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

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...

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Bibliographic Details
Published in:Russian Journal of Physical Chemistry A 2023-10, Vol.97 (10), p.2275-2281
Main Authors: Khamitov, E. M., Petrova, S. F., Il’ina, M. G., Nugumanov, T. R., Lobov, A. N., Ivanov, S. P.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemoinformatics and Computer Modeling
Diketones
Enantiomers
Equilibrium methods
Physical Chemistry
Quantum chemistry
Thermodynamic equilibrium
Thermodynamics
Vapor phases
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Summary: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(1 Н ,3 Н )-dione are S e and R e 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.
ISSN:0036-0244
1531-863X
DOI:10.1134/S003602442310014X