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

A new compound 3-(hydroxymethyl)-2,2'-biphenol (HMBP) was synthesized. Complexes 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 chloroform, the complexes are formed completely. The hydrogen-bonded chain of these complexes shows large proton polarizability due to collective proton fluctuation. In acetonitrile the alcoholic group of HMBP is no longer bonded to the hydrogen-bonded chain. The rest of the hydrogen-bonded chain still shows 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 transfers to MTBD and is localized there. In chloroform the protonated MTBD is weakly bonded to HMBP via two other hydrogen bonds. In acetonitrile the complex dissociates. The complex between HMBP and urotropine is not formed completely and all hydrogen bonds within this complex are asymmetrical and weak.