VCD spectroscopy for organic chemists / Philip J. Stephens, Frank J. Devlin, James R. Cheeseman.

Format:

Book

Author/Creator:

Stephens, Philip J., 1940-2012.

Contributor:

Devlin, Frank J., 1949-

Cheeseman, James R., 1963-

Alumni and Friends Memorial Book Fund.

Language:

English

Subjects (All):

Vibrational spectra.

Vibrational circular dichroism.

Physical Description:

x, 360 pages : illustrations ; 25 cm

Place of Publication:

Boca Raton, FL : CRC Press, [2012]

Summary:

"The purpose of this book is to increase the awareness of organic chemists of the utility of VCD spectroscopy. To this end, successive chapters present experimental measurement of VCD spectra and their analysis; experimental measurement of vibrational absorption and VCD spectra; fundamental quantum-mechanical theory of the vibrational states of molecules and of their vibrational absorption and VCD spectra; application of the ab initio HF and DFT methods of quantum chemistry to the prediction of the molecular structures and vibrational states of organic molecules; conformational analysis of conformationally-flexible molecules; analysis of the vibrational absorption and VCD spectra of a number of conformationally-rigid chiral organic molecules; and studies of a set of chiral organic molecules which further document the power of VCD spectroscopy and make clear how wide is the applicability of this technique"-- Provided by publisher.

Contents:

Chapter 1 Introduction to Vibrational Circular Dichroism 1

References 8

Chapter 2 The Experimental Measurement of Vibrational Absorption and Vibrational Circular Dichroism Spectra 13

Vibrational Absorption Measurement 13

VCD Measurement 20

IR Absorption and VCD Spectra of Specific Molecules 24

Camphor 25

α-Pinene 29

Conclusions 35

References 46

Chapter 3 The Theory of IR and VCD Spectra 49

References 58

Chapter 4 Ab Initio Methods 59

Molecular Orbital Theory 60

Application of Analytical Derivative DFT Techniques to the Calculation of Forces, Hessian, APTs, and AATs 63

Origin Dependence of the AATs 66

Classification of Basis Sets 67

Functionals for DFT 69

Computational Procedures 71

Integration Grids 73

IR and VCD Spectra Calculation 73

References 76

Chapter 5 Conformational Analysis 81

References 114

Chapter 6 Analyses of the IR and VCD Spectra of Conformationally Rigid Molecules 115

Camphor 116

α-Pinene 130

Methyloxirane 146

Conclusions 161

Determination of Absolute Configuration 162

References 165

Chapter 7 Applications of VCD Spectroscopy to Organic Chemistry 167

Introduction 167

References 169

Tröger's Base 171

References 185

2-(1-Hydroxyethyl)-Chromen-4-One and Its 6-Br Derivative 186

Experimental IR and VCD Spectra 187

Conformational Analysis 188

Analysis of the IR and VCD Spectra 191

References 194

The Supramolecular Tetramer of 2,2'-Dimethyl-Biphenyl-6,6'-Dicarboxylic Acid 194

References 199

Trans-Para-Methyl-Phenyl-Glycidic Acid 199

Conformational Analysis 200

Analysis of the IR and VCD Spectra 202

References 206

The Cytotoxic Sesquiterpene Natural Product, Quadrone 206

Conformational Analysis 207

Analysis of the IR and VCD Spectra 209

References 216

A Chiral Oxadiazol-3-One Calcium Channel Blocker 219

References 225

The Alkaloid Natural Product, Schizozygine 225

Experimental IR and VCD Spectra 225

Conformational Analysis 225

Calculated IR and VCD Spectra 228

References 231

The Iridoid Natural Product, Plumericin 232

Experimental IR and VCD Spectra 232

Conformational Analysis 233

Calculated IR and VCD Spectra 236

References 239

The Chiral Alkane, D₃-Anti-Trans-Anti-Trans-Anti-Trans-Perhydrotriphenylene 240

References 254

The Isotopically Chiral Sulfoxide, Perdeuteriophenyl-Phenyl-Sulfoxide 256

Experimental IR and VCD Spectra 257

Conformational Analysis 257

Analysis of the IR and VCD Spectra 258

References 260

The Sex Pheromone of the Obscure Mealybug 262

References 263

A Thia-Bridged Triarylamine Heterohelicene 264

Reference 269

Enone Precursor to Nor-Suberosenone and Nor-Suberosanone 272

Conformational Analysis 273

Analysis of the IR and VCD Spectra 274

References 286

Conclusions 287.

Notes:

Includes bibliographical references and index.

Local Notes:

Acquired for the Penn Libraries with assistance from the Alumni and Friends Memorial Book Fund.

ISBN:

1439821712

9781439821718

OCLC:

775590824

Publisher Number:

99952543668