Molecular orbitals and organic chemical reactions:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Chichester [u.a.]
Wiley
2009
|
| Ausgabe: | Student ed., 1. publ. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XV, 360 S. Ill., graph. Darst. |
| ISBN: | 9780470746608 9780470746592 |
Internformat
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Datensatz im Suchindex
| _version_ | 1804140859216625664 |
|---|---|
| adam_text | Titel: Molecular orbitals and organic chemical reactions
Autor: Fleming, Ian
Jahr: 2009
Contents
Preface xi
1 Molecular Orbital Theory 1
1.1 The Atomic Orbitals of a Hydrogen Atom 1
1.2 Molecules made from Hydrogen Atoms 2
1.2.1 The H2 Molecule 2
1.2.2 The H3 Molecule 7
1.2.3 The H4 Molecule 8
1.3 C Hand C-C Bonds 9
1.3.1 The Atomic Orbitals of a Carbon Atom 9
1.3.2 Methane 12
1.3.3 Methylene 13
1.3.4 Hybridisation 15
1.3.5 C C a Bonds and it Bonds: Ethane 18
1.3.6 C=C 7T Bonds: Ethylene 20
1.4 Conjugation—Hiickel Theory 22
1.4.1 The Allyl System 22
1.4.2 Butadiene 28
1.4.3 Longer Conjugated Systems 31
1.5 Aromaticity 32
1.5.1 Aromatic Systems 32
1.5.2 Antiaromatic Systems 34
1.5.3 The Cyclopentadienyl Anion and Cation 37
1.5.4 Homoaromaticity 37
1.5.5 Spiro Conjugation 38
1.6 Strained a Bonds—Cyclopropanes and Cyclobutanes 39
1.6.1 Cyclopropanes 39
1.6.2 Cyclobutanes 42
1.7 Heteronuclear Bonds, C-M, C-X and C=O 42
1.7.1 Atomic orbital energies and electronegativity 43
1.7.2 CXct Bonds 43
1.7.3 C-M a Bonds 47
1.7.4 C=Ott Bonds 49
1.7.5 Heterocyclic Aromatic Systems 51
1.8 The Tau Bond Model 52
vi CONTENTS
1.9 Spectroscopic Methods 53
1.9.1 Ultraviolet Spectroscopy 53
1.9.2 Photoelectron Spectroscopy 54
1.9.3 Nuclear Magnetic Resonance Spectroscopy 55
1.9.4 Electron Spin Resonance Spectroscopy 56
1.10 Exercises 57
2 The Structures of Organic Molecules 59
2.1 The Effects of 7T Conjugation 59
2.1.1 A Notation for Substituents 59
2.1.2 The Effect of Substituents on the Stability of
Alkenes 60
2.1.3 The Effect of Substituents on the Stability of
Carbocations 65
2.1.4 The Effect of Substituents on the Stability of
Carbanions 66
2.1.5 The Effect of Substituents on the Stability of
Radicals 67
2.1.6 Energy-Raising Conjugation 69
2.2 a Conjugation—Hyperconjugation 69
2.2.1 C—H and C—C Hyperconjugation 70
2.2.2 C—M Hyperconjugation 74
2.2.3 Negative Hyperconjugation 76
2.3 The Configurations and Conformations of Molecules 81
2.3.1 Restricted Rotation in 7r-Conjugated Systems 82
2.3.2 Preferred Conformations from Conjugation in
the 7 Framework 89
2.4 Other Noncovalent Interactions 90
2.4.1 The Hydrogen Bond 90
2.4.2 Hypervalency 92
2.4.3 Polar Interactions, and van der Waals and other
Weak Interactions 93
2.5 Exercises 95
3 Chemical Reactions—How Far and How Fast 97
3.1 Factors Affecting the Position of an Equilibrium 97
3.2 The Principle of Hard and Soft Acids and Bases
(HSAB) 97
3.3 Transition Structures 103
3.4 The Perturbation Theory of Reactivity 104
3.5 The Salem-Klopman Equation 106
3.6 Hard and Soft Nucleophiles and Electrophiles 109
3.7 Other Factors Affecting Chemical Reactivity 110
CONTENTS vii
4 Ionic Reactions—Reactivity 111
4.1 Single Electron Transfer (SET) in Ionic Reactions 111
4.2 Nucleophilicity 114
4.2.1 Heteroatom Nucleophiles 114
4.2.2 Solvent Effects 118
4.2.3 Alkene Nucleophiles 118
4.2.4 Thea-Effect 119
4.3 Ambident Nucleophiles 121
4.3.1 Thiocyanate Ion, Cyanide Ion and Nitrite Ion
(and the Nitronium Cation) 121
4.3.2 Enolate Ions 124
4.3.3 Allyl Anions 125
4.3.4 Aromatic Electrophilic Substitution 129
4.4 Electrophilicity 134
4.4.1 Trigonal Electrophiles 134
4.4.2 Tetrahedral Electrophiles 136
4.4.3 Hard and Soft Electrophiles 137
4.5 Ambident Electrophiles 137
4.5.1 Aromatic Electrophiles 138
4.5.2 Aliphatic Electrophiles 140
4.6 Carbenes 147
4.6.1 Nucleophilic Carbenes 148
4.6.2 Electrophilic Carbenes 149
4.6.3 Aromatic Carbenes 149
4.7 Exercises 151
5 Ionic Reactions—Stereochemistry 153
5.1 The Stereochemistry of the Fundamental Organic
Reactions 154
5.1.1 Substitution at a Saturated Carbon 154
5.1.2 Elimination Reactions 156
5.1.3 Nucleophilic and Electrophilic Attack on a n Bond 158
5.1.4 The Stereochemistry of Substitution at Trigonal
Carbon 165
5.2 Diastereoselectivity 167
5.2.1 Nucleophilic Attack on a Double Bond with
Diastereotopic Faces 169
5.2.2 Nucleophilic and Electrophilic Attack on
Cycloalkenes 175
5.2.3 Electrophilic Attack on Open-Chain Double Bonds
with Diastereotopic Faces 178
5.2.4 Diastereoselective Nucleophilic and Electrophilic
Attack on Double Bonds Free of Steric Effects 182
5.3 Exercises 183
viij CONTENTS
6 Thermal Pericydic Reactions 185
6.1 The Four Classes of Pericyclic Reactions 186
6.2 Evidence for the Concertedness of Bond Making
and Breaking 188
6.3 Symmetry-Allowed and Symmetry-Forbidden Reactions 190
6.3.1 The Woodward-Hoffmann Rules—Class by Class 190
6.3.2 The Generalised Woodward-Hoffmann Rule 200
6.4 Explanations for the Woodward-Hoffmann Rules 214
6.4.1 The Aromatic Transition Structure 215
6.4.2 Frontier Orbitals 215
6.4.3 Correlation Diagrams 216
6.5 Secondary Effects 221
6.5.1 The Energies and Coefficients of the Frontier
Orbitals of Alkenes and Dienes 222
6.5.2 Diels-Alder Reactions 224
6.5.3 1,3-Dipolar Cycloadditions 242
6.5.4 Other Cycloadditions 252
6.5.5 Other Pericyclic Reactions 259
6.5.6 Periselectivity 263
6.5.7 Torquoselectivity 267
6.6 Exercises 270
7 Radical Reactions 275
7.1 Nucleophilic and Electrophilic Radicals 275
7.2 The Abstraction of Hydrogen and Halogen Atoms 277
7.2.1 The Effect of the Structure of the Radical 277
7.2.2 The Effect of the Structure of the Hydrogen or
Halogen Source 278
7.3 The Addition of Radicals to n Bonds 279
7.3.1 Attack on Substituted Alkenes 279
7.3.2 Attack on Substituted Aromatic Rings 282
7.4 Synthetic Applications of the Chemoselectivity of Radicals 286
7.5 Stereochemistry in some Radical Reactions 287
7.6 Ambident Radicals 290
7.6.1 Neutral Ambident Radicals 290
7.6.2 Charged Ambident Radicals 291
7.7 Radical Coupling 295
7.8 Exercises 296
8 Photochemical Reactions 299
8.1 Photochemical Reactions in General 299
8.2 Photochemical Ionic Reactions 301
8.2.1 Aromatic Nucleophilic Substitution 301
8.2.2 Aromatic Electrophilic Substitution 302
8.2.3 Aromatic Side-Chain Reactivity 303
CONTENTS ix
8.3 Photochemical Pericyclic Reactions and Related Stepwise
Reactions 304
8.3.1 The Photochemical Woodward-Hoffmann Rule 304
8.3.2 Regioselectivity of Photocycloadditions 307
8.3.3 Other Kinds of Selectivity in Pericyclic and Related
Photochemical Reactions 319
8.4 Photochemically Induced Radical Reactions 321
8.5 Chemiluminescence 323
8.6 Exercises 324
References 327
Index 331
|
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| discipline | Chemie / Pharmazie Chemie |
| edition | Student ed., 1. publ. |
| format | Book |
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| isbn | 9780470746608 9780470746592 |
| language | English |
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| spelling | Fleming, Ian 1935- Verfasser (DE-588)139245359 aut Molecular orbitals and organic chemical reactions Ian Fleming Student ed., 1. publ. Chichester [u.a.] Wiley 2009 XV, 360 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Molecular orbitals Textbooks Physical organic chemistry Textbooks Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf MO-Theorie (DE-588)4170580-4 gnd rswk-swf Chemische Reaktion (DE-588)4009853-9 gnd rswk-swf Molekülorbital (DE-588)4127526-3 gnd rswk-swf Reaktivität (DE-588)4208182-8 gnd rswk-swf MO-Theorie (DE-588)4170580-4 s Organische Verbindungen (DE-588)4043816-8 s DE-604 Molekülorbital (DE-588)4127526-3 s Chemische Reaktion (DE-588)4009853-9 s Reaktivität (DE-588)4208182-8 s 1\p DE-604 HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018737692&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Fleming, Ian 1935- Molecular orbitals and organic chemical reactions Molecular orbitals Textbooks Physical organic chemistry Textbooks Organische Verbindungen (DE-588)4043816-8 gnd MO-Theorie (DE-588)4170580-4 gnd Chemische Reaktion (DE-588)4009853-9 gnd Molekülorbital (DE-588)4127526-3 gnd Reaktivität (DE-588)4208182-8 gnd |
| subject_GND | (DE-588)4043816-8 (DE-588)4170580-4 (DE-588)4009853-9 (DE-588)4127526-3 (DE-588)4208182-8 |
| title | Molecular orbitals and organic chemical reactions |
| title_auth | Molecular orbitals and organic chemical reactions |
| title_exact_search | Molecular orbitals and organic chemical reactions |
| title_full | Molecular orbitals and organic chemical reactions Ian Fleming |
| title_fullStr | Molecular orbitals and organic chemical reactions Ian Fleming |
| title_full_unstemmed | Molecular orbitals and organic chemical reactions Ian Fleming |
| title_short | Molecular orbitals and organic chemical reactions |
| title_sort | molecular orbitals and organic chemical reactions |
| topic | Molecular orbitals Textbooks Physical organic chemistry Textbooks Organische Verbindungen (DE-588)4043816-8 gnd MO-Theorie (DE-588)4170580-4 gnd Chemische Reaktion (DE-588)4009853-9 gnd Molekülorbital (DE-588)4127526-3 gnd Reaktivität (DE-588)4208182-8 gnd |
| topic_facet | Molecular orbitals Textbooks Physical organic chemistry Textbooks Organische Verbindungen MO-Theorie Chemische Reaktion Molekülorbital Reaktivität |
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