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Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides
dc.creator | Milošević, Milena D. | |
dc.creator | Prlainović, Nevena | |
dc.creator | Milčić, Miloš | |
dc.creator | Nikolić, Vesna | |
dc.creator | Božić, Aleksandra R. | |
dc.creator | Bigović, Miljan | |
dc.creator | Marinković, Aleksandar | |
dc.date.accessioned | 2021-03-10T13:40:45Z | |
dc.date.available | 2021-03-10T13:40:45Z | |
dc.date.issued | 2018 | |
dc.identifier.issn | 1735-207X | |
dc.identifier.uri | http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3843 | |
dc.description.abstract | 15 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.publisher | Springer, New York | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS// | |
dc.rights | restrictedAccess | |
dc.source | Journal of the Iranian Chemical Society | |
dc.subject | Solvatochromism | en |
dc.subject | Kamlet-Taft | en |
dc.subject | Catalan | en |
dc.subject | Antioxidant activity | en |
dc.title | Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides | en |
dc.type | article | |
dc.rights.license | ARR | |
dc.citation.epage | 2501 | |
dc.citation.issue | 11 | |
dc.citation.other | 15(11): 2483-2501 | |
dc.citation.rank | M23 | |
dc.citation.spage | 2483 | |
dc.citation.volume | 15 | |
dc.identifier.doi | 10.1007/s13738-018-1437-5 | |
dc.identifier.scopus | 2-s2.0-85052993656 | |
dc.identifier.wos | 000444188800007 | |
dc.type.version | publishedVersion |