Structural Identification Of Organic Compounds With Spectroscopic Techniques,9783527312405

Structural Identification Of Organic Compounds With Spectroscopic Techniques

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Edition: 1st
ISBN13: 9783527312405
ISBN10: 3527312404
Format: Hardcover
Pub. Date: 2005-05-06
Publisher(s): Wiley-VCH
List Price: $108.41

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Summary

Clearly structured, easy to read and optimal to understand, this extensive compendium fills the gap between textbooks devoted to either spectra interpretation or basic physical principles. The original Chinese editions have already sold over 18,500 copies, and the material is taken from the latest literature from around the world, plus technical information provided by the manufacturers of spectroscopic instruments. Alongside basic methods, Professor Ning presents up-to-date developments in NMR, MS, IR and Raman spectroscopy, such as pulsed-field gradient technique, LC-NMR, and DOSY. He stresses the application of spectroscopic methods, interpreting them in great detail and depth since most of the selected spectra may be applied to practical work, as well as summarizing the rules for their interpretation. He also incorporates his original ideas, including a comparison of the common points in different spectroscopic techniques. This monograph features a unique structure, a typical example being the discussion of 2D NMR starting from pulse sequence units, which construct various pulse sequences for related 2D NMR. A complete chapter deals with the determination of configurations and conformations of organic compounds and even biological molecules from the viewpoint of spectroscopic methodologies, while one whole section is dedicated to the interpretation of mass spectra produced by soft ionization techniques. The principles of mass analyzers, especially the ion trap, are discussed in great depth, together with a concise summary of the MS fragmentation and rearrangement of common compounds, allowing readers to easily predict related mass spectrometric reactions. All the three kinds of library retrieval of mass spectra are presented in detail, together with recent developments in molecular vibration spectroscopy. The whole is rounded off with several appendices, including a subject index for rapid reference. With a foreword by the Nobel prizewinner, Richard R. Ernst.

Author Biography

Yong-Chen Ning studied at the Engineering-Physics Department of the Tsinghua University, Beijing, China where after his graduation he worked as a faculty member. From 1971 to 1978 he researched on structural identification of organic compounds at the Institute of Chemical Engineering in Shenyang. Between 1981 an 1984 Yong-Chen Ning participated in researches in the NMR, MS, X-ray diffraction an alkaloid laboratories of the Institute of Chemistry of Natural Substances in Paris. Since 1993 he is a full professor at the Tsinghua University. Yong-Chen Ning's books won several awards, e.g. the price for excellent teaching materials, and belong to the standard repertoire of chinese students.

Table of Contents

Foreword V
Preface VII
1 Introduction to Nuclear Magnetic Resonance 1(26)
1.1 Basic Principle of NMR
1(5)
1.1.1 Nuclear Magnetic Momentum
1(2)
1.1.2 Quantization of Angular Momentum and Magnetic Moment
3(1)
1.1.3 Nuclear Magnetic Resonance
4(2)
1.2 Chemical Shift
6(2)
1.2.1 Shielding Constant
6(1)
1.2.2 Chemical Shift o
7(1)
1.3 Spin-spin Coupling
8(3)
1.3.1 Spin-spin Coupling Produces NMR Signal Splitting
8(1)
1.3.2 Energy Level Diagram
9(1)
1.3.3 Coupling Constant J
10(1)
1.4 Magnetization
11(3)
1.4.1 Magnetization Concept
11(1)
1.4.2 Rotating Frame
12(2)
1.5 Relaxation Process
14(4)
1.5.1 What is a Relaxation Process?
14(1)
1.5.2 Longitudinal and Transverse Relaxation
15(2)
1.5.3 Width of an NMR Signal
17(1)
1.6 Pulse-Fourier Transform NMR Spectrometer
18(7)
1.6.1 Application of Strong and Short RF Pulses
18(2)
1.6.2 Time Domain Signal and Frequency Domain Spectrum, and their Fourier Transform
20(2)
1.6.3 FT-NMR with Respect to the Fourier Decomposition
22(2)
1.6.4 Advantages of an FT-NMR Spectrometer
24(1)
1.7 Recent Developments in NMR Spectroscopy
25(1)
1.8 References
26(1)
2 ¹H NMR Spectroscopy 27(64)
2.1 Chemical Shift
28(10)
2.1.1 Reference for Chemical Shift
28(1)
2.1.2 Factors Affecting Chemical Shifts
28(6)
2.1.3 Chemical Shift Values of Common Functional Groups
34(4)
2.2 Coupling Constant J
38(7)
2.2.1 Vector Model for Couplings
38(1)
2.2.2 ¹J and ²J
39(1)
2.2.3 ³J
40(3)
2.2.4 Coupling Constants of Long-range Couplings
43(1)
2.2.5 Couplings in a Phenyl Ring or in a Heteroaromatic Ring
43(2)
2.3 Spin-spin Coupling System and Classification of NMR Spectra
45(7)
2.3.1 Chemical Equivalence
45(4)
2.3.2 Magnetic Equivalence
49(1)
2.3.3 Spin System
50(1)
2.3.4 Classification of NMR Spectra
51(1)
2.4 Common Second-order Spectra
52(5)
2.4.1 AB System
52(2)
2.4.2 AB2 System
54(1)
2.4.3 AMX System
55(1)
2.4.4 ABX System
55(2)
2.4.5 AA'BB' System
57(1)
2.5 Spectra of Common Functional Groups
57(4)
2.5.1 Substituted Phenyl Ring
57(3)
2.5.2 Substituted Heteroaromatic Ring
60(1)
2.5.3 Mono-substituted Ethylene
60(1)
2.5.4 Normal Long-chain Alkyl
60(1)
2.6 Methods for Assisting the Spectrum Analysis
61(1)
2.6.1 Using a Spectrometer with a High Frequency
61(1)
2.6.2 Deuterium Exchange
61(1)
2.6.3 Medium Effect
62(1)
2.6.4 Shift Reagents
62(1)
2.6.5 Spectral Simulation by Computer
62(1)
2.7 Double Resonance
62(8)
2.7.1 Spin Decoupling
63(4)
2.7.2 Nuclear Overhauser Effect
67(3)
2.8 Dynamic Nuclear Magnetic Resonance
70(4)
2.8.1 Description of Dynamic Nuclear Magnetic Resonance
70(2)
2.8.2 Spectral Peak of Reactive Hydrogen Atom (OH, NH and SH)
72(2)
2.9 Interpreting ¹H NMR Spectra
74(15)
2.9.1 Sampling and Measurement
75(1)
2.9.2 Steps for ¹H Spectrum Interpretation
75(3)
2.9.3 Examples of ¹H Spectrum Interpretation
78(11)
2.10 References
89(2)
3 ¹³C NMR Spectroscopy 91(36)
3.1 Introduction
91(1)
3.1.1 Advantages of ¹³C NMR Spectra
91(1)
3.1.2 Difficulties in the Measurement of ¹³C NMR Spectra
92(1)
3.1.3 ¹³C NMR Spectra
92(1)
3.2 Chemical Shift
92(9)
3.2.1 Paramagnetic Shielding is the Decisive Factor for Chemical Shifts
93(1)
3.2.2 Alkanes and their Derivatives
93(2)
3.2.3 Cycloalkanes and their Derivatives
95(1)
3.2.4 Alkenes and their Derivatives
96(1)
3.2.5 Benzene and its Derivatives
97(2)
3.2.6 Carbonyl Compounds
99(2)
3.2.7 Influences of Hydrogen Bonds and the Medium
101(1)
3.3 Coupling and Decoupling Methods in ¹³C Spectra
101(4)
3.3.1 Coupling in ¹³C Spectra
101(1)
3.3.2 Broadband Decoupling
102(2)
3.3.3 Off-resonance Decoupling
104(1)
3.3.4 Selective Decoupling
104(1)
3.3.5 Gated Decoupling
104(1)
3.4 Relaxation
105(5)
3.4.1 Why does the Discussion of Relaxation of ¹³C Nuclei Require a Whole Section?
105(1)
3.4.2 Basic Concepts of the Relaxation of ¹³C Nuclei
105(1)
3.4.3 Measurement of Relaxation Time
106(3)
3.4.4 Application of T1
109(1)
3.5 Interpretation of ¹³C NMR Spectra
110(16)
3.5.1 Sampling and Plotting
110(1)
3.5.2 Steps for the Interpretation of ¹³C Spectra
111(2)
3.5.3 Examples of the Interpretation of ¹³C Spectra
113(13)
3.6 References
126(1)
4 Application of Pulse Sequences and Two-dimensional NMR Spectroscopy 127(88)
4.1 Fundamentals
127(27)
4.1.1 Transverse Magnetization Vector
127(3)
4.1.2 Coherence and Related Topics
130(2)
4.1.3 Spin Echo
132(4)
4.1.4 The Phase of an NMR Signal is Modulated by the Chemical Shift
136(1)
4.1.5 Bilinear Rotational Decoupling, BIRD
137(1)
4.1.6 Spin Locking
138(3)
4.1.7 Isotropic Mixing
141(2)
4.1.8 Selective Population Inversion
143(4)
4.1.9 Pulsed-field Gradient
147(5)
4.1.10 Shaped Pulse
152(2)
4.2 Spectrum Editing
154(8)
4.2.1 J Modulation or APT
154(3)
4.2.2 INEPT (Insensitive Nuclei Enhancement by Polarization Transfer)
157(3)
4.2.3 DEPT (Distortionless Enhancement by Polarization Transfer)
160(2)
4.3 Introduction to 2D NMR
162(3)
4.3.1 What are 2D NMR Spectra?
162(1)
4.3.2 Time Axis of 2D NMR
163(1)
4.3.3 Classification of 2D NMR Spectra
164(1)
4.3.4 Illustration of 2D NMR Spectra
164(1)
4.4 J Resolved Spectra
165(4)
4.4.1 Homonuclear J Resolved Spectra
165(3)
4.4.2 Heteronuclear J Resolved Spectra
168(1)
4.5 Heteronuclear Shift Correlation Spectroscopy
169(5)
4.5.1 H,C-COSY
169(3)
4.5.2 COLOC
172(1)
4.5.3 H,X-COSY
173(1)
4.6 Homonuclear Shift Correlation Spectroscopy
174(13)
4.6.1 COSY
175(3)
4.6.2 Phase-sensitive Homonuclear Shift Correlation Spectroscopy
178(4)
4.6.3 COSY-45 (β-COSY)
182(1)
4.6.4 COSY with Decoupling on the ω1 Axis
183(1)
4.6.5 COSYLR
184(2)
4.6.6 DQF-COSY
186(1)
4.7 NOESY and its Variations
187(5)
4.7.1 NOESY
188(1)
4.7.2 ROESY
189(2)
4.7.3 HOESY
191(1)
4.8 Relayed Correlation Spectra and Total Correlation Spectra
192(6)
4.8.1 RCOSY
192(1)
4.8.2 Heteronuclear Relayed COSY
193(2)
4.8.3 Total Correlation Spectroscopy (TOCSY)
195(3)
4.9 Multiple Quantum 2D NMR Spectra
198(4)
4.9.1 2D INADEQUATE
198(3)
4.9.2 Two-dimensional Double Quantum Spectra of ¹H
201(1)
4.10 ¹H Detected Heteronuclear Correlation Spectra
202(6)
4.10.1 HMQC and HSQC
203(3)
4.10.2 HMBC
206(2)
4.11 Combined 2D NMR Spectra
208(1)
4.12 Three-dimensional NMR Spectra
209(2)
4.12.1 Principle of Three-dimensional NMR Spectra
209(1)
4.12.2 Classification of 3D NMR Spectra
210(1)
4.12.3 Application of 3D NMR Spectra
210(1)
4.13 DOSY
211(2)
4.14 References
213(2)
5 Organic Mass Spectrometry 215(42)
5.1 Fundamentals of Organic Mass Spectrometry
216(3)
5.1.1 Instruments
216(1)
5.1.2 Major Specifications
216(1)
5.1.3 Mass Spectrum
217(1)
5.1.4 Ion Types in Organic Mass Spectrometry
217(2)
5.2 Mass Analyzers
219(14)
5.2.1 Single-focusing or Double-focusing Mass Analyzers
219(2)
5.2.2 Quadrupole Mass Analyzers
221(2)
5.2.3 Ion Trap
223(5)
5.2.4 Fourier Transform Mass Spectrometer
228(3)
5.2.5 Time-of-flight (TOF) MS
231(2)
5.3 Ionization
233(5)
5.3.1 Electron Impact Ionization, EI
233(1)
5.3.2 Chemical Ionization, CI
234(1)
5.3.3 Field Ionization and Field Desorption
235(1)
5.3.4 Fast Atom Bombardment, FAB, and Liquid Secondary Ion Mass Spectrometry, LSIMS
236(1)
5.3.5 Matrix-assisted Laser Desorption-ionization, MALDI
236(1)
5.3.6 Atmospheric Pressure Ionization, API
237(1)
5.4 Metastable Ions and their Measurement
238(8)
5.4.1 Metastable Ions Produced in the Second Field-free Region
240(1)
5.4.2 Metastable Ions Produced in the First Field-free Region
241(1)
5.4.3 Ion Kinetic Energy Spectrum (IKES)
242(1)
5.4.4 Mass-analyzed Ion Kinetic Energy Spectrum (MIKES)
242(1)
5.4.5 Linked Scanning
242(3)
5.4.6 Information Provided by Metastable Ions
245(1)
5.4.7 Peak Shapes of Metastable Ions
246(1)
5.5 Tandem Mass Spectrometry (MSn)
246(6)
5.5.1 Collision-induced Dissociation (CID)
246(2)
5.5.2 Tandem Mass Spectrometry
248(4)
5.6 Combination of Chromatography and Mass Spectrometry
252(2)
5.6.1 GC-MS
252(1)
5.6.2 LC-MS and LC-MSn
253(1)
5.7 References
254(3)
6 Interpretation of Mass Spectra 257(58)
6.1 Determination of Molecular Weight and Elemental Composition
257(8)
6.1.1 Determination of Molecular Weight by an EI Spectrum
257(2)
6.1.2 Determination of the Molecular Weight from a Multiply-charged Ion Cluster in an ESI Spectrum
259(2)
6.1.3 Postulation of the Molecular Weight from a Spectrum Obtained Using Soft Ionization Techniques
261(1)
6.1.4 Determination of the Molecular Formula from High Resolution MS Data
261(1)
6.1.5 Peak Matching
262(1)
6.1.6 Postulation of the Molecular Weight from Low Resolution MS Data
262(3)
6.1.7 Measurement of Exact Masses by a TOF or Quadrupole
265(1)
6.2 Reactions and their Mechanisms in Organic Mass Spectrometry
265(19)
6.2.1 Basic Knowledge
265(1)
6.2.2 Simple Cleavage
266(7)
6.2.3 Rearrangements
273(6)
6.2.4 Cleavage of Alicyclic Compounds
279(2)
6.2.5 Consecutive Decompositions of Primary Fragmentation Ions
281(1)
6.2.6 Stevenson-Audier's Rule
281(2)
6.2.7 Methods to Study Reaction Mechanisms of Organic Mass Spectrometry
283(1)
6.3 Mass Spectrum Patterns of Common Functional Groups
284(9)
6.3.1 Alkanes
284(2)
6.3.2 Unsaturated Hydrocarbons
286(1)
6.3.3 Aliphatic Compounds Containing Saturated Heteroatoms
287(3)
6.3.4 Aliphatic Compounds Containing Unsaturated Heteroatoms
290(1)
6.3.5 Alkyl Benzenes
291(1)
6.3.6 Aromatic Compounds with Heteroatom Substitutions
292(1)
6.3.7 Heteroaromatic Compounds and their Derivatives
293(1)
6.4 Interpretation of Mass Spectra
293(12)
6.4.1 Steps of the Interpretation
294(1)
6.4.2 Examples
295(10)
6.5 Library Retrieval of Mass Spectra
305(5)
6.6 Interpretation of the Mass Spectra from Soft Ionization
310(4)
6.6.1 Mass Spectra from CI
310(1)
6.6.2 Mass Spectra from FAB
311(1)
6.6.3 Mass Spectra from MALDI
312(1)
6.6.4 Mass Spectra from ESI
313(1)
6.6.5 Mass Spectra from APCI
314(1)
6.7 References
314(1)
7 Infrared Spectroscopy and Raman Spectroscopy 315(40)
7.1 General Information on Infrared Spectroscopy
315(1)
7.1.1 Wavelength and Wavenumber
315(1)
7.1.2 Near, Medium and Far Infrared Rays
316(1)
7.1.3 The Ordinate of IR Spectra
316(1)
7.2 Basic Theory of IR Spectroscopy
316(6)
7.2.1 IR Absorption Frequencies of a Diatomic Molecule
316(4)
7.2.2 IR Absorption Frequencies of a Polyatomic Molecule
320(2)
7.2.3 IR Absorption Intensities
322(1)
7.3 Characteristic Frequencies of Functional Groups
322(3)
7.3.1 Functional Groups Possessing Characteristic Frequencies
322(1)
7.3.2 Factors Affecting Absorption Frequencies
323(1)
7.3.3 Characteristic Frequencies of Common Functional Groups
324(1)
7.4 Interpretation of IR Spectra
325(9)
7.4.1 Wavenumber Regions of IR Absorption Bands
325(2)
7.4.2 Fingerprint and Functional Group Regions
327(1)
7.4.3 Key Points for the Interpretation of IR Spectra
328(1)
7.4.4 Examples of IR Spectrum Interpretation
329(5)
7.5 Recent Developments in Infrared Spectroscopy
334(12)
7.5.1 Step Scan
334(3)
7.5.2 Photo-acoustic Spectroscopy
337(2)
7.5.3 Time-resolved Spectroscopy
339(1)
7.5.4 Two-dimensional Infrared Spectroscopy
340(3)
7.5.5 Infrared Microscope and Chemical Imaging
343(1)
7.5.6 GC-FT-IR
344(2)
7.6 Principle and Application of Raman Spectroscopy
346(8)
7.6.1 Principle of Raman Spectroscopy
346(4)
7.6.2 Advantages and Applications of Raman Spectroscopy
350(2)
7.6.3 FT Raman Spectrometer
352(2)
7.7 References
354(1)
8 Identification of an Unknown Compound through a Combination of Spectra 355(44)
8.1 Structural Identification of an Unknown Compound by Combination of One-dimensional NMR and Other Spectra
356(2)
8.2 Determination of the Functional Groups (or Structural Units) of an Unknown Compound
358(3)
8.2.1 Substituted Benzene Ring
359(1)
8.2.2 Normal Long-chain Alkyl Groups
360(1)
8.2.3 Alcohols and Phenols
360(1)
8.2.4 Carbonyl Compounds
361(1)
8.3 Deduction of the Structure of an Organic Compound on the Basis of 2D NMR Spectra
361(8)
8.3.1 Shift Correlation Spectra as the Key to Structural Postulation
363(3)
8.3.2 Deduction of the Structure of an Unknown Compound by Using Mainly HMQC-TOCSY
366(2)
8.3.3 Postulating an Unknown Structure by 2D INADEQUATE
368(1)
8.4 Examples of Structural Identification or Assignment
369(29)
8.5 References
398(1)
9 Determination of Configuration and Conformation of Organic Compounds by Spectroscopic Methods 399(28)
9.1 NMR
400(17)
9.1.1 Chemical Shift
400(7)
9.1.2 Coupling Constants
407(7)
9.1.3 NOE
414(3)
9.2 Mass Spectrometry
417(5)
9.2.1 Utilizing Electron Impact Ionization
418(2)
9.2.2 Utilizing Soft Ionization
420(1)
9.2.3 Reaction Mass Spectrometry
421(1)
9.3 Infrared and Raman Spectroscopy
422(3)
9.4 References
425(2)
Appendix 1 Product Operator Formalism for Pulse Sequences 427(10)
Appendix 2 Characteristic Frequencies of Common Functional Groups 437(12)
Index 449

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