2,4-Dithiouracil tautomers: Structures and energies

Jerzy Leszczyński, Koop Lammertsma

Research output: Contribution to journalArticlepeer-review

55 Citations (Scopus)

Abstract

Six tautomers of 2,4-dithiouracil have been studied by using ab initio theory. All correspond to energy minima at the HF/3-21G(*) level. Their stability order has been determined by using the MP2/6-31G*//3-21G(*) approximation with inclusion of zero-point energy corrections. The dithione tautomer 1 has the global minimum energy. Its energy difference with the second most stable structure, the dithiol tautomer 2, amounts to only 28 kJ mol-1. Substitution of oxygens by sulfur atoms in uracil may enhance the probability of its biologically important process of spontaneous mutations by a factor of 103.

Original languageEnglish
Pages (from-to)3128-3132
Number of pages5
JournalJournal of Physical Chemistry
Volume95
Issue number8
DOIs
Publication statusPublished - 1991
Externally publishedYes

ASJC Scopus subject areas

  • General Engineering
  • Physical and Theoretical Chemistry

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