Quantum Chemical Studies of the Substituent Effect on the Reaction of Carbonyl Oxime with Amine

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dc.authorid0000-0001-7228-2340en_US
dc.contributor.authorKaya, Yunus
dc.date.accessioned2021-03-20T20:14:32Z
dc.date.available2021-03-20T20:14:32Z
dc.date.issued2016
dc.departmentBTÜ, Mühendislik ve Doğa Bilimleri Fakültesi, Kimya Bölümüen_US
dc.description.abstractThe reaction of the two different substitue carbonyl oximes (isonitrosoacetylnaphthaline, inanH and nitro-isonitrosoacetophenone, ninapH) with two different amines (1-phenylethanol amine, pea, and ethanol amine, ea) was carried out and characterized by elemental analyses, IR, and H-1 and C-13 NMR spectroscopic methods. As a result of these experimental studies, two different levels for all reactions were determined: (I) formation of imine oxime and (II) rearrangement of imine oxime or formation of amido alcohol. After a mechanism was suggested for all of these reactions, the reaction mechanism of carbonyl oxime with amine was first studied by means of the B3LYP/6-311G(d,p) method. Because of the deficiency of density functional theory (DFT) on dispersion effects, the wB97X-D/6-311G(d,p) method, which includes dispersion correction, was used to obtain the reaction heat and free energy barriers to explain why the formation (imine oxime) and unexpected rearrangement products (amido alcohol) occurred or did not occur. The statistical thermodynamic method was used to obtain the changes in thermodynamic properties of the studied molecules between 100 and 500 K. From a kinetic viewpoint, the slowest step of the reactions is the IN1-TS2-IN2 step, which determines the steps of the reaction kinetics. In addition, spectroscopic properties such as vibrational and NMR chemical shifts were studied for all of the molecules. The frontier molecular orbitals (FMOs), highest occupied molecular orbitals (HOMOs), and lowest unoccupied molecular orbitals (LUMOs) were monitored for all of the molecules.en_US
dc.description.sponsorshipUludag UniversityUludag University; [KUAP(F)-2015/20]en_US
dc.description.sponsorshipThis work is a part of a research project KUAP(F)-2015/20. The author thanks Uludag University for the financial support given to the projects.en_US
dc.identifier.doi10.1021/acs.jpca.6b05147en_US
dc.identifier.endpage5744en_US
dc.identifier.issn1089-5639
dc.identifier.issn1520-5215
dc.identifier.issue28en_US
dc.identifier.pmid27362286en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage5736en_US
dc.identifier.urihttp://doi.org/10.1021/acs.jpca.6b05147
dc.identifier.urihttps://hdl.handle.net/20.500.12885/1067
dc.identifier.volume120en_US
dc.identifier.wosWOS:000380590800034en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.institutionauthorKaya, Yunus
dc.language.isoenen_US
dc.publisherAmer Chemical Socen_US
dc.relation.ispartofJournal Of Physical Chemistry Aen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject[No Keywords]en_US
dc.titleQuantum Chemical Studies of the Substituent Effect on the Reaction of Carbonyl Oxime with Amineen_US
dc.typeArticleen_US

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