Free download Organic Spectroscopy By William Kemp 3rd Edition

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Authors of:  Organic Spectroscopy By William Kemp 3rd Edition

William Kemp

Table of Contents in Organic Spectroscopy By William Kemp 3rd Edition

Preface to the First Edition

Preface to the Second Edition

Preface to the Third Edition

Acknowledgments

1 Energy and the Electromagnetic Spectrum

1.1 Units

1.2 The Electromagnetic Spectrum

1.3 Absorption of Electromagnetic Radiation by Organic

Molecules

Supplement 1

15.1 Spectroscopy and Computers

15.2 Fourier Transforms-Frequency and Time

15.3 Spectroscopy and Chromatography-Hyphenated

Techniques

15.3 .1 Gas chromatography and spectroscopy

15.3.2 Liquid chromatography and spectroscopy

Further reading

2 Infrared Spectroscopy

2.1 Units of Frequency. Wavelength and Wavenumber

2.2 Molecular Vibrations

2.2.1 Calculation of vibrational frequencies

2.2.2 Modes of vibration

2.2.3 Quantum restrictions

2.3 Factors Influencing Vibrational Frequencies

2.3.1 Vibrational coupling

2.3.2 Hydrogen bonding

2.3.3 Electronic effects

2.3.4 Bond angles

2.3.5 Field effects

2.4 Instrumentation-the Infrared Spectrometer-Dispersive and

Interferometric Instruments

2.4.1 Infrared sources

2.4.2 Monochromators

2.4.3 Detectors

2.4.4 Mode of operation—dispersive instruments-optical null and

ratio recording

2.4.5 Mode of operation-interferometric instruments-Fourier

Transform infrared spectroscopy

2.4.6 Calibration of the frequency scale

2.4.7 Absorbance and transmittance scales

2.5 Sampling Techniques

2.5.1 Gases

2.5.2 Liquids

2.5.3 Solids

2.5.4 Solutions

2.6 Applications of Infrared Spectroscopy-Identity by

Fingerprinting

2.7 Applications of Infrared Spectroscopy-Identification of

Functional Groups

Correlation Charts

2.8 The Carbon Skeleton (Chart 1)

2.8.1 Aromatics (Chart l(i))

2.8.2 Alkanes and alkyl groups (Chart l(ii))

2.8.3 Alkenes (Chart l(iii))

2.8.4 Alkynes (Chart l(iv))

2.9 Carbonyl Compounds (Chart 2)

2.9.1 Aldehydes and ketones (including quinones) Chart 2(i))

2.9.2 Esters and lactones (Chart 2(ii))

2.9.3 Carboxylic acids and their salts (Chart 2(iii)) 77

2.9.4 Amino acids (Chart 2(iv))

2.9.5 Carboxylic acid anhydrides (Chart 2(v))

2.9.6 Amides (primary and N-substituted) (Chart 2(vi))

2.9.7 Acyl halides (Chart 2(vii))

2.10 Hydroxy Compounds and Ethers (Chart 3)

2.10.1 Alcohols (Chart 3(i))

2.lO.2 Carbohydrates (Chart 3(ii))

2.10.3 Phenols (Chart 3(iii))

2.10.4 Ethers (Chart 3(iv))

2.11 Nitrogen Compounds (Chart 4)

2.11.1 Amines (Chart 4(i))

2.11.2 Imines and aldehyde-ammonias (Chari 4(ii))

2.11.3 Nitro compounds (Chart 4(iii))

2.11.4 Nitriles and isonitriles (Chart 4(iv))

2.12 Halogen Compounds (Chart 5)

2.13 Sulfur and Phosphorus Compounds (Chart 6)

Supplement 2

25.1 Quantitative Infrared Analysis 88

2S.1.1 Absorbance 88

2S.1.2 Slit widths 90

2S.1.3 Path lengths .90

2S.1.4 Molar absorptivity 91

25.2 Attenuated Total Reflectance (ATR) and Multiple

Internal Reflectance (MIR) 92

25.3 Laser-Raman Spectroscopy 95

2S.3.1 The Raman effect 95

2S.3.2 Comparison of infrared and Raman spectra 96

Further Reading 98

3 Nuclear Magnetic Resonance Spectroscopy 101

Proton NMR Spectroscopy 104

3.1 The NMR Phenomenon 104

3.1.1 The spinning nucleus 104

3.1.2 The effect of an external magnetic field 104

3.1.3 Precessional motion 104

3.1.4 Precessional frequency 105

3.1.5 Energy transitions 106

3.2 Theory of Nuclear Magnetic Resonance 106

3.3 Chemical Shift and its Measurement 109

3.3.1 Measurement of chemical shift-internal standards 110

3.3.2 Measurement of chemical shift-the NMR

spectrometer 111

3.3.3 Measurement of chemical shift-units used in NMR

spectroscopy 116

3.4 Factors Influencing Chemical Shift 119

spectra-COSY 224

3S.3.4 Magnetic Resonance Imag ing (MRI) 227

35.4 Chemically Induced Dynam ic Nuclear Polarization

(CIDNP) 229

35.5 19F and 31p NMR 230

3S.5,1 1sF NMR 230

3S.5.2 31p NMR 232

x CONTENTS

35.6 14N, 15N and 170 NMR 233

3S.6.1 15N NMR 234

3S.6.2 170 NMR 235

35.7 Electron Spin Resonance Spectroscopy (ESR) 236

3S.7.1 Derivative curves 236

3S.7.2 9 values 237

3S.7.3 Hyperfine splitting 238

Further Reading 240

4 Ultraviolet and Visible Spectroscopy 243

4.1 Colour and Light Absorption-the Chromophore Concept 245

4.2 Theory of Electronic Spectroscopy 249

4.2.1 Orbitals involved in electronic transitions 249

4.2.2 Laws of light absorption-Beer’s and Lambert’s laws 251

4.2.3 Conventions 252

4.3 Instrumentation and Sampling 253

4.3.1 The ultraviolet-visible spectrometer-dispersive, photodiode ar￾ray and Fourier Transform Instruments 253

4.3.2 Sample and reference cells 256

4.3.3 Solvents and solutions 256

4.3.4 Vacuum ultraviolet 258

4.4 Solvent Effects 258

4.5 Applications of Electronic Spectroscopy-Conjugated Dienes,

Trienes and Polyenes 259

4.6 Applications of Electronic Spectroscopy-Conjugated Poly-ynes

and Eneynes 261

4.7 Applications of Electronic Spectroscopy-c-op-Unsaturated

Carbonyl Compounds 261

4.8 Applications of Electronic Spectroscopy-Benzene and its Substi￾tution Derivatives 263

4.9 Applications of Electronic Spectroscopy-Aromatic Hydrocarbons

other than Benzene 264

4.10 Applications of Electronic Spectroscopy-Heterocyclic

Systems 267

4.11 Stereochemical Factors in Electronic Spectroscopy 268

4.11 .1 Biphenyls and binaphthyls 268

cis and transisomers 268

Angular distortion and cross-conjugation. Steric inhibition of

resonance 269

Supplement 4 269

45.1 Quantitative Electronic Spectroscopy 269

45.2 Fluorescence and Phosphorescence 271

45.3 Absorption Spectra of Charge-transfer Complexes 274

45.4 Symmetry Restrictions on the Allowedness of Electronic

Transitions 276

45.5 Optical Rotatory Dispersion and Circular Dichroism 277

45.5.1 Definitions and nomenclature 277

45.5 .2 Cotton effect and stereochemistry 278

45.5 .3 The octant rule 279

45.6 Electron Spectroscopy for Chemical Analysis (ESCA) 280

Further Reading 282

5 Mass Spectrometry 285

5.1 Basic Principles 286

5.2 Instrumentation-the Mass Spectrometer 288

5.2 .1 Sample insertion-inlet systems 288

5.2.2 Ion production in the ionization chamber 289

5.2.3 Separation of the ions in the analyzer 290

5.2.4 The detector-recorder 292

5.2.5 Data handling 292

5.3 Isotope Abundances 293

5.4 The Molecular Ion 295

5.4.1 Structure of the molecular ion 295

5.4.2 Recognition of the molecular ion 297

5.4.3 Molecular formula from the molecular ion 298

5.5 Metastable Ions 299

5.5.1 The nature of metastable ions 299

5.5.2 Ion tube regions 300

5.5.3 Calculation of metastable ion m/z values 301

5.5.4 Significance of metastable ions 303

Appendix I Useful Data-Correlation Tables and Charts

Appendix 2 Acronyms in Spectroscopy

Index

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