Supramolecular features of 2-(chlorophenyl)-3-[(chlorobenzylidene)-amino]-2,3-dihydroquinazolin-4(1 H )-ones: A combined experimental and computational study

Mandal, Arkalekha ; Patel, Bhisma K. (2018) Supramolecular features of 2-(chlorophenyl)-3-[(chlorobenzylidene)-amino]-2,3-dihydroquinazolin-4(1 H )-ones: A combined experimental and computational study Journal of Molecular Structure, 1155 . pp. 78-89. ISSN 0022-2860

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Official URL: https://www.sciencedirect.com/science/article/abs/...

Related URL: http://dx.doi.org/10.1016/j.molstruc.2017.10.085

Abstract

The molecular structures of two isomeric 2-(chlorophenyl)-3-[(chlorobenzylidene)-amino] substituted 2,3-dihydroquinazolin-4(1H)-ones have been determined via single crystal XRD. Both isomers contain chloro substitutions on each of the phenyl rings and as a result a broad spectrum of halogen mediated weak interactions are viable in their crystal structures. The crystal packing of these compounds is stabilized by strong N−H⋯O hydrogen bond and various weak, non-classical hydrogen bonds acting synergistically. Both the molecules contain a chiral center and the weak interactions observed in them are either chiral self-discriminatory or chiral self-recognizing in nature. The weak interactions and spectral features of the compounds have been studied through experimental as well as computational methods including DFT, MEP, NBO and Hiresfeld surface analyses. In addition, the effect of different weak interactions to dictate either chiral self-recognition or self-discrimination in crystal packing has been elucidated.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:2,3-Dihydroquinazolin-4(1H)-one; Chiral Self-recognition; Chiral Self-discrimination; Interhalogen Interaction; Hirsfeld Surface Analyses
ID Code:114025
Deposited On:02 May 2018 04:52
Last Modified:02 May 2018 04:52

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