Product Details
- Pub. Date: June 2003
- Publisher: McGraw-Hill Companies, The
- Format: Hardcover, 800pp
- ISBN-13: 9780071375931
- ISBN: 0071375937
- Edition Number: 2
- Edition Description: REV
* Biopolymers
* Electronegativity
* Nomenclatures for supramolecular compounds
* Properties tables for atoms, radicals, and bonds
* Line-angle structural drawings
* And much, much more! No matter if you're a chemist, a chemical or environmental engineer, or even a student, Dean's Handbook of Organic Chemistry will add precision, insight, and a host of timesaving tips to your efforts. Complete Coverage of:
* Organic compounds
* Inorganic compounds
* Properties of atoms, radicals, and bonds
* Physical properties
* Thermodynamic properties
* Spectroscopy
* Physicochemical relationships
* Electrolytes, electromotive force, and chemical equilibrium
* Laboratory manipulations
* Polymers, rubbers, fats, oils, and waxes
Gokel (Washington Univ., St. Louis) has prepared a new edition (1st ed., 1987) of a useful handbook that students and researchers will find extremely valuable. It is a convenient reference work that provides tables for physical constants of organic and inorganic compounds as well as spectral data and thermodynamic properties; these sections make up the bulk of the manual. There are more than a thousand pages of tabled data, divided into 11 sections: organic compounds; inorganic and organometallic compounds; properties of atoms, radicals, and bonds; physical properties; thermodynamic properties; spectroscopy; physiochemical relationships; electrolytes, electromotive force, and chemical equilibrium; data useful in laboratory manipulations and analysis; polymers, rubbers, fats, oils, and waxes; abbreviations, constants, and conversion factors. Easy-to-use index. Summing Up: Recommended. Graduate students through professionals.
Contents
Preface ............................................................................. iv
About the Author .............................................................v
1. Organic Compounds ................................... 1.1
Nomenclature of Organic Compounds ..................... ... 1.2
Hydrocarbons and Heterocycles ................................... 1.2
Table 1.1 Names of Straight-Chain Alkanes ................ 1.2
Table 1.2 Fused Polycyclic Hydrocarbons .................... 1.8
Table 1.3 Specialist Nomenclature for
Heterocyclic Systems ..................................................... 1.12
Table 1.4 Suffixes for Specialist Nomenclature
of Heterocyclic Systems ................................................. 1.12
Table 1.5 Trivial Names of Heterocyclic
Systems Suitable for Use in Fusion
Names ................................................................................ 1.13
Table 1.6 Trivial Names for Heterocyclic
Systems That Are Not Recommended for
Use in Fusion Names ........................................................ 1.16
Functionalized Compounds .............................................. 1.18
Table 1.7 Characteristic Groups for Substitutive
Nomenclature ..................................................................... 1.19
Table 1.8 Characteristic Groups Cited Only as
Prefixes in Substitutive Nomenclature ............................ 1.21
Table 1.9 Functional Class Names Used in
Radicofunctional Nomenclature ......................................... 1.24
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Specific Functionalized Groups ........................................... 1.25
Table 1.10 Retained Trivial Names of Alcohols
and Phenols with Structures ................................................ 1.26
Table 1.11 Names of Some Carboxylic Acids ...................... 1.33
Table 1.12 Parent Structures of Phosphorus-
Containing Compounds ............................................................ 1.40
Table 1.13 .................................................................................. 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. Inorganic and Organometallic Compounds .......... 2.1
Table 2.1 Physical Constants of Inorganic
Compounds ....................................................................................... 2.2
3. 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
Contents v
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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 ........................................ 4.55
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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
Contents vii
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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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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
Contents ix
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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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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
Contents xi
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7. 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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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
Contents xiii
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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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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 ................................................................................ I.1
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