Hydrogen bonds and hydrogen-bonded chains in complexes of 3-(hydroxymethyl)-2,2 '-biphenol with N-bases. FTIR and H-1 NMR studies

A new compound 3-(hydroxymethyl)-2,2'-biphenol (HMBP) was synthesized. Comp lexes of this compound with three N-bases were studied by FTIR and H-1 NMR spectroscopy. In the 1:1 mixture of HMBP and triethylamine (TEA) in chlorof orm, the complexes are formed completely. The hydrogen-bonded chain of thes e complexes shows large proton polarizability due to collective proton fluc tuation. In acetonitrile the alcoholic group of HMBP is no longer bonded to the hydrogen-bonded chain. The rest of the hydrogen-bonded chain still sho ws proton polarizability. In the 1:1 mixtures of HMBP with a stronger base 7-methyl-1,5,7-triazabicyclo [4.4.0]dec-5-ene (MTBD) the phenolic proton tr ansfers to MTBD and is localized there. In chloroform the protonated MTBD i s weakly bonded to HMBP via two other hydrogen bonds. In acetonitrile the c omplex dissociates. The complex between HMBP and urotropine is not formed c ompletely and all hydrogen bonds within this complex are asymmetrical and w eak.