Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 5, Issue 11, Pages 1706-1714Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b700988g
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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 (K-ass = 480 M-1 in 30% H2O-DMSO). The pyridine moiety is critical to obtaining strong binding, and comparison with the binding properties of analogous compounds in which the pyridine is replaced by a benzene ring provides a striking example of enthalpy-entropy compensation.
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