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

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

Content Provider	Springer Nature Link
Author	Karabıyık, Hasan Petek, Hande İskeleli, Nazan Ocak Albayrak, Çiğdem
Copyright Year	2009
Abstract	The 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···O type intermolecular H-bonds. Stacking of $$ R_{2}^{2} (10) $$ synthons along b-axis is stabilized by π···π 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.
Starting Page	1055
Ending Page	1065
Page Count	11
File Format	PDF
ISSN	10400400
Journal	Structural Chemistry
Volume Number	20
Issue Number	6
e-ISSN	15729001
Language	English
Publisher	Springer US
Publisher Date	2009-09-16
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Schiff base Tautomerism Resonance-assisted H-bond (RAHB) π-electron coupling HOMA Theoretical and Computational Chemistry Physical Chemistry Computer Applications in Chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Condensed Matter Physics

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