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Guide to Fluorine NMR for Organic Chemists

by: Dolbier, W. R.

Guide to Fluorine NMR for Organic Chemists

by: Dolbier, W. R.

ISBN 13:
9780470193419
ISBN 10:
0470193417
Format: Hardcover
Copyright: 06/29/2009
Publisher: Wiley

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Summary

Handbook of Fluorine NMR for Organic Chemists provides a single one-stop resource for understanding fluorine and its dramatic effect in spectroscopy. Covering fluorine NMR, as well as the impact of fluorine substituents on proton and carbon NMR, this useful guide can provide the practicing organic chemist with an understanding of how to interpret spectroscopic data for molecules containing fluorine to better characterize their compound's structure. A practical, working guide, this book contains numerous examples of structures and their corresponding fluorine NMR shifts, as well as the effect that fluorine has on proton and carbon NMR shifts.

Preface	p. xiii
General Introduction	p. 1
Why Fluorinated Compounds are Interesting	p. 1
Steric Size	p. 1
Polar Effects	p. 1
Effect of Fluorine Substituents on the Acidity and Basicity of Compounds	p. 2
Effect of Fluorinated Substituents on the Lipophilicity of Molecules	p. 3
Other Effects	p. 4
Analytical Applications in Biomedicinal Chemistry	p. 4
Introduction to Fluorine NMR	p. 4
Chemical Shifts	p. 5
Coupling Constants	p. 6
References	p. 6
An Overview of Fluorine NMR	p. 9
Introduction	p. 9
Fluorine Chemical Shifts	p. 10
Steric Deshielding of Fluorine	p. 12
Solvent Effects on Fluorine Chemical Shifts	p. 13
Overall Summary of Fluorine Chemical Shift Ranges	p. 14
Spin-Spin Coupling Constants to Fluorine	p. 15
Through-Space Coupling	p. 18
Fluorine-Fluorine Coupling	p. 20
Coupling between Fluorine and Hydrogen	p. 20
Coupling between Fluorine and Carbon	p. 21
Second-Order Spectra	p. 22
1H Spectra of Fluoroorganic Compounds	p. 27
13C NMR Spectra of Fluoroorganic Compounds	p. 28
Isotope Effects on Chemical Shifts	p. 29
Advanced Topics	p. 31
Multidimensional 19F NMR	p. 32
References	p. 34
The Single Fluorine Substituent	p. 35
Introduction	p. 35
Chemical Shifts-General Considerations	p. 36
Spin-Spin Coupling Constants-General Considerations	p. 36
Saturated Hydrocarbons	p. 37
Primary Alkyl Fluorides	p. 37
Secondary Alkyl Fluorides	p. 40
Tertiary Alkyl Fluorides	p. 43
Cyclic Alkyl Fluorides	p. 45
Influence of Substituents/Functional Groups	p. 47
Halogen Substitution	p. 47
Alcohol, Ether, Ester, Sulfide, and Sulfone Groups	p. 52
Amino and Ammonium Groups	p. 55
Phosphorous Compounds	p. 56
Silanes	p. 57
Carbonyl Functional Groups	p. 58
1H and 13C NMR Data for Aldehydes, Ketones, and Esters	p. 59
Nitriles	p. 60
1H and 13C NMR Data for Nitriles	p. 61
Alkenes with a Single Fluorine Substituent	p. 61
Hydrocarbon Alkenes	p. 62
Conjugated Alkenyl Systems	p. 64
Allylic Alcohols, Ethers, and Halides	p. 67
Halofluoroalkenes and Fluorovinyl Ethers	p. 67
Multifluoroalkenes	p. 69
¿ß-Unsaturated Carbonyl Compounds	p. 70
Acetylenic Fluorine	p. 75
Allylic, Propargylic, and Benzylic Fluorides	p. 75
1H and 13C NMR Data	p. 75
Fluoroaromatics	p. 75
Monofluoroaromatics	p. 75
Fluoropolycyclic Aromatics: Fluoronaphthalenes	p. 81
Polyfluoroaromatics	p. 82
Fluoroheterocycles	p. 83
Fluoropyridines and Quinolines	p. 88
Fluoropyrroles	p. 89
Fluorofurans and Benzofurans	p. 89
Fluorothiophene and Benzothiophene	p. 90
Fluoroimidazoles and Pyrazoles	p. 92
Other Common Groups with a Single Fluorine Substituent	p. 92
Acyl Fluorides	p. 92
Fluoroformates	p. 94
Sulfinyl and Sulfonyl Fluorides	p. 94
References	p. 94
The CF2 Group	p. 97
Introduction	p. 97
Chemical Shifts-General Considerations	p. 98
Spin-Spin Coupling Constants-General Considerations	p. 99
Saturated Hydrocarbons Containing a CF2 Group	p. 99
Alkanes Bearing a Primary CF2H Group	p. 100
Secondary CF2 Groups	p. 101
Comments on Coupling Constants	p. 103
Pertinent 1H Chemical Shift Data	p. 105
Pertinent 13C NMR Data	p. 107
Influence of Substituents/Functional Groups	p. 108
Halogen Substitution	p. 109
Alcohol, Ether, Thioether, and Related Substituents	p. 111
Compounds with Two Different Heteroatom Groups Attached to CF2 Including Chlorodifluoromethyl Ethers	p. 115
Amines, Phosphines, and Phosphonates	p. 116
Silanes	p. 118
Organometallics	p. 118
Carbonyl Functional Groups	p. 119
Aldehydes and Ketones	p. 119
Carboxylic Acids and Derivatives	p. 120
Nitriles	p. 122
1H and 13C NMR Spectra of Nitriles	p. 122
Bifunctional CF2 Compounds	p. 123
Alkenes and Alkynes	p. 124
Simple Alkenes with Terminal Vinylic CF2 Groups	p. 124
Conjugated Alkenes with Terminal Vinylic CF2 Group	p. 126
Effect of Vicinal Halogen or Ether Function	p. 127
Polyfluoroethylenes	p. 127
The Trifluorovinyl Group	p. 127
¿ß-Unsaturated Carbonyl Systems with a Terminal Vinylic CF2 Group	p. 128
Allylic and Propargylic CF2 Groups	p. 129
Benzenoid Aromatics Bearing a CF2 Group	p. 130
1H and 13C NMR Data	p. 131
Heteroaromatic CF2 Groups	p. 132
Pyridines	p. 132
Furans, Thiophenes, and Pyrroles	p. 132
Imidazoles and Other Heterocyclic CF2H Compounds	p. 133
1H and 13C NMR Data for Heterocyclic-Bound CF2 Groups	p. 133
References	p. 135
The Trifluoromethyl Group	p. 137
Introduction	p. 137
NMR Spectra of Compounds Containing the CF3 Group-General Considerations	p. 137
Saturated Hydrocarbons Bearing a CF2 Group	p. 139
Alkanes Bearing a CF3 Group	p. 139
Cycloalkanes Bearing a CF3 Group	p. 140
1H and 13C NMR Data, General Information	p. 140
Influence of Substituents and Functional Groups	p. 142
Impact of Halogens	p. 143
Ethers, Alcohols, Esters, Sulfides, and Selenides	p. 144
Amines and Phosphines	p. 148
Organometallics	p. 151
Carbonyl Compounds	p. 152
1H and 13C NMR Data	p. 155
Nitriles	p. 157
13C NMR Data for Nitriles	p. 157
Bifunctional Compounds	p. 158
Sulfonic Acid Derivatives	p. 158
Allylic and Propargylic Trifluoromethyl Groups	p. 159
Allylic Trifluoromethyl Groups	p. 159
¿ß-Unsaturated Carbonyl Compounds	p. 163
More Heavily Fluorinated Allylics	p. 165
Propargylic Trifluoromethyl Groups	p. 165
Aryl-Bound Trifluoromethyl Groups	p. 166
13C NMR Data	p. 167
Heteroaryl-Bound Trifluoromethyl Groups	p. 168
Pyridines and Quinolines	p. 168
Pyrroles and Indoles	p. 169
Thiophenes and Benzthiophenes	p. 170
Furans	p. 170
Imidazoles and Benzimidazoles	p. 172
Oxazoles, Thiazoles, Benzoxazoles, and Benzthiazoles	p. 173
Pyrazoles and Pyridazines	p. 174
References	p. 175
More Highly Fluorinated Groups	p. 177
Introduction	p. 177
The 1,1,2- and 1,2,2-Trifluoroethyl Groups	p. 178
The 1,1,2,2-Tetrafluoroethyl and 2,2,3,3-Tetrafluoropropyl Groups	p. 180
The 1,2,2,2-Tetrafluoroethyl Group	p. 183
The Pentafluoroethyl Group	p. 185
Pentafluoroethyl Carbinols	p. 188
Pentafluoroethyl Ethers and Sulfides	p. 188
Pentafluoroethyl Organometallics	p. 189
The 2,2,3,3,3-Pentafluoropropyl Group	p. 189
The 1,1,2,3,3,3-Hexafluoropropyl Group	p. 192
The Hexafluoro-iso-Propyl Group	p. 192
The Heptafluoro-n-Propyl Group	p. 194
The Heptafluoro-iso-Propyl Group	p. 195
The Nonafluoro-n-Butyl Group	p. 195
Fluorous Groups	p. 195
1-Hydro-Perfluoroalkanes	p. 197
Perfluoroalkanes	p. 197
Perfluoro-n-Alkyl Halides	p. 201
Perfluoroalkyl Amines, Ethers, and Carboxylic Acid Derivatives	p. 201
Polyfluoroalkenes	p. 201
Trifluorovinyl Groups	p. 201
Perfluoroalkenes	p. 205
Polyfluorinated Aromatics	p. 206
2,3,5,6-Tetrafluorobenzene Compounds	p. 206
The Pentafluorophenyl Group	p. 206
Polyfluoroheterocyclics	p. 207
Polyfluoropyridines	p. 207
Polyfluorofurans	p. 207
Polyfluorothiophenes	p. 207
Polyfluoropyrimidines	p. 207
References	p. 210
Compounds and Substituents with Fluoride Directly Bound to a Heteroatom	p. 211
Introduction	p. 211
Boron Fluorides	p. 212
Fluorosilanes	p. 213
Nitrogen Fluorides	p. 213
Electrophilic Fluorinating Agents	p. 214
Phosphorous Fluorides	p. 214
Phosphorous (III) Fluorides	p. 214
Phosphorous (V) Fluorides	p. 215
Phosphorous (V) Oxyfluorides	p. 217
Oxygen Fluorides (Hypofluorites)	p. 217
Sulfur Fluorides	p. 218
Inorganic Sulfur Fluorides and Oxyfluorides	p. 218
Aryl and Alkyl SF3 Compounds	p. 219
Dialkylaminosulfur Trifluorides	p. 219
Hypervalent Sulfur Fluorides	p. 221
Related Hypervalent Selenium and Tellurium Fluorides	p. 221
Organic Sulfinyl and Sulfonyl Fluorides	p. 222
The Pentafluorosulfanyl (SF5) Group	p. 222
Saturated Aliphatic Systems	p. 225
Vinylic SF5 Substituents	p. 228
Acetylenic SF5 Substituents	p. 229
Aromatic SF5 Substituents	p. 229
Bromine Trifluoride and Iodine Pentafluoride	p. 230
Aryl Halogen Difluorides and Tetrafluorides	p. 231
Xenon Difluoride	p. 231
References	p. 232
General Index	p. 233
Compound Index	p. 236
Table of Contents provided by Ingram. All Rights Reserved.

Rent More, Save More! Use code: KBRENTAL

5% off 1 book, 7% off 2 books, 10% off 3+ books

Guide to Fluorine NMR for Organic Chemists

Guide to Fluorine NMR for Organic Chemists

9780470193419

0470193417

Summary

Author Biography

Table of Contents

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