The effect of the change in substituents' positions on the formation of supramolecular networks and the solvent type/substituent dependence of prototropic behavior in three new o-hydroxy Schiff bases

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dc.authoridKastas, Gokhan/0000-0002-5956-405X
dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.authoridERSANLI, CEM CUNEYT/0000-0002-8113-5091
dc.contributor.authorKastas, Gokhan
dc.contributor.authorKastas, Cigdem Albayrak
dc.contributor.authorKirca, Basak Kosar
dc.contributor.authorErsanli, Cem Cuneyt
dc.date.accessioned2025-03-23T19:39:34Z
dc.date.available2025-03-23T19:39:34Z
dc.date.issued2020
dc.departmentSinop Üniversitesi
dc.description.abstractThe effect of substituent position on the formation of supramolecular topology, intra-molecular geometry and tautomeric behavior, and the dependence of prototropy on the solvent type have been investigated applying the XRD, UV-Vis, NMR, DFT, PES and HOMA methods on three new o-hydroxy Schiff bases. Based on key geometric parameters, total molecular energy and aromaticity calculations, the XRD, DFT and HOMA studies propose the phenol-imine structure as the most consistent tautomeric form for the compounds. PES and HOMA studies give results that relate the preference of the phenol-imine form to its high p-electron delocalization. For the solvent type dependence of tautomerism, the investigation of UV-Vis and NMR spectra and the PES studies for different solvent media reveals that the co-existence of two tautomeric structures becomes easier by increasing solvent polarity. As to the effect of substituent position on the supramolecular topology, XRD studies show that different substituent positions cause different types of non-covalent inter-molecular interactions in the crystal packings of the compounds. This is resulted in a significant change in the formation and topology of the supramolecular architecture, emphasizing the importance of a substituent position as a regulator in crystal engineering. (C) 2019 Elsevier B.V. All rights reserved.
dc.description.sponsorshipSinop University Scientific Research Coordination Unit [FEF-1901-18-26]
dc.description.sponsorshipThis workwas supported by Sinop University Scientific Research Coordination Unit. Project Number: FEF-1901-18-26. The authors acknowledge to Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.
dc.identifier.doi10.1016/j.molstruc.2019.127109
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85072806727
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2019.127109
dc.identifier.urihttps://hdl.handle.net/11486/6366
dc.identifier.volume1200
dc.identifier.wosWOS:000496810900080
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectSchiff base
dc.subjectPrototropy
dc.subjectXRD
dc.subjectUV-Vis
dc.subjectNMR
dc.subjectDFT
dc.titleThe effect of the change in substituents' positions on the formation of supramolecular networks and the solvent type/substituent dependence of prototropic behavior in three new o-hydroxy Schiff bases
dc.typeArticle

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