Structural Identification Of Organic Compounds With Spectroscopic Techniques

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

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ISBN: 9783527312405 | 3527312404
Cover: Hardcover
Copyright: 5/6/2005

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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.

Foreword

Preface

VII

1 Introduction to Nuclear Magnetic Resonance

(26)

1.1 Basic Principle of NMR

(5)

1.1.1 Nuclear Magnetic Momentum

(2)

1.1.2 Quantization of Angular Momentum and Magnetic Moment

(1)

1.1.3 Nuclear Magnetic Resonance

(2)

1.2 Chemical Shift

(2)

1.2.1 Shielding Constant

(1)

1.2.2 Chemical Shift o

(1)

1.3 Spin-spin Coupling

(3)

1.3.1 Spin-spin Coupling Produces NMR Signal Splitting

(1)

1.3.2 Energy Level Diagram

(1)

1.3.3 Coupling Constant J

(1)

1.4 Magnetization

(3)

1.4.1 Magnetization Concept

(1)

1.4.2 Rotating Frame

(2)

1.5 Relaxation Process

(4)

1.5.1 What is a Relaxation Process?

(1)

1.5.2 Longitudinal and Transverse Relaxation

(2)

1.5.3 Width of an NMR Signal

(1)

1.6 Pulse-Fourier Transform NMR Spectrometer

(7)

1.6.1 Application of Strong and Short RF Pulses

(2)

1.6.2 Time Domain Signal and Frequency Domain Spectrum, and their Fourier Transform

(2)

1.6.3 FT-NMR with Respect to the Fourier Decomposition

(2)

1.6.4 Advantages of an FT-NMR Spectrometer

(1)

1.7 Recent Developments in NMR Spectroscopy

(1)

1.8 References

(1)

2 ¹H NMR Spectroscopy

(64)

2.1 Chemical Shift

(10)

2.1.1 Reference for Chemical Shift

(1)

2.1.2 Factors Affecting Chemical Shifts

(6)

2.1.3 Chemical Shift Values of Common Functional Groups

(4)

2.2 Coupling Constant J

(7)

2.2.1 Vector Model for Couplings

(1)

2.2.2 ¹J and ²J

(1)

2.2.3 ³J

(3)

2.2.4 Coupling Constants of Long-range Couplings

(1)

2.2.5 Couplings in a Phenyl Ring or in a Heteroaromatic Ring

(2)

2.3 Spin-spin Coupling System and Classification of NMR Spectra

(7)

2.3.1 Chemical Equivalence

(4)

2.3.2 Magnetic Equivalence

(1)

2.3.3 Spin System

(1)

2.3.4 Classification of NMR Spectra

(1)

2.4 Common Second-order Spectra

(5)

2.4.1 AB System

(2)

2.4.2 AB2 System

(1)

2.4.3 AMX System

(1)

2.4.4 ABX System

(2)

2.4.5 AA'BB' System

(1)

2.5 Spectra of Common Functional Groups

(4)

2.5.1 Substituted Phenyl Ring

(3)

2.5.2 Substituted Heteroaromatic Ring

(1)

2.5.3 Mono-substituted Ethylene

(1)

2.5.4 Normal Long-chain Alkyl

(1)

2.6 Methods for Assisting the Spectrum Analysis

(1)

2.6.1 Using a Spectrometer with a High Frequency

(1)

2.6.2 Deuterium Exchange

(1)

2.6.3 Medium Effect

(1)

2.6.4 Shift Reagents

(1)

2.6.5 Spectral Simulation by Computer

(1)

2.7 Double Resonance

(8)

2.7.1 Spin Decoupling

(4)

2.7.2 Nuclear Overhauser Effect

(3)

2.8 Dynamic Nuclear Magnetic Resonance

(4)

2.8.1 Description of Dynamic Nuclear Magnetic Resonance

(2)

2.8.2 Spectral Peak of Reactive Hydrogen Atom (OH, NH and SH)

(2)

2.9 Interpreting ¹H NMR Spectra

(15)

2.9.1 Sampling and Measurement

(1)

2.9.2 Steps for ¹H Spectrum Interpretation

(3)

2.9.3 Examples of ¹H Spectrum Interpretation

(11)

2.10 References

(2)

3 ¹³C NMR Spectroscopy

(36)

3.1 Introduction

(1)

3.1.1 Advantages of ¹³C NMR Spectra

(1)

3.1.2 Difficulties in the Measurement of ¹³C NMR Spectra

(1)

3.1.3 ¹³C NMR Spectra

(1)

3.2 Chemical Shift

(9)

3.2.1 Paramagnetic Shielding is the Decisive Factor for Chemical Shifts

(1)

3.2.2 Alkanes and their Derivatives

(2)

3.2.3 Cycloalkanes and their Derivatives

(1)

3.2.4 Alkenes and their Derivatives

(1)

3.2.5 Benzene and its Derivatives

(2)

3.2.6 Carbonyl Compounds

(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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Structural Identification Of Organic Compounds With Spectroscopic Techniques

Summary

Author Biography

Table of Contents

Supplemental Materials