Modelling 1 H NMR spectra of organic compounds: theory, applications and NMR prediction software
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| Main Authors: | , |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Chichester
Wiley
2008
|
| Edition: | 1. publ. |
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Includes bibliographical references and index |
| Physical Description: | XII, 380 S. Ill., graph. Darst. 1 CD-ROM (12 cm) |
| ISBN: | 9780470723012 |
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MARC
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| 245 | 1 | 0 | |a Modelling 1 H NMR spectra of organic compounds |b theory, applications and NMR prediction software |c Raymond J. Abraham ; Mehdi Mobli |
| 250 | |a 1. publ. | ||
| 264 | 1 | |a Chichester |b Wiley |c 2008 | |
| 300 | |a XII, 380 S. |b Ill., graph. Darst. |e 1 CD-ROM (12 cm) | ||
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| 500 | |a Includes bibliographical references and index | ||
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Record in the Search Index
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|---|---|
| adam_text | Contents
Preface xi
1 Introduction to *H NMR Chemical Shifts 1
1.1 Historical Background I
1.2 Basic Theory of NMR 3
1.3 The H Chemical Shift 4
1.3.1 Nuclear Shielding and Reference Compounds 4
1.4 H Substituent Chemical Shift (SCS) 5
1.4.1 Two-bond (H.C.X) Effects 6
1.4.2 Three-bond (H.C.C.X) Effects 6
1.4.3 ^HSCSsinOlefinsandAromatics 1
1.5 Long-range Effects on H Chemical Shifts 9
1.5.1 Steric (van der Waals) Effects 10
1.5.2 Electric Field Effects 10
1.5.3 n-Electron Effects 12
1.5.4 Hydrogen Bonding Shifts 17
1.6 Tables of H Chemical Shifts of Common Unsaturated and Saturated
Cyclic Systems 17
References 20
2 Interpretation of H NMR Coupling Patterns 23
2.1 Fine Structure due to HH Coupling 23
2.2 The Analysis of NMR Spectra 26
2.2.1 Nomenclature of the Spin System, Chemical and Magnetic
Equivalence 26
2.2.2 Two Interacting Nuclei, the AB Spectrum 29
2.2.3 Three Interacting Nuclei, the ABX Spectrum 32
2.2.4 Four Interacting Nuclei 32
2.2.5 Iterative Computer Analysis 37
2.2.6 Automatic Iteration of Complex Spectra 43
2.3 The Mechanism of Spin-Spin Coupling 44
2.3.1 GeminalHH Couplings (2JHH) 45
2.3.2 Vicinal HH Couplings (3JHH) 49
2.3.3 Ab initio Calculated Couplings 52
2.3.4 Long-range HH Couplings 55
vi Contents
2.4 HF Couplings 57
2.4.1 Geminal HF Couplings (2JHF) 57
2.4.2 Vicinal HF Couplings 58
2.4.3 Long-range HF Couplings 61
References 63
3 Chemical Shift Calculations and Molecular Structure 67
3.1 Introduction 67
3.2 Quantum Mechanical Calculations of1 H Chemical Shifts 68
3.3 The Database Approach 69
3.4 Semi-empirical Calculations 70
3.5 Theory of the CHARGE Program 72
3.5.1 Through Bond Effects 72
3.5.2 H Chemical Shifts of Substituted Methanes and
Ethanes 74
3.5.3 Through Space Effects 11
3.5.4 Hydrogen Bonding Shifts 78
3.5.5 Aromatic Compounds 80
References 82
4 Modelling H Chemical Shifts, Hydrocarbons 85
4.1 Introduction 85
4.2 Alkane Chemical Shifts 86
4.2.1 H..H and C..H Steric Interactions 86
4.2.2 The Methyl Effect 89
4.2.3 C—C BondAnisotropy 90
4.2.4 Observed versus Calculated Shifts 92
4.3 Alkene Chemical Shifts 100
4.3.1 Introduction 100
4.3.2 C=C Bond Anisotropy and Shielding 102
4.3.3 Observed versus Calculated Shifts 104
4.4 Alkyne Chemical Shifts 116
4.4.1 Introduction 116
4.4.2 C^C Bond Anisotropy and Shielding 116
4.4.3 Observed versus Calculated Shifts 118
4.4.4 Acetylene SCSs 121
4.4.5 Contributions to the Acetylene SCSs 126
4.4.6 Naphthyl and PhenanthrylAcetylenes 128
4.5 Summary 129
References 130
5 Modelling H Chemical Shifts, Aromatics 133
5.1 Aromatic Hydrocarbons 133
5.1.1 Introduction 133
5.1.2 Ring Currents, it-Electron Densities and Steric Effects 135
5.1.3 Observed versus Calculated Shifts 139
Contents vü
5.2 Heteroaromatics 148
5.2.1 Introduction 148
5.2.2 Theory and Application to Heteroaromatics 149
5.2.3 Observed versus Calculated Shifts 155
5.2.4 Ring Currents and n -Electron Shifts 159
5.3 Summary 166
References 167
6 Modelling H Chemical Shifts, Monovalent Substitueras 169
6.1 Introduction 169
6.2 Fluorine Substituent Chemical Shifts 169
6.2.1 Electric Field Theory 170
6.2.2 Fluoroalkanes 112
6.2.3 Fluoroalkenes and Aromatics 111
6.3 Steric, Anisotropie and Electric Field Effects in Cl, Br and I SCSs 179
6.3.1 Introduction 179
6.3.2 Aromatic Halides 182
6.3.3 Alkyl Halides 184
6.3.4 Contributions to the H SCSs in Halocyclohexanes 191
6.3.5 Steric Coefficients for Halogens 197
6.4 Alcohols and Phenols 199
6.4.7 Introduction 199
6.4.2 Alcohols and Diols 200
6.4.3 Phenols 209
6.5 Amines 215
6.5.1 Introduction 215
6.5.2 Theory and Application to Amines 216
6.5.3 Observed versus Calculated Shifts 217
6.5.4 Conformational Analysis 217
6.6 Cyanides 224
6.6.1 Introduction 224
6.6.2 Theory and Application to the Cyano Group 225
6.6.3 Observed versus Calculated Shifts 226
6.6.4 Cyano SCSs 231
6.7 Nitro Compounds 233
6.7.7 Introduction 233
6.7.2 Theory and Application to Nitro Compounds 234
6.7.3 Observed versus Calculated Shifts 236
6.7.4 SCSs of the Nitro Group 237
6.7.5 Conformational Analysis 238
6.8 Summary 241
References 242
7 Modelling H Chemical Shifts, Divalent Substituent* 247
7.1 Introduction 247
7.2 Aldehydes and Ketones 247
viü Contents
7.2.1 Aliphatic Aldehydes and Ketones 247
7.2.2 Aromatic Aldehydes and Ketones 256
7.2.3 Conformational Analysis 261
7.3 Esters 263
7.3.1 Introduction 263
7.3.2 Theory, Application to Esters 264
7.3.3 Observed versus Calculated Shifts 266
7.4 Amides 273
7.4.1 Introduction 273
7.4.2 Theory, Application to Amides 21A
7.4.3 Aliphatic and Cyclic Amides 275
7.4.4 Aromatic Amides 279
7.5 Steric and Electric Field Effects in Acyclic and Cyclic Ethers 282
7.5.1 Introduction 282
7.5.2 Theory, Application to Ethers 283
7.5.3 Oxygen SCSs in Ethers 284
7.5.4 Observed versus Calculated Shifts 286
7.6 Sulfoxides and Sulfones 290
7.6.1 Introduction 290
7.6.2 Theory, Application to Sulfoxides and Sulfones 290
7.6.3 Molecular Geometries 290
7.6.4 Observed versus Calculated Shifts 291
7.7 Summary 297
References 298
H Chemical Shifts and Structural Chemistry 303
8.1 Introduction 303
8.2 Electronic Structure Calculations 304
8.2.1 Basis Sets 306
8.3 Molecular Mechanics Calculations 306
8.3.1 Conformer Generation 307
8.4 Molecular Geometries and *H Chemical Shift Calculations 309
8.4.1 Methyl Anthracene-Ç-carboxylate 310
8.4.2 N-Formyl Aniline (1) 312
8.4.3 Benzosuberone (2) 313
8.5 Rate Processes and NMR Spectra 314
8.5.7 Theory 314
8.5.2 Amide Rotation 317
8.5.3 Proton Exchange Equilibria 318
8.5.4 Rotation about Single Bonds, Ring Inversion Processes 319
8.6 Solvent Effects 322
8.6.1 Introduction 322
8.6.2 Non-polar Compounds 324
8.6.3 Polar Aprotic Compounds 325
8.6.4 Protic Compounds 331
Contents ix
8.6.5 Diols and Polyhydroxy Compounds 340
8.6.6 Chemical Shift Contributions 340
8.7 Summary 345
References 346
9 A Practical Approach to *H NMR Calculation and Prediction 349
9.1 Introduction 349
9.2 A Step-by-Step Description of Calculating *H NMR Spectra 350
9.2.1 Molecular Modelling and Conformational Searching — PCModel 350
9.2.2 Calculating lH Chemical Shifts and J-Coupling
Constants -HNMRSPEC 357
9.2.3 Displaying the Calculated // Spectrum - 1HPLOT 361
9.2.4 Advanced Use of HNMRSPEC_S 362
9.2.5 Iteration of 2nd Order // Spectrafrom Pre-specified 8s and
Js-LAOCOON 363
9.3 Automated Spectral Prediction Using the NMRPredict Software 365
9.4 Concluding Remarks 368
Index 369
|
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| spelling | Abraham, Raymond J. 1933- Verfasser (DE-588)120530597 aut Modelling 1 H NMR spectra of organic compounds theory, applications and NMR prediction software Raymond J. Abraham ; Mehdi Mobli 1. publ. Chichester Wiley 2008 XII, 380 S. Ill., graph. Darst. 1 CD-ROM (12 cm) txt rdacontent n rdamedia nc rdacarrier Includes bibliographical references and index Proton magnetic resonance spectroscopy Organic compounds Spectra Organic compounds Structure Protonen-NMR-Spektroskopie (DE-588)4354421-6 gnd rswk-swf Molekülstruktur (DE-588)4170383-2 gnd rswk-swf Organische Verbindungen (DE-588)4043816-8 gnd rswk-swf Protonen-NMR-Spektroskopie (DE-588)4354421-6 s Organische Verbindungen (DE-588)4043816-8 s Molekülstruktur (DE-588)4170383-2 s DE-604 Mobli, Mehdi Verfasser aut HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017127571&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Abraham, Raymond J. 1933- Mobli, Mehdi Modelling 1 H NMR spectra of organic compounds theory, applications and NMR prediction software Proton magnetic resonance spectroscopy Organic compounds Spectra Organic compounds Structure Protonen-NMR-Spektroskopie (DE-588)4354421-6 gnd Molekülstruktur (DE-588)4170383-2 gnd Organische Verbindungen (DE-588)4043816-8 gnd |
| subject_GND | (DE-588)4354421-6 (DE-588)4170383-2 (DE-588)4043816-8 |
| title | Modelling 1 H NMR spectra of organic compounds theory, applications and NMR prediction software |
| title_auth | Modelling 1 H NMR spectra of organic compounds theory, applications and NMR prediction software |
| title_exact_search | Modelling 1 H NMR spectra of organic compounds theory, applications and NMR prediction software |
| title_full | Modelling 1 H NMR spectra of organic compounds theory, applications and NMR prediction software Raymond J. Abraham ; Mehdi Mobli |
| title_fullStr | Modelling 1 H NMR spectra of organic compounds theory, applications and NMR prediction software Raymond J. Abraham ; Mehdi Mobli |
| title_full_unstemmed | Modelling 1 H NMR spectra of organic compounds theory, applications and NMR prediction software Raymond J. Abraham ; Mehdi Mobli |
| title_short | Modelling 1 H NMR spectra of organic compounds |
| title_sort | modelling 1 h nmr spectra of organic compounds theory applications and nmr prediction software |
| title_sub | theory, applications and NMR prediction software |
| topic | Proton magnetic resonance spectroscopy Organic compounds Spectra Organic compounds Structure Protonen-NMR-Spektroskopie (DE-588)4354421-6 gnd Molekülstruktur (DE-588)4170383-2 gnd Organische Verbindungen (DE-588)4043816-8 gnd |
| topic_facet | Proton magnetic resonance spectroscopy Organic compounds Spectra Organic compounds Structure Protonen-NMR-Spektroskopie Molekülstruktur Organische Verbindungen |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017127571&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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