Enhanced descriptions from Syndetics:

This text provides the graduate student with a systematic guide to unravelling structural information from the NMR spectra of unknown synthetic and natural compounds.

A brief introduction gives an overview of the basic principles and elementary instrumental methods of NMR. This is followed by instructional strategy and tactical advice on how to translate spectra into meaningful structural information. The book provides the student with 55 sets of spectra of graduated complexity. These are designed to challenge the student's problem-solving abilities by the introduction of new concepts with each group of problems, followed by possible solutions and full explanations. A formula index of solutions is provided at the end of the text.

This third edition, following on from the second (a reprint of the first edition with corrections), presents significant new material. Thus, actual methods of two-dimensional NMR such as some inverse techniques of heteronuclear shift correlation, as well as the detection of proton-proton connectivities and nuclear Overhauser effects are included. To demonstrate the applications of these methods, new problems have replaced those of previous editions.

Table of contents provided by Syndetics

• Preface (p. ix)
• Preface to the First Edition (p. x)
• Symbols and Abbreviations (p. xi)
• 1 Short Introduction to Basic Principles and Methods (p. 1)
• 1.1 Chemical shift (p. 1)
• 1.2 Spin-spin coupling and coupling constants (p. 1)
• 1.3 Signal multiplicity (multiplets) (p. 2)
• 1.4 Spectra of first and higher order (p. 3)
• 1.5 Chemical and magnetic equivalence (p. 4)
• 1.6 Fourier transform (FT) NMR spectra (p. 5)
• 1.7 Spin decoupling (p. 6)
• 1.8 Nuclear Overhauser effect (p. 8)
• 1.9 Relaxation, relaxation times (p. 10)
• 2 Recognition of Structural Fragments by NMR (p. 11)
• 2.1 Functional groups (p. 11)
• 2.1.2 [superscript 1]H Chemical Shifts (p. 11)
• 2.1.2 Deuterium exchange (p. 12)
• 2.1.3 [superscript 13]C Chemical shifts (p. 12)
• 2.1.4 [superscript 15]N Chemical shifts (p. 14)
• 2.2 Skeletal structure (atom connectivities) (p. 16)
• 2.2.1 HH Multiplicities (p. 16)
• 2.2.2 CH Multiplicities (p. 18)
• 2.2.3 HH Coupling constants (p. 21)
• 2.2.4 CH Coupling constants (p. 26)
• 2.2.5 NH Coupling constants (p. 29)
• 2.2.6 HH COSY (geminal, vicinal, w-relationships of protons) (p. 30)
• 2.2.7 CC INADEQUATE (CC bonds) (p. 33)
• 2.2.8 Two-dimensional carbon-proton shift correlation via one-bond CH coupling (p. 36)
• 2.2.9 Two-dimensional carbon-proton shift correlation via long-range CH coupling (p. 39)
• 2.3 Relative configuration and conformation (p. 42)
• 2.3.1 HH Coupling constants (p. 42)
• 2.3.2 CH Coupling constants (p. 46)
• 2.3.3 NH Coupling constants (p. 47)
• 2.3.4 [superscript 13]C Chemical shifts (p. 48)
• 2.3.5 NOE Difference spectra (p. 51)
• 2.3.6 HH NOESY and ROESY (p. 53)
• 2.4 Absolute configuration (p. 54)
• 2.4.1 Diastereotopism (p. 54)
• 2.4.2 Chiral shift reagents (ee determination) (p. 56)
• 2.5 Intra- and intermolecular interactions (p. 58)
• 2.5.1 Anisotropic effects (p. 58)
• 2.5.2 Ring current of aromatic compounds (p. 58)
• 2.5.3 Intra- and intermolecular hydrogen bonding (p. 59)
• 2.5.4 Protonation effects (p. 60)
• 2.6 Molecular dynamics (fluxionality) (p. 61)
• 2.6.2 [superscript 13]C Spin-lattice relaxation times (p. 63)
• 2.7 Summary (p. 67)
• 3 Problems (p. 69)
• 1-12 Application of one-dimensional [superscript 1]H NMR (p. 69)
• 13-14 Temperature dependent [superscript 1]H and [superscript 13]C NMR spectra (p. 83)
• 15-20 Application of one-dimensional [superscript 13]C NMR spectra (p. 85)
• 21-22 CC INADEQUATE experiments (p. 91)
• 23-29 Application of one-dimensional [superscript 1]H and [superscript 13]C NMR spectra (p. 93)
• 30-31 Application of one-dimensional [superscript 1]H, [superscript 13]C and [superscript 15]N NMR spectra (p. 100)
• 32-42 Combined application of one and two-dimensional [superscript 1]H and [superscript 13]C NMR experiments (p. 104)
• 43-55 Identification and structural elucidation of of natural products by one and two-dimensional [superscript 1]H and [superscript 13]C NMR (p. 128)
• 4 Solutions to Problems (p. 180)
• 1 Dimethyl cis-cyclopropane-1,2-dicarboxylate (p. 180)
• 2 Ethylacrylate (p. 180)
• 3 cis-1-Methoxybut-1-en-3-yne (p. 181)
• 4 trans-3-(N-Methylpyrrol-2-yl)propenal (p. 181)
• 5 1,9-Bis(pyrrol-2-yl)pyrromethene (p. 182)
• 6 3-Acetylpyridine (p. 182)
• 7 Anthracene-1,8-dialdehyde (p. 183)
• 8 trans-Stilbene-4-aldehyde (p. 184)
• 9 6,4'-Dimethoxyisoflavone (p. 185)
• 10 Catechol (3,5,7,3',4'-pentahydroxyflavane) (p. 185)
• 11 Methyloxirane and monordene (p. 187)
• 12 2-Methyl-6-(N,N-dimethylamino)-trans-4-nitro-trans-5-phenylcyclohexene (p. 188)
• 13 (E)-3-(N,N-Dimethylamino)acrolein (p. 189)
• 14 cis-1,2-Dimethylcyclohexane (p. 190)
• 15 5-Ethynyl-2-methylpyridine (p. 191)
• 16 5-Hydroxy-3-methyl-1H-pyrazole (p. 192)
• 17 o-Hydroxyacetophenone (p. 192)
• 18 Potassium 1-acetonyl-2,4,6-trinitrocyclohexa-2,5-dienate (p. 193)
• 19 trans-3-[4-(N,N-Dimethylamino)phenyl]-2-ethylpropenal (p. 194)
• 20 N-Butylsalicylaldimine (p. 194)
• 21 Benzo[b]furan (p. 195)
• 22 3-Hydroxypropyl 2-ethylcyclohexa-1,3-diene-5-carboxylate (p. 195)
• 23 Hex-3-yn-1-ol (p. 196)
• 24 N,N-Diethylamino)ethyl 4-aminobenzoate hydrochloride (procaine hydrochloride) (p. 197)
• 25 5,5'-Bis-(hydroxymethyl)-2,2'-bifuran (p. 198)
• 26 N-Methyl-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (p. 199)
• 27 Ethoxycarbonyl-4-(3-hydroxypropyl)-1-methylpyrrole (p. 200)
• 28 p-Tolylsulphonyl-5-propylpyridine (p. 202)
• 29 6-Methoxytetralin-1-one (p. 203)
• 30 Triazolo[1,5-a]pyrimidine (p. 205)
• 31 6-n-Butyltetrazolo[1,5-a]pyrimidine and 2-azido-5-n-butylpyrimidine (p. 205)
• 32 Hydroxyphthalide (p. 207)
• 33 Dicyclopentadiene (p. 207)
• 34 trans-1-Cyclopropyl-2-methylbuta-1,3-diene (p. 208)
• 35 cis-6-Hydroxy-1-methyl-4-isopropylcyclohexene (carveol) (p. 210)
• 36 trans-2-Methylcyclopentanol (p. 210)
• 37 trans-2-(2-Pyridyl)methylcyclohexanol (p. 211)
• 38 Nona-2-trans-6-cis-dienal (p. 212)
• 39 2,3-Diaza-7,8,12,13,17,18-hexaethylporphyrin (p. 213)
• 40 2-Hydroxy-3,4,3',4'-tetramethoxydeoxybenzoin (p. 214)
• 41 3',4',7,8-Tetramethoxyisoflavone (p. 216)
• 42 3',4',6,7-Tetramethoxy-3-phenylcoumarin (p. 217)
• 43 Aflatoxin B[subscript 1] (p. 218)
• 44 1,5-Dimethylcyclohexa-1,3-dien-5-ol-6-one, dimer (p. 220)
• 45 Asperuloside (p. 222)
• 46 Lacto-N-tetrose (p. 225)
• 47 9[beta]-Hydroxycostic acid (p. 226)
• 48 14-(Umbelliferon-7-O-yl)driman-3,8-diol (p. 229)
• 49 3,4,5-Trimethyl-5,6-dihydronaphtho[2,3-b]furan (p. 232)
• 50 Sendarwine (p. 234)
• 51 Panaxatriol (p. 237)
• 52 trans-N-Methyl-4-methoxyproline (p. 240)
• 53 Cocaine hydrochloride (p. 242)
• 54 Viridifloric acid 7-retronecine ester (heliospathulin) (p. 244)
• 55 Actinomycin-D (p. 246)
• References (p. 250)
• Formula index of solutions to problems (p. 252)
• Subject index (p. 255)

Reviews provided by Syndetics

CHOICE Review

NMR (nuclear magnetic resonance) spectroscopy is the most important technique for elucidation of structures of organic compounds. A variety of powerful NMR techniques have been developed over the last 15 years or so, and most good undergraduate institutions have the equipment necessary for implementing these techniques. After a nice but rather brief introductory theoretical section, Breitmaier offers 50 problems of increasing sophistication in which the reader is asked to either deduce the structure under consideration or to explain certain features of the spectrum. After all the problems have been presented, the solutions are found together with explanations of the answers. The problems are challenging but well chosen; anyone who has worked through the problems will come away with a strong grounding in the applications of NMR spectroscopy. The book, if supplemented by a more thorough theoretical work, could be a useful adjunct to a course on NMR techniques. Highly recommended for libraries at undegraduate institutions offering strong research opportunities in organic chemistry. Advanced undergraduate through faculty; pre-professional; professional. A. Fry; Wesleyan University