The theoretical investigation on the properties of fluorine-substituted uracil

Publication date: Available online 5 April 2019Source: Computational and Theoretical ChemistryAuthor(s): Min Zhang, Jinfang Xu, Xinming WangAbstractAn investigation was conducted of Fluorine-substituted uracils (5-fluorouracil, 6-fluorouracil and 5, 6-difluoro-uracil) at the B3LYP [6-311G(d, p) / 6-311+G(d, p) / 6-311++G(d, p)] levels. A calculation was performed of their equilibrium structures and harmonic frequencies in gas and water. A combination of C-F binding energies, Natural bond orbital (NBO), reactivity descriptors, Fukui functions, and aromaticity was applied to figure out the impact made by the numbers and location of fluorine atoms on the structural parameters, infrared spectrum, active site and aromaticity of the uracil. In this paper, a systematic research is carried out into the similarities and differences between fluorine-substituted at 5-position of uracil and 6-position. The outcomes are expected to provide a theoretical guidance with regard to the development of the fluoridated drugs.Graphical abstractThe aromaticity of fluorine-substituted uracil is larger than uracil, because the 2pzelectrons of F atoms participated in the formation the π bond of the uracil ring. The E2 value associated with C-F bond indicate that 5-FU is more active than 6-FU.

Source: Computational and Theoretical Chemistry - April 5, 2019 Category: Chemistry Source Type: research