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

Verónica Jiménez, Joel B. Alderete

Resultado de la investigación: Article

42 Citas (Scopus)

Resumen

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.

Idioma originalEnglish
Páginas (desde-hasta)1-7
Número de páginas7
PublicaciónJournal of Molecular Structure: THEOCHEM
Volumen775
N.º1-3
DOI
EstadoPublished - 13 nov 2006

Huella dactilar

tetrazoles
Triazoles
Protonation
Gases
vapor phases
tautomers
Solvation
Discrete Fourier transforms
Free energy
solvation
Hydrogen
Permittivity
Chemical activation
free energy
activation
permittivity
Molecules
shift
hydrogen
1H-tetrazole

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

Citar esto

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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.",
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Complete basis set calculations on the tautomerism and protonation of triazoles and tetrazole. / Jiménez, Verónica; Alderete, Joel B.

En: Journal of Molecular Structure: THEOCHEM, Vol. 775, N.º 1-3, 13.11.2006, p. 1-7.

Resultado de la investigación: Article

TY - JOUR

T1 - Complete basis set calculations on the tautomerism and protonation of triazoles and tetrazole

AU - Jiménez, Verónica

AU - Alderete, Joel B.

PY - 2006/11/13

Y1 - 2006/11/13

N2 - 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.

AB - 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.

KW - Azoles

KW - Complete basis set calculations

KW - Protonation

KW - Tautomerism

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U2 - 10.1016/j.theochem.2006.06.010

DO - 10.1016/j.theochem.2006.06.010

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