Physical Methods in Heterocyclic Chemistry. Volume 6 PDF
Preview Physical Methods in Heterocyclic Chemistry. Volume 6
PHYSICAL METHODS IN HETEROCYCLIC CHEMISTRY A Comprehensive Treatise in Six Volumes Volume I—Nonspectroscopic Methods; Covering nonspectro- scopic methods to 1962 Volume II—Spectroscopic Methods; Covering spectroscopic methods to 1962 Volumes III and IV—Covering methods other than X-ray structure analysis from 1963 to 1970 Volume V—Bond Lengths and Angles from X-Ray Crystallog- raphy; Covering X-ray structure analysis to 1970 Volume VI—Covering five new physical methods (also includes Cumulative Subject and Author Indexes for Volumes I-VI). Physical Methods in Heterocyclic Chemistry Edited by A. R. KATRITZKY School of Chemical Sciences University of East Anglia Norwich, England VOLUME VI 1974 ACADEMIC PRESS · New York and London A Subsidiary of Harcourt Brace Jovanovich, Publishers COPYRIGHT © 1974, BY ACADEMIC PRESS, INC. ALL RIGHTS RESERVED. NO PART OF THIS PUBLICATION MAY BE REPRODUCED OR TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WRITING FROM THE PUBLISHER. ACADEMIC PRESS, INC. Ill Fifth Avenue, New York, New York 10003 United Kingdom Edition published by ACADEMIC PRESS, INC. (LONDON) LTD. 24/28 Oval Road, London NW1 Library of Congress Cataloging in Publication Data Main entry under title: Physical methods in heterocyclic chemistry. Includes bibliographies. 1. Heterocyclic compounds. I. Katritzky, Alan R., ed. [DNLM: 1. Heterocyclic compounds. QD400 K19p] QD400.P59 547'.59 63-12034 ISBN 0-12-401106-3 (v. 6) PRINTED IN THE UNITED STATES OF AMERICA Contributors to Volume VI Numbers in parentheses indicate the pages on which the authors' contributions begin. B. C. GILBERT (95), Department of Chemistry, University of York, Heslington, York, England E. HASELBACH (1), Physikalisch-Chemisches Institut der Universität Basel, Basel, Switzerland E. HEILBRONNER (1), Physikalisch-Chemisches Institut der Universität Basel, Basel, Switzerland J. P. Maier (1), Physikalisch-Chemisches Institut der Universität Basel, Basel, Switzerland KALEVI PIHLAJA (199), Department of Chemistry, University of Turku, Turku, Finland STEPHEN G. SCHULMAN (147), College of Pharmacy, University of Florida, Gainesville, Florida J. SHERIDAN (53), University College of North Wales, Bangor, U.K. ESKO TASKINEN (199), Department of Chemistry, University of Turku, Turku, Finland M. TRENWITH (95), Department of Chemistry, University of York, Heslington, York, England vu Preface This volume of "Physical Methods in Heterocyclic Chemistry" completes the treatise. Coverage is now extended to some of the more recently introduced physical methods which have rapidly become important to heterocyclic chemists. Volumes I and II, published in 1963, covered nonspectroscopic and spectroscopic methods, respectively, up to 1962. Volumes III and IV, published in 1971, covered an additional eight years of work on these same methods. Originally Volume V, comprised of a review of hetero- cyclic X-ray structure compiled by Dr. Wheatley, was to have com- pleted this work. Two factors caused an alteration in this plan: the amount of material on X-ray structure proved to be greater than ex- pected and a group of more recently introduced physical methods rapidly became of such increasing importance to heterocyclic chemists that it was necessary to include them to give the treatise the compre- hensive coverage desired. Thus this, the final volume, includes accounts of five additional physical methods not previously covered plus cumulative Subject and Author Indexes which include information for all the volumes. The topics comprising this volume are photoelectron spectroscopy (E. Heilbronner, J. P. Maier, and E. Haselbach), microwave spectro- scopy (J. Sheridan), electron spin resonance (B. C. Gilbert and M. Trenwith), fluorescence and phosphorescence (Stephen G. Schulman), and thermochemical applications to heterocyclic chemistry (Kalevi Pihlaja and Esko Taskinen). Editing this work has been a challenging but most enjoyable task. I would like to thank the many persons who by their contributions have helped to bring this work to fruition. A. R. KATRITZKY IX Preface to Volumes I and II Physical methods are perhaps the most important of all the in- fluences which have contributed to the fundamental changes of the last 50 years in the theory and practice of organic chemistry. Effective chemical research can now hardly be carried out without the aid of a variety of physical measurements. In the advance of physical techniques into organic chemistry, two main streams may be identified: physical chemists have commenced with the study of the simplest molecules and, using methods as rigorous as practicable, have proceeded stage by stage to structures of increasing complexity. Organic chemists have, by contrast, frequently made cor- relations of the (usually complex) structures with which they work: such correlations being, at least at first, purely empirical. Both streams are of vital importance to the over-all development—they complement each other, and chemists of each type need to be aware of the work in both streams. The systematic application of physical methods to heterocyclic chemistry has been slower than that to the other two traditional divi- sions of organic chemistry. This is probably because the molecular complexity of the heterocyclic field has hindered the advance into it by the physical chemist. A result is that most reviews and expositions of a physical method, or of a group of physical methods, deal but cursorily with its application to compounds of the heterocyclic class. The present two volumes seek to fill this gap—each chapter gives but a brief outline of the general theoretical and experimental aspects of the subject, and then gets down to surveying the literature in which the method has been applied to heterocyclic problems. This literature is often voluminous and is nearly always scattered. It is hoped that the present collection of reviews will save individual research workers much time and effort in literature searching. As Editor, I have been fortunate in being able to enlist an inter- national team of authors who are among the leaders in their respective fields, and my thanks go to each of them for their cooperation. We have tried to cover the literature to the beginning of 1962. A. R. KATRITZKY XI Preface to Volumes III, IV, and V Since the publication in 1963 of the first two volumes of this treatise, the application of physical methods to organic chemistry, and in particular to heterocyclic chemistry, has proceeded apace. The impor- tance of physical methods to structure determination and to the under- standing of inter- and intramolecular interactions has increased no less than the flood of new work. Heterocyclic chemists are thus faced with the necessity of having more to comprehend for the efficient execution of their work. The favorable reception given to volumes I and II encouraged us to update the work. All the chapters comprising the first two volumes have (with two exceptions) been amended. In addition, six new chapters are included covering methods which have achieved importance since 1963. Volume III includes the chapters on ionization constants (A. Albert) and on ultraviolet spectra (W. L. F. Armarego), topics included in Volumes I and II, respectively. Volume III also covers the following new topics: gas electron diffraction (P. Andersen and 0. Hassel), Raman spectroscopy (G. J. Thomas, Jr.), mass spectrometry (G. Spiteller), gas-liquid chromotography (Ya. L. Gol'dfarb et al.), and optical rotatory dispersion, circular dichroism, and magnetic dichroism (R.B.Homer). Volume IV includes chapters on electric dipole moments (J. Kraft and S. Walker) and heteroaromatic reactivity (J. H. Ridd), which originally appeared in Volume I, and chapters on nuclear quadrupole resonance (E. A. C. Lücken), nuclear magnetic resonance (R. F. M. White and H. Williams), and infrared spectra (A. R. Katritzky and P. J. Taylor), which originally formed part of Volume II. Volume IV also includes one new topic: dielectric absorption (S. Walker). Volume V is devoted to a single topic: bond lengths and angles from X-ray crystallography. This topic occupied a mere sixteen pages in Volume I; it is a measure of the immense advance that has been made in the subject that a tabulation of available molecular parameters for heterocycles fills a whole volume. Volume VI, which is now in preparation, will consist of chapters on microwave spectroscopy, photoelectron spectroscopy, bond energies, and electron-spin resonance. Volume VI will also include comprehensive subject and author indexes to the whole treatise. A work of this magnitude must of necessity contain many gaps and xiii PREFACE TO VOLUMES ΠΙ, IV, AND V omissions. It is hoped, nevertheless, that the collection of the scattered literature references will be of considerable assistance in locating physical constants and other data. I would like to thank the authors and Academic Press for their help and cooperation throughout the preparation of these volumes. A. R. KATRITZKY XIV Contents of Other Volumes Volume I Ionization Constants ADMEN ALBERT Heteroaromatic Reactivity JOHN RIDD X-Ray Diffraction Studies of Heterocyclic Compounds W. COCHRAN The Solubility of Heterocyclic Compounds WOLFGANG PFLEIDERER Application of Dipole Moments to Heterocyclic Systems S. WALKER Electrochemical Properties in Solutions J. VOLKE Author Index—Subject Index Volume II The Electronic Absorption Spectra of Heterocyclic Compounds S. F. MASON Nuclear Quadrupole Resonance E. A. C. LÜCKEN Nuclear Magnetic Resonance Spectra R. F. M. WHITE Infrared Spectra A. R. KATRITZKY AND A. P. AMBLER Author Index—Subject Index Volume III Ionization Constants ADRIEN ALBERT The Gas Electron Diffraction Method P. ANDERSEN AND 0. HASSEL XV CONTENTS OF OTHER VOLUMES Raman Spectroscopy G. J. THOMAS, JR. Ultraviolet Spectra of Heterocycles W. L. F. ARMAREGO Mass Spectrometry of Heterocyclic Compounds G. SPITELLER Gas-Liquid Chromatography of Heterocyclic Compounds YA. L. GOL'DFARB, V. I. YAKERSON, V. A. FERAPONTOV, S. Z. TAITS, AND F. M. STOYANOVICH Optical Rotatory Dispersion, Circular Dichroism, and Magnetic Circular Dichroism R. B. HOMER Author Index—Subject Index Volume IV Dielectric Absorption of Heterocyclic Molecules S. WALKER Nuclear Quadrupole Coupling Constants E. A. C. LÜCKEN Heteroaromatic Reactivity J. H. RIDD Nuclear Magnetic Resonance Spectra R. F. M. WHITE AND H. WILLIAMS Recent Applications of Electric Dipole Moments to Heterocyclic Systems J. KRAFT AND S. WALKER Infrared Spectroscopy of Heterocycles A. R. KATRITZKY AND P. J. TAYLOR Author Index—Subject Index Volume V X-Ray Diffraction P. J. WHEATLEY Author Index—Subject Index xvi
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