Theoretical interpretation of the gas phase equilibrium of 2-hydroxypyridine/2(1H)-pyridinone

Andrzej Leś; Ludwik Adamowicz; Maciej J. Nowak; Leszek Lapinski

doi:10.1016/0166-1280(92)87149-T

Theoretical interpretation of the gas phase equilibrium of 2-hydroxypyridine/2(1H)-pyridinone

Andrzej Leś, Ludwik Adamowicz, Maciej J. Nowak, Leszek Lapinski

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Theoretical ab initio calculations are performed to provide support for our hypothesis that the gas phase ratio of the 2-hydroxypyridine/2(1H)-pyridinone tautomers results from the thermodynamic equilibrium which exists between cyclic hydrogen-bonded oxo-oxo and hydroxy-hydroxy dimers. We therefore, disprove the monomolecular mechanism of the tautomerization process, which has frequently been assumed in the past to estimate the free energy difference between the monomeric tautomers based on the experimentally determined tautomer ratio.

Original language	English (US)
Pages (from-to)	313-327
Number of pages	15
Journal	Journal of Molecular Structure: THEOCHEM
Volume	277
Issue number	C
DOIs	https://doi.org/10.1016/0166-1280(92)87149-T
State	Published - Dec 10 1992

ASJC Scopus subject areas

Biochemistry
Condensed Matter Physics
Physical and Theoretical Chemistry

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title = "Theoretical interpretation of the gas phase equilibrium of 2-hydroxypyridine/2(1H)-pyridinone",

abstract = "Theoretical ab initio calculations are performed to provide support for our hypothesis that the gas phase ratio of the 2-hydroxypyridine/2(1H)-pyridinone tautomers results from the thermodynamic equilibrium which exists between cyclic hydrogen-bonded oxo-oxo and hydroxy-hydroxy dimers. We therefore, disprove the monomolecular mechanism of the tautomerization process, which has frequently been assumed in the past to estimate the free energy difference between the monomeric tautomers based on the experimentally determined tautomer ratio.",

author = "Andrzej Le{\'s} and Ludwik Adamowicz and Nowak, {Maciej J.} and Leszek Lapinski",

note = "Funding Information: This study was supported by the National Science Foundation under Grant No. INT-9100935.",

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T1 - Theoretical interpretation of the gas phase equilibrium of 2-hydroxypyridine/2(1H)-pyridinone

AU - Leś, Andrzej

AU - Adamowicz, Ludwik

AU - Nowak, Maciej J.

AU - Lapinski, Leszek

N1 - Funding Information: This study was supported by the National Science Foundation under Grant No. INT-9100935.

PY - 1992/12/10

Y1 - 1992/12/10

N2 - Theoretical ab initio calculations are performed to provide support for our hypothesis that the gas phase ratio of the 2-hydroxypyridine/2(1H)-pyridinone tautomers results from the thermodynamic equilibrium which exists between cyclic hydrogen-bonded oxo-oxo and hydroxy-hydroxy dimers. We therefore, disprove the monomolecular mechanism of the tautomerization process, which has frequently been assumed in the past to estimate the free energy difference between the monomeric tautomers based on the experimentally determined tautomer ratio.

AB - Theoretical ab initio calculations are performed to provide support for our hypothesis that the gas phase ratio of the 2-hydroxypyridine/2(1H)-pyridinone tautomers results from the thermodynamic equilibrium which exists between cyclic hydrogen-bonded oxo-oxo and hydroxy-hydroxy dimers. We therefore, disprove the monomolecular mechanism of the tautomerization process, which has frequently been assumed in the past to estimate the free energy difference between the monomeric tautomers based on the experimentally determined tautomer ratio.

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Theoretical interpretation of the gas phase equilibrium of 2-hydroxypyridine/2(1H)-pyridinone

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