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Spectrometric Identification of Organic Compounds

Spectrometric Identification of Organic Compounds

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CHAPTER 1 MASS SPECTROMETRY 1

1.1 Introduction 1

1.2 Instrumentation 2

1.3 Ionization Methods 3

1.3.1 Gas-Phase Ionization Methods 3

1.3.1.1 Electron Impact Ionization 3

1.3.1.2 Chemical Ionization 3

1.3.2 Desorption Ionization Methods 4

1.3.2.1 Field Desorption Ionization 4

1.3.2.2 Fast Atom Bombardment Ionization 4

1.3.2.3 Plasma Desorption Ionization 5

1.3.2.4 Laser Desorption Ionization 6

1.3.3 Evaporative Ionization Methods 6

1.3.3.1 Thermospray Mass Spectrometry 6

1.3.3.2 Electrospray Mass Spectrometry 6

1.4 Mass Analyzers 8

1.4.1 Magnetic Sector Mass Spectrometers 8

1.4.2 Quadrupole Mass Spectrometers 9

1.4.3 Ion Trap Mass Spectrometer 10

1.4.4 Time-of-Flight Mass Spectrometer 11

1.4.5 Fourier Transform Mass Spectrometer 12

1.4.6 Tandem Mass Spectrometry 12

1.5 Interpretation of EI Mass Spectra 12

1.5.1 Recognition of the Molecular Ion Peak 13

1.5.2 Determination of a Molecular Formula 14

1.5.2.1 Unit-Mass Molecular Ion and Isotope Peaks 14

1.5.2.2 High-Resolution Molecular Ion 15

1.5.3 Use of the Molecular Formula. Index of Hydrogen Deficiency 15

1.5.4 Fragmentation 16

1.5.5 Rearrangements 18

1.6 Mass Spectra of Some Chemical Classes 18

1.6.1 Hydrocarbons 18

1.6.1.1 Saturated Hydrocarbons 18

1.6.1.2 Alkenes (Olefins) 19

1.6.1.3 Aromatic and Aralkyl Hydrocarbons 21

1.6.2 Hydroxy Compounds 22

1.6.2.1 Alcohols 22

1.6.2.2 Phenols 23

1.6.3 Ethers 24

1.6.3.1 Aliphatic Ethers (and Acetals) 24

1.6.3.2 Aromatic Ethers 25

1.6.4 Ketones 261.6.4.1 Aliphatic Ketones 26

1.6.4.2 Cyclic Ketones 26

1.6.4.3 Aromatic Ketones 26

1.6.5 Aldehydes 28

1.6.5.1 Aliphatic Aldehydes 28

1.6.5.2 Aromatic Aldehydes 28

1.6.6 Carboxylic Acids 28

1.6.6.1 Aliphatic Acids 28

1.6.6.2 Aromatic Acids 29

1.6.7 Carboxylic Esters 29

1.6.7.1 Aliphatic Esters 29

1.6.7.2 Benzyl and Phenyl Esters 30

1.6.7.3 Esters of Aromatic Acids 30

1.6.8 Lactones 31

1.6.9 Amines 31

1.6.9.1 Aliphatic Amines 31

1.6.9.2 Cyclic Amines 32

1.6.9.3 Aromatic Amines (Anilines) 32

1.6.10 Amides 32

1.6.10.1 Aliphatic Amides 32

1.6.10.2 Aromatic Amides 32

1.6.11 Aliphatic Nitriles 32

1.6.12 Nitro Compounds 33

1.6.12.1 Aliphatic Nitro Compounds 33

1.6.12.2 Aromatic Nitro Compounds 33

1.6.13 Aliphatic Nitrites 33

1.6.14 Aliphatic Nitrates 33

1.6.15 Sulfur Compounds 33

1.6.15.1 Aliphatic Mercaptans (Thiols) 33

1.6.15.2 Aliphatic Sulfides 34

1.6.15.3 Aliphatic Disulfides 34

1.6.16 Halogen Compounds 35

1.6.16.1 Aliphatic Chlorides 35

1.6.16.2 Aliphatic Bromides 35

1.6.16.3 Aliphatic Iodides 35

1.6.16.4 Aliphatic Fluorides 36

1.6.16.5 Benzyl Halides 37

1.6.16.6 Aromatic Halides 37

1.6.17 Heteroaromatic Compounds 37

References 37

Student Exercises 37

Appendices 46

A Formula Masses (FM) for Various Combinations of Carbon, Hydrogen, Nitrogen, and Oxygen 46

B Common Fragment Ions 67

C Common Fragments Lost 69

CHAPTER 2 INFRARED SPECTROSCOPY 71

2.1 Introduction 71

2.2 Theory 71

2.2.1 Coupled Interactions 74

2.2.2 Hydrogen Bonding 75

2.3 Instrumentation 76

2.3.1 Dispersion IR 76

2.3.2 Fourier Transform Infrared Spectrometer (Interferometer) 76

2.4 Sample Handling 77

2.5 Interpretation of Spectra 78

2.6 Characteristic Group Absorptions of Organic Molecules 81

2.6.1 Normal Alkanes (Paraffins) 81

2.6.1.1 C H Stretching Vibrations 81

2.6.1.2 C H Bending Vibrations 81

2.6.2 Branched-Chain Alkanes 82

2.6.2.1 C H Stretching Vibrations: Tertiary C H Groups 82

2.6.2.2 C H Bending Vibrations: gem-Dimethyl Groups 82

2.6.3 Cyclic Alkanes 83

2.6.3.1 C H Stretching Vibrations 83

2.6.3.2 C H Bending Vibrations 83

2.6.4 Alkenes 83

2.6.4.1 C C Stretching Vibrations Unconjugated Linear Alkenes 83

2.6.4.2 Alkene C H Stretching Vibrations 84

2.6.4.3 Alkene C H Bending Vibrations 84

2.6.5 Alkynes 8
First published over 40 years ago, this was the first text on the identification of organic compounds using spectroscopy. This text is now considered to be a classic. This text presents a unified approach to the structure determination of organic compounds based largely on mass spectrometry, infrared (IR) spectroscopy, and multinuclear and multidimensional nuclear magnetic resonance (NMR) spectroscopy. The key strength of this text is the extensive set of practice and real-data problems (in Chapters 7 and 8). Even professional chemists use these spectra as reference data. Spectrometric Identification of Organic Compounds is written by and for organic chemists, and emphasizes the synergistic effect resulting from the interplay of the spectra. This book is characterized by its problem-solving approach with extensive reference charts and tables.The 8th edition of this text maintains its student-friendly writing style - wording throughout has been updated for consistency and to be more reflective of modern usage and methods. Chapter 3 on proton NMR spectroscopy has been overhauled and updated. Also, new information on polymers and phosphorus functional groups has been added to Chapter 2 on IR spectroscopy.

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Produktdetails

Autor: Robert M. Silverstein
ISBN-13: 9780470616376
ISBN: 0470616377
Einband: Taschenbuch
Seiten: 464
Gewicht: 891 g
Format: 279x215x20 mm
Sprache: Englisch
Autor: Robert M. Silverstein, Francis X. Webster, David J. Kiemle
InhaltsangabeChapter 1 Mass Spectrometry Chapter 2 Infrared Spectroscopy Chapter 3 Proton (1H) Magnetic Resonance Spectroscopy Chapter 4 Carbon-13 NMR Spectroscopy Chapter 5 Two-Dimensional NMR Spectroscopy Chapter 6 Multinuclear Magnetic Resonance Spectroscopy Chapter 7 Solved Problems Chapter 8 Assigned Problems

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Autor: Robert M. Silverstein
ISBN-13:: 9780470616376
ISBN: 0470616377
Erscheinungsjahr: 29.09.2014
Verlag: PAPERBACKSHOP UK IMPORT
Gewicht: 891g
Seiten: 464
Sprache: Englisch
Auflage 00008, Revised
Sonstiges: Taschenbuch, 279x215x20 mm