxybenzaldehyde (isovanillin) 4-Hydroxy-3-methoxybenzaldehyde (vanillin) 4-Hydroxy-3-methoxybenzoic acid 1-Hydroxy-2-methoxybenzylamine

pK1

pK2

pK3

4.41 4.71 2.63 4.614 4.40 7.12 4.796 4.682 4.602 4.815 4.836 4.687 9.79 2.8(2) 7.21(2)

11.53(1) 10.12(1)

2.39

5.37

2.2

8.65

9.93

7.55 8.00 8.94(1) 2.09 9.84

4.18

7.90

8.03

5.00(1)

9.07(OH)

5.00(1)

8.95(OH)

2.51(0) 2.13(2) 7.912

7.417(1) 8.62(1)

8.889 7.396 4.355 8.70(1)

10.52(0)

9.20

9.67(0)

pK4

8.37

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2-Hydroxy-1-methoxybenzylamine 3-Hydroxy-2-methoxybenzylamine 2-Hydroxymethyl-2-benzeneacetic acid (2-Hydroxy-5-methylbenzene)methanol 2-Hydroxy-3-methylbenzoic acid 2-Hydroxy-4-methylbenzoic acid 2-Hydroxy-5-methylbenzoic acid 2-Hydroxy-6-methylbenzoic acid 2-Hydroxy-2-methylbutanoic acid (18 C) 3-Hydroxy-2-methylbutanoic acid (18 C) 4-Hydroxy-4-methylpentanoic acid (18 C) 1-Hydroxymethylphenol Hydroxymethylphosphoric acid 2-Hydroxy-2-methylpropanoic acid (  0.1) 2-Hydroxy-4-methylpyridine 8-Hydroxy-2-methylquinoline 8-Hydroxy-4-methylquinoline 8-Hydroxy-2-methylquinoline5-sulfonic acid 8-Hydroxy-4-methylquinoline7-sulfonic acid 8-Hydroxy-6-methylquinoline5-sulfonic acid 2-Hydroxy-1-naphthoic acid (20 C) 2-Hydroxy-2-nitrobenzoic acid 2-Hydroxy-3-nitrobenzoic acid 2-Hydroxy-5-nitrobenzoic acid 2-Hydroxy-6-nitrobenzoic acid 2-Hydroxy-4-nitrophenylphosphonic acid 8-Hydroxy-7-nitroquinoline5-sulfonic acid 3-Hydroxy-4-nitrotoluene (  0.1) 4-Hydroxypentanoic acid (18 C) 4-Hydroxy-3-pentenoic acid 3-Hydroxyphenazine (15 C) 4-Hydroxyphenylarsonic acid 3-Hydroxyphenylboric acid 2-Hydroxy-2-phenylpropanoic acid 2-(2-Hydroxyphenyl)pyridine (20 C)

pK1 8.89(1) 8.94(1)

pK2

pK3

10.52(0) 10.42(0)

4.12 10.15 2.99 3.17 4.08 3.32 3.991 4.648 4.873 9.95 1.91

7.15

3.717 4.529(1) 5.55(1) 5.56(1)

10.31(0) 10.00(0)

4.80(0)

9.30(1)

4.78(0)

10.01(1)

4.20(0) 3.29 2.23 1.87 2.12 2.24

8.7(1) 9.68

1.22

5.39

1.94(0) 7.41 4.686 4.30 2.67 3.89

5.750(1)

8.55 3.532 4.19(1)

10.84

8.37

10.64

10.05 (phenol)

pK4

8.38

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

trans-4-Hydroxyproline Hydroxypropanedioic acid (tartronic acid) 2-Hydroxypropanoic acid 1-Hydroxy-2-propylbenzene 4-Hydroxypteridine 2-Hydroxypyridine 3-Hydroxypyridine 4-Hydroxypyridine 2-Hydroxypyridine-N-oxide 2-Hydroxypyrimidine 4-Hydroxypyrimidine 8-Hydroxyquinazoline 2-Hydroxyquinoline (20 C) 3-Hydroxyquinoline (20 C) 4-Hydroxyquinoline (20 C) 5-Hydroxyquinoline (20 C) 6-Hydroxyquinoline (20 C) 7-Hydroxyquinoline (20 C) 8-Hydroxyquinoline (20 C) 8-Hydroxyquinoline-5-sulfonic acid DL-Hydroxysuccinic acid (malic acid) L-Hydroxysuccinic acid Hydroxytetracycline 5-Hydroxy-1,2,3,4-tetrazole 4-Hydroxy-3-(2-thiazolyazo)toluene 2-Hydroxytoluene 3-Hydroxytoluene 4-Hydroxytoluene 4-Hydroxy-,,-trifluorotoluene 1-Hydroxy-2,4,6trihydroxymethylbenzene Hydroxyuracil Hydroxyvaline Hyoscyamine Hypoxanthene Hypoxanthine Imidazole Imidazolidinetrione (parabanic acid)

pK2

1.818(1)

9.662(0)

2.37 3.858 10.50 1.3(1) 1.25(1) 4.80(1) 3.23(1) 0.62(1) 2.24(1) 1.85(1) 3.41(1) 0.31(1) 4.30(1) 2.27(1) 5.20(1) 5.17(1) 5.48(1) 4.91(1) 4.092(1) 3.458 3.40 3.27(1) 3.32 8.36 10.33 10.10 10.276 8.675

4.74

7.89(0) 11.62(0) 8.72(0) 11.09(0) 5.97(0) 9.17(0) 8.59(0) 8.65(0) 11.74 8.06(0) 11.25(0) 8.54(0) 8.88(0) 8.85(0) 9.81(0) 8.776(0) 5.097 5.05 7.32(0)

9.56 8.64 2.55(1) 9.68(1) 1.79(1) 5.3

8.91(0)

6.993(1) 6.10

10.58(0)

NH

O

N H

N

Imidazole trans-4-Hydroxyproline

9.11(1)

9.77(0)

OH

HO

pK3

12.07(1)

pK4

8.39

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

4-(4-Imidazolyl)butanoic acid (  0.1) 2-(4-Imidazolyl)ethylamine 3-(4-Imidazolyl)propanoic acid (  0.16) 3,3-Iminobispropanoic acid 3,3-Iminobispropylamine (30 C) 2,2-Iminodiacetic acid (diglycine) (30 C,   0.1) 4-Indanol Indole-3-acetic acid Inosine Inosine-5-phosphoric acid Inosine-5-triphosphoric acid [pK5  7.68(4)] Iodoacetic acid 2-Iodoaniline 3-Iodoaniline 4-Iodoaniline 2-Iodobenzoic acid 3-Iodobenzoic acid 4-Iodobenzoic acid 5-Iodohistamine

pK2

4.26(1) 5.784(2)

7.62(0) 9.756(1)

3.96(1) 4.11(0) 8.02(2)

7.57(0) 9.61(1) 9.70(1)

2.54(0) 10.32 4.75 ca 1.5(1) 1.54(0)

9.12(1)

8.96(0) 6.66(1)

pK3

10.70(0)

12.36

2.2(2) 3.175 2.54(1) 3.58(1) 3.82(1) 2.86 3.86 4.00 4.06(2) (imidazole)

7-Iodo-8-hydroxyquinoline-5-sulfonic acid Iodomandelic acid Iodomethylphosphoric acid 2-Iodophenol 3-Iodophenol 4-Iodophenol 2-Iodophenoxyacetic acid 3-Iodophenoxyacetic acid 4-Iodophenoxyacetic acid 2-Iodophenylacetic acid 3-Iodophenylacetic acid 4-Iodophenylacetic acid 2-Iodophenylphosphoric acid 2-Iodopropanoic acid 3-Iodopropanoic acid 2-Iodopyridine

2.514 3.264 1.30 8.464 8.879 9.200 3.17 3.13 3.16 4.038 4.159 4.178 1.74 3.11 4.08 1.82(1) N

7.417 6.72

7.06

N O

HO

9.20(1) (NH3)

N

OH OH

N HO

Inosine

pK4

11.88(0) (imino)

6.92(3)

8.40

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

3-Iodopyridine 4-Iodopyridine (20 C) Isoasparagine Isobutylacetic acid (18 C) Isobutylamine Isochlorotetracycline Isocreatine Isoglutamine Isohistamine (  0.1) L-Isoleucine Isolysergic acid Isopilocarpine (15 C) 2-(Isopropoxy)benzoic acid (20 C) 3-(Isopropoxy)benzoic acid (20 C) 4-(Isopropoxy)benzoic acid (20 C) Isopropylamine N-Isopropylaniline 5-Isopropylbarbituric acid 2-Isopropylbenzene acid 4-Isopropylbenzoic acid N-Isopropylglycine (  0.1) Isopropylmalonic acid Isopropylmalonic acid mononitrile 3-Isopropyl-4-(methylamino)pyridine (20 C) 3-Isopropylpentanedioic acid 4-Isopropylphenylacetic acid Isopropylphosphinic acid Isopropylphosphonic acid 2-Isopropylpyridine 3-Isopropylpyridine (20 C) 4-Isopropylpyridine DL-Isoproterenol Isoquinoline Isoretronecanol L-Isoserine (  0.16) Isothiocyanatoacetic acid L-()-Lactic acid

3.25(1) 4.02(1) 2.97(1) 4.79 10.41(1) 3.1(1) 2.84(1) 3.81(1) 6.036(2) 2.318(1) 3.33(0) 7.18(1) 4.24 4.15 4.68 10.64(1) 5.50(1) 4.907(1) 3.64 4.36 2.36(1) 2.94 2.401

Leucine amide

pK3

pK4

8.02(0)

6.7(0)

8.3(1)

7.88(0) 9.274(1) 9.758(0) 8.46(NH)

10.06(0) 5.88

9.96(1) 4.30 4.391 3.56 2.66 5.83(1) 5.72(1) 6.02(1) 8.64(1) 5.40(1) 10.83 2.72(1) 6.62

5.51

8.44

9.25(0)

3.858 2.328(1) 7.80(1)

L-Leucine

H N

pK2

9.744(0)

OH N

OH

N OH

OH DL-Isoproterenol

H

Isoquinoline

Isoretronecanol

8.41

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Leucine, ethyl ester (  0.1) L-Leucyl-L-asparagine L-Leucyl-L-glutamine DL-Leucylglycine Leucylisoserine (20 C) D-Leucyl-L-tyrosine L-Leucyl-L-tyrosine Lysergic acid L-()-Lysine Lysine, methyl ester (  0.1) L-Lysyl-L-alanine L-Lysyl-D-alanine Lysylglutamic acid L-Lysyl-L-lysine (  0.1) L-Lysyl-D-lysine (  0.1) L-Lysyl-L-lysyl-L-lysine (  0.1) L-Lysyl-D-lysyl-L-lysine (  0.1) L-Lysyl-D-lysyl-lysine (  0.1) -D-Lyxose

7.57(1) 3.00(1) 2.99(1) 3.25(1) 3.188(1) 3.12(1) 3.46(1) 3.44(1) 2.18(2) 6.965(1) 3.22(1) 3.00(1) 2.93(2) 3.01(2) 2.85(2) 3.08(2) 2.91(2) 2.94(2) 12.11

Maleic acid Malonamic acid Malonic acid Malonitrile (cyanoacetic acid) Mandelic acid D-()-Mannose Mercaptoacetic acid (thioglycolic acid) 2-Mercaptobenzoic acid (20 C) 2-Mercaptobutanoic acid Mercaptodiacetic acid 2-Mercaptoethanesulfonic acid (20 C) 2-Mercaptoethanol 2-Mercaptoethylamine 2-Mercaptohistidine Mercapto-S-phenylacetic acid (  0.1) 2-Mercaptopropane (  0.1) 3-Mercapto-1,2-propanediol (  0.5) 2-Mercaptopropanoic acid 3-Mercaptopropanoic acid

1.910 3.641(0) 2.826 2.460 3.411 12.08

pK2

pK3

8.12(0) 8.11(0) 8.28(0) 8.207(0) 8.38(0) 7.84(0) 7.68(0) 8.95(1) 10.251(0) 7.62(0) 7.74(0) 4.47(1) 7.53(1) 7.53(1) 7.34(1) 7.29(1) 7.15(1)

10.35(1) 10.09(1) 10.53(0) 10.70(1) 10.63(1) 7.75(0) 10.05(0) 9.92(0) 9.80(0) 9.79(0) 9.60(0)

6.33 5.696

3.60(0) 4.05(0) 3.53(0) 3.32

10.56(SH)

4.29 9.5(1)

9.88 8.27(1) 1.84(1)

10.53(0) 8.47(0)

3.9 10.86 9.43 4.32(0)

11.4(SH)

10.20(SH) 10.84(SH) OH HO

HO

O OH O OH Mandelic acid

pK4

HO D-(+)-Mannose

OH

10.50(1) 10.01(1) 10.89(1) 10.54(1) 10.54(1) 10.38(1)

8.42

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2-Mercaptopyridine (20 C) 3-Mercaptopyridine (20 C) 4-Mercaptopyridine (20 C) 2-Mercaptoquinoline (20 C) 3-Mercaptoquinoline (20 C) 4-Mercaptoquinoline (20 C) Mercaptosuccinic acid Mesitylenic acid Mesoxaldialdehyde Methacrylic acid Methanethiol DL-Methionine 2-(N-Methoxyacetamido)pyridine 3-(N-Methoxyacetamido)pyridine 4-(N-Methoxyacetamido)pyridine Methoxyacetic acid 3-Methoxy-D--alanine 2-Methoxyaniline 3-Methoxyaniline 4-Methoxyaniline 2-Methoxybenzoic acid 3-Methoxybenzoic acid 4-Methoxybenzoic acid N,N-Methoxybenzylamine 2-Methoxycarbonylaniline 3-Methoxycarbonylaniline 4-Methoxycarbonylaniline Methoxycarbonylmethylamine 2-Methoxycarbonylpyridine 3-Methoxycarbonylpyridine 4-Methoxycarbonylpyridine trans-2-Methoxycinnamic acid trans-3-Methoxycinnamic acid trans-4-Methoxycinnamic acid 2-Methoxyethylamine 2-Methoxy-4-nitrophenylphosphonic acid 2-Methoxyphenol 3-Methoxyphenol 4-Methoxyphenol (2-Methoxy)phenoxyacetic acid

pK1

pK2

1.07(1) 2.26(1) 1.43(1) 1.44(1) 2.33(1) 0.77(1) 3.30(0) 4.32 3.60 4.66 10.70 2.13(1) 2.01(1) 3.52(1) 4.62(1) 3.570 2.037(1) 4.53(1) 4.20(1) 5.36(1) 4.09 4.08 4.49 9.68(1) 2.23(1) 3.64(1) 2.38(1) 7.66(1) 2.21(1) 3.13(1) 3.26(1) 4.462 4.376 4.539 9.45(1)

10.00(0) 7.03(0) 8.86(0) 10.21(0) 6.13(0) 8.83(0) 4.94(1)

1.53 9.99 9.652 10.20 3.231

6.96

9.28(0)

9.176(0)

HO O

Mesitylenic acid

pK3

10.94(SH)

pK4

8.43

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance (3-Methoxy)phenoxyacetic acid (4-Methoxy)phenoxyacetic acid 4-Methoxyphenylacetic acid (4-Methoxyphenyl)phosphinic acid (17 C) (2-Methoxyphenyl)phosphonic acid (4-Methoxyphenyl)phosphonic acid (17 C) 3-(2-Methoxyphenyl)propanoic acid 3-(3-Methoxyphenyl)propanoic acid 3-(4-Methoxyphenyl)propanoic acid 3-Methoxyphenylselenic acid 4-Methoxyphenylselenic acid 2-Methoxy-4-(2-propenyl)phenol 2-Methoxypyridine 3-Methoxypyridine 4-Methoxypyridine 4-Methoxy-2-(2-thiazoylazo)phenol 2-Methylacrylic acid (18 C) N-Methylalanine O-Methylallothreonine (  0.1) Methylamine 2-(N-Methylamino)benzoic acid 3-(N-Methylamino)benzoic acid 4-(N-Methylamino)benzoic acid Methylaminodiacetic acid (20 C) 2-(Methylamino)ethanol 2-(2-Methylaminoethyl)pyridine (30 C) 2-(Methylaminomethyl)-6-methylpyridine (  0.5) 2-(Methylaminomethyl)pyridine (30 C) 4-Methylamino-3-methylpyridine (20 C) (3-Methylamino)phenylphosphonic acid (4-Methylamino)phenylphosphonic acid 3-(Methylamino)pyridine (30 C) 4-(Methylamino)pyridine (20 C) 4-(Methylamino)-2,3,5,6-tetramethylpyridine (20 C) N-Methylaniline Methylarsonic acid (18 C) 1-Methylbarbituric acid 5-Methylbarbituric acid 2-(N-Methylbenzamido)pyridine

pK1

pK2

pK3

3.141 3.213 4.358 2.35 2.16 2.4 4.804 4.654 4.689 4.65 5.05 10.0 3.06(1) 4.91(1) 6.47(1) 7.83 4.66 2.22(1) 1.92(1) 10.62(1) 1.93(1)

2.146 9.88(1)

7.77 7.15

10.19(0) 8.90(0) 5.34(0) 5.10(0) 5.05 10.088

3.58(2)

9.65(1)

3.03(2)

9.15(1)

2.92(2)

8.82(1)

9.83(1) 1.1(1)

4.72(1)

7.30(1) 7.85(1)

8.70(1) 9.65(1) 10.06(1) 4.85(1) 3.41 4.35(1) 3.386(1) 1.44(1)

8.18

pK4

8.44

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 3-(N-Methylbenzamido)pyridine 4-(N-Methylbenzamido)pyridine 2-Methylbenzimidazole (  0.16) 2-Methylbenzoic acid (o-toluic acid) 3-Methylbenzoic acid 4-Methylbenzoic acid N-Methyl-1-benzoylecgonine Methylbiguanidine 2-Methyl-2-butanethiol 2-Methylbutanoic acid 3-Methylbutanoic acid (20 C) (E)-2-Methyl-2-butendioic acid (mesaconic acid) 3-Methyl-2-butenoic acid (E)-2-Methyl-2-butenoic acid (tiglic acid) (Z)-2-Methyl-2-butenoic acid (angelic acid) 4-Methylcarboxylphenol (E)-2-Methylcinnamic acid (E)-3-Methylcinnamic acid (E)-4-Methylcinnamic acid 1-Methylcyclohexane-1-carboxylic acid cis-2-Methylcyclohexane1-carboxylic acid trans-2-methylcyclohexane1-carboxylic acid cis-3-methylcyclohexane1-carboxylic acid trans-3-Methylcyclohexane1-carboxylic acid cis-4-Methylcyclohexane1-carboxylic acid trans-4-Methylcyclohexane1-carboxylic acid 2-Methylcyclohexyl-1,1-diacetic acid 3-Methylcyclohexyl-1,1-diacetic acid 4-Methylcyclohexyl-1,1,1-diacetic acid 3-Methylcyclopentyl-1,1-diacetic acid S-Methyl-L-cysteine N-Methylcytidine 5-Methylcytidine N-Methyl-2-deoxycytidine 5-Methyl-2-deoxycytidine 2-Methyl-3,5-dinitrobenzoic acid 5-Methyldipropylenetriamine (30 C) 2,2-Methylenebis(4-chlorophenol)

pK1 3.66(1) 4.68(1) 6.29(1) 3.90 4.269 4.362 8.65 3.00(2) 11.35 4.761 4.767 3.09 5.12

pK2

pK3

11.44(1)

4.75

4.96 4.30 8.47 4.500 4.442 4.564 5.13 5.03 5.73 4.88 5.02 5.04 4.89 3.53 3.49 3.49 3.79 8.97 3.88 4.21 3.97 4.33 2.97 6.32(3) 7.6

6.89 6.08 6.10 6.74

9.19(2) 11.5

10.33(1)

pK4

8.45

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2,2-Methylenebis(4,6-dichlorophenol) Methylenebis(thioacetic acid) (18 C) 3,3-(Methylenedithio)dialanine Methylenesuccinic acid N-Methylethylamine N-Methylethylenediamine -Methylglucoside 3-Methylglutaric acid N-Methylglycine (sarcosine) 5-Methyl-2,4-heptanedione 5-Methyl-2,4-hexanedione 5-Methyl-4-hexenoic acid 3-Methylhistamine 1-Methylhistidine 2-Methylhistidine (18 C) 2-Methyl-8-hydroxyquinoline (  0.005) 4-Methyl-8-hydroxyquinoline 1-Methylimidazole 4-Methylimidazole N-Methyliminodiacetic acid S-Methylisothiourea O-Methylisourea Methylmalonic acid 2-(N-Methylmethanesulfonamido)pyridine 3-(N-Methylmethanesulfonamido)pyridine 4-(N-Methylmethanesulfonamido)pyridine 2-Methyl-6-methylaminopyridine (20 C) 3-Methyl-4-methylaminopyridine (20 C) 4-Methyl-2,2(4-methylpyridyl)pyridine N-Methylmorpholine 2-Methyl-1-naphthoic acid N-Methyl-1-naphthylamine 2-Methyl-4-nitrobenzoic acid 2-Methyl-6-nitrobenzoic acid 1-Methyl-2-nitroterephthalic acid 4-Methyl-2-nitroterephthalic acid 3-Methylpentanedioic acid 3-Methylpentane-2,4-dione 2-Methylpentanoic acid

pK1

pK2

5.6 3.310 2.200(1) 3.85 4.23(1) 6.86(1) 13.71 4.24 2.12(1) 8.52(enol); 9.10(keto) 8.66(enol); 9.31(keto) 4.80 5.80(1) 1.69 1.7

10.56 4.345 8.16(0) 5.45

4.58(1) 4.67(1) 7.06(1) 7.55(1) 2.15 9.83(1) 9.72(1) 3.07

11.71(0) 11.62(0)

10.15(1) 5.41 10.20(0)

9.90(0) 6.48 7.2

10.09

5.87

1.73(1) 3.94(1) 5.14(1) 3.17(1)

8.84(0) 9.84(0)

5.32(1) 7.13(1) 3.11 3.70(1) 1.86 1.87 3.11 1.82 4.25 10.87 4.782

pK3

5.41

8.85 9.5

pK4

8.46

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 3-Methylpentanoic acid 4-Methylpentanoic acid cis-3-Methyl-2-pentenoic acid trans-3-Methyl-2-pentenoic acid 4-Methyl-2-pentenoic acid 4-Methyl-3-pentenoic acid 6-Methyl-1,10-phenanthroline (2-Methylphenoxy)acetic acid (3-Methylphenoxy)acetic acid (4-Methylphenoxy)acetic acid (2-Methylphenyl)acetic acid (18 C) (4-Methylphenyl)acetic acid 5-Methyl-5-phenylbarbituric acid 3-(2-Methylphenyl)propanoic acid 3-(3-Methylphenyl)propanoic acid 3-(4-Methylphenyl)propanoic acid 1-Methyl-2-phenylpyrrolidine 5-Methyl-1-phenyl-1,2,3-triazole4-carboxylic acid Methylphosphinic acid Methylphosphonic acid 3-Methyl-o-phthalic acid 4-Methyl-o-phthalic acid N-Methylpiperazine (  0.1) 2-Methylpiperazine N-Methylpiperidine 2-Methylpiperidine 3-Methylpiperidine 4-Methylpiperidine (  0.5) 2-Methyl-1,2-propanediamine 2-Methyl-2-propanethiol 2-Methylpropanoic acid 2-Methyl-2-propylamine 2-Methyl-2-propylglutaric acid 2-Methylpyridine 3-Methylpyridine 4-Methylpyridine Methyl 4-pyridinecarboxylate 6-Methylpyridine-2-carboxylic acid 2-Methylpyridine-1-oxide 3-Methylpyridine-1-oxide 4-Methylpyridine-1-oxide O-Methylpyridoxal (  0.16) Methyl-2-pyridyl ketoxime 1-Methyl-2-(3-pyridyl)pyrrolidine 1-Methylpyrrolidine 1-Methyl-3-pyrroline 5-Methylquinoline Methylsuccinic acid Methylsulfonylacetic acid

pK1

pK2

4.766 4.845 5.15 5.13 4.70 4.60 5.11(1) 3.227 3.203 3.215 4.35 4.370 8.011(0) 4.66 4.677 4.684 8.80 3.73 3.08 2.38 3.18 3.89 4.94(2) 5.62(2) 10.19(1) 10.95(1) 11.07(1) 11.23(1) 6.178(2) 11.2 4.853 10.682(1) 3.626 5.96(1) 5.68(1) 6.00(1) 3.26(1) 5.83 1.029(1) 10.921(1) 1.258(1) 4.74 9.97 3.41 10.46(1) 9.88(1) 4.62(1) 4.13 2.36

7.74

9.09(1) 9.60(1)

9.420(1)

7.94

5.64

pK3

pK4

8.47

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

3-Methylsulfonylaniline 4-Methylsulfonylaniline 3-Methylsulfonylbenzoic acid 4-Methylsulfonylbenzoic acid 4-Methylsulfonyl-3,5-dimethylphenol 3-Methylsulfonylphenol 4-Methylsulfonylphenol 1-Methyl-1,2,3,4-tetrahydro3-pyridinecarboxylic acid (arecaidine; isoguvacine) 5-Methyl-1,2,3,4-tetrazole 2-Methylthiazole (  0.1) 4-Methylthiazole (  0.1) 5-Methylthiazole (  0.1) Methylthioacetic acid 4-Methylthioaniline 2-Methylthioethylamine (30 C) Methylthioglycolic acid 3-(S-Methylthio)phenol 4-(S-Methylthio)phenol 2-Methylthiopyridine (20 C) 3-Methylthiopyridine (20 C) 4-Methylthiopyridine (20 C) 5-Methylthio-1,2,3,4-tetrazole O-Methylthreonine O-Methyltyrosine 1-Methylxanthine 3-Methylxanthine 7-Methylxanthine 9-Methylxanthine Morphine (20 C) Morpholine 2-(N-Morpholino)ethanesulfonic acid (MES) (20 C) 3-(N-Morpholino)-2-hydroxypropanesulfonic acid (37 C) 3-(N-Morpholino)propanesulfonic acid (20 C) Murexide Myosmine 1-Naphthalenecarboxylic acid (1-naphthoic acid) O

N H Morpholine

pK2

pK3

2.68(1) 1.48(1) 3.52 3.64 8.13 9.33 7.83

9.07 3.32 3.40(1) 3.16(1) 3.03(1) 3.72 4.40(1) 9.18(1) 7.68 9.53 9.53 3.59(1) 4.42(1) 5.94(1) 4.00(1) 2.02(1) 2.21(1) 7.70 8.10 8.33 6.25 7.87(1) 8.492(1)

9.00(0) 9.35(0) 12.0 11.3 ca 13 9.85(0)

6.15 6.75 7.20 0.0 5.26

9.20

10.50

3.695 O

N

OH

N

Myosmine

1-Naphthalenecarboxylic acid

pK4

8.48

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 2-Naphthalenecarboxylic acid 1-Naphthol (20 C) 2-Naphthol (20 C) Naphthoquinone monoxime 1-Naphthylacetic acid 2-Naphthylacetic acid 1-Naphthylamine 2-Naphthylamine 1-Naphthylarsonic acid 1-Naphthylsulfonic acid Narceine (15 C) Narcotine Nicotine Nicotyrine Nitrilotriacetic acid (NTA) (20 C) Nitroacetic acid 2-Nitroaniline 3-Nitroaniline 4-Nitroaniline 2-Nitrobenzene-1,4-dicarboxylic acid 3-Nitrobenzene-1,2-dicarboxylic acid 4-Nitrobenzene-1,2-dicarboxylic acid 2-Nitrobenzoic acid 3-Nitrobenzoic acid 4-Nitrobenzoic acid trans-2-Nitrocinnamic acid trans-3-Nitrocinnamic acid trans-4-Nitrocinnamic acid Nitroethane 2-Nitrohydroquinone N-Nitroiminodiacetic acid 3-Nitromesitol Nitromethane 1-Nitro-6,7-phenanthroline (  0.2) 5-Nitro-1,10-phenanthroline 6-Nitro-1,10-phenanthroline 2-Nitrophenol 3-Nitrophenol 4-Nitrophenol (2-Nitrophenoxy)acetic acid

pK1 4.161 9.30 9.57 8.01 4.236 4.256 3.92(1) 4.11(1) 3.66 0.57 3.5(1) 6.18(1) 3.15(1) 4.76(1) 1.65 1.68 0.28(1) 2.46(1) 1.01(1) 1.73 1.88 2.11 2.18 3.46 3.441 4.15 4.12 4.05 8.57 7.63 2.21 8.984 10.21 3.23(1) 3.232(1) 3.23(1) 7.222 8.360 7.150 2.896

pK2

8.66 9.3 7.87(0) 2.94

10.06 3.33

N N

Nicotine

pK3

10.33

pK4

8.49

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance (3-Nitrophenoxy)acetic acid (4-Nitrophenoxy)acetic acid 2-Nitrophenylacetic acid 3-Nitrophenylacetic acid 4-Nitrophenylacetic acid 2-Nitrophenylarsonic acid 3-Nitrophenylarsonic acid 4-Nitrophenylarsonic acid 7-(4-Nitrophenylazo)-8-hydroxy5-quinolinesulfonic acid 3-Nitrophenylphosphonic acid 4-Nitrophenylphosphonic acid 3-(2-Nitrophenyl)propanoic acid 3-(4-Nitrophenyl)propanoic acid 3-Nitrophenylselenic acid 4-Nitrophenylselenic acid 1-Nitropropane 2-Nitropropane 2-Nitropropanoic acid 2-Nitropyridine (  0.02) 3-Nitropyridine (  0.02) 4-Nitropyridine (  0.02) N-Nitrosoiminodiacetic acid 4-Nitrosophenol Nitrourea 1,9-Nonanedioic acid (azelaic acid) Nonanoic acid (pelargonic acid) DL-Norleucine Novocaine 2,2,3,3,4,4,5,5-Octafluoropentanoic acid 1,8-Octanedioic acid (suberic acid) Octanoic acid (caprylic acid) Octopine-DD Octopine-LD Octylamine L-()-Ornithine Oxalic acid 3,6-Oxaoctanedioic acid (  1.0) Oxoacetic acid 2-Oxabutanedioic acid (oxaloacetic acid) 2-Oxobutanoic acid 5-Oxohexanoic acid (5-ketohexanoic acid) (18 C) 3-Oxo-1,5-pentanedioic acid 4-Oxopentanoic acid (levulinic acid) 2-Oxopropanoic acid (pyruvic acid)

pK1 2.951 2.893 4.00 3.97 3.85 3.37 3.41 2.90 3.14(0) 1.30 1.24 4.504 4.473 4.07 4.00 8.98 7.675 3.79 2.06(1) 0.79(1) 1.23(1) 2.28 6.48 4.15(1) 4.53 4.95 2.335(1) 8.85(1) 2.65 4.512 4.895 1.35 1.40 10.65(1) 1.94(2) 1.271 3.055 3.46 2.56 2.50 4.662 3.10 4.59 2.49

pK2

pK3

pK4

8.54 7.80 7.80 7.495(1) 6.27 6.23

3.38

5.40 9.834(0)

5.404 2.30 2.30

8.68 8.72

8.65(1) 4.272 3.676

10.76(0)

4.37

11.25 11.34

8.50

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Oxytetracycline

3.10(1)

Papaverine Pentamethylenebis(thioacetic acid) (18 C) 3,3-Pentamethylenepentanedioic acid 1,5-Pentanediamine 2,4-Pentanedione

5.90(1)

1-Pentanoic acid (valeric acid) 2-Pentenoic acid 3-Pentenoic acid 4-Pentenoic acid Pentylarsonic acid N-Pentylveratramine Perhydrodiphenic acid (20 C) Perlolidine (18 C) Peroxyacetic acid 1,7-Phenanthroline 1,10-Phenanthroline 6,7-Phenanthroline Phenazine Phenethylthioacetic acid Phenol Phenol-3-phosphoric acid Phenol-4-phosphoric acid Phenolphthalein 3-Phenolsulfonic acid Phenolsulfonephthalein Phenoxyacetic acid 2-Phenoxybenzoic acid 3-Phenoxybenzoic acid 4-Phenoxybenzoic acid 5-Phenoxy-1,2,3,4-tetrazole Phenylacetic acid L-3-Phenyl--alanine 3-Phenyl--alanine, methyl ester Phenylalanylarginine (  0.01) Phenylalanylglycine (  0.01) 7-Phenylazo-8-hydroxy5-quinolinesulfonic acid

pK2 7.26

3.485

4.413

3.49 10.05(2) 8.24(enol); 8.95(keto) 4.842 4.70 4.52 4.677 4.14 7.28(1) 4.96 4.01 8.20 4.30(1) 4.857(1) 4.857(1) 1.2(1) 3.795 9.99 1.78 1.99 9.4

6.96 10.916(1)

pK3 9.11

9.07 6.68 11.39

7.03 7.25

10.2 9.9

9.05(1) 7.9 3.171 3.53 3.95 4.52 3.49(1) 4.312 2.16(1) 7.05(1) 2.66(1) 3.10(1)

7.57(0) 7.71(0)

3.41(0)

7.850(1)

N

9.31(0)

N

1,10-Phenanthroline

12.40(1)

pK4

8.51

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 5-Phenylbarbituric acid 2-Phenyl-2-benzylsuccinic acid 1-Phenylbiguanide 4-Phenylbutanoic acid Phenylbutazone 2-Phenylenediamine 3-Phenylenediamine 4-Phenylenediamine 2-Phenylethylamine -Phenylethylboronic acid DL--Phenylglycine Phenylguanidine Phenylhydrazine 2-Phenyl-3-hydroxypropanoic acid 3-Phenyl-3-hydroxypropanoic acid Phenyliminodiacetic acid (20 C) Phenylmalonic acid Phenylmethanethiol 2-Phenyl-2-phenethylsuccinic acid (20 C) 2-Phenylphenol 3-Phenylphenol 4-Phenylphenol Phenylphosphinic acid (17 C) Phenylphosphonic acid O-Phenylphosphorylserine O-Phenylphosphorylserylglycine O-Phenylphosphoryl-L-serylL-leucine N-Phenylpiperazine (  0.1) 2-Phenylpropanoic acid 3-Phenylpropanoic acid (35 C) 3-Phenyl-1-propylamine Phenylpropynoic acid (35 C) Phenylselenic acid Phenylselenoacetic acid (  0.1) -Phenylserine (  0.16) Phenylsuccinic acid (20 C) Phenylsulfenylacetic acid Phenylsulfonylacetic acid 5-Phenyl-1,2,3,4-tetrazole 1-Phenyl-1,2,3-triazole-4-carboxylic acid 1-Phenyl-1,2,3-triazole4,5-dicarboxylic acid Phosphoramidic acid O-Phosphorylethanolamine O-Phosphorylserylglycine

pK1 2.544(1) 3.69 2.13(2) 4.757 4.5(1)  2(2) 2.65(2) 3.29(2) 9.83(1) 10.0 1.83(1) 10.77(1) 5.20(1) 3.53 4.40 2.40 2.58 10.70 3.74 9.55 9.63 9.55 2.1 1.83 2.13(1) 3.18(1) 3.16(1) 8.71(1) 4.38 4.664 10.39(1) 2.269 4.79 3.75 8.79(0) 3.78 2.66 2.44 4.38(1)

pK2

pK3

6.47 10.76(1)

4.47(1) 4.88(1) 6.08(1)

4.39(0)

4.98 5.03

6.52

7.07 8.79 6.95(0) 7.12(0)

5.55

2.88 2.13 3.08 5.838(1) 3.13

4.93 8.63 10.638(0) 5.41

8.01

pK4

8.52

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

O-Phosphoryl-L-seryl-L-leucine Phosphoserine Phthalamide Phthalazine o-Phthalic acid Phthalimide Physostigmine Picric acid (2,4,6-trinitrophenol) (18 C) Pilocarpine Piperazine 1,4-Piperazinebis(ethanesulfonic acid) (20 C) Piperazine-2-carboxylic acid Piperidine 2-Piperidinecarboxylic acid 3-Piperidinecarboxylic acid 4-Piperidinecarboxylic acid 1-(2-Piperidinyl)-2-propanone (15 C) Piperine (15 C) Proline 1,2-Propanediamine 1,3-Propanediamine 1-Propanethiol 1,2,3-Propanetriamine 1,2,3-Propanetricarboxylic acid Propanoic acid Propenoic acid N-Propionylglycine 2-Propoxybenzoic acid (20 C) 3-Propoxybenzoic acid (20 C) 4-Propoxybenzoic acid (20 C) N-Propylalanine Propylamine Propylarsonic acid (18 C) Propylenimine N-Propylglycine (  0.1) L-Propylglycine Propylmalonic acid Propylphosphinic acid

3.11 2.08 3.79(0) 3.47(1) 2.950 9.90(0) 1.76(1) 0.419 1.3(1) 5.333(2) 6.80 1.5 11.123(1) 2.12(1) 3.35(1) 3.73(1) 9.45 1.98(1) 1.952(1) 6.607(2) 8.49(2) 10.86 3.72(3) 3.67 4.874 4.247 3.718(0) 4.24 4.20 4.78 2.21(1) 10.568(1) 4.21 8.18(1) 2.38(1) 3.19(1) 2.97 3.46

pK2 5.47 5.65

O

Phthalimide

Piperazine

8.26 9.74

7.88(0)

6.85(0) 9.781(1)

5.41

9.53

10.75(0) 10.64(0) 10.72(0)

10.640(0) 9.720(1) 10.47(1) 7.95(2) 4.87

9.59(1) 6.38

10.19(0) 9.09 10.03(0) 8.97(0) 5.84

O

O N H

pK4

5.408

H N

NH

pK3

N H Piperidine

O

N

O

Piperine

8.53

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

pK2

Propylphosphonic acid 2-Propylpyridine N-Propylveratramine 2-Propynoic acid Pseudoecgonine Pseudoisocyanine (  0.2) Pseudotropine Pteroylglutamic acid Purine Pyrazine Pyrazinecarboxamide Pyrazole Pyridazine Pyridine Pyridine-d5 2-Pyridinealdoxime 3-Pyridinealdoxime 4-Pyridinealdoxime 2-Pyridinecarbaldehyde 3-Pyridinecarbaldehyde 4-Pyridinecarbaldehyde 3-Pyridinecarbamide (nicotinamide) 3-Pyridinecarbonitrile Pyridine-2-carboxylic acid (picolinic acid) Pyridine-3-carboxylic acid (nicotinic acid) Pyridine-4-carboxylic acid (isonicotinic acid) Pyridine-2,3-dicarboxylic acid Pyridine-2,4-dicarboxylic acid Pyridine-2,6-dicarboxylic acid Pyridine-1-oxide Pyridoxal

2.49 6.30(1) 7.20(1) 1.887 9.70 4.59(2) 9.86(1) 8.26 2.52(1) 0.6(1) 0.5(1) 2.61(1) 2.33(1) 5.17(1) 5.83(1) 3.56(1) 4.07(1) 4.73(1) 3.84(1) 3.80(1) 4.74(1) 3.33(1) 1.35(1)

8.18

1.01(1)

5.29(0)

2.07(1)

4.75(0)

1.84(1) 2.36(1) 2.23(1) 2.16(1) 0.688(1) 4.20(1)

4.86(0) 7.08(0) 7.02(0) 6.92(0)

Pyridoxal-5-phosphate (  0.15) Pyridoxamine (  0.1)

 2.5 3.37(2)

Pyridoxamine-5-phosphate (  0.15; pK5  10.92) Pyridoxine (vitamin B6) (18 C)

2.5 5.00(1)

N

pK3

pK4

8.92(0)

10.17(0) 10.39(0) 10.03(0)

8.66(ring OH) 4.14 8.01(1)

3.69 8.96(ring OH)

6.20 10.13(ring OH)

8.69

5.76

8.61

N

N

N N N

N H

N Purine

Pyrazine

N

NH N

Pyrazole

Pyridazine

Pyridine

8.54

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1 1.37(2) 1.77(2)

pK2

pK3

3-(2-Pyridyl)alanine 3-(3-Pyridyl)alanine 2-(2-Pyridyl)benzimidazole (  0.16) 2-(2-Pyridyl)imidazole (  0.005) 4-(2-Pyridyl)imidazole (  0.1) Pyrimidine 2,4(1H,3H)-Pyrimidinedione (uracil) 2,4,5,6(1H,3H)-Pyrimidinetetrone5-oxime Pyrocatecholsulfonephthalein Pyroxilidine Pyrrole-1-carboxylic acid Pyrrole-2-carboxylic acid Pyrrole-3-carboxylic acid Pyrrolidine Pyrrolidine-2-carboxylic acid (proline) 2-[2-(N-Pyrrolidinyl)ethyl]pyridine 3-[2-(N-Pyrrolidinyl)ethyl]pyridine 4-[2(N-Pyrrolidinyl)ethyl]pyridine 2-(1-Pyrrolidinylmethyl)pyridine 3-(1-Pyrrolidinylmethyl)pyridine 4-(1-Pyrrolidinylmethyl)pyridine 3-Pyrroline

4.02(1) 4.64(1)

1.952(1) 3.60(2) 4.28(2) 4.65(2) 2.54(1) 3.14(2) 3.38(2) 0.27(1)

10.640(0) 9.39(1) 9.28(1) 9.27(1) 8.56(1) 8.36(1) 8.16(1)

Quinidine Quinine Quinoline Quinoxaline

4.0(1) 4.11(1) 4.80(1) 0.72(1)

8.54(0) 8.52(0)

D-Raffinose

12.74 ca 0.2 12.11

pK4

9.22(0) 9.10(0)

5.58(1) 8.98(1) 5.49(1) 1.30(1) 0.6(1) 4.57(0) 7.82 11.11(1) 4.45 4.45 4.453 11.305(1)

Riboflavin (vitamin B2) (  0.01) -D-Ribofuranose D-Ribose-5-phosphonic acid

9.46(0)

9.76

11.73

9.69 6.70(1)

13.05(2)

OH HO HO

OH O

O

OH O

O HO

N H Pyrrolidine

N Quinoline

OH O

OH OH D-Raffinose

OH OH

8.55

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

D-Saccharic acid Saccharin (o-benzoic sulfimide) Sarcosine Sarcosine amide Sarcosine dimethylamide Sarcosine methylamide Sarcosylglycine (  0.16) Sarcosylleucine Sarcosylsarcosine Sarcosylserine 3-Selenosemicarbazide (  0.1) Semicarbazide (  0.1) L-Serine Serine, methyl ester (  0.1) Serylglycine (  0.15) L-Seryl-L-leucine Solanine D-Sorbitol (17.5 C) L-()-Sorbose (18 C) Sparteine Spinaceamine (  0.1) Spinacine L-Strychnine (15 C) Succinamic acid (succinic acid monoamide) Succinic acid DL-Succinimide -(4-Sulfaminophenyl)alanine 3-Sulfamylbenzoic acid 4-Sulfamylbenzoic acid 4-Sulfamylphenylphosphoric acid Sulfanilamide Sulfoacetic acid 3-Sulfobenzoic acid 4-Sulfobenzoic acid 3-Sulfophenol 4-Sulfophenol 2-Sulfopropanoic acid 5-Sulfosalicylic acid Sylvic acid D-Tartaric acid meso-Tartaric acid

N H

5.00(0) 2.32 2.12(1) 8.35(1) 8.86(1) 8.28(1) 3.15(1) 3.15(1) 2.92(1) 3.17(1) 0.8(1) 3.53(1) 2.186(1) 7.03(1) 2.10(1) 3.08(1) 7.34(1) 13.60 11.55 4.49(1) 4.895(2) 1.649(2) 2.50

pK3

8.56(0) 8.67(0) 9.15(0) 8.63(0)

9.208(0) 7.33(0) 7.45(0)

11.76(0) 8.90(1) 4.936(1) 8.20

4.39(0) 4.207 9.623 1.99(1) 3.54 3.47 1.42 10.43(1)

8.663(0)

5.635 8.64(0)

10.26(1)

6.38

10.0

4.0 3.78 3.72 9.07 8.70

0.39 0.58 1.99 2.49 7.62

12.00 4.366 4.81 OH

O NH2

Semicarbazide

H2N

pK4

10.20(0)

3.036 3.22

O H2N

pK2

S O Sulfanilamide

NH 2

O

HO OH O

OH

D-Tartaric

acid

8.56

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Tetracycline (  0.005) Tetradehydroyohimbine Tetraethylenepentamine [  0.1; pK5  9.67(1)] 1,4,5,6-Tetrahydro1,2-dimethylpyridine 1,4,5,6-Tetrahydro-2-methylpyridine cis-Tetrahydronaphthalene2,3-dicarboxylic acid (20 C) trans-Tetrahydronaphthalene2,3-dicarboxylic acid (20 C) 5,6,7,8-Tetrahydro-1-naphthol 5,6,7,8-Tetrahydro-2-naphthol Tetrahydroserpentine 2,3,5,6-Tetramethylbenzoic acid Tetramethylenebis(thioacetic acid) (18 C) Tetramethylenediamine N,N,N,NTetramethylethylenediamine 2,3,5,6-Tetramethyl4-methylaminopyridine 2,2,6,6-Tetramethylpiperidine (  0.5) 2,3,5,6-Tetramethylpyridine (20 C) Tetramethylsuccinic acid 1,2,3,4-Tetrazole Thebaine 2-Thenoyltrifluoroacetone Theobromine Theophylline Thiazoline Thioacetic acid o-Thiocresol m-Thiocresol p-Thiocresol Thiocyanatoacetic acid 2,2-Thiodiacetic acid 4,4-Thiodibutanoic acid (18 C)

pK2

N

N

pK4

3.30(1) 10.59(1)

7.68

9.69

2.98(5)

4.72(4)

8.08(3)

11.38(1) 9.53(1) 3.98

6.47

4.00 10.28 10.48 10.55(1) 3.415

5.70

3.463 9.22(2)

4.423 10.75(1)

2.20(2)

6.35(1)

0.07(1) 1.24(1) 7.90(1) 3.50 4.90 7.95(1) 5.70(0) 0.68(1)  1(1) 2.53(1) 3.33 6.64 6.58 6.52 2.58 3.32 4.351

7.28

7.89 8.80

4.29 5.275

CH3 H3C

pK3

CH3

CH3 N,N,N',N'-Tetramethylethylenediamine

NH

S

N

N N

1,2,3,4-Tetrazole

N Thiazoline

9.10(2)

8.57

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

3,3-Thiodipropanoic acid (18 C) 3-Thio-S-methylcarbazide (  0.1) 1-Thionylcarboxylic acid 2-Thionylcarboxylic acid 2-Thiophenecarboxylic acid (30 C) 3-Thiophenecarboxylic acid (3-thenoic acid) Thiophenol 3-Thiosemicarbazide (  0.1) 3-Thiosemicarbazide-1,1-diacetic acid (30 C) Thiourea Thorin Thymidine p-Toluenesulfinic acid Toluhydroquinone o-Toluidine m-Toluidine p-Toluidine o-Tolylacetic acid (18 C) p-Tolylacetic acid (18 C) o-Tolylarsonic acid m-Tolylarsonic acid p-Tolylarsonic acid o-Tolylphosphonic acid m-Tolylphosphonic acid p-Tolylphosphonic acid 3-Tolylselenic acid 4-Tolylselenic acid Triacetylmethane Triallylamine 1,3,5-Triazine-2,4,6-triol 1H-1,2,3-Triazole 1H1,2,4-Triazole 1,2,3-Triazole-4-carboxylic acid 1,2,3-Triazole-4,5-dicarboxylic acid 1,2,4-Triazolidine-3,5-dione (urazole) Tribromoacetic acid 2,4,6-Tribromobenzoic acid Trichloroacetic acid Trichloroacrylic acid

4.085 7.563(1) 3.53 4.10 3.529

pK2

pK3

5.075

4.10 6.50 1.5(1) 2.94 2.03(1) 3.7 9.79 1.7 10.03 4.45(1) 4.71(1) 5.08(1) 4.36 4.36 3.82 3.82 3.70 2.10 1.88 1.84 4.80 4.88 5.81 8.31(1) 7.20 2.386(1) 3.22 1.86 5.80 0.147 1.41 0.52 1.15

4.07 8.3 12.85

11.8

11.62

8.85 8.60 8.68 7.68 7.44 7.33

11.10 9.26 9.972 8.73 5.90

9.30

O HO HO

NH N O

Thymidine

O

H2N o-Toluidine

pK4

8.58

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance 3,3,3-Trichlorolactic acid Trichloromethylphosphonic acid 2,4,5-Trichlorophenol 3,4,5-Trichlorophenol Tricine (20 C) Triethanolamine Triethylamine Triethylenediamine Triethylenetetramine (20 C) Triethylsuccinic acid Trifluoroacetic acid Trifluoroacrylic acid 4,4,4-Trifluoro-2-aminobutanoic acid 4,4,4-Trifluoro-3-aminobutanoic acid 4,4,4-Trifluorobutanoic acid ,,-Trifluoro-m-cresol 4,4,4-Trifluorocrotonic acid 5,5,5-Trifluoroleucine 3-(Trifluoromethyl)aniline 4-(Trifluoromethyl)aniline 3-Trifluoromethylphenol 5-Trifluoromethyl-1,2,3,4-tetrazole 6,6,6-Trifluoronorleucine 5,5,5-Trifluoronorvaline 5,5,5-Trifluoropentanoic acid 3,3,3-Trifluoropropanoic acid 4,4,4-Trifluorothreonine 4,4,4-Trifluorovaline 1,2,3-Trihydroxybenzene (pyrogallol) 1,3,5-Trihydroxybenzene (phloroglucinol) 2,4,6-Trihydroxybenzoic acid 3,4,5-Trihydroxybenzoic acid 3,4,5-Trihydroxycyclohex-1-ene1-carboxylic acid [D-()-shikimic acid] 2,4,6-Tri(hydroxymethyl)phenol Triisobutylamine Trimethylamine 3-(Trimethylamino)phenol 4-(Trimethylamino)phenol 2,4,6-Trimethylaniline 2,4,6-Trimethylbenzoic acid Trimethylenebis(thioacetic acid) (18 C) 2,3,4-Trimethylphenol 2,4,5-Trimethylphenol 2,4,6-Trimethylphenol 3,4,5-Trimethylphenol 2,3,6-Trimethylpyridine (  0.5)

pK1 2.34 1.63 7.37 7.839 8.15 7.76(1) 10.72(1) 4.18(2) 3.32(4) 2.74 0.50 1.79 1.600(1) 2.756(1) 4.16 8.950 3.15 2.045(1) 3.5(1) 2.6(1) 8.950 1.70 2.164(1) 2.042(1) 4.50 3.06 1.554(1) 1.537(1)

pK2

pK4

9.20(2)

9.92(1)

4.81

8.19(1) 6.67(3)

8.169(0) 5.822(0)

8.942(0)

9.463(0) 8.916(0)

7.822(0) 8.098(0)

9.03(0) 8.45(0)

11.63(1) 8.88(1)

1.68(0) 4.19(0)

8.85(1)

4.15 9.56 10.42(1) 9.80(1) 8.06 8.35 4.38(1) 3.448 3.435

5.383

10.59 10.57 10.88 10.25 7.60(1)

pK3

8.59

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

2,4,6-Trimethylpyridine 2,4,6-Trimethylpyridine-1-oxide 3-(Trimethylsilyl)benzoic acid 4-(Trimethylsilyl)benzoic acid 2,4,5-Trimethylthiazole (  0.1) 2,4,6-Trinitroaniline (picramide) 2,4,6-Trinitrobenzene acid 2,2,2-Trinitroethanol Trinitromethane (20 C) Triphenylacetic acid Tripropylamine Tris(2-hydroxyethyl)amine Tris(hydroxymethyl)aminomethane (TRIS) 2-[Tris(hydroxymethyl)methyl amino]-1-ethanesulfonic acid (TES) 3-[Tris(hydroxymethyl)methyl amino]-1-propanesulfonic acid (TAPS) (20 C) N-[Tris(hydroxymethyl)methyl]glycine (tricine) Tris(trimethylsilyl)amine Trithiocarbonic acid (20 C) Tropacocaine (15 C) 3-Tropanol (tropine) Trypsin (  0.1) L-Tryptophan DL-Tyrosine Tyrosine amide

pK2

pK3

pK4

7.43(1) 1.990(1) 4.089 4.192 4.55 10.23(1) 0.654 2.36 0.17 3.96 10.66(1) 7.762(1) 8.08(1)

7.50

8.4 2.023(1) 4.70(1) 2.64 9.88(1) 10.33(1) 6.25 2.38(1) 2.18(1) 7.48

8.135

9.39(0) 9.21(0) 9.89

10.47(OH)

OH OH

OH HO

NH2

N

HO OH O S O

Tris(hydroxymethyl)aminomethane

OH

2-[Tris(hydroxymethyl)methylamino]-1-ethanesulfonic acid HO O

S

OH

O N

OH OH

3-[Tris(hydroxymethyl)methylamino]-1-propanesulfonic acid

8.60

SECTION 8

TABLE 8.1 pKA Values of Organic Materials in Water at 25 C (continued) Substance

pK1

Tyrosine, ethyl ester Tyrosylarginine (  0.01) Tyrosyltyrosine

7.33 2.65(1) 3.52(1)

-Ureidobutanoic acid -Ureidobutanoic acid -Ureidopropanoic acid Uric acid Uridine Uridine-5-diphosphoric acid Uridine-5-phosphoric acid (5-uridylic acid) Uridine-5-triphosphoric acid

3.886(0) 4.683(0) 4.487(0) 5.40 9.30 7.16

DL-Valine

2.286(1) 2.296(1) 8.00 7.49(1) 3.23(1) 7.49(1) 8.85(1) 9.69(1) 4.98(1) 5.62(1) 7.64(1)

pK2 9.80 7.39(0) 7.68(0)

pK3

pK4

9.36(1) 9.80(1)

11.62(2) 10.26(2)

5.53

6.63 7.58

L-Valine

Valine amide (  0.2) L-Valine, methyl ester L-Valylglycine

Vetramine Veratrine Vinylmethylamine 2-Vinylpyridine 4-Vinylpyridine Vitamin B12 Xanthine (40 C) Xanthosine Xylenol Orange [pK5  10.46(4); pK6  12.28(5)] D-()-Xylose

9.719(0) 9.79(0)

8.00(0)

0.68(1)  2.5(1)

5.67(0)

12.00(1)

2.58(1)

3.23(2)

6.37(3)

4

7.85

15

12.15(0)

Zincon

O H N O N H

OH

HO NH HO N H

Uric acid

O

O

N

O NH O

Uridine

Table 8.2 records the acidities of inorganic compounds expressed as their pKA values (see page 8.2 for a discussion of pKA). When more than one ionizable proton is present, pK1, pK2, etc. values are given. Cations formed from the indicated compound by protonation are indicated by “(1)” or “(2)” for a dication. Temperature values different from 25 C are given in parentheses as are other relevant variations. For example, the dissociation constant for acetic acid-d1 is reported in D2O.

8.61

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.2 Proton-Transfer Reactions of Inorganic Materials in Water at 25 C The protonation states of cations are designated by values (1), (2), etc. that follow pKA values. Substance Aluminic acid (alumina) Amidophosphoric acid Aminodisulfonic acid Ammonium ion Arsenic acid Arsenous acid Boric acid, orthoBoric acid, etraCarbonic acid

Chloric acid Chlorous acid Chlorosulfonic acid Chromic acid Cyanic acid Deuterium oxide Diamidophosphoric acid Dithionic acid Dithionous acid Ferricyanic acid Ferrocyanic acid Fluorophosphoric acid Hexapolyphosphoric acid Hydrazinium(2) ion (20 C) Hydrazinosulfuric acid Hydrazoic acid Hydrocyanic acid Hydrogen bromide Hydrogen chloride Hydrogen fluoride Hydrogen iodide Hydrogen peroxide Hydrogen polysulfide (20 C) Hydrogen selenide Hydrogen sulfide Hydrogen telluride (20 C) Hydroperoxy radical Hydroxide radical Hydroxylamine-N,N-di sulfonic acid Hydroxylamine-N-sulfonic acid Hydroxylammonium ion

Formula H3AlO3 H2NPO(OH)2 HN(SO3H)2 NH4 H3AsO4 HAsO2 or HAs(OH)4 H3BO3 H2B4O7 CO2  H2O (without including dehydration constant) CO2  D2O (solvent) HClO3 HClO2 HOSO2Cl H2CrO4 HOCN D2O (solvent) (H2N)2PO2H H2S2O6 H2S2O4 H3Fe(CN)6 H2(Fe(CN)6)2 FPO(OH)2 H8P6O19  H3NNH3

pK1

pK2

11.2 3.3

8.28

pK4

8.50 9.24 2.25 9.23 9.236 4 6.35 3.76 6.77 1.58 2.021 10.43 0.98 3.47 14.87 4.83 3.4 0.35 1

H2NNHSO3H HN3 HCN HBr HCl HF HI H2O2

ca 2.1 0.88 (2) 3.85 4.64 9.21 20.68 6.1 3.17 9.5 11.58

H2S4 H2Se H2S H2Te HO.2HO 2 OH.

3.8 3.89 6.96 2.64 4.45 11.9

6.77

11.53

12.74 9 10.53 10.329 11.076

6.50

0.2 2.45

4.79 2.19 7.956 (1)

2.57

4.35

5.98

8.13

6.3 11.0 12.90 11–12

HON(SO3H)2 HONH ˆ OSO2H HONH3

pK3

11.85 ca 12.5 5.98

8.62

SECTION 8

TABLE 8.2 Proton-Transfer Reactions of Inorganic Materials in Water at 25 C (continued) Substance Hypobromous acid Hypochlorous acid Hypoiodous acid Hyponitrous acid Hypophosphoric acid (20 C) Hypophosphorus acid Hyposulfurous acid Imidodiphosphoric acid Iodic acid (30 C) Nitramide Nitric acid Nitrous acid Osmic acid Perchloric acid

Periodic acid, paraPermanganic acid Peroxide radical Peroxoboric acid Peroxochromic acid Peroxomonosulfuric acid Perxenic acid Phosphoric acid, orthoDeuterated Phosphoric acid, diPhosphorous acid (20 C) Selenic acid Selenous acid Silicic acid Sulfamic acid Sulfuric acid Sulfurous acid Telluric acid Tellurous acid Tetraperoxochromic acid (30 C) Tetrapolyphosphoric acid (pK5  6.63; pK6  8.34) Thiocyanic acid Thiosulfuric acid Trimetaphosphoric acid Tripolyphosphoric acid (  1)* (pK5  9.26) Trithiocarbonic acid (20 C)

Formula

pK1

pK2

HBrO HClO HIO HON ¨ NOH

8.597 7.54 10.64 7.05

11.54

H4P2O6 HPH2O2 H2S2O4 (HO)2PO ˆ NH ˆ PO(OH)2 HIO3 O2NNH2 HNO3 HNO2 H2OsO5 (mainly OsO4) HCIO4 (completely dissociated up to 10 M) H5IO6 HMnO4 HO.2 H3BO3  H2O2  (H2BO3 · H2O2)  H H2CrO5 H2SO5 H4XeO6 H3PO4 D3PO3 H4P2O7 H2PHO3 H2SeO4 H2SeO3 H2SiO3 HOSO2NH2 H2SO4 SO2  H2O (includes dehydration constant) H6TeO6 H2TeO3

2 1.23 0.35

2.19

ca 2 0.815 6.48 1.38 3.14 12.0

2.85

H3CrO8 H6P4O13 HSCN H2S2O3 H3P3O4 H5P3O10

H2CS3

1.55 2.25 4.90

pK3

pK4

7.08

9.72

2.45

14.5

8.27

7.91 4.30 1.0 ca 2 2.148 2.420 0.91 1.20 3 2.27 9.77 0.988 ca 3

9.3 ca 6 7.198 7.201 2.10 6.70 1.74 7.78 11.80

1.89 7.70 2.46

7.20 10.99 7.7

ca 10 12.38 6.70

9.38

1.3

2.23

2.0 2.30

6.61

1.987

7.16

0.95 0.60

1.5–1.7

0.51

1.20

2.68

8.18

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

8.63

TABLE 8.2 Proton-Transfer Reactions of Inorganic Materials in Water at 25 C (continued) Substance Tungstic acid (20 C) Vanadic acid Water Xenon trioxide

* Ionic strength.

Formula H2WO4 H3VO4 H2O XeO3 (aqueous)  HXeO4  H

pK1 ca 3.5 3.78 14.003 10.8

pK2

pK3

ca 4.6 7.8

13.0

pK4

8.64

TABLE 8.3 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures Abbreviations Used in the Table (1), monoprotonated cation (1), monoanion pKauto, negative logarithm (base 10) of autoprotolysis constant (0), neutral molecule (2), dianion pKsp, negative logarithm (base 10) of solubility product Temperature, C Substance Acetic acid (0) DL-N-Acetylalanine (1) -Acetylaminopropionic (1) N-Acetylglycine (1) -Alanine (1) (0) 2-Aminobenzenesulfonic acid (0), pK2 3-Aminobenzenesulfonic acid (0), pK2 4-Aminobenzenesulfonic acid (0), pK2 3-Aminobenzoic acid (0) 4-Aminobenzoic acid (0) 2-Aminobutyric acid (1) (0) 4-Aminobutyric acid (1) (0) 2-Aminoethylsulfonic acid (0) 2-Amino-3-methylpentanoic acid (1) (0)

0 4.780

5 4.770 3.699 4.479 3.682

2.42 10.59

10

15

4.762 3.699 4.465 3.676

4.758 3.703 4.465 3.673

2.39 10.29

20

25

30

35

40

50

4.757 3.708 4.449 3.667

4.756 3.715 4.445 3.670

4.757 3.725 4.444 3.673

4.762 3.733 4.443 3.678

4.769 3.745 4.445 3.685

4.787 3.774 4.457 3.706

2.35 10.01

2.34 9.87

2.33 9.74

2.33 9.62

2.33 9.49

2.33 9.26

2.633

2.591

2.556

2.521

2.448

2.459

2.431

2.404

2.380

2.338

4.075

4.002

3.932

3.865

3.799

3.738

3.679

3.622

3.567

3.464

3.521

3.457

3.398

3.338

3.283 4.90 4.95

3.227 4.79 4.85

3.176 4.75 4.90

3.126

3.079 4.68 4.95

2.989 4.60 5.10

2.334 10.530 4.057 11.026 9.452 2.3651 C 10.4601 C

2.33812.5 C 10.10012.5 C

2.28937.5 C 9.51837.5 C

2.286 9.380 4.046 10.867 9.316

4.038 10.706 9.186

4.031 10.556 9.061 2.320 9.758

4.027 10.409 8.940

4.025 10.269 8.824 2.31737.5 C 9.43937.5 C

2.297 9.234 4.027 10.114 8.712

4.032 9.874 9.499 2.332 9.157

2-Amino-2-methyl1,3-propanediol 2-Amino-2-methylpropionic acid (1) (0) 2-Aminopentanoic acid (1) (0) 3-Aminopropionic acid (1) (0) 4-Aminopyridine (1) Ammonium ion (1) Arginine (1) (0) Barbituric acid (1) (0) Benzoic acid (0) Boric acid (0) Bromoacetic acid (0) 3-Bromobenzoic acid (0) 4-Bromobenzoic acid (0) Bromopropynoic acid (0) 3-tert-Butylbenzoic acid (0) 4-tert-Butylbenzoic acid (0) 2-Butynoic acid (0) Butyric acid (0) DL-N-Carbamoylalanine (1) N-Carbamoylglycine (1)

9.612

9.433

9.266

2.4191 C 10.9601 C

2.38012.5 C 10.58012.5 C

2.3761 C 10.5081 C

2.347

9.104

8.951

8.801

8.659

8.519

8.385

8.132

2.357 10.205

2.35137.5 C 9.87237.5 C

10.15412.5 C

2.318 9.808

9.49037.5 C

9.252 9.400

3.551 10.235 9.114 9.425

8.978 9.093

3.524 9.963 8.846 8.947

3.517 9.842 8.717 8.805

8.477 8.539

2.356 9.561 2.309

2.313 9.198

3.656 11.000 9.873 10.081

3.627 10.830 9.704 9.904

9.549 9.731

3.583 10.526 9.398 9.564

1.914 9.718

1.885 9.563

1.870 9.407

1.849 9.270

1.837 9.123

1.823 8.994

1.814 8.859

1.801 8.739

1.800 8.614

1.787 8.385

3.969 8.493 4.215 9.327 2.875 3.818 4.011 1.814 4.266 4.463 2.626 4.805 3.891 3.889

3.980 8.435 4.206 9.280 2.887 3.813 4.005 1.839 4.231 4.425 2.611 4.810 3.890 3.879

4.02 8.372 4.204 9.236 2.902 3.810 3.99 1.855 4.199 4.389 2.620 4.817 3.892 3.876

4.00 8.302 4.203 9.197 2.918 3.808 4.001 1.879 4.170 4.354 2.618 4.827 3.896 3.874

4.008 8.227 4.207 9.161 2.936 3.810 4.001 1.900 4.143 4.320 2.621 4.840 3.902 3.873

4.017 8.147 4.219 9.132

4.032 7.974 4.223 9.080

3.813 4.003 1.919 4.119 4.287 2.631 4.854 3.908 3.875

4.885 3.931 3.888

9.508

4.231 9.439

4.220 9.380

1.786

4.806

4.804 3.898 3.911

2.618 4.803 3.894 3.900

8.65

8.66

TABLE 8.3 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures (continued) Temperature, C Substance Carbon dioxide  water (0) (1) Chloroacetic acid (0) 3-Chlorobenzoic acid (0) 4-Chlorobenzoic acid (0) Chloropropynoic acid (0) Citric acid (0) (1) (2) Cyanoacetic acid (0) 2-Cyano-2-methylpropionic acid (0) 5,5-Diethylbarbituric acid (0) Diethylmalonic acid (0) (1) 2,3-Dimethylbenzoic acid (0) 2,4-Dimethylbenzoic acid (0) 2,5-Dimethylbenzoic acid (0) 2,6-Dimethylbenzoic acid (0) 3,5-Dimethylbenzoic acid (0) N,N-DimethylethyleneamineN,N-diacetic acid (0) (1)

0

5

6.583 10.627

6.517 10.558

3.220 4.837 6.393

8.40

6.294 10.446

10

6.465 10.499

15

20

25

30

35

40

50

6.297 10.172

6.382 10.377 2.856 3.831 3.991 1.820

6.365 10.33 2.867 3.83 3.986 1.845

6.327 10.290 2.883 3.825 3.981 1.864

6.31 10.25 2.900 3.826 3.980 1.879

6.296 10.220

1.766

6.429 10.431 2.845 3.838 4.000 1.796

3.200 4.813 6.386 2.445

3.176 4.797 6.383 2.447

3.160 4.782 6.384 2.452

3.142 4.769 6.388 2.460

3.128 4.761 6.396 2.460

3.116 4.755 6.406 2.482

3.109 4.751 6.423 2.496

3.099 4.750 6.439 2.511

2.342 8.30

2.360 8.22

2.379 8.169

2.400 8.094

2.422 8.020

2.446 7.948

2.471 7.877

2.498 7.808

2.129 7.400

2.136 7.401 3.663 4.154 3.911 3.234 4.292

2.144 7.408 3.687 4.187 3.954 3.304 4.299

2.151 7.417 3.771 4.217 3.990 3.362 4.302

2.160 7.428 3.726 4.244 4.020 3.409 4.304

2.172 7.441 3.762 4.268 4.045 3.445 4.306

2.187 7.457 3.788 4.290 4.065 3.472 4.306

6.169 10.268

6.047 10.068

5.926 9.882

3.829 3.981 1.893

5.803 9.684

3.095 4.757 6.484

7.673

N,N-Dimethylglycine (0) 3,5-Dinitrobenzoic acid (0) 2-Ethylbutyric acid (0) 5-Ethyl-5-phenylbarbituric acid (0) Fluoroacetic acid (0) Formic acid (0) 2-Furancarboxylic acid (0) Glucose-1-phosphate (0) Glycerol-1-phosphoric acid (1) Glycerol-2-phosphoric acid (0) (1) Glycine (1) (0) Glycolic acid (0) Glycylasparagine (1) N-Glycylglycine (1)

8.67

Hexanoic acid (0) Hydrogen cyanide (0) Hydrogen peroxide (0) Hydrogen sulfide (0) (1) 4-Hydroxybenzoic acid (0) Hydroxylamine (0) 2-Hydroxy-1-naphthoic acid (0) (1) 4-Hydroxyproline (1) (0)

10.34 4.623

3.786

10.14 2.60 4.664

9.94 2.73 4.710 7.517 2.571 3.753

7.311 2.624 3.758 3.216 6.519 6.679

2.96 4.812 7.248

3.07 4.869 7.130

3.766 3.239 6.531 6.695

3.782 6.561 6.733

3.772

3.762

7.592 2.555 3.757

6.506 6.642

6.500 6.641

6.499 6.643

6.500 6.648

4.751 7.445 2.586 3.751 3.164 6.504 6.656

1.223 6.657

1.245 6.650

1.271 6.646

1.301 6.646

1.335 6.650

1.372 6.657

1.413 6.666

1.457 6.679

1.554 6.712

2.397 10.193 3.84412.5 C 2.958

2.380 10.044

2.36 9.91

2.34 9.65

2.952

2.943

2.351 9.780 3.831 2.942 3.126 8.252

2.33 2.327 9.53 9.412 3.83337.5 C 2.944 2.947

9.49 11.86

4.849 9.36 11.75

2.32 9.19 3.849 2.959 3.159 7.668 4.920

10.34 3.875 2.968 3.201

8.59412.5 C 4.839 9.63

4.840 12.23 7.33 13.5

7.24

7.13 13.2 4.596 6.186

7.05 4.586 6.063

9.21 11.65 6.97 12.90 4.582 5.948

3.29 9.68 1.9001 C 10.2741 C

9.76 2.85 4.758 7.377 2.604 3.752 3.200 6.510 6.666

1.85012.5 C 9.95812.5 C

2.942

7.94837.5 C 4.865 9.11 11.55 6.90 12.75 4.577

8.99 11.45 6.82 12.6 4.576 5.730

3.24 9.65 1.818 9.662

4.890 8.88

11.21 6.79 4.578

3.19 9.61 1.79837.5 C 9.39437.5 C

6.69

3.26 9.58 1.796 9.138

8.68

TABLE 8.3 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures (continued) Temperature, C Substance 2-Hydroxypropionic acid (0) DL-2-Hydroxysuccinic acid (0) (1) Hypobromous acid (0) Hypochlorous acid (0) Imidazole (1) Iodoacetic acid (0) DL-Isoleucine (1) (0) Isopropylmalonic acid, mononitrile (0) Lactic acid (0) Lead sulfate, pKsp DL-Leucine (1) (0) Malonic acid (1) Mannose (0) Mercury(I) chloride, pKsp Methanol (solvent), pKauto Methylamine (1) Methylaminodiacetic acid (0) (1)

0

5

10

15

20

25

30

35

40

50 3.895

3.880

3.873

3.868

3.861

3.857

3.858

3.861

3.867

3.873

3.537 5.119

3.520 5.108

3.494 5.098

3.472 5.096

7.75 7.467

7.69 7.334

3.458 5.097 8.60 7.54 6.993 3.175

3.452 5.099

7.82 7.581

3.482 5.096 8.83 7.63 7.216 3.143

3.446 5.104 8.47 7.46 6.784 3.213

3.444 3.445 5.117 5.149 8.3745 C 7.05 6.685 6.497

2.33812.5 C 10.10012.5 C

2.365 10.460

3.880 8.01 2.3831 C 10.4581 C 5.670

7.58 7.103 3.158

2.299 3.873

2.320 3.868

5.665

2.34812.5 C 10.0951.5 C 5.667 12.45 18.65

17.12

7.50 6.887 3.193

2.31737.5 C 9.43937.5 C

2.318 9.758 2.343 3.862 7.87

2.365 3.857

5.673

5.683

18.48 16.84

18.27

11.496

11.130

10.787

2.138 10.474

2.142 10.287

2.146 10.088

2.401 3.858 7.80 2.328 9.744 5.696 12.08 17.88 16.71 10.62

2.427 3.861

5.710

16.65 10.466 2.150 9.920

2.452 3.867 7.73

2.332 9.157 2.481 3.873

2.32737.5 C 9.43437.5 C 5.730 5.753 11.81 16.79 16.53 10.161 2.154 9.763

3.895 7.63 2.333 9.142 5.803

9.876

3-Methylbenzoic acid (0) 4-Methylbenzoic acid (0) 3-Methylbutyric acid (0) 4-Methylpentanoic acid (0) 5-Methyl-5-phenylbarbituric acid (0) 2-Methylpropionic acid (0) 2-Methyl-2-propylamine (1) Nitric acid (0) Nitrilotriacetic acid (0) (1) (2) 4-Nitrobenzoic acid (0) Nitrous acid (0) DL-Norleucine (1) (0) Oxalic acid (1) 2,4-Pentanedione (0) Pentanoic acid (0) Phenylalanine (0) Phosphoric acid (0) (1) o-Phthalic acid (0) (1) Piperidine (1) Proline (1) (0)

4.303 4.390 4.726 4.827

4.742 4.827

4.825

4.827 11.240

8.104 11.439

11.048

4.285 4.376 4.767 4.837

4.269 4.362

8.057 4.840 10.862

8.011 4.853 10.682 1.38

1.65 1.69 2.95 10.59

1.65 2.95 10.45 3.448 3.244

1.65 2.94 10.33 3.444 3.177

3.441 3.138

2.394 10.564 4.210 9.07 4.823

4.216

2.35612.5 C 10.19012.5 C 4.227

2.056 7.313

2.073 7.282

4.763 9.75 2.088 7.254

2.107 7.231

2.127 7.213

2.335 9.834 4.272 8.95 4.842 9.31 2.148 7.198

2.925 5.432 11.963

2.927 5.418 11.786

2.931 5.410 11.613

2.937 5.405 11.443

2.943 5.405 11.280

2.950 5.408 11.123

2.011 11.296

1.96412.5 C 10.97212.5 C

4.240

4.254 4.835

1.952 10.640

4.256 4.349 4.794 4.853

4.244 4.336

7.966 4.886 10.511

7.922

4.235 4.322 4.831 4.879

4.871 4.908

7.879 4.918

7.797 4.955

10.341 1.20

1.66 2.96 10.23 3.441

4.295

1.67 2.98 3.442 3.100 2.32437.5 C 9.51337.5 C 4.318

3.445

2.171 7.189

2.196 7.185

4.349 8.90 4.861 8.96 2.224 7.181

2.958 5.416 10.974

2.967 5.427 10.818

2.978 5.442 10.670

4.851

1.95037.5 C 10.34237.5 C 10.064

2.328 9.224 4.409 4.906 2.277 7.183 3.001 5.485 10.384 1.958

8.69

8.70

TABLE 8.3 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures (continued) Temperature, C Substance Propenoic acid (0) N-Propionylglycine (1) Propynoic acid (0) Pyrrolidine (1) Serine (1) (0) Silver bromide, pKsp Silver chloride, pKsp Succinic acid (0) (1) Sulfuric acid (1) Sulfurous acid (0) D-Tartaric acid (0) (1) 2,3,5,6-Tetramethylbenzoic acid (0) Threonine (1) (0) o-Toluidine (0) 1,2,4-Triazole (1) (0) 3,4,5-Trihydroxybenzoic acid (0)

0

5

3.728 12.17

11.98

2.2961 C 9.8801 C

10

15

3.723 1.791 11.81

4.267 3.718 1.829 11.63

25

30

35

4.250 3.716 1.867 11.43

4.247 3.718 1.887 11.30

4.249 3.721 1.940 11.15

4.267 3.725 1.932 10.99

2.23212.5 C 9.54212.5 C 13.33 10.595

4.285 5.674 1.778 1.63

4.263 5.660 1.8124.3 C

3.118 4.426

3.095 4.407

2.2001 C 9.7481 C

20

4.245 5.649

4.301 3.731 1.963 10.84

11.56

2.15437.5 C 8.90437.5 C 11.83 11.61 9.381 9.21

2.132 8.628 11.19 8.88

3.750

12.57

4.232 5.642 1.894

4.218 5.639

4.207 5.635 1.987 1.89

4.198 6.541 2.05

4.191 5.647 2.095 1.98

4.188 5.654 2.17

4.186 5.680 2.246 2.12

3.057 4.381 3.310

3.044 4.372 3.367

3.036 4.366 3.415

3.025 4.365 3.453

3.019 4.367 3.483

3.018 4.372 3.505

3.021 4.391

4.58

4.495

2.088 9.100 4.45

4.345

2.07037.5 C 8.81237.5 C 4.28 4.20

2.451 10.205

2.418 10.083 4.19

2.327 9.768 4.30

4.38

2.13212.5 C 9.42012.5 C

2.386 9.972

12.07

50

12.83 10.152

1.74 3.075 4.391

2.186 9.208 12.30 9.749

40

2.055 8.548

4.53

Tris(2-hydroxyethyl)amine (1) 2,4,6-Trimethylbenzoic acid (0) 3-Trimethylsilylbenzene acid (0) 4-Trimethylsilylbenzoic acid (0) -Ureidopropionic acid (0) DL-Valine (1) (0)

8.290

2.320 10.413

8.173

8.067

4.514

4.505 2.29712.5 C 10.06412.5 C

7.963 3.325 4.142 4.270 4.497

7.861 3.391 4.116 4.230 4.490

7.762 3.448 4.089 4.192 4.487 2.296 9.719

7.666 3.498 4.060 4.155 4.486

7.570 3.541 4.029 4.119 4.486 2.29237.5 C 9.40537.5 C

7.477 3.577 3.996 4.084 4.488

7.299

4.500 2.310 9.124

8.71

8.72

SECTION 8

TABLE 8.4 Indicators for Aqueous Acid–Base Titrations

Table 8.4 lists selected common indicators. The table is arranged according to function over increasing pH range or transition interval given (third column). Note that this range may vary appreciably from one observer to another, and that it is also affected by ionic strength, temperature, and illumination. The values given should therefore be considered to be approximate. These values refer to solutions having low ionic strengths and a temperature of about 25 C. In the fourth column the pKA (log KA) of the indicator as determined spectrophotometrically is listed. In the fifth and sixth columns, the wavelength of maximum absorption is given for the acidic and basic forms of the indicator, respectively. The lower to higher pH color change is given in the last column. The abbreviations used to describe the colors of the two forms of the indicator are as follows: B, Blue

P, Purple

C, Colorless

R, Red

G, Green

V, Violet

O, Orange OBr, Orange-brown

Y, Yellow

max, nm Indicator Cresol red (acid range) Cresol purple (acid range) Thymol blue (acid range) Tropeolin OO 2,6-Dinitrophenol 2,4-Dinitrophenol Methyl yellow Methyl orange Bromophenol blue Bromocresol green Methyl red Chlorophenol red Bromocresol purple Bromophenol red p-Nitrophenol Bromothymol blue Neutral red Phenol red

Chemical name

pH range

pKA

Acid Base

Color change

o-Cresolsulfonephthalein

0.2–18

R–Y

m-Cresolsulfonephthalein

1.2–2.8

1.51 533

Thymolsulfonephthalein

1.2–2.8

1.65 544

Diphenylamino-p-benzene sodium sulfonate 2,6-Dinitrophenol 2,4-Dinitrophenol Dimethylaminoazobenzene Dimethylaminoazobenzene sodium sulfonate Tetrabromophenolsulfonephthalein

1.3–3.2

2.0

527

R–Y

2.4–4.0 2.5–4.3 2.9–4.0 3.1–4.4

3.69 3.90 3.3 508 3.40 522

464

C–Y C–Y R–Y R–O

3.0–4.6

3.85 436

592

Y–BV

4.0–5.6

4.68 444

617

Y–B

R–Y 430

R–Y

Tetrabromo-m-cresolsulfonephthalein o-Carboxybenzeneazodimethylaniline Dichlorophenolsulfonephthalein Dibromo-o-cresolsulfonephthalein

4.4–6.2

4.95 530

427

R–Y

5.4–6.8 5.2–6.8

6.0 6.3

433

573 591

Y–R Y–P

Dibromophenolsulfonephthalein p-Nitrophenol Dibromothymolsulfonephthalein

5.2–6.8 5.3–7.6 6.2–7.6

7.15 320 7.1 433

574 405 617

Y–R C–Y Y–B

Aminodimethylaminotoluphenazonium chloride Phenolsulfonephthalein

6.8–8.0

7.4

6.4–8.0

7.9

R–Y 433

558

Y–R

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

8.73

TABLE 8.4 Indicators for Aqueous Acid–base Titrations (continued ) max, nm Indicator

Chemical name

pH range

pKA

Color Acid Base change

m-Nitrophenol Cresol red m-Cresol purple Thymol blue Phenolphthalein -Naphtholbenzein

m-Nitrophenol o-Cresolsulfonephthalein m-Cresolsulfonephthalein Thymolsulfonephthalein Phenolphthalein -Naphtholbenzein

6.4–8.8 7.2–8.8 7.6–9.2 8.0–9.6 8.0–10.0 9.0–11.0

8.3 8.2 434 8.32 8.9 430 9.4

570 572 580 596 553

C–Y Y–R Y–P Y–B C–R Y–B

Thymolphthalein Alizarin yellow

Thymolphthalein 5-(p-Nitrophenylazo)salicylic acid, Na salt p-Sulfobenzeneazoresorcinol 2,4,6-Trinitrophenylmethylnitroamine

9.4–10.6 10.0–12.0

10.0 11.16

598

C–B Y–V

Tropeolin O Nitramine

11.0–13.0 10.8–13.0

Y–OBr C–OBr

8.74

BUFFER SOLUTIONS TABLE 8.5 National Institute of Standards and Technology (formerly National Bureau of Standards U.S). Reference PH Buffer Solutions.

Temperature C

Secondary standard 0.05 M Potassium tetraoxalate

Potassium hydrogen tartrate (saturated at 25 C)

0 5 10 15 20 25 30 35 38 40 45 50 55 60 70 80 90 95

1.666 1.668 1.670 1.672 1.675 1.679 1.683 1.688 1.691 1.694 1.700 1.707 1.715 1.723 1.743 1.766 1.792 1.806

3.557 3.552 3.549 3.548 3.547 3.547 3.549 3.554 3.560 3.580 3.609 3.650 3.674

Dilution value pH1/2

0.186

0.049

0.05 M Potassium dihydrogen citrate 3.860 3.840 3.820 3.802 3.788 3.776 3.766 3.759 3.753 3.749

0.024

0.05 M Potassium hydrogen phthalate

0.025 M KH2PO4, 0.025 M Na2HPO4

0.0087 M KH2PO4, 0.0302 M Na2HPO4

0.01 M Na2B4O7

0.025 M NaHCO3, 0.025 M Na2CO3

4.003 3.999 3.998 3.999 4.002 4.008 4.015 4.024 4.030 4.035 4.047 4.060 4.075 4.091 4.126 4.164 4.205 4.227

6.984 6.951 6.923 6.900 6.881 6.865 6.853 6.844 6.840 6.838 6.834 6.833 6.834 6.836 6.845 6.859 6.877 6.886

7.534 7.500 7.472 7.448 7.429 7.413 7.400 7.389 7.384 7.380 7.373 7.367

9.464 9.395 9.332 9.276 9.225 9.180 9.139 9.102 9.081 9.068 9.038 9.011 8.985 8.962 8.921 8.885 8.850 8.833

10.317 10.245 10.179 10.118 10.062 10.012 9.966 9.925

0.052

0.080

0.070

0.01

0.079

Source: R. G. Bates, J. Res. Natl. Bur. Stand. (U.S.), 66A:179 (1962) and B. R. Staples and R. G. Bates, ibid, 73A: 37 (1969).

9.889 9.828

Secondary standard Ca(OH)2 (saturated at 25 C) 13.423 13.207 13.003 12.810 12.627 12.454 12.289 12.133 12.043 11.984 11.841 11.705 11.574 11.449

0.28

8.75

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.6 Compositions of National Institute of Standards and Technology. Standard pH Buffer Solutions Air weight of material per liter of buffer solution Standard

Weight, g

KH3(C2O4)2 · 2H2O, 0.05 M Potassium hydrogen tartrate, about 0.034 M Potassium hydrogen phthalate, 0.05 M Phosphate (solution 1) KH2PO4, 0.025 M Na2HPO4, 0.025 M Phosphate (solution 2) KH2PO4, 0.008665 M Na2HPO4, 0.03032 M Na2B4O7 · 10H2O, 0.01 M Carbonate NaHCO3, 0.025 M Na2CO3, 0.025 M Ca(OH)2, about 0.0203 M

12.61 Saturated at 25 C 10.12 3.39 3.53 1.179 4.30 3.80 2.10 2.65 Saturated at 25 C

Standard Reference pH Buffer Solutions The buffer value for the National Institute of Standards and technology (U.S.) reference pH buffer solutions is given below:

Buffer solution

KH tartrate

0.05 M KH2 citrate

Buffer value 

0.027

0.034

0.05 M KH phthalate

0.025 M KH2PO4, 0.025 M Na2HPO4

0.0087 M KH2PO4, 0.0302 M Na2HPO4

0.01 M Na2B4O7

0.016

0.029

0.016

0.020

0.025 M NaHCO3, 0.025 M Na2CO3

0.029

For the secondary pH reference standards, the buffer value is 0.070 for potassium tetraoxalate and 0.09 for calcium hydroxide. To prepare the standard pH buffer solutions recommended by the National Bureau of Standards (U.S.), the indicated weights of the pure materials in Table 8.6 should be dissolved in water of specific conductivity not greater than 5 micromhos. The tartrate, phthalate, and phosphates can be dried for 2 h at 110 C before use. Potassium tetraoxalate and calcium hydroxide need not be dried. Fresh-looking crystals of borax should be used. Before use, excess solid potassium hydrogen tartrate and calcium hydroxide must be removed. Buffer solutions pH 6 or above should be stored in plastic containers and should be protected from carbon dioxide with soda-lime traps. The solutions should be replaced

8.76

SECTION 8

within 2 to 3 weeks, or sooner if formation of mold is noticed. A crystal of thymol may be added as a preservative.

Buffer Solutions other than Standards The range of the buffering effect of a single weak acid group is approximately one pH unit on either side of the pKA. The ranges of some useful buffer systems are collected in Table 8.7. After all the components have been brought together, the pH of the resulting solution should be determined at the temperature to be employed with reference to standard reference solutions. Buffer components should be compatible with other components in the system under study; this is particularly significant for buffers employed in biological studies. Check tables of formation constants to ascertain whether metal-binding character exists. When there are two or more acid groups per molecule, or a mixture is composed of several overlapping acids, the useful range is larger. Universal buffer solutions consist of a mixture of acid groups which overlap such that successive pKA values differ by 2 pH units or less. The Prideaux–Ward mixture comprises phosphate, phenyl acetate, and borate plus HCl and covers the range from 2 to 12 pH units. The McIlvaine buffer is a mixture of citric acid and Na2HPO4 that covers the range from pH 2.2 to 8.0. The Britton–Robinson system consists of acetic acid, phosphoric acid, and boric acid plus NaOH and covers the range from pH 4.0 to 11.5. A mixture composed of Na2CO3, NaH2PO4, citric acid, and 2-amino-2-methyl-1,3-propanediol covers the range from pH 2.2 to 11.0.

TABLE 8.7 pH Values of Buffer Solutions for Control Purposes Materials* Glycine and HCl Citrate and HCl p-Toluenesulfonate and p-toluenesulfonic acid Formate and HCl Succinic acid and borax Phenyl acetate and HCl Acetate and acetic acid Succinate and succinic acid 2-(N-Morpholino)ethanesulfonic acid and NaOH 2,2-Bis(hydroxymethyl)-2,2,2 -nitrilotriethanol and HCl KH2PO4 and borax N-Tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid and NaOH KH2PO4 and Na2HPO4 N-2-Hydroxyethylpiperazine-N-2-ethanesulfonic acid and NaOH Triethanolamine and HCl Diethylbarbiturate (veronal) and HCl Tris(hydroxymethyl)aminomethane and HCl N-Tris(hydroxymethyl)methylglycine and HCl N,N-Bis(2-hydroxyethyl)glycine and HCl Borax and HCl Glycine and NaOH Ammonia (aqueous) and NH4Cl Ethanolamine and HCl

pH range 1.0–3.7 1.3–4.7 1.1–3.3 2.8–4.6 3.0–5.8 3.5–5.0 3.7–5.6 4.8–6.3 5.2–7.1 5.8–7.2 5.8–9.2 6.8–8.2 6.1–7.5 6.9–8.3 6.9–8.5 7.0–8.5 7.2–9.0

7.6–8.9 8.2–10.1 8.3–9.2 8.6–10.4

8.77

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

Borax and NaOH Carbonate and hydrogen carbonate Na2HPO4 and NaOH

9.4–11.1 9.2–11.0 11.0–12.0

General directions for the preparation of buffer solutions of varying pH but fixed ionic strength are given by Bates.* Preparation of McIlvaine buffered solutions at ionic strengths of 0.5 and 1.0 and Britton–Robinson solutions of constant ionic strength have been described by Elving et al.† and Frugoni,‡ respectively. * Bates, Determination of pH, Theory and Practice, Wiley, New York, 1964, pp. 121–122. † Elving, Markowitz, and Rosenthal, Anal. Chem., 28:1179 (1956). ‡ Frugoni, Gazz. Chim. Ital., 87:403 (1957).

REFERENCE ELECTRODES TABLE 8.8 Potentials of Reference Electrodes (in volts) as a Function of Temperature Liquid-junction potential included

Temp., C 0 5 10 15 20 25 30 35 38 40 45 50 55 60 70 80 90

Saturated 0.1 M KCl, 1.0 M KCl, 3.5 M KCl, KCl, 1.0 M KCl, 1.0 M KBr, calomel* calomel* calomel* calomel* Ag/AgCl† Ag/AgBr‡ 0.3367

0.2883

0.25918

0.3362 0.3361 0.3358 0.3356 0.3354 0.3351 0.3350 0.3345

0.2868

0.2556

0.2844 0.2830 0.2815

0.2520 0.2501 0.2481

0.2782

0.2448 0.2439

0.3315

0.2745

0.22737

0.3248

0.2702

0.2235

0.25387 0.2511 0.24775 0.24453 0.24118 0.2376 0.2355 0.23449

0.2083

1.0 M KI, Ag/AgI§

0.23655 0.23413 0.23142 0.22857 0.22557 0.22234 0.21904 0.21565

0.08128 0.07961 0.07773 0.07572 0.07349 0.07106 0.06856 0.06585

0.14637 0.14719 0.14822 0.14942 0.15081 0.15244 0.15405 0.15590

0.21208 0.20835 0.20449 0.20056 0.19649 0.18782 0.1787 0.1695

0.06310 0.06012 0.05704

0.15788 0.15998 0.16219

0.0251

* Bates et al., J. Res. Natl. Bur. Stand., 45:418 (1950). † Bates and Bower, J. Res. Natl. Bur. Stand., 53:283 (1954). ‡ Hetzer, Robinson, and Bates, J. Phys. Chem., 66:1423 (1962). § Hetzer, Robinson, and Bates, J. Phys. Chem., 68:1929 (1964).

Temp., C

125

150

1.0 M KCl, Ag/AgCl*

0.1330

1.0 M KBr, Ag/AgBr†

0.0048

175

200

0.1032

0.0708

0.0348 0.0051 0.054

0.0312

0.0612

* Greeley et al., J. Phys. Chem., 64:652 (1960). † Towns et al., J. Phys. Chem., 64:1861 (1960).

0.0951

225

250

275

0.090

8.78

SECTION 8

The values of several additional reference electrodes at 25 C are listed: Reference electrode Ag/AgCl, saturated KCl Ag/AgCl, 0.1 M KCl Hg/HgO, 1.0 M NaOH Hg/HgO, 0.1 M NaOH Hg/Hg2SO4, saturated K2SO4 (22 C) Hg/HgSO4, saturated KCl

Potential, V 0.198 0.288 0.140 0.165 0.658 0.655

TABLE 8.9 Potentials of Reference Electrodes (in volts) at 25 C for water–organic solvent mixtures Electrolyte solution of 1 M HCl

Solvent, wt % 5 10 20 30 40 45 50 60 70 80 82 90 94.2 98 99 100

Methanol, Ag/AgCl

Ethanol, Ag/AgCl

0.2153 0.2090

0.2146 0.2075 0.2003 0.1945

0.1968

2-Propanol, Ag/AgCl 0.2180 0.2138 0.2063

Acetone, Ag/AgCl 0.2190 0.2156 0.2079

Dioxane, Ag/AgCl

0.2031

0.1859

Ethylene glycol, Ag/AgCl 0.2190 0.2160 0.2101 0.2036 0.1972

Methanol, calomel

0.255

0.1818 0.1492 0.1135 0.0841

0.158

0.196

0.034

0.2104 0.1807

0.0659

0.216

0.0614

0.103 0.0081

0.53

0.1126 0.0014

0.0215 0.0099

0.2501

0.243

0.1635 0.1859 0.173 0.158 0.136

Dioxane, calomel

8.79

8.80

SECTION 8

ELECTRODE POTENTIALS TABLE 8.10 Potentials of Selected Half-Reactions at 25 C This table is a summary of oxidation–reduction half-reactions arranged in order of decreasing oxidation strength and is useful for selecting reagent systems. Abbreviations Used in the Table g, gas liq, liquid s, solid

Half-reaction F2(g)  2H  2e O3  2H  2e S2O82  2e Ag2  e H2O2  2H  2e MnO4  4H  3e Ce(IV)  e H5IO6  H  2e Bi2O4(bismuthate)  4H  2e BrO3  6H  5e MnO4  8H  5e PbO2  4H  2e Cl2  2e Cr2O72  14H  6e MnO2(s)  4H  2e O2(g)  4H  4e IO3  6H  5e Br2(liq)  2e ICl2  e VO2  2H  e HNO2  H  e NO3  3H  2e 2Hg2  2e Cu2  I  e Ag  e Hg22  2e Fe(III)  e O2(g)  2H  2e 2HgCl2  2e Hg2SO4(s)  2e H3AsO4  2H  2e Sb2O5  6H  4e I3  2e Cu  e VO2  2H  e Fe(CN)63  e Cu2  2e UO22  4H  2e BiO  2H  3e Hg2Cl2(s)  2e AgCl(s)  e

E, V  2HF  O2  H2O  2SO42  Ag  2H2O  MnO2(s)  2H2O  Ce(III) (in 1 M HClO4)  IO3  3H2O  2BiO  2H2O 1  2 Br2  3H2O  Mn2  4H2O  Pb2  2H2O  2Cl  2Cr3  7H2O  Mn2  2H2O  2H2O 1  2 I2  3H2O  2Br 1  2 I2  2Cl  VO2  H2O  NO(g)  H2O  HNO2  H2O  Hg22  CuI  Ag  2Hg  Fe2  H2O2  Hg2Cl2(s)  2Cl  2Hg  SO42  HAsO2  2H2O  2SbO  3H2O  3I  Cu  V3  H2O  Fe(CN)64  Cu  U4  2H2O  Bi  H2O  2Hg  2Cl  Ag  Cl

3.06 2.07 2.01 2.00 1.77 1.70 1.61 1.6 1.59 1.52 1.51 1.455 1.36 1.33 1.23 1.229 1.20 1.065 1.06 1.00 1.00 0.94 0.92 0.86 0.799 0.79 0.771 0.682 0.63 0.615 0.581 0.559 0.545 0.52 0.337 0.36 0.337 0.334 0.32 0.2676 0.2223

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.10 Potentials of Selected Half-Reactions at 25 C (continued) Half-reaction SbO  2H  3e CuCl32  e SO42  4H  2e Sn4  2e S  2H  2e TiO2  2H  e S4O62  2e AgBr(s)  e 2H  2e Pb2  2e Sn2  2e AgI(s)  e Mo3  3e N2  5H  4e Ni2  2e V3  e Co2  2e Ag(CN)2  e Cd2  2e Cr3  e Fe2  2e 2CO2  2H  2e H3PO3  2H  2e U4  e Zn2  2e Cr2  2e Mn2  2e Zr4  4e Ti3  3e Al3  3e Th4  4e Mg2  2e La3  3e Na  e Ca2  2e Sr2  2e K  e Li  e

E, V  Sb  H2O  Cu  3Cl  SO2(aq)  2H2O  Sn2  H2S(g)  Ti3  H2O  2S2O32  Ag  Br  H2  Pb  Sn  Ag  I  Mo  H2NNH3  Ni  V2  Co  Ag  2CN  Cd  Cr2  Fe  H2C2O4  H3PO2  H2O  U3  Zn  Cr  Mn  Zr  Ti  Al  Th  Mg  La  Na  Ca  Sr K  Li

0.212 0.178 0.17 0.154 0.141 0.10 0.08 0.071 0.0000 0.126 0.136 0.152 ca0.2 0.23 0.246 0.255 0.277 0.31 0.403 0.41 0.440 0.49 0.50 0.61 0.763 0.91 1.18 1.53 1.63  1.66 1.90 2.37 2.52 2.714 2.870 2.89 2.925 3.045

8.81

8.82

SECTION 8

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C The solvent systems in this table are listed below: A, acetonitrile and a perchlorate salt such as LiClO4 or a tetraalkyl ammonium salt B, acetic acid and an alkali acetate, often plus a tetraalkyl ammonium iodide C, 0.05 to 0.175 M tetraalkyl ammonium halide and 75% 1,4-dioxane D, buffer plus 50% ethanol (EtOH) Abbreviations Used in the Table M, molar MeOH, methanol Me, methyl PrOH, propanol

Bu, butyl Et, ethyl

EtOH, ethanol Compound

Solvent system

E1/2

Unsaturated aliphatic hydrocarbons Acrylonitrile Allene 1,3-Butadiene 1,3-Butadiyne 1-Buten-2-yne 1,4-Cyclohexadiene Cyclohexene 1,3,5,7-Cyclooctatetraene Diethyl fumarate Diethyl maleate 2,3-Dimethyl-1,3-butadiene Dimethylfulvene Diphenylacetylene 1,1-Diphenylethylene Ethyl methacrylate 2-Methyl-1,3-butadiene 2-Methyl-1-butene 1-Piperidino-4-cyano-4-phenyl1,3-butadiene trans-Stilbene Tetrakis(dimethylamino)ethylene

C but 30% EtOH C A C C C A A B C B, pH 4.0 B, pH 4.0 A C C B C 0.1 N LiCl  25% EtOH A A

1.94 2.29 2.03 2.59 1.89 2.40 1.6 1.89 1.42 1.51 0.84 0.95 1.83 1.89 2.20 1.52 2.19 1.9 1.84 1.97

LiClO4 in dimethylformamide B A

0.16 1.51 0.75

Aromatic hydrocarbons Acenaphthene

Anthracene

A B C A B C

0.95 1.36 2.58 0.84 1.20 1.94

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

8.83

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Aromatic hydrocarbons (continued ) Azulene

A C

1,2-Benzanthracene 2,3-Benzanthracene Benzene 1,2-Benzo[a]pyrene Biphenyl

C A A A A B C A A C A A A A B C A B A A C A B C A B C A B A B A B C C A B C C A A C

Chrysene 1,2,5,6-Dibenzanthracene 1,2-Dihydronaphthalene 9,10-Dimethylanthracene 2,3-Dimethylnaphthalene 9,10-Diphenylanthracene Fluorene

Hexamethylbenzene Indan Indene 1-Methylnaphthalene

2-Methylnaphthalene

Naphthalene Pentamethylbenzene Phenanthrene

Phenylacetylene Pyrene trans-Stilbene Styrene 1,2,3,5-Tetramethylbenzene 1,2,4,5-Tetramethylbenzene Tetraphenylethylene

0.71 1.66, 2.26, 2.56 2.03, 2.54 0.54, 1.20 2.08 0.76 1.48 1.91 2.70 1.22 1.00, 1.26 2.57 0.65 1.08, 1.34 0.92 1.25 1.65 2.65 1.16 1.52 1.59, 2.02 1.23 2.81 1.24 1.53 2.46 1.22 1.55 2.46 1.34 1.72 1.28 1.62 1.23 1.68 2.46, 2.71 2.37 1.06, 1.24 1.51 2.26 2.35 1.50, 1.99 1.29 2.05

8.84

SECTION 8

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Aromatic hydrocarbons (continued) 1,4,5,8-Tetraphenylnaphthalene Toluene 1,2,3-Trimethylbenzene 1,2,4-Trimethylbenzene 1,3,5-Trimethylbenzene Triphenylene Triphenylmethane

A A A A A B A C

o-Xylene m-Xylene p-Xylene

A A A

1.39 1.98 1.58 1.41 1.50 1.90 1.46, 1.55 1.01, 1.68, 1.96 1.58, 2.04 1.58 1.56

Aldehydes Acetaldehyde Benzaldehyde Bromoacetaldehyde Chloroacetaldehyde Cinnamaldehyde Crotonaldehyde Dichloroacetaldehyde 3,7-Dimethyl-2,6-octadienal Formaldehyde 2-Furaldehyde

Glucose Glyceraldehyde Glycolaldehyde Glyoxal 4-Hydroxybenzaldehyde 4-Hydroxy-2-methoxybenzaldehyde

o-Methoxybenzaldehyde p-Methoxybenzaldehyde Methyl glyoxal

B, pH 6.8–13 McIlvaine buffer, pH 2.2 pH 8.5 pH 9.8 Ammonia buffer, pH 8.4 Buffer  EtOH, pH 6.0 B, pH 1.3–2.0 Ammonia buffer, pH 8.0 Ammonia buffer, pH 8.4 0.1 M Et4NI 0.05 M KOH  0.1 M KCl, pH 12.7 pH 1–8 pH 10 Phosphate buffer, pH 7 Britton–Robinson buffer, pH 5.0 Britton–Robinson buffer, pH 8.0 0.1 M KOH, pH 13 B, pH 3.4 Britton–Robinson buffer, pH 1.8 Britton–Robinson buffer, pH 6.8 McIlvaine buffer, pH 2.2 McIlvaine buffer, pH 5.0 McIlvaine buffer, pH 8.0 Britton–Robinson buffer, pH 1.8 Britton–Robinson buffer, pH 6.8 Britton–Robinson buffer, pH 1.8 Britton–Robinson buffer, pH 6.8 A, pH 4.5

1.89 0.96, 1.32 0.40 1.58, 1.82 1.06, 1.66 0.9, 1.5, 1.7 0.92 1.30 1.03, 1.67 1.56, 2.22 1.59 0.86, 0.07 pH 1.43 1.55 1.47 1.55 1.70 1.41 1.16 1.45 1.05 1.16, 1.36 1.47 1.02 1.49 1.17 1.48 0.83

8.85

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Aldehydes (continued) m-Nitrobenzaldehyde Phthalaldehyde 2-Propenal (acrolein) Propionaldehyde Pyrrole-2-carbaldehyde Salicylaldehyde

Trichloroacetaldehyde

Buffer  10% EtOH, pH 2.0 Buffer, pH 3.1 Buffer, pH 7.3 pH 4.5 pH 9.0 0.1 M LiOH, pH 13 0.1 M HCl  50% EtOH McIlvaine buffer, pH 2.2 McIlvaine buffer, pH 5.0 McIlvaine buffer, pH 8.0 Ammonia buffer, pH 8.4 0.1 M KCl  50% EtOH

0.28, 1.20 0.64, 1.07 0.89, 1.29 1.36 1.1 1.93 1.25 0.99, 1.23 1.20, 1.30 1.32 1.35, 1.66 1.55

Ketones Acetone Acetophenone

7H-Benz[de]anthracen-7-one Benzil Benzoin Benzophenone Benzoylacetone

Bromoacetone 2,3-Butanedione 3-Buten-2-one Butyrophenone D-Carvone Chloroacetone Coumarin Cyclohexanone cis-Dibenzoylethylene trans-Dibenzoylethylene Dibenzoylmethane

B, pH 9.3 C D  McIlvaine buffer, pH 4.9 D  McIlvaine buffer, pH 7.2 D  McIlvaine buffer, pH 1.3 0.1 N H2SO4  75% MeOH D  McIlvaine buffer, pH 1.3 D  McIlvaine buffer, pH 4.9 D  McIlvaine buffer, pH 1.3 D  McIlvaine buffer, pH 8.6 D  McIlvaine buffer, pH 1.3 D  McIlvaine buffer, pH 8.6 Buffer, pH 2.6 Buffer, pH 5.3 and pH 7.6 Buffer, pH 9.7 0.1 M LiCl 0.1 M HCl 0.1 M KCl 0.1 M NH4Cl  50% EtOH 0.1 M Et4NI  80% EtOH 0.1 M LiCl McIlvaine buffer, pH 2.0 McIlvaine buffer, pH 5.0 C D, pH 1 D, pH 11 D, pH 1 D, pH 11 D, pH 1.3 D, pH 11.3

1.52 2.46 1.33 1.58 1.08 0.96 0.27 0.50 0.90 1.49 0.94 1.36 1.60 1.68 1.72 0.29 0.84 1.42 1.55 1.71 1.18 0.95 1.11, 1.44 2.45 0.30 0.62, 1.65 0.12 0.57, 1.52 0.59 1.30, 1.62

8.86

SECTION 8

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Ketones (continued) 9,10-Dihydro-9-oxoanthracene 1,5-Diphenyl-1,5-pentanedione 1,5-Diphenylthiocarbazone Flavanone

Fluorescein

Fructose Girard derivatives of aliphatic ketones o-Hydroxyacetophenone p-Hydroxyacetophenone 1,2,3-Indantrione (ninhydrin)

-Ionone Isatin

4-Methyl-3,5-heptadien-2-one 4-Methyl-2,6-heptanedione 4-Methyl-3-penten-2-one 4-Phenyl-3-buten-2-one Phthalide Phthalimide Pulegone Quinalizarin Testosterone

D, pH 2.0 A D, pH 7.0 Acetate buffer  Me4NOH  50% 2-PrOH, pH 6.1 Acetate buffer  Me4NOH  50% 2-PrOH, pH 9.6 Acetate buffer, pH 2.0 Phthalate buffer, pH 5.0 Borate buffer, pH 10.1 0.02 M LiCl

0.93 2.10 0.6 1.30

pH 8.2 D, pH 5 D, pH 5 Britton–Robinson buffer, pH 2.5 Britton–Robinson buffer, pH 4.5 Britton–Robinson buffer, pH 6.8

1.52 1.36 1.46 0.67, 0.83 0.73, 1.01 0.10, 0.90, 1.20 1.35 1.59, 2.08

Britton–Robinson buffer, pH 9.2 C Phosphate buffer  citrate buffer, pH 2.9 Phosphate buffer  citrate buffer, pH 4.3 Phosphate buffer  citrate buffer, pH 5.4 A A D  McIlvaine buffer, pH 1.3 D  McIlvaine buffer, pH 11.3 D, pH 1.3 D, pH 8.6 0.1 M Bu4NI  50% dioxane pH 4.2 pH 9.7 C Phosphate buffer  1% EtOH, pH 8.0 D  Britton–Robinson buffer, pH 2.6 D  Britton–Robinson buffer, pH 5.8 D  Britton–Robinson buffer, pH 8.8

1.51 0.50 0.65 1.18, 1.44 1.76

0.3, 0.5 0.3, 0.5, 0.8 0.8 0.64 1.28 1.01 1.60 0.72 1.27 0.20 1.1, 1.5 1.2, 1.4 1.74 0.56 1.20 1.40 1.53, 1.79

8.87

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Quinones Anthraquinone

o-Benzoquinone 2,3-Dimethylnaphthoquinone 1,2-Naphthoquinone 1,4-Naphthoquinone

Acetate buffer  40% dioxane, pH 5.6 Phosphate buffer  40% dioxane, pH 7.9 Britton–Robinson buffer, pH 7.0 Britton–Robinson buffer, pH 9.0 D, pH 5.4 Phosphate buffer, pH 5.0 Phosphate buffer, pH 7.0 Britton–Robinson buffer, pH 7.0 Britton–Robinson buffer, pH 9.0

0.51 0.71 0.20 0.08 0.22 0.03 0.13 0.07 0.19

Acids Acetic acid Acrylic acid Adenosine-5-phosphoric acid 4-Aminobenzenesulfonic acid 3-Aminobenzoic acid Anthranilic acid Ascorbic acid Barbituric acid Benzoic acid Benzoylformic acid

Bromoacetic acid 2-Bromopropionic acid Crotonic acid Dibromoacetic acid Dichloroacetic acid 5,5-Diethylbarbituric acid Flavanol Folic acid Formic acid Fumaric acid

2,4-Hexadienedioic acid Iodoacetic acid Maleic acid

A pH 5.6 HClO4  KClO4, pH 2.2 0.05 M Me4NI pH 5.6 pH 5.6 Birtton–Robinson buffer, pH 3.4 Britton–Robinson buffer, pH 7.0 Borate buffer, pH 9.3 A Britton–Robinson buffer, pH 2.2 Britton–Robinson buffer, pH 5.5 Britton–Robinson buffer, pH 7.2 Britton–Robinson buffer, pH 9.2 pH 1.1 pH 2.0 C pH 1.1 pH 8.2 Borate buffer, pH 9.3 D, pH 5.6 D, pH 7.7 Britton–Robinson buffer, pH 4.6 0.1 M KCl HCl  KCl, pH 2.6 Acetate buffer, pH 4.0 Acetate buffer, pH 5.9 Acetate buffer, pH 4.5 pH 1 Britton–Robinson buffer, pH 2.0 Britton–Robinson buffer, pH 4.0 Britton–Robinson buffer, pH 6.0 Britton–Robinson buffer, pH 10.0

2.3 0.85 1.13 1.58 0.67 0.67 0.17 0.06 0.04 2.1 0.48 0.85, 1.26 0.98, 1.25 1.25 0.54 0.39 1.94 0.03, 0.59 1.57 0.00 1.25 1.40 0.73 1.66 0.83 0.93 1.20 0.97 0.16 0.70 0.97 1.11, 1.30 1.51

8.88

SECTION 8

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Acids (continued) Mercaptoacetic acid Methacrylic acid Nitrobenzoic acids Oxalic acid 2-Oxo-1,5-pentanedioic acid 2-Oxopropionic acid

Phenolphthalein

Picric acid

1,2,3-Propenetricarboxylic acid Trichloroacetic acid 3,4,5-Trihydroxybenzoic acid p-Aminophenol

o-Chlorophenol m-Chlorophenol p-Chlorophenol o-Cresol m-Cresol p-Cresol 1,2-Dihydroxybenzene 1,3-Dihydroxybenzene 1,4-Dihydroxybenzene o-Methoxyphenol m-Methoxyphenol p-Methoxyphenol 1-Naphthol 2-Naphthol 1,2,3-Trihydroxybenzene

B, pH 6.8 D  0.1 M LiCl Buffer  10% EtOH, pH 2.0 B, pH 5.4–6.1 HCl  KCl, pH 1.8 Ammonia buffer, pH 8.2 Britton–Robinson buffer, pH 5.6 Britton–Robinson buffer, pH 6.8 Britton–Robinson buffer, pH 9.7 Phthalate buffer, pH 2.5 Phthalate buffer, pH 4.7 D, pH 9.6 pH 4.2 pH 11.7 pH 7.0 Ammonia buffer, pH 8.2 Phosphate buffer, pH 10.4 Phosphate buffer, pH 2.9 Phosphate buffer, pH 8.8 Britton–Robinson buffer, pH 6.3 Britton–Robinson buffer, pH 8.6 Britton–Robinson buffer, pH 12.0 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 pH 5.6 A A Britton–Robinson buffer, pH 3.1 Britton–Robinson buffer, pH 6.5 Britton–Robinson buffer, pH 9.5

0.38 1.69 0.2, 0.7 1.80 0.59 1.30 1.17 1.22, 1.53 1.51 0.67 0.80 0.98, 1.35 0.34 0.36, 0.56, 0.96 2.1 0.84, 1.57 0.9, 1.6 0.50 0.1 0.14 0.04 0.16 0.63 0.73 0.65 0.56 0.61 0.54 0.35 0.61 0.23 0.46 0.62 0.41 0.74 0.82 0.35 0.10 0.10

Halogen compounds Bromobenzene 1-Bromobutane

A C C

1.98 2.32 2.27

8.89

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Halogen compounds (continued) C C

2.08 1.63

Tetrabromomethane

A C A C A C C C C A 0.5 M K2SO4 A C D  1% Na2SO3 C Acetate buffer, pH 4.0 C C C C C A C A C C

Tetraiodomethane

C

Tribromomethane ,,-Trichlorotoluene

C C

1.55, 1.60 1.29 1.72 0.78, 1.71 2.07 1.63 2.23 1.91 1.81 1.76 0.13 1.15, 1.47 2.10 1.45 1.48 0.23, 0.89 2.5 1.60 1.12, 1.53 0.8, 1.5 1.4, 1.7 1.72 1.67 2.12 1.63 0.3, 0.75, 1.49 0.45, 1.05, 1.46 0.64, 1.47 0.68, 1.65, 2.00

Bromoethane Bromomethane 1-Bromonaphthalene (also 2-bromonaphthalene) 3-Bromo-1-propene p-Bromotoluene Carbon tetrachloride Chlorobenzene Chloroform Chloromethane 3-Chloro-1-propene -Chlorotoluene p-Chlorotoluene N-Chloro-p-toluenesulfonamide 9,10-Dibromoanthracene p-Dibromobenzene 1,2-Dibromobutane Dibromoethane meso-2,3-Dibromosuccinic acid Dichlorobenzenes Dichloromethane Diiodomethane Hexabromobenzene Hexachlorobenzene Iodobenzene Iodoethane Iodomethane

Nitro and nitroso compounds 1,2-Dinitrobenzene

1,3-Dinitrobenzene 1,4-Dinitrobenzene

Phthalate buffer, pH 2.5 Borate buffer, pH 9.2 Phthalate buffer, pH 2.5 Borate buffer, pH 9.2 Phthalate buffer, pH 2.5 Borate buffer, pH 9.2

0.12, 0.32, 1.26 0.38, 0.74 0.17, 0.29 0.46, 0.68 0.12, 0.33 0.35, 0.80

8.90

SECTION 8

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Nitro and nitroso compounds (continued) Methyl nitrobenzoates

Buffer  10% EtOH, pH 2.0

p-Nitroacetophenone

Britton–Robinson buffer, pH 2.2 Britton–Robinson buffer, pH 10.0

o-Nitroaniline m-Nitroaniline

p-Nitroaniline o-Nitroanisole p-Nitroanisole 1-Nitroanthraquinone Nitrobenzene

Nitrocresols

Nitroethane

2-Nitrohydroquinone

Nitromethane

o-Nitrophenol

0.03 M LiCl  0.02 M benzoic acid in EtOH Britton–Robinson buffer, pH 4.3 Briton-Robinson buffer, pH 7.2 Britton–Robinson buffer, pH 9.2 pH 2.0 Acetate buffer, pH 4.6 Buffer  10% EtOH, pH 2.0 Buffer  10% EtOH, pH 2.0 Britton–Robinson buffer, pH 7.0 HCl  KCl  8% EtOH, pH 0.5 Phthalate buffer, pH 2.5 Borate buffer, pH 9.2 Britton–Robinson buffer, pH 2.2 Britton–Robinson buffer, pH 4.5 Britton–Robinson buffer, pH 8.0 Britton–Robinson buffer  30% MeOH, pH 1.8 Britton–Robinson buffer  30% MeOH, pH 4.6 Phosphate buffer  citrate buffer, pH 2.1 Phosphate buffer  citrate buffer, pH 5.2 Phosphate buffer  citrate buffer, pH 8.0 Britton–Robinson buffer  30% MeOH, pH 1.8 Britton–Robinson buffer  30% MeOH, pH 4.6 Britton–Robinson buffer  10% EtOH, pH 2.0 Britton–Robinson buffer  10% EtOH, pH 4.0 Britton–Robinson buffer  10% EtOH, pH 8.0 Britton–Robinson buffer  10% EtOH, pH 10.0

0.20 to 0.25 0.68 to 0.74 0.16, 0.61, 1.09 0.51, 1.40, 1.73 0.88 0.3, 0.8 0.5 0.7 0.36 0.5 0.29, 0.58 0.35, 0.64 0.16 0.16, 0.76 0.30 0.70 0.2 to 0.3 0.4 to 0.5 0.6 0.7 0.8 0.2 0.4 0.5 0.8 0.85 0.23 0.4 0.65 0.80

8.91

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Nitro and nitroso compounds (continued) m-Nitrophenol

p-Nitrophenol

1-Nitropropane

2-Nitropropane Nitrosobenzene 1-Nitroso-2-naphthol

N-Nitrosophenylhydroxylamine o-Nitrotoluene m-Nitrotoluene (also p-nitrotoluene) Tetranitromethane 1,3,5-Trinitrobenzene

Britton–Robinson buffer  10% EtOH, pH 2.0 Britton–Robinson buffer  10% EtOH, pH 4.0 Britton–Robinson buffer  10% EtOH, pH 8.0 Britton–Robinson buffer  10% EtOH, pH 10.0 Britton–Robinson buffer  10% EtOH, pH 2.0 Britton–Robinson buffer  10% EtOH, pH 4.0 Britton–Robinson buffer  10% EtOH, pH 8.0 Britton–Robinson buffer  30% MeOH, pH 1.8 Britton–Robinson buffer  30% MeOH, pH 8.6 Britton–Robinson buffer  30% MeOH, pH 8.0 McIlvaine buffer, pH 2.1 McIlvaine buffer, pH 5.1 McIlvaine buffer, pH 6.0 McIlvaine buffer, pH 8.0 D  buffer, pH 4.0 D  buffer, pH 7.0 D  buffer, pH 9.0 pH 2.0 Phthalate buffer, pH 2.5 Phthalate buffer, pH 7.4 Phthalate buffer, pH 2.5 Phthalate buffer, pH 7.4 pH 12.0 Phthalate buffer, pH 4.1 Borate buffer, pH 9.2

0.37 0.40 0.64 0.76 0.35 0.50 0.82 0.73 0.88 0.95 0.53 0.81 0.03 0.14 0.02 0.20 0.31 0.84 0.35, 0.66 0.60, 1.06 0.30, 0.53 0.58, 1.06 0.41 0.20, 0.29, 0.34 0.34, 0.48, 0.65

Heterocyclic compounds containing nitrogen Acridine Cinchonine 2-Furanmethanol 2-Hydroxyphenazine

D, pH 8.3 B, pH 3 Britton–Robinson buffer, pH 2.0 Britton–Robinson buffer, pH 5.8 Britton–Robinson buffer, pH 4.0

0.80, 1.45 0.90 0.96 1.38, 1.70 0.24

8.92

SECTION 8

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Heterocyclic compounds containing nitrogen (continued) 8-Hydroxyquinoline 3-Methylpyridine 4-Methylpyridine Phenazine Pyridine Pyridine-2-carboxylic acid Pyridine-3-carboxylic acid Pyridine-4-carboxylic acid Pyrimidine Quinoline-8-carboxylic acid Quinoxaline

B, pH 5.0 Phosphate buffer, pH 8.0 D  0.1 M LiCl D  0.1 M LiCl Phosphate buffer  citrate buffer, pH 7.0 Phosphate buffer  citrate buffer, pH 7.0 B, pH 4.1 B, pH 9.3 0.1 M HCl Britton–Robinson buffer, pH 6.1 pH 9.0 Citrate buffer, pH 3.6 Ammonia buffer, pH 9.2 pH 9 Phosphate buffer  citrate buffer, pH 7.0

1.12 1.18, 1.71 1.76 1.87 0.36 1.75 1.10 1.48, 1.94 1.08 1.14 1.39, 1.68 0.92, 1.24 1.54 1.11 0.66, 1.52

Azo, hydrazine, hydroxylamine, and oxime compounds Azobenzene Azoxybenzene Benzoin-1-oxime

Benzoylhydrazine Dimethylglyoxime Hydrazine Hydroxylamine Oxamide Phenylhydrazine Phenylhydroxylamine

Salicylaldoxime Thiosemicarbazide Thiourea

D, pH 4.0 D, pH 7.0 Buffer  20% EtOH, pH 6.3 Buffer, pH 2.0 Buffer, pH 5.6 Buffer, pH 8.2 0.13 M NaOH, pH 13.0 Ammonia buffer, pH 9.6 Britton–Robinson buffer, pH 9.3 Britton–Robinson buffer, pH 4.6 Britton–Robinson buffer, pH 9.2 Acetate buffer McIlvaine buffer, pH 2 0.13 M NaOH, pH 13.0 McIlvaine buffer  10% EtOH, pH 2 McIlvaine buffer  10% EtOH, pH 4–10 Phosphate buffer, pH 5.4 Borate buffer, pH 9.3 0.1 M sulfuric acid

0.20 0.50 0.30 0.88 1.08 1.67 0.30 1.63 0.09 1.42 1.65 1.55 0.19 0.36 0.68 0.33 0.061 pH 1.02 0.26 0.02

8.93

ELECTROLYTES, ELECTROMOTIVE FORCE, AND CHEMICAL EQUILIBRIUM

TABLE 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25 C (continued ) Compound

Solvent system

E1/2

Indicators and dyestuffs Brilliant Green Indigo carmine Indigo disulfonate Malachite Green G Metanil yellow Methylene blue Methylene green Methyl orange Morin Neutral red

HCl  KCl, pH 2.0 pH 2.5 pH 7.0 HCl  KCl, pH 2.0 Phosphate buffer  1% EtOH, pH 7.0 Britton–Robinson buffer, pH 4.9 Britton–Robinson buffer, pH 9.2 Phosphate buffer  1% EtOH, pH 7.0 Phosphate buffer  1% EtOH, pH 7.0 D, pH 7.6 Britton–Robinson buffer, pH 2.0 Britton–Robinson buffer, pH 7.0

0.2, 0.5 0.24 0.37 0.2, 0.5 0.51 0.15 0.30 0.12 0.51 1.7 0.21 0.57

Peroxide Ethyl peroxide

0.02 M HCl

0.2

SECTION 9

DATA USEFUL IN LABORATORY MANIPULATION AND ANALYSIS

COOLING MIXTURES . . . . . . . . . . . . . . . . . . . . . . Table 9.1 Cooling Mixtures Made from Dry Ice and Salts . Table 9.2 Dry Ice or Liquid Nitrogen Slush Baths . . . . . HUMIDIFICATION AND DRYING . . . . . . . . . . . . . . . Table 9.3 Humidity (%) Maintained by Saturated Solutions of Various Salts at Specified Temperatures . . . Table 9.4 Humidity (%) Maintained by Saturated Solutions of Common Salts at Specified Temperatures . . Table 9.5 Drying Agents . . . . . . . . . . . . . . . . . . SEPARATION METHODS . . . . . . . . . . . . . . . . . . . . Table 9.6 Solvents of Chromatographic Interest . . . . . . Table 9.7 Solvents Having the Same Refractive Index and the Same Density at 25 C . . . . . . . . . . Table 9.8 McReynolds’ Constants for Stationary Phases in Gas Chromatography . . . . . . . . . . . . .

9.1

. . . .

. . . .

. . . .

9.2 9.2 9.2 9.2

. . . .

9.3

. . . .

. . . .

9.3 9.4 9.5 9.5

. . . .

9.7

. . . .

9.10

. . . .

. . . .

. . . .

9.2

SECTION 9

COOLING MIXTURES Convenient cooling mixtures can be prepared in several ways. First, an inorganic salt may be mixed with finely shaved dry ice. Such a mixture can be used to maintain temperatures as shown in Table 9.1. TABLE 9.1 Cooling Mixtures Made from Dry Ice and Salts

Salt CaCl2 · 6H2O

NH4Cl NaBr MgCl2

Dry ice, g/100 g

Minimum temperature, C

41 81 123 143 25 66 85

9.0 21.5 40.3 55 15.4 28 34

A more common method for preparing a low temperature bath is to mix an organic substance with either dry ice or liquid nitrogen. Dry ice (CO2, 78 C) can be added in small lumps to the solvent until a slight excess of dry ice remains. Alternately, liquid nitrogen (N2, 196 C) can be poured into the solvent until a slush is formed that consists of the solid–liquid mixture at its melting point. TABLE 9.2 Dry Ice or Liquid Nitrogen Slush Baths

Substance Ethylene glycol 1,2-Dichlorobenzene Carbon tetrachloride Bromobenzene Methoxybenzene Chlorobenzene Bis(2-ethoxyethyl) ether N-Methylaniline p-Cymene

Temperature, C 13 17 22.9 31 37 45 44 57 68

Substance Acetone–CO2 Ethyl acetate 2-Butanone Hexane Methanol Carbon disulfide Bromoethane Pentane 2-Methylbutane

Temperature, C 77 84 87 95 98 112 119 130 160

HUMIDIFICATION AND DRYING A saturated aqueous solution in contact with an excess of a definite solid phase at a given temperature will maintain constant humidity in an enclosed space. Table 9.3 identifies a number of salts suitable for this purpose. The aqueous tension (in millimeters of Hg) of a solution at a given temperature is found by multiplying the decimal fraction of the humidity by the aqueous tension at 100% humidity for the specific temperature. For example, the aqueous tension of a saturated solution of NaCl at 20 C is 0.757  17.54  13.28 mmHg and at 80 C is 0.764  355.1  271.3 mmHg.

9.3

DATA USEFUL IN LABORATORY MANIPULATION AND ANALYSIS

TABLE 9.3 Humidity (%) Maintained by Saturated Solutions of Various Salts at Specified Temperatures Temperature, C Solid phase

10

20

25

97 93 85.0 84 75.7 75

98.0 97 92.5 84.3 80.7 75.3 73.8

66

65 57.7 54 52.9 42.8

K2Cr2O7 K2SO4 KNO3 KCl KBr NaCl NaNO3 KI NaNO2 Na2CrO4 · 4H2O NaBr · 2H2O Na2Cr2O7 · 2H2O Mg(NO3)2 · 6H2O K2CO3 · 2H2O NaI · 2H2O MgCI2 · 6H2O CaCl2 · 6H2O KF · 2H2O KC2H3O2 · 1.5H2O LiCl · H2O KOH

34 38

57.9 55 55 44 47 33 32.6

24 13 13

23 12 9

Aqueous tension at 100% humidity, mmHg

9.21

17.54

98 95 88 86 76 77

58 58 57 47

30

60

25.3 30

23.2

22.8 20 11 6

21.0

22.8

22.5 11.1 8

52 42 36.4 33 26 27.4 22 12 7

96 82 80.7 79.0 74.9 67.5 63.1 59.3 55.6 49.9 55.2 43

11 5

23.76

31.82

55.32

149.4

74.9 72.8 63.0 64.6

TABLE 9.4 Humidity (%) Maintained by Saturated Solutions of Common Salts at Specified Temperatures Solid phase KF KI (NH4)2SO4 BaCl2 · 2H2O NaF

80

96 88 81.7 79.6 74.7 71.5 66.8 61.5 61.8 52.4 53.6 49 40 32.3 32

33.0 29

96 91 84

40

Temperature, C 100 100 20–30 108 25 100

Humidity, % 22.9 56.2 81.1 75 90.2 96.6

79.5 79.3 76.4 65.5 60.8 58.9 56.2 50.0 56.0

355.1

TABLE 9.5 Drying Agents 9.4 Drying agent Al2O3 Ba(ClO4)2a BaO CaC2b CaCl2c CaH2d CaO CaSO4 Dow Desiccant 812e K2CO3 KOH LiAlH4f Mg(ClO4)2a MgO MgSO4 Molecular sieves 4X 5X 9.5% Na–Pb alloyd Na2SO4 P2O5 Silica gel Sulfuric acid a

Most useful for

c

Grams water removed per gram of desiccant

Regeneration, C

Hydrocarbons Inert gas streams Basic gases: hydrocarbons, aldehydes, alcohols Ethers Inert organics

0.002–0.005 0.6–0.8 0.0007–0.003

Hydrocarbons, ethers, amines, esters, higher alcohols Ethers, esters, alcohols, amines Most organic substances Most materials Most materials except acids and phenols Amines Hydrocarbons Gas streams All but acidic compounds Most organic compounds

1  105

0.0005–0.002 0.008 1–12

1.9 0.24 0.45 0.15–0.75

Difficult, 1000 225 No 158 Impossible Impossible 250 (high vacuum) 800 Not feasible

Molecules with effective diameter  4Å Molecules with effective diameter  5Å Hydrocarbons, ethers Ketones, acids, alkyl and aryl halides Gas streams; not suitable for alcohols, amines, ketones, or amines Most organic amines Air and inert gas streams

0.001 0.001 (For solvents only) 12 2  105

0.18 0.18 0.08 1.25 0.5

250 250 Impossible 150 Not feasible

0.002–0.07 0.003–0.008

0.2 Indefinite

200–350 Not feasible

May form explosive mixtures on contact with organic material. Explosive C2H2 formed. Drying action slow. d H2 formed. e Used for column drying of organic liquids. f Strong reductant. b

Residual water, mg H2O per liter of dry air (25 C)

0.1–0.2

0.01–0.003 0.005–0.07 (5–200 ppm)

0.2 0.17 0.12

175 (24 h) 140 1000

0.56 0.15 (1 H2O) 0.30 (2 H2O) 0.85

Impossible 250

0.31 0.07 0.16

0.01–0.9

Impossible

SEPARATION METHODS TABLE 9.6 Solvents of Chromatographic Interest (arranged in order of increasing solvent strength)

Solvent

9.5

Fluoroalkanes Pentane Hexane 2,2,4-Trimethylpentane Decane Cyclohexane Cyclopentane Diisobutylene 1-Pentene Carbon disulfide Carbon tetrachloride 1-Chlorobutane 1-Chloropentane o-Xylene Diisopropyl ether 2-Chloropropane Toluene 1-Chloropropane Chlorobenezene Benzene Bromoethane Diethyl ether Diethyl sulfide Chloroform

Boiling point, C

36 69 99 174 81 49 101 30 46 77 78 98 144 68 35 111 47 132 80 38 35 92 62

Solvent strength parameter e (SiO2)

0.0 0.0 0.05

0.14 0.14

0.25 0.38 0.26

e (Al2O3) 0.25 0.0 0.0 0.01 0.04 0.04 0.05 0.06 0.08 0.15 0.18 0.26 0.26 0.26 0.28 0.29 0.29 0.30 0.40 0.32 0.37 0.38 0.38 0 40

Viscosity, mN · s · m2 (20 C)

0.2415 C 0.31 0.50 0.93 0.98 0.44 0.240 C 0.36 0.97 0.43 0.58 0.81 0.3825 C 0.33 0.59 0.35 0.80 0.65 0.40 0.25 0.45 0.57

Refractive index (20 C) 1.25 1.358 1.375 1.392 1.412 1.426 1.407 1.411 1.371 1.626 1.466 1.402 1.412 1.505 1.369 1.378 1.497 1.389 1.525 1.501 1.424 1.353 1.443 1.443

UV cutoff, nm

210 210 215 210 210 210

380 265 220 225 290 220 225 286 225 280 218 290 245

9.6

TABLE 9.6 Solvents of Chromatographic Interest (continued )

Solvent Dichloromethane 4-Methyl-2-pentanone Tetrahydrofuran 1,2-Dichloroethane 2-Butanone 1-Nitropropane Acetone 1,4-Dioxane Ethyl acetate Methyl acetate 1-Pentanol Dimethyl sulfoxide Aniline Diethylamine Nitromethane Acetonitrile Pyridine 2-Butoxyethanol 1-Propanol 2-Propanol Ethanol Methanol Ethylene glycol Acetic acid Water

Boiling point, C 41 116 66 84 80 131 56 101 77 56 138 189 184 56 101 82 115 170 97 82 78 65 198 118 100

Solvent strength parameter e (SiO2)

0.47 0.49 0.38

0.50

e (Al2O3) 0.42 0.43 0.45 0.49 0.51 0.53 0.56 0.56 0.58 0.60 0.61 0.62 0.62 0.63 0.64 0.65 0.71 0.74 0.82 0.82 0.88 0.95 1.11 large large

Viscosity, mN · s · m2 (20 C) 0.44 0.4215 C 0.55 0.80 0.4215 C 0.80 25C 0.32 1.4415 C 0.45 0.4815 C 4.1 2.47 4.40 0.33 0.67 0.37 0.97 3.15 25C 2.25 2.50 1.20 0.59 21.8 1.23 1.00

Refractive index (20 C) 1.425 1.396 1.407 1.445 1.379 1.402 1.359 1.420 1.372 1.362 1.410 1.478 1.586 1.386 1.394 1.344 1.510 1.420 1.386 1.377 1.361 1.328 1.432 1.372 1.333

UV cutoff, nm 235 335 220 228 330 380 330 215 255 260 210 265 275 380 190 330 220 210 210 210 210 210 260 191

9.7

DATA USEFUL IN LABORATORY MANIPULATION AND ANALYSIS

TABLE 9.7 Solvents having the Same Refractive Index and the Same Density at 25 C Refractive index Solvent 1 Acetone Ethyl formate Ethanol 2,2-Dimethylbutane 2-Methylpentane Isopropyl acetate 3-Butanone Butyraldehyde Dipropyl ether Propyl acetate Propyl acetate Butyronitrile Ethyl propionate 1-Propanol Isobutyl formate 1-Chloropropane Butyl formate Methyl butyrate Butyl acetate 4-Methyl-2-pentanone 4-Methyl-2-pentanone 2-Methyl-1-propanol 2-Methyl-1-propanol 2-Butanol 2-Hexanone Pentanonitrile 2-Chlorobutane Butyric acid 1-Butanol 1-Chloro2-methylpropane 1-Chloro2-methylpropane Methyl methacrylate Triethylamine Butylamine Isobutyl butyrate 1-Nitropropane Pentyl acetate Pentyl acetate Dodecane 1-Chlorobutane Isopentanoic acid Dipropylamine 2-Pentanol 3-Methyl-1-butanol 3-Methyl-1-butanol Hexanonitrile

Solvent 2

Density, g/mL

1

2

1

2

Ethanol Methyl acetate Propionitrile 2-Methylpentane Hexane 2-Chloropropane Butyraldehyde Butyronitrile Butyl ethyl ether Ethyl propionate 1-Chloropropane 2-Methyl-2-propanol 1-Chloropropane 2-Pentanone 1-Chloropropane Butyl formate Methyl butyrate 2-Chlorobutane 2-Chlorobutane Pentanonitrile 1-Butanol Pentanonitrile 2-Hexanone 2,4-Dimethyl-3-pentanone 1-Butanol 2,4-Dimethyl-3-pentanone Isobutyl butyrate 2-Methoxyethanol 3-Methyl-2-pentanone

1.357 1.358 1.359 1.366 1.369 1.375 1.377 1.378 1.379 1.382 1.382 1.382 1.382 1.383 1.383 1.386 1.387 1.392 1.392 1.394 1.394 1.394 1.394 1.395 1.395 1.395 1.395 1.396 1.397

1.359 1.360 1.363 1.369 1.372 1.376 1.378 1.382 1.380 1.382 1.386 1.385 1.386 1.387 1.386 1.387 1.391 1.395 1.395 1.395 1.397 1.395 1.395 1.399 1.397 1.399 1.399 1.400 1.398

0.788 0.916 0.786 0.644 0.649 0.868 0.801 0.799 0.753 0.883 0.883 0.786 0.888 0.806 0.881 0.890 0.888 0.875 0.877 0.797 0.797 0.798 0.798 0.803 0.810 0.795 0.868 0.955 0.812

0.786 0.935 0.777 0.649 0.655 0.865 0.799 0.786 0.746 0.888 0.890 0.781 0.890 0.804 0.890 0.888 0.875 0.868 0.868 0.795 0.812 0.795 0.810 0.805 0.812 0.805 0.860 0.960 0.808

Isobutyl butyrate

1.397

1.399

0.872

0.860

Pentyl acetate 3-Methyl-2-pentanone 2,2,3-Trimethylpentane Dodecane 1-Chlorobutane Propionic anhydride 1-Chlorobutane Tetrahydrofuran Dipropylamine Tetrahydrofuran 2-Ethoxyethanol Cyclopentane 4-Heptanone Hexanonitrile 4-Heptanone 4-Heptanone

1.397 1.398 1.399 1.399 1.399 1.399 1.400 1.400 1.400 1.401 1.402 1.403 1.404 1.404 1.404 1.405

1.400 1.398 1.401 1.400 1.401 1.400 1.400 1.404 1.400 1.404 1.405 1.404 1.405 1.405 1.405 1.405

0.872 0.795 0.723 0.736 0.860 0.995 0.871 0.871 0.746 0.871 0.923 0.736 0.804 0.805 0.805 0.801

0.871 0.808 0.712 0.746 0.875 1.007 0.881 0.885 0.736 0.885 0.926 0.740 0.813 0.801 0.813 0.813

9.8

SECTION 9

TABLE 9.7 Solvents having the Same Refractive Index and the Same Density at 25 C (continued ) Refractive index Solvent 1

Solvent 2

1

Hexanonitrile Hexanonitrile 4-Heptanone 2-Ethoxyethanol 2-Heptanone 2-Heptanone 2-Heptanone 2-Pentanol 1-Pentanol 2-Methyl-1-butanol Isopentyl isopentanoate Dipentyl ether 2,4-Dimethyldioxane 2,4-Dimethyldioxane Diethyl malonate 3-Chloropentene 2-Octanone 2-Octanone 3-Octanone 3-Methyl-2-heptanone 3-Methyl-2-heptanone 1-Hexanol Dibutylamine Allylamine Butyrolactone Butyrolactone 2-Chloromethyl-2propanol N-Methylmorpholine 1,3-Propanediol Methyl salicylate Methyl salicylate 1-Chlorodecane Diethylene glycol Diethylene glycol

1-Pentanol 2-Methyl-1-butanol 1-Pentanol Pentanoic acid 1-Pentanol 2-Methyl-1-butanol Dipentyl ether 3-Isopropyl-2-pentanone Dipentyl ether Dipentyl ether Allyl alcohol 2-Octanone 3-Chloropentene Hexanoic acid Ethyl cyanoacetate Octanoic acid 1-Hexanol Octanonitrile 3-Methyl-2-heptanone 1-Hexanol Octanonitrile Octanonitrile Allylamine Methylcyclohexane 1,3-Propanediol Diethyl maleate Diethyl maleate

1.405 1.405 1.405 1.405 1.406 1.406 1.406 1.407 1.408 1.409 1.410 1.410 1.412 1.412 1.412 1.413 1.414 1.414 1.414 1.415 1.415 1.416 1.416 1.419 1.434 1.434 1.436

Dibutyl decanedioate Diethyl maleate Diethyl sulfide 1-Butanethiol Mesityl oxide Formamide Ethylene glycol diglycidyl ether Ethylene glycol diglycidyl ether Cyclohexanone 1-Amino-2-propanol Tetrahydrofurfuryl alcohol

Formamide

2-Methylmorpholine 2-Methylmorpholine Dipropylene glycol monoethyl ether 1-Amino-2-methyl2-Butylcyclohexanone 2-pentanol 2-Propylcyclohexanone 4-Methylcyclohexanol

Density, g/mL 2

1

2

1.408 1.409 1.408 1.406 1.408 1.409 1.410 1.409 1.410 1.410 1.411 1.414 1.413 1.415 1.415 1.415 1.416 1.418 1.416 1.416 1.418 1.418 1.419 1.421 1.438 1.438 1.438

0.801 0.801 0.813 0.926 0.811 0.811 0.811 0.804 0.810 0.815 0.853 0.799 0.935 0.935 1.051 0.932 0.814 0.814 0.830 0.818 0.818 0.814 0.756 0.758 1.051 1.051 1.059

0.810 0.815 0.810 0.936 0.810 0.815 0.799 0.808 0.799 0.799 0.847 0.814 0.932 0.923 1.056 0.923 0.814 0.810 0.818 0.814 0.810 0.810 0.758 0.765 1.049 1.064 1.064

1.436 1.438 1.438 1.438 1.441 1.445 1.445

1.440 1.438 1.442 1.442 1.442 1.446 1.447

0.924 1.049 0.836 0.836 0.862 1.128 1.128

0.932 1.064 0.831 0.837 0.850 1.129 1.134

1.446

1.447

1.129

1.134

1.446 1.446 1.446

1.448 1.448 1.450

0.951 0.951 1.043

0.943 0.961 1.050

1.449

1.453

0.904

0.901

1.452

1.454

0.923

0.908

9.9

DATA USEFUL IN LABORATORY MANIPULATION AND ANALYSIS

TABLE 9.7 Solvents having the Same Refractive Index and the Same Density at 25 C (continued ) Refractive index Solvent 1

Solvent 2

Carbon tetrachloride

4,5-Dichloro-1,3dioxolan-2-one N-Butyldiethanolamine Cyclohexanol D--Pinene trans-Decahydronaphthalene Propylbenzene p-Xylene Propylbenzene Toluene Phenyl 1-hydroxyphenyl 1,3-Dimorpholyl-2ether propanol Phenetole Pyridine 2-Furanmethanol Thiophene m-Cresol Benzaldehyde

1

2

Density, g/mL 1

2

1.459

1.461

1.584

1.591

1.461 1.464

1.465 1.468

0.965 0.855

0.968 0.867

1.490 1.490

1.493 1.494

0.858 0.858

0.857 0.860

1.491

1.493

1.081

1.094

1.505 1.524 1.542

1.507 1.526 1.544

0.961 1.057 1.037

0.978 1.059 1.041

McReynolds’ Constants The Kovats retention indices (R.I.) indicate where compounds will appear on a chromatogram with respect to unbranched alkanes injected with the sample. By definition, the R.I. for pentane is 500, for hexane is 600, for heptane is 700, and so on, regardless of the column used or the operating conditions, although the exact conditions and column must be specified, such as liquid loading, particular support used, and any pretreatment. For example, suppose that on a 20% squalane column at 100 C, the retention times for hexane, benzene, and octane are found to be 15, 16, and 25 min, respectively. On a graph of ln tR (naperian logarithm of the adjusted retention time) of the alkanes versus their retention indices, a R.I. of 653 for benzene is read off the graph. The number 653 for benzene (see the last line of Table 9.8 in the column headed “1” under “Reference compounds”) means that it elutes halfway between hexane and heptane on a logarithmic time scale. If the experiment is repeated with a dinonyl phthalate column, the R.I. for benzene is found to be 736 (lying between heptane and octane), which implies that dinonyl phthalate will retard benzene slightly more than squalane will; that is, dinonyl phthalate is slightly more polar than squalane by I  83 units (the entry in Table 9.8 for dinonyl phthalate in the column headed “1” under “Reference compounds”). The difference gives a measure of solute– solvent interaction due to all intermolecular forces other than London dispersion forces. The latter are the principal solute–solvent effects with squalane. Now the overall effects due to hydrogen bonding, dipole moment, acid–base properties, and molecular configuration can be expressed as  I  ax by cz du es where x  I for benzene (the column headed “1” in Table 9.8, intermolecular forces typical of aromatics and olefins), y  I for 1-butanol (the column headed “2” in Table 9.8, electron attraction typical of alcohols, nitriles, acids, and nitro and alkyl monochlorides, dichlorides and trichlorides), z  I for 2-pentanone (the column headed “3” in Table 9.8, electron repulsion typical of ketones, ethers, aldehydes, esters, epoxides, and dimethylamino derivatives), u  I for 1-nitropropane (the column headed “4” in Table 9.8, typical of nitro and nitrile derivatives), and s  I for pyridine (or dioxane) (the column headed “5” in Table 9.8).

9.10

TABLE 9.8 McReynolds’ Constants for Stationary Phases in Gas Chromatography The McReynolds’ constants listed are differences in retention index units between the reference compound run on squalane and on the other phases listed. The last entry in the table shows the absolute retention indices for the reference compounds on squalane. Reference compounds are (1) benzene, (2) 1-butanol, (3) 2-pentanone, (4) 1 nitropropane, and (5) pyridine. (Note that Rohrschneider’s constants are based on these reference compounds and may differ slightly from the McReynolds’ constants. The reference compounds for Rohrschneider’s constants are (1) benzene, (2) ethanol, (3) 2-butanone, (4) nitromethane, and (5) pyridine.) The minimum temperature is that at which normal gas–liquid chromatography (GLC) behavior is expected. Below that temperature, the phase will be a solid or an extremely viscous gum. The maximum temperature is that above which the bleed rate will be excessive.

Liquid phase Squalane Paraffin oil Apolane-87

Apiezon L SE 30 OV-10l OV-73 SE 54 OV-3 Dexsil 300 Kel F Wax Apiezon H

Chemical type

Similar liquid phases

Temperature, C Minimum

Maximum

Reference compounds 1

2

3

4

5

Sum

(2,6,10,15,19,23Hexamethyl)tetracosane

20

150

0

0

0

0

0

0

(24,24-Diethyl-19,29dioctadecyl)heptatetracontane

30

280

9 21

5 10

2 3

6 12

11 25

33 71

50 50 50

250 350 350

32 15 17

22 53 57

15 44 45

32 64 67

42 41 43

143 217 229

0

325

32

72

65

98

67

334

50 0

300 350

33 44

72 86

66 81

99 124

67 88

337 423

50

500 150 300

47 55 59

80 67 86

103 148 114 143 81 151

96 116 129

474 495 506

Poly(dimethylsiloxane) Poly(diphenyldimethylsiloxane), 5%:95% Poly(diphenylvinyldimethylsiloxane), 5%:1%:94% Poly(diphenyldimethylsiloxane), 10%:90% Poly(carboranemethylsiloxane)

SP-2100, SF 96 OV-1, DC 200, DC 410 SE 52

Dexsil 400 OV-7 Di(2-ethylhexyl) sebacate Diisodecyl adipate Decyl octyl adipate Bis(2-ethylhexyl)tetrachlorophthalate Diisodecyl phthalate Dinonyl phthalate OV-11 Dioctyl phthalate Hallcomid M-18 OV-17 Dexsil 410 UCON LB-550-X Span 80 OV-22 Polypropylene glycol Didecyl phthalate OV-25

9.11

Polyphenyl ether OS-138 (6 rings) Neopentyl glycol sebacate Squalene UCON 50-HB-280X Tricresyl phosphate

Carborane and methylphenylsilicone Poly(diphenyldimethylsiloxane), 20%:80%

Poly(diphenyldimethylsiloxane), 35%:65%

DC 550

DC 710

Poly(diphenyldimethylsiloxane), 50%:50% Carborane and methylcyanoethylsilicone

Poly(diphenyldimethylsiloxane), 65%:35%

Poly(diphenyldimethylsiloxane), 75%:25%

HI-EFF-3CP

50 20

500 350

72 69

108 118 166 113 111 171

123 128

587 592

0

125 175

0

150

72 71 79 112

168 171 179 150

180 185 193 168

125 128 134 181

653 668 704 734

0 20 0

175 150 350

84 83 107

173 137 218 183 147 231 149 153 228

155 159 190

767 803 827

20 40 0

125 150 325

92 79 119

186 150 236 268 130 222 158 162 243

167 146 202

831 845 884

50

500

72

286 174 249

171

952

0 15 0

200 150 350

118 97 160

271 158 243 266 170 216 188 191 283

206 268 253

996 1017 1075

0 10 0

150 175 350

128 136 178

294 173 264 255 213 320 204 208 305

226 235 280

1085 1159 1175

0

225

182

233 228 313

293

1249

50 0 0 20

225 100 200 125

172 152 177 176

327 341 362 321

326 344 302 299

1394 1404 1419 1420

108 113 119 123

225 328 227 250

344 329 351 374

9.12

TABLE 9.8 McReynolds’ Constants for Stationary Phases in Gas Chromatography (continued )

Liquid phase Sucrose acetate isobutyrate QF-1 OV-210 OV-215 UCON 50-HB-2000 Triton X-100 UCON 50-HB-5100 Siponate DS-10 Tween 80 XE-60 OV-225 Neopentyl glycol adipate UCON 75-H-90000 Triton X-305 Neopentyl glycol succinate Igepal CO 990 Carbowax 20M Epon 1001 Carbowax 4000 Ethylene glycol isophthalate Ethylene glycol adipate Butane-1,4-diol succinate Phenyldiethanolamine succinate

Chemical type

Poly(trifluoropropylsiloxane) Poly(trifluoropropylmethylsiloxane) Emulphor ON-870

Similar liquid phases

SP-2401, FS 1265 XE 6O

Poly(cyanoethylphenylmethylsiloxane) Poly(cyanopropylphenylmethylsiloxane) HI-EFF-3AP Igepal CO-880 HI-EFF-3BP Poly(ethylene glycol)

FFAP, SP-2300

HI-EFF-2EP HI-EFF-2AP HI-EFF-4BP HI-EFF-10BP

Temperature, C Minimum

Maximum

0 0 0

Reference compounds 1

2

200 250 275

172 144 146

0 0 0 0 0 0

275 200 200 200 200 150

0 0 50 100 0 50 100 25 50 60 100 100 50 0

3

5

Sum

330 251 378 233 355 463 238 358 468

295 305 310

1426 1500 1520

149 202 203 214 99 227

240 394 399 418 569 430

478 392 402 421 344 438

315 341 362 375 388 396

1545 1582 1634 1706 1720 1747

250

204

381 340 493

367

1785

265 225 200 200 230 200 275 225 200 225 225 225 200

228 232 255 262 272 298 322 284 325 326 372 369 386

369 421 452 467 469 508 536 489 551 508 576 591 555

386 424 406 430 474 475 510 601 520 561 617 629 654

1813 1849 1882 1961 2120 2166 2308 2319 2353 2427 2673 2207 2741

363 253 268 278 320 283

338 311 299 314 366 345 368 406 375 425 453 457 472

4

492 461 470 488 539 540 572 539 582 607 655 661 674

Diethylene glycol adipate

HI-EFF-1AP, LAC- 1-R-296, SP- 2330

Carbowax 1540 Hyprose SP-80 SILAR-7CP ECNSS-M EGSS-X Ethylene glycol phthalate SILAR-9CP SILAR-10C Diethylene glycol succinate Tetrahydroxyethylenediamine Tetracyanoethylated pentaerythritol Ethylene glycol succinate 1,2,3,4-Tetrakis(2-cyanoethoxy)butane 1,2,3,4,5,6-Hexakis (2 cyanoethoxy)cyclohexane 1,2,3-Tris(2-cyanoethoxy)propane N,N-Bis(2-cyanoethyl)formamide OV-275

HI-EFF-2GP SP-2340 HI-EFF-1BP, LAC-3-R-728 THEED

HI-EFF-2BP

Dicyanoallylsilicone

Absolute retention index values on squalane for reference compounds

25

275

378

603 460 665

658

2764

50 0 0 30 90 100 0 25 20

175 175 250 200 200 200 250 275 200

371 336 440 421 484 453 489 523 499

639 742 638 690 710 697 725 757 751

666 639 844 803 831 816 910 942 840

641 727 673 732 778 872 778 801 860

2770 2936 3200 3227 3388 3410 3536 3682 3543

0 30

150 175

463 526

942 626 801 782 677 920

893 837

3725 3742

100

200

537

787 643 903

889

3759

110 125

200 150

617 567

860 773 1048 941 825 713 978 901

4239 3984

0 0

175 125

593 690

857 752 1028 915 4145 991 853 1110 1000 4644

25

250

781

1006 885 1177 1089 4938

453 492 605 581 585 602 631 659 593

653 590 627 652

699

9.13

SECTION 10

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

POLYMERS . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Table 10.1 Plastic Families . . . . . . . . . . . . . . . . . FORMULAS AND KEY PROPERTIES OF PLASTIC MATERIALS Table 10.2 Properties of Commercial Plastics . . . . . . . FORMULAS AND ADVANTAGES OF RUBBERS . . . . . . . . . Table 10.3 Properties of Natural and Synthetic Rubbers . . CHEMICAL RESISTANCE . . . . . . . . . . . . . . . . . . . . . . Table 10.4 Resistance of Selected Polymers and Rubbers to Various Chemicals at 20 C . . . . . . . . . . Table 10.5 Common Abbreviations used in Polymer Chemistry . . . . . . . . . . . . . . . . . . . . GAS PERMEABILITY . . . . . . . . . . . . . . . . . . . . . . . . Table 10.6 Gas Permeability Constants (1010 P) at 25 C for Polymers and Rubbers . . . . . . . . . . . Table 10.7 Vapor Permeability Constants (1010 P) at 35 C for Polymers . . . . . . . . . . . . . . FATS, OILS, AND WAXES . . . . . . . . . . . . . . . . . . . . . . Table 10.8 Constants of Fats and Oils . . . . . . . . . . . Table 10.9 Constants of Waxes . . . . . . . . . . . . . . .

10.1

. . . . . . .

. . . . . . .

10.2 10.7 10.9 10.24 10.60 10.64 10.65

. .

10.65

. . . .

10.67 10.70

. .

10.70

. . . .

10.73 10.73 10.73 10.76

. . . .

10.2

SECTION 10

POLYMERS General Polymers are macromolecules that result from combinations of individual building blocks called monomer molecules. Most polymers are regular structures in which a single unit repeats many times. This produces a range of macromolecules that have similar structures and molecular weights. The ensemble of molecules typically exhibit average molecular weights but have characteristic properties. Polymerization of ethylene, CH2 ¨ CH2, results in polyethylene, ( ˆ CH2 ˆ CH2 ˆ )n such that “n” is a range of values. If the average chain possesses 1000 monomer units, chains having values of n such as 998, 999, 1001, 1002, etc. will be present as well. There will be more such chains near the average value and fewer or none when n is far from the average value. In some polymers, long segments of linear polymer chains are oriented in a regular manner with respect to one another. Such polymers have many of the physical characteristics of crystals and are said to be crystalline. Polymers that have polar functional groups show a greater tendency to be crystalline. Orientation is aided by alignment of dipoles on different chains. Van der Waals’ interactions between long hydrocarbon chains may provide sufficient total attractive energy to account for a high degree of regularity within the polymers. Irregularities such as branch points, co-monomer units, and cross-links lead to amorphous polymers. These have less regular structures and typically do not have true melting points. Instead, they have glass transition temperatures at which the rigid and glass-like material becomes a viscous liquid as the temperature is raised. Elastomers. Elastomer is a generic name for polymers that exhibit rubber-like elasticity. Elastomers are soft yet sufficiently elastic that they can usually be stretched several hundred percent under tension. When the stretching force is removed, they quickly retract and recover their original dimensions. Polymers that soften or melt and then solidify and regain their original properties on cooling are called thermoplastic. A thermoplastic polymer is usually a single strand of linear polymer with few if any cross-links. Thermosetting Polymers. Polymers that soften or melt on warming and then become infusible solids are called thermosetting. The term implies that thermal decomposition has not taken place. Thermosetting plastics contain a cross-linked polymer network that extends through the final material, making it stable to heat and insoluble in organic solvents. Many molded plastics are shaped while molten and are then heated further to become rigid solids of desired shapes. Synthetic Rubbers. Synthetic rubbers are polymers with rubber-like characteristics that are prepared from dienes or olefins. Rubbers with special properties can also be prepared from other polymers, such as polyacrylates, fluorinated hydrocarbons, and polyurethanes. Structural Differences. Polymers exhibit structural differences resulting from the type of monomer used, the polymerization method employed, and other factors. A linear polymer consists of long segments of single strands that are oriented in a regular manner with respect to one another. Branched polymers have substituents attached to the repeating units that extend the polymer laterally. When these units participate in chain propagation and link together chains, a cross-linked polymer is formed. A ladder polymer results when repeating units have a tetravalent structure such that a polymer consists of two backbone chains regularly cross-linked at short intervals.

10.3

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

Generally polymers involve bonding of the most substituted carbon of one monomeric unit to the least substituted carbon atom of the adjacent unit in a head-to-tail arrangement. An example is the formation of polypropylene from propylene. This is shown for three monomer units. The wavy lines indicate that more monomers would lead to extended chains. + H 3C

+ H3C

H3C

CH 3

CH 3

CH 3

Substituents appear on alternate carbon atoms. Tacticity refers to the configuration of substituents relative to the backbone axis. In an isotactic arrangement, substituents are on the same plane of the backbone axis; that is, the configuration at each chiral center is identical.

H3C

H H 3C

H H 3C

H

In a syndiotactic arrangement, the substituents are in an ordered alternating sequence, appearing alternately on one side and then on the other side of the chain, as shown for a segment of a vinyl chloride polymer. If the sidechains are not in any particular order with respect to each other (random), the polymer is said to be atactic.

H Cl

Cl Cl

H

H

Copolymerization. Copolymerization occurs when a mixture of two or more monomer types polymerizes so that each kind of monomer enters the polymer chain. The fundamental structure resulting from copolymerization depends on the nature of the monomers and the relative rates of monomer reactions with the growing polymer chain. A tendency toward alternation of monomer units is common. Random copolymerization is known but it is rather unusual. + A

+ B

+ A

B

A

B

A

B

In graft copolymers the chain backbone is composed of one kind of monomer and the branches are made up of another kind of monomer. The structure of a block copolymer consists of a homopolymer attached to chains of another homopolymer. In either case, cis or trans (Z or E ) double bond configurations around any double bond not involved in the polymerization will normally be unaltered. X X X X X X X X Y

Y Y

Y

Y Y

Y

Y Y

Schematic of a graft copolymer

A

A

A

A

B

B

B

Schematic of a block copolymer

B

10.4

SECTION 10

Dendrimers A relatively recent development in polymer chemistry is the family of compounds known as dendrimers. The term derives from the Greek dendra meaning tree. Tree-like structures of this general type have also been referred to as arborols. Dendrimers differ from typical polymers in that they radiate from a central unit or core rather than being either linear or planar. Dendrimers are built up using a “generational” structure in discrete synthetic steps. As a result, the product is nearer to being a single compound than is a typical polymer. A typical dendrimer consists of a multifunctional core unit. Each functional group of the core unit is elaborated by a further molecular unit, often referred to as a “dendritic wedge.” The core unit is usually designated “generation 0” and additional units radiating from it or prior units are designated as higher generations, that is, generation 1, generation 2, etc. When the synthesis begins at the core and radiates outward, it is called a divergent synthesis. Alternately, synthesis may begin at the outside and terminate with a core unit. The more common divergent method is illustrated in the following scheme. 1,3,5Tricarboxybenzene (trimesic acid) serves as the core or generation 0. It could be functionalized by converting it into the tris(acid chloride). Reaction with the secondary amine of diethanolamine would give the tris(amide) hexahydroxy compound shown here. This structure represents generations 0 and 1. Treatment with an appropriately substituted benzyl chloride could lead to the hexaether that comprises generations 0, 1, and 2. There are now a dozen “Y” groups that could be further functionalized in going to generation 3. A difficulty is that the functional or protecting groups present at each stage must be compatible with the chemistry used to make the connections.

HO

HOOC

OH

COOH

HO

OH N CO

O C

N

+ 3 HN COOH

OC

OH

OH

OH

N

OH

Y

Y

Y

Y

Y

Y

Y

O

O

N

O N

O C

Y

CO

+ 6 Y OC

O

Cl

Y

O

N

Y

O

Y

Y

Y

A second issue is that when subsequent generations involve sterically demanding structural units, incomplete substitution may occur. Thus, in the final structure shown, five

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.5

benzyl ethers might form, rather than six, owing to steric crowding. This would introduce a defect in the dendrimer structure. Indeed, some molecules might possess all six benzyl ethers whereas others might lack one or even two. It must be possible to manipulate the substituents designated “Y” in the presence of ether and amide groups to further extend the dendrimer. Novel dendrimers have novel and unique properties that make them promising candidates for use in the development of nanoscale devices and in drug delivery systems.

Additives to Polymers Antioxidants. Antioxidants markedly retard the rate of autoxidation throughout the useful life of the polymer. Chain-terminating antioxidants have a reactive ˆ NH or ˆ OH functional group and include compounds such as secondary aryl amines or hindered phenols. They function by transfer of hydrogen to free radicals, principally to peroxy radicals. Butylated hydroxytoluene is a widely used example. Peroxide-decomposing antioxidants destroy hydroperoxides, the sources of free radicals in polymers. Phosphites and thioesters such as tris(nonylphenyl) phosphite, distearyl pentaerythritol diphosphite, and dialkyl thiodipropionates are examples of peroxidedecomposing antioxidants. Antistatic Agents. External antistatic agents are usually quaternary ammonium salts of fatty acids and ethoxylated glycerol esters of fatty acids that are applied to the plastic surface. Internal antistatic agents are compounded into plastics during processing. Carbon blacks provide a conductive path through the bulk of the plastic. Other types of internal agents must bloom to the surface after compounding in order to be active. These latter materials are ethoxylated fatty amines and ethoxylated glycerol esters of fatty acids, which often must be individually selected to match chemically each plastic type. Antistatic agents require ambient moisture to function. Consequently their effectiveness is dependent on the relative humidity. They provide a broad range of protection at 50% relative humidity. Much below 20% relative humidity, only materials that provide a conductive path through the bulk of the plastic to ground (such as carbon black) will reduce electrostatic charging. Chain-Transfer Agents. Chain-transfer agents are used to regulate the molecular weight of polymers. These agents react with the developing polymer and interrupt the growth of a particular chain. The products, however, are free radicals that are capable of adding to monomers and initiating the formation of new chains. The overall effect is to reduce the average molecular weight of the polymer without reducing the rate of polymerization. Branching may occur as a result of chain transfer between a growing but rather short chain with another and longer polymer chain. Branching may also occur if the radical end of a growing chain abstracts a hydrogen atom from a carbon atom four or five carbons removed from the end. Thiols are commonly used as chain-transfer agents. Coupling Agents. Coupling agents are molecular bridges between the interface of an inorganic surface (or filler) and an organic polymer matrix. Titanium-derived coupling agents interact with the free protons at the inorganic interface to form organic monomolecular layers on the inorganic surface. The titanate-coupling-agent molecule has six functions: (RO)m ˆ Tiˆ (O ˆ Y ˆ R1 ˆ Z)n

10.6

SECTION 10

where Type

m

n

Monoalkoxy Coordinate Chelate

1 4 1

3 2 2

Function 1 is the attachment of the hydrolyzable portion of the molecule to the surface of the inorganic (or proton-bearing) species. Function 2 is the ability of the titanate molecule to transesterify. Function 3 affects performance as determined by the chemistry of alkylate, carboxyl, sulfonyl, phenolic, phosphate, pyrophosphate, and phosphite groups. Function 4 provides van der Waals’ entanglement via long carbon chains. Function 5 provides thermoset reactivity via functional groups such as methacrylates and amines. Function 6 permits the presence of two or three pendent organic groups. This allows all functionality to be controlled to the first-, second-, or third-degree levels. Silane coupling agents are represented by the formula Z ˆ R ˆ SiY3 where Y represents a hydrolyzable group (typically alkoxy); Z is a functional organic group, such as amino, methacryloxy, epoxy; and R typically is a short aliphatic linkage that serves to attach the functional organic group to silicon in a stable fashion. Bonding to surface hydroxy groups of inorganic compounds is accomplished by the ˆ SiY3 portion, either by direct bonding of this group or more commonly via its hydrolysis product ˆ Si(OH)3. Subsequent reaction of the functional organic group with the organic matrix completes the coupling reaction and establishes a covalent chemical bond from the organic phase through the silane coupling agent to the inorganic phase. Flame Retardants. Flame retardants are thought to function via several mechanisms, dependent upon the class of flame retardant used. Halogenated flame retardants are thought to function principally in the vapor phase either as a diluent and heat sink or as a freeradical trap that stops or slows flame propagation. Phosphorus compounds are thought to function in the solid phase by forming a glaze or coating over the substrate that prevents the heat and mass transfer necessary for sustained combustion. With some additives, as the temperature is increased, the flame retardant acts as a solvent for the polymer, causing it to melt at lower temperatures and flow away from the ignition source. Mineral hydrates, such as alumina trihydrate and magnesium sulfate heptahydrate, are used in highly filled thermosetting resins. Foaming Agents (Chemical Blowing Agents). Foaming agents are added to polymers during processing to form minute gas cells throughout the product. Physical foaming agents include liquids and gases. Compressed nitrogen is often used in injection molding. Common liquid foaming agents are short-chain aliphatic hydrocarbons in the C5 to C7 range and their chlorinated or fluorinated analogs. The chemical foaming agent used varies with the temperature employed during processing. At relatively low temperatures (15–200 C), the foaming agent is often 4,4-oxybis(benzenesulfonylhydrazide) or p-toluenesulfonylhydrazide. In the midrange (160–232 C), either sodium hydrogen carbonate or 1,1azobisformamide is used. For the

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.7

high range (200–285 C), there are p-toluenesulfonylsemicarbazide, 5-phenyltetrazole and analogs, and trihydrazinotriazine. Inhibitors. Inhibitors slow or stop polymerization by reacting with the initiator or the growing polymer chain. The free radical formed from an inhibitor must be sufficiently unreactive that it does not function as a chain-transfer agent and begin another growing chain. Benzoquinone is a typical free-radical chain inhibitor. The resonance-stabilized free radical usually dimerizes or disproportionates to produce inert products and end the chain process. Lubricants. Materials such as fatty acids are added to reduce the surface tension and improve the handling qualities of plastic films. Plasticizers. Plasticizers are relatively nonvolatile liquids which are blended with polymers to alter their properties by intrusion between polymer chains. Diisooctyl phthalate is a common plasticizer. A plasticizer must be compatible with the polymer to avoid bleeding out over long periods of time. Products containing plasticizers tend to be more flexible and workable. Ultraviolet Stabilizers. 2-Hydroxybenzophenones represent the largest and most versatile class of ultraviolet stabilizers that are used to protect materials from the degradative effects of ultraviolet radiation. They function by absorbing ultraviolet radiation and by quenching electronically excited states. Hindered amines, such as 4-(2,2,6,6-tetramethylpiperidinyl) decanedioate, serve as radical scavengers and will protect thin films under conditions in which ultraviolet absorbers are ineffective. Metal salts of nickel, such as dibutyldithiocarbamate, are used in polyolefins to quench singlet oxygen or electronically excited states of other species in the polymer. Zinc salts function as peroxide decomposers. Vulcanization and Curing. Originally, vulcanization implied heating natural rubber with sulfur, but the term is now also employed for curing polymers. When sulfur is employed, sulfide and disulfide cross-links form between polymer chains. This provides sufficient rigidity to prevent plastic flow. Plastic flow is a process in which coiled polymers slip past each other under an external deforming force; when the force is released, the polymer chains do not completely return to their original positions. Organic peroxides are used extensively for the curing of unsaturated polyester resins and the polymerization of monomers having vinyl unsaturation. The ˆ O ˆ O ˆ bond is split into free radicals which can initiate polymerization or cross-linking of various monomers or polymers. TABLE 10.1 Plastic Families Acetals Acrylics Poly(methyl methacrylate) (PMMA) Poly(acrylonitrile) Alkyds Alloys Acrylic-poly(vinyl chloride) alloy Acrylonitrile–butadiene–styrene– poly(vinyl chloride) alloy (ABS–PVC) Acrylonitrile–butadiene–styrene– polycarbonate alloy (ABS–PC)

Allyls Allyl-diglycol-carbonate polymer Diallyl phthalate (DAP) polymer Cellulosics Cellulose acetate resin Cellulose-acetate–propionate resin Cellulose-acetate–butyrate resin Cellulose nitrate resin Ethyl cellulose resin Rayon Chlorinated polyether Epoxy

10.8

SECTION 10

TABLE 10.1 Plastic Families (continued ) Fluorocarbons Poly (tetrafluoroethylene) (PTFE) Poly (chlorotrifluoroethylene) (PCTFE) Perfluoroalkoxy (PFA) resin Fluorinated ethylene–propylene (FEP) resin Poly(vinylidene fluoride) (PVDF) Ethylene–chlorotrifluoroethylene copolymer Ethylene–tetrafluoroethylene copolymer Poly(vinyl fluoride) (PVF) Melamine formaldehyde Melamine phenolic Nitrile resins Phenolics Polyamides Nylon 6 Nylon 6/6 Nylon 6/9 Nylon 6/12 Nylon 11 Nylon 12 Aromatic nylons Poly(amide–imide) Poly(aryl ether) Polycarbonate (PC) Polyesters Poly(butylene terephthalate) (PBT) [also called polytetramethylene terephthalate (PTMT)] Poly(ethylene terephthalate) (PET) Unsaturated polyesters (SMC, BMC) Butadiene–maleic acid copolymer (BMC) Styrene–maleic acid copolymer (SMC) Polyimide Poly(methylpentene)

Polyolefins (PO) Low-density polyethylene (LDPE) High-density polyethylene (HDPE) Ultrahigh-molecular-weight polyethylene (UHMWPE) Polypropylene (PP) Polybutylene (PB) Polyallomers Poly(phenylene oxide) Poly(phenylene sulfide) (PPS) Polyurethanes Silicones Styrenics Polystyrene (PS) Acrylonitrile–butadiene–styrene (ABS) copolymer Sytrene–acrylonitrile (SAN) copolymer Styrene–butadiene copolymer Sulfones Polysulfone (PSF) Poly(ether sulfone) Poly(phenyl sulfone) Thermoplastic elastomers Polyolefin Polyester Block copolymers Styrene–butadiene block copolymer Styrene–isoprene block copolymer Styrene–ethylene block copolymer Styrene–butylene block copolymer Urea formaldehyde Vinyls Poly(vinyl chloride) (PVC) Poly(vinyl acetate) (PVAC) Poly(vinylidene chloride) Poly(vinyl butyrate) (PVB) Poly(vinyl formal) Poly(vinyl alcohol) (PVAL)

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.9

FORMULAS AND KEY PROPERTIES OF PLASTIC MATERIALS Acetals Homopolymer. Acetal homopolymers are prepared from formaldehyde and consist of high-molecular-weight linear polymers of formaldehyde. The trimer of formaldehyde is shown to the left and the structure of the polymer is shown at the right, below. O O

O

trioxane

The good mechanical properties of this homopolymer result from the ability of the oxymethylene chains to pack together into a highly ordered crystalline configuration as the polymers change from the molten to the solid state. Key properties include high melt point, strength and rigidity, good frictional properties, and resistance to fatigue. Higher molecular weight increases toughness but reduces melt flow. Copolymer. Acetal copolymers are prepared by copolymerization of 1,3,5-trioxane with small amounts of a co-monomer. Carbon–carbon bonds are distributed randomly in the polymer chain. These carbon–carbon bonds help to stabilize the polymer against thermal, oxidative, and acidic attack.

Acrylics Poly(methyl methacrylate). Acrylic acid is H2C ¨ CH ˆ COOH and methacrylic acid is H2C ¨ C(CH3)COOH. These compounds and their methyl esters are both quite reactive and difficult to store and handle. The monomer used to form poly(methyl methacrylate), 2-hydroxy-2-methylpropanenitrile, is prepared by the following reaction:

2-Hydroxy-2-methylpropanenitrile is then reacted with methanol (or other alcohol) to yield methacrylate ester. Free-radical polymerization is initiated by peroxide or azo catalysts and produce poly(methyl methacrylate) resins having the following formula:

Key properties are good resistance to heat, light, and weathering. This polymer is unaffected by most detergents, cleaning agents, and solutions of inorganic acids, alkalies, and aliphatic hydrocarbons. Poly(methyl methacrylate) has light transmittance of 92% with a haze of 1–3% and its clarity is equal to glass.

10.10

SECTION 10

Poly(methyl acrylate). The structure of methyl acrylate is H2C ¨ CH ˆ COOCH3. The monomer used to prepare poly(methyl acrylate) is produced by the oxidation of propylene. The resin is made by free-radical polymerization initiated by peroxide catalysts and has the following formula:

Poly(methyl acrylate) resins vary from soft, elastic, film-forming materials to hard plastics. Poly(acrylic acid) and Poly(methacrylic acid). Glacial acrylic acid and glacial methacrylic acid can be polymerized to produce water-soluble polymers having the following structures:

These monomers provide a means for introducing carboxyl groups into copolymers. In copolymers these acids can improve adhesion properties, improve freeze–thaw and mechanical stability of polymer dispersions, provide stability in alkalies (including ammonia), increase resistance to attack by oils, and provide reactive centers for cross-linking by divalent metal ions, diamines, or epoxides. Functional Group Methacrylate Monomers. Hydroxyethyl methacrylate and dimethylaminoethyl methacrylate produce polymers having the following formulas:

The use of hydroxyethyl (also hydroxypropyl) methacrylate as a monomer permits the introduction of reactive hydroxyl groups into the copolymers. This offers the possibility for subsequent cross-linking with an HO-reactive difunctional agent (diisocyanate, diepoxide, or melamineformaldehyde resin). Hydroxyl groups promote adhesion to polar substrates. Use of dimethylaminoethyl (also tert-butylaminoethyl) methacrylate as a monomer permits the introduction of pendent amino groups which can serve as sites for secondary crosslinking, provide a way to make the copolymer acid-soluble, and provide anchoring sites for dyes and pigments. Poly(acrylonitrile). Acrylonitrile has the formula H2C ¨ CH ˆ C ˜ N. Poly(acrylonitrile) polymers have the following formula:

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.11

Alkyds Alkyds are formulated from polyester resins, cross-linking monomers, and fillers of mineral or glass. The unsaturated polyester resins used for thermosetting alkyds are the reaction products of polyfunctional organic alcohols (glycols) and dibasic organic acids. Key properties of alkyds are dimensional stability, colorability, and arc track resistance. Chemical resistance, however, is generally poor. Alloys Polymer alloys are physical mixtures of structurally different homopolymers or copolymers. The mixture is held together by secondary intermolecular forces such as dipole interaction, hydrogen bonding, or van der Waals’ forces. Homogeneous alloys have a single glass transition temperature which is determined by the ratio of the components. The physical properties of these alloys are averages based on the composition of the alloy. Heterogeneous alloys can be formed when graft or block copolymers are combined with a compatible polymer. Alloys of incompatible polymers can be formed if an interfacial agent can be found. Allyls Diallyl Phthalate (and Diallyl 1,3-Phthalate). Phthalic acid is 1,2-dicarboxybenzene. The 1,3-isomer is generally referred to as isophthalic acid. These allyl polymers are prepared from O

O

O O O

O

O O

These resulting polymers are solid, linear, internally cyclized, thermoplastic structures containing unreacted allylic groups spaced at regular intervals along the polymer chain. Compounds derived from these polymers that are molded with mineral, glass, or synthetic fiber filling exhibit good electrical properties under high humidity and high temperature conditions. They also show stable low-loss factors, high surface and volume resistivity, and high arc and track resistance. Cellulosics Cellulose Triacetate. Cellulose triacetate is prepared according to the following reaction:

Because cellulose triacetate has a high softening temperature, it must be processed in solution. A mixture of dichloromethane and methanol is a common solvent.

10.12

SECTION 10

Cellulose triacetate sheeting and film have good gauge uniformity and good optical clarity. Cellulose triacetate products have good dimensional stability and resistance to water and have good folding endurance and burst strength. It is highly resistant to solvents such as acetone. Cellulose triacetate products have good heat resistance and a high dielectric constant. Cellulose Acetate, Propionate, and Butyrate. Cellulose acetate is prepared by hydrolyzing the triester to remove some of the acetyl groups; the plastic-grade resin contains 38–40% acetyl. The propionate and butyrate esters are made by substituting propionic acid and its anhydride (or butyric acid and its anhydride) for some of the acetic acid and acetic anhydride. Plastic grades of cellulose-acetate–propionate resin contain 39–47% propionyl and 2–9% acetyl; cellulose-acetate–butyrate resins contain 26–39% butyryl and 12–15% acetyl. These cellulose esters form tough, strong, stiff, hard plastics with almost unlimited color possibilities. Articles made from these plastics have a high gloss and are suitable for use in contact with food. Cellulose Nitrate. Cellulose nitrate is prepared according to the following reaction: C6H10O5  HNO3 l [ ˆ C6H7O2(OH)(ONO2)2 ˆ ]n The nitrogen content for plastics is usually about 11%, for lacquers and cement base it is 12%, and for explosives it is 13%. The standard plasticizer added is camphor. Key properties of cellulose nitrate are good dimensional stability, low water absorption, and toughness. Its disadvantages are its flammability and lack of stability to heat and sunlight. Ethyl Cellulose. Ethyl cellulose is prepared by reacting cellulose with caustic to form caustic cellulose, which is then reacted with chloroethane to form ethyl cellulose. Plasticgrade material contains 44–48% ethoxyl. Although not as resistant as cellulose esters to acids, it is much more resistant to bases. An outstanding feature is its toughness at low temperatures. Rayon. Viscose rayon is obtained by reacting the hydroxy groups of cellulose with carbon disulfide in the presence of alkali to give xanthates. When this solution is poured (spun) into an acid medium, the reaction is reversed and the cellulose is regenerated (coagulated). Epoxy Epoxy resin is prepared by the following condensation reaction:

The condensation leaves epoxy end groups that are then reacted in a separate step with nucleophilic compounds (alcohols, acids, or amines). For use as an adhesive, the epoxy

10.13

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

resin and the curing resin (usually an aliphatic polyamine) are packaged separately and mixed together immediately before use. Epoxy novolac resins are produced by glycidation of the low-molecular-weight reaction products of phenol (or cresol) with formaldehyde. Highly cross-linked systems are formed that have superior performance at elevated temperatures.

Fluorocarbon Poly(tetrafluoroethylene). Poly(tetrafluoroethylene) is prepared from tetrafluoroethylene and consists of repeating units in a predominantly linear chain: F2C ¨ CF2 l [ ˆ CF2 ˆ CF2 ˆ ]n Tetrafluoroethylene polymer has the lowest coefficient of friction of any solid. It has remarkable chemical resistance and a very low brittleness temperature (100 C). Its dielectric constant and loss factor are low and stable across a broad temperature and frequency range. Its impact strength is high. Fluorinated Ethylene–Propylene Resin. Polymer molecules of fluorinated ethylenepropylene consist of predominantly linear chains with this structure: CF2

CF2

CF2

CF CF3

n

Key properties are its flexibility, translucency, and resistance to all known chemicals except molten alkali metals, elemental fluorine and fluorine precursors at elevated temperatures, and concentrated perchloric acid. It withstands temperatures from 270  to 250 C and may be sterilized repeatedly by all known chemical and thermal methods. Perfluoroalkoxy Resin. CF2

Perfluoroalkoxy resin has the following formula: CF2

CF

CF2

where R is

CF2

Cn F2n + 1

O R

n

It resembles polytetrafluoroethylene and fluorinated ethylene propylene in its chemical resistance, electrical properties, and coefficient of friction. Its strength, hardness, and wear resistance are about equal to the former plastic and superior to that of the latter at temperatures above 150 C. Poly(vinylidene fluoride). Poly(vinylidene fluoride) consists of linear chains in which the predominant repeating unit is [ ˆ CH2 ˆ CF2 ˆ ]n It has good weathering resistance and does not support combustion. It is resistant to most chemicals and solvents and has greater strength, wear resistance, and creep resistance than the preceding three fluorocarbon resins.

10.14

SECTION 10

Poly(1-chloro-1,2,2-trifluoroethylene). Poly(1-chloro-1,2,2-trifluoroethylene consists of linear chains in which the predominant repeating unit is CF2

CF Cl

n

It possesses outstanding barrier properties to gases, especially water vapor. It is surpassed only by the fully fluorinated polymers in chemical resistance. A few solvents dissolve it at temperatures above 100 C, and it is swollen by a number of solvents, especially chlorinated solvents. It is harder and stronger than perfluorinated polymers, and its impact strength is lower. Ethylene–Chlorotrifluoroethylene Copolymer. Ethylene–chlorotrifluoroethylene copolymer consists of linear chains in which the predominant 1:1 alternating copolymer is CH2

CH2

CF2

CF Cl

n

This copolymer has useful properties from cryogenic temperatures to 180C. Its dielectric constant is low and stable over a broad temperature and frequency range. Ethylene–Tetrafluoroethylene Copolymer. Ethylene–tetrafluoroethylene copolymer consists of linear chains in which the repeating unit is [ ˆ CH2 ˆ CH2 ˆ CF2 ˆ CF2 ˆ ]n Its properties resemble those of ethylene–chlorotrifluoroethylene copolymer. Poly(vinyl fluoride). Poly(vinyl fluoride) consists of linear chains in which the repeating unit is [ ˆ CH2 ˆ CHF ˆ ]n It is used only as a film, and it has good resistance to abrasion and resists staining. It also has outstanding weathering resistance and maintains useful properties from 100 to 150 C. Nitrile Resins The principal monomer of nitrile resins is acrylonitrile (see “Polyacrylonitrile”), which constitutes about 70% by weight of the polymer and provides the polymer with good gas barrier and chemical resistance properties. The remainder of the polymer is 20–30% methyl acrylate (or styrene), with 0–10% butadiene to serve as an impact-modifying termonomer. Melamine Formaldehyde The monomer used for preparing melamine formaldehyde is formed as follows:

10.15

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

Hexamethylolmelamine can further condense in the presence of an acid catalyst; ether linkages can also form (see “Urea Formaldehyde”). A wide variety of resins can be obtained by careful selection of pH, reaction temperature, reactant ratio, amino monomer, and extent of condensation. Liquid coating resins are prepared by reacting methanol or butanol with the initial methylolated products. These can be used to produce hard, solvent-resistant coatings by heating with a variety of hydroxy, carboxyl, and amide functional polymers to produce a cross-linked film. Phenolics Phenol–formaldehyde resin. Phenol–formaldehyde resin is prepared from phenol by reaction with formaldehyde. Phenol is an enol, the 2-, 4-, and 6-positions of which are activated for reaction with an electrophile. Phenol is sequentially hydroxymethylated approximately as illustrated below. Dehydration of the phenolic hydroxymethyl groups affords a benzyl cation, a new electrophile that can react with another substituted or unsubstituted molecule of phenol. Both linear polymerization and cross-linking are possible, depending on the ratio of the reactants and the polymerization conditions.

OH

OH H 2C=O

OH CH 2 OH H 2C=O HOH 2C

OH CH 2 OH H 2C=O HOH2C

CH2OH

CH2OH

One-Stage Resins. The ratio of formaldehyde to phenol is high enough to allow the thermosetting process to take place without the addition of other sources of cross-links. Two-Stage Resins The ratio of formaldehyde to phenol is low enough to prevent the thermosetting reaction from occurring during manufacture of the resin. At this point the resin is termed novolac resin. Subsequently, hexamethylenetetramine is incorporated into the material to act as a source of chemical cross-links during the molding operation (and conversion to the thermoset or cured state).

Polyamides Nylon 6, 11, and 12. This class of polymers is polymerized by addition reactions of ring compounds that contain both acid and amine groups on the monomer.

Nylon 6 is polymerized from 2-oxohexamethyleneimine (6 carbons); nylon 11 and 12 are made this way from 11- and 12-carbon rings, respectively. Nylon 6/6, 6/9, and 6/12. As illustrated below, nylon 6/6 is polymerized from 1,6-hexanedioic acid (six carbons) and 1,6-hexanediamine (six carbons).

10.16

SECTION 10

HOOC ˆ (CH2)4 ˆ COOH  H2N ˆ CH2 ˆ (CH2)4 ˆ CH2 ˆ NH2l 1,6-Hexanedioic acid

1,6-Hexanediamine

Other nylons are made this way from different combinations of monomers to produce types 6/9, 6/10, and 6/12. Nylon 6 and 6/6 possess the maximum stiffness, strength, and heat resistance of all the types of nylon. Type 6/6 has a higher melt temperature, whereas type 6 has a higher impact resistance and better processibility. At a sacrifice in stiffness and heat resistance, the higher analogs of nylon are useful primarily for improved chemical resistance in certain environments (acids, bases, and zinc chloride solutions) and for lower moisture absorption. Aromatic nylons, [ ˆ NH ˆ C6H4 ˆ CO ˆ ]n, (also called aramids) have specialty uses because of their improved clarity.

Poly (amide-imide) Poly(amide-imide) is the condensation polymer of 1,2,4-benzenetricarboxylic anhydride and various aromatic diamines and has the general structure:

It is characterized by high strength and good impact resistance, and retains its physical properties at temperatures up to to 260 C. Its radiation (gamma) resistance is good. Polycarbonate Polycarbonate is a polyester in which dihydric (or polyhydric) phenols are joined through carbonate linkages. The general-purpose type of polycarbonate is based on 2,2-bis(4hydroxybenzene) propane (bisphenol A) and has the general structure:

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.17

Polycarbonates are the toughest of all thermoplastics. They are window-clear, amazingly strong and rigid, autoclavable, and nontoxic. They have a brittleness temperature of 135C. Polyester Poly(butylene terephthalate). Poly(butylene terephthalate) is prepared in a condensation reaction between dimethyl terephthalate and 1,4-butanediol and its repeating unit has the general structure O

O

O n

O

This thermoplastic shows good tensile strength, toughness, low water absorption, and good frictional properties, plus good chemical resistance and electrical properties. Poly(ethylene terephthalate). Poly(ethylene terephthalate) is prepared by the reaction of either terephthalic acid or dimethyl terephthalate with ethylene glycol, and its repeating unit has the general structure O

O

O O

n

The resin has the ability to be oriented by a drawing process and crystallized to yield a high-strength product. Unsaturated Polyesters. Unsaturated polyesters are produced by reaction between two types of dibasic acids, one of which is unsaturated, and an alcohol to produce an ester. Double bonds in the body of the unsaturated dibasic acid are obtained by using maleic anhydride or fumaric acid. PCTA Copolyester. Poly(1,4-cyclohexanedimethylene terephthalic acid) (PCTA) copolyester is a polymer of cyclohexanedimethanol and terephthalic acid, with another acid substituted for a portion of the terephthalic acid otherwise required. It has the following formula:

Polyimides. Polyimides have the following formula:

10.18

SECTION 10

They are used as high-temperature structural adhesives since they become rubbery rather than melt at about 300 C. Poly(methylpentene) Poly(methylpentene) is obtained by a Ziegler-type catalytic polymerization of 4-methyl-1pentene. Its key properties are its excellent transparency, rigidity, and chemical resistance, plus its resistance to impact and to high temperatures. It withstands repeated autoclaving, even at 150 C. Polyolefins Polyethylene. Polymerization of ethylene results in an essentially straight-chain highmolecular-weight hydrocarbon. CH2 ¨ CH2l[ ˆ CH2 ˆ CH2 ˆ ]n Branching occurs to some extent and can be controlled. Minimum branching results in a “high-density” polyethylene because of its closely packed molecular chains. More branching gives a less compact solid known as “low-density” polyethylene. A key property is its chemical inertness. Strong oxidizing agents eventually cause some oxidation, and some solvents cause softening or swelling, but there is no known solvent for polyethylene at room temperature. The brittleness temperature is 100 C for both types. Polyethylene has good low-temperature toughness, low water absorption, and good flexibility at subzero temperatures. Polypropylene. structure:

The polymerization of propylene results in a polymer with the following

The desired form in homopolymers is the isotactic arrangement (at least 93% is required to give the desired properties). Copolymers have a random arrangement. In block copolymers a secondary reactor is used where active polymer chains can further polymerize to produce segments that use ethylene monomer. Polypropylene is translucent and autoclavable and has no known solvent at room temperature. It is slightly more susceptible to strong oxidizing agents than polyethylene. Polybutylene. Polybutylene is composed of linear chains having an isotactic arrangement of ethyl side groups along the chain backbone.

It has a helical conformation in the stable crystalline form.

10.19

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

Polybutylene exhibits high tear, impact, and puncture resistance. It also has low creep, excellent chemical resistance, and abrasion resistance with coilability. Ionomer. Ionomer is the generic name for polymers based on sodium or zinc salts of ethylene–methacrylic acid copolymers in which interchain ionic bonding, occurring randomly between the long-chain polymer molecules, produces solid-state properties. The abrasion resistance of ionomers is outstanding, and ionomer films exhibit optical clarity. In composite structures ionomers serve as a heat-seal layer.

Poly(phenylene sulfide) Poly(phenylene sulfide) has the following formula:

The recurring para-substituted benzene rings and sulfur atoms form a symmetrical rigid backbone. The high degree of crystallization and the thermal stability of the bond between the benzene ring and sulfur are the two properties responsible for the polymer’s high melting point, thermal stability, inherent flame retardance, and good chemical resistance. There are no known solvents of poly(phenylene sulfide) that can function below 205 C. Polyurethane Foams. Polyurethane foams are prepared by the polymerization of polyols with isocyanates. One of the most commonly used reactive isocyanates toluenediisocyanate, TDI. It is made from toluene by nitration and then reduction followed by treatment with phosgene. The isocyanate residue reacts readily with alcohols to give carbamates (urethanes) or amines to give ureas. CH 3 N C O +

O

C

HO [ CH 2 CH 2O ]n

H

N CH 3

CH 3

H N

O O [

NH

CH 2 CH 2O ] n O

NH O

H N

O

10.20

SECTION 10

Commonly used isocyanates are toluenediisocyanate, methylenediphenylisocyanate, and polymeric isocyanates. Polyols used are macroglycols based on either polyester or polyether. The former [poly(ethylene phthalate) or poly(ethylene 1,6-hexanedioate)] have hydroxyl groups that are free to react with the isocyanate. Most flexible foam is made from 80/20 toluene diisocyanate (which refers to the ratio of 2,4-toluenediisocyanate to 2,6toluene diisocyanate). High-resilience foam contains about 80% 80/20 toluenediisocyanate and 20% poly(methylene diphenyl isocyanate), while semiflexible foam is almost always 100% poly(methylene diphenyl isocyanate). Much of the latter reacts by trimerization to form isocyanurate rings. Flexible foams are used in mattresses, cushions, and safety applications. Rigid and semiflexible foams are used in structural applications and to encapsulate sensitive components to protect them against shock, vibration, and moisture. Foam coatings are tough, hard, flexible, and chemically resistant. Elastomeric Fiber. Elastomeric fibers are prepared by the polymerization of polymeric polyols with diisocyanates. CH 3 N C O +

O

C

N

H2C

(OCH 2CH 2 O)xH

HC

(OCH 2CH 2 O)yH

H2C

(OCH 2CH 2 O)zH

essentially linear polymers

polymeric diols

toluenediisocyanate

The structure of elastomeric fibers is similar to that illustrated for polyurethane foams.

SILICONES Silicones are formed in the following multistage reaction:

The silanols formed above are unstable and undergo dehydration. On polycondensation, they give polysiloxanes (or silicones) which are characterized by their three-dimensional branched-chain structure. Various organic groups introduced within the polysiloxane chain impart certain characteristics and properties to these resins. Methyl groups impart water repellency, surface hardness, and noncombustibility. Phenyl groups impart resistance to temperature variations, flexibility under heat, resistance to abrasion, and compatibility with organic products. Vinyl groups strengthen the rigidity of the molecular stucture by creating easier crosslinkage of molecules. Methoxy and alkoxy groups facilitate cross-linking at low temperatures. Oils and gums are nonhighly branched or straight-chain polymers whose viscosity increases with the degree of polycondensation.

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.21

Styrenics Polystyrene. Polystyrene has the following formula:

Polystyrene is rigid with excellent dimensional stability, has good chemical resistance to aqueous solutions, and is an extremely clear material. Impact polystyrene contains polybutadiene added to reduce brittleness. The polybutadiene is usually dispersed as a discrete phase in a continuous polystyrene matrix. Polystyrene can be grafted onto rubber particles, which assures good adhesion between the phases. Acrylonitrile–Butadiene–Styrene (ABS) Copolymers. This basic three-monomer system can be tailored to yield resins with a variety of properties. Acrylonitrile contributes heat resistance, high strength, and chemical resistance. Butadiene contributes impact strength, toughness, and retention of low-temperature properties. Styrene contributes gloss, processibility, and rigidity. ABS polymers are composed of discrete polybutadiene particles grafted with the styrene–acrylonitrile copolymer; these are dispersed in the continuous matrix of the copolymer. Styrene–Acrylonitrile (SAN) Copolymers. SAN resins are random, amorphous copolymers whose properties vary with molecular weight and copolymer composition. An increase in molecular weight or in acrylonitrile content generally enhances the physical properties of the copolymer but at some loss in ease of processing and with a slight increase in polymer color. SAN resins are rigid, hard, transparent thermoplastics which process easily and have good dimensional stability—a combination of properties unique in transparent polymers. Sulfones Below are the formulas for three polysulfones.

10.22

SECTION 10

The isopropylidene linkage imparts chemical resistance, the ether linkage imparts temperature resistance, and the sulfone linkage imparts impact strength. The brittleness temperature of polysulfones is 100 C. Polysulfones are clear, strong, nontoxic, and virtually unbreakable. They do not hydrolyze during autoclaving and are resistant to acids, bases, aqueous solutions, aliphatic hydrocarbons, and alcohols. Thermoplastic Elastomers Polyolefins. In these thermoplastic elastomers the hard component is a crystalline polyolefin, such as polyethylene or polypropylene, and the soft portion is composed of ethylene–propylene rubber. Attractive forces between the rubber and resin phases serve as labile cross-links. Some contain a chemically cross-linked rubber phase that imparts a higher degree of elasticity. Styrene–Butadiene–Styrene Block Copolymers. Styrene blocks associate into domains that form hard regions. The midblock, which is normally butadiene, ethylene–butene, or isoprene blocks, forms the soft domains. Polystyrene domains serve as cross-links. Polyurethanes. The hard portion of polyurethane consists of a chain extender and polyisocyanate. The soft component is composed of polyol segments. Polyesters. The hard portion consists of copolyester, and the soft portion is composed of polyol segments. Vinyl Poly(vinyl chloride) (PVC). Polymerization of vinyl chloride results in the formation of a polymer with the following formula:

When blended with phthalate ester plasticizers, PVC becomes soft and pliable. Its key properties are good resistance to oils and a very low permeability to most gases. Poly(vinyl acetate). Poly(vinyl acetate) has the following formula:

Poly(vinyl acetate) is used in latex water paints because of its weathering, quick-drying, recoatability, and self-priming properties. It is also used in hot-melt and solution adhesives. Poly(vinyl alcohol). Poly(vinyl alcohol) has the following formula:

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POLYMERS, RUBBERS, FATS, OILS, AND WAXES

It is used in adhesives, paper coating and sizing, and textile warp size and finishing applications. Poly(vinyl butyral). Poly(vinyl butyral) is prepared according to the following reaction:

CH2

+ CH3CH2CH2CHO →

CH OH

n

CH2

CH O

CH2

CH

CH

O

CH2

CH2

CH3

n

Its key characteristics are its excellent optical and adhesive properties. It is used as the interlayer film for safety glass. Poly(vinylidene chloride). Poly(vinylidene chloride) is prepared according to the following reaction: CH2 ¨ CCl2  CH2 ¨ CHCl l [ ˆ CH2 ˆ CCl2 ˆ CH2 ˆ CHCl ˆ ]n Random copolymer

Urea Formaldehyde The reaction of urea with formaldehyde yields the following products, which are used as monomers in the preparation of urea formaldehyde resin. H2N ˆ CO ˆ NH2  H2CO l H2N ˆ CO ˆ NH ˆ CH2OH  HOCH2 ˆ NH ˆ CO ˆ NH ˆ CH2OH The reaction conditions can be varied so that only one of these monomers is formed. 1-Hydroxymethylurea and 1,3-bis(hydroxymethyl)urea condense in the presence of an acid catalyst to produce urea formaldehyde resins. A wide variety of resins can be obtained by careful selection of the pH, reaction temperature, reactant ratio, amino monomer, and degree of polymerization. If the reaction is carried far enough, an infusible polymer network is produced. Liquid coating resins are prepared by reacting methanol or butanol with the initial hydroxymethylureas. Ether exchange reactions between the amino resin and the reactive sites on the polymer produce a cross-linked film.

10.24

TABLE 10.2 Properties of Commercial Plastics Acetal

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, KV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Homopolymer

Copolymer

20% glassreinforced homopolymer

25% glassreinforced copolymer

21% poly(tetrafluoroethylene)filled homopolymer

175

175

181

175

181

1.42 0.25–0.40 19.7

1.41 0.22 19.7

1.56 0.25 19.3

1.61 0.29 22.8

1.54 0.20 15.7

1015 3.7 3.7

1015 3.7 3.7

5  1014 3.9 3.9

3  1016 3.1 3.1

0.005

0.005

0.005

0.005

670

450

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

5.29 25–75

16 (10% yield) 40–75

18 (10% yield) 7

17 (10% yield) 3

13 (10% yield) 15–22

380–430

375

730

1 100

340–350

14 M94

13 M78

15 M90

28 M79

M78

69–123 520

53–80 410

43 1 000

96 1 250

37–64

10

10

8.5

18.5

7.6

9.5–12

8.5

6.9–7.6

27.9 100

85

36–81

124

110

157

84 0.35 0.23

0.23

75

163

100

10.25

10.26

TABLE 10.2 Properties of Commercial Plastics (continued ) Alloy Acrylic

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, KV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 104 lb · in2

Poly(methyl methacrylate)

Cast sheet

Impactmodified

Heatresistant

90–105

90–105

80–100

100–125

1.17–1.20 0.1–0.4 15.7–19.9

1.18–1.20 0.2–0.4 17.7–21.7

1.11–1.18 0.2–0.8 15.0–19.9

1.16–1.19 0.2–0.3 15.7–19.9

 1014 3.3–4.5

 1014 3.5–4.5 3.0–3.5

3.8–5.0 3.6–4.7

0.04–0.06 0.02–0.03

0.012–0.026 0.01–0.016

370–460

390–475

240–370

350–460

Alkyd, molded

Acrylic poly(vinyl chloride) alloy

Acrylonitrile– butadiene– styrenepoly(vinyl chloride) alloy

105 2.22–2.24 0.06  15.7

330–400

19.7

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2

12–18 2–10

11–19 2–7

4–14 20–70

17 3–5

420–460

390–475

200–380

460–500

13–19 M85–M105

12–17 M80–M100

7–13 R105–R120

12–16 M95–M105

16–27 380–450

16–21 350–450

43–133 200–400

16–21 350–460

7–11

8–11

5–9

10

8.4 100 330–400

340

10.7 R99–R105

9.6 R100

27–240

800 330–335

560 330

4.5–6.5

6.5

5.8

E76

10–13

Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

16–20

0.5–2.2

Selfextinguishing

50–90

50–90

50–80

50–60

40–55

74–99

71–102

74–95

88–104

177–204

0.36

60–71 0.35

0.17–0.25

0.17–0.25

220

0.17–0.21

0.19

46 71

10.27

10.28

TABLE 10.2 Properties of Commercial Plastics (continued ) Alloy

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1

Polycarbonate acrylonitrile– butadiene– styrene alloy

150 1.12–1.20 0.21–0.24 17.7

Allyl

Glass-filled

Mineral-filled

Thermoset

Thermoset

Thermoset

230

230

140

1.3–1.4 0.2 15.0

1.7–2.0 0.12–0.35 15.7–17.7

1.65–1.85 0.2–0.5 15.7–17.7

1.27–1.34 2–7 11–24

1.29–1.34 1.7–6.5 9–24

1.15–1.22 0.9–2.2 9–18

1010–1013 3.4–7.4 3.2–7.0

1010–1013 3.5–7.5 3.2–7.0

1010–1012 3.7–4.3 3.3–3.8

0.01–0.06 0.01–0.06

0.01–0.06 0.01–0.10

0.01–0.04 0.01–0.04

300

Diallyl phthalate molding

Cellulose acetate

Celluloseacetate– butyrate resin

Allyl–diglycol– carbonate polymer

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Cellulosic

Sheet

Molding

Sheet

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

11 10–15

21–23

25–35 3–5

20–32 3–5

300–400

250–330

1 200–1 500

1 000–1 400

13.0–13.7

6–13

9–20

8.5–11

6–10

2–16

4–9

R117

M95–M100

E80–E87

E61

R85–R120

R100–R123

R50–R95

560 370–380

11–21 300

21–800 1 400–2 200

16–43 1 200–2 200

107–454

53–214

133–288 200–250

7.0–7.3

5–6

6–11

5–8

4.5–8.0

1.9–9.0

2.6–6.9

2.2–7.4

4.1–7.6

8.5

22–33 17–40

25–36 6–40

50–100 740–1 300

1.3–3.8

1.3–3.8

63–67

5.4–9.6

0.68–2.4

2.8

100–150

80–180

110–170

104–116

60–88

165–288

160–288

44–91

51–98

49–58

0.3–0.4

0.3–0.42

0.3–0.4

0.17–0.34

0.17–0.34

0.17–0.34

0.25–0.38

0.20–0.21

0.21–0.63

0.30–1.04

10.29

10.30

TABLE 10.2 Properties of Commercial Plastics (continued ) Cellulosic

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Celluloseacetate– butyrate resin, molding

Celluloseacetate– propionate resin, molding

Bisphenol Ethyl cellulose

140

190

135

1.15–1.22 0.9–2.2 9–13

1.17–1.24 1.2–2.8 12–17.7

1.09–1.17 0.8–1.8 13.8–19.7

1010–1012 3.5–6.4 3.2–6.2

Epoxy

3.01

Cellulose nitrate

1.35–1.40

Chlorinated polyether

Glass-fiberreinforced

Mineralfilled

125

Thermoset

Thermoset

1.4

1.6–2.0 0.04–0.20 9.8–15.7

1.6–2.1 0.03–0.20 9.8–15.7

1010 7.0–7.5 6.6

0.01–0.04 0.01–0.04

3 000

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

2.1–7.5 40–88

2.4–7.0 29–100

90–300

120–350

1.8–9.3 R31–R116

2.9–11.4 R10–R122

4–12 R50–R115

9–11 R95–R115

5 R100

8–30 M100–M112

6–18 M100–M112

53–582 50–200

27 to no break 60–215

21

267–374 190–220

21

16–533 3

16–22

2.6–6.9

2.0–7.8

2–8

7–8

1.5–1.8

5–20

4–10

5–40

2.1–8.0 40–45

600–800

18 000–40 000 18 000–40 000 4 2–4.5

1.3–3.8

Selfextinguishing

110–170

110–170

100–200

80–120

6.6

11–50

20–60

44–94

44–109

45–88

60–71

185

107–260

107–260

0.17–0.42

0.17–1.48

255 0.3–0.4 0.17–0.30

0.31–0.41 0.17–0.30

0.16–0.30

0.23

10.31

10.32

TABLE 10.2 Properties of Commercial Plastics (continued ) Epoxy

Fluorocarbon Poly(tetrafluoroethylene)

Casting resin Properties Perfluoroalkoxy Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Novolac resin Glass-fiberreinforced

Poly(chlorotrifluoroethylene)

Unfilled

Flexible

Mineral-filled

Granular

Thermoset

Thermoset

Thermoset

327

327

220

310

1.11–1.40 0.08–0.15 11.8–19.7

1.05–1.35 0.27–0.50 9.3–15.8

1.7–2.1 0.05–0.2 11.8–13.8

2.14–2.20 0.01 18.9

2.2–2.3

2.1–2.2 0.03 19.7–23

2.12–2.17

1012–1017 3.5–5.0 3.5–5.0

12.6

1018 2.1 2.1

1018 2.3–2.7 2.3–2.5

0.000 2 0.000 2

0.001 0.005

60

19.7

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2

15–25 3–6

1–14 20–70

30 2–4

1.7 200–400

200–300

4.6–7.4 80–250

2 000

80

235

120

(D50–D55)

2 (D60–D70)

7.4–9.3 R75–R95

16–20

13–21 M80–M110

1–13

10.7–53 350

187–267 1–350

21

160 58–80

144

133–160 150–300

No break

4–13

2–10

6–12

2–5

2–2.7

4.5–6

4–4.3

Selfextinguishing

Selfextinguishing

Selfextinguishing

77–100

70

(D64)

30

Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

300

45–65

20–100

22–30

100

46–288

23–121

149–260

121 (66 lb · in2)

126 (66 lb · in2)

260 0.25

200 0.22

0.17–0.21

0.25

0.34–0.40

0.19–0.22

74 (66 lb · in2

0.25

10.33

10.34

TABLE 10.2 Properties of Commercial Plastics (continued ) Fluorocarbon

Melamine formaldehyde

Ethylene–tetrafluoroethylene copolymer

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Fluorinated ethylenepropylene resin

Poly(vinylidene fluoride)

Unfilled

Glass-fiberreinforced

Ethylene– chlorotrifluoroethylene copolymer

Cellulosefilled

Glass-fiberreinforced

275

156

270

270

245

Thermoset

Thermoset

2.14–2.17  0.01 20–24

1.75–1.78 0.04–0.06 10

1.7 0.03 16

1.8 0.02 17

1.68 0.01 19

1.47–1.52 0.1–0.8 11–16

1.5–2.0 0.09–1.3 5–15

2.1 2.1

8–9 8–9

2.6 2.6

2.6 2.6

High High

120

120

1 200

240

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

2.2 250–330

8.7–10 25–500

7.1 100–400

10 8

200–300

33–45 0.6–1.0

20–35 0.6

80–95

200

200

950

240

1 100

(D60–D65)

8.6–11 (D80)

5.5 R50 (D75)

10.7 R74

7 R95

9–16 M115–M125

14–23 M115

No break 50

192–214 120

No break 120

480 1 200

No break 240

11–21 1.1–1.4

32–961 1.6–2.4

2.7–3.1

5.5–7.4

6.5

12

7

5–13

5–10.5

Not combustible

Not combustible

Not combustible

Not combustible

Not combustible

Selfextinguishing

Selfextinguishing

83–105

85

59

10–32

80

40–45

15–28

70 (66 lb · in2)

80–90

71

210

77

177–199

190–204

205 0.28

150

0.25

0.19–0.24

210

0.24

0.16

0.27–0.41

0.41–0.49

10.35

10.36

TABLE 10.2 Properties of Commercial Plastics (continued )

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Melamine phenolic, woodflour- and cellulosefilled

Phenolic

Nitrile

Thermoset 1.5–1.7 0.3–0.65 8.7–12.8

95 1.15 0.28 8.7–9.5

1.9  1015

Woodflourfilled

Glass-fiberreinforced

Cellulosefilled

Mineralfilled

Thermoset

Thermoset

Thermoset

Thermoset

Thermoset

1.24–1.32 0.1–0.36 9.8–15.8

1.37–1.46 0.3–1.2 10.2–15.8

1.69–2.0 0.03–1.2 5.5–15.8

1.38–1.42 0.5–0.9 11.8–15

1.42–1.84 0.1–0.3 7.9–13.8

Unfilled

1  1012 to 7  1012 6.5–7.5 4.0–5.5 0.10–0.15 0.04–0.05

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2

26–30 0.4–0.8

12 3–4

18–32 1.5–2.0

25–31 0.4–0.8

26–70 0.2

22–31 1–2

22.5–34.6 0.1–0.5

1 000–1 200

500–590

700–1 500

1 000–1 200

2 000–33 000

900–1 300

1 000–2 000

8–10 E95–E100

14 M72–M76

11–17 M93–M120

7–14 M100–M115

15–60 E54–E101

5.5–11 M95–M115

11–14 E88

11–21 800–1 700

80–256 510–580

13–21 700–1 500

11–32 800–1 700

27–960 1 900–3 300

21–59

14–19 2 400

6–8

9

6–9

5–9

7–18

3.5–6.5

6–9.7

12–15

Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

Selfextinguishing 10–40

66

68

30–45

8–21

20–31

19–26

140–154

73

74–80

149–188

177–316

149–177

320–246

0.17–0.30

0.26

0.15

0.17–0.34

0.34–0.59

0.25–0.38

0.42–0.57

10.37

10.38

TABLE 10.2 Properties of Commercial Plastics (continued ) Polyamide Nylon 6

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Molding and extrusion

30–35% glassfiberreinforced

Nylon 6/6 High-impact copolymer

Molding

33% glassfiberreinforced

Molybdenum disulfidefilled

Nylon 6/6nylon 6 copolymer

216

216

216

265

265

265

240

1.12–1.14 2.9 15.8

1.35–1.42 1.2 15.8

1.08–1.17 1.3–1.5 22

1.13–1.15 1.0–1.3 24

1.38 1.0

1.15–1.17 0.8–1.1 14

1.08–1.14 1.5–2.0 15.8

1012 9.8 3.7

1012–1015 4.0 3.6

1010 16 4

0.14 0.12

0.01–0.02 0.02–0.03

0.4 0.1

250

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

13–16 30–100

19 3–6

150–270

15 (yield) 60

24.9 3

12.5 15

40

390

1 500

110–320

420

1 300

450

150–410

14 R119

33 M101

5–12 R81–R110

17 R120

41 M100

17 R119

R119

32–53

160

96 to no break

43–53

117

240

37

380

1 450

550

150–410

11.8

25

28

13.7

7.4–12.4

Selfextinguishing

7.5–11

8

12 8

Selfextinguishing

Selfextinguishing

Selfextinguishing

Selfextinguishing

Selfextinguishing

Selfextinguishing

80–90

20–30

30–40

80

15–20

54

68–85

210

45–54

75

249

127

107 0.4 0.24

135 0.4 0.24

0.24

0.22

77

10.39

10.40

TABLE 10.2 Properties of Commercial Plastics (continued ) Polyamide Nylon 6/12

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Nylon 6/9, molding and extrusion

Molding

30–35% glass-fiberreinforced

Nylon 11, molding and extrusion

Nylon 12, molding and extrusion

Aromatic nylon (aramid), molded and unfilled

Poly(amideimide), unfilled

205

217

217

194

179

275

1.08–1.10 0.5 24

1.06–1.08 0.4 16

1.31–1.38 0.2 21

1.03–1.05 0.3 17

1.01–1.02 0.25 18

1.30 0.6 31

275 1.40 0.28 24

290

413

1015 4.0 3.5

1014 3.8 3.0

0.02 0.02

0.07 0.04

180

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2

1 125

2.4 150

4

300

7.5 300

30 5

40 12–18

290

290

1 120

150

165

640

664

R111

R114

E40–E50

R108

1.5 R106–R109

25.8 E90

30 E78

59 275

53 290

139 1 200

96 185

107–300 180

75

133 730

8.5

8.8

24

8

8–9

17.5

26.9

55–100

67–100

40

36

54

54

260

274

8.8

Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

Selfextinguishing 90

57–60

82

93–218

0.4

100–120 0.58

0.22

0.34

260

0.22

0.22

0.25

10.41

10.42

TABLE 10.2 Properties of Commercial Plastics (continued ) Polycarbonate

Thermoplastic polyester Poly(butylene terephthalate)

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Poly(aryl ether), unfilled

Low viscosity

30% glass-fiberreinforced

160 1.14 0.25 17

140 1.2 0.15 15

150 1.4 0.14 19

2  1016 3.17 2.96

 1016 3.35 3.31

0.000 9 0.010

0.011 0.007

350

1 300

Unfilled

30% glass-fiberreinforced

Poly(ethylene terephthalate)

Unfilled

30% glass-fiberreinforced

232–267

232–267

245

245

1.31–1.38 0.08–0.09 16–22

1.52 0.06–0.08 18–22

1.34–1.39 0.1–0.2

1.27 0.05 22

1016

1016 3.25

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2

80

12.5 110

18 3–5

8.6–14.5 50–300

18–23.5 2–4

11–15 50–300

25 3

300

340

1 100

330–400

1 100–1 200

35–450

1 440

11 R117

13.5 M70

23 M92

12–16.7 M68–M78

26–29 M90

14–18 M94–M101

33.5 M100

427 320

14 345

107 1250

43–53 280

69–85 1 300

13–32 400–600

101 1 440

7.5

9.5

19

8.2

17–19

8.5–10.5

23

9.0

Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

Selfextinguishing

Selfextinguishing

65

68

22

60–95

25

65

29

149

138–145

146

50–85

220

38–41

224

143 0.3 0.30

0.20

0.27 0.22

0.18–0.30

0.30

0.15

10.43

10.44

TABLE 10.2 Properties of Commercial Plastics (continued ) Thermoplastic polyester Aromatic polyester

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1

Extrusiontransparent

Injection molding

Thermosetting and alkyd polyester Unsaturated polyester Styrene–maleic acid copolymer, low-shrink

Thermoset

Butadiene– maleic acid copolymer

Thermoset

Alkyd molding compounds

Putty, mineral-filled

Glass-fiberreinforced

Thermoset

Thermoset

81

310–365 1.36–1.43 0.24 22

1.39 0.01 14

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2 Compressive strength, rupture or 1% yield, 103 lb · in2

Polyimide, unfilled

 1016 3–4

2 000–3 000 10

15–30

14–30

12–38

15–36

30–40

Elongation at break. % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

225

7–10

3–5

290

700

1 000–2 500

10.6 R105

12

9–35 40–70 (Barcol)

300 11

101

6

8–10 2 000

2 000

450–500

16–24 50–60 (Barcol)

6–17 E98

8.5–26 E95

19–28.8 E52–E99

133–800 1 000–2 500

214–694 1 500–2 500

16–27 500–3 000

27–854

80 300

4.5–20

5–10

3–9

4–9.5

10.5–17.1

7

63

12.5

29

6–30

282

190–260

160–177

20–50

15–33

45–56

177–260

204–260

277–360

0.27 0.29

0.76–0.93

0.51–0.89

0.6–0.89

0.10–0.11

10.45

10.46

TABLE 10.2 Properties of Commercial Plastics (continued ) Polyolefin Polyethylene

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1

Poly(methyl pentene), unfilled

Medium-density

High-density

Glass-fiberreinforced, high-density

230–240 0.84 0.01

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Low-density

Ultra highmolecularweight

114–171

Ethylene– vinyl acetate copolymer

65–90 95–130 0.910–0.925  0.01 18–39

120–140 0.926–0.94  0.01 18–39

120–140 0.941–0.965  0.01 18–39

 1015 2.3 2.3

 1015 2.3 2.3

 1015 2.3 2.3

 0.000 5  0.000 5

 0.000 5  0.000 5

 0.000 5  0.000 5

125–135 0.94  0.01 28

120–140 1.28 0.02 20

0.92–0.95 0.05–0.13 24–30

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

5–6.6 10–50

90–800

50–600

2.7–3.6 20–130

450–525

7 1.5

550–900

110–260

8–60

60–115

100–260

130–140

800

1–20

4–6.5 L67–L74

(D40–D51)

(D50–D60)

R30–R50

R50

11 R75

16–64 160–280

No break 14–38

27–854 25–55

27–1 068 60–180

No break

59

No break 20–120

3.5–4

0.6–2.3

1.2–3.5

3.1–5.5

5.6

9

1.4–2.8

0.8–1.2

1.0–2.2

3–4

3.1–4.0

1.0

1.0

1.0

117

100–220

140–160

110–130

130

48

160–200

41

32–41

41–49

43–54

43–49

121

34

175

70 0.55

93 0.55

200 0.46–0.55

0.17

0.34

0.34–0.42

0.46–0.51

0.46

10.47

10.48

TABLE 10.2 Properties of Commercial Plastics (continued ) Polyolefin

Poly(phenylene sulfide)

Polypropylene

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1

Polybutylene extrusion

Copolymer

126

168

160–168

0.91–0.925 0.01–0.02 18

0.90–0.91 0.01–0.03 24

0.89–0.905 0.03 24

0.90  0.03 24

1017 2.2–2.6 2.2–2.6

1017 2.3 2.3

1017 2.3

 0.000 5 0.000 5–0.002

0.000 1–0.000 5 0.000 1–0.002

0.000 3

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Homopolymer

Impact copolymer

31

150–300

Polyallomer

Injection molding

40% glass-fiberreinforced

120–135

290

290

0.90  0.01 31

1.3  0.02 15

1.6 0.05 18

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

300–380

5.5–8.0 100–600

3.5–8.0 200–700

8–20

400–500

16 1–2

21 1

45–50

170–250

130–200

130–190

70–110

550

1 700

2–2.3

6–8 R80–R102

5–7 R50–R96

R40–R90

R50–R85

14 R123

29 R123

No break 30–40

21–53 165–225

53–1 068 100–170

80–900

91–203

 27 480

75 1 100

3.8–4.4

4.5–6

4–5.5

3–3.8

9.5

19.5

1.7–2.5

4.5–5.4

3.5–4.3

2.5–3.1

3–3.4

128–150

81–100

68–95

60–90

83–100

49

22

54–60

48–57

45–57

90–105 (66 lb · in2)

51–56

135

249

160 0.44–0.46

240 0.45–0.50

140–160 0.45–0.50

0.12

0.15–0.17

0.12–0.17

0.09–0.17

0.29

0.29

0.22

10.49

10.50

TABLE 10.2 Properties of Commercial Plastics (continued ) Polyurethane

Silicone Mineraland /or glass-filled

Epoxy molding and encapsulating compound

Thermoset

Thermoset

Thermoset

Casting resin Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Liquid

Thermoset 1.1–1.5 0.02–1.5 12–20

1011–1015 4.0–7.5

Unsaturated

Thermoplastic elastomer

Thermoset 1.05 0.1–0.2

Styrenic

Cast resin, flexible

120–160 1.05–1.25 0.7–0.9 13–25

0.99–1.5

1.8–1.94

1.84

22

8–15

10

1011–1013 5.4–7.6

1014–1015 2.7–4.2

Polystyrene Crystal

85–105 1.04–1.05 0.03–0.10 24

 1016 2.5

10–100

4–9

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

20 100–1 000

3–6

20 100–1 100

10–100

610

10–350

0.7–4.5

19

0.7–9 (A65–D80)

1 334 to flexible 10–100

21

0.175–10

10–11

10–16

28

100–700 1 000–2 500

(A15–A65)

No break

380–450

9–14 M80–M90

17

8–14 M60–M75

13–427

16

13–21

10–350 1.5–8.4

11.5–16 1–2

350–485 0.35–1.0

4–6.5

6–8

5.3–7.9

20–50

30

70–80

260

74–100

0–78 100–200 Varies over wide range

100–200 87–93

300–800

Varies over wide range

371 0.43

0.43

0.21

0.07–0.31

0.15–0.31

0.30

93 0.3 0.68

0.09–0.13

10.51

10.52

TABLE 10.2 Properties of Commercial Plastics (continued ) Styrenic Polystyrene

Acrylonitrile–butadiene–styrene copolymer Molding

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1

Heatresistant

Extrusion

110–125 1.05–1.09 0.03–0.12 20

88–120 1.02–1.06 0.20–0.45 14–20

Heatresistant

110–125 1.05–1.08 0.20–0.45 14–20

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

High-impact

Flameretarded

100–110 1.01–1.04 0.20–0.45 14–20

110–125 1.16–1.21 0.2–0.6 14–20

2.4–5.0 2.4–3.8 0.003–0.008 0.007–0.015

150–390

190–440

140–300

130–310

Platable

20% glassreinforced

100–110 1.06–1.07

1.22

16–22

18

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

11.5–16 2–60

5.2–10 20–100

7.2–10 3–20

4.5–8 5–70

6.5–7.5 5–25

340–470

130–420

300–400

250–350

300–400

340–390

710

8.9–14 L80–L108

4–14 R75–R115

10–13 R100–R115

8–11 R85–R105

9–14 R100–R120

10.5–11.5 R103–R109

15.5 M85

21–181 320–460

133–640 130–380

107–347 300–350

347–400 230–330

160–640 320–400

267–283 330–380

64 740

5–7.8

2.5–8.0

6–7.5

4.8–6.3

5–8

6–6.4

11

5.5–7

4–5.5

4–6

1.3

14

1.3

60–70

60–130

60–93

95–110

65–95

47–53

21

93–120

77–104 annealed

104–116 annealed

96–102 annealed

90–107 annealed

96–102 annealed

99

110 0.3–0.4 0.19–0.34

10.53

10.54

TABLE 10.2 Properties of Commercial Plastics (continued ) Styrenic

Sulfone

Styrene-acrylonitrile copolymer

Properties

Unfilled

20% glass-fiberreinforced

Polysulfone Styrene– butadiene copolymer, high-impact

Unfilled

20% glass-fiberreinforced

Poly(ether sulfone)

Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), %

115–125 1.07–1.08 0.2–0.3

115–125 1.22 0.15–0.20

90–110 1.03–1.06 0.05–0.10

200 1.24 0.22

200 1.46 0.23

230 1.37 0.43

Dielectric strength, kV · mm1

16–20

20

18

17

17

17

1015 3.14 3.26

3.7 3.7

0.004 0.008

0.002 0.009

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

530

370

Poly(phenyl sulfone)

220 1.29 1.1–1.3 (saturated) 16

Compressive strength, rupture of 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2 Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

14–17 1–4

19 1–2

4–9 13–50

13.9 50–100

22 2

30–80

60

550

100–1 100

280–450

390

1 000

375

330

14–17 M80–M90

20 R122

5.3–9.4 M10–M68

15.4 M69, R120

23 R123

18.7 M88

12.4

19–27 400–560

53 1 150–1 200

32–192 280–465

64 360

59 1 200

85 350

640 310

9–12

15.8–18

3.2–4.9

12.2

10.4

17

2.9–4.9

10.2

36–38

38–40

70–101

52–56

25

55

31

88–104

99

74–93

174

182

203

204

0.38

0.14–0.19

149

0.12

0.26–0.28

0.12–0.21

0.12

10.55

10.56

TABLE 10.2 Properties of Commercial Plastics (continued ) Thermoplastic elastomers

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1

Polyolefin

Polyester

Block copolymers of styrene and butadiene or styrene and isoprene

Block copolymers of styrene and ethylene or styrene and butylene

168–206 0.88–0.90 0.01 24–26

1.17–1.25

Urea formaldehyde, alpha-cellulose filled

Poly(vinyl chloride) and poly(vinyl acetate)

Rigid

Flexible and unfilled

Thermoset 0.9–1.2 0.19–0.39 16–21

Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Vinyl

3.6–120

0.9–1.2

1.47–1.52 0.4–0.8 12–16

75–105 1.30–1.58 0.04–0.4 14–20

75–105 1.16–1.35 0.15–0.75 12–16

0.5–5.0 7.7–9.5 6.7–8.0

1012–1015 3.2–4.0 3.0–4.0

1011–1014 5.0–9.0 3.0–4.0

0.036–0.043 0.025–0.035

0.01–0.02 0.006–0.02

0.03–0.05 0.06–0.1

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2

150–300

350–450

500–1 350

600–800

25–45 1

8–13 40–80

1.5–2.0

7–75

4–150

4–100

1 300–1 600

300–500

(A65–A92)

(D40–D72)

(A40–A90)

(A50–A90)

10–18 M110–M120

10–16 (D65–D95)

No break

208 to no break 1.1–2.5

No break

No break

13–21

21–1068

1 000–1 500

350–600

3.7–5.7

0.6–3.0

5.5–13

6–75

1.5–3.5

Selfextinguishing

Selfextinguishing

Slow to selfextinguishing

130–137

22–36

50–100

70–250

 0–49

127–143

60–77

77 0.6

70–74 0.2–0.28

0.30–0.42

0.15–0.21

0.65–2.0

0.8–50

Thermal Burning rate, mm · min1

Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

130–170

0.19–0.21

0.15

1–3

0.9–1.7 200–450

(A50–A100) Varies over wide range

80–105 0.36–0.5 0.13–0.17

10.57

10.58

TABLE 10.2 Properties of Commercial Plastics (continued ) Vinyl Poly(vinyl chloride) and poly(vinyl acetate)

Properties Physical Melting temperature, C Crystalline Amorphous Specific gravity Water absorption (24 h), % Dielectric strength, kV · mm1 Electrical Volume (dc) resistivity, ohm-cm Dielectric constant (60 Hz) Dielectric constant (106 Hz) Dissipation (power) factor (60 Hz) Dissipation factor (106 Hz) Mechanical Compressive modulus, 103 lb · in2

Flexible and filled

Poly(vinyl chloride), 15% glass-fiberreinforced

Poly(vinylidene chloride)

Poly(vinyl formal)

Chlorinated poly(vinyl chloride)

Poly(vinyl butyral), flexible

110 1.49–1.56 0.02–0.15

49 1.05 1.0–2.0 14

210 75–105 1.3–1.7 0.5–1.0 9.8–12

75–105 1.54 0.01 24–31

1.65–1.72 0.1 16–24

105 1.2–1.4 0.5–3.0 19

1014–1016 4.5–6.0

335–600

Compressive strength, rupture or 1% yield, 103 lb · in2 Elongation at break, % Flexural modulus at 23 C, 103 lb · in2 Flexural strength, rupture or yield, 103 lb · in2 Hardness, Rockwell (or Shore) Impact strength (Izod) at 23 C, J · m1 Tensile modulus, 103 lb · in2 Tensile strength at break, 103 lb · in2 Tensile yield strength, 103 lb · in2

1.0–1.8 200–400

9 2–3

5–20

750

(A50–A100) Varies over wide range

1–3.5

9–22 4–65

4.2–6.2 M50–M65

17–18 M85

14.5–17 R117–R122

53

16–53

43–75

53–299

870

50–80

350–600

360–475

9.5

3–5

10–12

7.5–9

Selfextinguishing

68

190

64

68–78

54–71

71–77

94–112

0.16

0.14

0.13

A10–A100 Varies over wide range

0.5–3.0

Slow

100 0.32 0.13–0.17

150–450

380–450

13.5 R118

Thermal Burning rate, mm · min1 Coefficient of linear thermal expansion, 106 C Deflection temperature under flexural load (264 lb · in2), C Maximum recommended service temperature, C Specific heat, cal · g1 Thermal conductivity, W · m1 · K1

2–2.7 50–250

10.59

10.60

SECTION 10

FORMULAS AND ADVANTAGES OF RUBBERS Gutta Percha Gutta percha is a natural polymer of isoprene (3-methyl-1,3-butadiene) in which the configuration around each double bond is trans. It is hard and horny and has the following formula:

Natural Rubber Natural rubber is a polymer of isoprene in which the configuration around each double bond is cis (or Z):

Its principal advantages are high resilience and good abrasion resistance. Chlorosulfonated Polyethylene Chlorosulfonated polyethylene is prepared as follows:

Cross-linking, which can occur as a result of side reactions, causes an appreciable gel content in the final product. The polymer can be vulcanized to give a rubber with very good chemical (solvent) resistance, excellent resistance to aging and weathering, and good color retention in sunlight. Epichlorohydrin Epichlorohydrin is a product of covulcanization of epichlorohydrin (epoxy) polymers with rubbers, especially cis-polybutadiene. Its advantages include impermeability to air, excellent adhesion to metal, and good resistance to oils, weathering, and low temperature. Nitrile Rubber (NBR, GRN, Buna N) Nitrile rubber can be prepared as follows: CH2¨CHßCH¨CH2  CH2¨CHßCNl 2 parts 1 part

10.61

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

Nitrile rubber is also known as nitrile–butadiene rubber (NBR), government rubber nitrile (GRN), and Buna N. It possesses resistance to oils up to 120 C and excellent abrasion resistance and adhesion to metal. Polyacrylate Polyacrylate has the following formula:

It possesses oil and heat resistance to 175 C and excellent resistance to ozone. cis-Polybutadiene Rubber (BR) cis-Polybutadiene is prepared by polymerization of butadiene by mostly 1,4-addition. CH2 ¨ CH ˆ CH ¨ CH2 l [ ˆ CH2 ˆ CH ¨ CH ˆ CH2 ˆ ]n The polybutadiene produced is in the Z (or cis) configuration. cis-Polybutadiene has good abrasion resistance, is useful at low temperature, and has excellent adhesion to metal. Polychloroprene (Neoprene) Polychloroprene is prepared as follows: CH2

CH

C

CH2 →

CH2

CH

C(Cl)

CH2

n

Cl

It has very good weathering characteristics, is resistant to ozone and to oil, and is heatresistant to 100 C. Ethylene–Propylene–Diene Rubber (EPDM) Ethylene–propylene–diene rubber is polymerized from 60 parts ethylene, 40 parts propylene, and a small amount of nonconjugated diene. The nonconjugated diene permits sulfur vulcanization of the polymer instead of using peroxide. It is a very lightweight rubber and has very good weathering and electrical properties, excellent adhesion, and excellent ozone resistance. Polyisobutylene (Butyl Rubber) Polyisobutylene is prepared as follows:

10.62

SECTION 10

It possesses excellent ozone resistance, very good weathering and electrical properties, and good heat resistance. (Z)-Polyisoprene (Synthetic Natural Rubber) Polymerization of isoprene by 1,4-addition produces polyisoprene that has a cis (or Z) configuration.

Polysulfide Rubbers Polysulfide rubbers are prepared as follows: Cl ˆ R ˆ Cl  Na ˆ S ˆ S ˆ S ˆ S ˆ Na l HS [ ˆ R ˆ S ˆ S ˆ S ˆ S ˆ ]nR ˆ SH where R can be ˆ CH2CH2 ˆ , ˆ CH2CH2 ˆ O ˆ CH2CH2 ˆ , or ˆ CH2CH2 ˆ O ˆ CH2 ˆ O ˆ CH2CH2 ˆ . Polysulfide rubbers possess excellent resistance to weathering and oils and have very good electrical properties. Poly(vinyl chloride) (PVC) Poly(vinyl chloride) as previously discussed under “Formulas and Key Properties of Plastic Materials” has the following structures:

PVC polymer plus special plasticizers are used to produce flexible tubing which has good chemical resistance. Silicone Rubbers Silicone rubbers are prepared as follows:

Other groups may replace the methyl groups. Silicone rubbers have excellent ozone and weathering resistance, good electrical properties, and good adhesion to metal.

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

10.63

Styrene–Butadiene Rubber (GRS, SBR, Buna S) Styrene–butadiene rubber is prepared from the free-radical copolymerization of one part by weight of styrene and three parts by weight of 1,3-butadiene. The butadiene is incorporated by both 1,4-addition (80%) and 1,2-addition (20%). The configuration around the double bond of the 1,4-adduct is about 80% trans. The product is a random copolymer with these general features:

Styrene–butadiene rubber (SBR) is also known as government rubber styrene (GRS) and Buna S.

Urethane See Table 10.3.

10.64

TABLE 10.3 Properties of Natural and Synthetic Rubbers

Rubber Gutta percha (hard rubber) Natural rubber (NR) Chlorosulfonated polyethylene Epichlorohydrin Fluoroelastomers Isobutene–isoprene rubber (IIR) [also known as government rubber I(GR-I)] Nitrile rubber (butadiene–acrylonitrile rubber) (also known as Buna N and NBR) Polyacrylate Polybutadiene rubber (BR) Polychloroprene (neoprene) Poly(ethylene–propylene–diene) (EPDM) Polyisobutylene (butyl rubber) Polyisoprene Polysulfide (Thiokol ST) Poly(vinyl chloride) (Koroseal) Silicone, high-temperature Silicone Styrene–butadiene rubber (SBR) (also known as Buna S) Urethane

Service temperature, C

Specific gravity

Durometer hardness (or Shore)

Ultimate elongation % (23 C)

Tensile strength, lb · in2 (23 C)

Minimum

Maximum

1.2–1.95 0.93 1.10 1.27 1.4–1.95

(65–95) 20–100 50–95 60–90 60–90

3–8 750–850 100–500 100–400 100–350

4000–1 0,000 3000–4500 500–3000 1000–2500 2000–3000

56 54 46 40

104 82 121 121 232

0.91

(40–70)

750–950

2300–3000

1.00 1.10 0.93 1.23 0.85 0.92 0.94 1.34 1.32

30–100 40–100 30–100 20–90 30–100 30–100 20–100 20–80 (80–90)

100–600 100–400 100–700 800–1000 100–300 100–700 100–750 100–400

0.98 0.94 0.85

20–95 40–100 62–95

50–800 400–600 100–700

500–4000 1000–2200 2500–3000 2000–3500 1000–3000 1000–3000 2000–3000 700–1250 2400–3000 700–800 500–1500 1600–3700 1000–8000

121 54 18 62 54 40 54 54 54 84 60 54

121 149 79–100 121 149 100 79–82 82–100 71 316 232 107 100

CHEMICAL RESISTANCE TABLE 10.4 Resistance of Selected Polymers and Rubbers to Various Chemicals at 20 C The information in this table is intended to be used only as a general guide. The chemical resistance classifications are E excellent (30 days of exposure causes no damage), G good (some damage after 30 days), F fair (exposure may cause crazing, softening, swelling, or loss of strength), N not recommended (immediate damage may occur).

Hydrocarbons, aromatic Hydrocarbons, halogenated

Ketones

Oxidizing agents, strong

Hydrocarbons, aliphatic

N N G N

N N G N

N N N N

N N

G

N G E F

E G G G E E E

E G N G F F G

E F N F G F G E

E F N F N N N E

E G N N F G G E

E N N F F F F

Glycols

Ethers

Esters

Alkalies, concentrated

Aldehydes

Alcohols, aliphatic

Acids, strong and concentrated

Acids, dilute or weak

Chemical

Polymers Acetals Acrylics: poly(methyl methacrylate) Allyls: diallyl phthalate Cellulosics: cellulose-acetate–butyrate and cellulose–acetate– propionate polymers Fluorocarbons Polyamides Polycarbonates Polyesters Poly(methyl pentene) Low-density polyethylene High-density polyethylene Polybutadiene

F G G F

N N

F E

N

N

N

N

E N G G E E E G

E N N G E E E F

E G G N G E E E

E E F G G E

N N N N

N N

N E

G E

N

N

E E N N E E E

E G N N G G G

E N F N N N

10.65

Hydrocarbons, aliphatic

Hydrocarbons, aromatic Hydrocarbons, halogenated

Ketones

Oxidizing agents, strong

F N

N N

G N

F N

G F

G N N F F G

N N N

N N N

N N N

G G

E E E E E E

N E F N E N

N N N N F N

N N N N N N

N N N N N N

Glycols

Ethers

Esters

Alkalies, concentrated

Aldehydes

Alcohols, aliphatic

Acids, strong and concentrated

Chemical

Acids, dilute or weak

10.66

TABLE 10.4 Resistance of Selected Polymers and Rubbers to Various Chemicals at 20 C (continued )

Polymers (continued) APolypropylene and polyallomer Polystyrene Styrene–acrylonitrile copolymers Styrene–acrylonitrile–butadiene copolymers Sulfones: polysulfone Vinyls: poly(vinyl chloride)

E N

E N

G E

N N G

E E N G F E

E

F G

E N N G E G

G N

N

E E F

N N N

F F

N N N F E N

N G F F E N

Rubbers Natural rubber Nitrile rubber Polychloroprene Polyisobutylene Polysulfide rubbers: Thiokol Styrene–butadiene rubber

E E E E E E

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

TABLE 10.5 Common Abbreviations Used in Polymer Chemistry Acronym

Expansion

ABA ABS ABS–PC ABS–PVC ACM ACS AES AMMA AN APET APP ASA BR BS CA CAB CAP CN CP CPE CPET CPP CPVC CR CTA DAM DAP DMT ECTFE EEA EMA EMAA EMAC EMPP EnBA EP EPM ESI EVA(C) EVOH FEP HDI HDPE HIPS HMDI IPI LDPE LLDPE MBS

Acrylonitrile–butadiene–acrylate Acrylonitrile–butadiene–styrene copolymer Acrylonitrile–butadiene–styrene–polycarbonate alloy Acrylonitrile–butadiene–styrene–poly(vinyl chloride) alloy Acrylic acid ester rubber Acrylonitrile–chlorinated pe-styrene Acrylonitrile–ethylene–propylene–styrene Acrylonitrile–methyl methacrylate Acrylonitrile Amorphous polyethylene terephthalate Atactic polypropylene Acrylic–styrene–acrylonitrile Butadiene rubber Butadiene styrene rubber Cellulose acetate Cellulose acetate–butyrate Cellulose acetate–propionate Cellulose nitrate Cellulose propionate Chlorinated polyethylene Crystalline polyethylene terephthalate Cast polypropylene Chlorinated polyvinyl chloride Chloroprene rubber Cellulose triacetate Diallyl maleate Diallyl phthalate Terephthalic acid, dimethyl ester Ethylene–chlorotrifluoroethylene copolymer Ethylene–ethyl acrylate Ethylene–methyl acrylate Ethylene methacrylic acid Ethylene–methyl acrylate copolymer Elastomer modified polypropylene Ethylene normal butyl acrylate Epoxy resin, also ethylene–propylene Ethylene–propylene rubber Ethylene–styrene copolymers Polyethylene–vinyl acetate Polyethylene–vinyl alcohol copolymers Fluorinated ethylene–propylene copolymers Hexamethylene diisocyanate High-density polyethylene High-impact polystyrene Diisocyanato dicyclohexylmethane Isophorone diisocyanate Low-density polyethylene Linear low-density polyethylene Methacrylate–butadiene–styrene

10.67

10.68

SECTION 10

TABLE 10.5 Common Abbreviations Used in Polymer Chemistry (continued ) Acronym

Expansion

MC MDI MEKP MF MMA MPEG MPF NBR NDI NR OPET OPP OSA PA PAEK PAI PAN PB PBAN PBI PBN PBS PBT PC PCD PCT PCTFE PE PEC PEG PEI PEK PEN PES PET PF PFA PI PIBI PMDI PMMA PMP PO PP PPA PPC PPO PPS PPSU

Methyl cellulose Methylene diphenylene diisocyanate Methyl ethyl ketone peroxide Melamine formaldehyde Methyl methacrylate Polyethylene glycol monomethyl ether Melamine–phenol–formaldehyde Nitrile butyl rubber Naphthalene diisocyanate Natural rubber Oriented polyethylene terephthalate Oriented polypropylene Olefin–modified styrene–acrylonitrile Polyamide Poly(aryl ether–ketone) Poly(amide–imide) Polyacrylonitrile Polybutylene Poly(butadiene–acrylonitrile) Polybenzimidazole Polybutylene naphthalate Poly(butadiene–styrene) Poly(butylene terephthalate) Polycarbonate Polycarbodiimide Poly(cyclohexylene–dimethylene terephthalate) Polychlorotrifluoroethylene Polyethylene Chlorinated polyethylene Poly(ethylene glycol) Poly(ether–imide) Poly(ether–ketone) Polyethylene naphthalate Polyether sulfone Polyethylene terephthalate Phenol–formaldehyde copolymer Perfluoroalkoxy resin Polyimide Poly(isobutylene), Butyl rubber Polymeric methylene diphenylene diisocyanate Poly(methyl methacrylate) Poly(methylpentene) Polyolefins Polypropylene Polyphthalamide Chlorinated polypropylene Poly(phenylene oxide) Poly(phenylene sulfide) Poly(phenylene sulfone)

POLYMERS, RUBBERS, FATS, OILS, AND WAXES

TABLE 10.5 Common Abbreviations Used in Polymer Chemistry (continued ) Acronym

Expansion

PS PSF PSU PTFE PU PUR PVA PVAL PVB PVC PVCA PVDA PVDC PVDF PVF PVOH SAN SB SBC SBR SMA SMC TA TDI TEFE TPA UF ULDPE UP UR VLDPE ZNC

Polystyrene Polysulfone (also PSU) Polysulfone (also PSF) Polytetrafluoroethylene Polyurethane Polyurethane Poly(vinyl acetate) Poly(vinyl alcohol) poly(vinyl butyrate) Poly(vinyl chloride) Poly(vinyl chloride–acetate) Poly(vinylidene acetate) Poly(vinylidene chloride) Poly(vinylidene fluoride) Poly(vinyl fluoride) Poly(vinyl alcohol) Styrene–acrylonitrile copolymer Styrene–butadiene copolymer Styrene block copolymer Styrene butadiene rubber Styrene–maleic anhydride (also SMC) Styrene–maleic anhydride (also SMA) Terephthalic acid (also TPA) Toluene diisocyanate Ethylene–tetrafluoroethylene copolymer Terephthalic acid (also TA) Urea formaldehyde Ultralow-density polyethylene Unsaturated polyester resin Urethane Very low-density polyethylene Ziegler-Natta catalyst

10.69

10.70

GAS PERMEABILITY TABLE 10.6 Gas Permeability Constants (1010P) at 25 C for Polymers and Rubbers The gas permeability constant P is defined as amount of permeant (area)  (time)  (driving forced across the film) The gas permeability constant is the amount of gas expressed in cubic centimeters passed in 1 s through a 1-cm2 area of film when the pressure across a film thickness of 1 cm is 1 cmHg and the temperature is 25 C. All tabulated values are multiplied by 1010 and are in units of seconds1 (centimeters of Hg)1. Other temperatures are indicated by exponents and are expressed in degrees Celsius. P

Gas Polymer or rubber

He

N2

H2

O2

CO2

H2O

Cellulose (cellophane) Cellulose acetate

0.00520 13.620

0.003 2 0.2830

0.006 5 3.520

0.002 1 0.7830

0.004 7 22.730

1 900 5 500

Cellulose nitrate Ethyl cellulose

6.9 40030

0.12 8.430

2.020 8720

1.95 26.530

2.12 41.030

6 290 12 00020

2.17 9.43

14.4 52.0

6.16 23.3

35.4 15.3

510 2 290

0.03830

0.1030

177

Gutta percha Natural rubber

Nylon 6

0.5320

Nylon 11

1.9530

Poly(acrylonitrile)

0.009 530 1.7830

1.0040 0.000 2

0.000 8

300

Other 0.00645 (H2S); 0.001 7 (SO2) 3.530 (H2S); 170 (ethylene oxide); 6.860 (bromomethane) 57.1 (NH3); 1.76 (SO2) 705 (NH3); 204 (SO2); 4200 (ethylene oxide) 15.7 (CO); 30.1 (CH4); 1.68 (C3H8); 98.9 (C2H2); 550 (CH3C ˜ CH); 3.59 (SF6) 0.3330 (H2S); 1.220 (NH3); 0.8460 (CH3Br) 0.34430 (Ne); 0.18940 (Ar); 13.650 (propyne)

Acrylonitrile–styrene copolymer (66 : 34) Poly(1,3-butadiene) Poly(cis-1,4-butadiene) Butadiene–acrylonitrile copolymer (80 : 20) Butadiene–styrene copolymer (80 : 20) Butadiene–styrene copolymer (92 : 8) Polychloroprene Polyethylene, low-density

0.048 19.0

0.21 138.0

2 000 5 070

6.42 19.2

41.9

15.9

3.85

30.8

4.9

1.06 1.71 5.11 1.2 0.969

13.6 12.030

4.0 2.88

25.8 12.6

90

Polyethylene, high-density

1.14

0.143

3.020

0.403

0.36

12.0

Poly(ethylene terephthalate) Crystalline Amorphous Poly(ethyl methacrylate)

1.32 3.28 6.82

0.006 5 0.013 0.220

3.7020

0.035 0.059 1.15

0.17 0.30 5.00

130

8.38

0.324

7.20

1.30

5.16

11038

7.77

0.181

7.41

0.852

4.32

Isobutene–isoprene copolymer (98 : 2) Isoprene–acrylonitrile copolymer (76 : 24)

32.6 12.2 13.4 22.9

19.2 (Ne); 41.0 (Ar)

3 200

24.8 (C2H2); 7.7 (propyne) 5.01 (Ne); 4.49 (Ar) 9.70 (Ne); 12.7 (Ar) 3.79 (Ar); 3.27 (CH4) 2.88 (CH4); 6.81 (C2H6); 9.43 (C3H8); 1.48 (CO); 490 (ethylene oxide); 14.4 (propene); 42.2 (propyne); 0.170 (SF6); 47260 (CH3Br) 0.388 (CH4); 0.590 (C2H6); 0.537 (C3H8); 0.008 3 (SF6); 1.69 (Ar); 4.01 (propene) 0.003 2 (CH4); 0.0860 (CH3Br) 0.009 (CH4) 2.98 (Ne); 0.565 (Ar); 0.370 (Kr); 3.83 (H2S); 0.000 001 65 (SF6) 13.650 (C3H8)

10.71

10.72

TABLE 10.6 Gas Permeability Constants (1010P) at 25 C for Polymers and Rubbers (continued ) Gas Polymer or rubber Isoprene–methacrylonitrile copolymer (76 : 24) Methacrylonitrile–styrene– butadiene copolymer (88 : 7 : 5) Poly(methylpentene) Polypropylene Silicone rubber, 10% filler

He

N2

H2

O2

CO2

H2O

0.596

13.6

2.34

14.1

7.83 0.4430 2270

136 4120 4640

0.004 8 32.0 2.330 4890

0.014 92.6 9.230 3 240

600

101 3820 2330

18.7

0.788 1.4 0.003

23.3 9.8 0.9420

2.63 4.2 0.02540

10.5 11.7 0.04840

1 200

8930

0.5030

51 43 00035

Polystyrene Poly(tetrafluoroethylene) Poly(trifluoroethylene)

6.820

Poly(vinyl acetate)

12.630

Poly(vinyl alcohol)

0.00130

 0.00114

0.009

0.008 9

0.00123

Poly(vinyl chloride)

2.05

0.011 8

1.70

0.045 3

0.157

275

Poly(vinylidene chloride)

0.3134

0.000 9430

0.005 330

0.0330

0.5

0.29

Other

0.3320 (H2S); 9.220 (NH3) 1910 (Ne); 5500 (Ar); 1 0200 (Kr); 2 5500 (Xe); 19 0000 (butane) 15.7 (NO2); 37.5 (N2O4) 1.20 (ethylene oxide); 4.660 (CH3Br) 2.6430 (Ne); 0.1930 (Ar); 0.07830 (Kr); 0.05030 (CH4) 0.007 (H2S); 0.0020 (ethylene oxide) 3.92 (Ne); 0.011 5 (Ar); 0.028 6 (CH4) 0.0330 (H2S); 0.00860 (CH3Br)

TABLE 10.7 Vapor Permeability Constants (1010P) at 35 C for Polymers All tabulated values are multiplied by 1010 and are in units of seconds1 (centimeters of Hg)1.

Vapor Polymer Cellulose Cellulose acetate Poly(acrylonitrile) Polyethylene, low-density Polystyrene Poly(vinyl alcohol)

Benzene

Hexane

1.4 512 2.61 5 300 10 600 3.58

0.912 2.80 1.59 2 910

Carbon tetrachloride

Ethanol

Ethyl acetate

0.836 3.74 1.47 3 810 6 820 1.61

85.8 2 980 0 55.9 0 32.7

13.4 3 595 1.34 513 soluble 2.53

2.34

FATS, OILS, AND WAXES TABLE 10.8 Constants of Fats and Oils

Fat or oil

Solidification point, C

Specific gravity (15 C/15 C)

Refractive index

Acid value

Saponification value

Iodine value

0.5–35 1.2 5.6 0.8–5.3

210–230 193–205 171–189 195–200

26–38 66–72 137–166 26–36

Animal origin

10.73

Butterfat Chicken fat Cod-liver oil Deer fat

20–23 21–27 3

40 C 0.9115 C 0.924 0.92–0.93 0.96–0.97

1.455 0.92525 C

10.74

TABLE 10.8 Constants of Fats and Oils (continued )

Fat or oil

Solidification point, C

Specific gravity (15 C/15 C)

Refractive index

Acid value

Saponification value

Iodine value

2–12

13 0.25 2–14 1.9

203 (body); 290 (jaw) 233–236 191–193 170–194 195–200 193–200 193–198 195–203 189–193 193–199 203 199–203 188–196 188–196 157–164 120–137 196–200 195–196 160–202

127 (body); 33 (jaw) 25–37 58–67 102–149 75–86 57–73 63–79 47–67 148–185 58–75 127 70–100 130–152 130–152 115–139 80–84 35–42 48–61 90–146

0.5–3.5

199 183–208

100 93–103

Animal origin (continued) Dolphin Goat butter Goose fat Herring oil Horse fat Human fat Lard oil Lard oil, fatty tissue Menhaden oil Neat’s-foot oil Porpoise, body oil Rabbit fat Sardine oil Seal Shark Sperm oil Tallow, beef Tallow, mutton Whale oil

3 to 5

22–24 20–45 15 2 to 4 27–30 5 2 to 10 16 17–23 20–22 3 15.5 31–38 32–41 2 to 0

0.91–0.93 38 C 0.91  0.9438 C 0.92–0.93 0.92–0.94 0.92–0.93 0.903 0.913–0.915 0.93–0.94 0.92–0.93 0.91–0.92 0.926 0.93–0.94 0.92–0.93 0.915–0.926 0.916–0.919 0.878–0.884 0.895 0.937–0.953 0.917–0.924

0.90060 C 1.460 1.462 1.462 1.46560 C 1.46425 C 1.46660 C

1.45740 C 1.46060 C

0.6 1.8–44 0–2.4 0.1–2.5 0.5–0.8 3–12 0.1–0.6 1.2 1.4–7.2 4–25 1.9–40

Plant origin Acorn Almond

10 20 to 15

0.916 0.914–0.921

10.75

Babassu oil Beechnut oil Castor oil Chaulmoogra oil, USP Chinese vegetable tallow Cocoa butter Coconut oil Corn (maize) oil Cottonseed oil Hazelnut oil Hemp-seed oil Linseed oil Mustard oil, black Neem oil Niger-seed oil Oiticica oil Olive oil Palm oil Palm kernel oil Peanut oil Perilla oil Pistachio-nut oil Poppy-seed oil Pumpkin-seed oil Rapeseed oil Safflower oil Sesame oil Soybean oil Sunflower-seed oil Tung oil White-mustard-seed oil Wheat-germ oil

22–26 17 18 to 17  25 24–34 21.5–23 14–22 20 to 10 13 to 12 18 to 17 28 to 15 27 to 19 16 3 6 35–42 24 3 10 to 5 18 to 16 15 10 18 to 13 6 to 4 16 to 10 17 2.5 16 to 8

0.89360 C 0.922 0.960–0.967 0.95025 C 0.918–0.922 0.964–0.974 0.926 0.921–0.928 0.91825C 25C 0.917 0.928–0.934 0.930–0.938 0.918–0.921 0.917 0.925 0.97425 C 0.914–0.918 0.915 0.918–0.925 0.917–0.926 0.930–0.937 0.913–0.919 0.924–0.926 0.923–0.925 0.913–0.917 0.925–0.928 0.91925C 25C 0.924–0.927 0.924–0.926 0.94–0.95 0.912–0.916

1.44360 C 1.477

0.1–0.8

1.45740 C 1.44940 C 1.47340 C 1.47440 C

2.4 1.1–1.9 2.5–10 1.4–2.0 0.6–0.9

1.47825 C 1.47540 C 1.46240 C 1.47140 C

0.45 1–3.5 5.7–7.3

1.46840 C 1.45840 C 1.45740 C 1.46940 C 1.48125 C

0.3–1.0 10 0.3–0.6 0.8

1.46940 C

2.5

1.47140 C 1.46260 C 1.46540 C 1.47340 C 1.46940 C 1.51725 C

0.36–1.0 0.6 9.8 0.3–1.8 11.2 2 5.4

247 191–196 175–183 196–213 179–206 193–195 153–262 187–193 194–196 191–197 190–195 188–195 173–175 195 190 185–196 200–205 220–231 186–194 188–194 191 193–195 188–193 168–179 188–203 188–193 189–194 188–193 190–197 171–174

16 97–111 84 98–110 23–41 33–42 6–10 111–128 103–111 87 145–162 175–202 99–110 71 129 140–180 79–88 49–59 26–32 88–98 185–206 83–87 128–141 121–130 94–105 122–141 103–117 122–134 129–136 163–171 94–98 125

10.76 TABLE 10.9 Constants of Waxes

Wax Bamboo leaf Bayberry (myrtle) Beeswax, ordinary Beeswax, East Indian Beeswax, white, USP Candelilla Cape berry Caranda Carnauba, No. 1 yellow Carnauba, No. 3, crude Carnauba, No. 3, refined Castor oil, hydrogenated Chinese insect Cotton Cranberry Esparto

Melting point, C 79–80 47–49 62–66 61–67 61–69 73–77 40–45 80–85 86–88 86–90 86–89 83–88 80–85 68–71 207–218 75–79

Specific gravity (15 C/15 C) 0.96125 C 0.99 0.95–0.97 0.95–0.97 0.95–0.98 0.98–0.99 1.01 0.99–1.00 0.99–1.00 0.99–1.01 0.96–0.97 0.98–0.9920 C 0.95–0.97 0.96 0.97–0.98 0.985–0.995

Refractive index

1.43680 C 1.44–1.4840 C 1.4440 C 1.45–1.4765 C 1.45–1.4685 C 1.4545 C

1.4740 C 1.4640 C

Acid value 14–15 3–4 17–21 5–10.5 17–24 19–24 2.5–4.0 5.0–9.5 1.5–2.5 3.0–8.5 3.0–5.0 1.0–5.0 2–9 32 42–59 22–27

Saponification value 43–44 205–212 88–100 87–117 90–96 55–64 211–215 64–79 75–86 75–89 76–85 177–181 78–93 71 131–134 58–73

Iodine value 7.8 4–9.5 8–11 4–10.5 7–11 14–20 0.5–2.5 8–9

7–13.5 2.5–8.5 1.0–2.5 25 44–53 7–15

Flax Japan Jojoba Microcrystalline, amber Microcrystalline, white Montan, crude Montan, refined Ouricury Ozokerite Palm Paraffin, American Shellac Sisal hemp Spermaceti Sugarcane, refined Wool

61–70 49–56 11–12 64–91 71–89 76–86 77–84 86–89 56–82 74–86 49–63 79–82 74–81 41–49 76–82 38–40

0.91–0.99 0.97–1.00 0.86–0.9025 C 0.91–0.94 0.93–0.94 1.01–1.0225 C 1.02–1.04 0.99–1.01 0.90–1.00 0.99–1.05 0.896–0.925 0.97–0.98 1.007–1.010 0.905–0.960 0.96–0.98 0.97

1.46525 C 1.42–1.4580 C 1.44180 C

1.44–1.4880 C

1.5125 C 1.4840 C

17–48 4–15 0.2–0.6 0 0 22–31 23–45 12–19 0 5–11 0 12–24 16–19 0.5–3.0 8–23 6–22

37–102 210–235 92–95 0 0 59–92 72–115 88–96 0 64–104 0 64–83 56–58 121–135 55–70 82–130

22–29 4–15 82–88 0 0 14–18 10–14 6.9–7.8 4–8 9–17 0 6–9 28–29 2.5–8.5 13–29 15–47

10.77

SECTION 11

ABBREVIATIONS, CONSTANTS, AND CONVERSION FACTORS

PHYSICAL CONSTANTS . . . . . . . . . . . . . . . . . Table 11.1 Fundamental Physical Constants . . . . . GREEK ALPHABET . . . . . . . . . . . . . . . . . . . . Table 11.2 Greek Alphabet . . . . . . . . . . . . . . PREFIXES . . . . . . . . . . . . . . . . . . . . . . . . . . Table 11.3 Prefixes for Naming Multiples and Submultiples of Units . . . . . . . . . . . Table 11.4 Numerical Prefixes . . . . . . . . . . . . . TRANSFORMATIONS . . . . . . . . . . . . . . . . . . . Table 11.5 Conversion Formulas for Solutions Having Concentrations Expressed in Various Ways Table 11.6 Conversion Factors . . . . . . . . . . . . . STATISTICS . . . . . . . . . . . . . . . . . . . . . . . . . Table 11.7 Values of t . . . . . . . . . . . . . . . . .

11.1

. . . . .

. . . . .

11.2 11.2 11.5 11.5 11.5

. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

11.5 11.5 11.6

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . . .

. . . .

. . . .

11.6 11.7 11.14 11.14

11.2

SECTION 11

PHYSICAL CONSTANTS TABLE 11.1 Fundamental Physical Constants A. Defined values Name of unit

Symbol

Definition SI base units

Meter (metre) (preferred spelling in U.S. is meter) Kilogram Second

m

1 650 763.73 wavelengths in vacuum of the orange-red line of the spectrum of krypton-86

kg s

Ampere

A

Kelvin (degree Kelvin) Candela

K cd

Mole

mol

Mass of a cylinder of platinum–iridium alloy kept at Paris Duration of 9 192 631 770 cycles of the radiation associated with a specified transition of the cesium atom Magnitude of the current that, when flowing through each of two long parallel wires separated by one meter in free space, results in a force between the two wires 2  107 newton for each meter of length Defined in the thermodynamic scale by assigning 273.16 K to the triple point of water (freezing point, 273.15 K  0 C) Luminous intensity of 1/600 000 of a square meter of a radiating cavity at the temperature of freezing platinum (2 042 K) Amount of substance which contains as many specified entities (molecules, atoms, ions, electrons, photons, etc.) as there are atoms of carbon-12 in exactly 0.012 kg of that nuclide Supplementary SI units

Radian

rad

Steradian

sr

The plane angle between two radii of a circle which cut off on the circumference an arc equal in length to the radius The solid angle which, having its vertex in the center of a sphere, cuts off an area of the surface of the sphere equal to that of a square with sides of length equal to the radius of the sphere

B. Derived SI units

Quantity and symbol Capacitance (electric), C Charge (electric), quantity of electricity, Q Conductance (electric), G( 1/R) Energy, work, quantity of heat, H

Name of SI unit

Symbol and definition

farad

F  C · V1

coulomb siemens joule

CA·s S  1 J  kg · m2 · s2

ABBREVIATIONS, CONSTANTS, AND CONVERSION FACTORS

11.3

TABLE 11.1 Fundamental Physical Constants (continued)

Quantity and symbol

Name of SI unit

Force Frequency Illuminance, illumination Inductance, L Luminous flux Magnetic flux Magnetic flux density Potential difference, E Power, radiant flux Pressure, stress Resistance (electric), R

newton hertz lux henry lumen weber tesla volt watt pascal ohm

Symbol and definition N  kg · m · s2 Hz  s1 lx  lm · m2 H·s lm  cd · sr Wb  V · s T  Wb · m2 V  kg · m2 · s3 · A1  J · A1 · s1 W  kg · m2 · s3  J · s1 Pa  N · m2  kg · m1 · s2   V · A1  kg · m2 · s3 · A2

C. Recommended Consistent Values of Constants The digits in parentheses following a numerical value represent the standard deviation of that value in terms of the final listed digits. Constant Anomalous electron moment correction Atomic mass unit Avogadro constant Bohr magneton Bohr radius Boltzmann constant Charge-to-mass ratio for electron Compton wavelength of electron Compton wavelength of neutron Compton wavelength of proton Diamagnetic shielding factor, spherical H2O molecule Electron g-factor Electron magnetic moment Electron radius (classical) Electron rest mass Elementary charge Faraday constant Fine structure constant First radiation constant Gas constant (molar)

Gravitational constant

Symbol and value

(e /0)  1  1.159 615(15)  103 u  (103 kg · mol1)/NA  1.660 566(9)  1027 kg NA  6.022 045(31)  1023 mol1 B  e/2mec  9.274 078(36)  1024 J · T1 a0  /4R∞  0.529 177 06(44)  1010 m k  R/NA  1.380 662(44)  1023 J · K1 e/me  1.758 805(5)  1011 C · kg1 2 c   /2R  2.426 309(4)  1012 m c  c /2  a0  3.861 591(6)  1013 m c,n  h/mnc  1.319 591(2)  1015 m c,p  h/mpc  1.321 410(2)  1015 m 1  (H2O)  1.000 025 64(7) ge /2  e /B  1.001 159 657(4) e  9.284 832(36)  1024 J · T1 2 c  0e /4me  re  2.817 938(7)  1015 m me  0.910 953(5)  1030 kg  5.485 803(2)  104 u e  1.602 189(5)  1019 C NAe  F  9.648 456(27)  104 C · mol1 0ce2/2h    0.007 297 351(6) 1/  1.370 360(1) 2hc2  c1  3.741 83(2)  1016 W · m2 R  P0Vm /T0  8.314 41(26) J · mol1 · K1  82.0568(26) cm3 · atm · mol1 · K1  1.987 19(6) cal · mol1 · K1 G  6.672(4)  1011 N · m2 · kg2

11.4

SECTION 11

TABLE 11.1 Fundamental Physical Constants (continued) Constant Gyromagnetic ratio of proton (uncorrected for diamagnetism of H2O) Josephson frequency–voltage ratio Magnetic flux quantum Molar standard volume, ideal gas Muon g-factor Muon magnetic moment Muon rest mass Neutron rest mass Normal volume, perfect gas Nuclear magneton Permeability of vacuum Permittivity of vacuum Planck constant Proton magnetic moment: In Bohr magnetons In nuclear magnetons Proton rest mass Quantum–charge ratio Quantum of circulation Ratio, electron to proton magnetic moments Ratio, kxu (Siegbahn) to angstrom Ratio, muon moment to proton moment Rydberg constant Second radiation constant Speed of light in vacuum Stefan–Boltzmann constant Thomson cross section Voltage–wavelength product Wien displacement constant Zeeman splitting constant Energy equivalents: 1 atomic mass unit 1 proton mass 1 neutron mass 1 muon mass 1 electron mass 1 electronvolt

Symbol and value p  2.675 199(8)  108 s1 · T1 p  675 130(8)  108 s1 · T1 2e/h  4.835 939(13)  1014 Hz · V1 0  h/2e  2.067 851(5)  1015 Wb Vm  RT0/P0  0.022 413 8(7) m3 · mol1 e/2mc  g/2  1.001 166 16(31)   4.490 474(18)  1026 J · T1 m  1.883 566(11)  1028 kg mn  1.674 954(9)  1027 kg V0  2.241 36(30)  104 cm3 · mol1 N  e/2mpc  5.050 824(20)  1027 J · T1 0  4  107 H · m1 0  (0c2)1  8.854 187 82(7)  1012 F · m1 h  6.626 176(36)  1034 J · s   h/2  1.054 589(6)  1034 J · s p  1.410 617(5)  1026 J · T1 p /B  1.521 032 209(16)  103 p /N  2.792 845 6(11) mp  1.672 649(9)  1027 kg h/e  4.135 701(11)  1015 J · Hz1 · C1 h/me  7.273 89(1)  104 J · s · kg1 e /p  6.582 106 88(7)  102  1.000 020 5(56)  /p  3.183 340(7) R∞  1.097 373 18(8)  107 m1 c2  hc/k  1.438 786(45)  102 m · K c  2.997 924 58(12)  108 m · s1   ( 2/60)k4/3c2  5.670 3(7)  108 W · m2 · K4 e  8r 2e /3  6.652 448(33)  1028 m2 V  1.239 852(3)  106 eV · m b  0.289 78(4) cm · K B /hc  4.668 58(4)  105 cm1 · G1 u  931.501 6(26) MeV mv  938.279 6(27) MeV mn  939.573 1(27) MeV m  105.659 48(35) MeV me  0.511 003 4(14) MeV 1 eV/k 1.160 450(36)  104 K 1 eV/hc  8.065 479(21)  103 cm1 1 eV/h  2.417 970(6)  1014 Hz

Source: E.R. Cohen and B.N. Taylor, J. Phys. Chem. Ref. Data, 2(4): 663 (1973)

11.5

ABBREVIATIONS, CONSTANTS, AND CONVERSION FACTORS

GREEK ALPHABET TABLE 11.2 Greek Alphabet Capital letter

Lowercase letter

Letter name



        

A B 

E Z H

I K  M

Capital letter

Lowercase letter

N O  P T Y  X  

 o         

Alpha Beta Gamma Delta Epsilon Zeta Eta Theta Iota Kappa Lambda Mu

Letter name Nu Xi Omicron Pi Rho Sigma Tau Upsilon Phi Chi Psi Omega

PREFIXES TABLE 11.3 Prefixes for Naming Multiples and Submultiples of Units For example: 109 gram is one nanogram, or 1 ng. Factor

Prefix

Symbol

Factor

Prefix

1012 10 9 106 103 10 2 10 101

tera giga mega kilo hecto deka deci

T G M k h da d

102 103 106 109 1012 1015 1018

centi milli micro nano pico femto atto

Symbol c m  n p f a

TABLE 11.4 Numerical Prefixes Number 1 2

1 1 12 2 3 4 5

Prefix hemi mono sesqui di or bi tri tetra penta

Number

Prefix

Number

Prefix

6 7 8 9 10 11 12

hexa hepta octa nona deca undeca dodeca

13 14 15 16 17 18 19

trideca tetradeca pentadeca hexadeca heptadeca octadeca nonadeca

11.6

SECTION 11

TABLE 11.4 Numerical Prefixes (continued ) Number 20 21 22 23 24 25 26 27 28 29 30 31 32 33

Prefix

Number

icosa henicosa docosa tricosa tetracosa pentacosa hexacosa heptacosa octacosa nonacosa triaconta hentriaconta dotriaconta tritriaconta

34 35 36 37 38 39 40 41 42 43 44 45 46 47

Prefix

Number

Prefix

48 49 50 51 52 53 54 55 56 57 58 59 60

octatetraconta nonatetraconta pentaconta henpentaconta dopentaconta tripentaconta tetrapentaconta pentapentaconta hexapentaconta heptapentaconta octapentaconta monapentaconta hexaconta

tetratriaconta pentatriaconta hexatriaconta heptatriaconta octatriaconta nonatriaconta tetraconta hentetraconta dotetraconta tritetraconta tetratetraconta pentatetraconta hexatetraconta heptatetraconta

TRANSFORMATIONS TABLE 11.5 Conversion Formulas for Solutions Having concentrations expressed in Various Ways Abbreviations Used in the Table wt %, weight percent of solute MW1, molecular weight of solute MW2, molecular weight of solvent d, density of solution (g · mL1)

To obtain

From

molarity

weight per cent of solute

molarity

molality

molarity

grams of solute per liter of solution

molarity

mole fraction

mole fraction

weight per cent of solute

mole fraction

molality

mole fraction

molarity

m, molality M, molarity n, mole fraction G, grams of solute per liter of solution

Compute 10 d(wt %) MW1 1000 dm M 1000  (MW1)m G M MW1 M

1000 dn n(NW1)  MW2(1  n) (wt %)/MW1 n (wt %)/MW1  (100  wt %)MW2 (MW2)m n (MW2)m  1000 M(MW2) n M(MW2  MW1)  1000 d M

ABBREVIATIONS, CONSTANTS, AND CONVERSION FACTORS

11.7

TABLE 11.5 Conversion Formulas for Solutions Having concentrations expressed in Various Ways (continued ) To obtain

From

Compute G(MW2) G(MW2  MW1)  1000 d(MW1)

grams of solute per liter of solution

n

weight percent of solute

mole fraction

wt % 

100 n(MW1) n(MW1)  MW2(1  n)

weight percent of solute

grams of solute per liter of solution

wt % 

G 10 d

weight percent of solute

molarity

wt % 

M(MW1) 10 d

weight percent of solute

molality

wt % 

100 m(MW1) 1000  m(MW1)

molality

molarity

m

1000 M 1000 d  M(MW1)

molality

grams of solute per liter of solution

m

1000 G MW1(1000 d  G)

molality

weight percent of solute

m

1000(wt %) MW1(100  wt %)

molality

mole fraction

m

1000 n MW2  n(MW2)

mole fraction

TABLE 11.6 Conversion Factors The data have been compared with the International Standard ISO 31 (1979–80) and the American Society for Testing and Materials Standard for Metric Practice E 380-79. Relations which are exact are indicated by an asterisk (*). Factors in parentheses are also exact. To convert

Into

Multiply by

ampere per square centimeter

ampere per square inch*

6.451 6

ampere-hour

coulomb*

3 600

ampere-turn

gilbert

1.256 637

angstrom

meter* nanometer*

1  1010 0.1

apostib

candela per square meter lambert*

0.318 309 9(1 ) 1  104

atmosphere

bar* inch of mercury millimeters of mercury* millimeter of water newton per square meter* pascal* torr*

1.013 25 29.921 26 760 1.033 227  104 1.013 25  105 1.013 25  105 760

11.8

SECTION 11

TABLE 11.6 Conversion Factors (continued ) To convert

Into

Multiply by

bar

atmosphere dyne per square centimeter* millimeter of mercury pascal

0.986 923 1  106 750.062 1  105

barn

square meter*

1  1028

barrel (petroleum)

gallon (British) gallon (U.S.)* liter

34.972 3 42 158.987

barrel (U.S., dry)

bushel (U.S.) liter

3.281 22 115.627 1

barrel (U.S., liquid)

gallon (U.S.) liter

31.5 119.240 5

becquerel

curie*

2.7  1011

British thermal unit (Btu)

calorie joule kilowatt-hour liter-atmosphere

251.996 1 055.056 2.930 71  104 10.412 6

bushel (U.S.)

barrel (U.S., dry) cubic foot cubic inch* gallon (U.S.) liter pint (U.S., dry) quart (U.S., dry)

0.304 765 1.244 456 2 150.42 9.309 18 3.523 907 64 32

calorie

Btu joule* liter-atmosphere

0.003 968 320 4.186 8 0.041 320 5

calorie (thermochemical)

joule*

4.184

calorie per minute

watt*

0.069 78

calorie per second

watt*

4.186 8

candela

Hefner unit lumen per steradian*

1.11 1

candela per square centimeter

candela per square foot* lambert

929.303 4 3.141 593()

carat (metric)

gram*

0.2

Celsius (Centigrade) temperature scale, C

Fahrenheit temperature scale, F

9 5

centimeter

foot inch mil

0.032 808 4 0.393 700 8 393.700 8

(C  32)  F

centimeter of mercury

pascal

1 333.22

centimeter per second

foot per second

0.032 808 4

ABBREVIATIONS, CONSTANTS, AND CONVERSION FACTORS

TABLE 11.6 Conversion Factors (continued ) To convert centimeter-dyne

Into erg* joule*

Multiply by 1 1  107

centipoise

pascal-second*

0.001

centistokes

square meter per second*

1  106

coulomb

ampere-second*

1

cubic centimeter

cubic foot liter* ounce (U.S., fluid) quart (U.S., dry) quart (U.S., liquid)

3.531 47  105 0.001 0.033 814 02 9.080 83  104 0.001 056 688

cubic centimeter per second

liter per hour*

3.6

curie

becquerel*

3.7  1010

cycle per second

hertz*

1

day (mean solar)

hour* minute* second

24 1 440 8.64  104

Debye unit

coulomb-meter

3.335 64  1030

decibel

neper

0.115 129 255

degree (angle)

circumference minute (angle)* quadrant radian

0.002 777 78(1/360) 60 0.011 111 1(1/90) 0.017 453 29(/180)

degree Celcius (Centigrade) (temperature difference), C

degree Fahrenheit, F* degree Rankine* kelvin*

1.8 1.8 1

dram (apothecaries or troy)

dram (avoirdupois)

2.194 285 7

dram (avoirdupois)

grain* gram ounce (avoirdupois)

27.343 75 1.771 845 2 0.062 5(1/16)

dram (U.S., fluid)

cubic centimeter ounce (U.S., fluid)* pint (U.S., liquid)*

3.696 691 2 0.125(1/8) 0.007 812 5(1/128)

dyne

kilogram-force newton*

1.019 716  106 1  105

dyne per square centimeter

bar* millimeter of mercury pascal

1  106 7.500 617  104 0.1

dyne-centimeter

erg* joule* newton-meter*

1 1  107 1  107

11.9

11.10

SECTION 11

TABLE 11.6 Conversion Factors (continued ) To convert

Into

Multiply by

dyne-second per square centimeter

poise* pascal-second

1 0.1

electronvolt

erg joule

1.602 19  1012 1.602 19  1019

em

millimeter

4.217 52

erg

dyne-centimeter* joule* watt-hour

1 1  107 2.777 78  1011

Fahrenheit temperature, F

Celsius temperature, C

5 9

fathom

foot*

6

fermi

meter*

1  1015

foot

centimeter* inch

30.48 12

foot-candle

lumen per square foot* lumen per square meter

1 10.763 9

foot-lambert

candela per square centimeter candela per square foot lambert

3.426 26  104 0.318 309 9 0.001 076 39

gallon (British, imperial)

gallon (U.S.) liter*

1.200 95 4.546 09

gallon (U.S.)

liter ounce (U.S., fluid)* pint (U.S., liquid)*

3.785 412 128 8

gauss

tesla* weber per square meter

1  104 1  104

(F  32)  C

gilbert

ampere-turn

0.795 775

grain

milligram*

64.798 91

gram

carat (metric)* grain ounce (avoirdupois) ounce (troy) pound ton (metric)

5 15.432 358 0.035 273 962 0.032 150 747 0.002 204 622 6 1  106

gram-force

dyne* newton*

980.665 0.009 806 65

gram-force per square centimeter

pascal*

98.066 5

gram-force-centimeter

joule*

9.806 65  105

Hefner unit

candela

0.9

hertz

cycles per second*

1

ABBREVIATIONS, CONSTANTS, AND CONVERSION FACTORS

TABLE 11.6 Conversion Factors (continued ) To convert

Into

Multiply by

hour (mean solar)

minute* second

60 3 600

inch

centimeter* foot mil* millimeter*

2.54 0.083 333 3(1/12) 1 000 25.4

joule

Btu calorie erg* liter-atmosphere newton-meter* watt-hour

9.478 170  104 0.238 845 9 1  107 0.009 869 233 1 2.777 78  104(1/3600)

kelvin temperature scale, K

Celsius scale, C

C  273.1  K

kilocalorie per second

kilowatt*

4.186 8

kilogram

ounce (avoirdupois) ounce (troy) pound ton (long) ton (metric) ton (short)

35.273 963 32.150 747 2.204 622 6 9.842 065 3  104 0.001 0.001 102 311 3

kilometer

foot light-year mile (statute)

3 280.840 1.057 02  1013 0.621 371 192

kilowatt

Btu per hour horsepower (metric) joule per hour* kilocalorie per hour

3 412.14 1.359 62 3.6  106 859.845

knot

foot per minute meter per minute mile (nautical) per hour* mile (statute) per hour

101.268 6 30.866 7 1 1.150 78

lambert

candela per square centimeter

0.318 310

liter

cubic centimeter* cubic decimeter* cubic inch gallon (U.S.) ounce (U.S., fluid) pint (U.S., liquid) quart (U.S., liquid)

1 000 1 61.023 74 0.264 172 1 33.814 02 2.113 376 1.056 688

liter per minute

gallon (U.S.) per hour

15.850 3

liter-atmosphere

Btu calorie joule*

0.096 037 6 24.201 1 101.325

11.11

11.12

SECTION 11

TABLE 11.6 Conversion Factors (continued ) To convert

Into

Multiply by

lumen per square centimeter

lux*

1  104

lux

lumen per square meter*

1

maxwell

weber*

1  108

megaohm

ohm*

1  106

meter

angstrom* foot

1  1010 3.280 839 895

mho (ohm1)

siemens*

1

micrometer (micron)

angstrom millimeter*

1  104 0.001

mil

inch* millimeter*

0.001 0.025 4

mile (statute)

foot* furlong* kilometer* mile (nautical)

5.280 8 1.609 344 0.868 976

milligram per assay ton

milligram per kilogram ounce (troy) per ton (short)*

34.285 714 1

milliliter

cubic centimeter*

1

millimeter

inch

0.039 370 8

millimeter of mercury

atmosphere dyne per square centimeter pascal torr*

0.001 315 789(1/760) 1 333.224 133.322 4 1

minute (angle)

circumference degree (angle) radian second (angle)*

4.629 63  105 0.016 666 7(1/60) 2.908 88  104 60

minute

day hour second*

6.944 444  104 0.016 666 7(1/60) 60

newton

dyne*

1  105

newton per square centimeter

pascal*

1  104

oersted

ampere per meter

79.577 5

ounce (avoirdupois)

dram* grain* gram* ounce (troy) pound*

16 437.5 28.349 523 125 0.911 458 33 0.062 5(1/16)

ounce (U.S., fluid)

cubic centimeter gallon (U.S.)* milliliter

29.573 530 0.007 812 5(1/128) 29.573 530

ABBREVIATIONS, CONSTANTS, AND CONVERSION FACTORS

TABLE 11.6 Conversion Factors (continued ) To convert

Into

Multiply by

pint (U.S., liquid)* quart (U.S., liquid)*

0.062 5(1/16) 0.031 25(1/32)

parsec

kilometer

3.085 68  1013

part per million

gram per ton (metric)* milligram per kilogram*

1 1

pascal

bar* dyne per square centimeter* inch of mercury millimeter of mercury newton per square meter*

1  105 10

pascal-second

poise*

10

pica (printer’s)

point*

12

pint (U.S., liquid)

cubic centimeter

473.176 5

2.953 00  194 7.500 62  103 1

point (printer’s, U.S.)

millimeter*

0.351 459 8

poise

pascal-second*

0.1

pound

dram* grain* gram* ounce (avoirdupois)* ton (long) ton (metric)* ton (short)*

256 7 000 453.592 37 16 4.462 285 7  104 4.535 923 7  104 5  104(1/2000)

poundal

gram-force newton

14.098 1 0.138 255

proof (U.S.)

percent alcohol by volume*

0.5

quart (U.S., dry)

cubic centimeter cubic foot pint (U.S., dry)

1 101.221 0.038 889 25 2

quart (U.S., liquid)

gallon (U.S.)* liter ounce (U.S., fluid)* pint (U.S., liquid)*

0.25 0.946 353 32 2

radian

degree (angle) minute (angle) revolution

57.295 780 3.437.75 0.159 155

ream

quire* sheet

20 480 or 500

revolution

degree (angle)*

360

revolution per minute

radian per second

0.140 720

roentgen

coulomb per kilogram*

2.58  104

second (angle)

degree radian

2.777 78  104 4.848 137  106

11.13

11.14

SECTION 11

TABLE 11.6 Conversion Factors (continued ) To convert

Into

Multiply by

siemens

mho (ohm1)*

1

steradian

sphere spherical right angle

0.079 577 5 0.636 620

stokes

square meter per second*

1  104

tablespoon (metric)

cubic centimeter*

15

teaspoon (metric)

cubic centimeter*

5

tesla

weber per square meter*

1

ton (long)

kilogram* pound* ton (metric) ton (short)*

1 016.046 908 8 2 240 1.016 046 9 1.12

torr

millimeter of mercury pascal

1 133.322 4

volt-second

weber*

1

watt

Btu per hour calorie per second erg per second* joule per second*

3.412 14 0.238 846 1  107 1

weber

maxwell*

1  108

X unit

meter

1.002 02  1013

STATISTICS TABLE 11.7 Values of t df

t.60

t.70

t.80

t.90

t.95

t.975

t.99

t.995

1 2 3 4 5

0.325 0.289 0.277 0.271 0.267

0.727 0.617 0.584 0.569 0.559

1.376 1.061 0.978 0.941 0.920

3.078 1.886 1.638 1.533 1.476

6.314 2.920 2.353 2.132 2.015

12.706 4.303 3.182 2.776 2.571

31.821 6.965 4.541 3.747 3.365

63.657 9.925 5.841 4.604 4.032

6 7 8 9 10

0.265 0.263 0.262 0.261 0.260

0.553 0.549 0.546 0.543 0.542

0.906 0.896 0.889 0.883 0.879

1.440 1.415 1.397 1.383 1.372

1.943 1.895 1.860 1.833 1.812

2.447 2.365 2.306 2.262 2.228

3.143 2.998 2.896 2.821 2.764

3.707 3.499 3.355 3.250 3.169

ABBREVIATIONS, CONSTANTS, AND CONVERSION FACTORS

11.15

TABLE 11.7 Values of t (continued) df

t.60

t.70

11 12 13 14 15

0.260 0.259 0.259 0.258 0.258

0.540 0.539 0.538 0.537 0.536

16 17 18 19 20

0.258 0.257 0.257 0.257 0.257

21 22 23 24 25

t.80

t.90

t.95

t.975

t.99

t.995

0.876 0.873 0.870 0.868 0.866

1.363 1.356 1.350 1.345 1.341

1.796 1.782 1.771 1.761 1.753

2.201 2.179 2.160 2.145 2.131

2.718 2.681 2.650 2.624 2.602

3.106 3.055 3.012 2.977 2.947

0.535 0.534 0.534 0.533 0.533

0.865 0.863 0.862 0.861 0.860

1.337 1.333 1.330 1.328 1.325

1.746 1.740 1.734 1.729 1.725

2.120 2.110 2.101 2.093 2.086

2.583 2.567 2.552 2.539 2.528

2.921 2.898 2.878 2.861 2.845

0.257 0.256 0.256 0.256 0.256

0.532 0.532 0.532 0.531 0.531

0.859 0.858 0.858 0.857 0.856

1.323 1.321 1.319 1.318 1.316

1.721 1.717 1.714 1.711 1.708

2.080 2.074 2.069 2.064 2.060

2.518 2.508 2.500 2.492 2.485

2.831 2.819 2.807 2.797 2.787

26 27 28 29 30

0.256 0.256 0.256 0.256 0.256

0.531 0.531 0.530 0.530 0.530

0.856 0.855 0.855 0.854 0.854

1.315 1.314 1.313 1.311 1.310

1.706 1.703 1.701 1.699 1.697

2.056 2.052 2.048 2.045 2.042

2.479 2.473 2.467 2.462 2.457

2.799 2.771 2.763 2.756 2.750

40 60 120 ∞

0.255 0.254 0.254 0.253

0.529 0.527 0.526 0.524

0.851 0.848 0.845 0.842

1.303 1.296 1.289 1.282

1.684 1.671 1.658 1.645

2.021 2.000 1.980 1.960

2.423 2.390 2.358 2.326

2.704 2.660 2.617 2.576

df*

t.40

t.30

t.20

t.10

t.05

t.025

t.01

t.006

*When the table is read from the foot, the table values should be prefixed with a negative sign. Interpolation should be performed using the reciprocals of the degrees of freedom. Source: Perry, Chilton, and Kirkpatrick, Chemical Engineers’ Handbook, 4th ed., McGraw-Hill, New York (1963).

Index

Index terms

Links

A Abbreviations: of elements in polymer chemistry

1.81 10.67

SI units

11.2

single-letter, of amino acids

1.44

Absolute configurations

2.2

1.58

Absorption: cross section, thermal neutron, of nuclides

3.2

frequencies, infrared

6.21

of water by plastics

10.24

Acetal polymers: description of

10.9

properties of

10.24

Acetals, nomenclature of

1.25

Acetamide azeotropes

4.43

Acetic acid binary azeotropes

4.31

Acetone azeotropes

4.42

Acetone-water solutions, reference electrode potentials in

8.79

Acetylene, solubility in water at various temperatures Acid anhydrides, nomenclature of

4.2 1.25

Acid value: of fats

10.73

of oils

10.73

of waxes

10.77

This page has been reformatted by Knovel to provide easier navigation.

I.1

I.2

Index terms Acid–water binary azeotropes

Links 4.17

Acidic dissociation constants: Hammett and Taft equations for estimation of

7.3

of indicators

8.72

of inorganic materials

8.61

of organic materials

8.3

at various temperatures

8.64

Acids, half-wave potentials

8.87

Acrylic polymers: description of

10.9

properties of

10.26

Acrylic poly(vinyl chloride) alloy polymers properties of

10.26

Acrylonitrile–butadiene–styrene (ABS) copolymers: description of

10.21

properties

10.52

Acyclic compounds, stereochemistry of

1.48

Acyl halides, nomenclature of

1.26

Acylals nomenclature of

1.25

Additives to polymers

10.5

Affinity, atomic electron

3.11

Affixes in organic nomenclature

1.22

Air, solubility in water at various temperatures

4.2

Alcohols, nomenclature of

1.26

Alcohol-water binary azeotropes

4.33

Alcohol-water ternary azeotropes

4.46

Aldehydes: half-wave potentials

8.84

infrared absorption frequencies of

6.23

nomenclature of

1.28

Aldehyde-water azeotropes

4.26

This page has been reformatted by Knovel to provide easier navigation.

I.3

Index terms Aliphatic hydrocarbons, half-wave potentials

Links 8.82

Alkanes: carbon-13, chemical shifts, effect of substituents on

6.83

carbons, estimate of chemical shifts of

6.86

infrared absorption frequencies

6.22

nomenclature of

1.2

proton chemical shifts of

6.76

Raman frequencies

6.63

Alkenes: infrared absorption frequencies of nomenclature of

6.35 1.4

proton chemical shifts of

6.79

Raman frequencies

6.63

Alkyd polymers description of

10.11

properties of

10.26

10.44

Alkynes: infrared absorption frequencies of nomenclature of

6.28 1.4

Alloy polymers: description of

10.11

properties of

10.26

Allyl alcohol binary azeotropes

4.39

Allyl alcohol-water ternary azeotropes

4.47

Allyl polymers: description of

10.11

properties of

10.28

Allyl–diglycol–carbonate polymers, properties of Alphabet, Greek

10.28 11.5

Amides: infrared absorption frequencies of

6.26

This page has been reformatted by Knovel to provide easier navigation.

10.28

I.4

Index terms

Links

Amides: (Continued) nomenclature of

1.29

Amines: infrared absorption frequencies of

6.26

nomenclature of

1.29

Amine-water azeotropes

4.26

Amino acids: International Union of Biology (IUB) single-letter codes for natural

1.44

nomenclature of

1.40

Ammonia, solubility in water at various temperatures Ammonium compounds, nomenclature of

4.2 1.30

Anhydrides: infrared absorption frequencies of

6.31

nomenclature of

1.25

Aniline azeotropes

4.44

Anions, nomenclature of organic

1.28

Antioxidants, for polymers

10.5

Antistatic agents for polymers

10.5

Aqueous vapor pressure of salt solutions Aqueous acid-base titrations, indicators for

9.3 8.72

Aqueous solution at various temperatures, equilibrium constants in Argon, solubility in water at various temperatures

8.64 4.7

Aromatic compounds: half-wave potentials of

8.82

infrared absorption frequencies of

6.39

nomenclature of Raman frequencies of Aromatic hydrocarbons, half-wave potentials Aromatic nylon (aramid) properties

1.6 6.66 8.82 10.40

This page has been reformatted by Knovel to provide easier navigation.

1.39

I.5

Index terms Aromatic polyester properties

Links 10.44

Asymmetric carbon atoms

1.54

Atomic electron affinities

3.11

Atomic weights: of elements, inside front cover of isotopes

3.2

Autoignition temperatures of fuel air mixtures

4.99

Axial atoms

1.50

Azeotropes: binary

4.25

ternary

4.46

Azo compounds: half-wave potentials of

8.92

infrared absorption frequencies of

6.36

nomenclature of

1.30

Raman frequencies of

6.64

Azoxy compounds, nomenclature of

1.31

B Basic dissociation constants (see Acidic dissociation constants) Baths, cooling

9.2

Beilstein’s Handbuch references for organic compounds

1.82

Benzene azeotropes

4.45

Benzene: azeotropes

4.45

carbon-13 chemical shifts in substituted

6.89

derivatives, substituted, wavelength calculation of ultraviolet absorption band

6.9

infrared absorption frequencies of

6.36

proton chemical shifts in monosubstituted

6.81

Raman frequencies of

6.66

This page has been reformatted by Knovel to provide easier navigation.

I.6

Index terms

Links

Benzene: (Continued) ultraviolet absorption band of substituted

6.9

Benzyl alcohol binary azeotropes

4.40

Beta radiation energies of nuclides

3.2

Binary azeotropes: with acids, organic

4.20

with alcohol

4.33

with ketones

4.42

with water

4.25

Binary azeotropic (constant-boiling) mixtures

4.25

Biological nomenclature

1.44

Bis(2-hydroxyethyl) ether

4.45

Block copolymer

10.3

properties of

10.56

Blowing agents for copolymers

10.6

Boiling points

4.12

of chromatographic solvents

9.5

of inorganic compounds

2.3

of organic compounds

1.82

molecular elevation of

4.23

for common organic solvents arranged by boiling point

4.12

(see also Critical properties) Bond dipole moments

3.30

Bond dissociation energy

3.19

Bond lengths

3.13

carbon–selenium

3.16

carbon–carbon

3.14

carbon–halogen

3.14

carbon–hydrogen

3.14

carbon–nitrogen

3.15

carbon–oxygen

3.15

This page has been reformatted by Knovel to provide easier navigation.

I.7

Index terms

Links

Bond lengths (Continued) carbon–silicon

3.16

carbon–sulfur

3.16

Bonds: ionic character of

3.10

properties of

3.13

strengths of

3.19

stretching force constant of

3.10

Boron: bond lengths

3.17

strengths

3.20

Boron-11 chemical shifts

6.96

Boron compounds: infrared absorption frequencies

6.44

nomenclature of

1.31

Bragg equation

6.123

Bridged hydrocarbons, nomenclature of

1.10

Britton-Robinson pH buffer

8.76

Bromine: bond strengths solubility in water at various temperatures Buffer solutions

3.20 4.2 8.74

Britton–Robinson system

8.76

for control purposes, pH values of

8.76

McIlvaine buffer

8.76

Prideaux–Ward mixture

8.76

Buffer pH reference standards

8.75

Burning rate of plastics

10.24

Butadiene–maleic acid copolymers, properties of

10.44

Butadiene rubber

10.61

Butane, conformations of

1.49

This page has been reformatted by Knovel to provide easier navigation.

10.64

I.8

Index terms

Links

1-Butanol binary azeotropes

4.37

1-Butanol-water ternary azeotropes

4.47

2-Butanol-water ternary azeotropes

4.47

2-Butanone azeotropes

4.43

2-Butoxyethanol, binary azeotropes

4.41

Butylene polymer: description of

10.18

properties of

10.48

Butylene terephthalate plastic: description of

10.17

properties of

10.42

Butyric acid binary azeotropes

4.32

C Calomel electrode, saturated Cambridge Structural Database

8.82 6.124

Capacity, heat (see Heat capacities of organic compounds) Capture cross section of nuclides, thermal neutron

3.2

Carbon dioxide, solubility in water at various temperatures

4.3

Carbon bond strengths

3.20

Carbon–carbon bond lengths

3.14

Carbon–carbon spin coupling constants

6.93

Carbon dioxide: permeability of polymers and rubbers to solubility in water at various temperatures

10.70 4.3

Carbon–fluorine spin coupling constants

6.95

Carbon–halogen bond lengths

3.14

Carbon–hydrogen bond lengths

3.14

one-bond

6.92

two-bond

6.93

This page has been reformatted by Knovel to provide easier navigation.

I.9

Index terms Carbon–hydrogen spin coupling constants one-bond Carbon monoxide, solubility in water at various temperatures Carbon–nitrogen bond lengths

Links 6.93 6.92 4.3 3.15

Carbon–nitrogen double bonds: infrared absorption frequencies of

6.37

Raman frequencies of

6.60

Carbon–oxygen bond lengths

3.15

Carbon–oxygen bonds, infrared absorption frequencies of

6.31

Carbon–selenium bond lengths

3.16

Carbon–silicon bond lengths

3.16

Carbon–carbon single bonds, Raman frequencies of

6.54

Carbon–sulfur bond lengths

3.16

Carbon-13 chemical shifts

6.89

alkyl effect of substituent groups on

6.87

in benzenes substituted

6.89

of carbon attached to double bond

6.88

of carbonyl group

6.91

of deuterated solvents

6.95

in pyridines, substituted

6.90

Carbon-13 spin coupling constants with various nuclei

6.96

Carbonyl group: carbon-13 chemical shifts of

6.91

infrared absorption frequencies of

6.31

Raman frequencies of

6.61

Carboxylic acids, nomenclature of

1.31

Cellulose-acetate-butyrate resin: description of

10.12

properties of

10.30

Cellulose acetate polymers: description of

10.11

This page has been reformatted by Knovel to provide easier navigation.

6.95

I.10

Index terms

Links

Cellulose acetate polymers: (Continued) properties of

10.28

Cellulose-acetate-propionate resins: description of

10.12

properties of

10.30

Cellulose nitrate resins: description of

10.12

properties of

10.30

Cellulosic polymers: description of

10.11

properties of

10.28

Chain-transfer agents for polymers

10.5

Characteristic groups for substitutive nomenclature

1.19

Chemical Abstracts indexing system

1.60

Chemical blowing agents for polymers

10.6

Chemical bonds, dissociation energy of

3.19

Chemical nomenclature, organic

1.2

Chemical properties: of polymers

10.24

of rubbers

10.60

Chemical Resistance of polymers and rubbers

10.65

Chemical shifts, NMR (nuclear magnetic resonance): of boron-11

6.96

of carbon-13

6.83

of fluorine-19

6.102

of nitrogen-15 (or14)

6.97

of protons

6.76

reference compounds

6.75

residual, in deuterated solvents

6.75

of silicon-29

6.104

Chiral centers

1.54

This page has been reformatted by Knovel to provide easier navigation.

I.11

Index terms Chiral compounds Chlorinated polyether properties

Links 1.55 10.30

Chlorine: bond strengths solubility in water at various temperatures

3.22 4.3

Chloroprene rubber

10.60

Chlorosulfonated polyethylene rubber

10.60

properties of

10.64

Chlorotrifluoroethylene polymer: description of

10.14

properties of

10.32

Chromatographic solvents, properties of

9.6

Chromophores, electronic absorption bands of

6.5

Coefficient of linear thermal expansion of plastics Color changes of acid-base indicators Cis-Polybutadiene rubber (BR)

10.24 8.72 10.61

Combustible mixture in air, properties of

4.99

Compressibility factor, critical

5.75

Compressive modulus of plastics

10.24

Compressive strength of plastics

10.24

Concentration of solutions, conversion formulas for

11.6

Conformational isomers

1.47

Conjunctive nomenclature

1.23

Constant-boiling mixtures: binary

4.25

ternary

4.46

Constant humidity, solutions for maintaining Conversion factors Cooling mixtures Coordination bonds, dipole moments of

9.3 11.7 9.2 3.30

This page has been reformatted by Knovel to provide easier navigation.

10.64

I.12

Index terms

Links

Copolymerization

10.3

Coupling agents for polymers

10.5

Coupling constants, spin-spin: carbon–carbon

6.93

carbon–fluorine

6.94

carbon–hydrogen: one-bond

6.92

two-bond

6.93

carbon–nitrogen

6.102

electron

6.110

fluorine–nitrogen

6.102

proton–fluorine

6.81

proton–nitrogen

6.101

proton–proton

6.80

Critical properties

5.75

compressibility factor

5.75

density

5.75

estimation of

5.88

molar volume

5.75

pressure

5.75

temperature

5.75

Cross section of nuclides, thermal neutron Cryoscopic constants

3.2 4.52

Cumulated double bonds: infrared absorption frequencies of

6.29

Raman frequencies of

6.60

Curing of polymers Cyclic aliphatic hydrocarbons, nomenclature of Cyclic compounds, stereochemistry

10.7 1.5 1.49

Cyclic hydrocarbons with side chains nomenclature of

1.11

This page has been reformatted by Knovel to provide easier navigation.

I.13

Index terms

Links

Cyclic polyethers, nomenclature of

1.32

Cyclohexane, conformations of

1.50

Cyclohexanol azeotropes

4.39

D Decay of radionuclides Deflection of temperature, under flexural load, of plastics Dendrimers

3.2 10.24 10.4

Density: critical

5.75

of organic compounds

1.82

of inorganic compounds

2.3

of solvents

9.7

Depression of melting point, molecular Desiccants

4.52 9.4

Deuterated solvents: carbon-13 chemical shifts of

6.83

proton chemical shifts of

6.76

Deuterium oxide, vapor pressure

4.12

Diallyl phthalate polymers: description of

10.11

properties of

10.28

Dielectric constant: common solvents

4.55

of inorganic compounds

4.94

of plastics Dielectric strength of plastics

10.24 10.24

Dienes, ultraviolet absorption wavelengths of

6.7

Dienones, ultraviolet absorption wavelengths of

6.7

Diglycol carbonate–allyl copolymer, properties of 1,4-Dioxane-water mixtures, reference electrodes for

10.28 8.79

This page has been reformatted by Knovel to provide easier navigation.

I.14

Index terms Dipole moments

Links 4.56

bond

3.30

group

3.31

of inorganic compounds

4.94

Dissipation factor (electrical) of plastics

10.24

Dissociation constants (see Acidic dissociation constants) Double bonds, cumulated: infrared absorption frequencies of

6.35

Raman frequencies of

6.60

Dry ice, cooling mixtures made from

9.2

Drying agents

9.4

Durometer (or Shore) hardness: of plastics

10.24

of rubbers

10.64

Dyestuffs, half-wave potentials of

8.93

E E(trans) configuration

1.53

Ebullioscopic constants

4.23

Eclipsed conformation

1.49

Elastomers

10.2

Electric quadrupole moments of elements

6.72

Electical properties of plastics

10.24

Electrode potentials

8.80

of half-reactions

8.80

(see also Half-wave potentials of organic compounds) Electrodes reference: for aqueous solutions

8.77

water-organic solvent mixtures

8.79

Electron affinities: of elements

3.11

This page has been reformatted by Knovel to provide easier navigation.

I.15

Index terms

Links

Electron affinities: (Continued) of molecules

3.12

of radicals

3.13

Electron conversion energy of nuclides

3.2

Electron paramagnetic resonance (EPR)

6.110

Electron spin resonance (ESR)

6.110

Electronegativities of the elements: of the groups Pauling’s

3.10 3.9

Electronegativity

3.9

Electronic absorption bands

6.5

Elements: electron affinities of

3.11

electronegativities of

3.9

nuclear properties of

6.73

physical properties of

2.2

Elevation of boiling point

4.23

Elongation: of plastics

10.24

of rubbers

10.64

Emission wavelength: of fluorescing compounds

6.11

of phosphorescing compounds

6.17

Enantiomers

1.55

Energies of radiation emanating from nuclides

3.2

Enones, ultraviolet-visible absorption wavelength of

6.7

Enthalpies of organic compounds: formation

5.2

of melting

5.44

of sublimation

5.44

of transition

5.44

This page has been reformatted by Knovel to provide easier navigation.

I.16

Index terms

Links

Enthalpies of organic compounds: (Continued) of vaporization Entropies of organic compounds Epichlorohydrin rubbers properties of

5.44 5.2 10.60 10.64

Epoxy polymers: description of

10.12

properties of

10.30

Equatorial atoms

1.50

Equilibrium constants

8.2

Ester-water azeotropes

4.27

Esters: infrared absorption frequencies of

6.32

nomenclature of

1.39

Ethane, solubility in water at various temperatures

4.3

1,2-Ethanediol binary azeotropes

4.41

1,2-Ethanediol monoacetate binary azeotropes

4.42

Ethanol binary azeotropes

4.34

Ethanol-water mixtures: reference electrode for

8.79

ternary azeotropes

4.46

Ethers: infrared absorption frequencies of

6.40

nomenclature of

1.32

Raman frequencies of

6.69

Ether-water azeotropes

4.28

2-Ethoxyethanol binary azeotropes

4.40

Ethyl cellulose plastics: description of

10.12

properties of

10.30

Ethylene glycol-water mixtures, reference electrode for

8.79

This page has been reformatted by Knovel to provide easier navigation.

10.32

I.17

Index terms

Links

Ethylene polymers: description of

10.8

properties of

10.46

Ethylene, solubility in water at various temperatures

4.3

Ethylene-chlorotrifluoro-ethylene copolymer properties

10.34

Ethylene-propylene-diene rubber (EPDM)

10.61

Ethylene terephthalate plastic: description of

10.17

properties of

10.42

Ethylene-tetrafluoroethylene copolymer: description of

10.14

properties of

10.34

Ethylene-vinyl acetate copolymer: properties of

10.46

Excitation wavelength: of fluorescing compounds

6.11

of phosphorescing compounds

6.17

Expansion, thermal, coefficient of linear plastics

10.24

F Fats, constants of

10.73

Flame retardants for polymers

10.6

Flammable limits for mixtures in air

4.99

Flash point of organic compounds

1.82

Flexural modulus and strength of plastics

10.24

Fluorescence: excitation wavelengths

6.11

quantum yields

6.17

Fluorinated ethylene-propylene resin: description of

10.13

properties of

10.34

This page has been reformatted by Knovel to provide easier navigation.

I.18

Index terms

Links

Fluorine bond strengths

3.22

Fluorine–carbon spin coupling constants

6.94

Fluorine–fluorine spin coupling constants

6.102

Fluorine-19 chemical shifts

6.102

Fluorine-19 to fluorine-19 spin coupling constants

6.104

Fluorine–nitrogen spin coupling constants

6.102

Fluoroalkoxy resin: description of

10.13

properties of

10.32

Fluorocarbon polymers: description of

10.13

properties of

10.32

Fluoroelastomers, properties of

10.64

Foaming agents for polymers

10.6

Force constant, bond stretching

3.10

Formic acid binary azeotropes

4.30

Formula index empirical for organic compounds

1.61

Formula weights: of inorganic compounds of organic compounds

2.3 1.82

Free energies of formation of organic compounds

5.2

Free energy relationships, linear

7.2

Freezing mixtures

4.52

Freezing point, molecular lowering of

4.52

Fuel-air mixtures, autoignition temperatures and flammable limits

4.99

Functional compounds: conjunctive nomenclature

1.23

radicofunctional nomenclature

1.24

replacement nomenclature

1.24

substitutive nomenclature

1.19

This page has been reformatted by Knovel to provide easier navigation.

I.19

Index terms Fundamental physical constants Fused polycyclic hydrocarbons, nomenclature of

Links 11.2 1.7

Fusion, latent heats of (see Melting, enthalpy of)

G Gallium bond strength

3.23

Gamma radiation energies and intensities of nuclides

3.2

Gas chromatography, McReynolds constants

9.9

Gas permeability for polymers and rubbers

10.70

Gases: drying agents for

9.4

flammability limits of

4.99

ignition temperatures of

4.99

solubility in water at various temperatures Geometrical isomerism Gibbs energies of formation of organic compounds

4.3 1.52 5.2

Government rubber I (GR-I), properties of

10.64

Government rubber nitrile (GNR)

10.60

Government rubber styrene (GRS)

10.63

Graft copolymers

10.3

Greek Alphabet

11.5

Group dipole moments

3.31

Gutta percha properties of

10.60 10.64

H Half-life of nuclides

3.2

Half-wave potentials of organic compounds

8.82

Halogen bond lengths

3.14

Halogen compounds: half-wave potentials

8.88

This page has been reformatted by Knovel to provide easier navigation.

I.20

Index terms

Links

Halogen compounds: (Continued) infrared absorption frequencies of

6.45

nomenclature of

1.35

Raman frequencies of

6.70

Halogenated hydrocarbon-water binary azeotropes

4.26

Hammett equations: defined

7.2

pKA values for

7.8

reaction parameters for

7.8

Hammett sigma constants, special Hammett substituent constants

7.10 7.3

Hardness: of plastics

10.24

of rubber

10.64

Heat capacities of organic compounds

5.2

Heats, latent, of organic compounds: of formation

5.2

of melting

5.44

of sublimation

5.44

of vaporization

5.44

Helium: permeability of polymers and rubbers to solubility in water at various temperatures

10.70 4.7

Heteroaromatics, substituted, ultraviolet absorption band

6.9

Heterocyclic compounds containing nitrogen, half-wave potentials

8.91

Heterocyclic systems: nomenclature of

1.12

Raman frequencies of

6.71

Humidification

9.2

Humidity controlled by salt solution

9.3

This page has been reformatted by Knovel to provide easier navigation.

I.21

Index terms

Links

Hydrazines, half-wave potentials

8.92

Hydrocarbon ring assemblies, nomenclature of

1.11

Hydrocarbon-water binary azeotropes

4.28

Hydrocarbons: half-wave potentials: aliphatic aromatic nomenclature of Hydrodylamines, nomenclature of

8.82 8.82 1.2 1.35

Hydrogen: bond lengths

3.17

bond strength

3.23

permeability of polymers and rubbers to single bonds to: to infrared absorption frequencies of Raman frequencies of solubility in water at various temperatures Hydrogen bromide, solubility in water at various temperatures

10.70 6.21 6.54 4.3 4.7

Hydrogen–carbon bonds: infrared absorption frequencies of

6.21

Raman frequencies of

6.54

Hydrogen–carbon spin coupling constants: one-bond

6.93

two-bond

6.93

Hydrogen chloride, solubility in water at various temperatures Hydrogen–fluorine spin coupling constants

4.7 6.81

Hydrogen–nitrogen bonds: infrared absorption frequencies of

6.26

Raman frequencies of

6.58

Hydrogen sulfide, solubility in water at various temperatures

4.5

Hydroxyl group: infrared absorption frequencies of

6.25

Raman frequencies of

6.57

This page has been reformatted by Knovel to provide easier navigation.

I.22

Index terms

Links

Hydroxylamines: half-wave potentials of Hyperfine splitting constants

8.92 6.111

I Ignition temperatures of combustible mixtures in air

4.99

Imide polymers: description of

10.17

properties of

10.44

Imines infrared absorption frequencies of

6.26

nomenclature of

1.35

Impact strength of plastics Index, empirical formula, of organic compounds

10.24 1.61

Index of refraction (see Refractive index) Indicators: acid-base, characteristics of

8.72

half-wave potentials of

8.92

Infrared absorption frequencies: of alkanes

6.22

of alkenes

6.35

of aromatic compounds

6.37

of azo compounds

6.37

of carbon–nitrogen double bonds

6.35

of carbonyl bonds

6.31

of cumulated double bonds

6.29

of ethers

6.40

of halogen compounds

6.45

of hydroxyl groups

6.25

of inorganic ions

6.46

of nitro compounds

6.36

This page has been reformatted by Knovel to provide easier navigation.

I.23

Index terms

Links

Infrared absorption frequencies: (Continued) of nitrogen–hydrogen bonds

6.26

of peroxides

6.40

of phosphorus compounds

6.42

of silicon compounds

6.43

of single bonds to hydrogen

6.21

of sulfur compounds

6.41

of triple bonds

6.28

Infrared, near, absorption frequencies in

6.47

Infrared transmitting materials

6.49

Inhibitors for polymers

10.7

Inorganic compounds: boiling points of

2.1

density of

2.1

melting points of

2.1

physical constants of solubility of Inorganic ions, infrared absorption frequencies of

4.94 2.1 6.46

International system of units (SI): base units

11.2

conversion factors for

11.7

derived units

11.2

International Union of Pure and Applied Chemistry (IUPAC) nomenclature of organic compounds values of physical constants

1.2 11.3

International Union of Biology (IUB) single-letter codes for natural amino acids Iodine bond strengths

1.44 3.26

Iodine value: of fats

10.73

This page has been reformatted by Knovel to provide easier navigation.

I.24

Index terms

Links

Iodine value: (Continued) of oils

10.73

of waxes

10.77

Iodine–nitrogen bond

3.26

Ionic character of a bond

3.10

Ionization constants: of acids of indicators

8.3

8.61

8.72

Ionization potentials: of molecular species

6.114

of radical species

6.122

Ionomers

10.19

Isobutylene rubber

10.61

Isobutene-isoprene rubber (IIR), properties of

10.64

Isobutyric acid binary azeotropes

4.33

IUB (International Union of Biology): single-letter codes for natural amino acids

1.44

IUPAC, (International Union of Pure and Applied Chemistry) nomenclature of organic compounds values of physical constants

1.2 11.3

K Ketenes, nomenclature of

1.36

Ketone-water binary azeotropes

4.29

Ketones: half-wave potentials of

8.85

nomenclature of

1.36

Kovats retention indices

9.9

Krypton, solubility in water at various temperatures

4.7

This page has been reformatted by Knovel to provide easier navigation.

10.64

I.25

Index terms

Links

L Lactams, nomenclature of

1.38

Lactides, nomenclature of

1.38

Lactims, nomenclature of

1.38

Lactones, nomenclature of

1.38

Latent heats of organic compounds

5.44

Lead, bond strength

3.27

Life, half-, of nuclides Lifetimes, phosphorescence

3.2 6.17

Linear free energy relationships

7.2

Liquid chromatography, solvents for, properties of

9.5

Liquid nitrogen, slush baths

9.2

Lithium bond strengths

3.27

Lubricants for polymers

10.7

Lydersens’ critical property increments

5.88

M McIlvaine buffer

8.84

McReynolds’ constants (gas chromatography)

9.9

Mass, exact, of nuclides

3.2

Mechanical properties of plastics

10.24

Melamine formaldehyde polymers: description of

10.14

properties of

10.34

Melting, enthalpy of

5.44

Melting point: of inorganic compounds

2.3

molecular lowering of, cryoscopic constants

4.52

of organic compounds

1.82

of waxes

10.76

This page has been reformatted by Knovel to provide easier navigation.

I.26

Index terms

Links

Mercury: bond strengths vapor pressure at various temperatures

3.27 4.8

Mercury–mercury (I) chloride reference electrodes, potentials of: in aqueous solutions

8.78

in organic solvent–water mixtures

8.79

Meso compounds Methane, solubility in water at various temperatures

1.56 4.5

Methanol binary azeotropes

4.33

Methanol-water mixtures, reference electrodes for

8.79

Methanol-water ternary azeotropes

4.46

Methine protons, chemical shift of

6.76

Methyl methacrylate polymers: description of

10.9

properties of

10.26

Methyl protons, chemical shift of

6.76

3-Methyl-1-butanol, binary azeotropes

4.38

3-Methyl-1-butanol-water ternary azeotropes

4.47

2-Methyl-1-propanol-water ternary azeotropes

4.47

2-Methyl-2-propanol binary azeotropes

4.37

2-Methyl-2-propanol-water ternary azeotropes

4.47

Methylene protons, chemical shift of

6.76

Modes of decay of nuclides

3.2

Molar volume, critical

5.75

Molecular elevation of the boiling point

4.23

Molecular lowering of the melting (freezing) point

4.52

Molecules, electron affinity of

3.12

Monocyclic aliphatic hydrocarbons, nomenclature of

1.6

Monocyclic aromatic compounds, nomenclature of

1.6

Multiples of units, prefixes

11.5

This page has been reformatted by Knovel to provide easier navigation.

I.27

Index terms

Links

N National Institute of Standards and Technology reference pH buffer solutions

8.74

standard pH buffer solutions, compositions of

8.75

Natural abundance: of elements

3.6

of nuclides

3.2

Natural rubber Near infrared absorption frequencies -

10.60 10.66 6.47

Negatron (β ) radiation energies of nuclides

3.2

Neon, solubility in water at various temperatures

4.7

Neutron absorption cross section, thermal, of nuclides

3.2

Newman projections Nitric oxide, solubility in water at various temperatures Nitrile resins properties of

1.48 4.5 10.14 10.36

Nitrile rubber (butadiene-acrylonitrile rubber) (NBR, GRN, Buna N) properties of

10.60 10.64

Nitriles: nomenclature of

1.38

Raman frequencies of

6.59

Nitrile-water binary azeotropes

4.29

Nitro and nitroso compounds: half-wave potentials of

8.89

infrared absorption frequencies of

6.36

Nitrogen bond lengths permeability of polymers and rubbers to solubility in water at various temperatures

3.26 3.17 10.70 4.5

This page has been reformatted by Knovel to provide easier navigation.

10.64

I.28

Index terms Nitrogen-15 (or 14) chemical shifts for standards

Links 6.97 6.101

Nitrogen-15 to carbon-13 spin coupling constants

6.102

Nitrogen-15 to fluorine-19 spin coupling constants

6.102

Nitrogen-15 to hydrogen-1 spin coupling constants

6.101

Nitrogen–hydrogen bonds, infrared absorption frequencies of

3.36

Nitrogen–oxygen double bonds, Raman frequencies of

6.64

Nitrous oxide, solubility in water at various temperatures

4.7

Nomenclature of organic compounds

1.2

Novolac (epoxy) resins: description of

10.12

properties of

10.32

Nuclear Magnetic Resonance (NMR) (see Chemical Shifts, NMR) Nuclear magnetic resonance spectroscopy solvents

6.71 6.75

Nuclear magneton

6.72

Nuclear properties of the elements

6.72

Nuclear quadrupole moments

6.72

Nuclear radiations and energies Nuclear spins Nuclides, properties of

3.2 6.72 3.2

Numbering of organic compounds

1.22

Numerical prefixes

11.5

Nylon 6, 11, and 12: description of

10.15

properties of

10.38

Nylon 6/6, 6/9, and 6/12: description of

10.15

properties of

10.38

This page has been reformatted by Knovel to provide easier navigation.

I.29

Index terms

Links

O Oils

10.73

constants of

10.73

Optical activity

1.54

Organic acids-water binary azeotropes

4.23

Organic ring systems, names and numbering of

1.5

Organic solvent-water mixtures, reference electrode potentials at various temperatures Organic solvents: arranged by boiling points

4.12

physical constants of

4.55

Osmium–nitrogen bond

3.26

Oximes: half-wave potentials of

8.92

nomenclature of

1.35

Oxygen: bond lengths

3.18

bond strengths

3.26

permeability of polymers and rubbers to solubility in water at various temperatures Oxygen–nitrogen bond Ozone, solubility in water at various temperatures

10.70 4.5 3.26 4.7

P Pauling electronegativities Peptides, extended arrangements of

3.9 1.59

Periodic table, inside front cover Permeability constants, gas, for polymers and rubbers

10.70

Peroxides: half-wave potentials of

8.93

infrared absorption frequencies of

6.40

This page has been reformatted by Knovel to provide easier navigation.

I.30

Index terms

Links

Peroxides: (Continued) nomenclature of

1.39

pH-buffer solutions: general purpose

8.76

National Bureau of Standards (US) reference

8.74

standard reference

8.75

Phenol binary azeotropes

4.39

Phenolic polymers: description of

10.15

properties of

10.36

Phenols, nomenclature of

1.26

Phosphorescence spectroscopy

6.17

Phosphorus: bond lengths

3.18

bond strengths

3.27

Phosphorus compounds: infrared absorption frequencies of

6.42

nomenclature of

1.39

Phosphorus-31: chemical shifts of

6.105

spin coupling constants

6.108

Photoluminescence

6.10

Physical constants of organic compounds

1.80

Physical properties of pure substances

1.61

pKA values: for Hammett equation

7.8

of organic materials

8.3

for Taft equation

7.10

Plastic families

10.7

Plastic flow

10.7

This page has been reformatted by Knovel to provide easier navigation.

I.31

Index terms

Links

Plastic materials: chemical resistance of formulas

10.60 10.9

gas permeability of

10.70

properties of

10.24

Plasticizers for polymers

10.7

Plastics, commercial properties of

10.24

Polarographic half-wave potentials

8.82

Poly (amide-imide) polymers: description of

10.16

properties of

10.40

Poly(aryl ether), properties of

10.42

Poly(butylene terephthalate), properties of

10.42

Poly(ether sulfone) polymers, properties of

10.54

Poly(ethylene terephthalate), properties of

10.42

Poly(ethylene-propylene-diene) (EPDM), properties of

10.64

Poly(methylpentene) polymers: description of

10.18

properties of

10.46

Poly(phenyl sulfone) polymers, properties of

10.54

Poly(phenylene sulfide) polymers: description of

10.19

properties of

10.48

Poly(vinyl acetate) polymers: properties of Poly(vinyl chloride) properties of

10.56 10.22

10.62

10.56

10.64

Poly(vinylidene fluoride) properties

10.34

Polyacrylate

10.61

properties of

10.64

This page has been reformatted by Knovel to provide easier navigation.

I.32

Index terms

Links

Polyamide polymers: description of

10.15

properties of

10.38

Polybutadiene rubber (BR), properties of

10.64

Polycarbonate acrylonitrile–butadiene–styrene alloy, properties of

10.28

Polycarbonate polymers: description of

10.16

properties of

10.42

Polychloroprene (Neoprene)

10.61

properties of

10.64

Polyester polymers: description of

10.17

properties of

10.56

Polyethers, nomenclature of

1.32

Polyethylene polymers, properties of

10.46

Polyimide polymer, properties of

10.44

Polyisobutylene (butyl rubber)

10.61

(Z)-polyisoprene (synthetic natural rubber)

10.62

properties of

10.64

10.64

Polymers: additives to

10.5

chemical resistance

10.65

gas permeability constants

10.70

plastic families

10.7

rubbers

10.60

types of

10.2

vapor permeability constants

10.73

Polyolefin polymers: description of

10.18

properties of

10.46

This page has been reformatted by Knovel to provide easier navigation.

10.56

I.33

Index terms

Links

Polypropylene polymers, properties of

10.48

Polystyrene polymers, properties of

10.52

Polysulfide rubbers

10.62

Polysulfone polymers, properties of

10.54

Polyurethane polymers: description of

10.19

properties of

10.50

Prefixes, numerical

11.5

1-Propanol binary azeotropes

4.35

2-Propanol binary azeotropes

4.36

2-Propanol-water mixtures, reference electrode for

8.79

1-Propanol-water ternary azeotropes

4.46

2-Propanol-water ternary azeotropes

4.46

Propanoic acid binary azeotropes

4.31

Protein Data Bank (PDB)

6.124

Proteins, extended arrangements of

1.59

Proton attached to a double bond, estimation of chemical shift of

6.80

Proton–carbon spin coupling constants: one-bond

6.92

two-bond

6.93

Proton chemical shifts: of reference compounds

6.74

of residual protons in deuterated solvents

6.74

table

6.76

Proton–nitrogen spin coupling constants Proton–proton spin coupling constants

6.102 6.82

Proton-transfer equilibrium constants: of inorganic materials of organic materials at various temperatures Pyridine azeotropes

8.61 8.2 8.64 4.44

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10.64

I.34

Index terms

Links

Pyridines: carbon-13 chemical shifts in substituted nitrogen-15 chemical shifts in monosubstituted

6.90 6.100

Q Quadrupole moments, electric, of nuclides

6.72

Quantum yield values in fluorescence

6.17

Quinones, half-wave potentials of

8.87

R Radiations emitted by nuclides

3.2

Radicals: electron affinity of ionization potentials of from ring systems, nomenclature of Radon, solubility in water at various temperatures

3.13 6.121 1.11 4.7

Raman frequencies: of alkenes

6.63

of aromatic compounds

6.66

of azo compounds

6.64

of carbon single bonds

6.54

of carbonyl bands

6.61

of cumulated double bonds

6.60

of ethers

6.69

of halogen compounds

6.70

of heterocyclic rings

6.71

of hydrogen single bonds

6.54

of nitro compounds

6.64

of nitrogen–oxygen double bonds

6.64

of sulfur compounds

6.67

of triple bonds

6.59

Raman spectroscopy

6.54

This page has been reformatted by Knovel to provide easier navigation.

I.35

Index terms Rayon

Links 10.12

Reaction parameter: in linear free energy relationships

7.2

values for Hammett equation

7.8

values for Taft equation

7.10

Reference compounds: for fluorescence quantum yield values

6.17

for fluorine-19 NMR

6.103

for nitrogen-15 NMR

6.97

for pH buffers

8.64

for proton NMR

6.79

Reference electrodes: for aqueous solutions

8.77

for organic solvent-mixtures

8.79

potentials as a function of temperature

8.77

Refractive index: of chromatographic solvents

9.6

of fats

10.73

of oils

10.73

of organic compounds of solvent pairs of waxes Relative humidity of salt solutions at various temperatures Replacement nomenclature

1.82 9.7 10.77 9.3 1.24

Rubbers: chemical resistance

10.66

formulas and advantages of

10.60

gas permeability constants

10.70

properties of natural and synthetic

10.64

synthetic Ruthenium bond strengths

10.2 3.28

This page has been reformatted by Knovel to provide easier navigation.

I.36

Index terms

Links

S Salts: of acids, nomenclature of and dry ice, cooling mixtures made from Saponification value of fats, oils and waxes Selenium bond strengths Separation methods

1.39 9.2 10.73 3.28 9.6

SI system (Systeme International d’ Unites): abbreviations

11.2

base units

11.2

conversion factors for

11.7

derived

11.2

supplementary

11.2

Sigma constants for Hammett equation

7.10

Silicon: bond lengths

3.18

bond strengths

3.28

Silicon compounds: infrared absorption frequencies of

6.43

nomenclature of

1.41

Silicon-29 chemical shifts

6.104

Silicone polymers: description of

10.20

properties of

10.50

Silicone rubbers

10.62

properties of

10.64

Silver–silver halide reference electrodes, potentials at various temperatures: for aqueous solutions

8.77

for organic solvent-water mixtures

8.79

Slush baths, dry ice or liquid nitrogen

9.2

This page has been reformatted by Knovel to provide easier navigation.

I.37

Index terms Sodium bond strengths Solidification points of fats, and oils

Links 3.29 10.73

Solubility: of gases in water at various temperatures

4.2

of inorganic compounds

2.2

of organic compounds

1.82

Solutions: concentration conversion formulas

11.6

for maintaining constant humidity

9.3

Solvent correction for ultraviolet absorption wavelengths

6.8

Solvent strength parameter (adsorption chromatography)

9.5

Solvents: for chromatography, properties of deuterated, chemical shifts of: carbon-13 proton

9.5 6.95 6.76

infrared transmission characteristics of

6.51

organic, arranged by boiling points

4.12

with same refractive index and same density

9.7

spectrograde, ultraviolet cutoffs of

6.6

Specific functional groups

1.25

Specialist nomenclature for heterocyclic systems

1.12

Specific gravity: of fats

10.73

oils

10.73

plastics

10.24

rubbers

10.64

waxes

10.77

Specific heat: of organic compounds at various temperatures of plastics

5.2 5.44 10.24

This page has been reformatted by Knovel to provide easier navigation.

I.38

Index terms

Links

Specific rotation

1.52

Spin of nuclides

6.72

Spin coupling constants: carbon-13

6.96

carbon–carbon

6.93

carbon–fluorine

6.94

carbon–hydrogen: one-bond

6.92

two-bond

6.93

carbon–nitrogen

6.102

electron

6.110

fluorine–nitrogen

6.102

fluorine–proton

6.81

fluorine-19 to fluorine-19

6.104

nitrogen-15 to carbon-13

6.102

nitrogen-15 to fluorine-19

6.102

nitrogen-15 to hydrogen-1

6.101

nitrogen–proton

6.101

phosphorus-31

6.108

proton

6.82

proton–proton

6.80

Spin–spin coupling

6.111

Staggered conformation

1.48

Standards (see Reference compounds) Stationary phases in gas chromatography, McReynolds constants Statistics, t-values in Stereochemistry in biological systems Student t-values

9.10 11.14 1.47 1.59 11.14

Styrene–acrylonitrile (SAN) copolymers: description of

10.21

properties of

10.54

This page has been reformatted by Knovel to provide easier navigation.

I.39

Index terms

Links

Styrene–butadiene Rubber (GRS, SBR, Buna S) description of

10.63

properties of

10.64

Styrene–butadiene–styrene block copolymers,

10.22

Styrene–maleic acid copolymer, properties of

10.44

Styrene polymers: description of

10.21

properties of

10.50

Submultiples of units, prefixes

11.5

Substitutive nomenclature

1.19

Suffixes in substitutive nomenclature

1.19

Sulfone polymers: description of

10.21

properties of

10.54

Sulfur: bond lengths

3.18

bond strengths

3.28

Sulfur compounds: infrared absorption frequencies of

6.41

nomenclature of

1.41

Raman frequencies of

6.67

Sulfur dioxide, solubility in water at various temperatures

4.5

Surface tension: of inorganic compounds

4.94

of organic compounds

4.57

Syndiotactic arrangement

10.3

Synthetic rubbers

10.2

chemical resistance

10.66

formulas and advantages of

10.60

gas permeability constants

10.70

properties of

10.64

This page has been reformatted by Knovel to provide easier navigation.

10.52

I.40

Index terms Systeme International d’ Unites (SI system):

Links 11.2

abbreviations

11.2

base units

11.2

conversion factors for

11.7

derived units

11.2

supplementary units

11.2

T t-values in statistics Tacticity

11.14 10.3

Taft equation: discussion of

7.2

pKA values for

7.10

reaction parameters for

7.10

Taft sigma constants

7.2

Taft substituent constants

7.2

Temperature: autoignition, of fuel-air mixtures control by various salts and solvents critical estimation of

4.99 9.2 5.75 5.88

effect on acidic dissociation constants

8.64

effect on pH reference buffer values

8.68

effect on reference electrode potentials

8.77

melting, of plastics

10.24

service: of plastics

10.24

of rubbers Tensile modulus of plastics

10.64 10.24

Tensile strength: of plastics

10.24

of rubbers

10.64

This page has been reformatted by Knovel to provide easier navigation.

8.79

I.41

Index terms

Links

Tension, aqueous (see Vapor pressure) Ternary azeotropic mixtures Thermal conductivity of plastics Thermal neutron absorption cross section of nuclides Thermal properties of plastics Thermodynamic properties of organic materials

4.46 10.24 3.2 10.24 5.2

Thermoplastic elastomers: description of

10.22

properties of

10.50

Thermoplastic polyester properties of Thermosetting polymers properties of

10.42 10.2 10.44

Thiophene azeotropes

4.45

Tin bond strengths

3.28

Torsional asymmetry

1.56

Transformations (conversion factors)

11.7

Triple bonds: infrared absorption frequencies of

6.28

Raman frequencies of

6.59

U Ultraviolet cutoffs: of chromatographic solvents

9.6

of spectrograde solvents

6.6

Ultraviolet stabilizers for polymers

10.7

Ultraviolet-visible, absorption bands

6.3

Ultraviolet-visible spectroscopy

6.3

Urea formaldehyde resin

10.23

properties of

10.56

Urethane rubber

10.63

properties of

10.64

This page has been reformatted by Knovel to provide easier navigation.

10.56

I.42

Index terms

Links

V Vapor pressure of water at various temperatures Vapor pressures Vaporization, enthalpy of

4.10 4.8 5.44

of mercury

4.8

of salt solutions

9.3

of water

4.10

Vinyl butyral polymers: description of

10.23

properties of

10.58

Vinyl chloride polymers: description of

10.22

properties of

10.56

10.58

Vinyl chloride-vinyl acetate copolymers: description of

10.22

properties of

10.56

Vinyl fluoride polymer

10.14

Vinyl polymers: description of

10.22

properties of

10.56

Vinylidene chloride polymers: description of

10.23

properties of

10.58

Vinylidene fluoride polymers: description of

10.13

properties of

10.34

Viscosity of chromatographic solvents

4.55 9.6

of inorganic compounds

4.94

of organic compounds

4.57

Vitamins, nomenclature of

1.43

This page has been reformatted by Knovel to provide easier navigation.

10.58

I.43

Index terms

Links

Voltammetric half-wave potentials

8.82

Volume, molar, critical

5.75

estimation of Vulcanization of polymers

5.88 10.7

W Water: absorption by plastics dielectric constant at various temperatures

10.24 4.98

permeability of polymers and rubbers to

10.70

refractive index at various temperatures

4.98

surface tension at various temperatures

4.98

vapor pressure at various temperatures

4.10

viscosity at various temperatures

4.98

Wavelength maxima of acid-base indicators Waxes, constants of Woodward–Fieser rules Work function and electronegativity

8.72 10.77 6.7 3.11

X Xenon: bond strengths solubility in water at various temperatures X-ray diffraction

3.28 4.7 6.112

Z Z(cis)-configuration

1.53

Zinc bond strengths

3.29

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