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Book & Media Reviews
Solvents and Solvent Effects in Organic Chemistry, Third Edition by Christian Reichardt Wiley-VCH, Weinheim, Germany, 2003. 629 pp. ISBN 3527306188 (cloth), $175 reviewed by Richard Pagni
In thinking back over the past four plus decades, from the time I had high school chemistry to the present, I recall only a few instances when I performed an experiment that did not involve a solvent. I believe my experience is typical of most chemists. We run reactions in solvents, work them up with solvents, do chromatography with solvents, and recrystallize solids from solvents. Alas, we often pay little heed to what solvents do in their various guises. Solvents often greatly influence chemical phenomena. The rate of the SN2 reaction of chloride with bromomethane, for example, varies by more than 15 orders of magnitude in going from water to the gas phase. Some Grignard reagents form in tetrahydrofuran, but not in diethyl ether. The number of such striking differences is large. Because my interests in chemistry have been so varied and the length of my academic career long, I have had occasion to run reactions in a wide range of solvents. Initially I often had only anecdotal knowledge of the chemical and physical properties of the solvent of interest and had to obtain reliable information rapidly. I always started my information searches by examining the first and second editions of this book because they contain a cornucopia of useful information on every significant relationship between organic chemistry and solvents. If I did not find enough specific information on the solvent of interest in the book, I always found references to articles where this information could be found. The third edition of Reichardt’s book has a structure and format identical to that of the earlier editions but is significantly larger and more up to date than the second edition, which appeared in 1988. New subjects such as room temperature ionic liquids are also found here. Perusal of the large number of references at the end of this edition suggests the coverage goes through 2001. The book contains seven wellorganized chapters on a wealth of topics including in-depth discussions of solvation, equilibria, kinetics, spectroscopy, and empirical measures of solvent polarity, a favorite topic of mine and one in which the author has made significant contributions. Every chapter is richly larded with tables, graphs, dia-
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Journal of Chemical Education
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Jeffrey Kovac University of Tennessee Knoxville, TN 37996-1600
grams, and equations. In addition, each topic is extensively referenced for further reading in the literature. There are also ten appendices that cover diverse topics including solvent purification, toxicity, and selection of solvents for recrystallization, chromatography, and reaction media. I have found the writing in this and earlier editions to be consistently clear and concise. Because the coverage is so vast, there is no room for wasted words or flowery language. I also give the author and publisher high praise for the excellent English because I still cannot decide if the book was originally written in English or German. I can’t detect any hint of German mannerisms or colloquialisms. There are both author and subject indices that help the reader wend his or her way through the book. However, finding one’s way through the indices takes a little effort. If, for example, you were interested in methanol, you will not find it (or most other solvents) listed in the subject index. The reason is obvious: If every solvent were cited in the index every time it was mentioned in the text, the index would probably run to 100 pages or more. So be more specific when looking. If you are interested in running a Diels-Alder reaction in methanol, then look up Diels-Alder reactions, (extensively referenced in the subject index) and proceed from there. I found it helpful to first peruse the volume to see its layout in detail before looking up specific topics. This effort didn’t take long and saved me time in the long run. This perusal was useful in another sense: In looking through the chapter on solvent polarity indices in the second edition many years ago, I discovered the omega index; subsequently George Kabalka and I have used it to measure the polarity of a reaction medium we were studying at that time (1). I believe it is well worth the time of every organic chemist to read this book and learn how solvents influence the myriad phenomena of organic chemistry. It is also a superb reference book, one that you will use often, with the largest bibliography on solvents and solvent effects that I have ever seen. The book is admittedly expensive and beyond the means of most graduate students, but one that will pay dividends in short order. I think that every practicing organic chemist should either own a copy or have easy access to one. Literature Cited 1. Pagni, R. M.; Kabalka, G. W.; Hondrogiannis, G.; Bains, S.; Anosike, P.; Kurt, R. Tetrahedron 1993, 49, 6743.
Richard Pagni is in the Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600;
[email protected].
Vol. 82 No. 3 March 2005
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www.JCE.DivCHED.org
