Guide to fluorine NMR for organic chemists:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Hoboken, NJ
Wiley
2009
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Includes index |
| Beschreibung: | XIV, 256 S. graph. Darst. |
| ISBN: | 9780470193419 |
Internformat
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| 245 | 1 | 0 | |a Guide to fluorine NMR for organic chemists |c William R. Dolbier |
| 264 | 1 | |a Hoboken, NJ |b Wiley |c 2009 | |
| 300 | |a XIV, 256 S. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
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| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Includes index | ||
| 650 | 4 | |a Fluorine compounds |x Spectra | |
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| 999 | |a oai:aleph.bib-bvb.de:BVB01-018669704 | ||
Datensatz im Suchindex
| _version_ | 1804140762055573504 |
|---|---|
| adam_text | CONTENTS
PREFACE
xiii
1 GENERAL
INTRODUCTION
1
1.1.
Why
Fluorinated
Compounds are Interesting
/ 1
1.1.1.
StericSize
/ 1
1.1.2.
Polar Effects
/ 1
1.1.3.
Effect of Fluorine Substituents on the Acidity
and Basicity of Compounds
/ 2
1.1.4.
Effect of
Fluorinated
Substituents
on the Lipophilicity of Molecules
/ 3
1.1.5.
Other Effects
/ 4
1.1.6.
Analytical Applications in Biomedicinal
Chemistry
/ 4
1.2.
Introduction to Fluorine NMR
/ 4
1.2.1.
Chemical Shifts
/ 5
1.2.2.
Coupling Constants
/ 6
References
/ 6
2
AN OVERVIEW OF FLUORINE NMR
9
2.1.
Introduction
/ 9
2.2.
Fluorine Chemical Shifts
/ 10
VÍ
CONTENTS
2.2.1.
Steric Deshielding
of Fluorine
/ 12
2.2.2.
Solvent Effects on Fluorine Chemical
Shifts
/ 13
2.2.3.
Overall Summary of Fluorine Chemical Shift
Ranges
/14
2.3.
Spin-Spin Coupling Constants to Fluorine
/ 15
2.3.1.
Through-Space Coupling
/ 18
2.3.2.
Fluorine-Fluorine Coupling
/ 20
2.3.3.
Coupling between Fluorine and Hydrogen
/ 20
2.3.4.
Coupling between Fluorine and Carbon
/ 21
2.3.5.
Second-Order Spectra
/ 22
2.4.
!H Spectra of Fluoroorganic Compounds
/ 27
2.5.
13C NMR Spectra of Fluoroorganic Compounds
/ 28
2.6.
Isotope Effects on Chemical Shifts
/ 29
2.7.
Advanced Topics
/ 31
2.7.1.
Multidimensional 19F NMR
/ 32
References
/ 34
3
THE SINGLE FLUORINE
SUBSTITUENT
35
3.1.
Introduction
/ 35
3.1.1.
Chemical Shifts
—
General Considerations
/ 36
3.1.2.
Spin-Spin Coupling Constants
—
General
Considerations
/ 36
3.2.
Saturated Hydrocarbons
/ 37
3.2.1.
Primary
Alkyl
Fluorides
/ 37
3.2.2.
Secondary
Alkyl
Fluorides
/ 40
3.2.3.
Tertiary
Alkyl
Fluorides
/ 43
3.2.4.
Cyclic
Alkyl
Fluorides
/ 45
3.3.
Influence of Substituents/Functional Groups
/ 47
3.3.1.
Halogen Substitution
/ 47
3.3.2.
Alcohol, Ether, Ester,
Sulfide,
and Sulfone
Groups
/ 52
3.3.3.
Amino
and Ammonium Groups
/ 55
3.3.4.
Phosphorous Compounds
/ 56
3.3.5.
Silanes
/ 57
3.4.
Carbonyl Functional Groups
/ 58
3.4.1.
Ή
and 13C NMR Data for Aldehydes, Ketones,
and Esters
/ 59
CONTENTS
VU
3.5.
Nitrites
/ 60
3.5.1.
H
and 13C NMR Data for Nitrites
/ 61
3.6.
Alkenes with a Single Fluorine
Substituent
/ 61
3.6.1.
Hydrocarbon Alkenes
/ 62
3.6.2.
Conjugated Alkenyl Systems
/ 64
3.6.3.
Allylic Alcohols, Ethers, and Halides
/ 67
3.6.4.
Halofluoroalkenes and
Fluorovinyl
Ethers
/ 67
3.6.5.
Multifluoroalkenes
/ 69
3.6.6.
α,β
-Unsaturated
Carbonyl Compounds
/ 70
3.7.
Acetylenie
Fluorine
/ 75
3.8.
Allylic, Propargylic, and Benzylic Fluorides
/ 75
3.8.1. .
Ή
and 13C NMR Data
/ 75
3.9.
Fluoroaromatics
/ 75
3.9.1.
Monofluoroaromatics
/ 75
3.9.2.
Fluoropolycyclic Aromatics:
Fluoronaphthalenes
/ 81
3.9.3.
Polyfluoroaromatics
/ 82
3.10.
Fluoroheterocycles
/ 83
3.10.1.
Fluoropyridines and Quinolines
/ 88
3.10.2.
Fluoropyrroles
/ 89
3.10.3.
Fluorofurans
and Benzofurans
/ 89
3.10.4.
Fluorothiophene and Benzothiophene
/ 90
3.10.5.
Fluoroimidazoles and Pyrazoles
/ 92
3.11.
Other Common Groups with a Single Fluorine
Substituent
/ 92
3.11.1.
Acyl Fluorides
/ 92
3.11.2.
Fluoroformates
/ 94
3.11.3.
Sulfinyl and Sulfonyl Fluorides
/ 94
References
/ 94
4
THE CF2 GROUP
97
4.1.
Introduction
/ 97
4.1.1.
Chemical Shifts
—
General Considerations
/ 98
4.1.2.
Spin-Spin Coupling Constants
—
General
Considerations
/ 99
4.2.
Saturated Hydrocarbons Containing a CF2 Group
/ 99
4.2.1.
Alkanes Bearing a Primary CF2H Group
/ 100
4.2.2.
Secondary CF2 Groups
/ 101
VÜi CONTENTS
4.2.3.
Comments on Coupling Constants
/ 103
4.2.4.
Pertinent
Ή
Chemical Shift Data
/ 105
4.2.5.
Pertinent 13C NMR Data
/ 107
4.3.
Influence of Substituents/Functional Groups
/ 108
4.3.1.
Halogen Substitution
/ 109
4.3.2.
Alcohol, Ether, Thioether, and Related
Substituents /111
4.3.3.
Compounds with Two Different
Heteroatom
Groups Attached to CF2 Including
Chlorodifluoromethyl Ethers
/ 115
4.3.4.
Amines, Phosphines, and Phosphonates
/116
4.3.5.
Silanes
/ 118
4.3.6.
Organometallics
/ 118
4.4.
Carbonyl Functional Groups
/ 119
4.4.1.
Aldehydes and Ketones
/ 119
4.4.2.
Carboxylic Acids and Derivatives
/ 120
4.5.
Nitriles
/ 122
4.5.1.
Ή
and 13C NMR Spectra of Nitriles
/ 122
4.6.
Bifunctional CF2 Compounds
/ 123
4.7.
Alkenes and Alkynes
/ 124
4.7.1.
Simple Alkenes with Terminal Vinylic CF2
Groups
/ 124
4.7.2.
Conjugated Alkenes with Terminal Vinylic CF2
Group
/ 126
4.7.3.
Effect of Vicinal Halogen or Ether Function
/ 127
4.7.4.
Polyfluoroethylenes
/ 127
4.7.5.
The Trifluorovinyl Group
/ 127
4.7.6.
α,β
-Unsaturated
Carbonyl Systems with a
Terminal Vinylic CF2 Group
/ 128
4.7.7.
Allylic and Propargylic CF2 Groups
/ 129
4.8.
Benzenoid Aromatics Bearing a CF2 Group
/ 130
4.8.1.
Ή
and 13C NMR Data
/ 131
4.9.
Heteroaromatic CF2 Groups
/ 132
4.9.1.
Pyridines
/ 132
4.9.2.
Furans,
Thiophenes, and Pyrroles
/ 132
4.9.3.
Imidazoles and Other Heterocyclic CF2H
Compounds
/ 133
CONTENTS
ІХ
4.9.4.
Ή
and 13C NMR Data for Heterocyclic-Bound
CF2 Groups
/ 133
References
/ 135
5
THE TRIFLUOROMETHYL GROUP
137
5.1.
Introduction
/137
5.1.1.
NMR Spectra of Compounds Containing the CF3
Group
—
General Considerations
/137
5.2.
Saturated Hydrocarbons Bearing a CF3 Group
/ 139
5.2.1.
Alkanes Bearing a CF3 Group
/ 139
5.2.2.
Cycloalkanes Bearing a CF3 Group
/ 140
5.2.3.
Ή
and 13C NMR Data, General Information
/ 140
5.3.
Influence of Substituents and Functional Groups
/ 142
5.3.1.
Impact of Halogens
/ 143
5.3.2.
Ethers, Alcohols, Esters,
Sulfides,
and
Selenides
/ 144
5.3.3.
Amines and Phosphines
/ 148
5.3.4.
Organometallics
/ 151
5.4.
Carbonyl Compounds
/ 152
5.4.1.
Ή
and 13C NMR Data
/ 155
5.5.
Nitriles
/ 157
5.5.1.
13C NMR Data for Nitriles
/ 157
5.6.
Bifunctional Compounds
/ 158
5.7.
Sulfonic Acid Derivatives
/ 158
5.8.
Allylic and Propargylic Trifluoromethyl Groups
/ 159
5.8.1.
Allylic Trifluoromethyl Groups
/ 159
5.8.2.
α,β
-Unsaturated
Carbonyl Compounds
/ 163
5.8.3.
More Heavily
Fluorinated Allylics / 165
5.8.4.
Propargylic Trifluoromethyl Groups
/ 165
5.9.
Aryl-Bound Trifluoromethyl Groups
/ 166
5.9.1.
13C NMR Data
/ 167
5.10.
Heteroaryl-Bound Trifluoromethyl Groups
/ 168
5.10.1.
Pyridines and Quinolines
/ 168
5.10.2.
Pyrroles and
índoles
/ 169
5.10.3.
Thiophenes and Benzthiophenes
/ 170
5,$0.4.
Furans
/ 170
5.10.5.
Imidazoles and Benzimidazoles
/ 172
CONTENTS
5.10.6. Oxazoles, Thiazoles, Benzoxazoles, and
Benzthiazoles / 173
5.10.7. Pyrazoles and Pyridazines / 174
References
/ 175
6
MORE HIGHLY
FLUORINATED
GROUPS
177
6.1.
Introduction
/ 177
6.2.
The
1,1,2-
and 1,2,2-Trifluoroethyl Groups
/ 178
6.3.
The 1,1,2,2-Tetrafluoroethyl and 2,2,3,3-Tetrafluoropropyl
Groups
/ 180
6.4.
The 1,2,2,2-Tetranuoroethyl Group
/ 183
6.5.
The Pentafluoroethyl Group
/ 185
6.5.1.
Pentafluoroethyl Carbinols
/ 188
6.5.2.
Pentafluoroethyl Ethers and
Sulfides / 188
6.5.3.
Pentafluoroethyl Organometallics
/ 189
6.6.
The 2,2,3,3,3-Pentafluoropropyl Group
/ 189
6.7.
The 1,1,2,3,3,3-Hexafluoropropyl Group
/ 192
6.8.
The Hexafluoro-iso-Propyl Group
/192
6.9.
The Heptafluoro-n-Propyl Group
/ 194
6.10.
The Heptafluoro-iso-Propyl Group
/ 195
6.11.
The Nonafluoro-n-Butyl Group
/ 195
6.12.
Fluorous Groups
/ 195
6.13.
l-Hydro-Perfluoroalkanes
/ 197
6.14.
Perfluoroalkanes
/ 197
6.15.
Perfluoro-w-Alkyl Halides
/ 201
6.16.
Perfluoroalkyl Amines, Ethers, and Carboxylic Acid
Derivatives
/ 201
6.17.
Polyfluoroalkenes
/ 201
6.17.1.
Trifluorovinyl Groups
/ 201
6.17.2.
Perfluoroalkenes
/ 205
6.18.
Polyfluorinated Aromatics
/ 206
6.18.1.
2,3,5,6-Tetrafluorobenzene Compounds
/ 206
6.18.2.
The Pentafluorophenyl Group
/ 206
6.19.
Polyfluoroheterocyclics
/ 207
6.19.1.
Polyfluoropyridines
/207
6.19.2.
Polyfluorofurans
/ 207
CONTENTS
ХІ
6.19.3.
Polyfluorothiophenes
/ 207
6.19.4. Polyfluoropyrimidines / 207
References
/ 210
7
COMPOUNDS AND SUBSTITUENTS WITH
FLUORIDE DIRECTLY BOUND TO
A
HETEROATOM 211
7.1.
Introduction
/ 211
7.2.
Boron Fluorides
/ 212
7.3.
Fluorosilanes
/ 213
7.4.
Nitrogen Fluorides
/ 213
7.4.1.
Electrophilic Fluorinating Agents
/ 214
7.5.
Phosphorous Fluorides
/ 214
7.5.1.
Phosphorous (III) Fluorides
/ 214
7.5.2.
Phosphorous (V) Fluorides
/ 215
7.5.3.
Phosphorous (V) Oxyfluorides
/ 217
7.6.
Oxygen Fluorides (Hypofluorites)
/ 217
7.7.
Sulfur Fluorides
/ 218
7.7.1.
Inorganic Sulfur Fluorides and Oxyfluorides
/ 218
7.7.2.
Aryl and
Alkyl SF3
Compounds
/ 219
7.7.3.
Dialkylaminosulfur Trifluorides
/ 219
7.7.4.
Hypervalent Sulfur Fluorides
/ 221
7.7.5.
Related Hypervalent Selenium and Tellurium
Fluorides
/ 221
7.7.6.
Organic Sulfinyl and Sulfonyl Fluorides
/ 222
7.8.
The Pentafluorosulfanyl (SF5) Group
/ 222
7.8.1.
Saturated Aliphatic Systems
/ 225
7.8.2.
Vinylic SF5 Substituents
/ 228
7.8.3.
Acetylenie SF5
Substituents
/ 229
7.8.4.
Aromatic SF5 Substituents
/ 229
7.9.
Bromine Trifluoride and Iodine Pentafluoride
/ 230
7.10.
Aryl Halogen Difluorides and Tetrafluorides
/ 231
7.11.
Xenon Difluoride
/ 231
References
/ 232
GENERAL INDEX
233
COMPOUND INDEX
236
|
| any_adam_object | 1 |
| author | Dolbier, William R. 1939- |
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| dewey-ones | 547 - Organic chemistry |
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| dewey-sort | 3547 12 |
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| id | DE-604.BV035810775 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T22:05:07Z |
| institution | BVB |
| isbn | 9780470193419 |
| language | English |
| lccn | 2008053434 |
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| physical | XIV, 256 S. graph. Darst. |
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| publisher | Wiley |
| record_format | marc |
| spelling | Dolbier, William R. 1939- Verfasser (DE-588)123552257 aut Guide to fluorine NMR for organic chemists William R. Dolbier Hoboken, NJ Wiley 2009 XIV, 256 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Includes index Fluorine compounds Spectra Nuclear magnetic resonance spectroscopy NMR-Spektroskopie (DE-588)4075421-2 gnd rswk-swf Fluorverbindungen (DE-588)4154876-0 gnd rswk-swf Fluorverbindungen (DE-588)4154876-0 s NMR-Spektroskopie (DE-588)4075421-2 s DE-604 Digitalisierung UB Bayreuth application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018669704&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Dolbier, William R. 1939- Guide to fluorine NMR for organic chemists Fluorine compounds Spectra Nuclear magnetic resonance spectroscopy NMR-Spektroskopie (DE-588)4075421-2 gnd Fluorverbindungen (DE-588)4154876-0 gnd |
| subject_GND | (DE-588)4075421-2 (DE-588)4154876-0 |
| title | Guide to fluorine NMR for organic chemists |
| title_auth | Guide to fluorine NMR for organic chemists |
| title_exact_search | Guide to fluorine NMR for organic chemists |
| title_full | Guide to fluorine NMR for organic chemists William R. Dolbier |
| title_fullStr | Guide to fluorine NMR for organic chemists William R. Dolbier |
| title_full_unstemmed | Guide to fluorine NMR for organic chemists William R. Dolbier |
| title_short | Guide to fluorine NMR for organic chemists |
| title_sort | guide to fluorine nmr for organic chemists |
| topic | Fluorine compounds Spectra Nuclear magnetic resonance spectroscopy NMR-Spektroskopie (DE-588)4075421-2 gnd Fluorverbindungen (DE-588)4154876-0 gnd |
| topic_facet | Fluorine compounds Spectra Nuclear magnetic resonance spectroscopy NMR-Spektroskopie Fluorverbindungen |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=018669704&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT dolbierwilliamr guidetofluorinenmrfororganicchemists |