Structure Determination of Organic Compounds

1 Structure Determination of Organic CompoundsErn o Pretsch Philippe B uhlmann Martin BadertscherStructure Determinationof Organic CompoundsTables of Spectral DataFourth, Revised and Enlarged Edition123 Prof. Dr. Ern oPretschETH Z urichInstitute of Biogeochemistry andPollutant DynamicsUniversit atsstr. 168092 Z Martin BadertscherETH Z urichLaboratory of Organic ChemistryWolfgang-Pauli-Str. 108093 Z Dr. Philippe B uhlmannUniversity of MinnesotaDept. of Chemistry209 Pleasant Street SE.,Minneapolis, MN 978-3-540-93809-5e-ISBN 978-3-540-93810-1 DOI of Congress Control Number: 2009920112c Springer-Verlag Berlin Heidelberg 2009 This work is subject to copyright.

2 All rights are reserved, whether the whole or part of the material isconcerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting,reproduction on microfilm or in any other way, and storage in data banks. Duplication of this publicationor parts thereof is permitted only under the provisions of the German Copyright Law of September 9,1965, in its current version, and permission for use must always be obtained from Springer. Violations areliable to prosecution under the German Copyright use of general descriptive names, registered names, trademarks, etc.

3 In this publication does not imply,even in the absence of a specific statement, that such names are exempt from the relevant protective lawsand regulations and therefore free for general design:WMXD esign GmbHPrinted on acid-free ongoing success of the earlier versions of this book motivated us to prepare a new edition. While modern techniques of nuclear magnetic resonance spectros-copy and mass spectrometry have 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.

4 However, since the amount and quality of available data has considerably increased over the years, we decided to prepare a significantly revised manuscript. It follows the same basic concepts, , it provides a representative, albeit limited set of reference data for the interpretation of 13C NMR, 1H NMR, IR, mass, and UV/Vis spectra. We also added a new chapter with reference data for 19F and 31P NMR spectroscopy and, in the chapter on infrared spectroscopy, we newly refer to important Raman bands. Since operating systems of computers become outdated much faster than printed media, we decided against providing a compact disk with this new edition.

5 The limited versions of the NMR spectra estimation programs can be downloaded from the home page of the developing company ( ).We thank numerous colleagues who helped us in many different ways to com-plete the manuscript. We are particularly indebted to Dr. Doroth e Wegmann for her expertise with which she eliminated many errors and inconsistencies of the earlier versions. Special thanks are due to Prof. Wolfgang Robien for providing us with reference data from his outstanding 13C NMR database, CSEARCH. Another high-quality source of information was the Spectral Database System of the National Institute of Advanced Industrial Science and Technology ( ), Tsukuba, Ibaraki (Japan).

6 In spite of great efforts and many checks to eliminate errors, it is likely that some mistakes or inconsistencies remain. We would like to encourage our readers to con-tact us with comments and suggestions under one of the following addresses: Prof. Ern Pretsch, Institute of Biogeochemistry and Pollutant Dynamics, ETH Z rich, CH-8092 Z rich, Switzerland, e-mail: Prof. Philippe B hlmann, Department of chemistry , University of Minnesota, 207 Pleasant St. SE, Minne-apolis, MN 55455, USA, e-mail: or Dr. Martin Badertscher, Laboratory of Organic chemistry , ETH Z rich, CH-8093 Z rich, Switzerland, e-mail: rich and Minneapolis, November 2008 1 Introduction.

7 Scope and Organization .. Abbreviations and Symbols ..32 Summary Tables .. General Tables .. Calculation of the Number of Double Bond Equivalents from the Molecular Formula .. Properties of Selected Nuclei .. 13C NMR Spectroscopy .. 1H NMR Spectroscopy .. IR Spectroscopy .. Mass Spectrometry .. Average Masses of Naturally Occurring Elements with Masses and Representative Relative Abundances of Isotopes .. Ranges of Natural Isotope Abundances of Selected Elements Isotope Patterns of Naturally Occurring Elements .. Calculation of Isotope Isotopic Abundances of Various Combinations of Chlorine, Bromine, Sulfur, and Silicon.

8 Isotope Patterns of Combinations of Cl and Br .. Indicators of the Presence of Heteroatoms .. Rules for Determining the Relative Molecular Weight (Mr) . Homologous Mass Series as Indications of Structural Type . Mass Correlation References .. UV/Vis Spectroscopy ..463 Combination Tables .. Alkanes, Cycloalkanes .. Alkenes, Cycloalkenes .. Alkynes ..51 ContentsVIII Aromatic Hydrocarbons .. Heteroaromatic Compounds .. Halogen Compounds .. Oxygen Compounds .. Alcohols and Phenols .. Ethers .. Nitrogen Compounds .. Amines .. Nitro Compounds .. Thiols and Sulfides.

9 Carbonyl Compounds .. Aldehydes .. Ketones .. Carboxylic Acids .. Esters and Lactones .. Amides and Lactams ..674 13C 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 .. Aromatic Hydrocarbons .. Chemical Shifts .. Coupling Constants .. References .. Heteroaromatic Compounds .. Chemical Shifts ..101 Contents Coupling Constants.

10 Halogen Compounds .. Fluoro Compounds .. Chloro Compounds .. Bromo Compounds .. Iodo Compounds .. References .. Alcohols, Ethers, and Related Compounds .. Alcohols .. Ethers .. Nitrogen Compounds .. Amines .. Nitro and Nitroso Compounds .. Nitrosamines and Nitramines .. Azo and Azoxy Compounds .. Imines and Oximes .. Hydrazones and Carbodiimides .. Nitriles and Isonitriles .. Isocyanates, Thiocyanates, and Isothiocyanates .. Sulfur Compounds .. Thiols .. Sulfides .. Disulfides and Sulfonium Salts .. Sulfoxides and Sulfones .. Sulfonic and Sulfinic Acids and Derivatives.