Tanusri Dey, K. S. Praveena, Sarbani Pal
Jun 5, 2017
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0
Influential Citations
7
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract Three oxime ether derivatives, ( E )-3-methoxy-4-(prop-2-ynyloxy)-benzaldehyde- O -prop-2-ynyl-oxime (C 14 H 13 NO 3 ) ( 2 ), benzophenone- O -prop-2-ynyl-oxime (C 16 H 13 NO) ( 3 ) and ( E )-2-chloro-6-methylquinoline-3-carbaldehyde- O -prop-2-ynyl-oxime (C 14 H 11 ClN 2 O) ( 4 ), have been synthesized and their crystal structures have been determined. The DFT optimized molecular geometries in 2 – 4 agree closely with those obtained from the crystallographic study. An interplay of intermolecular C H⋯O, C H⋯N, C H⋯Cl and C H···π(arene) hydrogen bonds and π···π interactions assembles molecules into a 2D columnar architecture in 2 , a 1D molecular ribbon in 3 and a 3D framework in 4 . Hirshfeld surface analysis showed that the structures of 2 and 3 are mainly characterized by H⋯H, H⋯C and H⋯O contacts but some contribution of H⋯N and H⋯Cl contacts is also observed in 4 . Hydrogen-bond based interactions in 2 – 4 have been complemented by calculating molecular electrostatic potential (MEP) surfaces. The electronic structures of molecules reveal that the estimated band gap in 3 , in which both aldehyde hydrogen atoms of formaldehyde- O -prop-2-ynyl-oxime ( 1 ) have been substituted by two benzene rings, is higher than that of 2 and 4 with only one aldehyde hydrogen atom replaced.