Barbituric Acid
ivation from the German word Schliirrelbart (the bit or "beard" of a key, from L. berbe, beard) plus uric acid.
JAMES KENDALL University of Edinburgh, Edinburgh, Scotland
c.
HEMISTS must frequently have wondered what .. IS the orlgm of the peculiar name of this compound discovered by Baeyer (Ann. 127,199 (1863); and since the introduction of barbiturates into the field of medicinal products in recent years, I have received a number of inquiries from physicians on the question. The only suggestion that has been made in the literatureI am indebted to my colleague, Professor John Read, of St. Andrews for bringing it to my attention- is given in a book by Louis F. Fieser and Mary Fieser, "Organic Chemistry,'' D. C. Heath and Company, Boston, 1944, p. 247); i t runs as follows: The picturesque names of the compounds of the uric acid group for the most part were chosen by Wijhler and Liebig a t a time when i t was impossible t o envision structures and when the analytical method used for determining nitrogen was so subject to error as t o give misleading results. The oxidation product, allantoin, was so named because it was found t o be identical with a substance isolated from the allantoic liquid of cows, and its product of reduction, or hydrogenation. was named hydantoin. The product of nitric acid oxidation, alloxan, was thought t o eontaid the elementsof allantoin and o d i c acid. The further oxidation product, parabanic acid, impressed Wdhler and Liebig as a "new and peculiar acid;' both because of the unusually low hydrogen content and because it was found t o be converted by acid. NH9bases with meat ease t o another substance laxaluric . ~ CONIICOCOOH, the monoureide of oxalic arid); the name is derivcd from the Greek fioroboincin, to deviate. Baeycr's paper does not disclme the reason far his choice of the name barbituric acid. but so stresses his conception of this substance as the key compound in the series of related ureides as t o suggest the der~~~
~~~~
.
This explanation is certainly ingenious, but to me i t is not convincing since I obtained from the late Dr. L. H. Baekeland, during a visit he made to Edinburgh in 1937 to receive the honorary degree of LL.D., an alternative derivation which I shall attempt to put on record, so far as my memory serves, in his own words. Baekeland had the story first hand from his father-inlaw, Theodore Swarts, who succeeded Kekul6 in the chair of chemistry a t Ghent. Baeyer and Swarts were both research workers in Kekule's laboratory a t the time of the discovery. For their lunch the chemical st& regularly went to a nearby restaurant which was also the rendezvous of the officers of the local artillery garrison, and friendly relations had been established between the two groups. One day when the chemists entered, they found the officers already engaged in what was obviously a very special celebration, and were invited to join the party. When they asked the reason for the festivity, it was explained to them that this was Saint Barbara's Day, and Saint Barbara was the patron saint of gunners. After a time Baeyer mentioned in the course of conversation with the commanding officer that he also was feeling particularly happy that morning, because he had just discovered an important new chemical compound. "What are you going to call it?," asked the officer. Baeyer confessed that he had not given any thought to that point so far. "Well, what did you make it from?" was the next question. Baeyer told him that it was a derivative of uric acid. "A derivative of uric acid, and discovered on Saint Barbara's Day," exclaimed the officer, "its name shall be barbituric acid!" A toast was immediately drunk to the newly christened substance, and barbituric acid it has been called from that moment.
