Theoretical Study of 5,5,6-Trihydroxy-6-methyldihydropyrimidine-2,4-dione Enantiomers

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Resumo

The thermodynamic stability of the axial (а) and equatorial (е) forms of the S- and R-enantiomers of 5,5,6-trihydroxy-6-methyldihydropyrimidine-2,4(1Н,3Н)-dione was studied by quantum-chemical methods. The equilibrium geometrical parameters and thermodynamic characteristics were determined by the DFT method using the TPSS functional combined with the 6-311+G(d,p) split-valence basis set including the d and p type polarization functions. The Chemcraft and VMD programs were used to visualize the geometrical structure. The most stable forms of 5,5,6-trihydroxy-6-methyldihydropyrimidine-2,4(1Н,3Н)-dione are Se and Re in both the gas phase and aqueous and organic (DMSO) media. The activation barrier of the rearrangement inside the ring is 21.22–24.93 kJ/mol depending on the medium.

Sobre autores

E. Khamitov

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Email: petrova_sf89@anrb.ru
450054, Ufa, Bashkortostan, Russia

S. Petrova

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Email: petrova_sf89@anrb.ru
450054, Ufa, Bashkortostan, Russia

M. Il’ina

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Email: petrova_sf89@anrb.ru
450054, Ufa, Bashkortostan, Russia

T. Nugumanov

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Email: petrova_sf89@anrb.ru
450054, Ufa, Bashkortostan, Russia

A. Lobov

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Email: petrova_sf89@anrb.ru
450054, Ufa, Bashkortostan, Russia

S. Ivanov

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences

Autor responsável pela correspondência
Email: petrova_sf89@anrb.ru
450054, Ufa, Bashkortostan, Russia

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Declaração de direitos autorais © Э.М. Хамитов, С.Ф. Петрова, М.Г. Ильина, Т.Р. Нугуманов, А.Н. Лобов, С.П. Иванов, 2023