A CYCLIC HYDROGEN-BONDED SYSTEM WITH COLLECTIVE PROTON MOTION IN BIS[3,3'-(2,2'-DIHYDROXYBIPHENYL)]METHANE

Bis[3,3'-(2,2'-dihydroxybiphenyl)]methane(BBPM) was synthesized. It was studied by osmometry and by H-1 NMR and FTIR spectroscopies. Furthermore, the monotetrachloroaurate of BBPM was also investigated. BBPM is a monomer in acetonitrile solution. Within this molecule the four OH groups form a cyclic hydrogen-bonded structure in which a collective proton fluctuation occurs. In the case of the monotetrachloroaurate the cyclic structure is more stable, the additional OH group is also hydrogen-bonded, and its proton is involved in the collective proton fluctuation, as in the case of crown ethers.