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.
Restricted to Registered users only
Download (1158Kb) | Request a copy
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|
|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|
Actions (login required)