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Posyagin, G. S.; Posyagina, E. Yu.; Zalesov, V. V.; Kataev, S. S.

doi:10.1023/a:1013950903524

Cited by 2 publications

(1 citation statement)

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“…There are many electrochemical studies of various 1,3-diketones and their metal complexes in the literature. [19][20][21][22] Nevertheless, except data on the polaro-graphic behavior of four aryldiketo acid methyl-esters (unsubstituted, 4-Me-Ph, 4-Cl-Ph and 2-HO-Ph) in the pH range 2-12 in aqueous 20 % 2-propanol, 23 to the best of our knowledge there are no similar reports for ADKs. Oxidation and reduction potentials of the compounds at pH 1, 5 and 10, as well as the pK a values of the carboxyl group and the hydroxy group in the α-position with respect to carboxyl group were experimentally obtained.…”

Section: Introductionmentioning

confidence: 95%

Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids

Cvijetić¹,

Verbić

Drakulić

et al. 2017

JSCS

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Redox properties of a set of aryldiketo acids (ADKs), small organic molecules that comprise 2,4-dioxobutanoic acid moiety, were studied. Along with well-known HIV-1 integrase (IN) inhibition, ADKs exert widespread biological activities. The aim of this work was to evaluate the effects of aryl substitutions on the properties of the dioxobutanoic moiety that is involved in key interactions with metal ions within the active sites of target enzymes. The effect of pH on the electronic properties of nine congeners was examined using cyclic voltammetry and differential pulse polarography. The compounds were chosen as a simple set of congeners bearing Me-groups on the phenyl ring, which should not be involved in electrochemical reactions, leaving the diketo moiety as the sole electrophore. The substitution pattern was systematically varied, yielding a set having different torsion between the phenyl ring and the aryl keto group (Ar-C(O)). The protonation state of the ADKs at different pH values was determined from the experimentally obtained pK a values. The results showed that an equal number of protons and electrons were involved in the oxidation and reduction reactions at the surface of the electrode. Quantitative linear correlations were found between the reduction potentials and the energies of the frontier orbitals, calculated for neutral, mono-anionic and the corresponding radical anionic species, and the steric parameter as two independent variables.

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