/tory behind the /tory The 19th Century Purity of American Chemicals Leonello Paolonl GNppo di Chimica Teorica The University of Palerrno 90123 Palerrno, italy
The svnthesis of 1.3.5-triazine C*H.N. " " " was first renorted in 1954 i y ~ r u n d m a &and Kreutzberger (I). ~ c c o r i i nto~ the authors, its ". . . formation from the adducts of hydrocyanic and hydrnchloric acid occurs so easily and under certain conditions with such good yields.. .", that one may wonder why the compound has not been reported before. Reasons for the failure of the earlier attempts are given in a successive paper (2). The discovery of s-triazine, hhwever, goes back to 1895and is credited by the same authors to John Ulrich Nef, Professor of Chemistry at the University of Chicago. In a footnote to their paper (I) Grundmann and Kreutzbereer exnlain that Nef failed to obtain the correct molecular weGht of'the compound and assigned to i t the C2H2N2formula which led to a wrong structure. This is how it happened,
394
Journal of Chemical Education
edited by '
JOHNH. WOTIZ
Southern Illinois University Carbondale, Illinois 62901
in Nefs own words (3): "The determination of molecular weight in a benzene solution bv two observations of the freizing point gave a molecular weight of 64 (calculated 34). It is likely that the rather high value that we found devendtd on the [purity of the] benzene we used; it was by accident that only American benzene was available in the laboratory. . .". He expressed then the intention of repeating the determination by a vapor density measurement (Hofmann's method) hut apparently never carried i t further, and s-triazine remained unrecognized for about 60 years (4) because of the [assumed] poor quality of American benzene in 1895.
Literature Cited (1) Gmdmaon, C. and Kreutsbeqer, A,, J Amer Chem. Sac. 76.632 (1954). (2) Orundmann, C. and Kreutrberger, A,, J. Amer Chem Soe, 76,5616 (1954) 131 Nef. J. U..Ann.. 287.265 118951: ouotation from on. 338-339. iri T&& ~i& to its hadngk R m s d e by H. and A. R ~ Z ~ U ~ , Compfas Rendues Aced. Sci. Paris. 89,310 (1879). who reported to have isolated it from thepolymeriematerisl prepared fromanhydrous hydcoeyanicacid by addition o f s small amount of dry KCN. Although some of the chemical propertie. described or sumeientother dafa t h e oir-trisline,theydonotgive ame~tingpoint for identification. Thia work is also quoted by Nef (ref, 3, p. 317). who hmever had seen only it3 summary in Bar 12,2162 11879).
