Interpretation of Organic Spectra

by Ning, Yong-Cheng; Ernst, Richard R.

• ISBN13: 9780470825167
• ISBN10: 0470825162
• Edition: 1st
• Format: Hardcover
• Copyright: 2011-03-08
• Publisher: Wiley

Summary

Although there are a number of books in this field, most of them lack an introduction of comprehensive analysis of MS and IR spectra, and others do not provide up-to-date information like tandem MS. This book fills the gap. The merit of this book is that the author will not only introduce knowledge for analyzing nuclear magnetic resonance spectra including 1 H spectra (Chapter 1), 13 C spectra (Chapter 2) and 2D NMR spectra (Chapter 3), he also arms readers systemically with knowledge of Mass spectra (including EI MS spectra and MS spectra by using soft ionizations) (Chapter 4) and IR spectra (Chapter 5). In each chapter the author presents very practical application skills by providing various challenging examples. The last chapter (Chapter 6) provides the strategy, skills and methods on how to identify an unknown compound through a combination of spectra. Based on nearly 40 years researching and teaching experience, the author also proposes some original and creative ideas, which are very practical for spectral interpretation.

Author Biography

Yong-Cheng Ning studied at the Engineering-Physics Department of Tsinghua University, Beijing, China where after his graduation he worked as a faculty member. From 1971 to 1978 he researched structural identification of organic compounds at the Institute of Chemical Engineering in Shenyang. Between 1981 and 1984 Yong-Chen Ning participated in research in NMR, MS, X-ray diffraction and alkaloid laboratories of the Institute of Chemistry of Natural Substances in Paris. Since 1993 he has been a full professor at the Tsinghua University. Yong-Chen Ning's books have won several awards, including the prize for excellent teaching materials, and are part of China's standard curriculum. His book Structural Identification of Organic Compounds and Organic Spectroscopy (Chinese) was awarded the second-class prize for 'Excellent Teaching Materials' in 1992 and 'Excellent Textbook for Graduate Students' in 2003 by the Ministry of Education of China.

Table of Contents

Foreword	p. ix
Preface	p. xi
Interpretation of 1H NMR spectra	p. 1
Chemical shift	p. 3
Conception of chemical shift	p. 3
Factors affecting chemical shifts	p. 3
Coupling constant J	p. 7
Coupling effect and coupling constant J	p. 7
Discussion of coupling constants according to their kinds	p. 8
Chemical equivalence and magnetic equivalence	p. 11
Chemical equivalence	p. 13
Magnetic equivalence	p. 17
Classification of 1H spectra	p. 18
Characteristics of the 1H spectra of some functional groups	p. 19
Substituted phenyl ring	p. 19
Substituted heteroaromatic ring	p. 21
Normal long-chain alkyl group	p. 21
Carbonyl compounds	p. 21
Reactive hydrogen atom	p. 22
Compounds containing fluorine or phosphor atoms	p. 23
Interpretation of 1H NMR spectra	p. 23
Find impurity peaks, pay attention to the solvent applied	p. 24
Calculation of the unsaturation number of the unknown compound	p. 24
Determination of the number of hydrogen atoms corresponding to every peak set in the 1H spectrum	p. 25
Determination of functional groups of the unknown compound	p. 26
Analysis of coupling splittings of peak sets	p. 26
Combination of possible structural units	p. 27
Assignment of the 1H spectrum according to the deduced structure	p. 28
Checking of the deduced structure	p. 28
Examples of 1H spectrum interpretation	p. 29
Reference	p. 38
Interpretation of 13C NMR spectra	p. 39
Characteristics and advantages of the 13C NMR spectra	p. 39
The main parameter of the 13 C spectrum is the chemical shift	p. 41
Chemical shift values of common functional groups and main factors affecting chemical shift values	p. 42
Alkanes and their derivatives	p. 43
Cycloalkanes and their derivatives	p. 45
Alkylenes and their derivatives	p. 45
Benzene and its derivatives	p. 46
Carbonyl groups	p. 47
Determination of the carbon atom orders	p. 47
Steps for 13C NMR spectrum interpretation	p. 48
Recognizing impurity peaks and identifying solvent peaks	p. 49
Calculation of the unsaturation number of the unknown compound	p. 50
Consideration of chemical shift values of peaks	p. 50
Determination of carbon atom orders	p. 51
Postulation of possible functional groups	p. 51
Interpretation of 2D NMR spectra	p. 53
General knowledge about 2D NMR spectra	p. 53
Homonuclear shift correlation spectroscopy, COSY (H, H-COSY)	p. 54
Heteronuclear shift correlation spectroscopy	p. 68
Long-range heteronuclear shift correlation spectroscopy	p. 75
NOESY and ROESY	p. 79
Total correlation spectroscopy, TOCSY	p. 84
References	p. 85
Interpretation of mass spectra	p. 87
Basic knowledge of organic mass spectrometry	p. 87
Mass spectra	p. 87
Ionization in organic mass spectrometry	p. 87
Ion types in organic mass spectrometry	p. 88
Isotopic ion clusters in mass spectra	p. 89
Interpretation of EI MS	p. 91
Determination of molecular ion peak	p. 91
Interpretation of fragment ion peaks	p. 93
Interpretation of rearrangement ion peaks	p. 98
Complex cleavages of alicyclic compounds	p. 100
Mass spectrum patterns of common functional groups	p. 102
Interpretation of the EI mass spectrum and examples	p. 107
Interpretation of the mass spectra from soft ionization	p. 115
Mass spectra from ESI (electrospray ionization)	p. 115
Mass spectra from CI	p. 117
Mass spectra from FAB	p. 118
Mass spectra from MALDI	p. 119
Mass spectra from APCI	p. 120
Examples of the interpretation of mass spectra from soft ionization	p. 120
Interpretation of high resolution mass spectra	p. 123
Interpretation of mass spectra from tandem mass spectrometry	p. 126
References	p. 127
Interpretation of infrared spectra	p. 129
Elementary knowledge of infrared spectroscopy	p. 129
Infrared spectrum	p. 129
Two regions of the infrared spectrum	p. 130
Characteristic absorption frequencies of functional groups	p. 130
Elemental equation of IR spectroscopy	p. 130
Factors affecting absorption frequencies	p. 130
Characteristic frequencies of common functional groups	p. 132
Discussion on the IR spectrum according to regions	p. 132
Functional group region	p. 133
Fingerprint region	p. 135
Interpretation of IR spectra according to regions	p. 135
Interpretation of IR spectra	p. 139
Key points for the interpretation of IR spectra	p. 139
Steps for the interpretation of an IR spectrum	p. 140
Searching standard IR spectra from IR spectrum collections or websites	p. 140
Examples of interpreting IR spectra	p. 141
Identification of unknown compounds or confirmation of structures through comprehensive interpretation of spectra	p. 147
Commonly used method and steps	p. 148
1H spectrum	p. 148
13C spectrum	p. 149
DEPT spectrum	p. 149
COSY spectrum	p. 149
HMQC (or HSQC) spectrum	p. 150
HMBC spectrum	p. 150
Examples for the deduction of the structure of an unknown compound or for the confirmation of an anticipated structure	p. 150
Reference	p. 408
List of abbreviations	p. 409
Index	p. 411
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