Ab initio investigation of the fragmentation of 5,5-diamino-substituted 1,4,2-oxathiazoles

Robert J. O'reilly, Leo Radom

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The mechanism for the fragmentation of 5,5-diamino-1,4,2-oxathiazole derivatives has been studied at the CCSD(T)/6-311+G(3df,2p)//MP2/6-31 +G(2df,p) level of theory. The calculations suggest that the fragmentation occurs via a stepwise process involving the formation of polar intermediates that lie in shallow potential wells. We find a large thermodynamic driving force for fragmentation, which together with a weakening of the C-S bond through electron donation by the amino substituents provides the impetus for a low-barrier fragmentation.

Original languageEnglish
Pages (from-to)1325-1328
Number of pages4
JournalOrganic Letters
Volume11
Issue number6
DOIs
Publication statusPublished - Mar 19 2009

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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