Organic conformational analysis and stereochemistry from circular dichroism spectroscopy:
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| Main Authors: | , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
New York [u.a.]
Wiley-VCH
2000
|
| Series: | Methods in stereochemical analysis
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XIII, 487 S. Ill., graph. Darst. - Ill., graph. Darst. |
| ISBN: | 0471354058 |
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Record in the Search Index
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| adam_text | Titel: Organic conformational analysis and stereochemistry from circular dichroism spectroscopy
Autor: Lightner, David A
Jahr: 2000
Contents
Preface xi
1. Introduction 1
References 4
2. Cyclohexane and Cyclohexanone 5
2.1. Cyclohexane 5
2.2. Cyclohexane and Dynamic NMR 13
2.3. Substituted Cyclohexanes and Dynamic NMR 16
2.4. Conformation from Molecular Mechanics 22
2.5. Cyclohexanone 24
2.6. Substituted Cyclohexanones 27
2.7. Substituted Cyclohexanones, Optical Activity, and Circular
Dichroism 31
References 33
3. Optical Activity 37
3.1. Absorption of Light and Its Relationship to Optical Activity 37
3.2. The Origin of Optical Activity 40
3.3. Angle of Rotation ( J , a) and Optical Rotary Dispersion (ORD) 45
3.4. Angle of Ellipticity (0) and Circular Dichroism (Ae) 47
3.5. Quantitative Relationship Between CD and ORD 50
3.6. The Magnitude of Optical Activity, Cotton Effects, and
Rotatory Strength 51
3.7. Optical Activity of Chromophores 52
3.8. Limiting Classification of Chromophores as Inherently
Symmetric or Inherently Dissymmetric 53
References 56
Appendix: Experimental Rotatory Strengths 56
4. The Octant Rule 63
4.1. Optical Activity of the Ketone n 7t* Electronic Transition 64
4.2. Formulation of the Octant Rule from Carbonyl n - 7t* Nodal Planes 65
4.3. How to Use the Octant Rule to Determine Absolute Stereochemistry
and Conformation 66
4.4. The Question of Front Octants 71
4.5. The Location and Shape of the Third Nodal Surface: Anti-Octant
Effects 74
4.6. Perturbers Lying in Octant Symmetry Planes: Qualitative Completeness
and the Octant Rule 79
vii
CONTENTS
vui
4.7. Octant Rule Theory and Analysis 81
4.8. The Octant Rule and Octant Surfaces 85
4.9. Mechanism of Optical Activity and CD from Octant Consignate and
Dissignate W-Coupling Paths 86
4.10. Ketone Carbonyl Short-Wavelength Transitions 87
References 92
5. Conformational Analysis of Substituted
Cyclohexanones 95
5.1. 2-MethyIcyclohexanone and 2-Methyl-4-/e,rr-butylcyclohexanone 95
5.2. Other Conformationally Immobilized a-Methylcyclohexanones 100
5.3. 2-Isopropy! and 2-/ ?rf-Butylcyclohexanone 105
5.4.3-Methylcyclohexanone 109
5.5. trans-2-Bromo- and 2-Chloro-5-methylcyclohexanone 111
5.6. Conformer Populations and AG from Variable-Temperature CD 116
5.7. Dimethyl- and Trimethylcyclohexanones 118
5.8. Bisignate n —»7t* Cotton Effects: Menthone and Isomenthone 124
5.9. Intramolecular Hydrogen Bonding and 2-Oxo-l-/?-menthanol 134
References 136
6. Other Cycloalkanones 139
6.1. Cyclopropane and Cyclopropanone 139
6.2. Cyclobutane and Cyclobutanones 140
6.3. Cyclopentane 148
6.4. Cyclopentanones 154
6.5. Cycloheptane, Cycloheptanones and Larger Rings 173
References 182
7. Saturated Bicyclic Ketones 185
7.1. Decalins (Bicyclo[4.4.0]decanes) 185
7.2. Decalones 189
7.3. Hydrindanes (Bicyclo[4.3.0]nonanes) 207
7.4. Hydrindanones 212
7.5. Other Bicyclo[m.n.0]aIkanones 217
7.6. Spiro[m.n]alkanones 219
7.7. Bridged Bicyclo[m.n.o]alkanones 221
References 227
8. Saturated Polycyclic Ketones 231
8.1. Tricyclic Ketones: Perhydrophenanthrenones and
Perhydroanthracenones 234
8.2. Tetracyclic Ketones: Steroids 235
CONTENTS
ix
8.3. Conformational Distortions in Steroid and Triterpene Ketones 239
8.4. Variable-Temperature CD Studies of Steroid and Triterpene Ketones 253
8.5. Influence of Solvent on the Cotton Effects of Steroid Ketones 262
8.6. Bridged-ring Polycyclic Ketones 265
References 271
9. Isotopically Perturbed Ketones 275
9.1. Deuterated Cyclopentanones 276
9.2. Deuterated Cyclohexanones 281
9.3. Deuterated Cyclobutanones 291
9.4. Trideuteriomethyl Perturbers 293
9.5. 13C as an Octant Perturber 295
9.6. Isotopic Perturbation of Diketones 297
9.7. Isotopically Perturbed p,y-Unsaturated Ketones 298
9.8. Isotopic Perturbers and the Octant Rule 299
9.9. Other Isotopically Perturbed Chromophores 301
References 301
10. Diketones 305
10.1. Additivity of Octant Contributions vs. Vicinal Interaction 306
10.2. Transannular Orbital Interaction in Nonconjugated Diketones 311
10.3. Remote Diketones: y- and 6-Diones 317
10.4. Proximal Diketones: P-Diones 321
10.5. Adjacent Diketones: a-Diones 329
References 332
11. Unsaturated and Cyclopropyl Ketones 337
11.1. a,p-Unsaturated Ketones 339
11.2. p,y-Unsaturated Ketones and the Extended Octant Rule 352
11.3. y,5- and 5,e-Unsaturated Ketones and Beyond 371
11.4. Cyclopropyl Ketones 381
References 390
12. Dienes 395
12.1. Olefin Sector Rules 395
12.2. Alkenes: The Current Situation 399
12.3. Conjugated Dienes 400
References 407
13. Biaryls and Helicenes 409
13.1. Benzene Sector Rules 409
13.2. Biaryls as Dissymmetric Chromophores 415
X
CONTENTS
13.3. Helicenes 418
References 420
14. Exciton Coupling and Exciton Chirality 423
14.1. Origin of Exciton Coupling 423
14.2. Orientation Dependence in Exciton Coupling 426
14.3. Exciton Coupling and Circular Dichroism 428
14.4. The Exciton Chirality Rule 430
14.5. Absolute Configuration from Exciton Chirality 431
14.6. Additivity of Pairwise Exciton Couplings in Polychromophore
Systems 439
14.7. Red-shifted Chromophores 440
14.8. Bisignate CD Sign Inversions 440
14.9. Enhanced Sensitivity by Fluorescence-Detected CD 444
14.10. Applications of the Exciton Chirality Rule 445
References 454
Index to Chiroptical Data and Spectra 457
Subject Index 471
|
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| illustrated | Illustrated |
| indexdate | 2024-07-09T18:42:33Z |
| institution | BVB |
| isbn | 0471354058 |
| language | English |
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| physical | XIII, 487 S. Ill., graph. Darst. - Ill., graph. Darst. |
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| series2 | Methods in stereochemical analysis |
| spelling | Lightner, David A. Verfasser aut Organic conformational analysis and stereochemistry from circular dichroism spectroscopy David A. Lightner ; Jerome E. Gurst New York [u.a.] Wiley-VCH 2000 XIII, 487 S. Ill., graph. Darst. - Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Methods in stereochemical analysis Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Konformationsanalyse (DE-588)4164967-9 gnd rswk-swf Zirkulardichroismus (DE-588)4010215-4 gnd rswk-swf Stereochemie (DE-588)4129569-9 gnd rswk-swf Zirkulardichroismus (DE-588)4010215-4 s Konformationsanalyse (DE-588)4164967-9 s DE-604 Organische Verbindungen (DE-588)4043816-8 s Stereochemie (DE-588)4129569-9 s Gurst, Jerome E. Verfasser aut HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009034248&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Lightner, David A. Gurst, Jerome E. Organic conformational analysis and stereochemistry from circular dichroism spectroscopy Organische Verbindungen (DE-588)4043816-8 gnd Konformationsanalyse (DE-588)4164967-9 gnd Zirkulardichroismus (DE-588)4010215-4 gnd Stereochemie (DE-588)4129569-9 gnd |
| subject_GND | (DE-588)4043816-8 (DE-588)4164967-9 (DE-588)4010215-4 (DE-588)4129569-9 |
| title | Organic conformational analysis and stereochemistry from circular dichroism spectroscopy |
| title_auth | Organic conformational analysis and stereochemistry from circular dichroism spectroscopy |
| title_exact_search | Organic conformational analysis and stereochemistry from circular dichroism spectroscopy |
| title_full | Organic conformational analysis and stereochemistry from circular dichroism spectroscopy David A. Lightner ; Jerome E. Gurst |
| title_fullStr | Organic conformational analysis and stereochemistry from circular dichroism spectroscopy David A. Lightner ; Jerome E. Gurst |
| title_full_unstemmed | Organic conformational analysis and stereochemistry from circular dichroism spectroscopy David A. Lightner ; Jerome E. Gurst |
| title_short | Organic conformational analysis and stereochemistry from circular dichroism spectroscopy |
| title_sort | organic conformational analysis and stereochemistry from circular dichroism spectroscopy |
| topic | Organische Verbindungen (DE-588)4043816-8 gnd Konformationsanalyse (DE-588)4164967-9 gnd Zirkulardichroismus (DE-588)4010215-4 gnd Stereochemie (DE-588)4129569-9 gnd |
| topic_facet | Organische Verbindungen Konformationsanalyse Zirkulardichroismus Stereochemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009034248&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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