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Spectrometric Identification of Organic Compounds, 7th Edition,9780471393627
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Summary

Originally published in 1962, this was the first book to explore teh identification of organic compounds using spectroscopy. It provides a thorough introduction to the three areas of spectrometry most widely used in spectrometric identification: mass spectrometry, infrared spectrometry, and nuclear magnetic resonance spectrometry. A how-to, hands-on teaching manual with considerably expanded NMR coverage--NMR spectra can now be intrepreted in exquisite detail. This book: * Uses a problem-solving approach with extensive reference charts and tables. * Offers an extensive set of real-data problems offers a challenge to the practicing chemist

Table of Contents

Mass Spectrometry
1(71)
Introduction
1(1)
Instrumentation
2(1)
Ionization Methods
3(5)
Gas-Phase Ionization Methods
3(1)
Electron Impact Ionization
3(1)
Chemical Ionization
3(1)
Desorption Ionization Methods
4(1)
Field Desorption Ionization
4(1)
Fast Atom Bombardment Ionization
4(1)
Plasma Desorption Ionization
5(1)
Laser Desorption Ionization
6(1)
Evaporative Ionization Methods
6(1)
Thermospray Mass Spectrometry
6(1)
Electrospray Mass Spectrometry
6(2)
Mass Analyzers
8(5)
Magnetic Spector Mass Spectrometers
9(1)
Quadrupole Mass Spectrometers
10(1)
Ion Trap Mass Spectrometers
10(2)
Time-of-Flight Mass Spectrometer
12(1)
Fourier Transform Mass Spectrometer
12(1)
Tandem Mass Spectrometry
12(1)
Interpretation of El Mass Spectra
13(6)
Recognition of the Molecular Ion Peak
14(1)
Determination of a Molecular Formula
14(1)
Unit-Mass Molecular Ion and Isotope Peaks
14(1)
High-Resolution Molecular Ion
15(1)
Use of the Molecular Formula. Index of Hydrogen Deficiency
16(1)
Fragmentation
17(2)
Rearrangements
19(1)
Mass Spectra of Some Chemical Classes
19(53)
Hydrocarbons
19(1)
Saturated Hydrocarbons
19(1)
Alkenes (Olefins)
20(1)
Aromatic and Aralkyl Hydrocarbons
21(1)
Hydroxy Compounds
22(1)
Alcohols
22(2)
Phenols
24(1)
Ethers
24(1)
Aliphatic Ethers (and Acetals)
24(1)
Aromatic Ethers
25(1)
Ketones
26(1)
Aliphatic Ketones
26(1)
Cyclic Ketones
26(1)
Aromatic Ketones
27(1)
Aldehydes
27(1)
Aliphatic Aldehydes
27(1)
Aromatic Aldehydes
28(1)
Carboxylic Acids
28(1)
Aliphatic Acids
28(1)
Aromatic Acids
28(1)
Carboxylic Esters
29(1)
Aliphatic Esters
29(1)
Benzyl and Phenyl Esters
30(1)
Esters of Aromatic Acids
30(1)
Lactones
31(1)
Amines
31(1)
Aliphatic Amines
31(1)
Cyclic Amines
32(1)
Aromatic Amines (Anilines)
32(1)
Amides
32(1)
Aliphatic Amides
32(1)
Aromatic Amides
32(1)
Aliphatic Nitriles
32(1)
Nitro Compounds
33(1)
Aliphatic Nitro Compounds
33(1)
Aromatic Nitro Compounds
33(1)
Aliphatic Nitrites
33(1)
Aliphatic Nitrates
33(1)
Sulfur Compounds
33(1)
Aliphatic Mercaptans (Thiols)
34(1)
Aliphatic Sulfides
34(1)
Aliphatic Disulfides
35(1)
Halogen Compounds
35(1)
Aliphatic Chlorides
36(1)
Aliphatic Bromides
37(1)
Aliphatic Iodides
37(1)
Aliphatic Fluorides
37(1)
Benzyl Halides
37(1)
Aromatic Halides
37(1)
Heteroaromatic Compounds
37(1)
References
38(1)
Student Exercises
39(8)
Appendices
47(1)
Formulas Masses
47(21)
Common Fragment Ions
68(2)
Common Fragments Lost
70(2)
Infrared Spectrometry
72(55)
Introduction
72(1)
Theory
72(6)
Coupled Interaction
75(1)
Hydrogen Bonding
76(2)
Instrumentation
78(1)
Dispersion IR Spectrometer
78(1)
Fourier Transform Infrared Spectrometer (Interferometer)
78(1)
Sample Handling
79(1)
Interpretations of Spectra
80(2)
Characteristic Group Absorption of Organic Molecules
82(45)
Normal Alkanes (Paraffins)
82(1)
C---H Stretching Vibrations
83(1)
C---H Bending Vibrations Methyl Groups
83(1)
Branched-Chain Alkanes
84(1)
C---H Stretching Vibrations Tertiary C---H Groups
84(1)
C---H Bending Vibrations gem-Dimethyl Groups
84(1)
Cyclic Alkanes
85(1)
C---H Stretching Vibrations
85(1)
C---H Bending Vibrations
85(1)
Alkenes
85(1)
C---C Stretching Vibrations Unconjugated Linear Alkenes
85(1)
Alkene C---H Stretching Vibrations
86(1)
Alkene C---H Bending Vibrations
86(1)
Alkynes
86(1)
C---C Stretching Vibrations
86(1)
C---H Stretching Vibrations
87(1)
C---H Bending Vibrations
87(1)
Mononuclear Aromatic Hydrocarbons
87(1)
Out-of-Plane C---H Bending Vibrations
87(1)
Polynuclear Aromatic Hydrocarbons
87(1)
Alcohols and Phenols
88(1)
O---H Stretching Vibrations
88(1)
C---O Stretching Vibrations
89(1)
O---H Bending Vibrations
90(1)
Ethers, Epoxides, and Peroxides
91(1)
C---O Stretching Vibrations
91(1)
Ketones
92(1)
C---O Stretching Vibrations
92(2)
C---C(=O)---C Stretching and Bending Vibrations
94(1)
Aldehydes
94(1)
C---O Stretching Vibrations
94(1)
C---H Stretching Vibrations
94(1)
Carboxylic Acids
95(1)
O---H Stretching Vibrations
95(1)
C=O Stretching Vibrations
95(1)
C---O Stretching and O---H Bending Vibrations
96(1)
Carboxylate Anion
96(1)
Esters and Lactones
96(1)
C=O Stretching Vibrations
97(1)
C---O Stretching Vibrations
98(1)
Acid Halides
98(1)
C=O Stretching Vibrations
98(1)
Carboxylic Acid Anhydrides
98(1)
C=O Stretching Vibrations
98(1)
C---O Stretching Vibrations
98(1)
Amides and Lactams
99(1)
N---H Stretching Vibrations
99(1)
C=O Stretching Vibrations (Amide I Band)
100(1)
N---H Bending Vibrations (Amide II Band)
100(1)
Other Vibration Bands
101(1)
C=O Stretching Vibrations of Lactams
101(1)
Amines
101(1)
N---H Stretching Vibrations
101(1)
N---H Bending Vibrations
101(1)
C---N Stretching Vibrations
102(1)
Amine Salts
102(1)
N---H Stretching Vibrations
102(1)
N---H Bending Vibrations
102(1)
Amino Acids and Salts of Amino Acids
102(1)
Nitriles
103(1)
Isonitriles (R---N=C), Cyanates (R---O---C=N), Isocyanates (R---N=C=O), Thiocyanates (R---S---C=N), Isothiocyanates (R---N=C=S)
104(1)
Compounds Containing---N=N
104(1)
Covalent Compounds Containing Nitrogen-Oxygen Bonds
104(1)
N=O Stretching Vibrations Nitro Compounds
104(1)
Organic Sulfur Compounds
105(1)
S=H Stretching Vibrations Mercaptans
105(1)
C---S and C=S Stretching Vibrations
106(1)
Compounds Containing Sulfur---Oxygen Bonds
106(1)
S=O Stretching Vibrations Sulfoxides
106(1)
Organic Halogen Compounds
107(1)
Silicon Compounds
107(1)
Si---H Vibrations
107(1)
SiO---H and Si---O Vibrations
107(1)
Silicon---Halogen Stretching Vibrations
107(1)
Phosphorus Compounds
107(1)
P=O and P---O Stretching Vibrations
107(1)
Heteroaromatic Compounds
107(1)
C---H Stretching Vibrations
107(1)
N---H Stretching Frequencies
108(1)
Ring Stretching Vibrations (Skeletal Bands)
108(1)
C---H Out-of-Plane Bending
108(1)
References
108(2)
Student Exercises
110(9)
Appendices
119(1)
Transparent Regions of Solvents and Mulling Oils
119(1)
Characteristic Group Absorptions
120(5)
Absorptions for Alkenes
125(1)
Absorptions for Phosphorus Compounds
126(1)
Absorptions for Heteroaromatics
126(1)
Proton Magnetic Resonance Spectrometry
127(77)
Introduction
127(1)
Theory
127(8)
Magnetic Properties of Nuclei
127(1)
Excitation of Spin 1/2 Nuclei
128(2)
Relaxation
130(5)
Instrumentation and Sample Handling
135(2)
Instrumentation
135(1)
Sensitivity of NMR Experiments
136(1)
Solvent Selection
137(1)
Chemical Shift
137(6)
Spin Coupling, Multiplets, Spin Systems
143(17)
Simple and Complex First Order Multiplets
145(1)
First Order Spin Systems
146(1)
Pople Notions
147(1)
Further Examples of Simple, First-Order Spin Systems
147(1)
Analysis of First-Order Patterns
148(12)
Protons on Oxygen, Nitrogen, and Sulfur Atoms. Exchangeable Protons
160
Protons on an Oxygen Atom
150(1)
Alcohols
150(3)
Water
153(1)
Phenols
153(1)
Enols
153(1)
Carboxylic Acids
153(1)
Protons on Nitrogen
153(2)
Protons on Sulfur
155(1)
Protons on or near Chlorine, Bromine, or Iodine Nuclei
155(1)
Coupling of Protons to Other Important Nuclei (19F, D, 31P, 29Si, and 13C)
155(2)
Coupling of Protons to 19F
155(1)
Coupling of Protons to D
155(1)
Coupling of Protons to 31P
156(1)
Coupling of Protons to 29Si
156(1)
Coupling of Protons to 13C
156(1)
Chemical Shift Equivalence
157(5)
Determination of Chemical Shift Equivalence by Interchange Through Symmetry Operations
157(1)
Interchange by Rotation Around a Simple Axis of Symmetry (Cn)
157(1)
Interchange by Reflection Through a Plane of Symmetry (σ)
157(1)
Interchange by Inversion Through a Center of Symmetry (i)
158(1)
No Interchangeability by a Symmetry Operations
158(1)
Determination of Chemical Shift Equivalence by Tagging (or Substitution)
159(1)
Chemical Shift Equivalence by Rapid Interconversion of Structures
160(1)
Keto-Enol Interconversion
160(1)
Interconversion Around a ``Partial Double Bond'' (Restricted Rotation)
160(1)
Interconversion Around the Single Bond of Rings
160(1)
Interconversion Around the Single Bonds of Chains
161(1)
Magnetic Equivalence (Spin-Coupling Equivalence)
162(2)
AMX, ABX, and ABC Rigid Systems with Three Coupling Constants
164(1)
Confirmationally Mobile, Open-Chain Systems. Virtual Coupling
165(4)
Unsymmetrical Chains
165(1)
1-Nitropropane
165(1)
1-Hexanol
165(2)
Symmetrical Chains
167(1)
Dimethyl Succinate
167(1)
Dimethyl Glutarate
167(1)
Dimethyl Adipate
167(1)
Dimethyl Pimelate
168(1)
Less Symmetrical Chains
168(1)
3-Methylglutaric Acid
168(1)
Chirality
169(2)
One Chiral Center, Ipsenol
169(2)
Two Chiral Centers
171(1)
Vicinal and Geminal Coupling
171(1)
Low-Range Coupling
172(1)
Selective Spin Decoupling. Double Resonance
173(1)
Nuclear Overhauser Effect, Difference Spectrometry, 1H 1H Proximity Through Space
173(2)
Conclusion
175(29)
References
176(1)
Student Exercises
177(11)
Appendices
188(1)
Chemicals Shifts of a Proton
188(3)
Effect on Chemical Shifts by Two or Three Directly Attached Functional Groups
191(2)
Chemical Shifts in Alicyclic and Heterocyclic Rings
193(1)
Chemical Shifts in Unsaturated and Aromatic Systems
194(3)
Protons on Heteroatoms
197(1)
Proton Spin-Coupling Constants
198(2)
Chemical Shifts and Multiplicities of Residual Protons in Commercially Available Deuterated Solvents
200(1)
1H NMR Data
201(2)
Proton NMR Chemical Shifts of Amino Acids in D2O
203(1)
Carbon-13 NMR Spectrometry
204(41)
Introduction
204(1)
Theory
204(7)
1H Decoupling Techniques
204(1)
Chemical Shift Scale and Range
205(1)
T1 Relaxation
206(1)
Nuclear Overhauser Enhancement (NOE)
207(2)
13C---1H Sping Coupling (J Values)
209(1)
Sensitivity
210(1)
Solvents
210(1)
Interpretation of a Simple 13C Spectrum: Diethyl Phthalate
211(2)
Quantitative 13C Analysis
213(1)
Chemical Shift Equivalence
214(1)
DEPT
215(2)
Chemical Classes and Chemical Shifts
217(28)
Alkanes
218(1)
Linear and Branched Alkanes
218(1)
Effect of Substituents on Alkenes
218(2)
Cycloalkanes and Saturated Heterocyclics
220(1)
Alkenes
220(1)
Alkynes
221(1)
Aromatic Compounds
222(1)
Heteroaromatic Compounds
223(1)
Alcohols
223(2)
Ethers, Acetals, and Epoxides
225(1)
Halides
225(1)
Amines
226(1)
Thiols, Sulfides, and Disulfides
226(1)
Functional Groups Containing Carbon
226(1)
Ketones and Aldehydes
227(1)
Carboxylic Acids, Esters, Chlorides, Anhydrides, Amides, and Nitriles
227(1)
Oximes
227(1)
References
228(1)
Student Exercises
229(11)
Appendices
240(1)
The 13C Chemical Shifts, Couplings and Multiplicities of Common NMR Solvents
240(1)
13C Chemical Shift for Common Organic Compounds in Different Solvents
241(1)
The 13C Correlation Chart for Chemical Classes
242(2)
13C NMR Data for Several Natural Products (δ)
244(1)
Correlation NMR Spectrometry; 2-D NMR
245(71)
Introduction
245(1)
Theory
246(3)
Correlation Spectrometry
249(2)
1H---1H Correlation: COSY
250(1)
Ipsenol: 1H---1H COSY
251(8)
Ipsenol: Double Quantum Filtered 1H---1H COSY
251(3)
Carbon Detected 13C---1H COSY: Hector
254(1)
Proton Detected 1H---13C COSY: HMQC
254(1)
Ipsenol: Hector and HMQC
255(2)
Ipsenol: Proton-Detected, Long Range 1H---13C Heteronuclear Correlation: HMBC
257(2)
Caryophyllene Oxide
259(6)
Caryophyllene Oxide: DQF-COSY
259(1)
Caryophyllene Oxide: HMQC
259(4)
Caryophyllene Oxide: HMBC
263(2)
13C---13C Correlations: Inadequate
265(2)
Inadequate: Caryophyllene Oxide
266(1)
Lactose
267(3)
DQF-COSY: Lactose
267(3)
HMQC: Lactose
270(1)
HMBC: Lactose
270(1)
Relayed Coherence Transfer: TOCSY
270(5)
2-D TOCSY: Lactose
270(3)
1-D TOCSY: Lactose
273(2)
HMQC -- TOCSY
275(1)
HMQC -- TOCSY: Lactose
275(1)
Roesy
275(3)
Roesy: Lactose
275(3)
VGSE
278(4)
COSY: VGSE
278(1)
TOCSY: VGSE
278(1)
HMQC: VGSE
278(3)
HMBC: VGSE
281(1)
ROESY: VGSE
282(1)
Gradient Field NMR
282(34)
References
285(1)
Student Exercises
285(31)
NMR Spectrometry of Other Important Spin 1/2 Nuclei
316(25)
Introduction
316(1)
15N Nuclear Magnetic Resonance
317(6)
19F Nuclear Magnetic Resonance
323(3)
29Si Nuclear Magnetic Resonance
326(1)
31P Nuclear Magnetic Resonance
327(3)
Conclusion
330(11)
References
332(1)
Student Exercises
333(5)
Appendices
338(1)
Properties of Magnetically Active Nuclei
338(3)
Solved Problems
341(40)
Introduction
341(40)
Problem 7.1 Discussion
345(4)
Problem 7.2 Discussion
349(4)
Problem 7.3 Discussion
353(7)
Problem 7.4 Discussion
360(7)
Problem 7.5 Discussion
367(6)
Problem 7.6 Discussion
373(1)
Student Exercises
374(7)
Assigned Problems
381
Introduction
381
Problems
382


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