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dc.contributor.authorPetek, Hande
dc.contributor.authorAlbayrak, Cigdem
dc.contributor.authorOdabaşoğlu, Mustafa
dc.contributor.authorSenel, Ismet
dc.contributor.authorBüyükgüngör, Orhan
dc.description/0000-0001-9605-2590; KARABIYIK, HANDE/0000-0001-6180-2080en_US
dc.descriptionWOS: 000279605100003en_US
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.en_US
dc.description.sponsorshipOndokuz Mayis UniversityOndokuz Mayis University [F.279, F.377]en_US
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.en_US
dc.publisherSpringer/Plenum Publishersen_US
dc.subjectSchiff baseen_US
dc.subjectSUMP instructionen_US
dc.subjectPES scanen_US
dc.subjectCrystal structureen_US
dc.titleThe proton transfer process observed in the structure analysis and DFT calculations of (E)-2-ethoxy-6-[(2-methoxyphenylimino)methyl]phenolen_US
dc.relation.journalStructural Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US

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