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Spectroscopic Study of the Basicity of 4,6-Dihydroxypyrimidine Derivatives.

ABSTRACT: The protonation of a number of 4,6-dihydroxypyrimidine derivatives is studied, and the features of the electronic spectra of free bases and protonated forms are considered. It is shown that the alkyl substituents in position 2 increase the basicity of the compound, and the nitro group in position 5 leads to its decrease. In an acid medium (0.1-99.5% H₂SO₄), 4,6-dihydroxypyrimidine, 6-hydroxy-2-methylpyrimidine-4(3H)-one, and 6-hydroxy-2-ethylpyrimidine-4(3H)-one have two protonation stages, barbituric acid is protonated in three stages, and 6-hydroxy-2-methyl-5-nitropyrimidine-4(3H)-one and 6-hydroxy-2-ethyl-5-nitropyrimidine-4(3H)-one form a monocation.

SUBMITTER: Vu TQ

PROVIDER: S-EPMC8190809 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Spectroscopic Study of the Basicity of 4,6-Dihydroxypyrimidine Derivatives.

Vu Tuan Q TQ Yudin Nikolai V NV Kushtaev Alexander A AA Nguyen Thanh X TX Maltsev Sergey A SA

ACS omega 20210524 22

The protonation of a number of 4,6-dihydroxypyrimidine derivatives is studied, and the features of the electronic spectra of free bases and protonated forms are considered. It is shown that the alkyl substituents in position 2 increase the basicity of the compound, and the nitro group in position 5 leads to its decrease. In an acid medium (0.1-99.5% H<sub>2</sub>SO<sub>4</sub>), 4,6-dihydroxypyrimidine, 6-hydroxy-2-methylpyrimidine-4(3H)-one, and 6-hydroxy-2-ethylpyrimidine-4(3H)-one have two pr ...[more]

PMID: 34124438

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