Dean's handbook of organic chemistry

Front Matter......Page 1
Preface......Page 3
About the Author......Page 4
Table of Contents......Page 0
Table of Contents......Page 5
1. Organic Compounds......Page 17
Table 1.1 Names of Straight-Chain Alkanes......Page 18
Table 1.2 Fused Polycyclic Hydrocarbons......Page 24
Table 1.4 Suffixes for Specialist Nomenclature of Heterocyclic Systems......Page 28
Table 1.5 Trivial Names of Heterocyclic Systems Suitable for Use in Fusion Names......Page 29
Table 1.6 Trivial Names for Heterocyclic Systems That Are Not Recommended for Use in Fusion Names......Page 32
Functionalized Compounds......Page 34
Table 1.7 Characteristic Groups for Substitutive Nomenclature......Page 35
Table 1.8 Characteristic Groups Cited Only as Prefixes in Substitutive Nomenclature......Page 37
Table 1.9 Functional Class Names Used in Radicofunctional Nomenclature......Page 40
Specific Functionalized Groups......Page 41
Table 1.10 Retained Trivial Names of Alcohols and Phenols with Structures......Page 42
Table 1.11 Names of Some Carboxylic Acids......Page 49
Table 1.12 Parent Structures of Phosphorus-Containing Compounds......Page 56
Table 1.13......Page 60
Stereochemistry......Page 63
Chemical Abstracts Indexing System......Page 76
Table 1.14 Empirical Formula Index for Organic Compounds......Page 77
Table 1.15 Physical Constants of Organic Compounds......Page 97
2. Inorganic and Organometallic Compounds......Page 412
Table 2.1 Physical Constants of Inorganic Compounds......Page 413
3. Properties of Atoms, Radicals, and Bonds......Page 445
Table 3.1 Table of Nuclides......Page 446
Electronegativity......Page 453
Table 3.2B Electronegativities of the Groups......Page 454
Table 3.3 Electron Affinities of Elements, Radicals, and Molecules......Page 455
Bond Lengths and Strengths......Page 457
Table 3.4A Bond Lengths between Carbon and Other Elements......Page 458
Table 3.4B Bond Lengths between Elements Other Than Carbon......Page 461
Table 3.5 Bond Strengths......Page 463
Table 3.6 Bond Dipole Moments......Page 474
Table 3.7 Group Dipole Moments......Page 475
4. Physical Properties......Page 477
Table 4.1 Solubility of Gases in Water......Page 478
Table 4.2 Vapor Pressure of Mercury......Page 484
Table 4.3 Vapor Pressure of Water for Temperatures from -10 to 120°C......Page 486
Table 4.5A Boiling Points for Common Organic Solvents......Page 488
Table 4.5B Boiling Points for Common Organic Solvents......Page 491
Table 4.5C Boiling Point for Common Organic Solvents......Page 493
Table 4.6 Molecular Elevation of the Boiling Point......Page 499
Table 4.7 Binary Azeotropic (Constant-Boiling) Mixtures......Page 501
Table 4.8 Ternary Azeotropic Mixtures......Page 522
Tables 4.9A and B Molecular Lowering of the Melting or Freezing Point......Page 528
Viscosity, Dielectric Constant, Dipole Moment, Surface Tension, and Refractive Index......Page 531
Table 4.10 Viscosity, Dielectric Constant, Dipole Moment and Surface Tension of Selected Organic Substances......Page 533
Table 4.11 Viscosity, Dielectric Constant, Dipole Moment, and Surface Tension of Selected Inorganic Substances......Page 570
Table 4.12 Refractive Index, Viscosity, Dielectric Constant, and Surface Tension of Water at Various Temperatures......Page 574
Table 4.13 Properties of Combustible Mixtures in Air......Page 575
5. Thermodynamic Properties......Page 579
Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities......Page 580
Table 5.1 Enthalpies and Gibbs (Free) Energies of Formation, Entropies, and Heat Capacities of Organic Compounds......Page 581
Table 5.2 Heats of Melting and Vaporization (or Sublimation) and Specific Heat at Various Temperatures of Organic Compounds......Page 622
Table 5.3 Critical Properties......Page 653
Table 5.4 Group Contributions for the Estimation of Critical Properties......Page 666
6. Spectroscopy......Page 668
Ultraviolet-Visible Spectroscopy......Page 670
Table 6.1 Electronic Absorption Bands for Representative Chromophores......Page 672
Table 6.2 Ultraviolet Cutoffs of Spectrograde Solvents......Page 673
Table 6.4 Absorption Wavelength of Enones and Dienones......Page 674
Table 6.5 Solvent Correction for UV-VIS Spectroscopy......Page 675
Table 6.7 Wavelength Calculation of the Principal Band of Substituted Benzene Derivatives......Page 676
Photoluminescence......Page 677
Table 6.8 Fluorescence Spectroscopy Data of Some Organic Compounds......Page 678
Table 6.10 Phosphorescence Spectroscopy of Some Organic Compounds......Page 684
Table 6.11 Absorption Frequencies of Single Bonds to Hydrogen......Page 688
Table 6.12 Absorption Frequencies of Triple Bonds......Page 695
Table 6.13 Absorption Frequencies of Cumulated Double Bonds......Page 696
Table 6.14 Absorption Frequencies of Carbonyl Bonds......Page 698
Table 6.15 Absorption Frequencies of Other Double Bonds......Page 702
Table 6.16 Absorption Frequencies of Aromatic Bonds......Page 706
Table 6.17 Absorption Frequencies of Miscellaneous Bands......Page 707
Table 6.18 Absorption Frequencies in the Near Infrared......Page 714
Table 6.19 Infrared Transmitting Materials......Page 716
Table 6.20 Infrared Transmission Characteristics of Selected Solvents......Page 718
Table 6.21 Raman Frequencies of Single Bonds to Hydrogen and Carbon......Page 721
Table 6.22 Raman Frequencies of Triple Bonds......Page 726
Table 6.23 Raman Frequencies of Cumulated Double Bonds......Page 727
Table 6.24 Raman Frequencies of Carbonyl Bonds......Page 728
Table 6.25 Raman Frequencies of Other Double Bonds......Page 730
Table 6.26 Raman Frequencies of Aromatic Compounds......Page 733
Table 6.27 Raman Frequencies of Sulfur Compounds......Page 734
Table 6.28 Raman Frequencies of Ethers......Page 736
Table 6.29 Raman Frequencies of Halogen Compounds......Page 737
Nuclear Magnetic Resonance Spectroscopy......Page 738
Table 6.31 Nuclear Properties of the Elements......Page 740
Table 6.32 Proton Chemical Shifts of Reference Compounds Relative to Tetramethylsilane......Page 741
Table 6.33 Common NMR Solvents......Page 742
Table 6.34 Proton Chemical Shifts......Page 743
Table 6.35 Estimation of Chemical Shift for Proton of -CH2- and >CH- Groups......Page 746
Table 6.36 Estimation of Chemical Shift of Proton Attached to a Double Bond......Page 747
Table 6.37 Chemical Shifts in Monosubstituted Benzene......Page 748
Table 6.38 Proton Spin Coupling Constants......Page 749
Table 6.39 Carbon-13 Chemical Shifts......Page 750
Table 6.40 Estimation of Chemical Shifts of Alkane Carbons......Page 753
Table 6.41 Effect of Substituent Groups on Alkyl Chemical Shifts......Page 754
Table 6.42 Estimation of Chemical Shift of Carbon Attached to a Double Bond......Page 755
Table 6.43 Carbon-13 Chemical Shifts in Substituted Benzenes......Page 756
Table 6.44 Carbon-13 Chemical Shifts in Substituted Pyridines......Page 757
Table 6.45 Carbon-13 Chemical Shifts of Carbonyl Group......Page 758
Table 6.46 One-Bond Carbon-Hydrogen Spin Coupling Constants......Page 759
Table 6.48 Carbon-Carbon Spin Coupling Constants......Page 760
Table 6.49 Carbon-Fluorine Spin Coupling Constants......Page 761
Table 6.50 Carbon-13 Chemical Shifts of Deuterated Solvents......Page 762
Table 6.52 Boron-11 Chemical Shifts......Page 763
Table 6.53 Nitrogen-15 (or Nitrogen-14) Chemical Shifts......Page 764
Table 6.54 Nitrogen-15 Chemical Shifts in Monosubstituted Pyridine......Page 767
Table 6.56 Nitrogen-15 to Hydrogen-1 Spin Coupling Constants......Page 768
Table 6.59 Fluorine-19 Chemical Shifts......Page 769
Table 6.62 Silicon-29 Chemical Shifts......Page 771
Table 6.63 Phosphorus-31 Chemical Shifts......Page 772
Table 6.64 Phosphorus-31 Spin Coupling Constants......Page 776
Electron Spin Resonance......Page 777
Table 6.65 Spin-Spin Coupling (Hyperfine Splitting Constants)......Page 778
Table 6.66A Ionization Potentials of Molecular Species......Page 781
Table 6.66B Alphabetical Listing of Ionization Potentials of Molecular Species......Page 787
X-Ray Diffraction......Page 789
7. Physiochemical Relationships......Page 792
Linear Free Energy Relationships......Page 793
Table 7.1 Hammett and Taft Substituent Constants......Page 794
Table 7.2 pKA and Rho (p) Values for the Hammett Equation......Page 799
Table 7.4 Special Hammett Sigma Constants......Page 801
8. Electrolytes, Electromotive Force, and Chemical Equilibrium......Page 803
Equilibrium Constants......Page 804
Table 8.1 pKA Values of Organic Materials in Water at 25°C......Page 805
Table 8.2 Proton-Transfer Reactions of Inorganic Materials in Water at 25°C......Page 863
Table 8.3 Selected Equilibrium Constants in Aqueous Solution at Various Temperatures......Page 866
Table 8.4 Indicators for Aqueous Acid-Base Titrations......Page 874
Table 8.5 National Institute of Standards and Technology (Formerly National Bureau of (Standards U.S.)) Reference pH Buffer Solutions......Page 876
Table 8.6 Compositions of National Institute of Standards and Technology. Standard pH Buffer Solutions......Page 877
Table 8.7 pH Values of Buffer Solutions for Control Purposes......Page 878
Table 8.8 Potentials of Reference Electrodes (in Volts) as a Function of Temperature......Page 879
Table 8.9 Potentials of Reference Electrodes (in Volts) at 25°C for Water-Organic Solvent Mixtures......Page 881
Table 8.10 Potentials of Selected Half-Reactions at 25°C......Page 882
Table 8.11 Half-Wave Potentials (vs. Saturated Calomel Electrode) of Organic Compounds at 25°C......Page 884
9. Data Useful in Laboratory Manipulations and Analysis......Page 896
Humidification and Drying......Page 897
Table 9.4 Humidity (%) Maintained by Saturated Solutions of Common Salts at Specified Temperatures......Page 898
Table 9.5 Drying Agents......Page 899
Table 9.6 Solvents of Chromatographic Interest......Page 900
Table 9.7 Solvents Having the Same Refractive Index and the Same Density at 25°C......Page 902
Table 9.8 McReynolds\' Constants for Stationary Phases in Gas Chromatography......Page 905
10. Polymers, Rubbers, Fats, Oils, and Waxes......Page 909
Polymers......Page 910
Table 10.1 Plastic Families......Page 915
Formulas and Key Properties of Plastic Materials......Page 917
Table 10.2 Properties of Commercial Plastics......Page 932
Formulas and Advantages of Rubbers......Page 968
Table 10.3 Properties of Natural and Synthetic Rubbers......Page 972
Table 10.4 Resistance of Selected Polymers and Rubbers to Various Chemicals at 20°C......Page 973
Table 10.5 Common Abbreviations Used in Polymer Chemistry......Page 975
Table 10.6 Gas Permeability Constants (1010P) at 25°C for Polymers and Rubbers......Page 978
Table 10.8 Constants of Fats and Oils......Page 981
Table 10.9 Constants of Waxes......Page 984
11. Abbreviations, Constants, and Conversion Factors......Page 986
Table 11.1 Fundamental Physical Constants......Page 987
Table 11.4 Numerical Prefixes......Page 990
Table 11.5 Conversion Formulas for Solutions Having Concentrations Expressed in Various Ways......Page 991
Table 11.6 Conversion Factors......Page 992
Table 11.7 Values of t......Page 999
A......Page 1001
B......Page 1005
C......Page 1008
D......Page 1013
E......Page 1014
F......Page 1017
H......Page 1019
I......Page 1022
K......Page 1024
M......Page 1025
N......Page 1027
P......Page 1029
R......Page 1034
S......Page 1036
T......Page 1040
U......Page 1041
V......Page 1042
Z......Page 1043