Structure Determination of Organic Compounds

by Pretsch, Erno; Buhlmann, P.; Affolter, C.

• ISBN13: 9783540678151
• ISBN10: 3540678158
• Edition: 3rd
• Format: Paperback
• Copyright: 2000-10-01
• Publisher: SPRINGER - VERLAG

Summary

This volume presents in the form of texts, tables, charts and graphs a modern compilation of spectroscopic reference data for IR, UV/Vis, 1H- and 13C-NMR, MS (incl. prototype spectra of almost every important class of organic compounds and spectra of MALDI and FAB matrix materials) and is intended as a short textbook and a hands-on guide for interpreting experimental spectral data and elucidating the chemical structure of the respective compound behind it. The concise texts include special chapters on fragmentation rules in mass spectrometry and on currently used multipulse and 2-D NMR techniques. The book is primarily designed for students to be used during courses and exercises. The use of the book requires only basic knowledge of spectroscopic techniques, but is structured in such a way that it will support practitioners routinely faced with the task of interpreting such spectral information, and it will serve as data reference for specialists in the fields.

Table of Contents

Introduction	1	(4)
Scope and Organization	1	(2)
Abbreviations and Symbols	3	(2)
Summary Tables	5	(44)
General Tables	5	(2)
Calculation of the Number of Double Bond Equivalents from the Molecular Formula	5	(1)
Properties of Selected Nuclei	6	(1)
13C NMR Spectroscopy	7	(3)
1H NMR Spectroscopy	10	(3)
IR Spectroscopy	13	(5)
Mass Spectrometry	18	(29)
Average Masses of Naturally Occurring Elements with Exact Masses and Representative Relative Abundances of Isotopes	18	(6)
Ranges of Natural Isotope Abundances of Selected Elements	24	(1)
Isotope Patterns of Naturally Occurring Elements	25	(1)
Calculation of Isotope Distributions	26	(2)
Isotopic Abundances of Various Combinations of Chlorine, Bromine, Sulfur, and Silicon	28	(2)
Isotope Patterns of Combinations of Cl and Br	30	(1)
Indicators of the Presence of Heteratoms	31	(2)
Rules for Determining the Relative Molecular Weight (Mr)	33	(1)
Homologous Mass Series as Indications of Structural Type	34	(2)
Mass Correlation Table	36	(10)
References	46	(1)
UV/Vis Spectroscopy	47	(2)
Combination Tables	49	(22)
Alkanes, Cycloalkanes	49	(1)
Alkenes, Cycloalkenes	50	(1)
Alkynes	51	(1)
Aromatic Hydrocarbons	52	(1)
Heteroaromatic Compounds	53	(1)
Halogen Compounds	54	(2)
Oxygen Compounds	56	(3)
Alcohols and Phenols	56	(1)
Ethers	57	(2)
Nitrogen Compounds	59	(3)
Amines	59	(1)
Nitro Compounds	60	(2)
Thiols and Sulfides	62	(1)
Carbonyl Compounds	63	(8)
Aldehydes	63	(1)
Ketones	64	(1)
Carboxylic Acids	65	(1)
Carboxylic Esters and Lactones	66	(2)
Carboxylic Amides and Lactams	68	(3)
13C NMR Spectroscopy	71	(90)
Alkanes	71	(11)
Chemical Shifts	71	(9)
Coupling Constants	80	(1)
References	81	(1)
Alkenes	82	(6)
Chemical Shifts	82	(4)
Coupling Constants	86	(1)
References	87	(1)
Alkynes	88	(2)
Chemical Shifts	88	(1)
Coupling Constants	89	(1)
References	89	(1)
Alicyclics	90	(6)
Chemical Shifts	90	(5)
Coupling Constants	95	(1)
References	95	(1)
Aromatic Hydrocarbons	96	(8)
Chemical Shifts	96	(6)
Coupling Constants	102	(1)
References	103	(1)
Heteroaromatic Compounds	104	(8)
Chemical Shifts	104	(7)
Coupling Constants	111	(1)
Halogen Compounds	112	(5)
Fluoro Compounds	112	(2)
Chloro Compounds	114	(1)
Bromo Compounds	115	(1)
Iodo Compounds	116	(1)
References	116	(1)
Alcohols, Ethers, and Related Compounds	117	(4)
Alcohols	117	(2)
Ethers	119	(2)
Nitrogen Compounds	121	(7)
Amines	121	(2)
Nitro and Nitroso Compounds	123	(1)
Nitrosamines	124	(1)
Imines and Oximes	124	(1)
Hydrazones and Carbodiimides	125	(1)
Nitriles and Isonitriles	126	(1)
Isocyanates, Thiocyanates and Isothiocyanates	127	(1)
References	127	(1)
Sulfur-Containing Functional Groups	128	(5)
Thiols	128	(1)
Sulfides	128	(2)
Disulfides and Sulfonium Salts	130	(1)
Sulfoxides and Sulfones	130	(1)
Sulfonic and Sulfinic Acids and Derivatives	131	(1)
Sulfurous and Sulfuric Acid Derivatives	131	(1)
Sulfur-Containing Carbonyl Derivatives	132	(1)
Carbonyl Compounds	133	(11)
Aldehydes	133	(1)
Ketones	134	(2)
Carboxylic Acids and Carboxylates	136	(2)
Esters and Lactones	138	(2)
Amides and Lactams	140	(2)
Miscellaneous Carbonyl Derivatives	142	(2)
Miscellaneous Compounds	144	(4)
Derivatives of Group IV Elements	144	(1)
Phosphorus Compounds	145	(2)
Miscellaneous Organometallic Compounds	147	(1)
Natural Products	148	(9)
Amino Acids	148	(4)
Carbohydrates	152	(2)
Nucleotides and Nucleosides	154	(2)
Steroids	156	(1)
Spectra of Solvents and References Compounds	157	(4)
13C NMR Spectra of Common Deuterated Solvents	157	(2)
13C NMR Spectra of Secondary Reference Compounds	159	(1)
13C NMR Spectra of a Mixture of Common Nondeuterated Solvents	160	(1)
1H NMR Spectroscopy	161	(84)
Alkanes	161	(7)
Chemical Shifts	161	(5)
Coupling Constants	166	(1)
References	167	(1)
Alkenes	168	(7)
Substituted Ethylenes	168	(6)
Dienes	174	(1)
Alkynes	175	(1)
Chemical Shifts and Coupling Constants	175	(1)
Alicyclics	176	(4)
Aromatic Hydrocarbons	180	(6)
Heteroaromatic Compounds	186	(12)
Non-Condensed Heteroaromatic Rings	186	(7)
Condensed Heteroaromatic Rings	193	(5)
Halogen Compounds	198	(4)
Fluoro Compounds	198	(1)
Chloro Compounds	199	(1)
Bromo Compounds	200	(1)
Iodo Compounds	201	(1)
Alcohols, Ethers, and Related Compounds	202	(5)
Alcohols	202	(2)
Ethers	204	(3)
Nitrogen Compounds	207	(7)
Amines	207	(3)
Nitro and Nitroso Compounds	210	(1)
Nitrosamines, Azo, and Azoxy Compounds	210	(1)
Imines, Oximes, Hydrazones, and Azines	211	(1)
Nitriles and Isonitriles	212	(1)
Cyanates, Isocyanates, Thiocyanates, and Isothiocyanates	213	(1)
Sulfur-Containing Functional Groups	214	(4)
Thiols	214	(1)
Sulfides	215	(1)
Disulfides and Sulfonium Salts	216	(1)
Sulfoxides and Sulfones	216	(1)
Sulfonic, Sulfinic, Sulfurous, and Sulfuric Acids and Derivatives	217	(1)
Thiocarboxylate Derivatives	217	(1)
Carbonyl Compounds	218	(10)
Aldehydes	218	(1)
Ketones	219	(1)
Carboxylic Acids and Carboxylates	220	(1)
Esters and Lactones	221	(2)
Amides and Lactams	223	(3)
Miscellaneous Carbonyl Derivatives	226	(2)
Miscellaneous Compounds	228	(5)
Silicon Compounds	228	(1)
Phosphorus Compounds	229	(3)
Miscellaneous Compounds	232	(1)
Natural Products	233	(7)
Amino Acids	233	(3)
Carbohydrates	236	(1)
Nucleotides and Nucleosides	237	(2)
References	239	(1)
Spectra of Solvents and References Compounds	240	(5)
1H NMR Spectra of Common Deuterated Solvents	240	(2)
1H NMR Spectra of Secondary Reference Compounds	242	(1)
1H NMR Spectrum of a Mixture of Common Nondeuterated Solvents	243	(2)
IR Spectroscopy	245	(68)
Alkanes	245	(3)
Alkenes	248	(4)
Monoenes	248	(3)
Allenes	251	(1)
Alkynes	252	(1)
Alicyclics	253	(2)
Aromatic Hydrocarbons	255	(3)
Heteroaromatic Compounds	258	(2)
Halogen Compounds	260	(3)
Fluoro Compounds	260	(1)
Chloro Compounds	261	(1)
Bromo Compounds	262	(1)
Iodo Compounds	262	(1)
Alcohols, Ethers, and Related Compounds	263	(5)
Alcohols and Phenols	263	(1)
Ethers, Acetals, Ketals	264	(2)
Epoxides	266	(1)
Peroxides and Hydroperoxides	267	(1)
Nitrogen Compounds	268	(12)
Amines and Related Compounds	268	(2)
Nitro and Nitroso Compounds	270	(2)
Imines and Oximes	272	(2)
Azo Compounds	274	(1)
Nitriles and Isonitriles	275	(1)
Diazo Compounds	276	(1)
Cyanates and Isocyanates	277	(1)
Thiocyanates and Isothiocyanates	278	(2)
Sulfur-Containing Functional Groups	280	(6)
Thiols and Sulfides	280	(1)
Sulfoxides and Sulfones	281	(2)
Thiocarbonyl Derivatives	283	(1)
Thiocarbonic Acid Derivatives	283	(3)
Carbonyl Compounds	286	(18)
Aldehydes	286	(1)
Ketones	287	(3)
Carboxylic Acids	290	(2)
Esters and Lactones	292	(3)
Amides and Lactames	295	(3)
Acid Anhydrides	298	(2)
Acid Halides	300	(1)
Carbonic Acid Derivatives	301	(3)
Miscellaneous Compounds	304	(5)
Silicon Compounds	304	(1)
Phosphorus Compounds	305	(3)
Boron Compounds	308	(1)
Amino Acids	309	(1)
Solvents, Suspension Media, and Interferences	310	(3)
Infrared Spectra of Common Solvents	310	(1)
Infrared Spectra of Suspension Media	311	(1)
Interferences in Infrared Spectra	312	(1)
Mass Spectrometry	313	(72)
Alkanes	313	(2)
Unbranched Alkanes	313	(1)
Branched Alkanes	313	(1)
References	314	(1)
Alkenes	315	(2)
Unbranched Alkenes	15	(300)
Branched Alkenes	315	(1)
Polyenes and Polyynes	316	(1)
References	316	(1)
Alkynes	317	(1)
Aliphatic Alkynes	317	(1)
References	317	(1)
Alicyclic Hydrocarbons	318	(3)
Cyclopropanes	318	(1)
Saturated Monocyclic Alicyclics	319	(1)
Polycyclic Alicyclics	319	(1)
Cyclohexenes	319	(1)
References	320	(1)
Aromatic Hydrocarbones	321	(2)
Aromatic Hydrocarbons	321	(1)
Alkylsubstituted Aromatic Hydrocarbons	321	(1)
References	322	(1)
Heteroaromatic Compounds	323	(5)
General Characteristics	323	(1)
Furans	323	(1)
Thiophenes	323	(1)
Pyrroles	324	(1)
Pyridines	324	(1)
N-Oxides of Pyridines and Quinolines	325	(1)
Pyridazines and Pyrimidines	325	(1)
Pyrazines	326	(1)
Indoles	326	(1)
Quinolines	326	(1)
Cinnoline	327	(1)
References	327	(1)
Halogen	328	(2)
Saturated Aliphatic Halides	328	(1)
Polyhaloalkanes	329	(1)
Aromatic Halides	329	(1)
References	329	(1)
Alcohols	330	(9)
Aliphatic Alcohols	330	(1)
Alicyclic Alcohols	331	(1)
Unsaturated Aliphatic Alcohols	331	(1)
Vicinal Glycols	331	(1)
Aliphatic Hydroperoxides	332	(1)
Phenols	332	(1)
Benzyl	332	(1)
Aliphatic Ethers	333	(1)
Unsaturated Ethers	334	(1)
Alkyl Cycloalkyl Ethers	335	(1)
Cyclic Ethers	335	(1)
Aliphatic Epoxides	336	(1)
Methoxybenzenes	337	(1)
Alkyl Aryl Ethers	337	(1)
Aromatic Ethers	337	(1)
Aliphatic Peroxides	337	(1)
References	338	(1)
Nitrogen Compounds	339	(10)
Saturated Aliphatic Amines	339	(1)
Cycloalkylamines	339	(1)
Cyclic Amines	340	(1)
Piperazines	341	(1)
Aromatic Amines	341	(1)
Aliphatic Nitro Compounds	341	(1)
Aromatic Nitro Compounds	342	(1)
Diazo	342	(1)
Azobenzenes	342	(1)
Aliphatic Azides	342	(1)
Aromatic Azides	343	(1)
Aliphatic Nitriles	343	(1)
Aromatic Nitriles	344	(1)
Aliphatic Isonitriles (R--NC)	344	(1)
Aromatic Isonitriles (R--NC)	344	(1)
Aliphatic Cyanates (R--OCN)	345	(1)
Aromatic Cyanates (R--OCN)	345	(1)
Aliphatic Isocyanates (R--NCO)	345	(1)
Aromatic Isocyanates (R--NCO)	346	(1)
Aliphatic Thiocyanates (R--SCN)	346	(1)
Aromatic Thiocyanates (R--SCN)	347	(1)
Aliphatic Isothiocyanates (R--NCS)	347	(1)
Aromatic Isothiocyanates (R--NCS)	347	(1)
References	348	(1)
Sulfur-Containing Functional Groups	349	(9)
Aliphatic Thiols	349	(1)
Aromatic Thiols	349	(1)
Aliphatic Sulfides	350	(1)
Alkyl Vinyl Sulfides	350	(1)
Cyclic Sulfides	351	(1)
Aromatic Sulfides	351	(1)
Disulfides	351	(1)
Aliphatic Sulfoxides	352	(1)
Alkyl Aryl and Diaryl Sulfoxides	352	(1)
Aliphatic Sulfones	353	(1)
Cyclic Sulfones	354	(1)
Alkyl Aryl Sulfones	354	(1)
Diaryl Sulfones	355	(1)
Aromatic Sulfonic Acids	355	(1)
Alkylsulfonic Acid Esters	355	(1)
Arylsulfonic Acid Esters	356	(1)
Aromatic Sulfonamides	356	(1)
Thiocarboxylic Acid S-Esters	357	(1)
References	357	(1)
Carbonyl Compounds	358	(11)
Aliphatic Aldehydes	358	(1)
Unsaturated Aliphatic Aldehydes	358	(1)
Aromatic Aldehydes	358	(1)
Aliphatic Ketones	359	(1)
Unsaturated Ketones	359	(1)
Alicyclic Ketones	359	(1)
Aromatic Ketones	360	(1)
Aliphatic Carboxylic Acids	360	(1)
Aromatic Carboxylic Acids	361	(1)
Carboxylic Acid Anhydrides	361	(1)
Saturated Aliphatic Esters	361	(1)
Unsaturated Esters	362	(1)
Esters of Aromatic Acids	363	(1)
Lactones	364	(1)
Aliphatic Amides	364	(1)
Amides of Aromatic Carboxylic Acids	365	(1)
Anilides	365	(1)
Lactams	365	(2)
Imides	367	(1)
References	368	(1)
Miscellaneous Compounds	369	(2)
Trialkylsilyl Ethers	369	(1)
Alkyl Phosphates	369	(1)
Aliphatic Phosphines	369	(1)
Aromatic Phosphines and Phosphine Oxides	370	(1)
References	370	(1)
Mass Spectra of Common Solvents and Matrix Compounds	371	(14)
Electron Impact Ionization Mass Spectra of Common Solvents	371	(3)
Spectra of Common FAB MS Matrix and Calibration Compounds	374	(6)
Spectra of Common MALDI MS Matrix Compounds	380	(3)
References	383	(2)
UV/Vis Spectroscopy	385	(21)
Correlation Between Wavelength of Absorbed Radiation and Observed Color	385	(1)
UV/Vis Absorption of Simple Chromophores	385	(2)
UV/Vis Absorption of Conjugated Alkenes	387	(3)
UV Absorption of Dienes and Polyenes	387	(1)
UV Absorption of α,β-Unsaturated Carbonyl Compounds	388	(2)
UV/Vis Absorption of Aromatic Compounds	390	(3)
UV Absorption of Monosubstituted Benzenes	390	(1)
UV Absorption of Substituted Benzenes	391	(1)
UV Absorption of Aromatic Carbonyl Compounds	392	(1)
UV/Vis Reference Spectra	393	(11)
UV/Vis Spectra of Alkenes and Alkynes	393	(1)
UV/Vis Spectra of Aromatic Compounds	394	(5)
UV/Vis Spectra of Heteroaromatic Compounds	399	(2)
UV/Vis Spectra of Miscellaneous Compounds	401	(2)
UV/Vis Spectra of Nucleotides	403	(1)
UV/Vis Absorption of Common Solvents	404	(2)
Subject Index	406