Dimeric self-assembly of pyridyl guanidinium-carboxylates in polar solvents

Ashiq, Muhammad. Irfan, Tesfatsion, Biniam. F., Gaggini, Francesca, Dixon, Sally and Kilburn, Jeremy D. (2010) Dimeric self-assembly of pyridyl guanidinium-carboxylates in polar solvents. Chemistry - A European Journal, 16 (41), 12387-12397. (doi:10.1002/chem.201001861). (PMID:20857461)

Abstract

A series of pyridyl guanidinium–carboxylates has been prepared and the dimeric self-assembly of these studied in H2O/DMSO mixtures, principally using dilution isothermal calorimetry. Compounds 5 and 6, incorporating an aromatic ring in the “tethering” region between the guanidinium and carboxylate groups, demonstrate the strongest dimerisation in neat DMSO. X-ray crystal structures of 5 and 6 reveal two different dimerisation architectures in the solid-state, but both involve carboxylate–guanidinium salt bridges as anticipated, and ?–? interactions. Compounds 10–16 incorporating peptidic fragments between the guanidinium and carboxylate groups, showed reduced dimerisation strength with increased amino acid content, but also sustained dimerisation under increasingly aqueous conditions, up to 50?% H2O/DMSO in the case of 14 and 15. The extent of our study in H2O/DMSO mixtures was determined by substrate solubility of 10–16, and not the limit of self-assembly.

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Contributors

Author: Sally Dixon

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