The Chemistry of Nonaqueous Solvents. Volume VB: Acid and Aprotic Solvents PDF
Preview The Chemistry of Nonaqueous Solvents. Volume VB: Acid and Aprotic Solvents
Contributors ALBERT W. JACHE D. H. KERRIDGE DOMINIQUE MARTIN JOHN B. MILNE SARASWATHI NATARAJAN RAM CHAND PAUL ROGER ROUSSON GURDEV SINGH JEAN-MARC WEULERSSE THECHEMISTRYOF NONAQUEOUS SOLVENTS Edited by J. J. LAGOWSKI DEPARTMENT OF CHEMISTRY THE UNIVERSITY OF TEXAS AT AUSTIN AUSTIN, TEXAS Volume VB ACIDIC AND APROTIC SOLVENTS 1978 ACADEMIC PRESS New York San Francisco London A Subsidiary of Harcourt Brace Jovanovich, Publishers COPYRIGHT © 1978, 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 7DX Library of Congress Cataloging in Publication Data Lagowski, J J ed. The chemistry of non-aqueous solvents. Includes bibliographies. CONTENTS: v.l. Principles and techniques.- v. 2. Acidic and basic solvents.-v. 3. Inert, aprotic, and acidic solvents, [etc.] 1. Nonaqueous solvents. TP247.5.L3 660.2'9'482 66-16441 ISBN 0-12-433841-0 (v. 5B) PRINTED IN THE UNITED STATES OF AMERICA List of Contributors Numbers in parentheses indicate the pages on which the authors' contributions begin. ALBERT W. JACHE, Department of Chemistry, Marquette University, Mil- waukee, Wisconsin (53) D. H. KERRIDGE, Department of Chemistry, The University, Southampton, England (269) DOMINIQUE MARTIN, Division de Chimie, Centre D'fitudes Nucleaires de Saclay, Gif-sur-Yvette, France (157) JOHN B. MILNE, Department of Chemistry, University of Ottawa, Ottawa, Ontario, Canada (1) SARASWATHI NATARAJAN, Department of Chemistry, Marquette University, Milwaukee, Wisconsin (53) RAM CHAND PAUL, Department of Chemistry, Panjab University, Chandi- garh, India (197) ROGER ROUSSON, Division de Chimie, Centre D'Etudes Nucleaires de Saclay, Gif-sur-Yvette, France (157) GURDEV SINGH, Department of Chemistry, Panjab University, Chandigarh, India (197) JEAN-MARC WEULERSSE, Division de Chimie, Centre D'Etudes Nucleaires de Saclay, Gif-sur-Yvette, France (157) Preface Volume V of this treatise completes the original plan established in 1965 to attempt a critical analysis of the subject from two points of view, viz., (1) a discussion of the theoretical aspects of nonaqueous solution chemistry independent of solvent and (2) a consideration of individual solvents or solvent types for which reasonably comprehensive information has been gathered to this point in time. Chapters 1-4 in this volume contribute to the first point of view whereas the remaining chapters, for the most part, contain information on individual solvent systems; there is, of course, some discussion of special aspects of theory in the latter class of chapters. Taken as a whole, the 38 chapters in the 5 volumes of this treatise would have been organized according to the following outline, if the Editor had been able to overcome the logistic problems associated with the personal work schedules of the contributors. The Chemistry of Nonaqueous Solvents Part I. Practical Aspects 1. Experimental Techniques for Low-Boiling Solvents, Jindnch Nassler, Ch. 6, Vol. I 2. Experimental Techniques in the Study of Fused Salts, R. A. Bailey and G. J. Jany, Ch. 7, Vol. I 3. Ion-Selective Electrodes in Nonaqueous Solvents, E. Pungor and K. Toth, Ch. 4, Vol. VA 4. Electrochemical Methods, P. Zuman and W. Wawzonek, Ch. 3, Vol. VA 5. Conductivity in Nonaqueous Solvents, John H. Roberts, Ch. 1, Vol. IV 6. Solvent Extraction of Inorganic Species, Leonard T. Katzen, Ch. 5, Vol. I Part II. Theoretical Aspects 7. Lewis Acid-Base Interactions in Polar Nonaqueous Solvents, Devon W. Meek, Ch. 1, Vol. I 8. Bronsted Acid-Base Behavior in "Inert" Organic Solvents, Marion Maclean Davis, Ch. 1, Vol. HI ix X PREFACE 9. Solvation of Electrolytes and Solution Equilibria, Elton Price, Ch. 2, Vol. I 10. Solvation and Complex Formation in Protic and Aprotic Solvents, Sten Ahrland, Ch. 1, Vol. VA 11. Solvent Basicity, Robert L. Benoit and Christen Louis, Ch. 2, Vol. VA 12. Electrode Potentials in Nonaqueous Solvents, H. Strehlow, Ch. 4, Vol. I 13. Redox Systems in Nonaqueous Solvents, Michel Rumeau, Ch. 3, Vol. IV 14. Acidity Functions for Amphiprotic Media, Roger G. Bates, Ch. 3, Vol. I 15. Hydrogen Bonding Phenomena, Ann T. Lemley, Ch. 2, Vol. IV Part III. Acidic Solvents 16. Liquid Hydrogen Chloride, Hydrogen Bromide, and Hydro- gen Iodide, Frank Klanberg, Ch. 1, Vol. II 17. Anhydrous Hydrogen Fluoride as a Solvent and a Medium for Chemical Reactions, Martin Kilpatrick and John G. Jones, Ch. 2, Vol. II 18. Liquid Hydrogen Sulfide, F. Feher, Ch. 4, Vol. Ill 19. Sulfuric Acid, Witt Lee, Ch. 3, Vol. II 20. Halosulfuric Acids, S. Natarajan and A. W. Jache, Ch. 2, Vol. VB 21. Nitric Acid, W. H. Lee, Ch. 4, Vol. II 22. Anhydrous Acetic Acid as Nonaqueous Solvent, Alexander I. Popov, Ch. 5, Vol. Ill 23. Other Carboxylic Acids, Alexander I. Popov, Ch. 6, Vol. Ill 24. Trifluoroacetic Acid, John B. Milne, Ch. 1, Vol. VB Part IV. Basic Solvents 25. Liquid Ammonia, J. J. Lagowski and G. A. Moczygemba, Ch. 7, Vol. II 26. The Physical Properties of Metal Solutions in Nonaqueous Solvents, J. C. Thompson, Ch. 6, Vol. II 27. Hydrazine, D. Bauer and Ph. Gaillochet, Ch. 6, Vol. VA 28. Pyridine, J.-M. Nigretto and M. Jozefowicz, Ch. 5, Vol. VA 29. Tetramethylurea, Barbara J. Barker and Joseph A. Caruso, Ch. 4, Vol. IV 30. Amides, Joe W. Vaughn, Ch. 5, Vol. II PREFACE XI Part V. Aprotic Solvents 31. Liquid Sulfur Dioxide, D. F. Burow, Ch. 2, Vol. Ill 32. Sulfolane, Jukka Martinmaa, Ch. 2, Vol. IV 33. Inorganic Acid Chlorides of High Dielectric Constant (with Special Reference to Antimony Trichloride), E. C. Baughan, Ch. 5, Vol. IV 34. Inorganic Halides and Oxyhalides, R. C. Paul and G. Singh, Ch. 4, Vol. VB 35. Acyl Halides as Nonaqueous Solvents, Ram Chand Paul and Sarjit Singh Sandhu, Ch. 3, Vol. Ill 36. Cyclic Carbonates, W. H. Lee, Ch. 6, Vol. IV 37. The Interhalogens, D. Martin, R. Rousson, and J.-M. Weulersee, Ch. 3, Vol. VB 38. Molten Salts as Nonaqueous Solvents, D. H. Kerridge, Ch. 5, Vol. VB The division of some chapters between Parts I and II in the outline is somewhat arbitrary since many chapters in Part I are organized about well- established or evolving principles. I should like to acknowledge the help of Ms. R. Schall who assisted in numerous ways during the preparation of Volume V. The cooperation of the staff of Academic Press in many ways since the inception o tfhis treatise has been outstanding. Finally, the contributions of the numerous authors, both in terms of the manuscripts they produced and their numerous sug- gestions are gratefully appreciated. It is apparent that a very large number of persons contributed materially to the success of this effort since its inception in 1965. J. J. LAGOWSKI Contents of Other Volumes VOLUME I PRINCIPLES AND TECHNIQUES Lewis Acid-Base Interactions in Polar Nonaqueous Solvents DEVON W. MEEK Solvation of Electrolytes and Solution Equilibria ELTON PRICE Acidity Function for Amphiprotic Media ROGER G. BATES Electrode Potentials in Nonaqueous Solvents H. STREHLOW Solvent Extraction of Inorganic Species LEONARD I. KATZIN Experimental Techniques for Low-Boiling Solvents JINDRICH NASSLER Experimental Techniques in the Study of Fused Salts R. A. BAILEY AND G. J. JANZ Author Index—Subject Index VOLUME II ACIDIC AND BASIC SOLVENTS Liquid Hydrogen Chloride, Hydrogen Bromide, and Hydrogen Iodide FRANK KLANBERG Anhydrous Hydrogen Fluoride as a Solvent and a Medium for Chemical Reactions MARTIN KILPATRICK AND JOHN G. JONES Sulfuric Acid W. H. LEE xiii XIV CONTENTS OF OTHER VOLUMES Nitric Acid W. H. LEE Amides JOE W. VAUGHN The Physical Properties of Metal Solutions in Non aqueous Solvents J. C. THOMPSON Liquid Ammonia J. J. LAGOWSKI AND G. A. MOCZYGEMBA Author Index—Subject Index VOLUME III INERT, APROTIC, AND ACIDIC SOLVENTS Bronsted Acid-Base Behavior in "Inert" Organic Solvents MARION MACLEAN DAVIS Liquid Sulfur Dioxide D. F. BUROW Acyl Halides as Nonaqueous Solvents RAM CHAND PAUL AND SARJIT SINGH SANDHU Liquid Hydrogen Sulfide F. FEHER Anhydrous Acetic Acid as Nonaqueous Solvent ALEXANDER I. POPOV Other Carboxylic Acids ALEXANDER I. POPOV Author Index—Subject Index CONTENTS OF OTHER VOLUMES XV VOLUME IV SOLUTION PHENOMENA AND APROTIC SOLVENTS Conductivity in Nonaqueous Solvents JOHN H. ROBERTS Hydrogen Bonding Phenomena ANN T. LEMLEY Redox Systems in Nonaqueous Solvents MICHEL RUMEAU Tetramethylurea BARBARA J. BARKER AND JOSEPH A. CARUSO Inorganic Acid Chlorides of High Dielectric Constant E. C. BAUGHAN Cyclic Carbonates w. H. LEE Sulfolane JUKKA MARTINMAA Author Index—Subject Index VOLUME VA PRINCIPLES AND BASIC SOLVENTS Solvation and Complex Formation in Protic and Aprotic Solvents STEN AHRLAND Solvent Basicity ROBERT L. BENOIT AND CHRISTIAN LOUIS Nonaqueous Solvents in Organic Electroanalytical Chemistry PETR ZUMAN AND STANLEY WAWZONEK
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