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Synthon Modularity in 4-Hydroxybenzamide-Dicarboxylic Acid Cocrystals

Tothadi, Srinu and Desiraju, Gautam R (2012) Synthon Modularity in 4-Hydroxybenzamide-Dicarboxylic Acid Cocrystals. In: CRYSTAL GROWTH & DESIGN, 12 (12). pp. 6188-6198.

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Official URL: http://dx.doi.org/10.1021/cg3013766

Abstract

A family of 4-hydroxybenzamide-dicarboxylic acid cocrystals has been designed and subsequently isolated and characterized. The design strategy follows from an understanding of synthon modularity in crystal structures of monocomponent crystals such as gamma-quinol, 4,4'-biphenol and 4-hydroxybenzoic acid. These monocomponent structures contain infinite O-H center dot center dot center dot O-H center dot center dot center dot O-H center dot center dot center dot cooperative synthons linked with molecular connectors such as phenyl and biphenyl, and supramolecular connectors such as the acid dimer in 4-hydroxybenzoic acid. The cocrystal design was influenced by the anticipation that dicarboxylic acids can form a supramolecular connector mediated by acid-amide synthons with 4-hydroxybenzamide, which can then form the phenol O-H center dot center dot center dot O-H center dot center dot center dot O-H center dot center dot center dot infinite synthon. Effectively, the acid-amide and phenol synthons are insulated. The short axis of such a structure will be around 5.12 angstrom and this is borne out in 2:1 cocrystals of 4-hydroxybenzamide with oxalic, succinic, fumaric, glutaric (two forms) and pimelic acids. Hydrated variations of this structure type are seen in the cocrystals obtained with adipic and sebacic acids.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to AMER CHEMICAL SOC, WASHINGTON, USA
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Francis Jayakanth
Date Deposited: 15 Feb 2013 12:10
Last Modified: 15 Feb 2013 12:11
URI: http://eprints.iisc.ac.in/id/eprint/45785

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