Оглавление
H. L. Li. Organic Structures from Spectra
Table of Contents
List of Tables
List of Illustrations
Guide
Pages
Organic Structures from Spectra
PREFACE
LIST OF TABLES
LIST OF FIGURES
1 INTRODUCTION. 1.1 GENERAL PRINCIPLES OF ABSORPTION SPECTROSCOPY
1.2 CHROMOPHORES
1.3 DEGREE OF UNSATURATION
1.4 CONNECTIVITY
1.5 SENSITIVITY
1.6 PRACTICAL CONSIDERATIONS
2 ULTRAVIOLET (UV) SPECTROSCOPY. 2.1 THE NATURE OF ULTRAVIOLET SPECTROSCOPY
2.2 BASIC INSTRUMENTATION
2.3 QUANTITATIVE ASPECTS OF ULTRAVIOLET SPECTROSCOPY
2.4 CLASSIFICATION OF UV ABSORPTION BANDS
2.5 SPECIAL TERMS IN UV SPECTROSCOPY
2.6 IMPORTANT UV CHROMOPHORES
2.6.1 DIENES AND POLYENES
2.6.2 CARBONYL COMPOUNDS
2.6.3 BENZENE DERIVATIVES
2.7 THE EFFECT OF SOLVENTS
3 INFRARED (IR) SPECTROSCOPY. 3.1 ABSORPTION RANGE AND THE NATURE OF IR ABSORPTION
3.2 EXPERIMENTAL ASPECTS OF INFRARED SPECTROSCOPY
3.3 GENERAL FEATURES OF INFRARED SPECTRA
3.4 IMPORTANT IR CHROMOPHORES. 3.4.1 –O–H AND –N–H STRETCHING VIBRATIONS
3.4.2 C–H STRETCHING VIBRATIONS
3.4.3 –C≡N AND –C≡C– STRETCHING VIBRATIONS
3.4.4 CARBONYL GROUPS
3.4.5 OTHER POLAR FUNCTIONAL GROUPS
3.4.6 THE FINGERPRINT REGION
4 MASS SPECTROMETRY
4.1 IONISATION PROCESSES
4.2 INSTRUMENTATION
4.3 MASS SPECTRAL DATA
4.3.1 HIGH RESOLUTION MASS SPECTRA
4.3.2 MOLECULAR FRAGMENTATION
4.3.3 ISOTOPE RATIOS
4.3.4 CHROMATOGRAPHY COUPLED WITH MASS SPECTROMETRY
4.3.5 METASTABLE PEAKS
4.4 REPRESENTATION OF FRAGMENTATION PROCESSES
4.5 FACTORS GOVERNING FRAGMENTATION PROCESSES
4.6 EXAMPLES OF COMMON TYPES OF FRAGMENTATION
4.6.1 CLEAVAGE AT BRANCH POINTS
4.6.2 β–CLEAVAGE
4.6.3 CLEAVAGE TO CARBONYL GROUPS
4.6.4 CLEAVAGE α TO HETEROATOMS
4.6.5 RETRO DIELS–ALDER REACTION
4.6.6 THE McLAFFERTY REARRANGEMENT
5 1H NUCLEAR MAGNETIC RESONANCE (NMR) SPECTROSCOPY
5.1 THE PHYSICS OF NUCLEAR SPINS AND NMR INSTRUMENTS. 5.1.1 THE LARMOR EQUATION AND NUCLEAR MAGNETIC RESONANCE
5.2 BASIC NMR INSTRUMENTATION AND THE NMR EXPERIMENT
5.2.1 CONTINUOUS WAVE AND PULSED NMR SPECTROMETERS
5.2.2 NUCLEAR RELAXATION
5.2.3 MAGNETS FOR NMR SPECTROSCOPY
5.2.4 THE NMR SPECTRUM
5.3 CHEMICAL SHIFTS IN 1H NMR SPECTROSCOPY
5.4 SPIN–SPIN COUPLING IN 1H NMR SPECTROSCOPY
5.4.1 SIGNAL MULTIPLICITY – THE N+1 RULE
5.5 ANALYSIS OF 1H NMR SPECTRA
5.5.1 SPIN SYSTEMS
5.5.2 STRONGLY AND WEAKLY COUPLED SPIN SYSTEMS
5.5.3 MAGNETIC EQUIVALENCE
5.5.4 CONVENTIONS FOR NAMING SPIN SYSTEMS
5.5.5 SPECTRAL ANALYSIS OF FIRST-ORDER NMR SPECTRA
5.5.6 SPLITTING DIAGRAMS
Coincidentally Equivalent Coupling Constants
5.5.7 SPIN DECOUPLING
5.6 CORRELATION OF 1H–1H COUPLING WITH STRUCTURE
5.6.1 NON-AROMATIC SPIN SYSTEMS
5.6.2 AROMATIC SPIN SYSTEMS
para-Disubstituted Benzenes
5.7 THE NUCLEAR OVERHAUSER EFFECT (NOE) IN 1H NMR SPECTROSCOPY
5.8 LABILE AND EXCHANGEABLE PROTONS
REFERENCES
6 13C NMR SPECTROSCOPY
6.1 COUPLING AND DECOUPLING IN 13C NMR SPECTRA
6.2 THE NUCLEAR OVERHAUSER EFFECT (NOE) IN 13C NMR SPECTROSCOPY
6.3 DETERMINING 13C SIGNAL MULTIPLICITY USING DEPT
6.4 SHIELDING AND CHARACTERISTIC CHEMICAL SHIFTS IN 13C NMR SPECTRA
7 2-DIMENSIONAL NMR SPECTROSCOPY
7.1 PROTON–PROTON INTERACTIONS BY 2D NMR
7.1.1 COSY (CORRELATION SPECTROSCOPY)
7.1.2 TOCSY (TOTAL CORRELATION SPECTROSCOPY)
7.1.3 NOESY (NUCLEAR OVERHAUSER EFFECT SPECTROSCOPY)
7.2 PROTON–CARBON INTERACTIONS BY 2D NMR. 7.2.1 HETERONUCLEAR SINGLE BOND CORRELATION: THE HSQC (HETERONUCLEAR SINGLE QUANTUM CORRELATION) OR HSC (HETERONUCLEAR SHIFT CORRELATION) SPECTRUM
7.2.2 HMBC (HETERONUCLEAR MULTIPLE BOND CORRELATION)
8 MISCELLANEOUS TOPICS. 8.1 SOLVENTS FOR NMR SPECTROSCOPY
8.2 SOLVENT-INDUCED SHIFTS
8.3 DYNAMIC NMR SPECTROSCOPY – THE NMR TIME-SCALE
8.3.1 CONFORMATIONAL EXCHANGE PROCESSES
8.3.2 INTERMOLECULAR EXCHANGE OF LABILE PROTONS
8.3.3 ROTATION ABOUT PARTIAL DOUBLE BONDS
8.4 THE EFFECT OF CHIRALITY
8.5 THE NMR SPECTRA OF “OTHER NUCLEI”
9 DETERMINING THE STRUCTURE OF ORGANIC COMPOUNDS FROM SPECTRA
Collection of Spectra
9.1 SOLVING PROBLEMS
9.2 WORKED EXAMPLES
PROBLEM 117 (1) Perform all Routine Operations
(2) Identify any Structural Elements
(3) Assemble the Structural Elements
(4) Check that the answer is consistent with all spectra
PROBLEM 146 (1) Perform all Routine Operations
(2) Identify the Structural Elements
(3) Assemble the Structural Elements
PROBLEM 77 (1) Perform all Routine Operations
(2) Identify any Structural Elements
(3) Assemble the Structural Elements
(4) Check that the answer is consistent with all spectra
10 PROBLEMS
Problem 1
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INDEX
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