Organic Structures From Spectra 5E
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Table of Contents

PREFACE vii
LIST OF TABLES xi


LIST OF FIGURES xiii


1 INTRODUCTION 1


1.1 GENERAL PRINCIPLES OF ABSORPTION SPECTROSCOPY 1


1.2 CHROMOPHORES 3


1.3 DEGREE OF UNSATURATION 3


1.4 CONNECTIVITY 4


1.5 SENSITIVITY 5


1.6 PRACTICAL CONSIDERATIONS 5


2 ULTRAVIOLET (UV) SPECTROSCOPY 7


2.1 BASIC INSTRUMENTATION 7


2.2 THE NATURE OF ULTRAVIOLET SPECTROSCOPY 8


2.3 QUANTITATIVE ASPECTS OF ULTRAVIOLET SPECTROSCOPY 8


2.4 CLASSIFICATION OF UV ABSORPTION BANDS 9


2.5 SPECIAL TERMS IN ULTRAVIOLET SPECTROSCOPY 10


2.6 IMPORTANT UV CHROMOPHORES 10


2.7 THE EFFECT OF SOLVENTS 14


3 INFRARED (IR) SPECTROSCOPY 15


3.1 ABSORPTION RANGE AND THE NATURE OF IR ABSORPTION 15


3.2 EXPERIMENTAL ASPECTS OF INFRARED SPECTROSCOPY 16


3.3 GENERAL FEATURES OF INFRARED SPECTRA 16


3.4 IMPORTANT IR CHROMOPHORES 17


4 MASS SPECTROMETRY 21


4.1 IONISATION PROCESSES 21


4.2 INSTRUMENTATION 23


4.3 MASS SPECTRAL DATA 24


4.4 REPRESENTATION OF FRAGMENTATION PROCESSES 29


4.5 FACTORS GOVERNING FRAGMENTATION PROCESSES 30


4.6 EXAMPLES OF COMMON TYPES OF FRAGMENTATION 30


5 NUCLEAR MAGNETIC RESONANCE (NMR) SPECTROSCOPY 34


5.1 THE PHYSICS OF NUCLEAR SPINS AND NMR INSTRUMENTS 34


5.2 CONTINUOUS WAVE (CW) NMR SPECTROSCOPY 39


5.3 FOURIER-TRANSFORM (FT) NMR SPECTROSCOPY 40


5.4 THE NUCLEAR OVERHAUSER EFFECT (NOE) 41


5.5 CHEMICAL SHIFT IN 1H NMR SPECTROSCOPY 42


5.6 SPIN-SPIN COUPLING IN 1H NMR SPECTROSCOPY 53


5.7 ANALYSIS OF 1H NMR SPECTRA 56


5.8 CHANGING THE MAGNETIC FIELD IN NMR SPECTROSCPY 58


5.9 RULES FOR SPECTRAL ANALYSIS OF FIRST ORDER SPECTRA 59


5.10 CORRELATION OF 1H ? 1H COUPLING CONSTANTS WITH
STRUCTURE 66


6 13C NMR SPECTROSCOPY 71


6.1 COUPLING AND DECOUPLING IN 13C NMR SPECTRA 71


6.2 DETERMINING 13C SIGNAL MULTIPLICITY USING DEPT 72


6.3 SHIELDING AND CHARACTERISTIC CHEMICAL SHIFTS IN 13C NMR
SPECTRA 75


7 2-DIMENSIONAL NMR SPECTROSCOPY 81


7.1 COSY (CORRELATION SPECTROSCOPY) 83


7.2 THE HSQC (HETERONUCLEAR SINGLE QUANTUM CORRELATION) OR HSC
(HETERONUCLEAR SHIFT


CORRELATION) SPECTRUM 84


7.3 HMBC (HETERONUCLEAR MULTIPLE BOND CORRELATION) 86


7.4 NOESY (NUCLEAR OVERHAUSER EFFECT SPECTROSCOPY) 91


7.5 TOCSY (TOTAL CORRELATION SPECTROSCOPY) 92


8 MISCELLANEOUS TOPICS 94


8.1 SOLVENTS FOR NMR SPECTROSCOPY 94


8.2 SOLVENT INDUCED SHIFTS 95


8.3 DYNAMIC PROCESSES IN NMR - THE NMR TIME-SCALE 96


8.4 THE EFFECT OF CHIRALITY 98


8.5 THE NMR SPECTRA OF "OTHER NUCLEI" 99


9 DETERMINING THE STRUCTURE OF ORGANIC COMPOUNDS FROM SPECTRA
100


9.1 SOLVING PROBLEMS 102


9.2 WORKED EXAMPLES 103


10 PROBLEMS 111


10.1 SPECTROSCOPIC IDENTIFICATION OF ORGANIC COMPOUNDS 111


10.2 THE ANALYSIS OF MIXTURES 397


10.3 PROBLEMS IN 2-DIMENSIONAL NMR 407


10.4 NMR SPECTRAL ANALYSIS 467


INDEX 493

About the Author

Professor Leslie D. Field, Professor of Chemistry, University of New South Wales, Australia, has built up an international reputation for his research on novel reagents containing coordinatively unsaturated transition metals and for his extensive work in the field of NMR spectroscopy including novel studies on heteronuclear coherence transfer and multiple quantum NMR. Field was Professor of Organic Chemistry at the University of Sydney 1990 to 2005 and Head of the School of Chemistry from 1997 to 2001. He has also been the Deputy Vice Chancellor (Research) at UNSW since April 2005.
Professor Sev Sternhel is Emeritus Professor of Chemistry (Organic), at University of Sydney, Australia. The author of approximately 200 scientific publications, he has chaired two panels of the Australian Research Council. Sternhel was Professor of Organic Chemistry from December 1977 until his retirement in 1999. His research interests are in organic chemistry and molecular engineering.
Dr John R. Kalman, Senior Lecturer, Department of Chemistry, University of Technology at Sydney, Australia has written articles for Journal of Forensic Sciences, Journal of Polymer Science and other journals.

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