Amazon no longer offers textbook rentals. We do!

Organic Structural Spectroscopy

by: Lambert, Joseph B.; Shurvell, Herbert F.; Lightner, David; Cooks, Robert Graham

Organic Structural Spectroscopy

by: Lambert, Joseph B.; Shurvell, Herbert F.; Lightner, David; Cooks, Robert Graham

ISBN 13:
9780132586900
ISBN 10:
0132586908
Edition: 1st
Format: Hardcover
Copyright: 01/01/1998
Publisher: Prentice Hall
Newer Edition

Rent

Sorry, this item is currently unavailable.

Note: Supplemental materials are not guaranteed with Rental or Used book purchases.

Extend or Purchase Your Rental at Any Time

Need to keep your rental past your due date? At any time before your due date you can extend or purchase your rental through your account.

Summary

This book is the revision of a widely-respected book on spectroscopy. The book covers all four areas of organic spectroscopy including NMR, MS, electronic (including CD and optical rotary dispersion), and vibrational (which also includes Raman). The book is the most complete and comprehensive treatment on the subject. It covers currently used techniques for determining the structure of organic and biological compounds. It also has a strong emphasis on problem solving and is distinctly pedagogical. This book is ideal for any practicing or future organic or biochemist.

Preface

vii

1 Introduction

(7)

1-1 The Spectroscopic Approach to Structure

(1)

1-2 Contributions of Different Forms of Spectroscopy

(2)

1-2a Nuclear Magnetic Resonance Spectroscopy

(1)

1-2b Vibrational Spectroscopy

(1)

1-2c Electronic Spectroscopy

(1)

1-2d Mass Spectrometry

(1)

1-3 The Electromagnetic Spectrum

(1)

1-4 Molecular Weight and Molecular Formula

(2)

1-5 Structural Isomers and Stereoisomers, 5 Problems

(2)

PART I NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY

(144)

2 Introduction and Experimental Methods

(29)

2-1 Magnetic Properties of Nuclei

(3)

2-2 The Chemical Shift

(3)

2-3 Excitation and Relaxation

(2)

2-4 Pulsed Experiments

(2)

2-5 The Coupling Constant

(5)

2-6 Quantitation

(2)

2-7 Commonly Studied Nuclides

(2)

2-8 Experimental Methods

(3)

2-8a The Spectrometer and the Sample

(1)

2-8b Optimizing the Signal

(1)

2-8c Spectral Parameters

(2)

2-9 Dynamic Effects

(2)

2-10 Spectra of Solids

(2)

Problems

(2)

Bibliography

(1)

3 The Chemical Shift

(27)

3-1 Factors That Influence Proton Shifts

(4)

3-2 Proton Chemical Shifts and Structure

(6)

3-2a Saturated Aliphatics

(2)

3-2b Unsaturated Aliphatics

(2)

3-2c Aromatics

(1)

3-2d Protons on Oxygen and Nitrogen

(1)

3-3 Factors That Influence Carbon Shifts

(2)

3-4 Carbon Chemical Shifts and Structure

(6)

3-4a Saturated Aliphatics

(4)

3-4b Unsaturated Compounds

(1)

3-4c Carbonyl Groups

(1)

3-5 Summary and Tables of Chemical Shifts

(2)

Problems

(6)

Bibliography

(1)

4 The Coupling Constant

(25)

4-1 First- and Second-Order Spectra

(1)

4-2 Chemical and Magnetic Equivalence

(3)

4-3 Signs and Mechanisms: One Bond Couplings

(2)

4-4 Geminal Couplings

(2)

4-5 Vicinal Couplings

(2)

4-6 Long-Range Couplings

(1)

4-7 Spectral Analysis

(4)

4-8 Tables of Coupling Constants

(3)

Problems

(6)

Bibliography

(1)

5 Further Topics in One-Dimensional NMR

(28)

5-1 Spin-Lattice and Spin-Spin Relaxation

(5)

5-2 Reactions on the NMR Time Scale

(2)

5-3 Multiple Resonance

(5)

5-4 The Nuclear Overhauser Effect

101

(4)

5-5 Spectral Editing

105

(2)

5-6 Sensitivity Enhancement

107

(3)

5-7 Carbon Connectivity

110

(2)

5-8 Phase Cycling and Composite Pulses

112

(2)

Problems

114

(1)

Bibliography

115

(2)

6 Two-Dimensional NMR

117

(35)

6-1 Proton-Proton Correlation Through Coupling

117

(4)

6-2 Proton-Heteronucleus Correlation

131

(4)

6-3 Proton-Proton Correlation Through Space or Chemical Exchange

135

(3)

6-4 Carbon-Carbon Correlation

138

(2)

6-5 Higher Dimensions

140

(2)

6-6 Pulsed Field Gradients

142

(2)

6-7 Summary of Two-Dimensional Methods

144

(1)

Problems

145

(5)

Bibliography

150

(2)

PART II VIBRATIONAL SPECTROSCOPY

152

(100)

7 Introduction and Experimental Methods

152

(23)

7-1 Introduction

152

(1)

7-2 Vibrations of Molecules

153

(1)

7-3 Vibrational Spectra: Infrared and Raman

154

(3)

7-4 Units and Notation

157

(1)

7-5 Infrared Spectroscopy: Dispersive and Fourier Transform

158

(4)

7-5a Dispersive Infrared Spectrometers

158

(1)

7-5b Fourier Transform Infrared Spectrometers

159

(3)

7-6 Sampling Methods for Infrared Transmission Spectra

162

(3)

7-6a Liquids and Solutions

163

(1)

7-6b Solids

164

(1)

7-7 Raman Spectroscopy: Dispersive and Fourier Transform

165

(2)

7-7a Dispersive Raman Spectrometers

166

(1)

7-7b FT-Raman Spectrometers

167

(1)

7-8 Raman Sampling Methods

167

(3)

7-8a Liquids and Solutions

168

(1)

7-8b Solids

169

(1)

7-8c Depolarization Measurements

170

(1)

7-9 Special Techniques in Infrared Spectroscopy

170

(4)

7-9a Gas Phase Infrared Spectroscopy

170

(1)

7-9b Microsampling

171

(1)

7-9c Infrared Reflection Spectroscopy

171

(2)

7-9d Gas Chromatography and Infrared Spectroscopy (GC-IR)

173

(1)

Problems

174

(1)

Bibliography

174

(1)

8 Group Frequencies: Infrared and Raman

175

(26)

8-1 Introduction to Group Frequencies

175

(1)

8-2 Factors Affecting Group Frequencies

176

(11)

8-2a Symmetry

177

(2)

8-2b Mechanical Coupling of Vibrations

179

(1)

8-2c Fermi Resonance

180

(1)

8-2d Hydrogen Bonding

181

(1)

8-2e Ring Strain

182

(1)

8-2f Electronic Effects

183

(1)

8-2g Constitutional Isomerism

184

(1)

8-2h Stereoisomerism

185

(1)

8-2i Conformational Isomerism

186

(1)

8-2j Tautomerism (Dynamic Isomerism)

187

(1)

8-3 Infrared Group Frequencies

187

(1)

8-4 Raman Group Frequencies

188

(11)

Problems

199

(1)

Bibliography

200

(1)

9 Structural Analysis

201

(51)

9-1 Introduction

201

(1)

9-2 Preliminary Analysis

202

(6)

9-2a Introduction

202

(1)

9-2b Hydrocarbons or Hydrocarbon Groups

203

(1)

9-2c Compounds Containing Oxygen

204

(3)

9-2d Compounds Containing Nitrogen

207

(1)

9-3 The CH Stretching Region (3340-2700 cm(-1))

208

(3)

9-3a Introduction

208

(1)

9-3b Alkynes

208

(1)

9-3c Aromatic Compounds

208

(1)

9-3d Unsaturated Nonaromatic Compounds

209

(1)

9-3e Saturated Hydrocarbon Groups

210

(1)

9-3f Aldehydes

210

(1)

9-4 The Carbonyl Stretching Region (1850-1650 cm(-1))

211

(3)

9-4a Introduction

211

(3)

9-4b Compounds Containing a Single C = O Group

211

(2)

9-4c Compounds Containing Two C = O Groups

213

(1)

9-5 Aromatic Compounds

214

(2)

9-5a General

214

(1)

9-5b Substituted Aromatic Compounds

214

(1)

9-5c Raman Spectra of Aromatic Compounds

215

(1)

9-6 Compounds Containing Methyl Groups

216

(2)

9-6a General

216

(1)

9-6b Isopropyl and tert-Butyl Groups

217

(1)

9-7 Compounds Containing Methylene Groups

218

(1)

9-7a Introduction

218

(1)

9-7b CH(2) Bending (Scissoring)

218

(1)

9-7c CH(2) Wagging and Twisting

218

(1)

9-7d CH(2) Rocking

219

(1)

9-7e CH(2) Wagging in Vinyl and Vinylidene Compounds

219

(1)

9-7f Relative Numbers of CH(2) and CH(3) Groups

219

(1)

9-8 Unsaturated Compounds

219

(4)

9-8a The C = C Stretching Mode

219

(1)

9-8b Cyclic Compounds

219

(1)

9-8c The C = C Stretching Mode

220

(1)

9-8d CH = and CH(2) = Bending Modes

220

(3)

9-9 Compounds Containing Oxygen

223

(3)

9-9a General

223

(1)

9-9b Ethers

224

(1)

9-9c Alcohols and Phenols

224

(2)

9-9d Carboxylic Acids and Anhydrides

226

(1)

9-9e Esters

226

(1)

9-10 Compounds Containing Nitrogen

226

(5)

9-10a General

226

(1)

9-10b Amino Acids, Amines, and Amine Hydrohalides

226

(3)

9-10c Anilines

229

(1)

9-10d Nitriles

229

(1)

9-10e Nitro Compounds

230

(1)

9-10f Amides

230

(1)

9-10g Oximes

230

(1)

9-11 Compounds Containing Phosphorus and Sulfur

231

(4)

9-11a General

231

(1)

9-11b Phosphorus Acids and Esters

231

(1)

9-11c Aromatic Phosphorus Compounds

231

(1)

9-11d Compounds Containing C-S, S-S, and S-H Groups

232

(1)

9-11e Compounds Containing S=O Groups

233

(2)

9-12 Heterocyclic Compounds

235

(2)

9-12a General

235

(2)

9-12b Aromatic Heterocycles

237

(1)

9-12c Pyrimidines and Purines

236

(1)

9-12d Five-Membered Ring Compounds

236

(1)

9-12e NH Stretching Bands

236

(1)

9-13 Compounds Containing Halogens

237

(1)

9-13a General

237

(1)

9-13b CH(2)X Groups

238

(1)

9-13c Haloalkyl Groups

238

(1)

9-13d Aromatic Halogen Compounds

238

(1)

9-14 Boron, Silicon, and Organometallic Compounds

238

(1)

9-15 Isotopically Labeled Compounds

239

(1)

9-15a The Effect of (2)H and (13)C Isotopic Substitution on Stretching Modes

239

(1)

9-15b The Effect of Deuterium Substitution on Bending Modes

239

(1)

9-16 Using the Literature on Vibrational Spectra

240

(2)

9-16a Collections of Spectra

240

(1)

9-16b Infrared Spectra

241

(1)

9-16c Raman Spectra

241

(1)

9-16d Sources of References to Published Spectra

242

(1)

Problems

242

(8)

Bibliography

250

(2)

PART III ELECTRONIC ABSORPTION AND CHIROPTICAL SPECTROSCOPY

252

(94)

10 Introduction and Experimental Methods

252

(22)

10-1 Introduction

252

(2)

10-2 Measurement of Ultraviolet-Visible Light Absorption

254

(4)

10-2a Wavelength and XXX(max')

255

(1)

10-2b Beer-Bouger-Lambert Law and XXX(max')

255

(1)

10-2c Shape of Absorption Curves: The Franck-Condon Principle

256

(1)

10-2d Solvent Effects and XXX(max) Shifts

257

(1)

10-3 Measurements Using Polarized Light

258

(8)

10-3a Ordinary Absorption and Chiroptical Spectroscopy

261

(1)

10-3b Circular Birefringence and Circular Dichroism

261

(2)

10-3c Optical Rotatory Dispersion (ORD) and Circular Dichroism (CD) Quantities

263

(1)

10-3d ORD and CD Spectra and Cotton Effects

264

(2)

10-3e Relative Advantages of ORD and CD

266

(1)

10-4 Quantitative Measurements

266

(3)

10-4a Difference Spectroscopy

266

(2)

10-4b Deviations From Beer's Law

268

(1)

10-4c Isosbestic Points

268

(1)

10-5 Experimental Aspects

269

(3)

10-5a Solvents

269

(1)

10-5b Cells (Cuvettes) and Sample Preparation

269

(2)

10-5c Calibration of ORD and CD Instruments

271

(1)

10-5d Possible Sources of Error

271

(1)

Problems

272

(1)

Bibliography

273

(1)

11 UV-Vis, CD, and ORD

274

(30)

11-1 Electronic Transitions and Chromophores

274

(5)

11-1a Classification of Electronic Transitions

275

(2)

11-1b Singlet and Triplet States

277

(1)

11-1c Allowed and Forbidden Transitions

277

(1)

11-1d Absorption Intensity: Oscillator and Rotatory Strengths

278

(1)

11-2 Isolated Chromophores

279

(6)

11-2a Carbonyl: Ketone and Aldehyde Absorption

279

(2)

11-2b Carbonyl: Ketone ORD and CD

281

(1)

11-2c Carbonyl: Acid, Ester, and Amide Absorption

281

(2)

11-2d Alkenes

283

(2)

11-3 Conjugated Chromophores

285

(2)

11-3a Dienes and Polyenes

285

(1)

11-3b XXX, XXX-Unsaturated Carbonyls

286

(1)

11-4 Aromatic Compounds

287

(5)

11-5 Important Naturally Occurring Chromophores

292

(7)

11-5a Amino Acids, Peptides, and Proteins

292

(4)

11-5b Nucleic Acids and Polynucleotides

296

(1)

11-5c Porphyrins and Metalloporphyrins

296

(3)

11-6 Worked Problems

299

(2)

Problems

301

(2)

Bibliography

303

(1)

12 Structural Analysis

304

(42)

12-1 Applications of the Woodward-Fieser Rules

304

(5)

12-1a Conjugated Dienes and Polyenes

304

(3)

12-1b Conjugated Ketones, Aldehydes, Acids, and Esters

307

(2)

12-2 Determination of Absolute Configuration

309

(8)

12-2a The Octant Rule

309

(3)

12-2b Exciton Coupling and the Exciton Chirality Rule

312

(5)

12-3 Steric Effects

317

(1)

12-4 Solvent Effects and Tautomerism

318

(2)

12-5 Conformational Analysis

320

(2)

12-6 Hydrogen Bonding Studies

322

(1)

12-7 Homoconjugation

323

(2)

12-8 Charge Transfer Bands

325

(2)

12-9 Worked Problems

327

(10)

Problems

337

(7)

Bibliography

344

(2)

PART IV MASS SPECTROMETRY

346

(133)

13 Ionization and Mass Analysis

346

(46)

13-1 Scope and Applications of Mass Spectrometry

346

(2)

13-2 Sample Introduction

348

(2)

13-2a Direct Introduction

349

(1)

13-2b Introduction via Gas or Liquid Chromatographs

349

(1)

13-2c Other Sample Introduction Methods

350

(1)

13-3 Ionization

350

(24)

13-3a Electron Ionization (EI)

351

(4)

13-3b Chemical Ionization (CI)

355

(7)

13-3c Desorption Ionization (DI) Including Matrix-Assisted Laser Desorption Ionization (MALDI)

362

(7)

13-3d Spray Ionization (SI) Including Electrospray Ionization (ESI)

369

(5)

13-3e Ionization Summary

374

(1)

13-4 Mass Analysis

374

(12)

13-4a Magnetic Sectors

374

(2)

13-4b Time-of-Flight(TOF) Analyzers

376

(1)

13-4c Quadrupole Mass Filters

377

(2)

13-4d Quadrupole Ion Traps

379

(1)

13-4e Ion Cyclotron Resonance (ICR)

380

(2)

13-4f High Resolution Mass Spectrometers

382

(1)

13-4g Tandem Mass Spectrometers

382

(2)

13-4h Ion Detection and Data Handling

384

(2)

13-5 Worked Problems

386

(3)

Problems

389

(1)

Bibliography

390

(2)

14 Fragmentation and Ion Chemistry

392

(46)

14-1 General Principles of Fragmentation

392

(5)

14-1a Energetics of Dissociation

392

(1)

14-1b Odd- and Even-Electron Ions

393

(1)

14-1c Stevenson's Rule

394

(1)

14-1d Rearrangement vs. Simple Cleavage

394

(1)

14-1e Ions of High Internal Energy

395

(1)

14-1f Proximate vs. Remote Fragmentation

395

(1)

14-1g Distonic Ions

396

(1)

14-1h Charge Localization

396

(1)

14-1i Characteristic Fragment Ions and Neutral Fragments

396

(1)

14-2 Amine and Ether Type Fragmentation

397

(13)

14-2a Amines

397

(4)

14-2b Ethers

401

(5)

14-2c Alcohols and Phenols

406

(4)

14-2d Halides

410

(1)

14-3 Ketone and Aldehyde Type Fragmentation

410

(4)

14-4 Fragmentation of Other Functional Groups

414

(3)

14-4a Carboxylic Acids

414

(1)

14-4b Esters

414

(3)

14-4c Amides

417

(1)

14-4d Aliphatic Hydrocarbons

417

(1)

14-4e Aromatic Hydrocarbons

417

(1)

14-5 Negative Ion Fragmentation

417

(2)

14-6 Fragmentation in CI, DI, and SI

419

(2)

14-7 Ion Chemistry

421

(11)

14-7a Unimolecular Fragmentation

421

(5)

14-7b Ion-Molecule Reactions

426

(3)

14-7c Advanced Ion Chemistry

429

(3)

14-8 Worked Problems

432

(4)

Problems

436

(1)

Bibliography

437

(1)

15 Chemical Analysis

438

(35)

15-1 Molecular Weight Determination

438

(1)

15-2 Molecular Structure Determination

439

(2)

15-3 Molecular Formula Determination (Exact Mass Measurement)

441

(1)

15-4 Isotopic Analysis

442

(7)

15-4a Recognition of Elements: Isotopic Signatures

442

(1)

15-4b Number of Carbon Atoms in a Molecule

442

(1)

15-4c Calculation of Ion Abundance Ratios From the Molecular Formula

443

(1)

15-4d Typical Molecular Ion Isotopic Profiles for Organic and Biological Compounds

444

(2)

15-4e Determination of Molecular Formula From Isotopic Abundances

446

(1)

15-4f Isotopic Purity Determination

447

(2)

15-5 Quantitative Analysis

449

(1)

15-6 Mixture Analysis

450

(5)

15-6a Chromatography-Mass Spectrometry

450

(2)

15-6b Tandem Mass Spectrometry (MS-MS)

452

(3)

15-7 Thermochemical Determinations: Heats of Formation and Ion Affinities

455

(1)

15-8 Other Applications of Mass Spectrometry

456

(2)

15-8a Industrial Applications and Process Control

456

(1)

15-8b Isotope Ratio Mass Spectrometry

456

(1)

15-8c Elemental Analysis

457

(1)

15-8d Surface Elemental Analysis

457

(1)

15-9 Worked Problems

458

(9)

Problems

467

(5)

Bibliography

472

(1)

Appendix to Part IV

473

(6)

PART V INTEGRATED PROBLEMS

479

(78)

16 Integrated Problems

480

(77)

Index

557

Amazon no longer offers textbook rentals. We do!

Organic Structural Spectroscopy

Organic Structural Spectroscopy

9780132586900

0132586908

Summary

Table of Contents

Supplemental Materials

Write a Review

Amazon no longer offers textbook rentals. We do!

Organic Structural Spectroscopy

Organic Structural Spectroscopy

9780132586900

0132586908

Summary

Table of Contents

Supplemental Materials

Write a Review

Related Products