Akiba K. Organo main group chemistry (Hoboken, 2011). - ОГЛАВЛЕНИЕ / CONTENTS
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ОбложкаAkiba K. Organo main group chemistry. - Hoboken: Wiley, 2011. - xi, 275 p.: ill. - Bibliogr. at the end of the chapters. - Ind.: p.269-275. - ISBN 978-0-470-45033-8
 

Оглавление / Contents
 
Preface ........................................................ ix

1  Main Group Elements and Heteroatoms: Scope and
   Characteristics .............................................. 1
   1.1  Aufbau Principle and Sign of Orbitals ................... 1
   1.2  Electronic Configuration of an Atom: Main Group
        Elements and Heteroatoms ................................ 3
   1.3  Fundamental Properties of Main Group Elements ........... 5
   1.4  Acidity of Carboxylic Acid and Substituent Effect ....... 7
   1.5  Heteroatom Effect ...................................... 10
        1.5.1  Stabilization of α-Carbocation by Resonance:
               Stereoelectronic Effect ......................... 10
        1.5.2  Coordination with Lewis Acids ................... 15
   References .................................................. 16

Notes 1: Electronegativity ..................................... 17
   
Notes 2: Importance of Formal Logic-I: Oxidation Number and
         Formal Charge ......................................... 19
   
Notes 3: Importance of Formal Logic-II: Octet Rule, Eighteen-
         Electron Rule, Hypervalence ........................... 23

2  Main Group Element Effect ................................... 25
   2.1  What Is Main Group Element Effect? ..................... 25
   2.2  Single Bond Energy and π-Bond Energy ................... 27
   2.3  Hypervalent Compound ................................... 31
   2.4  Effect of Hypervalent Bond (1): 3c-4e Bond and
        Structure .............................................. 33
   2.5  Effect of Hypervalent Bond (2): Apicophilicity and
        Pseudorotation ......................................... 41
   2.6  Effect of Hypervalent Bond (3): Ligand Coupling
        Reaction (LCR) and Edge Inversion ...................... 45
   2.7  Effect of σX-C ........................................ 46
   2.8  Effect of σ*X-C ......................................... 48
   
Notes 4: (σ, σ*) and (π, π*): HMO (Hueckel Molecular Orbital)
         and Electrocyclic Reaction ............................ 57
   
3  Lithium, Magnesium, and Copper Compounds .................... 63
   3.1  Synthesis .............................................. 64
   3.2  Structure .............................................. 66
   3.3  Reaction ............................................... 68
        3.3.1  Deprotonation as Base ........................... 69
        3.3.2  Nucleophilic Reaction ........................... 72
        3.3.3  Conjugate Addition of Lithium Dimethylcuprate ... 76
   References .................................................. 77
4  Boron and Aluminum Compounds ................................ 79
   4.1  Synthesis .............................................. 80
   4.2  Structure .............................................. 82
   4.3  Reaction ............................................... 84
   References .................................................. 88
5  Silicon, Tin, and Lead Compounds ............................ 91
   5.1  Synthesis .............................................. 92
   5.2  Reaction ............................................... 94
   5.3  Organotin and Lead Compounds .......................... 100
   References ................................................. 104
   
Notes 5: Stable Carbene and Its Complex ....................... 105
   
6  Phosphorus, Antimony, and Bismuth Compounds ................ 111
   6.1  Phosphorus Compounds .................................. 112
   6.2  Synthesis of Organophosphorus Compounds ............... 113
   6.3  Tertiary Phosphine and Its Nucleophilic Reaction ...... 115
   6.4  Arbuzov Reaction ...................................... 117
   6.5  Perkow Reaction ....................................... 118
   6.6  Synthesis of Optically Active Phosphines .............. 119
   6.7  Ylide and Wittig Reaction and Related Ones ............ 123
   6.8  Reactions of Phosphonium Salts and Formation of
        Phosphoranes .......................................... 131
   6.9  Freezing BPR and Its Effect ........................... 138
   6.10 Antimony and Bismuth Compounds ........................ 143
   References ................................................. 146
   
Notes 6: Dreams of Staudinger and Wittig ...................... 149
   
Notes 7: Stereochemistry in Nucleophilic Substitution of 
         MX4-type Compounds: Inversion or Retention ........... 155
   
7  Sulfur, Selenium, and Tellurium Compounds .................. 159
   7.1  Sulfur Compounds ...................................... 160
   7.2  Synthesis of Organosulfur Compounds ................... 160
   7.3  Reactions of Organosulfur Compounds ................... 166
   7.4  Structure and Reaction of Hypervalent Organosulfur
        Compounds ............................................. 170
   7.5  Selenium and Tellurium Compounds ...................... 175
   References ................................................. 178

Notes 8: Inversion Mechanism of NH3 and NF3: Vertex 
         Inversion or Edge Inversion .......................... 181

8  Organohalogen Compounds: Fluorine and Iodine Compounds ..... 187
   8.1  Synthesis of Chlorine and Bromine Compounds ........... 188
   8.2  Fluorine Compounds .................................... 190
   8.3  Iodine Compounds ...................................... 195
   References ................................................. 199

9  Atrane and Transannular Interaction: Formation of
   Hypervalent Bond ........................................... 201
   9.1  Introduction .......................................... 201
   9.2  Silatrane and Atrane .................................. 202
   9.3  Transannular Interaction (1) .......................... 208
   9.4  Transannular Interaction (2) .......................... 210
   References ................................................. 211

10 Unsaturated Compounds of Main Group Elements of Third
   Period and Heavier ......................................... 213
   10.1 Introduction .......................................... 213
   10.2 Unsaturated Bonds of Group 15 Elements of Third
        Period and Heavier .................................... 215
   10.3 Unsaturated Bonds of Group 14 Elements of Third
        Period and Heavier .................................... 219
   10.4 Aromatic Compounds of Group 14 Elements ............... 222
   References ................................................. 223

11 Ligand Coupling Reaction ................................... 225
   11.1 Introduction .......................................... 225
   11.2 Selectivity of Ligand Coupling Reaction: Theoretical
        Investigation ......................................... 226
   11.3 Ligand Coupling Reaction of Organic Compounds of 
        Phosphorus, Antimony, and Bismuth ..................... 227
   11.4 Ligand Coupling Reaction of Organic Compounds of 
        Sulfur, Selenium, and Tellurium ....................... 237
   11.5 Ligand Coupling Reaction of Organoiodine Compounds .... 241
   References ................................................. 245

Notes 9: Hexavalent Organotellurium Compounds ................. 247
   
12 Hypervalent Carbon Compounds: Can Hexavalent Carbon
   Exist? ..................................................... 251
   12.1 Introduction .......................................... 251
   12.2 Attempts for Pentacoordinate Hypervalent Carbon 
        Species ............................................... 253
   12.3 Synthesis of Pentacoordinate Hypervalent Carbon
        Species (10-C-5) and Bond Switching at Carbon and
        Boron ................................................. 254
   12.4 Attempts to Hexacoordinate Hypervalent Carbon 
        Species (12-C-6) ...................................... 259
   References ................................................. 262

Notes 10: Main Group Element Porphyrins ....................... 265

Index ......................................................... 269


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