Photodimerizations of hydroxy- and benzoylated 4-azachalcones and quantum chemical investigation of the reactions

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dc.authorid6701651931
dc.authorid25423371900
dc.authorid8512207300
dc.authorid6701867097
dc.contributor.authorYaşar A.
dc.contributor.authorYaylI N.
dc.contributor.authorUsta A.
dc.contributor.authorYaylI N.
dc.date.accessioned20.04.201910:49:12
dc.date.accessioned2019-04-20T21:44:52Z
dc.date.available20.04.201910:49:12
dc.date.available2019-04-20T21:44:52Z
dc.date.issued2010
dc.departmentBayburt Üniversitesien_US
dc.description.abstractPhotodimerization reactions of compounds 4-6 gave four new cyclobutane-containing compounds (7-9) with full control over the stereochemistry at the four stereogenic centers. These new cyclobutane- containing compounds had ?-truxinic (7a), ?-truxinic (7b and 9), and ?-truxillic (8) structures. However, o-, m-, and p-hydroxy 4-azachalcones (1-3) did not give photochemical cyclization products under any conditions (in solvent or in their solid or molten states). Experimental data suggested the possibility of frontier orbital control over stereochemical behavior, so some theoretical calculations were performed. Full geometrical optimization of compounds 1-9 was performed via DFT B3LYP/6-31+G**, and their electronic structures were also investigated. The geometries of the singlet and triplet states were initially optimized by density functional theory (DFT) and the configuration interaction singles (CIS) B3LYP/3-21 +G**level. An additional calculation was performed for the triplet state using the ground-state geometry. The possible photochemical dimerization products of compounds 7-9 (a-g) and the intrinsic reaction coordinates (IRCs) of the reactions of compounds 4-6 were calculated theoretically by the DFT/3-21+G**method. The configurations (reactant, transition state, product, and reaction pathway) corresponding to the stationary points (minima or saddle points) were determined. The intrinsic reaction coordinates were followed to verify the energy profiles that connect each TS to the appropriate local minimum. The dimeric products expected from the calculations coincided with the dimers produced experimentally. © Springer-Verlag 2010.en_US
dc.identifier.doi10.1007/s00894-009-0642-7
dc.identifier.endpage1355
dc.identifier.issn1610-2940
dc.identifier.issue8
dc.identifier.pmid20140472en_US
dc.identifier.scopus2-s2.0-77955770527en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage1347
dc.identifier.urihttps://dx.doi.org/10.1007/s00894-009-0642-7
dc.identifier.urihttps://hdl.handle.net/20.500.12403/960
dc.identifier.volume16
dc.identifier.wosWOS:000280345500005en_US
dc.identifier.wosqualityQ1en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.relation.ispartofJournal of Molecular Modelingen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAzachalcones
dc.subjectIRC
dc.subjectPhotodimerization reactions
dc.subjectTheoretical calculations
dc.subject2 hydroxy 4 azachalcone
dc.subject3 hydroxy 4 azachalcone
dc.subject4 hydroxy 4 azachalcone
dc.subjectbeta truxinic
dc.subjectchalcone derivative
dc.subjectepsilon truxinic
dc.subjectgamma truxinic
dc.subjectunclassified drug
dc.subjectarticle
dc.subjectchemical reaction
dc.subjectcontrolled study
dc.subjectcyclization
dc.subjectdensity functional theory
dc.subjectdimerization
dc.subjectgeometry
dc.subjectphase transition
dc.subjectphotochemistry
dc.subjectphotodimerization
dc.subjectpriority journal
dc.subjectquantum chemistry
dc.subjectstereochemistry
dc.subjecttheoretical model
dc.subjectBenzene
dc.subjectChalcone
dc.subjectDimerization
dc.subjectElectrons
dc.subjectHydroxylation
dc.subjectLight
dc.subjectModels, Chemical
dc.subjectModels, Molecular
dc.subjectQuantum Theory
dc.subjectThermodynamics
dc.subjectAzachalcones
dc.subjectIRC
dc.subjectPhotodimerization reactions
dc.subjectTheoretical calculations
dc.subject2 hydroxy 4 azachalcone
dc.subject3 hydroxy 4 azachalcone
dc.subject4 hydroxy 4 azachalcone
dc.subjectbeta truxinic
dc.subjectchalcone derivative
dc.subjectepsilon truxinic
dc.subjectgamma truxinic
dc.subjectunclassified drug
dc.subjectarticle
dc.subjectchemical reaction
dc.subjectcontrolled study
dc.subjectcyclization
dc.subjectdensity functional theory
dc.subjectdimerization
dc.subjectgeometry
dc.subjectphase transition
dc.subjectphotochemistry
dc.subjectphotodimerization
dc.subjectpriority journal
dc.subjectquantum chemistry
dc.subjectstereochemistry
dc.subjecttheoretical model
dc.subjectBenzene
dc.subjectChalcone
dc.subjectDimerization
dc.subjectElectrons
dc.subjectHydroxylation
dc.subjectLight
dc.subjectModels, Chemical
dc.subjectModels, Molecular
dc.subjectQuantum Theory
dc.subjectThermodynamics
dc.titlePhotodimerizations of hydroxy- and benzoylated 4-azachalcones and quantum chemical investigation of the reactionsen_US
dc.typeArticleen_US

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