Naturally Occurring Quinones. - Journal of the American Chemical

Naturally Occurring Quinones. Lee Irvin Smith. J. Am. Chem. Soc. , 1958, 80 (14), pp 3806–3806. DOI: 10.1021/ja01547a101. Publication Date: July 1958...
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BOOKREVIEWS

It is very logical to discuss first all of the theoretical development, second irreversible properties such as conductance and diffusion, third the heat and volume functions and finally the free energies and activities, and this method makes a fine reference book, but i t makes reading or study very difficult. The errors in the treatment of the thermodynamics of the galvanic cell and in the first derivation of the Debye-Huckel potential which were noted in my review of the First Edition’ still persist. The Br$nsted theory of specific ion interaction includes the relation which most of us, but not Harned and Owen, call the Harned rule. Since this latter rule is discussed at great length one would expect a clear presentation of the Brg4nsted theory, but there was no part of the former editions which needed more drastic revision. Unfortunately the changes are trivial and no improvement at all. The collection and correlation of experimental results is the most valuable contribution. The focus is quite properly on the work at I’ale and similar work elsewhere, but there is remarkable freedom from pushing pet theories of the authors. Emphasis is placed upon precision work with simple electrolytes. Except for very brief excursions into hydration and into micelle formation with the aliphatic carboxylate ions, the only chemical reaction discussed is t h e association of weak electrolytes. I repeat with even more conviction the summarizing sentence of my former review, “Every worker in the field will be grateful to the authors for the labor they have spent collecting and coordinating this material, and will need to have a copy easily accessible.”

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minor errors anti, all in all, is not very useful. \ \ M e this book is meant to be mostly technological, a more coherent theoretical treatment would be helpful t o all readers. Such a presentation is not easy t o achieve in a brief space because of rapid developments. Furthermore, i t is difficult if not impossible for the authors to be critical and authoritative in so many arcas. For example, in the discussion of hemolysis (p. 3i2), the relation between penetration of cholesterol model membranes u n water by surfactants and their hemolytic activity (Pethica and Schulrnan) was not brought out. Agaiu, in the discussion of detergency and cleansing, solubilization is brought up in several places; it is not pointed out, however, t h a t most washing (except the hands) is done below the critical micelle concentration where solubilization is scarcely a factor. The coatiiig chemist can hardly be helped by the vague accounting of the Applications in Paints and Coatings (pp. 689). Separation into groupings on uses as dispersing agents, as wetting agents, as medicinal agents, etc., may have helped to avoid such a burden. It should be emphasized, however, t h a t the survey of types and processes for manufacture ill Part I will be quite valuable to many readers. Typography is excellent and few typographical errors S U C ~ I as those evident in the first letters of the lines in the iniddlc of p. 445 mar the contest. DEPARTMEST OF CHEMISTRY LEHIGH USIVERSITY BETHLEHEM,PEXNSYLVANI-4

A . C . ZETTLEMOYER

Naturally Occurring Quinones. K. H. Trrohrsox, D . S . , P h . D . , F.R.I.C., Lecturer in Organic Chemistry, University of Aberdeen. Scademic Press, Inc., 111 Fifth AveLfASSACHUSETTS INSTITUTE O F ‘rECHNOLOGY nue, New York 3, N. Y . 195i. vii 302 pp. 14.5 X CAMBRIDGE 39, ~IASSACHUSETTS GEORGESCATCHARD 22.5 cm. Price, $9.00. Among the oldest of known organic cornpout1ds, quiiiolles have been of interest to many organic chemists since the Surface Active Agents and Detergents. Volume 11. Axbeginning of t h e science. Their chemistry is complex and THOSY M. SCHWARTZ, Harris Research Laboratories, Washington, D. C., JAMES W. PERRY,Center for Docu- the multitude of reactions which they undergo forms a fascinating chapter of organic chemistry. They occur widementation and Communication Research, Western Reserve University, Cleveland, Ohio, and JULIAN BERCH, spread in nature and come from the most varied sources; many have had important uses which antedate the elaboraHarris Research Laboratories, Washington, D. C. Interscience Publishers, Inc., 250 Fifth Avenue, New York 1, tion of a n y systematic chemistry. Some are dyes, others are fungicides and disinfectants. Some have been used as X. Y. 1958. xv 839 pp. 16 X 23.5 cm. Price, medicines, others are toxic. Some are antibiotics, some $17.50. have been isolated from bacilli, some are vitamins. The tremendous growth of the literature on surface active Professor Thomson’s book is a valuable addition t o agents led the authors to restrict Volume I1 to developments chemical literature, for in it he has gathered together d l during the 1947-56 period. Their original intention was t o of the naturally occurring quinones. For each quinone tliC revise Volume I which was compiled by the first two of the snurces are given, the isolation is described, the physical present three authors. The vast number of carefully docu- properties are listed, and finally the proof of structure is mented references attest to the activity in the field and the given in quite some detail. The book is not-and is not attempts at completeness. As a source book, therefore, this intended t o be-a complete discussion of the chemistry of book deserves a place on the chemists’ bookshelf. quinones. I t is rather a detailed catalog of quinones, m ith Numerous advances recorded in the literature since 1956 enough of the chemistry, and a complete outline of the proof iii;tke it apparent t h a t Volume I1 already lacks freshness. o f structure, so t h a t thcrc is presented a compreheiisive This reaction is heightened by the curious arrangement llicture of the quinones occurring naturally. The discussolis which parallels Volume I. .%fter an introduction covering are adequate, well written, and extremely well documented. econotnics and general technological considerations, proc- There are three indexes: zoological, bot aiiical and general csscs for manufacturing surfactants are given in Part I . mid these indexes contribute greatly to the usefulness of tllc Therc follows in Part 11a miscellancous group of subjects iiibonk :is a reference. cluding surfactants for special functions such as germicides, There is a brief introtluction, atid this is followctl by f i v e fuiigicidcs nnd atitictrrrosive action, both inorganic aiitl cliapters: benzoquinolles (30 compounds, 159 rcferrliccs‘l; < irganic builders, both qualitative and quantitative arialysis iiaplithaquiriones (40 cnmpouiids. ,709 refcrcnccsi ; anthr:ta i l t i theti biological effccts. Part I11 attempts to survey quillones (70 compouucis, ,731 referellces); pheiiant1ir:iquirvceiit advances in the physical and colloidal chemistry of nones and miscellaneous auinones (8 compounds, 35 refersurfactants and ends with a non-critical survey of the coinences); cxteiided quiuones (aphins, hypericin, pseudoliyples field of detergency. Finally, Part IV comes back again pericin, fagopyrin, 51 references). to practical applications such as cleaning in its various asThe paper arid printing are excellcnt and tlic Ixxk-iii:rkiiifi pects, medical and cosmetic uses, uses in the mineral, buildis good. Altogetlier a first-rate contribution to the litcraing, agricultural, leather, paper, foil, plastics, paints, ture. petroleum and chemical industries. T h e arrangement seems involved and space-consuming t o this reviewer. SCHOOL OF CHEMISTRY LEE I R V I N SMITH OF MINNESOTA The presentation of theoretical developments in P a r t I11 is UNIVERSITY MINNEAPOLIS, MISNESOTA largely disjointed and incomplete, possesses a number of (1) TIIISJOURNAL, 66, 1043 (1944).

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