Show simple item record

dc.creatorRančić, Milica
dc.creatorTrišović, Nemanja
dc.creatorMilčić, Miloš
dc.creatorJovanović, Maja
dc.creatorJovanović, Bratislav Ž.
dc.creatorMarinković, Aleksandar
dc.date.accessioned2021-03-10T12:28:34Z
dc.date.available2021-03-10T12:28:34Z
dc.date.issued2014
dc.identifier.issn0022-152X
dc.identifier.urihttp://TechnoRep.tmf.bg.ac.rs/handle/123456789/2732
dc.description.abstractTwo series of 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines have been synthesized using different methods of conventional and microwave-assisted synthesis, and linear free-energy relationships have been applied to the C-13 NMR chemical shifts of the carbon atoms of interest. The substituent-induced chemical shifts have been analyzed using single substituent parameter and dual substituent parameter methods. The presented correlations describe satisfactorily the field and resonance substituent effects having similar contributions for C1 and the azomethine carbon, with exception of the carbon atom in para position to the substituent X. In both series, negative values have been found for C1 atom (reverse substituent effect). Quantum chemical calculations of the optimized geometries at MP2/6-31G++(d,p) level, together with C-13 NMR chemical shifts, give a better insight into the influence of the molecular conformation on the transmission of electronic substituent effects. The comparison of correlation results for different series of imines with phenyl, 4-nitrophenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl group attached at the azomethine carbon with the results for 4-substituted N-[1-(pyridine-3- and -4-yl)ethylidene]anilines for the same substituent set (X) indicates that a combination of the influences of electronic effects of the substituent X and the (1)-unit can be described as a sensitive balance of different resonance structures.en
dc.publisherWiley-Blackwell, Hoboken
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172013/RS//
dc.rightsrestrictedAccess
dc.sourceJournal of Heterocyclic Chemistry
dc.titleLinear Free-Energy Relationships Applied to the C-13 NMR Chemical Shifts in 4-Substituted N-[1-(Pyridine-3-and-4-yl)ethylidene]anilinesen
dc.typearticle
dc.rights.licenseARR
dc.citation.epage1451
dc.citation.issue5
dc.citation.other51(5): 1442-1451
dc.citation.rankM23
dc.citation.spage1442
dc.citation.volume51
dc.identifier.doi10.1002/jhet.1752
dc.identifier.rcubconv_4551
dc.identifier.scopus2-s2.0-85028227018
dc.identifier.wos000342746900035
dc.type.versionpublishedVersion


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record