Hydrazide as a New Hydrogen-Bonding Motif for Resorcin[4]arene-Based Molecular Capsules

Abstract

The resorcin[4]arene-based benzoylhydrazide cavitands formed stable molecular capsules in nonpolar solvents by the eight intermolecular N-H...O=C hydrogen bondings, two from each four paired hydrazides, and the four intramolecular O-H2C-O...H-N hydrogen bondings on each cavitand. The stability of these molecular capsules depends on the encapsulated guest in the following order: CH3SO3(-) > CH3CO2(-) > CH3CH2NH2 x HCl approximately = CH3NH2 x HCl > (CH3)4N(+) > toluene > C2D2Cl4.