国外化学名著系列 高等有机化学-结构与机理 （影印版 第五版，Carey, Francis A., Sundberg, Richard J.） fb2 pdf azw3 网盘 rtf 免费 下载 txt

自从1977年面世以来，《高等有机化学》作为学科教材的地位一直没有动摇过，广泛地覆盖了有机化合物的结构、反应活性及合成。她的第五版相对2001年出版的第四版进行了大幅度的修订，更新了学科发展的相关资料，内容组织更加清晰明朗，特别是计算化学部分。Part A从化合物结构和立体化学基础概念讲起，涉及有机化学反应热力学和动力学的方方面面。主要反应类型涵盖亲核取代反应、加成反应、碳负离子和羰基化学反应、芳环取代反应、周环反应、自由基反应和光化学反应。每章后附有习题精选及解答习题的推荐参考文献。

Contents

Preface v

Acknowledgment and Personal Statement vii

Introduction ix

Chapter 1 Chemical Bonding and Molecular Structure 1

Introduction ix

1.1 Description of Molecular Structure Using Valence Bond Concepts 2

1 1.1 Hybridization 4

1.1.2 The Origin of Electron-Electron Repulsion 7

1.1.3 Electronegativity and Polarity 8

1.1.4 Electronegativity Equahzat10n 11

1.1.5 Differential Electronegativity of Carbon Atoms 12

1.1.6 Polarizability， Hardness， and Softness 14

1.1.7 Resonance and Conjugation 18

1.1.8 Hyperconjugation 22

1.1.9 Covalent and van der Waals Radii of Atoms 24

1.2 Molecular Orbital Theory and Methods 26

I 2.1 The Huckel MO Method 27

1.2.2 Semiempirical MO Methods 32

1.2.3 Ab Initio Methods 32

1.2.4 Pictorial Representation of MOs for Molecules 35

1.2.5 Qualitative Application of MO Theory to Reactivity: Perturbational MO Theory and Frontier Orbitals 41

1.2.6 Numerical Application of MO Theory 50

1.3 Electron Density Functionals 54

1.4 Representation of Electron Density Distribution 57

1.4 1 Mululliken Populat10n Analysis 60

1.4.2 Natural Bond Orbitals and Natural Population Analysis 61

1.4.3 Atoms m Molecules 63

1.4.4 Comparison and Interpretation of Atomic Charge Calculations 70

1.4.5 Electrostatic Potential Surfaces 73

1.4.6 Relationships between Electron Density and Bond Order 76

Topic 1.1 The Origin of the Rotational (Torsional) Barrier in Ethane and Other Small Molecules 78

Topic 1.2 Heteroatom Hyperconjugation (Anomeric Effect) in Acyclic Molecules 81

Topic 1.3 Bonding in Cyclopropane and Other Small Ring Compounds 85

Topic 1.4 Representation of Electron Density by the Laplacian Function 92

Topic 1.5 Application of Density Functional Theory to Chemical Properties and Reactivity 94

T.1.5.1 DFT Formulation of Chemical Potential， Electronegativity， Hardness and Softness， and Covalent and van der Waal Radii 95

T.1.5.2 DFT Formulation of Reactivity-The Fukui Function 97

T.1.5.3 DFT Concepts of Substituent Groups Effects 100

General References 106

Problems 106

Chapter 2 Stereochemistry， Conformation， and Stereoselectivity 119

Introduction 119

2.1 Configuration 119

2.1.1 Configuration at Double Bonds 119

2.1.2 Configuration of Cyclic Compounds 121

2.1.3 Configuration at Tetrahedral Atoms 122

2.1.4 Molecules with Multiple Stereogenic Centers 126

2.1.5 Other Types of Stereogenic Centers 128

2.1.6 The Relationship between Chirality and Symmetry 131

2.1 7 Configuration at Prochiral Centers 133

2.1.8 Resolution—The Separation of Enantiomers 136

2.2 Conformation 142

2.2 l Conformation of Acyclic Compounds 142

2.2.2 Conformations of Cyclohexane Derivatives 152

2.2.3 Conformations of Carbocyclic Rings of Other Sizes 161

2.3 Molecular Mechanics 167

2.4 Stereoselective and Stereospecific Reactions 169

2.4.1 Examples of Stereoselective Reactions 170

2.4.2 Examples of Stereospecific Reactions 182

2.5 Enantioselective React10ns 189

2.5.1 Enantioselective Hydrogenation 189

2.5.2 Enantioselective Reduction of Ketones 193

2.5.3 Enantioselective Epoxidation of Allylic Alcohols 196

2.5.4 Enantioselective Dihydroxylation of Alkenes 200

2.6 Double Stereodifferentiation: Reinforcing and Competing Stereoselect1v1ty 204

Topic 2.1 Analysis and Separation of Enantiomeric Mixtures 208

T.2.1.1 Chiral Shift Reagents and Chiral Solvating Agents 208

T.2.1.2 Separation of Enantiomers 211

Topic 2.2 Enzymatic Resolution and Desymmetrization 215

T.2.2.1 Li pases and Esterases 216

T.2.2.2 Proteases and Acy lases 222

T.2.2.3 Epoxide Hydrolases 224

Topic 2.3 The Anomeric Effect in Cyclic Compounds 227

Topic 2.4 Polar Substituent Effects in Reduction of Carbonyl Compounds 234

General References 239

Problems 240

Chapter 3 Structural Effects on Stability and Reactivity 253

Introduction 253

3.1 Thermodynamic Stability 254

3.1.1 Relationship between Structure and Thermodynamic Stability for Hydrocarbons 256

3.1.2 Calculation of Enthalpy of Formation and Enthalpy of Reaction 257

3.2 Chemical Kinetics 270

3.2.1 Fundamental Principles of Chemical Kinetics 270

3.2.2 Representation of Potential Energy Changes m Reacllons 273

3.2.3 Reaction Rate Expressions 280

3.2.4 Examples of Rate Expressions 283

3.3 General Relationships between Thermodynamic Stability and Reaction Rates 285

3.3.1 Kinetic versus Thermodynamic Control of Product Composition 285

3.3.2 Correlations between Thermodynamic and Kinetic Aspects of Reactions 287

3.3.3 Curtm-Hammett Prmciple 296

3.4 Electronic Substituent Effects on Reaction Intermediates 297

3 4.1 Carbocations 300

3.4.2 Carbanions 307

3.4 3 Radical Intermediates 311

3.4.4 Carbonyl Addition Intermediates 319

3.5 Kinetic Isotope Effects 33

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书籍介绍

《高等有机化学:结构与机理(第5版)》自从1997年面世以来，《高等有机化学》作为学科首选教材的地位一直没有动摇过，广泛地覆盖了有机化合物的结构、反应活性及合成。她的第五版相对2001年出版的第四版进行了大幅度的修订，更新了学科发展的相关资料，内容组织更加清晰明朗，特别是计算化学部分。Part A从化合物结构和立体化学基础概念讲起，涉及有机化学反应热力学和动力学的方方面面。主要反应类型涵盖亲核取代反应、加成反应、碳负离子和羰基化学反应、芳环取代反应、周环反应、自由基反应和光化学反应。每章后附有习题精选及解答习题的推荐参考文献。