Controlling the formation of benzoic acid: isonicotinamide molecular complexes

Colin C Seaton, Andrew Parkin, Chick Wilson, Nicholas Blagden

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The formation of crystalline molecular complexes of benzoic acid and isonicotinamide with 1:1 and 2:1 compositions has been investigated through solution cocrystallization. The 1:1 complex was solely obtained from ethanol solutions, while either complex could be grown from aqueous and methanol solution by variation of the initial composition. The crystal structures of the 2:1 complex and a monohydrate of isonicotinamide were determined by single crystal X-ray diffraction. The intermolecular interactions in the crystal structure of the complex were compared with other published carboxylic acid:isonicotinamide molecular complexes, which highlights the robust nature of the acid···pyridine and acid···amide hydrogen bond, which exist in most cases. Complementary computational studies into the binding of pairs of these molecules by ab initio calculations were found to support the experimental observations and highlight the role of solvent in controlling the final crystalline form for multicomponent systems, through altering the hierarchy of intermolecular interactions.
Original languageEnglish
Pages (from-to)47-56
Number of pages10
JournalCrystal Growth and Design
Issue number1
Early online date19 Nov 2008
Publication statusPublished - 7 Jan 2009


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