Complete basis set calculations on the tautomerism and protonation of triazoles and tetrazole

Verónica Jiménez, Joel B. Alderete

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)

Abstract

Highly accurate methods CBS-4M and CBS-QB3 and standard DFT/B3LYP calculations were employed to study the tautomerism and protonation of triazoles and tetrazole in gas phase. Throughout this analysis, a remarkable agreement between CBS methods and B3LYP/6-311++G(d,p) calculations was observed. To account for solvation effects on tautomer stabilities and protonation pathways, Polarizable Continuun Method (PCM) calculations at the B3LYP/6-311++G(d,p) level were performed considering four different dielectric constants ranging from ε = 2 to ε = 25. Calculated activation free energies for 1,2-hydrogen shifts suggest the existence of tautomeric equilibriums between the protonated forms of 1,2,3-triazole and the neutral forms of tetrazole as an explanation for the protonation of these molecules in gas phase and solution.

Original languageEnglish
Pages (from-to)1-7
Number of pages7
JournalJournal of Molecular Structure: THEOCHEM
Volume775
Issue number1-3
DOIs
Publication statusPublished - 13 Nov 2006

Keywords

  • Azoles
  • Complete basis set calculations
  • Protonation
  • Tautomerism

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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