Structure Determination of Organic Compounds

by Pretsch, Erno; Buhlmann, Philippe; Badertscher, Martin

• ISBN13: 9783540938095
• ISBN10: 3540938095
• Edition: 4th
• Format: Paperback
• Copyright: 2009-05-01
• Publisher: Springer Nature

Summary

This fourth edition of the highly successful and concise textbook contains about 20 % new data. Now included are chapters on 19F and 31P NMR as well as references to important Raman bands. With their unique approach of presenting - in the form of texts, tables, charts, and graphs - a succinct compilation of essential reference data for the interpretation of NMR, IR, UV/Vis, and mass spectra, the authors also provide a hands-on guide for interpreting experimental spectral data and elucidating the structure of the respective compounds behind them.Besides spectra of common solvents, calibration reagents, and MALDI and FAB MS matrix materials, fragmentation rules for mass spectrometry and UV/Vis spectra of representative compounds are included. The book will benefit students during courses and exercises, and advanced learners may use it to supplement their understanding of extended textbooks on the topic. While only a basic knowledge of spectroscopic techniques is required to use this book, it will serve as a data reference for specialists in the field and will support practitioners routinely faced with the task of interpreting spectral information.From a review of the previous edition:"Practically all teachers in spectroscopy and countless students know these books and work continuously with them." (Magnetic Resonance in Chemistry, 2002, Vol. 40, Issue 3, p. 247)

Table of Contents

Introduction	p. 1
Scope and Organization	p. 1
Abbreviations and Symbols	p. 3
Summary Tables	p. 5
General Tables	p. 5
Calculation of the Number of Double Bond Equivalents from the Molecular Formula	p. 5
Properties of Selected Nuclei	p. 6
13C NMR Spectroscopy	p. 7
1H NMR Spectroscopy	p. 10
IR Spectroscopy	p. 13
Mass Spectrometry	p. 18
Average Masses of Naturally Occurring Elements with Masses and Representative Relative Abundances of Isotopes	p. 18
Ranges of Natural Isotope Abundances of Selected Elements	p. 25
Isotope Patterns of Naturally Occurring Elements	p. 26
Calculation of Isotope Distributions	p. 27
Isotopic Abundances of Various Combinations of Chlorine, Bromine, Sulfur, and Silicon	p. 29
Isotope Patterns of Combinations of Cl and Br	p. 31
Indicators of the Presence of Heteroatoms	p. 32
Rules for Determining the Relative Molecular Weight (Mr)	p. 34
Homologous Mass Series as Indications of Structural Type	p. 35
Mass Correlation Table	p. 37
References	p. 45
UV/Vis Spectroscopy	p. 46
Combination Tables	p. 49
Alkanes, Cycloalkanes	p. 49
Alkenes, Cycloalkenes	p. 50
Alkynes	p. 51
Aromatic Hydrocarbons	p. 52
Heteroaromatic Compounds	p. 53
Halogen Compounds	p. 54
Oxygen Compounds	p. 56
Alcohols and Phenols	p. 56
Ethers	p. 57
Nitrogen Compounds	p. 59
Amines	p. 59
Nitro Compounds	p. 60
Thiols and Sulfides	p. 61
Carbonyl Compounds	p. 62
Aldehydes	p. 62
Ketones	p. 63
Carboxylic Acids	p. 64
Esters and Lactones	p. 65
Amides and Lactams	p. 67
13C NMR Spectroscopy	p. 69
Alkanes	p. 69
Chemical Shifts	p. 69
Coupling Constants	p. 78
References	p. 79
Alkenes	p. 80
Chemical Shifts	p. 80
Coupling Constants	p. 84
References	p. 84
Alkynes	p. 85
Chemical Shifts	p. 85
Coupling Constants	p. 85
References	p. 86
Alicyclics	p. 87
Chemical Shifts	p. 87
Coupling Constants	p. 92
Aromatic Hydrocarbons	p. 93
Chemical Shifts	p. 93
Coupling Constants	p. 100
References	p. 100
Heteroaromatic Compounds	p. 101
Chemical Shifts	p. 101
Coupling Constants	p. 108
Halogen Compounds	p. 109
Fluoro Compounds	p. 109
Chloro Compounds	p. 111
Bromo Compounds	p. 112
Iodo Compounds	p. 113
References	p. 113
Alcohols, Ethers, and Related Compounds	p. 114
Alcohols	p. 114
Ethers	p. 115
Nitrogen Compounds	p. 117
Amines	p. 117
Nitro and Nitroso Compounds	p. 119
Nitrosamines and Nitramines	p. 120
Azo and Azoxy Compounds	p. 120
Imines and Oximes	p. 120
Hydrazones and Carbodiimides	p. 121
Nitriles and Isonitriles	p. 122
Isocyanates, Thiocyanates, and Isothiocyanates	p. 122
Sulfur Compounds	p. 123
Thiols	p. 123
Sulfides	p. 123
Disulfides and Sulfonium Salts	p. 124
Sulfoxides and Sulfones	p. 125
Sulfonic and Sulfinic Acids and Derivatives	p. 126
Sulfurous and Sulfuric Acid Derivatives	p. 126
Sulfur-Containing Carbonyl Derivatives	p. 127
Carbonyl Compounds	p. 128
Aldehydes	p. 128
Ketones	p. 129
Carboxylic Acids	p. 131
Esters and Lactones	p. 133
Amides and Lactams	p. 135
Miscellaneous Carbonyl Derivatives	p. 137
Miscellaneous Compounds	p. 139
Compounds with Group IV Elements	p. 139
Phosphorus Compounds	p. 140
Miscellaneous Organometallic Compounds	p. 142
Natural Products	p. 144
Amino Acids	p. 144
Carbohydrates	p. 148
Nucleotides and Nucleosides	p. 150
Steroids	p. 152
Spectra of Solvents and Reference Compounds	p. 153
13C NMR Spectra of Common Deuterated Solvents	p. 153
13C NMR Spectra of Secondary Reference Compounds	p. 155
13C NMR Spectrum of a Mixture of Common Nondeuterated Solvents	p. 156
1H NMR Spectroscopy	p. 157
Alkanes	p. 157
Chemical Shifts	p. 157
Coupling Constants	p. 162
Alkenes	p. 164
Substituted Ethylenes	p. 164
Conjugated Dienes	p. 170
Allenes	p. 171
Alkynes	p. 172
Alicyclics	p. 173
Aromatic Hydrocarbons	p. 177
Heteroaromatic Compounds	p. 184
Non-Condensed Heteroaromatic Rings	p. 184
Condensed Heteroaromatic Rings	p. 191
Halogen Compounds	p. 196
Fluoro Compounds	p. 196
Chloro Compounds	p. 197
Bromo Compounds	p. 198
Iodo Compounds	p. 199
Alcohols, Ethers, and Related Compounds	p. 200
Alcohols	p. 200
Ethers	p. 202
Nitrogen Compounds	p. 205
Amines	p. 205
Nitro and Nitroso Compounds	p. 207
Nitrites and Nitrates	p. 208
Nitrosamines, Azo and Azoxy Compounds	p. 208
Imines, Oximes, Hydrazones, and Azines	p. 209
Nitriles and Isonitriles	p. 210
Cyanates, Isocyanates, Thiocyanates, and Isothiocyanates	p. 211
Sulfur Compounds	p. 212
Thiols	p. 212
Sulfides	p. 213
Disulfides and Sulfonium Salts	p. 214
Sulfoxides and Sulfones	p. 214
Sulfonic, Sulfurous, and Sulfuric Acids and Derivatives	p. 215
Thiocarboxylate Derivatives	p. 215
Carbonyl Compounds	p. 216
Aldehydes	p. 216
Ketones	p. 217
Carboxylic Acids and Carboxylates	p. 218
Esters and Lactones	p. 219
Amides and Lactams	p. 220
Miscellaneous Carbonyl Derivatives	p. 224
Miscellaneous Compounds	p. 226
Compounds with Group IV Elements	p. 226
Phosphorus Compounds	p. 227
Miscellaneous Compounds	p. 230
References	p. 231
Natural Products	p. 232
Amino Acids	p. 232
Carbohydrates	p. 235
Nucleotides and Nucleosides	p. 237
Spectra of Solvents and Reference Compounds	p. 239
1H NMR Spectra of Common Deuterated Solvents	p. 239
1H NMR Spectra of Secondary Reference Compounds	p. 241
1H NMR Spectrum of a Mixture of Common Nondeuterated Solvents	p. 242
Heteronuclear NMR Spectroscopy	p. 243
19F NMR Spectroscopy	p. 243
19F Chemical Shifts of Perfluoroalkanes	p. 243
Estimation of 19F Chemical Shifts of Substituted Fluoroethylenes	p. 247
Coupling Constants in Fluorinated Alkanes and Alkenes	p. 248
19F Chemical Shifts of Allenes and Alkynes	p. 249
19F Chemical Shifts and Coupling Constants of Fluorinated Alicyclics	p. 250
19F Chemical Shifts and Coupling Constants of Aromatics and Heteroaromatics	p. 251
19F Chemical Shifts of Alcohols and Ethers	p. 254
19F Chemical Shifts of Fluorinated Amine, Imine, and Hydroxylamine Derivatives	p. 255
19F Chemical Shifts of Sulfur Compounds	p. 256
19F Chemical Shifts of Carbonyl and Thiocarbonyl Compounds	p. 257
19F Chemical Shifts of Fluorinated Boron, Phosphorus, and Silicon Compounds	p. 258
19F Chemical Shifts of Natural Product Analogues	p. 259
References	p. 260
31P NMR Spectroscopy	p. 261
31P Chemical Shifts of Tricoordinated Phosphorus, PR1R2R3	p. 261
31P Chemical Shifts of Tetracoordinated Phosphonium Compounds	p. 262
31P Chemical Shifts of Compounds with a P=C or P=N Bond	p. 263
31P Chemical Shifts of Tetracoordinated P(=O) and P(=S) Compounds	p. 264
31P Chemical Shifts of Penta- and Hexacoordinated Phosphorus Compounds	p. 266
31P Chemical Shifts of Natural Phosphorus Compounds	p. 267
IR Spectroscopy	p. 269
Alkanes	p. 269
Alkenes	p. 272
Monoenes	p. 272
Allenes	p. 275
Alkynes	p. 276
Alicyclics	p. 277
Aromatic Hydrocarbons	p. 279
Heteroaromatic Compounds	p. 282
Halogen Compounds	p. 284
Fluoro Compounds	p. 284
Chloro Compounds	p. 285
Bromo Compounds	p. 286
Iodo Compounds	p. 286
Alcohols, Ethers, and Related Compounds	p. 287
Alcohols and Phenols	p. 287
Ethers, Acetals, and Ketals	p. 288
Epoxides	p. 290
Peroxides and Hydroperoxides	p. 291
Nitrogen Compounds	p. 292
Amines and Related Compounds	p. 292
Nitro and Nitroso Compounds	p. 294
Imines and Oximes	p. 296
Azo, Azoxy, and Azothio Compounds	p. 298
Nitriles and Isonitriles	p. 299
Diazo Compounds	p. 300
Cyanates and Isocyanates	p. 301
Thiocyanates and Isothiocyanates	p. 302
Sulfur Compounds	p. 304
Thiols and Sulfides	p. 304
Sulfoxides and Sulfones	p. 305
Thiocarbonyl Derivatives	p. 307
Thiocarbonic Acid Derivatives	p. 307
Carbonyl Compounds	p. 310
Aldehydes	p. 310
Ketones	p. 311
Carboxylic Acids	p. 314
Esters and Lactones	p. 316
Amides and Lactams	p. 319
Acid Anhydrides	p. 322
Acid Halides	p. 323
Carbonic Acid Derivatives	p. 324
Miscellaneous Compounds	p. 327
Silicon Compounds	p. 327
Phosphorus Compounds	p. 328
Boron Compounds	p. 331
Amino Acids	p. 332
Solvents, Suspension Media, and Interferences	p. 333
Infrared Spectra of Common Solvents	p. 333
Infrared Spectra of Suspension Media	p. 334
Interferences in Infrared Spectra	p. 335
Mass Spectrometry	p. 337
Alkanes	p. 337
Alkenes	p. 339
Alkynes	p. 341
Alicyclics	p. 342
Aromatic Hydrocarbons	p. 345
Heteroaromatic Compounds	p. 347
Halogen Compounds	p. 352
Alcohols, Ethers, and Related Compounds	p. 354
Alcohols and Phenols	p. 354
Hydroperoxides	p. 356
Ethers	p. 356
Aliphatic Epoxides	p. 359
Aliphatic Peroxides	p. 360
References	p. 361
Nitrogen Compounds	p. 362
Amines	p. 362
Nitro Compounds	p. 364
Diazo Compounds and Azobenzenes	p. 364
Azides	p. 365
Nitriles and Isonitriles	p. 366
Cyanates, Isocyanates, Thiocyanates, and Isothiocyanates	p. 367
References	p. 369
Sulfur Compounds	p. 371
Thiols	p. 371
Sulfides and Disulfides	p. 371
Sulfoxides and Sulfones	p. 373
Sulfonic Acids and Their Esters and Amides	p. 376
Thiocarboxylic Acid Esters	p. 377
References	p. 378
Carbonyl Compounds	p. 379
Aldehydes	p. 379
Ketones	p. 380
Carboxylic Acids	p. 381
Carboxylic Acid Anhydrides	p. 382
Esters and Lactones	p. 382
Amides and Lactams	p. 384
Imides	p. 386
References	p. 387
Miscellaneous Compounds	p. 388
Trialkylsilyl Ethers	p. 388
Phosphorus Compounds	p. 388
References	p. 389
Mass Spectra of Common Solvents and Matrix Compounds	p. 390
Electron Impact Ionization Mass Spectra of Common Solvents	p. 390
Spectra of Common FAB MS Matrix and Calibration Compounds	p. 393
Spectra of Common MALDI MS Matrix Compounds	p. 398
References	p. 400
UV/Vis Spectroscopy	p. 401
Correlation between Wavelength of Absorbed Radiation and Observed Color	p. 401
Simple Chromophores	p. 401
Conjugated Alkenes	p. 403
Dienes and Polyenes	p. 403
¿,ß-Unsaturated Carbonyl Compounds	p. 404
Aromatic Hydrocarbons	p. 406
Monosubstituted Benzenes	p. 406
Polysubstituted Benzenes	p. 407
Aromatic Carbonyl Compounds	p. 408
Reference Spectra	p. 409
Alkenes and Alkynes	p. 409
Aromatic Compounds	p. 410
Heteroaromatic Compounds	p. 415
Miscellaneous Compounds	p. 417
Nucleotides	p. 419
Common Solvents	p. 420
Subject Index	p. 421
Table of Contents provided by Ingram. All Rights Reserved.