Single stranded helical chains of C-H鈰€ interactions further connected by halogen-halogen interactions of type I to construct supramolecular structure of (E)-5-(diethylamino)-2-[(4-iodophenylimino)methyl]phenol compound

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• 作者：Gö ; khan Ka艧ta艧^a ; ^{gkastas@omu.edu.tr} ; Ç ; i臒dem Albayrak^b ; Mustafa Odaba艧o臒lu^c ; René ; Frank^d
• 关键词：Schiff base ; Intramolecular hydrogen bond ; Intermolecular hydrogen bond ; Halogen&ndash ; halogen interaction ; Tautomerism ; Helical chain
• 刊名：Spectrochimica Acta Part A ; Molecular and Biomolecular Spectroscopy
• 出版年：2012
• 期刊代码：99_13861425
• 类别：ch
• 出版时间：August, 2012
• 卷：94
• 期：Complete
• 页码：200-204
• 文件大小：742 K

摘要

In this study, (E)-5-(diethylamino)-2-[(4-iodophenylimino)methyl]phenol compound was investigated from the point of stacking interactions assembling the supramolecular network, conformational isomerism and tautomerism. For this purpose, X-ray diffraction, FT-IR and UV/Vis spectroscopic techniques were used, giving the following structural and spectroscopic properties of the compound: The title compound has two conformers (anti and eclipsed) in the crystal structure resulting from rotation about C-N single bond of ethyl group. Both conformers prefer enol form in the solid state, adopting E configuration about the CN double bond. The supramolecular architecture of the compound is constructed by two non-covalent interactions as C-H鈰€ and halogen-halogen interactions. The repetition of C-H鈰€ interactions is resulted in a single-stranded helical structure. The helical structures are further connected by C-I鈰疘-C interactions of Type I to construct the two dimensional supramolecular network defined as (6,3)-net in Wells nomenclature. The title compound adopts both enol and keto forms in EtOH (a polar and protic solvent) while enol form is preferred in the solid state.