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

Org Lett. 2003 Oct 16;5(21):4003-6. doi: 10.1021/ol035624z.

Abstract

[reaction: see text] 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 (DeltaH degrees ) of 3.0 kcal/mol for the binding of an acetate ion when compared to the case without the intramolecular H-bonding.