Kinetically Stable Complexes in Water: The Role of Hydration and Hydrophobicity

Abstract

We describe here the synthesis and characterization of a molecular receptor that forms kinetically and thermodynamically stable host-guest complexes in water. This cavitand-based host is composed of a preorganized aromatic pocket whose rim is decorated with four negatively charged carboxylate groups. (1)H NMR and isothermal titration calorimetry have been used to characterize the behavior of the resulting complexes in response to changes in pH, buffer identity, and salt concentration and in the presence of sodium dodecyl sulfate micelles.