A Structural Study of Tautomerism and Hydrogen-Bonding in Supramolecular Assemblies |
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| Authors: | Michael M. Bishop Simon J. Coles Andrew H.W. Lee Andrew Parkin Oliver T. Thorn-Seshold |
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| Affiliation: | 1. Sydney Grammar School , College Street, Darlinghurst, NSW, 2010, Australia;2. School of Chemistry, University of Southampton, EPSRC National Crystallography Service , Southampton, SO17 1BJ, UK;3. University of Glasgow, Department of Chemistry , Glasgow, G12 8QQ, UK |
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| Abstract: | The synthesis and X-ray structures of four new crystalline materials incorporating ’dimers’ assembled from two different units possessing complementary hydrogen bonding motifs are reported; namely, phthalimide and 3-iminoisoindolinone or 2-guanidinobenzimidazole (or selected methylated derivatives) and 2-guanidinobenzoxazole. The bonding within each dimer involves a triplet of hydrogen bonds. The extended supramolecular structures are compared with each other as well as with two related structures described previously. The effect of using complementary DAD/ADA motifs that are not symmetrical on the respective supramolecular structures is also examined as is the prospect of incorporating different tautomeric components into the supramolecular structures. The presence of a very short, proton-transferred hydrogen bond within the respective triplets is also discussed. |
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| Keywords: | Crystal engineering Self-assembly Supramolecular Hydrogen bonding |
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