Structure Elusidation by NMR in Organic Chemistry, изд. 3

Автор(ы):Breitmaier E.
06.10.2007
Год изд.:2002
Издание:3
Описание: This book, based on many lectures and seminars, attempts to provide advanced undergraduates and graduate students with a systematic, readable and inexpensive introduction to the methods of structure determination by NMR. Chapter 1 starts with a deliberately concise survey of the basic terms, parameters and techniques dealt with in detail in other books, which cover the basic principles of NMR, pulse sequences as well as theoretical aspects of chemical shifts and spin-spin coupling, and which this workbook is not intended to replace. An introduction to basic strategies and tactics of structure determination using one- and two-dimensional NMR methods then follows in Chapter 2. Chapter 3 presents a series of case studies, providing spectroscopic details of 55 compounds that illustrate typical applications of NMR techniques in the structural characterisation of both synthetic and natural products. One can work independently, solve the problem from the spectra and check the result in the formula index, or follow the detailed solutions given in Chapter 4.
Оглавление:
Structure Elusidation by NMR in Organic Chemistry — обложка книги. Обложка книги.
1 SHORT INTRODUCTION TO BASIC PRINCIPLES AND METHODS [1]
  1.1 Chemical shift [1]
  1.2 Spin-spin coupling and coupling constants [1]
  1.3 Signal multiplicity (multiplets) [2]
  1.4 Spectra of first and higher order [3]
  1.5 Chemical and magnetic equivalence [4]
  1.6 Fourier transform (FT) NMR spectra [5]
  1.7 Spin decoupling [6]
  1.8 Nuclear Overhauser effect [8]
  1.9 Relaxation, relaxation times [10]
2 RECOGNITION OF STRUCTURAL FRAGMENTS BY NMR [11]
  2.1 Functional groups [11]
    2.1.2 (?)H Chemical Shifts [11]
    2.1.2 Deuterium exchange [12]
    2.1.3 (?)C Chemical shifts [12]
    2.1.4 (?)N Chemical shifts [14]
  2.2 Skeletal structure (atom connectivities) [16]
    2.2.1 HH Multiplicities [16]
    2.2.2 CH Multiplicities [18]
    2.2.3 HH Coupling constants [21]
    2.2.4 CH Coupling constants [26]
    2.2.5 NH Coupling constants [29]
    2.2.6 HH COSY (geminal, vicinal, (?)-relationships of protons) [30]
    2.2.7 CC INADEQUATE (CC bonds) [33]
    2.2.8 Two-dimensional carbon-proton shift correlation via one-bond CH coupling [36]
    2.2.9 Two-dimensional carbon-proton shift correlation via long-range CH coupling [39]
  2.3 Relative configuration and conformation [42]
    2.3.1 HH Coupling constants [42]
    2.3.2 CH Coupling constants [46]
    2.3.3 NH Coupling constants [47]
    2.3.4 (?)C Chemical shifts [48]
    2.3.5 NOE Difference spectra [51]
    2.3.6 HH NOESY and ROESY [53]
  2.4 Absolute configuration [54]
    2.4.1 Diastereotopism [54]
    2.4.2 Chiral shift reagents (ее determination) [56]
  2.5 Intra- and intermolecular interactions [58]
    2.5.1 Anisotropic effects [58]
    2.5.2 Ring current of aromatic compounds [58]
    2.5.3 Intra- and intermolecular hydrogen bonding [59]
    2.5.4 Protonation effects [60]
  2.6 Molecular dynamics (fluxionality) [61]
    2.6.2 (?)C Spin-lattice relaxation times [63]
  2.7 Summary [67]
3 PROBLEMS [69]
  1-12 Application of one-dimensional (?)H NMR [69]
  13-14 Temperature dependent (?)H and (?)C NMR spectra [83]
  15-20 Application of one-dimensional (?)C NMR spectra [85]
  21-22 CC INADEQUATE experiments [91]
  23-29 Application of one-dimensional (?)H and (?)C NMR spectra [93]
  30-31 Application of one-dimensional (?)H, (?)C and (?)N NMR spectra [100]
  32-42 Combined application of one and two-dimensional (?)H and (?)C NMR experiments [104]
  43-55 Identification and structural elucidation of of natural products by one and two-dimensional (?)H and (?)C NMR [128]
4 SOLUTIONS TO PROBLEMS [180]
  1 Dimethyl cis-cyclopropane-1,2-dicarboxylate [180]
  2 Ethylacrylate [180]
  3 cis-1-Methoxybut-1-en-3-yne [181]
  4 trans-3-((?)-Methylpyrrol-2-yl)propenal [181]
  5 1,9-Bis(pyrrol-2-yl)pyrromethene [182]
  6 3-Acetylpyridine [182]
  7 Anthracene-1,8-dialdehyde [183]
  8 trans-Stilbene-4-aldehyde [184]
  9 6,4'-Dimethoxyisoflavone [185]
  10 Catechol(3,5,7,3',4'-pentahydroxyflavane) [185]
  11 Methyloxirane and monordene [187]
  12 2-Methyl-6-(N,N-dimethylamino)-trans-4-nitro-trans-5-phenylcyclohexene [188]
  13 (E)-3-(N,N-Dimethylamino)acrolein [189]
  14 cis-1,2-Dimethylcyclohexane [190]
  15 5-Ethynyl-2-methylpyridine [191]
  16 5-Hydroxy-3-methyl-1H-pyrazole [192]
  17 o-Hydroxyacetophenone [192]
  18 Potassium 1-acetonyl-2,4,6-trinitrocyclohexa-2,5-dienate [193]
  19 trans-3-[4-(N,N-Dimethylamino)phenyl]-2-ethylpropenal [194]
  20 N-Butylsalicylaldimine [194]
  21 Benzo[b]furan [195]
  22 3-Hydroxypropyl 2-ethylcyclohexa-1,3-diene-5-carboxylate [195]
  23 Нех-З-уn-1-ol [196]
  24 N,N-Diethylamino)ethyl 4-aminobenzoate hydrochloride (procaine hydrochloride) [197]
  25 5,5'-Bis-(hydroxymethyl)-2,2'-bifuran [198]
  26 N-Methyl-6,7-methylenedioxy-1-oxo-1,2,3,4-tetrahydroisoquinoline [199]
  27 Ethoxycarbonyl-4-(3-hydroxypropyl)-1-methylpyrrole [200]
  28 p-Tolylsulphonyl-5-propylpyridine [202]
  29 6-Methoxytetralin-1-one [203]
  30 Triazolo[1,5-a]pyrimidine [205]
  31 6-n-Butyltetrazolo[1,5-a]pyrimidine and 2-azido-5-n-butylpyrimidine [205]
  32 Hydroxyphthalide [207]
  33 Dicyclopentadiene [207]
  34 trans-1-Cyclopropyl-2-methylbuta-1,3-diene [208]
  35 cis-6-Hydroxy-1-methyl-4-isopropylcyclohexene (carveol) [210]
  36 trans-2-Methylcyclopentanol [210]
  37 trans-2-(2-Pyridyl)methylcyclohexanol [211]
  38 Nona-2-trans-6-cis-dienal [212]
  39 2,3-Diaza-7,8,12,13,17,18-hexaethylporphyrin [213]
  40 2-Hydroxy-3,4,3',4'-tetramethoxydeoxybenzoin [214]
  41 3',4',7,8-Tetramethoxyisoflavone [216]
  42 3',4',6,7-Tetramethoxy-3-phenylcoumarin [217]
  43 Aflatoxin B(?) [218]
  44 1,5-Dimethylcyclohexa-1,3-dien-5-ol-6-one, dimer [220]
  45 Asperuloside [222]
  46 Lacto-N-tetrose [225]
  47 9(?)-Hydroxycostic acid [226]
  48 14-(Umbelliferon-7-0-yl)driman-3,8-diol [229]
  49 3,4,5-Trimethyl-5,6-dihydronaphtho[2,3-b]furan [232]
  50 Sendarwine [234]
  51 Panaxatriol [237]
  52 trans-N-Methyl-4-methoxyproline [240]
  53 Cocaine hydrochloride [242]
  54 Viridifloric acid 7-retronecine ester (heliospathulin) [244]
  55 Actinomycin-D [246]
REFERENCES [250]
Formula index of solutions to problems [252]
Subject index [255]
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