Collect. Czech. Chem. Commun. 2004, 69, 1137-1148

(Thio)Urea-Functionalized Cavitands as Excellent Receptors for Organic Anions in Polar Media

Gennady V. Oshovsky, Willem Verboom* and David N. Reinhoudt

Laboratory of Supramolecular Chemistry and Technology, MESA+ Research Institute, University of Twente, P.O. Box 217, 7500 AE Enschede, The Netherlands


Ureidocavitand 1 and thioureidocavitand 2 bind in CH3CN organic anions such as acetate, propionate, butyrate, etc. with K values of 2-8 × 105 l mol-1 and 2-9 × 106 l mol-1, respectively, as was determined with isothermal microcalorimetry (ITC). Bringing together four (thio)urea binding sites on a molecular platform gives rise to about 2000 times higher binding constants, compared with those of the corresponding single binding sites. Glucose- and galactose-containing thioureidocavitands 5 and 6 bind acetate in 1:1 CH3CN/water with a K-value of 2.15 × 103 l mol-1.

Keywords: Anions; Binding constants; Cavitands; Microcalorimetry; Receptors; Glycosides; Carboxylates; Recognition.

References: 44 live references.