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Paper | Regular issue | Vol 24, No. 11, 1986, pp.3129-3141
Published online, 1st January, 1970
DOI: 10.3987/R-1986-11-3129
Mechanism of H/D Exchange in 5-(p-Nitrobenzyl)barbituric Acid

Misa V. Jovanovic* and Edward R. Biehl

*Department of Chemistry, Southern Methodist University, P.O. Box 750314, Dallas, TX 75275-0314, U.S.A.


Title compound 1 and related systems exist in DMSO solution as a tautomeric mixture of enol and keto forms which were easily identified by 13C nmr spectroscopy. Base-catalyzed H/D exchange of 1 occurs at both the C-5 and the methylene group. A mechanism to account for the novel H/D exchange at methylene position is proposed.