Oxo-hydroxy tautomerism of uracil and 5-fluorouracil

Andrzej Leś, Ludwik Adamowicz

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51 Citations (Scopus)

Abstract

The three lowest energy tautomeric forms of uracil and 5-fluorouracil have been studied by using the second-order many-body perturbation theory (MBPT(2)) with Gaussian DZP basis sets. The zero-point nuclear energy has been estimated by means of the harmonic approximation using analytical derivatives of the SCF 3-21G energy. The uracil and 5-fluorouracil molecules have been predicted to exist in the gas phase in the dioxo forms in agreement with the majority of experimental data. The 2-hydroxy-4-oxo and 2-oxo-4-hydroxy tautomeric forms of uracil have been found to be less stable than the main dioxo form by 44 and 50 kJ mol-1, respectively. The corresponding values for 5-fluorouracil are 29 and 52 kJ mol-1. The relevance of the present results to recent IR and fluorescence spectroscopical experimental works is discussed. Some aspects of the point mutation theory in view of the present work are also considered.

Original languageEnglish (US)
Pages (from-to)7078-7081
Number of pages4
JournalJournal of Physical Chemistry
Volume93
Issue number20
StatePublished - 1989

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uracil
Uracil
Fluorouracil
Nuclear energy
Fluorescence
Derivatives
Molecules
Gases
mutations
nuclear energy
self consistent fields
perturbation theory
vapor phases
harmonics
fluorescence
energy
approximation
molecules

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Oxo-hydroxy tautomerism of uracil and 5-fluorouracil. / Leś, Andrzej; Adamowicz, Ludwik.

In: Journal of Physical Chemistry, Vol. 93, No. 20, 1989, p. 7078-7081.

Research output: Contribution to journalArticle

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