Solvent and concentration dependence of the hydroxyl chemical shift of methanol

Proton NMR chemical shift measurements of the hydroxyl proton in methanol were made as a function of concentration in six solvents: carbon tetrachloride, benzene, chloroform, acetonitrile, acetone and dimethyl sulphoxide. The hydroxyl proton peak shifts by approximately 5 ppm in carbon tetrachloride and benzene, and by lesser amounts in the other solvents. This behaviour is due to hydrogen bonding interactions of the methanol with other methanol molecules or with the solvent, and is correlated with nb initio estimates of solute-solvent hydrogen bond energies.