Cyclic hydrogen bond arrays: vibrational spectroscopic study of aminomethyl-substituted resorcinarene-based cavitands and their clathrates with THF

Mono- and tetrakis(aminomethyl)-substituted resorcinarene-based cavitands 1 and 2 and their clathrates 1 2·THF and 2·(THF)2 were investigated by FTIR spectroscopy and thermogravimetric analysis. Both hosts form stable clathrates with THF both in solution and in the solid state. Major intra- and intermolecular interactions could be identified and located by the use of vibrational spectroscopy. In all cases, dynamic cyclic intramolecular hydrogen bonds between the amino groups and neighbouring ether bridges are observable.