Carboxylate binding in polar solvents using pyridylguanidinium salts

RJ Fitzmaurice, F Gaggini, N Srinivasan…

Index: Fitzmaurice, Richard J.; Gaggini, Francesca; Srinivasan, Natarajan; Kilburn, Jeremy D. Organic and Biomolecular Chemistry, 2007 , vol. 5, # 11 p. 1706 - 1714

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Citation Number: 22

Abstract

A series of thiourea and guanidinium derivatives have been prepared and their ability to bind a carboxylate group has been investigated. Guanidinium 33, featuring two additional amides and a pyridine moiety, proved to be the most potent carboxylate binding site and was able to bind acetate in aqueous solvent systems (Kass= 480 M− 1 in 30% H2O–DMSO). The pyridine moiety is critical to obtaining strong binding, and comparison with the binding ...