Dimerization in the pyridone/hydroxypyridine tautomeric systems: relative stabilities of the dimers in the 2-pyridone/2-hydroxypyridine and in the 4-pyridone/4-hydroxypyridine systems

Zdeněk Slanina, Andrzej Leś, Ludwik Adamowicz

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Abstract

Three dimers created from the 2-pyridone/2-hydroxypyridine tautomers and four dimers created by the 4-pyridone/4-hydroxypyridine tautomers were described using ab initio self-consistent-field (SCF) calculation and the energies were corrected for the electron correlation contribution by using the second-order Møller-Plesset (MP2) perturbation treatment. Three and four energy minima were revealed on the dimeric potential hypersurfaces of 2-pyridone/2-hydroxypyridine and 4-pyridone/4-hydroxypyridine, respectively. The relative stabilities of the three- and four-membered systems were evaluated in terms of partition functions constructed from the calculated dimeric parameters. The MP2 energies suggest that, under the conditions of interdimeric equilibrium, there is a coexistence of the oxo-oxo and hydroxy-hydroxy dimers of the 2-pyridone/ 2-hydroxypyridine system. For the 4-pyridone/4-hydroxypyridine tautomeric system MP2 calculations predict a predominance of the hydroxy-hydroxy dimer.

Original languageEnglish (US)
Pages (from-to)491-498
Number of pages8
JournalJournal of Molecular Structure: THEOCHEM
Volume257
Issue number3-4
DOIs
StatePublished - May 25 1992

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Pyridones
Dimerization
dimerization
Dimers
dimers
tautomers
Electron correlations
self consistent fields
energy
partitions
perturbation
4-pyridone
4-hydroxypyridine
2-hydroxypyridine
hydroxypyridines
Electrons
electrons

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computational Theory and Mathematics
  • Atomic and Molecular Physics, and Optics

Cite this

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title = "Dimerization in the pyridone/hydroxypyridine tautomeric systems: relative stabilities of the dimers in the 2-pyridone/2-hydroxypyridine and in the 4-pyridone/4-hydroxypyridine systems",
abstract = "Three dimers created from the 2-pyridone/2-hydroxypyridine tautomers and four dimers created by the 4-pyridone/4-hydroxypyridine tautomers were described using ab initio self-consistent-field (SCF) calculation and the energies were corrected for the electron correlation contribution by using the second-order M{\o}ller-Plesset (MP2) perturbation treatment. Three and four energy minima were revealed on the dimeric potential hypersurfaces of 2-pyridone/2-hydroxypyridine and 4-pyridone/4-hydroxypyridine, respectively. The relative stabilities of the three- and four-membered systems were evaluated in terms of partition functions constructed from the calculated dimeric parameters. The MP2 energies suggest that, under the conditions of interdimeric equilibrium, there is a coexistence of the oxo-oxo and hydroxy-hydroxy dimers of the 2-pyridone/ 2-hydroxypyridine system. For the 4-pyridone/4-hydroxypyridine tautomeric system MP2 calculations predict a predominance of the hydroxy-hydroxy dimer.",
author = "Zdeněk Slanina and Andrzej Leś and Ludwik Adamowicz",
year = "1992",
month = "5",
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doi = "10.1016/0166-1280(92)85058-S",
language = "English (US)",
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T1 - Dimerization in the pyridone/hydroxypyridine tautomeric systems

T2 - relative stabilities of the dimers in the 2-pyridone/2-hydroxypyridine and in the 4-pyridone/4-hydroxypyridine systems

AU - Slanina, Zdeněk

AU - Leś, Andrzej

AU - Adamowicz, Ludwik

PY - 1992/5/25

Y1 - 1992/5/25

N2 - Three dimers created from the 2-pyridone/2-hydroxypyridine tautomers and four dimers created by the 4-pyridone/4-hydroxypyridine tautomers were described using ab initio self-consistent-field (SCF) calculation and the energies were corrected for the electron correlation contribution by using the second-order Møller-Plesset (MP2) perturbation treatment. Three and four energy minima were revealed on the dimeric potential hypersurfaces of 2-pyridone/2-hydroxypyridine and 4-pyridone/4-hydroxypyridine, respectively. The relative stabilities of the three- and four-membered systems were evaluated in terms of partition functions constructed from the calculated dimeric parameters. The MP2 energies suggest that, under the conditions of interdimeric equilibrium, there is a coexistence of the oxo-oxo and hydroxy-hydroxy dimers of the 2-pyridone/ 2-hydroxypyridine system. For the 4-pyridone/4-hydroxypyridine tautomeric system MP2 calculations predict a predominance of the hydroxy-hydroxy dimer.

AB - Three dimers created from the 2-pyridone/2-hydroxypyridine tautomers and four dimers created by the 4-pyridone/4-hydroxypyridine tautomers were described using ab initio self-consistent-field (SCF) calculation and the energies were corrected for the electron correlation contribution by using the second-order Møller-Plesset (MP2) perturbation treatment. Three and four energy minima were revealed on the dimeric potential hypersurfaces of 2-pyridone/2-hydroxypyridine and 4-pyridone/4-hydroxypyridine, respectively. The relative stabilities of the three- and four-membered systems were evaluated in terms of partition functions constructed from the calculated dimeric parameters. The MP2 energies suggest that, under the conditions of interdimeric equilibrium, there is a coexistence of the oxo-oxo and hydroxy-hydroxy dimers of the 2-pyridone/ 2-hydroxypyridine system. For the 4-pyridone/4-hydroxypyridine tautomeric system MP2 calculations predict a predominance of the hydroxy-hydroxy dimer.

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