Structure Determination of Organic Compounds
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1 Structure Determination of Organic Compounds
2 Springer-Verlag Berlin Heidelberg GmbH
3 E. Pretsch, P. Biihlmann, C.Affolter Structure Determination of Organic Compounds Tables of Spectral Data Third Completely Revised and Enlarged English Edition Corrected first Printing, Springer
4 Professor Emoe Pretsch ETHZurich Laboratory of Organic Organie Chemistry CH-8092 Zurich Switzerland Dr. Philippe Biihlmann Bühlmann Department of Chemistry School of Science The University oftokyo Hongo7-3-1, Bunkyo-Ku Tokyo Japan Dr. Christian Affolter Aengerich8 CH-3303 Muenchringen Switzerland ISBN CIP-Data applied for Pretsch, Pretseh, Ernoe: Emoe: Structure Strueture determination of organic eompounds compounds: : tables of spectral speetral data I E. Pretsch Prel.eh ; P. Blihlmann Bühlmann ; C. Affolter. Affoller. - 3., eomplelely completely rev. and en\. eng\. ed.. ISBN ISBN (ebook) DOI / This work is subject subjeet to copyright. All rights are reserved, whether the whole or part of the material is eoneemed, concerned, specifically speeifieally the rights oftranslation, reprinting, reuse of illustrations, recitation, reeitation, broadcasting, broadeasting, reproduction reproduetion on microfilm mierofilm or in other ways, and storage in data banks. Duplication Duplieation of this publication publieation or parts thereof is permitted only under the provisions ofthe German Copyright Law of September 9, 1965, in its eurrent current version, and permission for use must always be obtained from Springer-Verlag Berlin Heidelberg GmbH. Violations are!iable liable for prosecution act aet under German Copyright Law. Springer-Verlag Berlin Heidelberg 2000 Originally published by Springer-Verlag Berlin Heidelberg New York in 2000 Softcover reprint of the hardcover 3rd edition 2000 Additional material to this book bock can be downloaded from The use of general descriptive deseriptive names, registered names, trademarks, etc. ete. in this publication publieation does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective proteetive laws and regulations and therefore free for general use. Typesetting: Camera-ready by editors Cover layout: design & production produetion GmbH, Heidelberg Printed on acid-free aeid-free paper SPIN: / I -
5 Preface While modem techniques of nuclear magnetic resonance and mass spectrometry changed the ways of data acquisition and greatly extended the capabilities of these methods, the basic parameters, such as chemical shifts, coupling constants, and fragmentation pathways remain the same. This explains the ongoing success of the earlier editions of this book. However, since the amount of available data has considerably increased over the years, we decided to prepare an entirely new manuscript. It follows the same basic concepts, i.e., it provides a representative, albeit limited set of reference data for the interpretation of 13C NMR, 1 H NMR, IR, mass, and UV Nis spectra. On the other hand, the book has undergone a number of changes. The amount of reference data has been doubled at least (especially for MS and IR) and the order and selection of data for the various spectroscopic methods is now arranged strictly in the same way. In addition, the the enclosed compact disc contains programs for estimating NMR chemical shifts and generating isomers based on structural information. Unfortunately, our teachers and colleagues, Prof. Wilhelm Simon and Prof. Thomas Clerc are no longer among us, and Prof. Joseph Seibl has retired years ago. Their contributions to developing the concept and the earlier editions of this work cannot be overemphasized. We also thank numerous colleagues who helped us in many different ways to complete the manuscript. Weare particularly indebted to Dr. Dorotbee Wegmann for her expertise with which she eliminated many errors and inconsistencies of the first versions. Special thanks are due to Dr. Rich Knochenmuss (ETH ZUrich) for the MALDI mass spectra of matrix materials, Dr. Kikuko Hayamizu for her help with the Spectral Database System of the National Institute of Materials and Chemical Research, Tsukuba, Ibaraki (Japan), Prof. Bernhard Jaun and Dr. Martin Badertscher (ETH ZUrich) for critically reading parts of the manuscript. Dr. Martin Badertscher is also thanked for the tutorial of the structure generator, Assemble 2.0, and Upstream Solutions (Hergiswil, Switzerland) for providing free versions of the computer programs on the enclosed compact disk. In spite of great efforts and many checks to eliminate errors, it is likely that some errors or inconsistencies remain. We would like to encourage our readers to contact us with comments and suggestions or any kind of problems when using the book or the enclosed programs under one of the following addresses: Prof. Erna Pretsch, Laboratory of Organic Chemistry, CH-8092 ZUrich, Switzerland, pretsch@org.chem.ethz.ch.orprof.philippe BUhlmann, Department of Chemistry, University of Minnesota, 207 Pleasant St., SE, Minneapolis, MN 55455, USA, buhlmann@chem.umn.edu. Zurich and Tokyo, August 2000
6 VII 1 Introduction Scope and Organization Abbreviations and Symbols Summary Tables General Tables Calculation of the Number of Double Bond Equivalents from the Molecular Formula Properties of Selected Nuclei C NMR Spectroscopy IH NMR Spectroscopy IR Spectroscopy Mass Spectrometry Average Masses of Naturally Occurring Elements with Exact Masses and Representative Relative Abundances of Isotopes Ranges of Natural Isotope Abundances of Selected Elements Isotope Patterns of Naturally Occurring Elements Calculation of Isotope Distributions Isotopic Abundances of Various Combinations of Chlorine, Bromine, Sulfur, and Silicon Isotope Patterns of Combinations of Cl and Br Indicators of the Presence of Heteratoms Rules for Determining the Relative Molecular Weight (Mr) Homologous Mass Series as Indications of Structural Type Mass Correlation Table References UVNis Spectroscopy Combination Tables Alkanes, Cycloalkanes Alkenes, Cycloalkenes Alkynes Aromatic Hydrocarbons Heteroaromatic Compounds... 53
7 VIII 3.6 Halogen Compounds Oxygen Compounds Alcohols and Phenols Ethers Nitrogen Compounds Amines Nitro Compounds Thiols and Sulfides Carbonyl Compounds Aldehydes Ketones Carboxylic Acids Carboxylic Esters and Lactones Carboxylic Amides and Lactams C NMR Spectroscopy Alkanes Chemical Shifts Coupling Constants References Alkenes Chemical Shifts Coupling Constants References Alkynes Chemical Shifts Coupling Constants References Alicyclics Chemical Shifts Coupling Constants References Aromatic Hydrocarbons Chemical Shifts Coupling Constants References Heteroaromatic Compounds Chemical Shifts Coupling Constants Halogen Compounds Fluoro Compounds Chloro Compounds Bromo Compounds Iodo Compounds References Alcohols, Ethers, and Related Compounds Alcohols Ethers
8 IX 4.9 Nitrogen Compounds Amines Nitro and Nitroso Compounds Nitrosamines Imines and Oximes Hydrazones and Carbodiimides Nitriles and Isonitriles Isocyanates, Thiocyanates and Isothiocyanates References Sulfur-Containing Functional Groups Thiols Sulfides Disulfides and Sulfonium Salts Sulfoxides and Sulfones Sulfonic and Sulfinic Acids and Derivatives Sulfurous and Sulfuric Acid Derivatives Sulfur-Containing Carbonyl Derivatives Carbonyl Compounds Aldehydes Ketones Carboxylic Acids and Carboxylates Esters and Lactones Amides and Lactams Miscellaneous Carbonyl Derivatives Miscellaneous Compounds Derivatives of Group IV Elements Phosphorus Compounds Miscellaneous Organometallic Compounds Natural Products Amino Acids Carbohydrates Nucleotides and Nucleosides Steroids Spectra of Solvents and Reference Compounds l3c NMR Spectra of Common Deuterated Solvents l3c NMR Spectra of Secondary Reference Compounds l3c NMR Spectrum of a Mixture of Common Nondeuterated Solvents H NMR Spectroscopy Alkanes Chemical Shifts Coupling Constants References Alkenes Substituted Ethylenes Dienes Alkynes
9 X Chemical Shifts and Coupling Constants A1icyc1ics AromaticHydrocarbons Heteroaromatic Compounds Non-Condensed Heteroaromatic Rings Condensed Heteroaromatic Rings Halogen Compounds Fluoro Compounds Chloro Compounds Bromo Compounds Iodo Compounds Alcohols, Ethers, and Related Compounds Alcohols Ethers Nitrogen Compounds Amines Nitro and Nitroso Compounds Nitrosamines, Azo, and Azoxy Compounds Imines, Oximes, Hydrazones, and Azines Nitriles and Isonitriles Cyanates, Isocyanates, Thiocyanates, and Isothiocyanates Sulfur-Containing Functional Groups Thiols Sulfides Disulfides and Sulfonium Salts Sulfoxides and Sulfones Sulfonic, Sulfinic, Sulfurous, and Sulfuric Acids and Derivatives Thiocarboxylate Derivatives Carbonyl Compounds Aldehydes Ketones Carboxylic Acids and Carboxylates Esters and Lactones Amides and Lactams Miscellaneous Carbonyl Derivatives Miscellaneous Compounds Silicon Compounds Phosphorus Compounds Miscellaneous Compounds Natural Products Amino Acids Carbohydrates Nuc1eotides and Nucleosides References Spectra of Solvents and Reference Compounds IH NMR Spectra of Common Deuterated Solvents H NMR Spectra of Secondary Reference Compounds
10 XI IH NMR Spectrum of a Mixture of Common Nondeuterated Solvents IR Spectroscopy Alkanes Alkenes Monoenes Allenes Alkynes Alicyclics Aromatic Hydrocarbons Heteroaromatic Compounds Halogen Compounds Fluoro Compounds Chloro Compounds Bromo Compounds Iodo Compounds Alcohols, Ethers, and Related Compounds Alcohols and Phenols Ethers, Acetals, Ketals Epoxides Peroxides and Hydroperoxides Nitrogen Compounds Amines and Related Compounds Nitro and Nitroso Compounds Imines and Oximes Azo Compounds Nitriles and Isonitriles Diazo Compounds Cyanates and Isocyanates Thiocyanates and Isothiocyanates Sulfur-Containing Functional Groups Thiols and Sulfides Sulfoxides and Sulfones Thiocarbonyl Derivatives Thiocarbonic Acid Derivatives Carbonyl Compounds Aldehydes Ketones Carboxylic Acids Esters and Lactones Arnides and Lactames Acid Anhydrides Acid Halides Carbonic Acid Derivatives Miscellaneous Compounds Silicon Compounds Phosphorus Compounds
11 XII Boron Compounds Amino Acids Solvents, Suspension Media, and Interferences Infrared Spectra of Common Solvents Infrared Spectra of Suspension Media Interferences in Infrared Spectra Mass Spectrometry Alkanes Unbranched Alkanes Branched Alkanes References Alkenes UnbranchedAlkenes Branched Alkenes Polyenes and Polyynes References Alkynes Aliphatic Alkynes References Alicyclic Hydrocarbons Cyclopropanes Saturated Monocyclic Alicyclics Polycyclic Alicyclics Cyclohexenes References Aromatic Hydrocarbones Aromatic Hydrocarbons Alkylsubstituted Aromatic Hydrocarbons References Heteroaromatic Compounds General Characteristics Furans Thiophenes Pyrroles Pyridines N-Oxides of Pyridines and Quinolines Pyridazines and Pyrimidines Pyrazines Indoles Quinolines Cinnoline References Halogen Saturated Aliphatic Halides Polyhaloalkanes Aromatic Halides References
12 XIII 7.8 Alcohols Aliphatic Alcohols Alicyclic Alcohols Unsaturated Aliphatic Alcohols Vicinal Glycols Aliphatic Hydroperoxides Phenols Benzyl Aliphatic Ethers UnsaturatedEthers Alkyl Cycloalkyl Ethers Cyclic Ethers Aliphatic Epoxides Methoxybenzenes Alkyl Aryl Ethers Aromatic Ethers Aliphatic Peroxides References Nitrogen Compounds Saturated Aliphatic Arnines Cycloalkylarnines Cyclic Arnines Piperazines Aromatic Arnines Aliphatic Nitro Compounds Aromatic Nitro Compounds Diazo Azobenzenes Aliphatic Azides AromaticAzides Aliphatic Nitriles Aromatic Nitriles Aliphatic Isonitriles (R-NC) Aromatic Isonitriles (R-NC) Aliphatic Cyanates (R-OCN) Aromatic Cyanates (R-OCN) Aliphatic Isocyanates (R-NCO) Aromatic Isocyanates (R-NCO) Aliphatic Thiocyanates (R-SCN) Aromatic Thiocyanates (R-SCN) Aliphatic Isothiocyanates (R-NCS) Aromatic Isothiocyanates (R-NCS) References Sulfur-Containing Functional Groups Aliphatic Thiols Aromatic Thiols Aliphatic Sulfides Alkyl Vinyl Sulfides Cyclic Sulfides
13 XIV Aromatic Sulfides Disulfides Aliphatic Sulfoxides Alkyl Aryl and Diaryl Sulfoxides Aliphatic Sulfones Cyclic Sulfones Alkyl Aryl Sulfones Diaryl Sulfones Aromatic Sulfonic Acids Alkylsulfonic Acid Esters Arylsulfonic Acid Esters Aromatic Sulfonamides Thiocarboxylic Acid S-Esters References Carbonyl Compounds Aliphatic Aldehydes Unsaturated Aliphatic Aldehydes Aromatic Aldehydes Aliphatic Ketones Unsaturated Ketones Alicyclic Ketones Aromatic Ketones Aliphatic Carboxylic Acids Aromatic Carboxylic Acids Carboxylic Acid Anhydrides Saturated Aliphatic Esters Unsaturated Esters Esters of Aromatic Acids Lactones Aliphatic Amides Arnides of Aromatic Carboxylic Acids Anilides Lactams Irnides References Miscellaneous Compounds Trialkylsilyl Ethers Alkyl Phosphates Aliphatic Phosphines Aromatic Phosphines and Phosphine Oxides References Mass Spectra of Common Solvents and Matrix Compounds Electron Impact Ionization Mass Spectra of Common Solvents Spectra of Common FAB MS Matrix and Calibration Compounds Spectra of Common MALDI MS Matrix Compounds References
14 XV 8 UV/Vis Spectroscopy Correlation Between Wavelength of Absorbed Radiation and Observed Color UVNis Absorption of Simple Chromophores UVNis Absorption of Conjugated Alkenes UV Absorption of Dienes and Polyenes UV Absorption of a,~-unsaturated Carbonyl Compounds UVNis Absorption of Aromatic Compounds UV Absorption of Monosubstituted Benzenes UV Absorption of Substituted Benzenes UV Absorption of Aromatic Carbonyl Compounds UVNis Reference Spectra UVNis Spectra of Alkenes and Alkynes UVNis Spectra of Aromatic Compounds UV Nis Spectra of Heteroaromatic Compounds UVNis Spectra of Miscellaneous Compounds UVNis Spectra of Nuc1eotides UVNis Absorption of Common Solvents Subject Index
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