Noncovalent Catch and Release of Carboxylates in Water

Association constants of a bis-(acetylguanidinium)ferrocene dication to various (di)carboxylates were determined through U-vis titrations. Association constant values greater than 10(4) M-1 were determined for both phthalate and maleate carboxylates to the his(acetylguanidinium)ferrocene salt in pure water. Density functional theory computations of the binding enthalpy of the rigid carboxylates for these complexes agree well with the experimentally determined association constants. Catch and release competitive binding experiments were done by NMR for the cation carboxylate ion-pair complexes with cucurbit[7]uril, and they show dissociation of the ion-pair complex upon addition of cucurbit[7]uril and release of the free (di)carboxylate.