Show simple item record

dc.creatorCvijetić, Ilija
dc.creatorVitorović-Todorović, Maja D.
dc.creatorJuranić, Ivan O.
dc.creatorNakarada, Dura J.
dc.creatorMilosavljević, Milica D.
dc.creatorDrakulić, Branko J.
dc.date.accessioned2018-11-22T00:28:36Z
dc.date.available2018-11-22T00:28:36Z
dc.date.issued2014
dc.identifier.issn0026-9247
dc.identifier.urihttp://cherry.chem.bg.ac.rs/handle/123456789/1816
dc.description.abstractRates of the aza-Michael addition of piperidine and benzylamine to thirteen (E)-4-aryl-4-oxo-2-butenoic acid phenylamides (AACPs) are reported. Progress of the reaction was monitored by UV/Vis spectroscopy. The 2D NMR spectra confirmed regioselectivity of the reactions. Piperidine and benzylamine provide exclusively beta-adducts in respect to the aroyl keto group. Influence of the substituents of the aroyl phenyl ring of AACPs on the rate of the reaction was quantified by Hammett substituent constants, partial atomic charges, and the energies of frontier orbitals. Good correlations between second-order rate constants and the Hammett substituent constants were obtained (r = 0.98, piperidine; r = 0.94, benzylamine) for para-, and meta-, para-substituted derivatives. Best correlations were obtained with the energies of the lowest unoccupied molecular orbitals of compounds, derived from the MP2 level of theory. Calculated UV/Vis spectra of representative AACPs and their Michael adduct with piperidine and benzylamine are in fair agreement with experimentally obtained data.en
dc.publisherSpringer Wien, Wien
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/171017/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172035/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/43007/RS//
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/261499/EU//
dc.rightsrestrictedAccess
dc.sourceMonatshefte Fur Chemie
dc.subjectMichael additionen
dc.subjectUV/Vis spectroscopyen
dc.subjectKineticsen
dc.subjectLinear free-energy relationshipsen
dc.subjectZINDO/S calculationsen
dc.titleReactivity of (E)-4-aryl-4-oxo-2-butenoic acid phenylamides with piperidine and benzylamine: kinetic and theoretical studyen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractМилосављевиц, Милица Д.; Дракулиц, Бранко Ј.; Накарада, Дура Ј.; Цвијетић, Илија; Виторовиц-Тодоровиц, Маја Д.; Јураниц, Иван О.;
dc.citation.volume145
dc.citation.issue8
dc.citation.spage1297
dc.citation.epage1306
dc.identifier.wos000339378800010
dc.identifier.doi10.1007/s00706-014-1223-8
dc.citation.other145(8): 1297-1306
dc.citation.rankM22
dc.type.versionpublishedVersionen
dc.identifier.scopus2-s2.0-84904268026
dc.identifier.rcubKon_2699


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record