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 journalArticlepeer-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 languageEnglish (US)
Pages (from-to)313-327
Number of pages15
JournalJournal of Molecular Structure: THEOCHEM
Volume277
Issue numberC
DOIs
StatePublished - Dec 10 1992

ASJC Scopus subject areas

  • Biochemistry
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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