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Korelacije strukture i reaktivnosti za kinetiku reakcije sinteze supstituisanih 4-fenil-1,4-dihidropiridina

dc.creatorUrošević, Jovica V.
dc.creatorDrmanić, Saša
dc.creatorNikolić, Jasmina
dc.creatorJuranić, Ivan
dc.creatorJovanović, Bratislav Ž.
dc.date.accessioned2021-03-10T12:04:09Z
dc.date.available2021-03-10T12:04:09Z
dc.date.issued2013
dc.identifier.issn0352-5139
dc.identifier.urihttp://TechnoRep.tmf.bg.ac.rs/handle/123456789/2347
dc.description.abstractQuantitative structure-reactivity correlations for the kinetics of the Hantzsch synthesis of 4-(substituted phenyl)-1,4-dihydropyridines in the reaction between ethyl m- and p-substituted 2-benzylideneacetoacetate and the enamine (ethyl 3-aminocrotonate) was studied. The reaction kinetics was followed spectrophotometrically. It was found that the reaction correspond to second-order kinetics. Quantitative structure-reactivity correlations of log k were obtained with the corresponding substituent constants (s, s+, sI and s + ) using the Hammett and extended Hammett equation (dual substituent parameter, DSP, equation). They showed linear relationships with positive values of reaction constants (r). The obtained data were processed by linear regression analysis. It was confirmed that Michael addition of the enamine to benzylidene represented the slow step of the reaction with a high positive charge at the benzylidene molecule. MO calculations were performed and they were in agreement with the conclusions derived from the structure-reactivity correlations. .en
dc.description.abstractProučavan je kvantitativan odnos strukture i reaktivnosti za kinetiku Hančove sinteze supstituisanih 4-fenil-1,4-dihidropiridina u reakciji etil-m- i p-supstituisanih 2-benziliden-acetoacetata i enamina. Kinetika ispitivane reakcije je praćena spektrofotometrijskim metodom. Zapaženo je da je reč o reakciji drugog reda. Kvantitativne korelacije strukture i reaktivnosti koje izražavaju logaritam određene konstante brzine reakcije (log k) u zavisnosti od odgovarajućih konstanti supstituenata (s, s+,sI i s +) određene su za Hametovu (Hammett) i proširenu Hametovu jednačinu (DSP-jednačinu). Pokazale su linearnu zavisnost sa pozitivnim vrednostima nagiba, odnosno reakcione konstante (r). Time je potvrđeno da Majklova (Michael) adicija enamina na benziliden predstavlja spori stupanj u reakciji sa izraženim pozitivnim naelektrisanjem na molekulu benzilidena. MO proračuni su takođe urađeni i njihovi rezultati su bili u skladu sa zaključcima izvedenim iz korelacija strukture i reaktivnosti. .sr
dc.publisherSerbian Chemical Society, Belgrade
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS//
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.sourceJournal of the Serbian Chemical Society
dc.subject1,4-dihydropyridinesen
dc.subjectHantzsch synthesisen
dc.subjectMichael additionen
dc.subjectHammet equationen
dc.subjectextended Hammett equationen
dc.subjectMO calculationsen
dc.titleStructure-reactivity correlation for the kinetics of the formation reaction of 4-(substituted phenyl)-1,4-dihydropyridinesen
dc.titleKorelacije strukture i reaktivnosti za kinetiku reakcije sinteze supstituisanih 4-fenil-1,4-dihidropiridinasr
dc.typearticle
dc.rights.licenseBY-NC-ND
dc.citation.epage1973
dc.citation.issue12
dc.citation.other78(12): 1963-1973
dc.citation.rankM23
dc.citation.spage1963
dc.citation.volume78
dc.identifier.fulltexthttp://TechnoRep.tmf.bg.ac.rs/bitstream/id/12022/0352-51391300139U.pdf
dc.identifier.rcubconv_745
dc.identifier.scopus2-s2.0-84890817282
dc.identifier.wos000329261200010
dc.type.versionpublishedVersion


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