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Issue 1, 2008
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Evaluation of the interchangeability of C–H and C–F groups: insights from crystal packing in a series of isomeric fluorinated benzanilides

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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⋯π contacts in the solid state.

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

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Publication details

The article was received on 29 Jun 2007, accepted on 17 Aug 2007 and first published on 06 Sep 2007


Article type: Paper
DOI: 10.1039/B709938J
Citation: CrystEngComm, 2008,10, 54-67
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    Evaluation of the interchangeability of C–H and C–F groups: insights from crystal packing in a series of isomeric fluorinated benzanilides

    D. Chopra and T. N. Guru Row, CrystEngComm, 2008, 10, 54
    DOI: 10.1039/B709938J

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