Interpretation of Organic Spectra

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 with Spectroscopic Techniques (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.

• Foreword ix Preface xi1 Interpretation of 1H NMR spectra 11.1 Chemical shift 31.1.1 Conception of chemical shift 31.1.2 Factors affecting chemical shifts 31.2 Coupling constant J 71.2.1 Coupling effect and coupling constant J 71.2.2 Discussion of coupling constants according to their kinds 81.3 Chemical equivalence and magnetic equivalence 111.3.1 Chemical equivalence 131.3.2 Magnetic equivalence 171.3.3 Classification of 1H spectra 181.4 Characteristics of the 1H spectra of some functional groups 191.4.1 Substituted phenyl ring 191.4.2 Substituted heteroaromatic ring 211.4.3 Normal long-chain alkyl group 211.4.4 Carbonyl compounds 211.4.5 Reactive hydrogen atom 221.4.6 Compounds containing fluorine or phosphor atoms 231.5 Interpretation of 1H NMR spectra 231.5.1 Find impurity peaks, pay attention to the solvent applied 241.5.2 Calculation of the unsaturation number of the unknown compound 241.5.3 Determination of the number of hydrogen atoms corresponding to every peak set in the 1H spectrum 251.5.4 Determination of functional groups of the unknown compound 261.5.5 Analysis of coupling splittings of peak sets 261.5.6 Combination of possible structural units 271.5.7 Assignment of the 1H spectrum according to the deduced structure 281.5.8 Checking of the deduced structure 281.6 Examples of 1H spectrum interpretation 29Reference 382 Interpretation of 13C NMR spectra 392.1 Characteristics and advantages of the 13C NMR spectra 392.2 The main parameter of the 13C spectrum is the chemical shift 412.3 Chemical shift values of common functional groups and main factors affecting chemical shift values 422.3.1 Alkanes and their derivatives 432.3.2 Cycloalkanes and their derivatives 452.3.3 Alkylenes and their derivatives 452.3.4 Benzene and its derivatives 462.3.5 Carbonyl groups 472.4 Determination of the carbon atom orders 472.5 Steps for 13C NMR spectrum interpretation 482.5.1 Recognizing impurity peaks and identifying solvent peaks 492.5.2 Calculation of the unsaturation number of the unknown compound 502.5.3 Consideration of chemical shift values of peaks 502.5.4 Determination of carbon atom orders 512.5.5 Postulation of possible functional groups 513 Interpretation of 2D NMR spectra 533.1 General knowledge about 2D NMR spectra 533.2 Homonuclear shift correlation spectroscopy, COSY (H, H-COSY) 543.3 Heteronuclear shift correlation spectroscopy 683.4 Long-range heteronuclear shift correlation spectroscopy 753.5 NOESY and ROESY 793.6 Total correlation spectroscopy, TOCSY 84References 854 Interpretation of mass spectra 874.1 Basic knowledge of organic mass spectrometry 874.1.1 Mass spectra 874.1.2 Ionization in organic mass spectrometry 874.1.3 Ion types in organic mass spectrometry 884.2 Isotopic ion clusters in mass spectra 894.3 Interpretation of EI MS 914.3.1 Determination of molecular ion peak 914.3.2 Interpretation of fragment ion peaks 934.3.3 Interpretation of rearrangement ion peaks 984.3.4 Complex cleavages of alicyclic compounds 1004.3.5 Mass spectrum patterns of common functional groups 1024.3.6 Interpretation of the EI mass spectrum and examples 1074.4 Interpretation of the mass spectra from soft ionization 1154.4.1 Mass spectra from ESI (electrospray ionization) 1154.4.2 Mass spectra from CI 1174.4.3 Mass spectra from FAB 1184.4.4 Mass spectra from MALDI 1194.4.5 Mass spectra from APCI 1204.4.6 Examples of the interpretation of mass spectra from soft ionization 1204.5 Interpretation of high resolution mass spectra 1234.6 Interpretation of mass spectra from tandem mass spectrometry 126References 1275 Interpretation of infrared spectra 1295.1 Elementary knowledge of infrared spectroscopy 1295.1.1 Infrared spectrum 1295.1.2 Two regions of the infrared spectrum 1305.2 Characteristic absorption frequencies of functional groups 1305.2.1 Elemental equation of IR spectroscopy 1305.2.2 Factors affecting absorption frequencies 1305.2.3 Characteristic frequencies of common functional groups 1325.3 Discussion on the IR spectrum according to regions 1325.3.1 Functional group region 1335.3.2 Fingerprint region 1355.4 Interpretation of IR spectra according to regions 1355.5 Interpretation of IR spectra 1395.5.1 Key points for the interpretation of IR spectra 1395.5.2 Steps for the interpretation of an IR spectrum 1405.5.3 Searching standard IR spectra from IR spectrum collections or websites 1405.5.4 Examples of interpreting IR spectra 1416 Identification of unknown compounds or confirmation of structures through comprehensive interpretation of spectra 1476.1 Commonly used method and steps 1486.1.1 1H spectrum 1486.1.2 13C spectrum 1496.1.3 DEPT spectrum 1496.1.4 COSY spectrum 1496.1.5 HMQC (or HSQC) spectrum 1506.1.6 HMBC spectrum 1506.2 Examples for the deduction of the structure of an unknown compound or for the confirmation of an anticipated structure 150Reference 408List of abbreviations 409Index 411

“I thoroughly recommend Interpretation of Organic Spectra to you.”  (Appl. Organometal. Chem, 1 October 2013)