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Organic Structural Spectroscopy

ISBN: 9780132586900 | 0132586908
Edition: 1st
Format: Hardcover
Publisher: Prentice Hall
Pub. Date: 1/1/1998

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SummaryTable of Contents
Appropriate for courses in organic spectroscopy or organic spectroscopic techniques in senior undergraduate and graduate programs. This text authoritatively covers currently used techniques for determining the structure of organic and biological compoundsideal for any practicing or future organic or biochemist. The fundamentals of all four principal spectroscopic methods are covered in depth, each by an experienced author who is a practicing expert in that area. The material is easy to grasp, beginning at the most elementary level and progressi... MORE
Prefacevii
1 Introduction
1(7)
1-1 The Spectroscopic Approach to Structure
1(1)
... MORE
1-2 Contributions of Different Forms of Spectroscopy
1(2)
1-2a Nuclear Magnetic Resonance Spectroscopy
1(1)
1-2b Vibrational Spectroscopy
2(1)
1-2c Electronic Spectroscopy
2(1)
1-2d Mass Spectrometry
3(1)
1-3 The Electromagnetic Spectrum
3(1)
1-4 Molecular Weight and Molecular Formula
4(2)
1-5 Structural Isomers and Stereoisomers, 5 Problems
6(2)
PART I NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY8(144)
2 Introduction and Experimental Methods
8(29)
2-1 Magnetic Properties of Nuclei
8(3)
2-2 The Chemical Shift
11(3)
2-3 Excitation and Relaxation
14(2)
2-4 Pulsed Experiments
16(2)
2-5 The Coupling Constant
18(5)
2-6 Quantitation
23(2)
2-7 Commonly Studied Nuclides
25(2)
2-8 Experimental Methods
27(3)
2-8a The Spectrometer and the Sample
27(1)
2-8b Optimizing the Signal
28(1)
2-8c Spectral Parameters
28(2)
2-9 Dynamic Effects
30(2)
2-10 Spectra of Solids
32(2)
Problems
34(2)
Bibliography
36(1)
3 The Chemical Shift
37(27)
3-1 Factors That Influence Proton Shifts
37(4)
3-2 Proton Chemical Shifts and Structure
41(6)
3-2a Saturated Aliphatics
41(2)
3-2b Unsaturated Aliphatics
43(2)
3-2c Aromatics
45(1)
3-2d Protons on Oxygen and Nitrogen
46(1)
3-3 Factors That Influence Carbon Shifts
47(2)
3-4 Carbon Chemical Shifts and Structure
49(6)
3-4a Saturated Aliphatics
49(4)
3-4b Unsaturated Compounds
53(1)
3-4c Carbonyl Groups
54(1)
3-5 Summary and Tables of Chemical Shifts
55(2)
Problems
57(6)
Bibliography
63(1)
4 The Coupling Constant
64(25)
4-1 First- and Second-Order Spectra
64(1)
4-2 Chemical and Magnetic Equivalence
65(3)
4-3 Signs and Mechanisms: One Bond Couplings
68(2)
4-4 Geminal Couplings
70(2)
4-5 Vicinal Couplings
72(2)
4-6 Long-Range Couplings
74(1)
4-7 Spectral Analysis
75(4)
4-8 Tables of Coupling Constants
79(3)
Problems
82(6)
Bibliography
88(1)
5 Further Topics in One-Dimensional NMR
89(28)
5-1 Spin-Lattice and Spin-Spin Relaxation
89(5)
5-2 Reactions on the NMR Time Scale
94(2)
5-3 Multiple Resonance
96(5)
5-4 The Nuclear Overhauser Effect
101(4)
5-5 Spectral Editing
105(2)
5-6 Sensitivity Enhancement
107(3)
5-7 Carbon Connectivity
110(2)
5-8 Phase Cycling and Composite Pulses
112(2)
Problems
114(1)
Bibliography
115(2)
6 Two-Dimensional NMR
117(35)
6-1 Proton-Proton Correlation Through Coupling
117(4)
6-2 Proton-Heteronucleus Correlation
131(4)
6-3 Proton-Proton Correlation Through Space or Chemical Exchange
135(3)
6-4 Carbon-Carbon Correlation
138(2)
6-5 Higher Dimensions
140(2)
6-6 Pulsed Field Gradients
142(2)
6-7 Summary of Two-Dimensional Methods
144(1)
Problems
145(5)
Bibliography
150(2)
PART II VIBRATIONAL SPECTROSCOPY152(100)
7 Introduction and Experimental Methods
152(23)
7-1 Introduction
152(1)
7-2 Vibrations of Molecules
153(1)
7-3 Vibrational Spectra: Infrared and Raman
154(3)
7-4 Units and Notation
157(1)
7-5 Infrared Spectroscopy: Dispersive and Fourier Transform
158(4)
7-5a Dispersive Infrared Spectrometers
158(1)
7-5b Fourier Transform Infrared Spectrometers
159(3)
7-6 Sampling Methods for Infrared Transmission Spectra
162(3)
7-6a Liquids and Solutions
163(1)
7-6b Solids
164(1)
7-7 Raman Spectroscopy: Dispersive and Fourier Transform
165(2)
7-7a Dispersive Raman Spectrometers
166(1)
7-7b FT-Raman Spectrometers
167(1)
7-8 Raman Sampling Methods
167(3)
7-8a Liquids and Solutions
168(1)
7-8b Solids
169(1)
7-8c Depolarization Measurements
170(1)
7-9 Special Techniques in Infrared Spectroscopy
170(4)
7-9a Gas Phase Infrared Spectroscopy
170(1)
7-9b Microsampling
171(1)
7-9c Infrared Reflection Spectroscopy
171(2)
7-9d Gas Chromatography and Infrared Spectroscopy (GC-IR)
173(1)
Problems
174(1)
Bibliography
174(1)
8 Group Frequencies: Infrared and Raman
175(26)
8-1 Introduction to Group Frequencies
175(1)
8-2 Factors Affecting Group Frequencies
176(11)
8-2a Symmetry
177(2)
8-2b Mechanical Coupling of Vibrations
179(1)
8-2c Fermi Resonance
180(1)
8-2d Hydrogen Bonding
181(1)
8-2e Ring Strain
182(1)
8-2f Electronic Effects
183(1)
8-2g Constitutional Isomerism
184(1)
8-2h Stereoisomerism
185(1)
8-2i Conformational Isomerism
186(1)
8-2j Tautomerism (Dynamic Isomerism)
187(1)
8-3 Infrared Group Frequencies
187(1)
8-4 Raman Group Frequencies
188(11)
Problems
199(1)
Bibliography
200(1)
9 Structural Analysis
201(51)
9-1 Introduction
201(1)
9-2 Preliminary Analysis
202(6)
9-2a Introduction
202(1)
9-2b Hydrocarbons or Hydrocarbon Groups
203(1)
9-2c Compounds Containing Oxygen
204(3)
9-2d Compounds Containing Nitrogen
207(1)
9-3 The CH Stretching Region (3340-2700 cm(-1))
208(3)
9-3a Introduction
208(1)
9-3b Alkynes
208(1)
9-3c Aromatic Compounds
208(1)
9-3d Unsaturated Nonaromatic Compounds
209(1)
9-3e Saturated Hydrocarbon Groups
210(1)
9-3f Aldehydes
210(1)
9-4 The Carbonyl Stretching Region (1850-1650 cm(-1))
211(3)
9-4a Introduction
211(3)
9-4b Compounds Containing a Single C = O Group
211(2)
9-4c Compounds Containing Two C = O Groups
213(1)
9-5 Aromatic Compounds
214(2)
9-5a General
214(1)
9-5b Substituted Aromatic Compounds
214(1)
9-5c Raman Spectra of Aromatic Compounds
215(1)
9-6 Compounds Containing Methyl Groups
216(2)
9-6a General
216(1)
9-6b Isopropyl and tert-Butyl Groups
217(1)
9-7 Compounds Containing Methylene Groups
218(1)
9-7a Introduction
218(1)
9-7b CH(2) Bending (Scissoring)
218(1)
9-7c CH(2) Wagging and Twisting
218(1)
9-7d CH(2) Rocking
219(1)
9-7e CH(2) Wagging in Vinyl and Vinylidene Compounds
219(1)
9-7f Relative Numbers of CH(2) and CH(3) Groups
219(1)
9-8 Unsaturated Compounds
219(4)
9-8a The C = C Stretching Mode
219(1)
9-8b Cyclic Compounds
219(1)
9-8c The C = C Stretching Mode
220(1)
9-8d CH = and CH(2) = Bending Modes
220(3)
9-9 Compounds Containing Oxygen
223(3)
9-9a General
223(1)
9-9b Ethers
224(1)
9-9c Alcohols and Phenols
224(2)
9-9d Carboxylic Acids and Anhydrides
226(1)
9-9e Esters
226(1)
9-10 Compounds Containing Nitrogen
226(5)
9-10a General
226(1)
9-10b Amino Acids, Amines, and Amine Hydrohalides
226(3)
9-10c Anilines
229(1)
9-10d Nitriles
229(1)
9-10e Nitro Compounds
230(1)
9-10f Amides
230(1)
9-10g Oximes
230(1)
9-11 Compounds Containing Phosphorus and Sulfur
231(4)
9-11a General
231(1)
9-11b Phosphorus Acids and Esters
231(1)
9-11c Aromatic Phosphorus Compounds
231(1)
9-11d Compounds Containing C-S, S-S, and S-H Groups
232(1)
9-11e Compounds Containing S=O Groups
233(2)
9-12 Heterocyclic Compounds
235(2)
9-12a General
235(2)
9-12b Aromatic Heterocycles
237(1)
9-12c Pyrimidines and Purines
236(1)
9-12d Five-Membered Ring Compounds
236(1)
9-12e NH Stretching Bands
236(1)
9-13 Compounds Containing Halogens
237(1)
9-13a General
237(1)
9-13b CH(2)X Groups
238(1)
9-13c Haloalkyl Groups
238(1)
9-13d Aromatic Halogen Compounds
238(1)
9-14 Boron, Silicon, and Organometallic Compounds
238(1)
9-15 Isotopically Labeled Compounds
239(1)
9-15a The Effect of (2)H and (13)C Isotopic Substitution on Stretching Modes
239(1)
9-15b The Effect of Deuterium Substitution on Bending Modes
239(1)
9-16 Using the Literature on Vibrational Spectra
240(2)
9-16a Collections of Spectra
240(1)
9-16b Infrared Spectra
241(1)
9-16c Raman Spectra
241(1)
9-16d Sources of References to Published Spectra
242(1)
Problems
242(8)
Bibliography
250(2)
PART III ELECTRONIC ABSORPTION AND CHIROPTICAL SPECTROSCOPY252(94)
10 Introduction and Experimental Methods
252(22)
10-1 Introduction
252(2)
10-2 Measurement of Ultraviolet-Visible Light Absorption
254(4)
10-2a Wavelength and XXX(max')
255(1)
10-2b Beer-Bouger-Lambert Law and XXX(max')
255(1)
10-2c Shape of Absorption Curves: The Franck-Condon Principle
256(1)
10-2d Solvent Effects and XXX(max) Shifts
257(1)
10-3 Measurements Using Polarized Light
258(8)
10-3a Ordinary Absorption and Chiroptical Spectroscopy
261(1)
10-3b Circular Birefringence and Circular Dichroism
261(2)
10-3c Optical Rotatory Dispersion (ORD) and Circular Dichroism (CD) Quantities
263(1)
10-3d ORD and CD Spectra and Cotton Effects
264(2)
10-3e Relative Advantages of ORD and CD
266(1)
10-4 Quantitative Measurements
266(3)
10-4a Difference Spectroscopy
266(2)
10-4b Deviations From Beer's Law
268(1)
10-4c Isosbestic Points
268(1)
10-5 Experimental Aspects
269(3)
10-5a Solvents
269(1)
10-5b Cells (Cuvettes) and Sample Preparation
269(2)
10-5c Calibration of ORD and CD Instruments
271(1)
10-5d Possible Sources of Error
271(1)
Problems
272(1)
Bibliography
273(1)
11 UV-Vis, CD, and ORD
274(30)
11-1 Electronic Transitions and Chromophores
274(5)
11-1a Classification of Electronic Transitions
275(2)
11-1b Singlet and Triplet States
277(1)
11-1c Allowed and Forbidden Transitions
277(1)
11-1d Absorption Intensity: Oscillator and Rotatory Strengths
278(1)
11-2 Isolated Chromophores
279(6)
11-2a Carbonyl: Ketone and Aldehyde Absorption
279(2)
11-2b Carbonyl: Ketone ORD and CD
281(1)
11-2c Carbonyl: Acid, Ester, and Amide Absorption
281(2)
11-2d Alkenes
283(2)
11-3 Conjugated Chromophores
285(2)
11-3a Dienes and Polyenes
285(1)
11-3b XXX, XXX-Unsaturated Carbonyls
286(1)
11-4 Aromatic Compounds
287(5)
11-5 Important Naturally Occurring Chromophores
292(7)
11-5a Amino Acids, Peptides, and Proteins
292(4)
11-5b Nucleic Acids and Polynucleotides
296(1)
11-5c Porphyrins and Metalloporphyrins
296(3)
11-6 Worked Problems
299(2)
Problems
301(2)
Bibliography
303(1)
12 Structural Analysis
304(42)
12-1 Applications of the Woodward-Fieser Rules
304(5)
12-1a Conjugated Dienes and Polyenes
304(3)
12-1b Conjugated Ketones, Aldehydes, Acids, and Esters
307(2)
12-2 Determination of Absolute Configuration
309(8)
12-2a The Octant Rule
309(3)
12-2b Exciton Coupling and the Exciton Chirality Rule
312(5)
12-3 Steric Effects
317(1)
12-4 Solvent Effects and Tautomerism
318(2)
12-5 Conformational Analysis
320(2)
12-6 Hydrogen Bonding Studies
322(1)
12-7 Homoconjugation
323(2)
12-8 Charge Transfer Bands
325(2)
12-9 Worked Problems
327(10)
Problems
337(7)
Bibliography
344(2)
PART IV MASS SPECTROMETRY346(133)
13 Ionization and Mass Analysis
346(46)
13-1 Scope and Applications of Mass Spectrometry
346(2)
13-2 Sample Introduction
348(2)
13-2a Direct Introduction
349(1)
13-2b Introduction via Gas or Liquid Chromatographs
349(1)
13-2c Other Sample Introduction Methods
350(1)
13-3 Ionization
350(24)
13-3a Electron Ionization (EI)
351(4)
13-3b Chemical Ionization (CI)
355(7)
13-3c Desorption Ionization (DI) Including Matrix-Assisted Laser Desorption Ionization (MALDI)
362(7)
13-3d Spray Ionization (SI) Including Electrospray Ionization (ESI)
369(5)
13-3e Ionization Summary
374(1)
13-4 Mass Analysis
374(12)
13-4a Magnetic Sectors
374(2)
13-4b Time-of-Flight(TOF) Analyzers
376(1)
13-4c Quadrupole Mass Filters
377(2)
13-4d Quadrupole Ion Traps
379(1)
13-4e Ion Cyclotron Resonance (ICR)
380(2)
13-4f High Resolution Mass Spectrometers
382(1)
13-4g Tandem Mass Spectrometers
382(2)
13-4h Ion Detection and Data Handling
384(2)
13-5 Worked Problems
386(3)
Problems
389(1)
Bibliography
390(2)
14 Fragmentation and Ion Chemistry
392(46)
14-1 General Principles of Fragmentation
392(5)
14-1a Energetics of Dissociation
392(1)
14-1b Odd- and Even-Electron Ions
393(1)
14-1c Stevenson's Rule
394(1)
14-1d Rearrangement vs. Simple Cleavage
394(1)
14-1e Ions of High Internal Energy
395(1)
14-1f Proximate vs. Remote Fragmentation
395(1)
14-1g Distonic Ions
396(1)
14-1h Charge Localization
396(1)
14-1i Characteristic Fragment Ions and Neutral Fragments
396(1)
14-2 Amine and Ether Type Fragmentation
397(13)
14-2a Amines
397(4)
14-2b Ethers
401(5)
14-2c Alcohols and Phenols
406(4)
14-2d Halides
410(1)
14-3 Ketone and Aldehyde Type Fragmentation
410(4)
14-4 Fragmentation of Other Functional Groups
414(3)
14-4a Carboxylic Acids
414(1)
14-4b Esters
414(3)
14-4c Amides
417(1)
14-4d Aliphatic Hydrocarbons
417(1)
14-4e Aromatic Hydrocarbons
417(1)
14-5 Negative Ion Fragmentation
417(2)
14-6 Fragmentation in CI, DI, and SI
419(2)
14-7 Ion Chemistry
421(11)
14-7a Unimolecular Fragmentation
421(5)
14-7b Ion-Molecule Reactions
426(3)
14-7c Advanced Ion Chemistry
429(3)
14-8 Worked Problems
432(4)
Problems
436(1)
Bibliography
437(1)
15 Chemical Analysis
438(35)
15-1 Molecular Weight Determination
438(1)
15-2 Molecular Structure Determination
439(2)
15-3 Molecular Formula Determination (Exact Mass Measurement)
441(1)
15-4 Isotopic Analysis
442(7)
15-4a Recognition of Elements: Isotopic Signatures
442(1)
15-4b Number of Carbon Atoms in a Molecule
442(1)
15-4c Calculation of Ion Abundance Ratios From the Molecular Formula
443(1)
15-4d Typical Molecular Ion Isotopic Profiles for Organic and Biological Compounds
444(2)
15-4e Determination of Molecular Formula From Isotopic Abundances
446(1)
15-4f Isotopic Purity Determination
447(2)
15-5 Quantitative Analysis
449(1)
15-6 Mixture Analysis
450(5)
15-6a Chromatography-Mass Spectrometry
450(2)
15-6b Tandem Mass Spectrometry (MS-MS)
452(3)
15-7 Thermochemical Determinations: Heats of Formation and Ion Affinities
455(1)
15-8 Other Applications of Mass Spectrometry
456(2)
15-8a Industrial Applications and Process Control
456(1)
15-8b Isotope Ratio Mass Spectrometry
456(1)
15-8c Elemental Analysis
457(1)
15-8d Surface Elemental Analysis
457(1)
15-9 Worked Problems
458(9)
Problems
467(5)
Bibliography
472(1)
Appendix to Part IV
473(6)
PART V INTEGRATED PROBLEMS479(78)
16 Integrated Problems
480(77)
Index557

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