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Heterocyclic Chemistry Physical

Methods

Chemistry.

in Heterocyclic

A. R. KATRITZKY, edi­

tor. Vol. 1: xi + 346 pages; Vol. 2: xi 4- 398 pages. Academic Press, Inc., I l l Fifth Ave., New York 3, N.Y. 1963. Vol. 1, $12; Vol. 2, $14. Reviewed by Dr. Robert C. Elderfield. Dr. Elderfield is professor of chem­ istry at the University of Michigan. These two volumes seek to fill a gap which is felt to exist because of a lack of treatment of the application of physical methods to heterocyclic com­ pounds in most reviews on the gen­ eral subject of application of physi­ cal methods to organic compounds in general. Although there is no dearth of reports of investigations with hetero­ cyclic compounds wherein a variety of physical methods have been em­ ployed, the foregoing statement is probably true· in essence. The main value of these volumes is found in the assembly of considerable data in one place, although certain rather critical omissions were noted. The several chapters are written by ex­ perts in the various areas and, in gen­ eral, a uniform style of presentation has been adopted. Each chapter carries an introduction dealing with the general theoretical aspects of the subject treated and then continues with a survey of the literature in which the method has been applied to heterocyclic systems. These intro­ ductions are quite variable. The opening chapter on ionization con­ stants is unduly long and for the most part is a repetition of material with which a reader competent in basic physical chemistry should be familiar. At the other extreme is the very cur­ sory treatment of the solubility phenomenon. A useful feature of the volumes is inclusion of selected gen­ eral references in most chapters. In Vol. I, ionization constants and their use in connection with hetero­ cyclic chemistry are discussed in con­ siderable detail with a critical evalua­ tion of the reliability of the data by Adrien Albert. The voluminous tables contain a wealth of data. Some omistions were noted, such as the work of Phillips on the 8-hydroxyquinolines.

John Ridd provides a critical discus­ sion of "heteroaromatic reactivity" as applied to electrophilic and nucleophilic substitution. Although the theoretical treatment is not exhaustive, a critical comparison is made between the ττ-electron, frontier electron, and localization energy treatments as pro­ viding bases for reactivity indexes. A necessarily very brief discussion of x-ray diffraction studies of heterocyclic compounds is given by W. Cochran. The chapter on solubilities might well have been omitted, since, aside from providing a collection of data, it con­ tributes little that could not have been predicted on the basis of general con­ siderations. To a somewhat lesser ex­ tent the same applies to the treatment of dipole moments of heterocycles. Probably the most useful chapter in Vol. I is that written by J. Volke on electrochemical properties in solution. The collections of selected standard oxidation reduction potentials and polarographic half-wave potentials provide a convenient reference list. The discussion of applications of elec­ trochemical methods will serve a use­ ful purpose in calling attention to the advantages to be gained from applica­ tions of these tools to a variety of problems. Vol. II begins with a rather com­ prehensive chapter on electronic spectra by S. F. Mason. The theoreti­ cal aspects are treated in somewhat greater detail than in other chapters. In the discussion of applications to heterocycles several omissions were noted; for example, the fundamental study of the spectra of the hydroxypyridines of Specker and Gawrosch. The general tone of the chapter reflects the primary interest of Mason as a spectroscopist; the organic chemist may well wish for greater emphasis on strictly chemical behavior as derived from spectrographic data. The chemi­ cal implications concerning the struc­ tures and properties of the amino quinolines arising from the definitive work of Steck and Erving, for ex­ ample, are not discussed. There seems to be no reason, other than to call attention to the method, for inclusion of a chapter on nuclear quadrupole resonance. The very scanty applications to heterocycles and the experimental difficulty as well as

problems of interpretation of the data combine to make this technique of little value to the organic chemist. For different reasons, the same may pos­ sibly be said of the chapter on nuclear magnetic resonance spectra by R. F. M. White. This technique is so well known and so widely used that the necessarily brief treatment seems superfluous in view of the availability of a number of more definitive works. Assembly of the available data is of help, but, unfortunately, space limi­ tations prohibited inclusion of but a very minor amount of material on alkaloids from which most of the in­ formation on heterocycles has come. The longest chapter (179 pages and 985 references) on infrared spectra by A. R. Katritzky and A. P. Ambler is probably the most useful in the vol­ ume. The vast amount of collected data provides a valuable supplement to those found in works such as that of Bellamy. In summary, the emphasis, in gen­ eral, throughout the volumes is so variable as to render them of some­ what doubtful value. The practicing organic chemist may find many sec­ tions of slight day-to-day utility and the physical or theoretical chemist may have recourse to more definitive treatises. The collected data will, however, be of some help in avoiding literature searches, but, again, the cov­ erage does not seem to be exhaustive. The composition and typography are

good.

Food Preservation The Technology of Food Preservation. Rev. éd.

NORMAN W. DESROSIER.

ix + 405 pages. Avi Publishing Co., Inc., P.O. Box 388, Westport, Conn. 1963. Domestic $9.50; foreign $10.50. Reviewed by Dr. D. M. Doty. Dr. Doty is director of research and education at the American Meat Institute Foundation, Chicago, III. This book, as did the first edition, includes a great amount of very valuable information assembled into one publication. Unfortunately the quality of the reporting is not concise and critical. Furthermore, the author has covered some areas very completely and is current in his presentation of the information, whereas in other areas the coverage is rather haphazard and not enDEC.

2 3,

196 3 C & E N

47

tirely u p to date. This criticism a p ­ plies particularly to sections covering meat preservation. It is obvious that t h e book was not carefully proofread because there are numerous errors in exact names. For example in the preface B. S. Schweigert is referred to as B. E . Schweigert. In some instances the author has ob­ viously accepted advertising claims of equipment manufacturers as factual without critical examination of the in­ formation upon which such claims are based. In several cases the author has made flat general statements that d o not apply in specific situations. For example, on p a g e 2 2 7 t h e author states "Moisture accelerates oxidative rancidity." This statement is not even generally true since under most condi­ tions oxidative rancidity is retarded b y the presence of moisture. T h e lack of care in editing and pub­ lishing is exemplified b y the fact that some tables are numbered while other equally long tables in the text are not numbered. Despite its shortcomings there are several excellent sections in t h e book. Chapter 9 on Chemical Additives is particularly good. It is unfortunate that the wealth of information included in this book is n o t more critically pre­ sented so that the reader could b e sure that t h e material as quoted represents the most valid and current thinking available on all subjects covered.

New Periodical High Temperature (Teplofizika vysoa journal of t h e kikh temperatur), Soviet A c a d e m y of Sciences, is n o w available in English and will b e dis­ tributed b y t h e American Institute of Physics, 3 3 5 East 45th St., N e w York 17, N.Y. Volume 1, N o . 1, which ap­ peared in t h e U.S.S.R. in September, will b e mailed in January. It will b e published b y Consultants Bureau in cooperation with AIP. Rates are: six issues annually ( 1 0 0 0 p a g e s ) , $ 5 0 ; 1 9 6 3 volume of three issues, $ 2 5 ; special combined subscription ( 1 9 6 3 64), $70.

NEW BOOKS Advances in Analytical Chemistry and Instrumentation.

Vol. 2.

CHARLES N.

REILLEY, editor, vi + 408 pages. In­ terscience Publishers, Inc., 605 Third Ave., New York 16, N.Y. 1963. $15. Attempts to translate significant develop­ ments of recent years in analytical chem­ istry into everyday working knowledge and practice. 48

C&EN

D E C . 2 3, 196 3

Advances in Glass Technology.

Part 2.

FREDERICK R. MATSON, G U Y E. R I N -

DONE, editors. xvii -j- 410 pages. Plenum Press, Inc., 227 West 17th St., New York 11, N.Y. 1963. $15. Additional papers from the 6th Interna­ tional Congress on Glass held July 1962 in Washington, D.C., by International Com­ mission on Glass. Atlas of Electron Spin Resonance Spectra. YA. S. LEBEDEV, D . M. CHERNIKOVA, N. N. TIKHOMIROVA, V. V. VOEVODSKII.

229 pages. Consultants Bureau Enter­ prises, Inc., 227 West 17th St., New York 11, N.Y. 1963. $15. Said to be of interest to structural and analytical chemists, biologists, biophysicists, biochemists, and spectroscopists. Biochemical ALSTON,

Systematics. B.

L.

TURNER,

RALPH xii

+

E. 404

pages. Prentice-Hall, Inc., Englewood Cliffs, N.J. 1963. $13.25. Attempts to answer the question, To what extent does the occurrence of similar sub­ stances in different plants indicate the degree of their relationship? Gives a critical appraisal of the present applica­ tions of biochemistry to systematics and a consideration of future possibilities. Boron Hydrides. W. N. LIPSCOMB, ix -f- 275 pages. W. A. Benjamin, Inc., 2465 Broadway, N e w York 25, N.Y. 1963. $14. Monograph covers principles of structure and reactions of the boron hydrides. Calculations

in

the Paper

D A L E S. DAVIS.

Industry.

231 pages.

Franklin

Publishing Co., Inc., Palisade, N.J. 1963. $9.80. Gives roundup of calculations performed in pulp and paper industry; purpose is to save time and effort for paper chemists, engineers, and technicians in charge of operation, production, control, and re­ search. Chemical

Constitution

Activity.

3rd ed.

and Biological W. A.

SEXTON.

xxviii + 517 pages. D . Van Nostrand Co., Inc., 120 Alexander St., Princeton, N.J. 1963. $19.75. Written primarily for use of chemists and biochemists in industry, especially the pharmaceutical and crop protection in­ dustries. Also recommended to those in the academic world. The Chemical Industry: Perspectives.

Viewpoints and

CONRAD BERENSON.

Χ

-f- 426 pages. Interscience Publishers, Inc., 605 Third Ave., N e w York 16, N.Y. 1963. $10. Book's purpose is to provide insights into commercial activities of chemical process industries in order more effectively to solve their business problems. The prin­ cipal problems are in marketing and management. Chemical Infrared Spectroscopy. Techniques.

Vol. I.

W. J. POTTS, JR. xvi -{-

322 pages. John Wiley & Sons, Inc., 605 Third Ave., New York 16, N.Y. 1963. $8.50. Practical guide to theory and experimental techniques by which infrared spectros­ copy is applied to solution of chemical problems. Chromatographic Methods. R. STOCK, C. Β. F. RICE, viii + 206 pages. Reinhold Publishing Corp., 430 Park Ave., New York 22, N.Y. 1963. $10. Book aims to present a short account of techniques in current use, with emphasis on paper and gas chromatography. Concepts in Photoconductivity and Allied Problems.

ALBERT ROSE,

Χ -f

168

pages. Interscience Publishers, Inc., 605 Third Ave., N e w York 16, N.Y. 1963. $5.95. Contents formed part of a course on Electronic Processes in Insulators given at Princeton, 1961-62. Corrosion Resistance of Metals and Al­ loys.

2nd éd.

F. L. L A Q U E , H. R.

COPSON, editors, xii -f 712 pages. Reinhold Publishing Corp., 430 Park Ave., New York 22, N.Y. 1963. $21. Replaces the original edition published 30 years ago which became internationally known as "McKay and Worthington." Expected to become leading treatise on corrosion in English. A Course in Process Design. SHERWOOD,

ix -f

Press, Cambridge $6.00.

THOMAS K.

254 pages.

42, Mass.

MIT

1963.

Critical Review of the Analytical Methods of the Titanium, Vanadium, and Chromium Transition Element Groups. ROBERT

Z.

BACHMAN,

CHARLES

V.

BANKS, V + 67 pages. Macmillan Co., 60 Fifth Ave., New York 11, N.Y. 1963. $3.50. A Dictionary of Biological Terms.

I. F.

HENDERSON, W. D . HENDERSON. ed. by J. H. KENNETH, xvi +

8th 640

pages. D . Van Nostrand Co., Inc., 120 Alexander St., Princeton, N.J. 1963. $12.50. Contains pronunciation, derivation, and definition of terms in biology, botany, zoology, anatomy, cytology, genetics, embryology, physiology. Digital Computer Programs for Physical Chemistry.

Vol. I.

PAUL A. D . DE

MAINE, ROBERT D . SEAWRIGHT.

xxiii

-f 423 pages. MacMillan Co., 60 Fifth Ave., New York 11, N.Y. 1963. $18. Presents integrated system of individual programs for processing experimental information rapidly and precisely. The Electron.

ROBERT ANDREWS M I L -

LIKAN. lvii + 268 pages. University of Chicago Press, 5750 Ellis Ave., Chicago, 111. 60637. 1963. Cloth $6.00; paperback $2.45. Reprint of classic work first published in 1917. Enzyme Chemistry of Phenolic Compounds. J. B. PRIDHAM, editor, ix -f 142 pages. Macmillan Co., 60 Fifth Ave., New York 11, N.Y. 1963. $7.50. Proceedings of the Plant Phenolics Group Symposium, Liverpool, April 1962. Food

Processing

Operations.

Vol. 2.

J. L. HEID, MAYNARD A. JOSLYN.

xi

-f- 594 pages. Avi Publishing Co., Inc., P.O. Box 388, Westport, Conn. 1963. Domestic $19.75; foreign $20.75. Gask-O-Seal Handbook. 120 pages. Parker Seal Co., 10567 Jefferson Blvd., Culver City, Calif. 90232. 1963. $5.00. High Pressure Physics and Chemistry. Vols. 1,2. R. S. BRADLEY, editor. Vol. 1 xi -f 444 pages; Vol. 2 xii -f- 361 pages. Academic Press, Inc., I l l Fifth Ave., New York 3, N.Y. 1963. Vol. 1 $15.50; Vol. 2 $12.50. Said to provide comprehensive and advanced study of high pressure science. How

to Select

EDITH SANDS,

Executive

Personnel.

xvi -f 215 pages.

Rein-

hold Publishing Corp., 430 Park Ave., New York 22, N.Y. 1963. $9.75. Book was written with cooperation of 82 of the nation's largest enterprises.