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

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...

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Bibliographic Details
Published in:ACS omega Vol. 6; no. 22; pp. 14154 - 14163
Main Authors: Vu, Tuan Q, Yudin, Nikolai V, Kushtaev, Alexander A, Nguyen, Thanh X, Maltsev, Sergey A
Format: Journal Article
Language:English
Published: American Chemical Society 08-06-2021
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Summary: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.
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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.1c00671