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Spectrometric Identification of Organic Compounds, 7th Edition

by: Robert M. Silverstein (State Univ. of New York, College of Environmental Science & Forestry); Francis X. Webster (State Univ. of New York, College of Environmental Science & Forestry); David Kiemle (State University of New York, College of Environmen

Spectrometric Identification of Organic Compounds, 7th Edition

ISBN 13:
9780471393627
ISBN 10:
0471393622
Edition: 7th
Format: Hardcover
Copyright: 01/01/2005
Publisher: WILEY
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Summary

Originally published in 1962, this was the first book to explore teh identification of organic compounds using spectroscopy. It provides a thorough introduction to the three areas of spectrometry most widely used in spectrometric identification: mass spectrometry, infrared spectrometry, and nuclear magnetic resonance spectrometry. A how-to, hands-on teaching manual with considerably expanded NMR coverage--NMR spectra can now be intrepreted in exquisite detail. This book: * Uses a problem-solving approach with extensive reference charts and tables. * Offers an extensive set of real-data problems offers a challenge to the practicing chemist

Mass Spectrometry

(71)

Introduction

(1)

Instrumentation

(1)

Ionization Methods

(5)

Gas-Phase Ionization Methods

(1)

Electron Impact Ionization

(1)

Chemical Ionization

(1)

Desorption Ionization Methods

(1)

Field Desorption Ionization

(1)

Fast Atom Bombardment Ionization

(1)

Plasma Desorption Ionization

(1)

Laser Desorption Ionization

(1)

Evaporative Ionization Methods

(1)

Thermospray Mass Spectrometry

(1)

Electrospray Mass Spectrometry

(2)

Mass Analyzers

(5)

Magnetic Spector Mass Spectrometers

(1)

Quadrupole Mass Spectrometers

(1)

Ion Trap Mass Spectrometers

(2)

Time-of-Flight Mass Spectrometer

(1)

Fourier Transform Mass Spectrometer

(1)

Tandem Mass Spectrometry

(1)

Interpretation of El Mass Spectra

(6)

Recognition of the Molecular Ion Peak

(1)

Determination of a Molecular Formula

(1)

Unit-Mass Molecular Ion and Isotope Peaks

(1)

High-Resolution Molecular Ion

(1)

Use of the Molecular Formula. Index of Hydrogen Deficiency

(1)

Fragmentation

(2)

Rearrangements

(1)

Mass Spectra of Some Chemical Classes

(53)

Hydrocarbons

(1)

Saturated Hydrocarbons

(1)

Alkenes (Olefins)

(1)

Aromatic and Aralkyl Hydrocarbons

(1)

Hydroxy Compounds

(1)

Alcohols

(2)

Phenols

(1)

Ethers

(1)

Aliphatic Ethers (and Acetals)

(1)

Aromatic Ethers

(1)

Ketones

(1)

Aliphatic Ketones

(1)

Cyclic Ketones

(1)

Aromatic Ketones

(1)

Aldehydes

(1)

Aliphatic Aldehydes

(1)

Aromatic Aldehydes

(1)

Carboxylic Acids

(1)

Aliphatic Acids

(1)

Aromatic Acids

(1)

Carboxylic Esters

(1)

Aliphatic Esters

(1)

Benzyl and Phenyl Esters

(1)

Esters of Aromatic Acids

(1)

Lactones

(1)

Amines

(1)

Aliphatic Amines

(1)

Cyclic Amines

(1)

Aromatic Amines (Anilines)

(1)

Amides

(1)

Aliphatic Amides

(1)

Aromatic Amides

(1)

Aliphatic Nitriles

(1)

Nitro Compounds

(1)

Aliphatic Nitro Compounds

(1)

Aromatic Nitro Compounds

(1)

Aliphatic Nitrites

(1)

Aliphatic Nitrates

(1)

Sulfur Compounds

(1)

Aliphatic Mercaptans (Thiols)

(1)

Aliphatic Sulfides

(1)

Aliphatic Disulfides

(1)

Halogen Compounds

(1)

Aliphatic Chlorides

(1)

Aliphatic Bromides

(1)

Aliphatic Iodides

(1)

Aliphatic Fluorides

(1)

Benzyl Halides

(1)

Aromatic Halides

(1)

Heteroaromatic Compounds

(1)

References

(1)

Student Exercises

(8)

Appendices

(1)

Formulas Masses

(21)

Common Fragment Ions

(2)

Common Fragments Lost

(2)

Infrared Spectrometry

(55)

Introduction

(1)

Theory

(6)

Coupled Interaction

(1)

Hydrogen Bonding

(2)

Instrumentation

(1)

Dispersion IR Spectrometer

(1)

Fourier Transform Infrared Spectrometer (Interferometer)

(1)

Sample Handling

(1)

Interpretations of Spectra

(2)

Characteristic Group Absorption of Organic Molecules

(45)

Normal Alkanes (Paraffins)

(1)

C---H Stretching Vibrations

(1)

C---H Bending Vibrations Methyl Groups

(1)

Branched-Chain Alkanes

(1)

C---H Stretching Vibrations Tertiary C---H Groups

(1)

C---H Bending Vibrations gem-Dimethyl Groups

(1)

Cyclic Alkanes

(1)

C---H Stretching Vibrations

(1)

C---H Bending Vibrations

(1)

Alkenes

(1)

C---C Stretching Vibrations Unconjugated Linear Alkenes

(1)

Alkene C---H Stretching Vibrations

(1)

Alkene C---H Bending Vibrations

(1)

Alkynes

(1)

C---C Stretching Vibrations

(1)

C---H Stretching Vibrations

(1)

C---H Bending Vibrations

(1)

Mononuclear Aromatic Hydrocarbons

(1)

Out-of-Plane C---H Bending Vibrations

(1)

Polynuclear Aromatic Hydrocarbons

(1)

Alcohols and Phenols

(1)

O---H Stretching Vibrations

(1)

C---O Stretching Vibrations

(1)

O---H Bending Vibrations

(1)

Ethers, Epoxides, and Peroxides

(1)

C---O Stretching Vibrations

(1)

Ketones

(1)

C---O Stretching Vibrations

(2)

C---C(=O)---C Stretching and Bending Vibrations

(1)

Aldehydes

(1)

C---O Stretching Vibrations

(1)

C---H Stretching Vibrations

(1)

Carboxylic Acids

(1)

O---H Stretching Vibrations

(1)

C=O Stretching Vibrations

(1)

C---O Stretching and O---H Bending Vibrations

(1)

Carboxylate Anion

(1)

Esters and Lactones

(1)

C=O Stretching Vibrations

(1)

C---O Stretching Vibrations

(1)

Acid Halides

(1)

C=O Stretching Vibrations

(1)

Carboxylic Acid Anhydrides

(1)

C=O Stretching Vibrations

(1)

C---O Stretching Vibrations

(1)

Amides and Lactams

(1)

N---H Stretching Vibrations

(1)

C=O Stretching Vibrations (Amide I Band)

100

(1)

N---H Bending Vibrations (Amide II Band)

100

(1)

Other Vibration Bands

101

(1)

C=O Stretching Vibrations of Lactams

101

(1)

Amines

101

(1)

N---H Stretching Vibrations

101

(1)

N---H Bending Vibrations

101

(1)

C---N Stretching Vibrations

102

(1)

Amine Salts

102

(1)

N---H Stretching Vibrations

102

(1)

N---H Bending Vibrations

102

(1)

Amino Acids and Salts of Amino Acids

102

(1)

Nitriles

103

(1)

Isonitriles (R---N=C), Cyanates (R---O---C=N), Isocyanates (R---N=C=O), Thiocyanates (R---S---C=N), Isothiocyanates (R---N=C=S)

104

(1)

Compounds Containing---N=N

104

(1)

Covalent Compounds Containing Nitrogen-Oxygen Bonds

104

(1)

N=O Stretching Vibrations Nitro Compounds

104

(1)

Organic Sulfur Compounds

105

(1)

S=H Stretching Vibrations Mercaptans

105

(1)

C---S and C=S Stretching Vibrations

106

(1)

Compounds Containing Sulfur---Oxygen Bonds

106

(1)

S=O Stretching Vibrations Sulfoxides

106

(1)

Organic Halogen Compounds

107

(1)

Silicon Compounds

107

(1)

Si---H Vibrations

107

(1)

SiO---H and Si---O Vibrations

107

(1)

Silicon---Halogen Stretching Vibrations

107

(1)

Phosphorus Compounds

107

(1)

P=O and P---O Stretching Vibrations

107

(1)

Heteroaromatic Compounds

107

(1)

C---H Stretching Vibrations

107

(1)

N---H Stretching Frequencies

108

(1)

Ring Stretching Vibrations (Skeletal Bands)

108

(1)

C---H Out-of-Plane Bending

108

(1)

References

108

(2)

Student Exercises

110

(9)

Appendices

119

(1)

Transparent Regions of Solvents and Mulling Oils

119

(1)

Characteristic Group Absorptions

120

(5)

Absorptions for Alkenes

125

(1)

Absorptions for Phosphorus Compounds

126

(1)

Absorptions for Heteroaromatics

126

(1)

Proton Magnetic Resonance Spectrometry

127

(77)

Introduction

127

(1)

Theory

127

(8)

Magnetic Properties of Nuclei

127

(1)

Excitation of Spin 1/2 Nuclei

128

(2)

Relaxation

130

(5)

Instrumentation and Sample Handling

135

(2)

Instrumentation

135

(1)

Sensitivity of NMR Experiments

136

(1)

Solvent Selection

137

(1)

Chemical Shift

137

(6)

Spin Coupling, Multiplets, Spin Systems

143

(17)

Simple and Complex First Order Multiplets

145

(1)

First Order Spin Systems

146

(1)

Pople Notions

147

(1)

Further Examples of Simple, First-Order Spin Systems

147

(1)

Analysis of First-Order Patterns

148

(12)

Protons on Oxygen, Nitrogen, and Sulfur Atoms. Exchangeable Protons

160

Protons on an Oxygen Atom

150

(1)

Alcohols

150

(3)

Water

153

(1)

Phenols

153

(1)

Enols

153

(1)

Carboxylic Acids

153

(1)

Protons on Nitrogen

153

(2)

Protons on Sulfur

155

(1)

Protons on or near Chlorine, Bromine, or Iodine Nuclei

155

(1)

Coupling of Protons to Other Important Nuclei (19F, D, 31P, 29Si, and 13C)

155

(2)

Coupling of Protons to 19F

155

(1)

Coupling of Protons to D

155

(1)

Coupling of Protons to 31P

156

(1)

Coupling of Protons to 29Si

156

(1)

Coupling of Protons to 13C

156

(1)

Chemical Shift Equivalence

157

(5)

Determination of Chemical Shift Equivalence by Interchange Through Symmetry Operations

157

(1)

Interchange by Rotation Around a Simple Axis of Symmetry (Cn)

157

(1)

Interchange by Reflection Through a Plane of Symmetry (σ)

157

(1)

Interchange by Inversion Through a Center of Symmetry (i)

158

(1)

No Interchangeability by a Symmetry Operations

158

(1)

Determination of Chemical Shift Equivalence by Tagging (or Substitution)

159

(1)

Chemical Shift Equivalence by Rapid Interconversion of Structures

160

(1)

Keto-Enol Interconversion

160

(1)

Interconversion Around a ``Partial Double Bond'' (Restricted Rotation)

160

(1)

Interconversion Around the Single Bond of Rings

160

(1)

Interconversion Around the Single Bonds of Chains

161

(1)

Magnetic Equivalence (Spin-Coupling Equivalence)

162

(2)

AMX, ABX, and ABC Rigid Systems with Three Coupling Constants

164

(1)

Confirmationally Mobile, Open-Chain Systems. Virtual Coupling

165

(4)

Unsymmetrical Chains

165

(1)

1-Nitropropane

165

(1)

1-Hexanol

165

(2)

Symmetrical Chains

167

(1)

Dimethyl Succinate

167

(1)

Dimethyl Glutarate

167

(1)

Dimethyl Adipate

167

(1)

Dimethyl Pimelate

168

(1)

Less Symmetrical Chains

168

(1)

3-Methylglutaric Acid

168

(1)

Chirality

169

(2)

One Chiral Center, Ipsenol

169

(2)

Two Chiral Centers

171

(1)

Vicinal and Geminal Coupling

171

(1)

Low-Range Coupling

172

(1)

Selective Spin Decoupling. Double Resonance

173

(1)

Nuclear Overhauser Effect, Difference Spectrometry, 1H 1H Proximity Through Space

173

(2)

Conclusion

175

(29)

References

176

(1)

Student Exercises

177

(11)

Appendices

188

(1)

Chemicals Shifts of a Proton

188

(3)

Effect on Chemical Shifts by Two or Three Directly Attached Functional Groups

191

(2)

Chemical Shifts in Alicyclic and Heterocyclic Rings

193

(1)

Chemical Shifts in Unsaturated and Aromatic Systems

194

(3)

Protons on Heteroatoms

197

(1)

Proton Spin-Coupling Constants

198

(2)

Chemical Shifts and Multiplicities of Residual Protons in Commercially Available Deuterated Solvents

200

(1)

1H NMR Data

201

(2)

Proton NMR Chemical Shifts of Amino Acids in D2O

203

(1)

Carbon-13 NMR Spectrometry

204

(41)

Introduction

204

(1)

Theory

204

(7)

1H Decoupling Techniques

204

(1)

Chemical Shift Scale and Range

205

(1)

T1 Relaxation

206

(1)

Nuclear Overhauser Enhancement (NOE)

207

(2)

13C---1H Sping Coupling (J Values)

209

(1)

Sensitivity

210

(1)

Solvents

210

(1)

Interpretation of a Simple 13C Spectrum: Diethyl Phthalate

211

(2)

Quantitative 13C Analysis

213

(1)

Chemical Shift Equivalence

214

(1)

DEPT

215

(2)

Chemical Classes and Chemical Shifts

217

(28)

Alkanes

218

(1)

Linear and Branched Alkanes

218

(1)

Effect of Substituents on Alkenes

218

(2)

Cycloalkanes and Saturated Heterocyclics

220

(1)

Alkenes

220

(1)

Alkynes

221

(1)

Aromatic Compounds

222

(1)

Heteroaromatic Compounds

223

(1)

Alcohols

223

(2)

Ethers, Acetals, and Epoxides

225

(1)

Halides

225

(1)

Amines

226

(1)

Thiols, Sulfides, and Disulfides

226

(1)

Functional Groups Containing Carbon

226

(1)

Ketones and Aldehydes

227

(1)

Carboxylic Acids, Esters, Chlorides, Anhydrides, Amides, and Nitriles

227

(1)

Oximes

227

(1)

References

228

(1)

Student Exercises

229

(11)

Appendices

240

(1)

The 13C Chemical Shifts, Couplings and Multiplicities of Common NMR Solvents

240

(1)

13C Chemical Shift for Common Organic Compounds in Different Solvents

241

(1)

The 13C Correlation Chart for Chemical Classes

242

(2)

13C NMR Data for Several Natural Products (δ)

244

(1)

Correlation NMR Spectrometry; 2-D NMR

245

(71)

Introduction

245

(1)

Theory

246

(3)

Correlation Spectrometry

249

(2)

1H---1H Correlation: COSY

250

(1)

Ipsenol: 1H---1H COSY

251

(8)

Ipsenol: Double Quantum Filtered 1H---1H COSY

251

(3)

Carbon Detected 13C---1H COSY: Hector

254

(1)

Proton Detected 1H---13C COSY: HMQC

254

(1)

Ipsenol: Hector and HMQC

255

(2)

Ipsenol: Proton-Detected, Long Range 1H---13C Heteronuclear Correlation: HMBC

257

(2)

Caryophyllene Oxide

259

(6)

Caryophyllene Oxide: DQF-COSY

259

(1)

Caryophyllene Oxide: HMQC

259

(4)

Caryophyllene Oxide: HMBC

263

(2)

13C---13C Correlations: Inadequate

265

(2)

Inadequate: Caryophyllene Oxide

266

(1)

Lactose

267

(3)

DQF-COSY: Lactose

267

(3)

HMQC: Lactose

270

(1)

HMBC: Lactose

270

(1)

Relayed Coherence Transfer: TOCSY

270

(5)

2-D TOCSY: Lactose

270

(3)

1-D TOCSY: Lactose

273

(2)

HMQC -- TOCSY

275

(1)

HMQC -- TOCSY: Lactose

275

(1)

Roesy

275

(3)

Roesy: Lactose

275

(3)

VGSE

278

(4)

COSY: VGSE

278

(1)

TOCSY: VGSE

278

(1)

HMQC: VGSE

278

(3)

HMBC: VGSE

281

(1)

ROESY: VGSE

282

(1)

Gradient Field NMR

282

(34)

References

285

(1)

Student Exercises

285

(31)

NMR Spectrometry of Other Important Spin 1/2 Nuclei

316

(25)

Introduction

316

(1)

15N Nuclear Magnetic Resonance

317

(6)

19F Nuclear Magnetic Resonance

323

(3)

29Si Nuclear Magnetic Resonance

326

(1)

31P Nuclear Magnetic Resonance

327

(3)

Conclusion

330

(11)

References

332

(1)

Student Exercises

333

(5)

Appendices

338

(1)

Properties of Magnetically Active Nuclei

338

(3)

Solved Problems

341

(40)

Introduction

341

(40)

Problem 7.1 Discussion

345

(4)

Problem 7.2 Discussion

349

(4)

Problem 7.3 Discussion

353

(7)

Problem 7.4 Discussion

360

(7)

Problem 7.5 Discussion

367

(6)

Problem 7.6 Discussion

373

(1)

Student Exercises

374

(7)

Assigned Problems

381

Introduction

381

Problems

382

Amazon no longer offers textbook rentals. We do!

Spectrometric Identification of Organic Compounds, 7th Edition

Spectrometric Identification of Organic Compounds, 7th Edition

9780471393627

0471393622

Summary

Table of Contents

Supplemental Materials

Write a Review

Amazon no longer offers textbook rentals. We do!

Spectrometric Identification of Organic Compounds, 7th Edition

Spectrometric Identification of Organic Compounds, 7th Edition

9780471393627

0471393622

Summary

Table of Contents

Supplemental Materials

Write a Review

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