DEPENDENCE OF TAUTOMERISM ON SUBSTITUENT TYPE IN o-HYDROXY SCHIFF BASES

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dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.authoridKastas, Gokhan/0000-0002-5956-405X
dc.contributor.authorKastas, Cigdem Albayrak
dc.contributor.authorKastas, Gokhan
dc.date.accessioned2025-03-23T19:27:30Z
dc.date.available2025-03-23T19:27:30Z
dc.date.issued2019
dc.departmentSinop Üniversitesi
dc.description.abstractQuantum computational methods were used to elucidate the structures of the o-hydroxy Schiff bases with different substituents. It is possible for a Schiff base to have different tautomeric structures depending on intramolecular proton transfer from the phenolic oxygen atom to the nitrogen atom. Proton transfer results in two tautomeric structures known as the phenol-imine and keto-amine forms. To explain the substituent effect on the proton transfer process in five o-hydroxy-Schiff bases, possible geometric structures in gas phase were optimized using density functional theory (DFT) at the B3LYP/6-311G(d,p) level. To describe tautomerism including intramolecular proton transfer, potential energy surface (PES) scans were performed starting from the optimized geometry of the phenol-imine form. HOMA indices were calculated in order to estimate pi-electron delocalization. In addition, the substituent effect on the tautomerization rate was examined using Hammett substituent constants and calculating the activation energies.
dc.identifier.doi10.20450/mjcce.2019.1531
dc.identifier.endpage94
dc.identifier.issn1857-5552
dc.identifier.issn1857-5625
dc.identifier.issue1
dc.identifier.scopus2-s2.0-85070503549
dc.identifier.scopusqualityQ3
dc.identifier.startpage85
dc.identifier.urihttps://doi.org/10.20450/mjcce.2019.1531
dc.identifier.urihttps://hdl.handle.net/11486/4915
dc.identifier.volume38
dc.identifier.wosWOS:000477950400010
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSoc Chemists Technologists Madeconia
dc.relation.ispartofMacedonian Journal of Chemistry and Chemical Engineering
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250323
dc.subjectSchiff base
dc.subjecttautomerism
dc.subjectphenol-imine
dc.subjectketo-amine
dc.subjectDFT
dc.subjectPES
dc.titleDEPENDENCE OF TAUTOMERISM ON SUBSTITUENT TYPE IN o-HYDROXY SCHIFF BASES
dc.typeArticle

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