Show simple item record

dc.creatorCvijetic, Ilija N.
dc.creatorVerbic, Tatjana Z.
dc.creatorDrakulić, Branko J.
dc.creatorStanković, Dalibor M.
dc.creatorJuranic, Ivan O.
dc.creatorManojlović, Dragan D.
dc.creatorZloh, Mire
dc.date.accessioned2018-03-01T17:37:12Z
dc.date.available2018-03-01T17:37:12Z
dc.date.issued2017
dc.identifier.issn0352-5139 (print)
dc.identifier.urihttp://vinar.vin.bg.ac.rs/handle/123456789/1570
dc.description.abstractRedox 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.en
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS//
dc.relationMagbiovin project (FP7-ERAChairs-PilotCall) [621375]
dc.rightsopenAccessen
dc.sourceJournal of the Serbian Chemical Societyen
dc.subjectaryldiketo acids (ADKs)en
dc.subjectredox propertiesen
dc.subjectstructure-property relationshipen
dc.subjectacidity constantsen
dc.titleRedox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acidsen
dc.typearticleen
dcterms.abstractМанојловиц, Драган Д.; Станковић Далибор; Вербиц, Татјана З.; Злох, Мире; Цвијетиц, Илија Н.; Дракулиц, Бранко Ј.; Јураниц, Иван О.;
dc.citation.volume82
dc.citation.issue3
dc.citation.spage303
dc.citation.epage316
dc.identifier.wos000401126100006
dc.identifier.doi10.2298/JSC161118021C
dc.identifier.scopus2-s2.0-85018278992
dc.identifier.fulltexthttp://vinar.vin.bg.ac.rs//bitstream/id/11933/1566.pdf


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record