Naturally occurring oxygen ring compounds (Dean, F. M.) - Journal of

Naturally occurring oxygen ring compounds (Dean, F. M.). William R. Roderick. J. Chem. Educ. , 1964, 41 (9), p 519. DOI: 10.1021/ed041p519.3. Publicat...
0 downloads 0 Views 3MB Size
has it, has been justified theoretically and the explanation readily lends itself for use in discussing systems where silicon is bonded to nitrogen, oxygen and the h a b gens, and is invoked to explain nearly all the differences in structure and reactivity between organic compounds and their analogues containing other elements of the fourth group. It is, therefore, an apprw priate time to prtU8e and take stock. Thk exercise runs as a thread of argument through the entire book and marks perhaps its leading feature. Dr. Ebsworth has produced s, highly critical compilation of the wide variety of phyaicel rtnd chemical evidence now available and he draws wise and careful conclusions concerning the limitations of its application. The approach throughout is from the modern physico-chemical viewpoint and much space is devoted to the resulta of spectroscopic studies, especially NMR. Again judicious use is made of the data, and the author is continually a t pains to point out the limitations of the methoda as with the relative values of the proton chemical shifts in methane and silane. Along the way we are treated to the concept of the "Scandanide Contn~etiau,"a clever construct helpful in rationalizing the relatively small change in covalent radius between silicon and germanium, and perhaps a cause of the alternating electronegativity found in the fourth group as well. Certainly s. great handicap in summarizing present knowledge in 80 active a field is that conclusions drawn in the manuscript will be dated by new work by the time of publication, and West's stable silieonium ion (C&EI\', Dee. 30, 1963) may be only the first case in point. But the effect is surely less the more cogent the analysis, and Dr. Ehsworth has distilled into 163 pages an extremely well-thought out and highly critical reexamination of the physical and chemical evidence available on these interesting systems. I t is important to point out in conclusion that "Volatile Silicon Compounds" complementa Professor Eaborn's "Organosilicon Compounds'' 11960), but stands separately from it and should certainly be of interest to anyone who finds this latter workuseful.

Chemistry in Nonoqueour Ionizing Solvents. Volume 4, Chemistry in Lower Fatty Acids and Derivatives

Edited by Gerhart Jander, Hans Spand m , and C. C. Addisa. Interscience Publishers ( a division of John Wiley and Sons, Inc.), New York, 1963. xv 313 pp. Figs. and tables. 17 X 24.5 cm. $12.

+

Properties of solutions in nonaqueous solvents have been studied since the beginning of this century and there is now an abundant literature on this subject which is both of academic interest and of

originated dy the late G. ~ & e r and by H. Spandm, in which our present knowledge

is presented concisely, is a timely and welcome addition to the literature. The volume under review deals with acetic acid, formie acid and some of their derivatives, acetic anhydride, acetamide, formamide and substituted amides. All ehaptern are in German, except the last section on amides, which is in English. The most extensive treatment in 129 pttges is that of acetic acid by K. Heymann and H. Klaus. Exteneive discussions with tables and figures are given of the following topics: physical properties, purification, solubility of inorganic and organic compounds, conductance, viscosity, transference numbers and ion mobility, potentiometry, acidity function, autoprotolysis constant, aeid-base equilibria and titrations, polarography, cryoseopy and solvalysis. This is the most complete review availilable on this subject. Although reference is made to a paper by Higuchi el al. (1956) it is regrettable that the formation constants of their set of indicrttors are not listed in a table. Also, neither photometric (e.g., the ingenious method of Higuchi, Rehm and Barnstein, Anal. Chem., 28, 1506 I19561 is not mentioned) nor thermometric end point determinations are reported. In general, the same order of treatment is maintained in the chapters dealing with acetio anhydride (69 pages) by H. Surawski, with acetamide (20 pages) by G. Winkler, and with formic acid (28 pages) by H. Knauer. It is unfortunate that the more recent studies by A. Popov and J. Marshall in formic acid are not included. The last part (30 pages) deals with formilmide and derivatives of amides by the well known expert L. R. Dttwson. An excellent review of conductance, ion mobilities, solubility and degree of dissociation is presented. Unfortunately, hardly anything is said about acid-base properties of the solvents and acid-base equilibria and titrations. Also the literature on polarography in these solvents is not reviewed. A subject index of 24 pages concludes this book. Although in some chapters s. more critical discussion, especidly of the older literature, might have been desirable, the authors deserve our gratitude for having made available a wealth of systematically presented information. The book, which undoubtedly will stimulate many readers to pursue further research in nonaqueous solvents, can be recommended without reservation.

and rendered into the ten languages. Unfortunately the latest standards are not used ("C, Kr light, etc.) for the defitions. A second extensive table lists the national units for 69 countries and gives conversion factors to the US., U.K. and metric systems. Lists of defining words (absolute, reciprocal, etc.) and prefixes (tera to pico) are also translated into the ten languages. Two complete indexes, one for Russian only, are provided.

W. F. K. Naturally Occurring Oxygen Ring Compounds

F. M. Dean, University of Liverpool, England. Butterworths, London, 1963. 661 pp. Figs. and tables. viii 16 X 25.5 cm. $24.95.

+

Among the nrtturdly occurring heterocycles, which constitute one-half of all natural products, oxygen heterocycles are fewer in number than the nitrogencontaining heteroeyoles and have received less attention in surveys both of natural products and of heterocycles. This book renreaents the first a t t e m ~ to t deal svstematically with the extensive chemistry of these oxygen heterocycles. Fifteen chaptera me concerned with the common classes of five- and six-membered oxygen heterocycles, such as furans, benzofurans, pyrans, unsaturated lactones, coumarins, chromans, chromens, chromonea, chromanones, xanthones, and flavonoid compounds. Two chapters deal with rings of other sizes, rings with two oxygen atoms, and compounds containing two fused oaygen-containing rings. Not all naturally occurring oxygen heterocycles are included: saturated bctones, 1,3benzodioxoles (i.e., derivatives of methyleuedioxybenzene), cyclic hemiscetds and hemiketals (e.g., carbohydrates), and compounds with rings containing both oxygen and nitrogen atoms have been arbitrarily excluded. The compounds discussed me almost exclusively of plant origin since only a. few oxygen ring eompounds have been found in animda. For each chss of compound, a general description of the structural characteristics and chemical properties is given, followed by a eatslog of specific compounds. For each of the latter there are presented the ocI. M. KOLTHOFP currence, synthesis, proof of structure, and, Uniuwaity of Minnesota often, biological properties. The find Minneapolk chapter is an excellent survey of biosynthesis of oxygen-contsining compounds. Although the emphasis is on oxygen ring Lexicon of International and National eompounda, numerous related types of Units compound me necessarily discussed, so that this chapter is of general interest as Compiled and arranged by W. E. an introduction to the theories of bioC h n , N. V. Philips Gloeilampensynthesis, the methods for determination fabricken, Eindhoven, Netherlands. of hiosynthetic pathways, and some of the American Elsevier Publishing Co., Inc., very convincing data which have been 76 pp. 13 X New York, 1964. vi obtained in support of hiosynthetic 19.5cm. 54.95. theories. Although the author states that his This book will be valuable for all who treatment of the field "is in no way exhave to translate units into or from the haustive, despite theinclusion of more than following languages: German, Spanish, two thousand references," the literature French, Italian, Dutch, Japanese, Polish, appears to be well covered through 1961. Portuguese, Russian, or Swedish. Three Some of the clmses of compounds discussed hundred terms are defined (in English)

+

Vol. 41, No. 9, September 1964

/

519

have been the subjects of much earlier review articles, and the five chapters on flavonoid compounds overlap Geissman'a hook, "The Chemistry of Flavouoid Compounds!' There is, however, no other hook covering the whole area, so that the hook will he valuable for reference even though it is not of general interest to oreanic chemists or teachers. The book

cessive turning of pages is required to correlate formulas with text. Two features, in addition to the chapter on biosynthesis, deserve specal comment. The chapter on anthocyanins provides a most interesting historical account of the development of the chemistry of this important elms of compounds. Second, the hook is of interest as a workbook in prohlems of elucidation of structure. For mast of the specific compounds discussed, sufficient data itre presented on products of degradation, reactions, and spectra to justify the assignment of structure. Hence the hook should he of use in courses on natural products not only as a reference hook on oxygen heterocycles hut also as a source of study problems in structural elucidation. W1~~1.04 R. RODERICK Abboft Lahoratorirs North Chicago, Illinois Optimum Seeking Methods Doughs J . Wilde, Stanford University, Stanford, California. Prentice-Hall, Inc., Englewood Cliffs, New Jersey, 202 pp. Figs. and tables. 1964. xiii 16 X 23.5 cm. $6.i5.

+

When viewed within its stated limitations this hook is notably successful. It concentrates on the experimental procedures that will find levels of single or multiple factors to produce an optimum response. The methods are specific, although not necessarily limited, to functions which are unknown in advance. The author states that no mathematics heyond "standard" calculus are required for understandine: the boak is intended

understanding of criteria for measuring a system's effectiveness. The hook fulfills all of these promises. The author's approach of sacrificing rigor for plausibility is notably refreshing, especially to the pragmatist. This approach willalso be appreciated by students who should develop s. better understanding of the process rather then memorimtion of theorems and proofs. As a reference the text covers the generalities of the various procedures and then provides basic references to which the reader may go to pursue the procedure in more depth. The pmcedures covered include Fibonacci Search, Golden Section Search, Methods of Steepest Ascent, Contour Tangents, Parallel Tangents, Pattern Search, Ratating Coordinates, and Stochastic Approximation Schemes. The book is attractively printed, easy to read, and the illustrations are

informative and complement to the text. This boak purports to he a text for undergraduates and a reference for the p r a c titioner. This it is and an admirable one; however, this does not mean that the book instructs one on "how to proceed." Because the author is a ~hemieaien~ineer, the book is supposed to be "interdisciplinarv." This is not so. The orientation is stkctly mathematicd. The book is then a text for undergraduates with nothing more than calculus, hut undergraduates who intend to pursue the mathematical aspects of some one of several possible disciplines. It will serve only as a survey work far any scientist who is interested in performing experiments which are motivated primarily by his own discipline. Rare indeed is the practicing experimenter who will he willing to start with this text and pursue the mathematical development of an analytiesl method through the references sited just so that he can perform the mechanics of anslyzing his experimental trials. This is not a criticism of the author or his hook; he does not say that this is a "method" book for the experimenter. However, the suggestion that it is interdisciplinary and aimed a t many diverse areas may cause disappointment. C. R. WEAVER Ohio AgrieuUural E z p e r i m l Station Wooster World List of Scientific Periodicals Published in the Years 1900-1960. Volume 1,A-E

Edited by Peter Brown, British Museum, and George Bwder Sfratton, Zoological Society of London. 4th ed. Butterwortha, Washington, D. C., 1963. 531 pp. 21.5 X 27 em. $84 xxv per three volume set.

+

The editors announce that this is the Iaat edition to he published. An slternative method of keeping this list up-todate has been adopted; namely, the puhlicetion of annual supplements of the "British Union Catalogue of Periodicals" by the National Central Library. The editorial work has been good. The reader is provided with lists of ahbreviations and also specific examples of typical entries. The explanation of these examples is clear and straightforward. From the point of view of usefulness to the non-British user, the limitation of library holdings to those in the United Kingdom is unfortunate. In the reviewer's opinion, this listing does not provide an advantage (to the chemist) over Chemical Abstracts' "List of Periodicals with Key to Library Files," 1961. The Chemical Abstracts' list includes 305 cooperating libraries, 50 of whieh are not in cantinental United States. On the other hand, a librarian hss pointed out that current lists of periodicals, such as "The Union List of Periodicals," do not have as large a numher of entries as does this World List. In other words, there is no comparable U.S. publication for the entire scientific field.

JOHN D. REINAEIMER College of Wooster Wooster, Ohio

Carl Wilhelrn Scheele: Apotheker, Chemike,, Entdecker Otto Zekert, Vienna. Wissensehaftliehe Verlagsgesellschaft m.h.H., Stuttgart, West Germany, 1963. 149 pp. Figs. 13 X 21 cm. 15.80 DM (approximately $4.)

Tho term "chemist" is still used in England to designate a druggist or apothecary as well as a. person who is engaged in or trsined in ehemistry. This usage is a living relic of the early period in the development of chemistry when most of its devotees earned their living in a pharmacy (chemist's shop). Quite a few of the eminent chemists of the late 18th and early 19th century were practicing apothecaries; they pursued chemistry (a minor profession) mostly as a sideline or even as an intellectual hobby. The most notable of the 18th century apothecary-chemists was C.W. Scheele. He was horn a t Stralsund (then a Swedish city) in 1742 and died in Koping, Sweden in 1786. Thus he spent his entire life in Sweden but his native language was German. He received no formal training in chemistry beyond what was needed for his professional needs, hut he early developed an irresistible and unquenchable urge to experiment in the chemical field. He had only the simplest equipment, his aveilahle supplies were limited mostly to what he could ohtsin with little or no outlay of money, and in addition he had to carry on his experiments during the evenings, holidays, and days off. Nonetheless, the number of his notable discoveries is truly astounding; during his lifetime they hrought him high honors; his name is included in every list of the foremost pioneers of ehemistry. "He brought to light more new substances of fundamental importance than any other chemist without exception." (Psrtington). The author of the short biography under review here has given a course on the history of pharmacy for many years at the University of Vienna. He began his intensive studies of Scheele's life and work many years ago; the fint of his many papers and hooks in this field was published in 1924. The resent hioeraohv nurnrly wwlwrq, 111&111s, p r u c ~ w m g clw~~,~sta : i d p l u i r w i h s . 'I%e WXI fiuws 1 11 ~ 1\1111d2 wc'r ottrul.,.tl. T h e s n _ ~ ~ u t 1l ~ ~ numerous illustrations augment the attractiveness of the well-printed volume. Useful appendixes provide explsnstions of the archaic terms, and present the scientific, political, and cultural setting in whieh Scheele accomplished his work. A three-page bibliography (mostly German, some English, and Swedish) is another good feature. A translation of this authoritative text into English would fill a gap in our too restricted supply of books dealing with our eminent chemical ancestors.

RALPAE. OESPER Uniuersily of Cincinnati Cincinnati, Ohio