Modelling 1H NMR spectra of organic compounds theory and applications

Library	Item Barcode	Call Number	Material Type	Item Category 1	Status
Searching... PSZ JB	30000010194573	CP 012178	Computer File Accompanies Open Access Book	Compact Disc Accompanies Open Access Book	Searching... Unknown
Searching... PSZ JB	30000003503574	CP 012178	Computer File Accompanies Open Access Book	Compact Disc Accompanies Open Access Book	Searching... Unknown
Searching... PSZ KL	30000003503582	CP 012178	Computer File Accompanies Open Access Book	Compact Disc Accompanies Open Access Book	Searching... Unknown

Provides a theoretical introduction to graduate scientists and industrial researchers towards the understanding of the assignment of 1H NMR spectra Discusses, and includes on enclosed CD, one of the best, the fastest and most applicable pieces of NMR prediction software available Allows students of organic chemistry to solve problems on 1H NMR with access to over 500 assigned spectra

Author Notes

Raymond Abraham was appointed lecturer in organic chemistry at the The University of Liverpool in 196. Since then he has remained at Liverpool, with two fellowships taken at the Mellon Institute and the University of Trondheim in 1966 and 1979 respectively, now holding the position of Emeritus Professor. His research interests include: Molecular modelling and Proton Chemical Shift Predictions; Non-bonded and Hydrogen bonding Interactions and Conformational Analysis; and Lanthanide Induced Shifts and Molecular Geometries. He has over 300 publications including three books and ten reviews.

Mehdi Mobli is currently a post-doctoral research fellow at Manchester University, having completed his B.Sc in chemical engineering at Chalmers University of Technology in Sweden and his Ph.D. with Professor Abraham at The University of Liverpool. He has published 10 papers mainly in conjunction with Professor Abraham, all focused on the topic of this text.

Preface	p. xi
1 Introduction to [superscript 1]H NMR Chemical Shifts	p. 1
1.1 Historical Background	p. 1
1.2 Basic Theory of NMR	p. 3
1.3 The [superscript 1]H Chemical Shift	p. 4
1.3.1 Nuclear Shielding and Reference Compounds	p. 4
1.4 [superscript 1]H Substituent Chemical Shift (SCS)	p. 5
1.4.1 Two-bond (H.C.X) Effects	p. 6
1.4.2 Three-bond (H.C.C.X) Effects	p. 6
1.4.3 [superscript 1]H SCSs in Olefins and Aromatics	p. 7
1.5 Long-range Effects on [superscript 1]H Chemical Shifts	p. 9
1.5.1 Steric (van der Waals) Effects	p. 10
1.5.2 Electric Field Effects	p. 10
1.5.3 [pi]-Electron Effects	p. 12
1.5.4 Hydrogen Bonding Shifts	p. 17
1.6 Tables of [superscript 1]H Chemical Shifts of Common Unsaturated and Saturated Cyclic Systems	p. 17
References	p. 20
2 Interpretation of [superscript 1]H NMR Coupling Patterns	p. 23
2.1 Fine Structure due to HH Coupling	p. 23
2.2 The Analysis of NMR Spectra	p. 26
2.2.1 Nomenclature of the Spin System, Chemical and Magnetic Equivalence	p. 26
2.2.2 Two Interacting Nuclei, the AB Spectrum	p. 29
2.2.3 Three Interacting Nuclei, the ABX Spectrum	p. 32
2.2.4 Four Interacting Nuclei	p. 32
2.2.5 Iterative Computer Analysis	p. 37
2.2.6 Automatic Iteration of Complex Spectra	p. 43
2.3 The Mechanism of Spin-Spin Coupling	p. 44
2.3.1 Geminal HH Couplings ([superscript 2]J[subscript HH])	p. 45
2.3.2 Vicinal HH Couplings ([superscript 3]J[subscript HH])	p. 49
2.3.3 Ab initio Calculated Couplings	p. 52
2.3.4 Long-range HH Couplings	p. 55
2.4 HF Couplings	p. 57
2.4.1 Geminal HF Couplings ([superscript 2]J[subscript HF])	p. 57
2.4.2 Vicinal HF Couplings	p. 58
2.4.3 Long-range HF Couplings	p. 61
References	p. 63
3 Chemical Shift Calculations and Molecular Structure	p. 67
3.1 Introduction	p. 67
3.2 Quantum Mechanical Calculations of [superscript 1]H Chemical Shifts	p. 68
3.3 The Database Approach	p. 69
3.4 Semi-empirical Calculations	p. 70
3.5 Theory of the CHARGE Program	p. 72
3.5.1 Through Bond Effects	p. 72
3.5.2 [superscript 1]H Chemical Shifts of Substituted Methanes and Ethanes	p. 74
3.5.3 Through Space Effects	p. 77
3.5.4 Hydrogen Bonding Shifts	p. 78
3.5.5 Aromatic Compounds	p. 80
References	p. 82
4 Modelling [superscript 1]H Chemical Shifts, Hydrocarbons	p. 85
4.1 Introduction	p. 85
4.2 Alkane Chemical Shifts	p. 86
4.2.1 H..H and C..H Steric Interactions	p. 86
4.2.2 The Methyl Effect	p. 89
4.2.3 C-C Bond Anisotropy	p. 90
4.2.4 Observed versus Calculated Shifts	p. 92
4.3 Alkene Chemical Shifts	p. 100
4.3.1 Introduction	p. 100
4.3.2 C=C Bond Anisotropy and Shielding	p. 102
4.3.3 Observed versus Calculated Shifts	p. 104
4.4 Alkyne Chemical Shifts	p. 116
4.4.1 Introduction	p. 116
4.4.2 C[identical with]C Bond Anisotropy and Shielding	p. 116
4.4.3 Observed versus Calculated Shifts	p. 118
4.4.4 Acetylene SCSs	p. 121
4.4.5 Contributions to the Acetylene SCSs	p. 126
4.4.6 Naphthyl and Phenanthryl Acetylenes	p. 128
4.5 Summary	p. 129
References	p. 130
5 Modelling [superscript 1]H Chemical Shifts, Aromatics	p. 133
5.1 Aromatic Hydrocarbons	p. 133
5.1.1 Introduction	p. 133
5.1.2 Ring Currents, [pi]-Electron Densities and Steric Effects	p. 135
5.1.3 Observed versus Calculated Shifts	p. 139
5.2 Heteroaromatics	p. 148
5.2.1 Introduction	p. 148
5.2.2 Theory and Application to Heteroaromatics	p. 149
5.2.3 Observed versus Calculated Shifts	p. 155
5.2.4 Ring Currents and [pi]-Electron Shifts	p. 159
5.3 Summary	p. 166
References	p. 167
6 Modelling [superscript 1]H Chemical Shifts, Monovalent Substituents	p. 169
6.1 Introduction	p. 169
6.2 Fluorine Substituent Chemical Shifts	p. 169
6.2.1 Electric Field Theory	p. 170
6.2.2 Fluoroalkanes	p. 172
6.2.3 Fluoroalkenes and Aromatics	p. 177
6.3 Steric, Anisotropic and Electric Field Effects in Cl, Br and I SCSs	p. 179
6.3.1 Introduction	p. 179
6.3.2 Aromatic Halides	p. 182
6.3.3 Alkyl Halides	p. 184
6.3.4 Contributions to the [superscript 1]H SCSs in Halocyclohexanes	p. 191
6.3.5 Steric Coefficients for Halogens	p. 197
6.4 Alcohols and Phenols	p. 199
6.4.1 Introduction	p. 199
6.4.2 Alcohols and Diols	p. 200
6.4.3 Phenols	p. 209
6.5 Amines	p. 215
6.5.1 Introduction	p. 215
6.5.2 Theory and Application to Amines	p. 216
6.5.3 Observed versus Calculated Shifts	p. 217
6.5.4 Conformational Analysis	p. 217
6.6 Cyanides	p. 224
6.6.1 Introduction	p. 224
6.6.2 Theory and Application to the Cyano Group	p. 225
6.6.3 Observed versus Calculated Shifts	p. 226
6.6.4 Cyano SCSs	p. 231
6.7 Nitro Compounds	p. 233
6.7.1 Introduction	p. 233
6.7.2 Theory and Application to Nitro Compounds	p. 234
6.7.3 Observed versus Calculated Shifts	p. 236
6.7.4 SCSs of the Nitro Group	p. 237
6.7.5 Conformational Analysis	p. 238
6.8 Summary	p. 241
References	p. 242
7 Modelling [superscript 1]H Chemical Shifts, Divalent Substituents	p. 247
7.1 Introduction	p. 247
7.2 Aldehydes and Ketones	p. 247
7.2.1 Aliphatic Aldehydes and Ketones	p. 247
7.2.2 Aromatic Aldehydes and Ketones	p. 256
7.2.3 Conformational Analysis	p. 261
7.3 Esters	p. 263
7.3.1 Introduction	p. 263
7.3.2 Theory, Application to Esters	p. 264
7.3.3 Observed versus Calculated Shifts	p. 266
7.4 Amides	p. 273
7.4.1 Introduction	p. 273
7.4.2 Theory, Application to Amides	p. 274
7.4.3 Aliphatic and Cyclic Amides	p. 275
7.4.4 Aromatic Amides	p. 279
7.5 Steric and Electric Field Effects in Acyclic and Cyclic Ethers	p. 282
7.5.1 Introduction	p. 282
7.5.2 Theory, Application to Ethers	p. 283
7.5.3 Oxygen SCSs in Ethers	p. 284
7.5.4 Observed versus Calculated Shifts	p. 286
7.6 Sulfoxides and Sulfones	p. 290
7.6.1 Introduction	p. 290
7.6.2 Theory, Application to Sulfoxides and Sulfones	p. 290
7.6.3 Molecular Geometries	p. 290
7.6.4 Observed versus Calculated Shifts	p. 291
7.7 Summary	p. 297
References	p. 298
8 [superscript 1]H Chemical Shifts and Structural Chemistry	p. 303
8.1 Introduction	p. 303
8.2 Electronic Structure Calculations	p. 304
8.2.1 Basis Sets	p. 306
8.3 Molecular Mechanics Calculations	p. 306
8.3.1 Conformer Generation	p. 307
8.4 Molecular Geometries and [superscript 1]H Chemical Shift Calculations	p. 309
8.4.1 Methyl Anthracene-9-carboxylate	p. 310
8.4.2 N-Formyl Aniline (1)	p. 312
8.4.3 Benzosuberone (2)	p. 313
8.5 Rate Processes and NMR Spectra	p. 314
8.5.1 Theory	p. 314
8.5.2 Amide Rotation	p. 317
8.5.3 Proton Exchange Equilibria	p. 318
8.5.4 Rotation about Single Bonds, Ring Inversion Processes	p. 319
8.6 Solvent Effects	p. 322
8.6.1 Introduction	p. 322
8.6.2 Non-polar Compounds	p. 324
8.6.3 Polar Aprotic Compounds	p. 325
8.6.4 Protic Compounds	p. 331
8.6.5 Diols and Polyhydroxy Compounds	p. 340
8.6.6 Chemical Shift Contributions	p. 340
8.7 Summary	p. 345
References	p. 346
9 A Practical Approach to [superscript 1]H NMR Calculation and Prediction	p. 349
9.1 Introduction	p. 349
9.2 A Step-by-Step Description of Calculating [superscript 1]H NMR Spectra	p. 350
9.2.1 Molecular Modelling and Conformational Searching - PCModel	p. 350
9.2.2 Calculating [superscript 1]H Chemical Shifts and J-Coupling Constants - HNMRSPEC	p. 357
9.2.3 Displaying the Calculated [superscript 1]H Spectrum - IHPLOT	p. 361
9.2.4 Advanced Use of HNMRSPEC_S	p. 362
9.2.5 Iteration of 2nd Order [superscript 1]H Spectra from Pre-specified [delta]s and Js - LAOCOON	p. 363
9.3 Automated Spectral Prediction Using the NMRPredict Software	p. 365
9.4 Concluding Remarks	p. 368
Index	p. 369

Available:*

On Order

Summary

Summary

Author Notes

Table of Contents