Molecular recognition of anions through hydrogen bonding stabilization of anion-ionophore adducts: A novel trifluoroacetophenone-based binding motif

A novel trifluoroacetophenone-based binding motif has been developed that recognizes anions such as carboxylates through reversible formation of anion-ionophore adducts; that are stabilized by intramolecular H-bonding. The intramolecular H-bonding resulted in more than 10-fold enhancement in the binding affinity and an enthalpy gain (DeltaHdegrees) of 3.0 kcal/mol for the binding of an acetate ion when compared to the case without the intramolecular H-bonding.