Intramolecular versus intermolecular hydrogen bonding in solution

Abstract

The balance between intra- and intermolecular hydrogen bonding is studied for a solution of methyl beta-cellobioside in water and dimethylsulfoxide by 1H NMR and molecular dynamics simulations. In water O(3) predominantly interacts with water molecules, whereas in dimethylsulfoxide it is intramolecularly hydrogen bonded to O(5Œ). The temperature coefficient of the chemical shift of the hydroxy groups appears to be a reliable indicator of intermolecular hydrogen-bond formation, whereas the exchange rate is not.