Tautomerism of 2- and 4-Thiouracil. Ab Initio Theoretical Study

Andrzej Leś, Ludwik Adamowicz

Research output: Contribution to journalArticlepeer-review

63 Scopus citations


Ab initio quantum mechanical studies on tautomerism are extended to the 2-thiouracil and 4-thiouracil molecules. We considered the protomeric tautomerism in vacuum and conclude that for both species the oxo-thione forms should prevail in full agreement with recent experimental matrix isolation studies. Surprisingly, the next most stable structure appears to be the hydroxy-mercapto form. The relevance of the relative stability order of 2-thiouracil and 4-thiouracil to the tautomerism of various derivatives is discussed. Major features of the vibrational spectra of various tautomeric forms are presented and compared with the experiment.

Original languageEnglish (US)
Pages (from-to)1504-1509
Number of pages6
JournalJournal of the American Chemical Society
Issue number4
StatePublished - Jan 1990

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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