Ⅰ．THE DEVELOPMENT OF STRUCTURAL CHEMISTRY 1
1．Valence 1
2．Structural Isomerism 6
3．The Persistence of Structure 6
4．Structural Analogy 10
5．Structural Iteration 12
6．Tautomerism 14
7．Stereoisomerism 16
8．The Constancy of Valence 20
Ⅱ．ATOMIC STRUCTURE 26
9．The Nuclear Atom 26
10．The Lewis Atom 27
11．The Quantum Theory of the Atom 28
11a．The Bohr atom 28
11b．The wave mechanical atom 29
Ⅲ．MOLECULAR STRUCTURE 38
12．Electronic Structural Formulas 38
12a．Co-ordination number 42
12b．Charge distribution 43
12c．Acids,bases,and free radicals 45
13．The Electron Pair Bond in Quantum Mechanics 46
13a．Methods of approximation 47
13b．The hydrogen molecule 51
13c．The one-electron bond 58
13d．Bond dipole 59
13e．The tetrahedral carbon atom 60
Ⅳ．GROUP INTERACTION 62
14．Group Interactions without Considering Resonance 62
14a．Steric hindrance 62
14b．Negativity 63
14c．Polarity and induction 63
14d．The Hixon-Johns method 65
15．Conjugation 67
Ⅳ．GROUP INTERACTION(Cont．) 70
16．Resonance and Mesomerism 70
16a．Mesomerism as a tautomerism 70
16b．Molecular resonance as an extension of the Lewis theory 73
16c．Molecular resonance as a theorem in quantum mechanics 81
Ⅴ．PHYSICAL PROPERTIES 91
17．Bond Distances and Angles 92
17a．Experimental methods 92
17b．Bond distances 111
17c．The hydrogen bond 116
17d．Bond angles 121
17e．Free rotation 124
18．Dipole Moments 126
18a．Bond moments 129
18b．Sign of dipole moment 132
18c．Vector addition of dipole moments 133
18d．Dipole moment and rotation about a single bond 139
18e．Dipole moment and resonance 144
19．Raman Spectra and Force Constants 151
19a．Force constants 153
20．Color 155
20a．Older theories 157
20b．Quantum mechanical calculations 157
20c．Complexity of spectra 159
20d．Electrons as quantized oscillators 162
20e．Approximately linear oscillators 163
20f．Conjugation,insulation,partials 168
20g．The function of auxochromes 172
20h．Oscillators in more than one direction 174
20i．Acid-base indicators 179
Ⅵ．EQUILIBRIUM—ACID STRENGTH 183
21．Equilibrium 183
22．Acids and Bases 186
23．Acid Strength and Structure 188
23a．Mechanism of comparison of acid strength 188
23b．Mechanism for the description of intramolecular action;division into contributing factors 192
24．Acids without Resonance 201
24a．Discussion of special cases 205
24b．The electrostatic method 216
25．The Fatty Acids 217
26．Unsaturated Acids 233
26s．Cross-conjugation 235
27．The Aromatic Acids 240
27a．Resonance of aromatic nuclei 240
27b．Classification of aromatic acids 242
27c．Meta groups 245
27d．Para groups 249
27e．Ortho groups 257
28．Miscellaneous Acids 265
28a．Ammonia acids 266
28b．Methane acids 268
28c．Generalized acids 269
Ⅶ．ENERGY RELATIONSHIPS IN SOME OTHER REACTIONS 271
29．Ionic Resonance and the Heat of Formation 271
30．Valence Bond Resonance and Heat of Formation 272
30a．The branched-chain effect 274
30b．Ring strain 278
30c．Resonance energies 280
31．Tautomerism 281
31a．Keto-enol equilibria 289
31b．Solvent effect 296
31c．Other tautomeric systems 297
32．Oxidation-Reduction Potentials 303
32a．Homopolar valence bond resonance 305
32b．Ionic resonance and induction 315
33．Free Radicals 317
33a．Trivalent carbon 319
33b．Divalent nitrogen and tetravalent nitrogen 326
33c．Monovalent oxygen 332
33d．Diradicals 333
34．cis-trans Isomerism of Olefins 339
35．Equilibrium in the Addition to the Double Bond 343
Ⅷ．THE RATE FACTOR IN CHEMICAL BEHAVIOR 352
36．The Variation of Rate with Concentration 353
36a．Reversible reactions 354
36b．Simultaneous reaction 356
36c．Successive reactions 357
36d．Catalysis 362
36e．Chain reactions 364
36f．Inhibitors 365
37．The Temperature Coefficient of Reaction Rate 367
37a．Unimolecular reactions 369
37b．Bimolecular reactions 372
37c．The temperature coefficient of a complex reaction 375
38．Transition state 376
39．Molecular association 384
40．The Quantum Mechanical Treatment 387
40a．The Eyring-Polanyi method 390
Ⅸ．THE REACTIONS OF ACIDS AND BASES WITH NEUTRAL SUB-STANCES—THREE-CENTER REACTIONS 393
41．The Mechanisms of the Reactions 394
41a．The Walden inversion 395
41b．The differentiation of rate-determining and preliminary reversible reactions 396
41c．The salt effect 397
41d．Reaction with both hydrogen ion and undissociated acid 399
41e．Reaction of substrate with either acid or base 401
41f．Lowry＇s mechanism 403
41g．Unimolecular and bimolecular hydrolysis 405
41h．Slow and fast reactions 407
42．The Strength of the Reacting Acid or Base(C) 408
42a．Br？nsted＇s equation 409
42b．Hammett＇s equation 416
42c．The relationship between Br？nsted＇s and Hammett＇s equations 420
42d．Acids without hydrogen atoms 420
42e．Charged and neutral bases 421
42f．The polarizability effect 422
43．The Strength of the Product Acid or Base(A) 423
44．The Middle Group(B)in the Three-Center Reaction 426
45．Inductive and Tautomeric Effects 428
46．The Effect of Branching Chains 430
47．The Effect of Resonance on Reaction Rate 434
47a．Effect of resonance in a reacting or product base 435
47b．Resonance of the middle group of the transition state 436
47c．Resonance effects of para substituents 440
48．Steric Effects 443
Ⅹ．REACTIONS OF THE DOUBLE BOND 449
49．The Ethylenic Double Bond 451
49a．Ethylenes as bases or pseudo-bases 451
49b．Stereochemistry of addition reactions 454
49c．Macropolymerization 455
50．The Carbonyl Double Bond 457
50a．Addition of bisulfite ion 458
50b．Oximes,hydrazones,and semicarbazones 459
50c．Addition of organometallic compounds 462
50d．The aldol condensation 463
50e．The Cannizzaro reaction 466
51．Conjugate Systems 467
52．Substitution Reactions of Benzene 470
52a．The directing influence of substituents 471
52b．Application of Hammett＇s equation to para and meta substitution 480
52c．The reaction of benzene as a pseudo-acid 481
52d．The reaction of carbonyl compounds with phenols and anilines 482
52e．The relationship between addition to ethylene and substitution in benzene 483
52f．Condensed-ring systems 484
53．Four-Center Reactions 487
53a．Aromatic rings in the diene condensation 490
AUTHOR INDEX 493
SUBJECT INDEX 499