The proton transfer process observed in the structure analysis and DFT calculations of (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol

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dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.authoridKarabiyik, Hande/0000-0001-6180-2080
dc.contributor.authorPetek, Hande
dc.contributor.authorAlbayrak, Cigdem
dc.contributor.authorOdabasoglu, Mustafa
dc.contributor.authorSenel, Ismet
dc.contributor.authorBuyukgungor, Orhan
dc.date.accessioned2025-03-23T19:44:02Z
dc.date.available2025-03-23T19:44:02Z
dc.date.issued2010
dc.departmentSinop Üniversitesi
dc.description.abstractThe crystal and molecular structures of an o-hydroxy Schiff base derivative, (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol, have been determined by single crystal X-ray diffraction analyses at 296 and 100 K. The results from temperature-dependent structural analysis regarding the tautomeric equilibrium of the compound were interpreted with the aid of quantum chemical calculations. To clarify the tautomerization process and its effects on the molecular geometry, the gas-phase geometry optimizations of two possible tautomers of the title molecule, its OH and NH form, were achieved using DFT calculations with B3LYP method by means of 6-31 + G(d,p) basis set. In order to describe the potential barrier belonging to the phenolic proton transfer, nonadiabatic Potential Energy Surface (PES) scan was performed based on the optimized geometry of the OH tautomeric form by varying the redundant internal coordinate, O-H bond distance. The Harmonic Oscillator Model of Aromaticity (HOMA) indices were calculated in every step of the scan process so as to express the deformation in the aromaticities of principal molecular moieties of the compound. The results show that there is a dynamic equilibrium between the aromaticity level of phenol and chelate ring and furthermore pi-electron coupling affecting overall molecule of the title compound. Charge transfer from phenol ring to pseudo-aromatic chelate ring increases with increasing temperature, whereas pi-electron transfer from chelate ring to anisole ring is decreased as temperature increases. The most strength intramolecular H-bonds are observed for conformers close to transition state.
dc.description.sponsorshipOndokuz Mayis University [F.279, F.377]
dc.description.sponsorshipThe authors wish to acknowledge Ondokuz Mayis University for the use of the STOE IPDS 2 diffractometer purchased under grants F.279 and F.377.
dc.identifier.doi10.1007/s11224-010-9598-6
dc.identifier.endpage690
dc.identifier.issn1040-0400
dc.identifier.issn1572-9001
dc.identifier.issue4
dc.identifier.scopus2-s2.0-77954426597
dc.identifier.scopusqualityQ2
dc.identifier.startpage681
dc.identifier.urihttps://doi.org/10.1007/s11224-010-9598-6
dc.identifier.urihttps://hdl.handle.net/11486/6855
dc.identifier.volume21
dc.identifier.wosWOS:000279605100003
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherSpringer/Plenum Publishers
dc.relation.ispartofStructural Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectSchiff base
dc.subjectTautomerism
dc.subjectSUMP instruction
dc.subjectHOMA
dc.subjectPES scan
dc.subjectCrystal structure
dc.titleThe proton transfer process observed in the structure analysis and DFT calculations of (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenol
dc.typeArticle

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