Evaluation of the interchangeability of C–H and C–F groups: insights from crystal packing in a series of isomeric fluorinated benzanilides

Chopra, Deepak and Row, Guru TN (2007) Evaluation of the interchangeability of C–H and C–F groups: insights from crystal packing in a series of isomeric fluorinated benzanilides. In: CrystEngComm, 10 (1). pp. 54-67.

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Abstract

A series of mono- and difluorinated benzanilides have been synthesized and characterized to unravel the importance of interactions involving organic fluorine. The effect of fluorine substitution on the molecular conformation and the solid-state organization of the molecules in the crystalline lattice have been discussed in terms of changes in molecular conformation and the supramolecular aggregation. It is noteworthy that the meta- and para-isomers (mono and difluorinated) are isostructural, with the ortho-isomers possessing minor conformational variations. Furthermore, the molecular conformation as obtained by theoretical DFT calculations is different from the solid-state conformation highlighting the importance of co-operative features brought by $N–H...O$ and $C–H...O$ hydrogen bonds, along with weak intermolecular interactions involving organic fluorine and aromatic $C–H...\pi$ contacts in the solid state.

Item Type:	Journal Article
Publication:	CrystEngComm
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre:	Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited:	06 Jun 2008
Last Modified:	19 Sep 2010 04:45
URI:	http://eprints.iisc.ac.in/id/eprint/14212

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