Tables of Spectral Data for Structure Determination of Organic Compounds PDF
Preview Tables of Spectral Data for Structure Determination of Organic Compounds
Chemical Laboratory Practice Editors W. Fresenius J. F. K. Huber E. Pungor G. A. Rechnitz W Simon Th. S. West Pretsch Clerc Seibl Simon Tables of Spectral Data for Structure Determination of Organic Compounds Translated from the German by K.Biemann Second Edition Springer-Verlag Berlin Heidelberg GmbH P. D. Dr. Erni:i Pretsch, Professor Dr. Joseph Seibl, Professor Dr. Wilhelm Simon Eidgeni:issische Technische Hochschule, Laboratorium ftir Organische Chemie, Universitatsstral3e 16, CH-8092 Ziirich Professor Dr. Thomas Clerc Pharmazeutisches Institut der Universitat, Baltzerstral3e 5, CH-3012 Bern Translated from the German by Prof. Dr. Klaus Biemann Dept. of Chemistry, Massachusetts lost. ofTechnology, Cambridge, MA 02139/USA Editors Prof. Dr. Wilhelm Fresenius, lnstitut Fresenius, Chemische und Biologische Laboratorien GmbH, lm Maisel, D-6204 Taunusstein 4, FRG Prof. Dr. J. F. K. Huber, lnstitut fUr Analytische Chemie der Universitiit Wien, Wah ringer Stral3e 38, A-1090 Wien, Austria Prof. Dr. Emo Pungor, lnsitute for General and Analytical Chemistry, Gellert-ter 4, H-1502 Budapest XI, Hungary Prof. Garry A. Rechnitz, Dept. of Chemistry, Univ. of Delaware, Newark, DE 19711, USA Prof. Dr. Wilhelm Simon, Eidgenossische Technische Hochschule, Laboratorium fUr Organische Chemie, Universitiitsstral3e 16, CH-8092 ZUrich, Switzerland Prof. Thomas S. West, Macaulay Institute for Soil Research, CraigiebuckJer, Aberdeen AB9 2QJ, U.K. ISBN 978-3-540-51202-8 ISBN 978-3-662-10207-7 (eBook) DOI 10.1007/978-3-662-10207-7 This work is subject to copyright. All rights are reserved, whether the whole orpartofthe material is concerned, specifically the rights of translation, reprinting, re-use of illustra tions, recitation, broadcasting, reproduction on microfilms or in other ways, and storage in data banks. Duplication oft his publication or parts thereofisonlypermitted underthe provisions of the German Copyright LawofSeptember9, 1965, in its version of June 24, 1985,and a copyright fee must always be paid. Violations fall under the prosecution act of the German Copyright Law. ©Springer-Verlag Berlin Heidelberg 1983 and 1989 Originally published by Springer-Verlag Berlin Heidelberg New York in 1989 The use of registered names, trademarks, etc. in this publication does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use. 2152/3020 543210 Preface to the Second English Edition The Third German Edition of the "Tables of Spectral Data" had been greatly expanded particularly in the area of 13C-NMR and, to a lesser extent, of 'H-NMR. For these two fields, as well as in the chapter on mass spectrometry, some more textual material has been added. These new features, combined with the wide acceptance of the Tables in the English speaking world, made it advisable to also translate the Third German Edition into English. As in the previous translation, this provided an opportunity for a few corrections and further additions. All areas of spectroscopy have now reached a high level of maturity, which assures that the data compiled in this work represent a rather complete condensation of the information available in the literature. It is expected that the book will find good use in the hands of the chemist who is concerned with the correlation of such spectroscopic data with the structure of organic compounds. Klaus Biemann Cambridge, MA June 1989 Preface to the English Edition Although numerical data are, in principle, universal, the compilations presented in this book are extensively annotated and interleaved with text. This translation of the second German edition has been prepared to facilitate the use of this work, with all its valuable detail, by the large community of English-speaking scientists. Translation has also provided an opportunity to correct and revise the text, and to update the nomenclature. Fortunately, spectroscopic data and their relationship with structure do not change much with time so one can predict that this book will, for a long period of time, continue to be very useful to organic chemists involved in the identification of organic compounds or the elucidation of their structure. Klaus Biemann Cambridge, MA, April 1983 Preface to the First German Edition Making use of the information provided by various spectroscopic tech niques has become a ·matter of routine for the analytically oriented organic chemist. Those who have graduated recently received extensive training in these techniques as part of the curriculum while their older colleagues learned to use these methods by necessity. One can, therefore, assume that chemists are well versed in the proper choice of the methods suitable for the solution of a particular problem and to translate the experimental data into structural information. Those who are not specialists in any of these techniques and there fore not in continuous contact with the corresponding data may wish to have a compact summary of reference data in a form that can be grasped easily. Even experts appreciate the opportunity to look up in a summary information about compound types with which they are not familiar. The tables compiled in this book are meant to fill this gap. They were compiled for courses and exercises which the authors offered over a ten year period to students at the Federal Institute of Technology (ETH), Zurich, and are thus well suited as a basis for similar courses elsewhere. Considering such a broad effort there will undoubtedly be some omis sions and errors in our presentations. We would be grateful to users of this book for suggestions and criticisms which would help us to keep it up to date. A postcard included in the book may make it easier for the reader to make such comments. We would also be grateful to receive reprints of papers containing information and data which could be incorporated in later editions and thus improve their usefulness. A book such as this could not be assembled without the help of enthu siastic and knowledgeable collaborators who contributed a good deal to the work. Our special thanks go to Miss I. Port, Dr. D. Wegmann as well as Mr. P. Oggenfuss and Dr. R. Schwarzenbach. Preface to the Second German Edition This second edition provided an opportunity to include many additions and correct some errors. Amongst other improvements tables and figures concerning opaque regions and error-signals in the infrared were added. We also appreciate correspondence which led to a number of corrections. Our special thanks go to Dr. D. vlegmann and Mr. P. Oggenfuss for their very careful cooperation. It is due to their efforts that this new edition was produced in a timely fashion. VII Preface to the Third German Edition In view of the success of the first two editions of our data tables and their translations into various languages, we feel the responsibility to adapt the work to the continuous development of analytical instrumentation and to update the Tables to the present level of information available. The original concept to present a somewhat limited but well balanced set of reference data will be retained. Therefore, we had to exercise restraint in the selection of additional data to avoid unmanageable growth of the volume. In the interest of the ease of use, we took the risk of a certain redurrlancy in same of the data if they properly fit into more than one area. To facilitate, if necessary, the access to larger or more specialized collections of data we oampiled such a list on page A10-A15. The major portion of the newly added material concerns the 13c-NMR data, most of which became available only recently. These data were selected and presented in a manner which closely resembles the organization of the 1H-NMR section, so that now all of the listed oampourrl classes are characterized by roth of these techniques. The 1H-NMR section was strengthened with the addition of additivity rules and data for oampourrl types (such as naphthalenes and amino acids) which had been underrepresented in the previous editions. To the MS chapter, a brief description of fragmentation processes characteristic of mo=functional oampounds was added. In addition to the listing of the typical absorption regions in the IR, the absorption frequencies of selected reference oampounds were added. Finally, in a new section entitled "VARIA" a number of rules of practical importance are outlined. 1) Calculation of the number of double b:Jnd equivalents from a molecular formula. 2) Conversion of chemical shifts from external to internal reference. 3) Prediction of the type of spin-spin interactions based on the syrrunetry properties and rapid changes in the conformation of molecules. VIII We would like to thank our readers for ccmnents which led to co=ections and changes in the new edition and, at the same time, ask for contintDus criticism and suggestions , which we greatly appreciate. We are particularly indebted to Dr. D. Wegmann for the expertise with which she very carefully prepared the manuscript and to Mrs. M. Schlatter for the exceptional layout and cc.rnposition of the Tables. Both have contributed substantially to the success of the work. ZUrich, Decenber 1985 IX Table of Contents Introduction . . . . . . . AS Abbreviations and Symbols A20 Summary Tables BS 1 3C-NMR BS 1H-NMR BlS IR B35 UV/VIS B65 Combination Tables B75 Alkanes, Cycloalkanes B75 Alkenes, Cycloalkenes B85 Alkynes . . . . . B95 Aromatics . . . . BlOS Heteroaromatics . BllS Halogen Compounds Bl25 Alcohols, Phenols Bl35 Ethers . . . . Bl45 Amines . . . . . Bl55 Nitro Compounds . Bl65 Thiols, Thioethers Bl75 Aldehydes . . . . . Bl85 Ketones . . . . . . Bl95 Carboxylic Acids B205 Carboxylic Esters, Lactones B215 Amides, Lactams ..... . B235 13C-Nuclear Magnetic Resonance Spectroscopy cs All:anes . . . . . • . . • • . • . . . . . cs Additivity Rules for Substituted Alkanes ClO Methyl Groups • . . • . C30 Monosubstituted Alkanes C40 n-Octanes .•. C46 Alicycles . . • • . • . :c47 Methylcyclohexanes ·cso Monosubstituted Cyclohexanes C70 Condensed Alicyles C72 Alkenes . • . . . • . . • C80 Vinyl Compounds . . • . . C90 1,2-Disubstituted Alkenes C96 Enols C97 Cycloalkenes ClOO Allenes ClOS Alkynes . • . CllO Aromatic Hydrocarbons .•..•.. Cll5 Substituent Effects in Benzene Cl20 Substituent Effects in Naphthalene Cl26 5-Membered Heteroaromatic Rings Cl35 Substituent Effects in Pyridine Cl40 6-Membered Heteroaromatic Rings Cl55 Condensed Heteroaromatics Cl60 Halogen Compounds Cl67 Alcohols Cl70 Ethers Cl72 Amines . . • . . Cl74 Nitro- and Nitroso Compounds Cl78 Nitramines . . • . . . Cl79 Thiols ..........• Cl79 Thioethers, Disulfides Cl80 Sulfonium Salts, Sulfoxides, Sulfones, Sulfonic Acids Cl81 Acetyl Derivatives • . . . . ..... . Cl83 Additivity Rules for Aldehydes, Ketones . Cl84 Additivity Rules for Carboxylic Acids and Esters Cl84 Additivity Rules for Amides Cl85 Carbonyl Groups Cl86 Aldehydes Cl87 Ketones . • . . ClBB Quinones Cl90 Carboxylic Acids Cl9l Carboxylate Anions Cl92 Carboxylic Acid Esters Cl93 Lac tones Cl95 Amides . . • • Cl96 Lactams . . • . Cl97 Acid Anhydrides Cl98 Acid Halides Cl98 Carbonic Acid Derivatives Cl99 Nitriles, Isonitriles .. C200 !mines, Oximes, Isocyanates C201 Hydrazones, Carbodiimides . C202 Sulfur Containing Carbonyl Derivatives C203 Thiocyanates, Isothiocyanates C204 Amino Acids . • . . • . . . . . • C205 Monosaccharides . • . • • . . • . C210 Pyrimidine Bases and Nucleosides C2ll Purine Bases and Nucleosides C212 Phosphorous Compounds . . . C215 13c-1H Coupling Constants . C220 13c-13c coupling Constants C240 13c-19p Coupling Constants C245 Solvent Spectra •..... C250 Proton Resonance Spectroscopy i:l5 Monosubstituted Alkanes .. H5 Polysubstituted Alkanes, Additivity Rule Hl5 Coupling in Aliphatic Compounds H20 Aromatic Substituted Alkanes H30 Aliphatic Halogen Compounds H45 Alcohols H50 Ethers H60 Amines H75 Nitro Compounds H90 N-Nitroso-, Azo- and Azoxy Compounds H90 Thiols . . . . . . . . . . . . . . . H95 XI
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