Phenyl-perfluorophenyl synthon mediated cocrystallization of carboxylic acids and amides

Reddy, L. Sreenivas ; Nangia, Ashwini ; Lynch, Vincent M. (2004) Phenyl-perfluorophenyl synthon mediated cocrystallization of carboxylic acids and amides Crystal Growth & Design, 4 (1). pp. 89-94. ISSN 1528-7483

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Official URL: http://pubs.acs.org/doi/abs/10.1021/cg034106s

Related URL: http://dx.doi.org/10.1021/cg034106s

Abstract

The significance of face-to-face π-π stacking of phenyl and perfluorophenyl rings (Ph-PhF), a robust supramolecular synthon in aromatic and perfluoroaromatic crystal structures, is studied in the cocrystallization of simple aromatic carboxylic acids and amides. X-ray crystal structures of C6H5COOHπC6F5COOH 1, C6H5CONH2πC6F5CONH2 2, and C6H5CONH2πC6F5COOH 3 are analyzed to understand the role of Ph-PhF synthon in directing self-assembly and hydrogen bonding in these cocrystals. The strong hydrogen bond donor acidity of C6F5COOH and C6F5CONH2 together with mixed stacks of phenyl and perfluorophenyl rings steer acid···acid and amide···amide hydrogen bonding in cocrystals 1 and 2. Acid···amide hydrogen bonding is sufficiently strengthened by donor acidity and acceptor basicity in 3 that the role of the Ph-PhF synthon is weaker because the aromatic rings stack with lateral offset. The complex C6H5COOH·C6F5CONH2 4 could not be obtained under similar crystallization conditions. The crystal structure of C6F5CONH2 is determined to compare molecular conformation and hydrogen bonding with motifs in the cocrystals. This study shows the viability of the Ph-PhF synthon in the presence of strong hydrogen bonding COOH and CONH2 groups for crystal engineering.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:24569
Deposited On:29 Nov 2010 08:29
Last Modified:04 Mar 2011 05:37

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