HYDROGEN-BONDING IN NON-CYCLIC VICINAL DIOLS AND THEIR MONO-METHYL ETHERS: AN FTIR STUDY

Article abstract of DOI:10.1016/0022-2860(91)87029-H

Thirteen vicinal diols and their mono-alkyl ethers, dissolved in CCl4 and CS2, have been studied in the fundamental OH-stretching region.These systems are predominantly present in the intramolecular H-bonded form.The frequencies of the OH donor appears to be mainly determined by two effects: the character of the donor and its molecular surroundings.The frequency decreases on going over from primary to secondary and tertiary OH groups.The difference in the molecular surroundings is related to shielding of the H bond from the solvent and is expressed in a decrease ofthe frequency.For the diols evidence is found for a double, cyclic intramolecular H bond next to a single H bond in which one OH acts as a donor and another one as an acceptor.The proton of an acceptor OH is present in a preferential position and the corresponding OH frequency is increased with respect to the mono-hydroxy analogue.