Guest Recognition in a Partially Bridged Deep Cavitand

The synthesis of a new deep cavitand partially bridged via disulfide bonds is described. Its thermodynamic and kinetic complexation parameters are compared with those of an unbridged analogue. The disulfide bridges cause deviations in Delta H and Delta S but result in only small differences in Delta G of complexation. The bridges increase the activation barrier for guest dissociation and lead to complexes with enhanced kinetic stability.