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dc.creatorCvijetić, Ilija
dc.creatorVitorović-Todorović, Maja D.
dc.creatorJuranić, Ivan
dc.creatorDrakulić, Branko
dc.date.accessioned2019-04-25T09:39:37Z
dc.date.available2019-04-25T09:39:37Z
dc.date.issued2013
dc.identifier.issn0026-9247
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/2689
dc.description.abstractThe reactivity of fifteen (E)-4-aryl-4-oxo-2-butenoic (aroylacrylic) acid arylamides toward thiols was studied, measuring the rate constants of the addition of model thiol nucleophile, 2-mercaptoethanol. The influence of the variation of the substituents on the phenyl rings on the rate of reaction was quantified using the Hammett substituent constants and descriptors derived from ab initio or semiempirical calculations (atomic charges, HOMO, and LUMO). Statistically significant linear correlations between second-order rate constants and Hammett substituent constants, as well as energies of LUMO orbitals, were obtained. Substituents on both aroyl and arylamido moieties were shown to influence the reactivity of studied compounds toward thiols. The regioselectivity of reaction was confirmed by NMR spectroscopy. Exclusively beta-addition product with respect to the aroyl keto group was obtained. The determined enthalpy and entropy of activation were found to be in agreement with the proposed reaction mechanism, which includes a highly ordered transition state.en
dc.publisherSpringer Wien, Wien
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS//
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/261499/EU//
dc.rightsrestrictedAccess
dc.sourceMonatshefte Fur Chemie
dc.subjectThia-Michael additionen
dc.subjectAroylacrylic acid phenylamidesen
dc.subjectKineticsen
dc.subjectQuantum chemical calculationsen
dc.subjectNMR spectroscopyen
dc.titleReactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER studyen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractЈуранић, Иван О.; Виторовић-Тодоровић, Маја Д.; Цвијетић, Илија; Дракулић, Бранко;
dc.citation.volume144
dc.citation.issue12
dc.citation.spage1815
dc.citation.epage1824
dc.citation.other144(12): 1815-1824
dc.citation.rankM22
dc.identifier.doi10.1007/s00706-013-1084-6
dc.identifier.scopus2-s2.0-84961983959
dc.identifier.wos000327083100009
dc.type.versionpublishedVersionen


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