Introduction to Spectroscopy,9780030319617

Introduction to Spectroscopy

by ; ;
Edition: 3rd
ISBN13: 9780030319617
ISBN10: 0030319617
Format: Paperback
Pub. Date: 2000-07-13
Publisher(s): Brooks Cole
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Summary

A true introductory text for learning the spectroscopic techniques of Nuclear Magnetic Resonance, Infrared, Ultraviolet and Mass Spectrometry. It can be used in a stand alone spectroscopy course or as a supplement to the sophomore-level organic chemistry course.

Table of Contents

Molecular Formulas and What Can be Learned from Them
1(12)
Elemental Analysis and Calculations
1(2)
Determination of Molecular Mass
3(1)
Molecular Formulas
4(1)
Index of Hydrogen Deficiency
4(3)
The Rule of Thirteen
7(3)
A Quick Look Ahead to Simple Uses of Mass Spectra
10(3)
Problems
11(1)
References
12(1)
Infrared Spectroscopy
13(89)
The Infrared Absorption Process
14(1)
Uses of the Infrared Spectrum
15(1)
The Modes of Stretching and Bending
16(2)
Bond Properties and Absorption Trends
18(2)
The Infrared Spectrometer
20(3)
Dispersive Infrared Spectrometers
20(3)
Fourier Transform Spectrometers
23(1)
Preparation of Samples for Infrared Spectroscopy
23(1)
What To Look for When Examining Infrared Spectra
24(3)
Correlation Charts and Tables
27(1)
How to Approach the Analysis of a Spectrum (Or What You Can Tell at a Glance)
28(1)
Hydrocarbons: Alkanes, Alkenes, and Alkynes
29(12)
Alkanes
29(2)
Alkenes
31(2)
Alkynes
33(8)
Aromatic Rings
41(4)
Alcohols and Phenols
45(3)
Ethers
48(2)
Carbonyl Compounds
50(22)
Factors That Influence the C = O Stretching Vibration
52(2)
Aldehydes
54(2)
Ketones
56(4)
Carboxylic Acids
60(2)
Esters
62(6)
Amides
68(2)
Acid Chlorides
70(1)
Anhydrides
71(1)
Amines
72(3)
Nitriles, Isocyanates, Isothiocyanates, and Imines
75(2)
Nitro Compounds
77(1)
Carboxylate Salts, Amine Salts, and Amino Acids
78(1)
Sulfur Compounds
79(3)
Phosphorus Compounds
82(1)
Alkyl and Aryl Halides
82(20)
Problems
84(17)
References
101(1)
Nuclear Magnetic Resonance Spectroscopy
PART ONE: BASIC CONCEPTS 102(65)
Nuclear Spin States
102(1)
Nuclear Magnetic Moments
103(1)
Absorption of Energy
104(2)
The Mechanism of Absorption (Resonance)
106(2)
Population Densities of Nuclear Spin States
108(1)
The Chemical Shift and Shielding
109(2)
The Nuclear Magnetic Resonance Spectrometer
111(6)
The Continuous-Wave (CW) Instrument
111(2)
The Pulsed Fourier Transform (FT) Instrument
113(4)
Chemical Equivalence---A Brief Overview
117(1)
Integrals and Integration
118(2)
Chemical Environment and Chemical Shift
120(1)
Local Diamagnetic Shielding
121(4)
Electronegativity Effects
121(2)
Hybridization Effects
123(1)
Acidic and Exchangeable Protons: Hydrogen Bonding
124(1)
Magnetic Anisotropy
125(3)
Spin-Spin Splitting (n + 1) Rule
128(3)
The Origin of Spin-Spin Splitting
131(2)
The Ethyl Group (CH3CH2--)
133(1)
Pascal's Triangle
134(1)
The Coupling Constant
134(3)
A Comparison of NMR Spectra at Low and High Field Strengths
137(1)
Survey of Typical 1H NMR Absorptions by Type of Compound
138(29)
Alkanes
139(1)
Alkenes
140(1)
Aromatic Compounds
140(2)
Alkynes
142(1)
Alkyl Halides
143(1)
Alcohols
144(1)
Ethers
145(1)
Amines
146(1)
Nitriles
147(1)
Aldehydes
148(1)
Ketones
149(1)
Esters
150(1)
Carboxylic Acids
150(2)
Amides
152(1)
Nitroalkanes
153(1)
Problems
154(12)
References
166(1)
Nuclear Magnetic Resonance Spectroscopy
PART TWO: CARBON-13 SPECTRA, INCLUDING HETERONUCLEAR COUPLING WITH OTHER NUCLEI 167(50)
The Carbon-13 Nucleus
167(1)
Carbon-13 Chemical Shifts
168(3)
Correlation Charts
168(2)
Calculation of 13C Chemical Shifts
170(1)
Proton-Coupled 13C Spectra---Spin-Spin Splitting of Carbon-13 Signals
171(2)
Proton-Decoupled 13C Spectra
173(1)
Nuclear Overhauser Enhancement (NOE)
174(2)
Cross-Polarization: Origin of the Nuclear Overhauser Effect
176(3)
Problems with Integration in 13C Spectra
179(1)
Molecular Relaxation Processes
180(2)
Off-Resonance Decoupling
182(1)
A Quick Dip into DEPT
182(3)
Some Sample Spectra---Equivalent Carbons
185(2)
Compounds with Aromatic Rings
187(2)
Carbon-13 NMR Solvents---Heteronuclear Coupling of Carbon to Deuterium
189(4)
Heteronuclear Coupling of Carbon to Fluorine-19
193(1)
Heteronuclear Coupling of Carbon to Phosphorus-31
194(23)
Problems
195(21)
References
216(1)
Nuclear Magnetic Resonance Spectroscopy
PART THREE: SPIN-SPIN COUPLING 217(89)
Coupling Constants: Symbols
217(1)
Coupling Constants: The Mechanism of Coupling
218(10)
One-Bond Couplings (1J)
219(1)
Two-Bond Couplings (2J)
220(3)
Three-Bond Couplings (3J)
223(4)
Long-Range Couplings (4J--nJ)
227(1)
Magnetic Equivalence
228(3)
Nonequivalence Within a Group---The Use of Tree Diagrams when the n + 1 Rule Fails
231(3)
Measuring Coupling Constants from First Order Spectra
234(3)
Simple Multiplets---One Value of J (One Coupling)
234(1)
More Complex Multiplets---More Than One Value of J
235(2)
Alkenes
237(1)
Mechanisms of Coupling in Alkenes; Allylic Coupling
238(3)
Measuring Coupling Constants---Analysis of an Allylic System
241(5)
Is the n + 1 Rule Ever Really Obeyed?
246(1)
Second-Order Spectra---Strong Coupling
247(8)
First-Order and Second-Order Spectra
247(1)
Spin System Notation
248(1)
The A2, AB, and AX Spin Systems
248(3)
The AB2 ... AX2 and A2B2 ... A2X2 Spin Systems
251(3)
Simulation of Spectra
254(1)
The Absence of Second-Order Effects at Higher Field
254(1)
Deceptively Simple Spectra
255(1)
Some Other Patterns
255(1)
Aromatic Compounds---Substituted Benzene Rings
255(9)
Monosubstituted Rings
256(3)
para-Disubstituted Rings
259(2)
Other Substitution
261(3)
Coupling in Heteroaromatic Systems
264(1)
Long-Range Coupling
265(3)
Homotopic, Enantiotopic, and Diastereotopic Systems
268(2)
Spectra of Diastereotopic Systems
270(36)
Diastereotopic Methyl Groups: (S)-(+)-3-Methyl-2-butanol
270(3)
Diastereotopic Hydrogens: 1,2-Dichloropropane
273(1)
Diastereotopic Fluorines: 1-Bromo-2-chloro-1,1,2-trifluoroethane
273(2)
Problems
275(29)
References
304(2)
Nuclear Magnetic Resonance Spectroscopy
PART FOUR: OTHER TOPICS IN ONE-DIMENSIONAL NMR 306(220)
Protons on Oxygen: Alcohols
306(3)
Exchange in Water and D2O
309(3)
Acid/Water and Alcohol/Water Mixtures
309(1)
Deuterium Exchange
310(1)
Peak Broadening Due to Exchange
311(1)
Other Types of Exchange: Tautomerism
312(2)
Protons on Nitrogen: Amines
314(4)
Protons on Nitrogen: Quadrupole Broadening and Decoupling
318(1)
Amides
319(3)
The Effect of Solvent on Chemical Shift
322(1)
Chemical Shift Reagents; High-Field Spectra
323(3)
Chiral Resolving Agents
326(1)
Spin Decoupling Methods; Double Resonance
326(3)
NOE Difference Spectra
329(24)
Problems
332(20)
References
352(1)
Ultraviolet Spectroscopy
353(37)
The Nature of Electronic Excitations
353(2)
The Origin of UV Band Structure
355(1)
Principles of Absorption Spectroscopy
355(1)
Instrumentation
356(1)
Presentation of Spectra
357(1)
Solvents
358(1)
What is a Chromophore?
359(3)
The Effect of Conjugation
362(1)
The Effect of Conjugation on Alkenes
363(3)
The Woodward-Fieser Rules for Dienes
366(3)
Carbonyl Compounds: Enones
369(3)
Woodward's Rules for Enones
372(2)
α ,β-Unsaturated Aldehydes, Acids, and Esters
374(1)
Aromatic Compounds
374(9)
Substituents with Unshared Electrons
376(2)
Substituents Capable of π-Conjugation
378(1)
Electron-Releasing and Electron-Withdrawing Effects
378(1)
Disubstituted Benzene Derivatives
378(3)
Polynuclear Aromatic Hydrocarbons and Heterocyclic Compounds
381(2)
Model Compound Studies
383(1)
Visible Spectra: Color in Compounds
384(1)
What To Look for in an Ultraviolet Spectrum: A Practical Guide
385(5)
Problems
387(2)
References
389(1)
Mass Spectrometry
390(76)
The Mass Spectrometer
390(3)
Gas Chromatography-Mass Spectrometry
393(1)
The Mass Spectrum
394(3)
Determination of Molecular Weight
397(2)
Determination of Molecular Formulas
399(5)
Precise Mass Determination
399(1)
Isotope Ratio Data
400(4)
Some Fragmentation Patterns
404(41)
Alkanes
405(3)
Cycloalkanes
408(2)
Alkenes
410(2)
Alkynes
412(1)
Aromatic Hydrocarbons
413(4)
Alcohols and Phenols
417(5)
Ethers
422(1)
Aldehydes
423(2)
Ketones
425(3)
Esters
428(3)
Carboxylic Acids
431(2)
Amines
433(4)
Selected Nitrogen and Sulfur Compounds
437(4)
Alkyl Chlorides and Alkyl Bromides
441(4)
Additional Topics
445(1)
Computerized Matching of Spectra with Spectral Libraries
446(20)
Problems
448(17)
References
465(1)
Combined Structure Problems
466(60)
Example 1
468(2)
Example 2
470(2)
Example 3
472(4)
Example 4
476(2)
Problems
478(47)
Sources of Additional Problems
525(1)
Nuclear Magnetic Resonance Spectroscopy
PART FIVE: ADVANCED NMR TECHNIQUES 526
Pulse Sequences
526(2)
Pulse Widths, Spins, and Magnetization Vectors
528(4)
The DEPT Experiment
532(4)
Determining the Number of Attached Hydrogens
536(4)
Methine Carbons (CH)
536(1)
Methylene Carbons (CH2)
537(2)
Methyl Carbons (CH3)
539(1)
Quaternary Carbons (C)
539(1)
The Final Result
540(1)
Introduction to Two-Dimensional Spectroscopic Methods
540(1)
The COSY Technique
540(5)
An Overview of the COSY Experiment
541(1)
How To Read COSY Spectra
542(3)
The HETCOR Technique
545(5)
An Overview of the HETCOR Experiment
546(1)
How To Read HETCOR Spectra
546(4)
Magnetic Resonance Imaging
550
Problems
552(27)
References
579
ANSWERS TO SELECTED PROBLEMS 1(1)
APPENDICES
Appendix 1 Infrared Absorption Frequencies of Functional Groups
2(6)
Appendix 2 Approximate 1H Chemical Shift Ranges (ppm) for Selected Types of Protons
8(1)
Appendix 3 Some Representative 1H Chemical Shift Values for Various Types of Protons
9(3)
Appendix 4 1H Chemical Shifts of Selected Heterocyclic and Polycyclic Aromatic Compounds
12(1)
Appendix 5 Typical Proton Coupling Constants
13(4)
Appendix 6 Calculation of Proton (1H) Chemical Shifts
17(4)
Appendix 7 Approximate 13C Chemical Shift Ranges (ppm) for Selected Types of Carbon
21(1)
Appendix 8 Calculation of 13C Chemical Shifts
22(9)
Appendix 9 13C Coupling Constants
31(1)
Appendix 10 1H and 13C Chemical Shifts for Common NMR Solvents
32(1)
Appendix 11 Tables of Precise Masses and Isotopic Abundance Ratios for Molecular Ions Under Mass 100 Containing Carbon, Hydrogen, Nitrogen, and Oxygen
33(6)
Appendix 12 Common Fragment Ions Under Mass 105
39(3)
Appendix 13 Handy-Dandy Guide to Mass Spectral Fragmentation Patterns
42(3)
Appendix 14 Index of Spectra
45
Index 1

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