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

E. M. Khamitov; Хамитов Э. М.; S. F. Petrova; Петрова С. Ф.; M. G. Il’ina; Ильина М. Г.; T. R. Nugumanov; Нугуманов Т. Р.; A. N. Lobov; Лобов А. Н.; S. P. Ivanov; Иванов С. П.

doi:10.31857/S004445372310014X

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

Authors: Khamitov E.M.¹, Petrova S.F.¹, Il’ina M.G.¹, Nugumanov T.R.¹, Lobov A.N.¹, Ivanov S.P.¹
Affiliations:
1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences
Issue: Vol 97, No 10 (2023)
Pages: 1481-1487
Section: ХЕМОИНФОРМАТИКА И КОМПЬЮТЕРНОЕ МОДЕЛИРОВАНИЕ
Submitted: 26.02.2025
Published: 01.10.2023
URL: https://innoscience.ru/0044-4537/article/view/668652
DOI: https://doi.org/10.31857/S004445372310014X
EDN: https://elibrary.ru/XYQRJC
ID: 668652

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Abstract
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Abstract

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.

Keywords

5,5,6-trihydroxy-6-methyldihydropyrimidine-2,4(1Н,3Н)-dione, enantiomers, conformation, NMR spectroscopy, thermodynamic stability, nonspecific solvation

References

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