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 original | English |
|---|---|
| Páginas (desde-hasta) | 1-7 |
| Número de páginas | 7 |
| Publicación | Journal of Molecular Structure: THEOCHEM |
| Volumen | 775 |
| N.º | 1-3 |
| DOI | |
| Estado | Published - 13 nov 2006 |
Huella dactilar
ASJC Scopus subject areas
- Biochemistry
- Condensed Matter Physics
- Physical and Theoretical Chemistry
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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
UR - http://www.scopus.com/inward/record.url?scp=33748982653&partnerID=8YFLogxK
U2 - 10.1016/j.theochem.2006.06.010
DO - 10.1016/j.theochem.2006.06.010
M3 - Article
AN - SCOPUS:33748982653
VL - 775
SP - 1
EP - 7
JO - Computational and Theoretical Chemistry
JF - Computational and Theoretical Chemistry
SN - 2210-271X
IS - 1-3
ER -