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dc.creatorMilošević, Milena D.
dc.creatorPrlainović, Nevena Z.
dc.creatorMilčić, Miloš K.
dc.creatorNikolić, Vesna
dc.creatorBožić, Aleksandra R.
dc.creatorBigović, Miljan
dc.creatorMarinković, Aleksandar
dc.date.accessioned2018-11-22T00:45:17Z
dc.date.available2018-11-22T00:45:17Z
dc.date.issued2018
dc.identifier.issn1735-207X
dc.identifier.urihttp://cherry.chem.bg.ac.rs/handle/123456789/2216
dc.description.abstract15 symmetric 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides were synthesized in this work. Their structures were characterized using IR, H-1 and C-13 NMR, and UV-Vis spectroscopy. DFT calculations indicated that s-trans/s-trans conformation prevail in all compounds. The effects of specific and non-specific solvent-solute interactions on the UV-Vis absorption maxima shifts were evaluated using linear solvation-free energy relationships (LSER), i.e., Kamlet-Taft and Catalan models. A linear free energy relationship (LFER) in the form of single substituent parameter equations (SSP) was used to postulate quantitative structure-property relations of substituent effect on NMR data. TD-DFT results showed dependence of electronic transition on the substituent effects. The push-pull character of these compounds was analyzed by differences in C-13 chemical shift of the ethylenic double bond in 2- and 6-positions of cross-conjugated with pyridinum central ring. Also, the quotient of the occupations for the bonding pi and anti-bonding pi* orbitals of this bond was considered. Good correlations of the selected parameter between double bond lengths with pi*/pi and C-13 chemical shift differences of the bridging group proved them to be adequate descriptor of push-pull character. Synthesized compounds were screened for the antioxidant activity, using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical methods, and results demonstrated moderate antioxidant potential.en
dc.publisherSpringer, New York
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS//
dc.rightsrestrictedAccess
dc.sourceJournal of the Iranian Chemical Society
dc.subjectSolvatochromismen
dc.subjectKamlet-Taften
dc.subjectCatalanen
dc.subjectAntioxidant activityen
dc.titleSolvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodidesen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractМилосевиц, Милена Д.; Прлаиновиц, Невена З.; Бозиц, Aлександра; Милчић, Милош; Николиц, Весна; Биговиц, Миљан; Маринковиц, Aлександар Д.;
dc.citation.volume15
dc.citation.issue11
dc.citation.spage2483
dc.citation.epage2501
dc.identifier.wos000444188800007
dc.identifier.doi10.1007/s13738-018-1437-5
dc.citation.other15(11): 2483-2501
dc.citation.rankM23
dc.description.otherSupplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3255]
dc.type.versionpublishedVersionen
dc.identifier.scopus2-s2.0-85052993656
dc.identifier.rcubKon_3547


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