TRILINEAR CHART OF NUCLEAR SPECIES
The magnitude of the effort expended in the prepnration of Elsevier is indicated by the report that the editorial staff has WilIiam H. Sullivan, Scientific Director, Naval Radiolcqical been increased from about five members a t the end of the war to D&nae Laboratory, San Francisco 24, California. John Wiley h some thirty-five members and that the journals systematically Sons, Inc., New York 1949. iii 22 pp. 21 X 26.5 cm. searched now amount to about 460. Another indication is the $2.50. appearance in the Remeil dea Trauauz Chirnipue des Paya-Baa c of all known nuclear species is pre- for 194748 of five papers by J. van Alphen of the Elsevier staff A o n n s ~ ~arrangement sented in which the number of neutrons of the nuclide as the reporting experimental investigations of "Discrepancies in the , o.. * . conflictine data for the m. u. of a-na~hthvl,~ ordinate is plotted against the atomic number of the nuclide as Literature" (e. absciswt. The ordinateabecissa angle is reduced to 60" so that amine pwate; x suppowd condensntion produet from mmphorthe whale chart is recorded an a single, continuous strip. Each mime wnd rhloml). The bold enterprise in rlae dorunwnt:ltion nuolear species is designated by a multicolored hexagon. The of organir chcmical literature derives slwugth from rponsorsl~lp colors in the hexagonal field indicate whether the nuclide is by a publishing firm famed mnce the seventeenth century for naturally occur~ingor artificially produced and, if unstable, its advances in printing methods and for international exchange of type of emission. The physical constants on the chart include: knowledgein the fieldof natural sciences. The workisconducted relative natural isotopic abundance, atomic mass, nuclear spin, unostentatiously in the quiet of the majestic city of Amsterdam. The two volumes under review are the first of a series of seven magnetic dipole moment, slow neutrou cross-section, half-life, mode of disintegration and type of radiation, branching ratio, parts of a complete treatise on Naphthalene Compounds to comenergy of radiation, and a critical estimate of the degree of cer- prise about 47W pages. Part I includes naphthalene (47 pages tainty of element andnuclson number assignment for eaoh nuclear for the hydrocarbon proper), its many alkyl, sryl, and hydro despecies; the absorption and total slow neutron cross-section for rivatives, and derived halogen compounds; Part I1 includes of nnphindividual elements; and the U'" fission yield value for masses nitro-, nmino- and other nitrogen contnit~ingdcrivnti~er crf the srnw. between 72 and 162. Provisions are made for entering new tlbnlcne, trrralin, decqlin, and other h,v~lrowrlon~ One useful fearure of the nrranarrnrrrt of mkterial i.; that d l nuclides as they are found. This well designed chart should be of great value ta workersin the known stereoisomeric hydro derivatives of a given naphthavarious nuolear fields as it presents a compact and portable com- lene are included in the same volume as the parent aromatic nendium of the more useful nuclear urouerties. The chart, when substance. Another is the inclusion of ingeniously conceived extended in lull, will wn.r ns an cvccllent renrhing uirl, l~wnusr charts, showing, for example, the course of the sulfonation of surh plenommn ns the line of nuclear xnhiliry, the rel~lrionsl~ipa 8-naphthylamine, the several methods developed for the synnnamu atomic number, xiumber of neutrons, and m w nundwr, thesis of euddene and of cadalene, the structures and numbering systems of 24 heterocyclic nuclei referred to in the section on and mirror nuclekcm be vividly demonstrated. naphthylrtmines. The inclusion of summary tables of isomers EDWARD GOLDBERG also appeals to me as a thoughtfully conceived and very useful SERIPPB I N B ~ ~ Tor IO OCE*NOBR*PHT N feature. By reference to either the subject or formula index one LA JOLLA. CALTPOBNIA can locate tables listing the structures and melting points of the dinitro-, diamino-, dimethyl-, dichloro-, and dibromonaphthalenes; i t is interesting that all ten isomers are known in each of ELSEVW'S ENCYCLOPEDIA OF ORGANIC CHEM- these five series. The conveniently arranged tables stimulate ISTRY. VOL. 12B, NAPHTHALENE. PART I, HYLIRO- thought on the interplay of two features of structure that seem to CARBONS AND HALOGEN COMPOUNDS. PART 11, determine relative melting points: &substituted naphthalenes NITROGEN COMPOUNDS. invariably melt higher than the or-isomers; symmetry of strucF. Radf, Editor, Elsevier Publishing Company, New York-Am. tures seems to favor high-melting character. Thus the 2,B-isomer 366 pp. 17.5 X 26 cm. usually has the highest melting point, and the I,& and 2,3sterdam, 1948, 1949. Part I. u x Subscription price, $24. Serial price, $28. Single volume isomers are also high-melting. Another table lists 36 halogeno783 pp. 17.5 X 26 cm. Suh- mononitronaphthylamines; another lists 86 l-arylazonaphthaprice, $32. Part 11. Iwvi scription price, $48. Serial price, $56. Single volume price, lenes, each with the structural and empirical formula, melting point, color, mode of formation, and references. Some of the $64. tables are of particular use in the identification of unknowns. IN PREVIOUS reviews for Tars JOURNAL (1949) and for the One lists 69 additional complexes of naphthalene; another gives Jmcnzal o j the American Chemical Society (1948), I expressed high the melting points, appearance, and other properties of the orpraise of the &st three volumes of this monumental lexicon in naphthylurethanes of 191 alcohols and phenols. Another feature is the inclusion where appropriate of such English that eventually will record the structures, properties, methods of formation, and reactions of the thousands of organic special items ss discussions of the physiological actions of 8compounds of all known types. The two new volumes seem to naphthylamine, commercial applications of deceliu, the bond me to have the same high character as the others with respect to structure of naphthalene. An example of the type of useful new organization, scholarship, scope, accuracy and quality of com- information to he gleaned from study of the work is the citation position and printing. In addition to these qualities, Elsevier from a recent Russian publicetion of the condensation of tetraliu has achieved a. noteworthy schedule of publication: each volume with butadienein the presence of sodium to 1-ALbutenyl-1,2,3,4,covers the literature up to approximately five years prior to its tetrahydronaphthalene and cyclization of the substance to a appearance. Thus, the volume Naphthalene, Part 11, bears the perinaphthane derivative. It seems to me that the value of this excellent compendium publication date 1949 and includes references to December 31, 1944. A8 further means of keeuine .. the Encvclouedia uu to could be enhanced by inclusion of more information concerning cl:,rc the l>nWi*hrrplans to bring our a lwiclmi supplement yields. The edtiors have been overconservative, I think, in ten yeam after nppcnrsnce of each main volune; thr nrcumu- limiting entries under the heading "Preparation" almost exIated new material will thus ronsrlrutr. x rixlglc.wpplrr~lcnrro the clusively to procedures published in "Organic Syntheses,', "Organic Reactions," or the monograph by Fierz-David and Blangey. entire work.
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JOURNAL OF CHEMICAL EDUCATION
350 !%rely the original liternrurc contains may). ctther reliable procedures that have been carefullv worked our, and ofren checkcd in more than one laboratory. I grant that a decision between the categories "Formation" and "Preparation" is a difficult one, but feel that expansion of the second category is a desirable goal. In any case the situation would be improved by freer citation of yields. As it stands, one finds no preparative procedure given for many fairly common compounds and is often confronted with a mass of references to reactions of formation with no indication of which ones have preparative application or proceed to an extent significant of directive eEectects or reaction mechanisms. If the user plans to prepare a batch of material he probably will want toresd the papersin any case; if heseeks quick infarriation for citation in a paper or book, or for solution of a problem, he would much refer to have all available information about the yields. For kxamp~e,no preparative method is indicated for 1- or Zphenylnaphthalene, and some twenty reactions are listed by which each hydrocarbon is formed with no indication of yields other than an occasional comment such as "in smdler yield," "trace!' How good are the other routes? Which ones could be considered for rapid preparation of comprtrison samples? One mode of formation of 2-phenylnaphthalene cited is hy the action of acids on phenylethyleneglycol; actually the mrtster experimentalist Zincke in 1881 reported a yield of 60-70 per cent of very pure hydrocarbon, and Carter and Van Loon in 1938 reported a yield of 78 per cent. The later authors obtained 2phenylnaphthdene in 80-85 per cent yield by acidolysis of the easily prepared a-amino-8-methoxy-8-phenylpropionieacid and describe this as "a satisfactory preparative method for the hydrocarbon." Another entry in Elsevier states that the hydmcarbon was obtained from 2-( A~-cyclohexenyl)-naphthalene "on heating with S a t 240-60""; the statement might have included the comment "(24 per cent yield from 8-bromomphthalene)," for this would indicate the entire route and success of the synthesis. In some instances, for example, 8-nitro-l-naphthylamine, the citation of yields is entirely adequate, but I feel that general strengthening in this direction is desirable. There is both theoretical and practical interest in the ratio of isomem formed on mononitration of 1-nitronaphthaleneand of tetralin; approximate ratios are known and should be included. 1-Amino- and l-bromotetralin are useful intermediates whose preparation has been studied in several laboratories. and ~renarative~moedurrs
with reactions of the methane p u p ) now includes simple ole6ns and benzene. The test reactions of the aldehydes are now combined in one experiment. The monosaccharides and disaccharides are considered together in Experiment 26. The preparation of 2,4dinit~rophenyIhydrazonesas derivatives of aldehydes and ketones is a very welcome addition. Another is the extremely useful, rapid prooedure for acetylrttion of certajn amines in an aqueous medium. Nine new preparative experiments have heen added. Perhaps the most instructive are methyl n-butyl ether, a Williamson synthesis; stearamide, the preparation of an amide via the acyl chloride state; phenacetin, an important drug; terb butylbenzene, an adaptation of the Friedel-Crafts reaction; 2-methyl-2-pentanol, an diphatic Grignard synthesis; DDT, an important insecticide. A few of the most attractive features of this manual are the questions a t the end of each experiment, the complete, explicit directions, the well-balanced choice of test tube and preparative experiments, and the section on materials and reagents required for each experiment. The reviewer feels that the perforations in the pages of the book are unneceasrtry. Obviously, these allow convenient removal of certain pages by the student, presumably for insertion in a laboratory notebook. This practice seems unwise since it destroys, a t least partially, a potential reference book and, also, causes the laboratory notebook to assume the character of a scrapbook. An interesting change in the text is in the spelling of the common verb, distill (previously, distil). The text appears to be free of errors, since only two minor typographical slips were noted. The reviewer cannot refrain from using this opportunity to recommend this volume most highly. It is without a doubt one of the most practicable mrtnualls for elementary courses in organic chemistry. DONALD C. GRECG UNIVERWT~ 0. VERMONT
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STRENGTH OF PLASTICS AND GLASS
R. N. Howard. Research Chemist, Petrocarbon, Ltd., England.
Cleaver-Hume Press, Ltd., London, England-Interscience Publishers, Inc., New York, 1949. viii 245 pp. 108 diagrams. 16 plates. 14 X 23 cm. $5.50.
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LABORATORY EXPERIMENTS IN ORGANIC CHEMISTRY
Tms baok treats the mechanical properties of plastics and glass. It presents the facts clearly and interestingly and gives a. good over-all view of the subject. The various theories are treated sketchily but with references so that the original articles e m be consulted. The terminology is standard and the book should prove very useful to those seeking an orientation in the field of plastics and glass.
Roger Adorns, Professor of Chemistry, University of IUinois, Urbana, Illinois, and John R. Johnson, Professor of Chemistry, Cornell University, Ithaca, New York. Fourth edition. The Macmillan Co., New York, 1949. xiv 525 pp. 30 figs. 10 tables. 14 X 21 cm. $3.25.
HENRY EYRING
U~rv~nsm OPr UTAH SALTL ~ s a CITT. UTAB
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T m foudh edition of this well-known laboretory manual is, in essence, quite similar to the third edition. It contains several distinct improvements, not the least being its more attractive format. Although the adjective, elementary, has been dropped from the tifle, this revision, as before, is a manual for beginning students. Some of the more notable additions and rearrangements should be mentioned. The text incorporated in the 6rst eight experiments on laboratory operations has been expanded. Two of the several alterations in this section of the manual are: (1) the determination of boiling points precedes the determination of melting points, (2) a short discussion of sublimation is added to the section on crystallization. Experiment 9 (formerly dealing
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ELECTRON MICROSCOPY
Ralph W. G. Wyckoff, Laboratory of Physical Biology, Experimental Biolagy and Medicine Institute, National Institute of Health, Bethesda, Maryland. Interscience Publishers, Inc., New York, 1949. 248 pp. 202 illustrations. 16 X 24 om. $5. 'l'n~sattractive Im,k will be u~clcomeduut only by time working in the field of rlwtron microaeopy, hut d30, and mninlp, by clreniistq and i,ihgistr at large who wi41 to have a aummnrv of the present state of the art and science of electron m i o r ~ s c ~ ~ ~ , with particular regard to the kinds of problem which now can be and are being attacked with the electron microscope. Four early chapters, comprising almost half of the book, are
