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Aakeröy, Christer B; Beatty, Alicia M; Helfrich, Brian A
Journal of the American Chemical Society, 12/2002, Letnik: 124, Številka: 48Journal Article
The X-ray crystal structure determinations of twelve cocrystals involving iso-nicotinamide and a variety of carboxylic acids have revealed a very consistent pattern of hydrogen-bond preferences. The combination of a monocarboxylic acid, an amide, and a pyridine moiety leads, in every case, to discrete “supermolecules” (consisting of two molecules of iso-nicotinamide and two molecules of the relevant carboxylic acid) with well-defined and robust connectivity. The two dominant (regularly occurring) supramolecular synthons in these crystal structures are (1) the heteromeric carboxylic acid···pyridine hydrogen bond and (2) a self-complementary amide···amide hydrogen-bond interaction, both of which prevail in the presence of widely differing chemical functionalities. In four of these cocrystals, a dicarboxylic acid is employed, which alters the structural outcome from discrete entities to infinite assemblies (or to a hexameric complex in a “U-shaped” dicarboxylic acid), which is fully expected since the two primary supramolecular synthons remain intact. This structural study shows that iso-nicotinamide is a supramolecular reagent that can produce well-defined supermolecules (containing carboxylic acids) in very high yields.
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