Structural and aromatic aspects for tautomerism of (Z)-6-((4-bromophenylamino)methylene)-2,3-dihydroxycyclohexa-2,4-dienone

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dc.authoridKARABIYIK, HASAN/0000-0001-7894-6646
dc.authoridKarabiyik, Hande/0000-0001-6180-2080
dc.authoridAlbayrak kastas, Cigdem/0000-0003-0235-7460
dc.contributor.authorKarabiyik, Hasan
dc.contributor.authorPetek, Hande
dc.contributor.authorIskeleli, Nazan Ocak
dc.contributor.authorAlbayrak, Cigdem
dc.date.accessioned2025-03-23T19:44:03Z
dc.date.available2025-03-23T19:44:03Z
dc.date.issued2009
dc.departmentSinop Üniversitesi
dc.description.abstractThe molecular and crystal structure of (Z)-6-((4-bromophenylamino)methylene)-2,3-dihydroxycyclohexa- 2,4-dienone were determined by single crystal X-ray diffraction and spectroscopic methods. Molecules of the compound can be regarded as a resonance hybrid of cis-keto tautomer and zwitterionic form. Pairs of molecules of the compound generate pseudocyclic centrosymmetric R-2(2)(10) supramolecular synthons with the aid of O-H center dot center dot center dot O type intermolecular H-bonds. Stacking of R-2(2)(10) synthons along b-axis is stabilized by pi center dot center dot center dot pi interactions. Changes in both covalent topology and molecular geometry of the compound accompanying proton transfer were monitored by a relaxed PES scan with respect to hydroxyl bond length used as redundant internal coordinate. Quantum chemical studies at 6-311 + G(d,p) level reveal that bond lengths which are indicative to tautomerization process cannot reach their expected values even if proton transfer occurs in gas phase and pseudo-aromatic chelate ring formation has primary effect on the stabilization of NH tautomer. Resonance-assisted intramolecular H-bond affects the electronic state of its neighboring aromatic fragments.
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/s11224-009-9509-x
dc.identifier.endpage1065
dc.identifier.issn1040-0400
dc.identifier.issn1572-9001
dc.identifier.issue6
dc.identifier.scopus2-s2.0-70549109028
dc.identifier.scopusqualityQ2
dc.identifier.startpage1055
dc.identifier.urihttps://doi.org/10.1007/s11224-009-9509-x
dc.identifier.urihttps://hdl.handle.net/11486/6856
dc.identifier.volume20
dc.identifier.wosWOS:000271673100013
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.subjectResonance-assisted H-bond (RAHB)
dc.subjectpi-electron coupling
dc.subjectHOMA
dc.titleStructural and aromatic aspects for tautomerism of (Z)-6-((4-bromophenylamino)methylene)-2,3-dihydroxycyclohexa-2,4-dienone
dc.typeArticle

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