Hydrophobicity of carbohydrates and related hydroxy compounds.

The hydrophobic interaction of carbohydrates and other hydroxy compounds with a C18-modified silica gel column was measured with pure water as eluent, thereby expanding the range of measurements already published. The interaction is augmented by structure strengthening salts and decreasing temperature. Although the interaction of the solute with the hydrophobic interface is expected to only imperfectly reflect its state in aqueous bulk solution, the retention can be correlated to hydration numbers calculated from molecular mechanics studies given in the literature. No correlation can be established towards published hydration numbers obtained by physical methods (isentropic compressibility, O-17 NMR relaxation, terahertz spectroscopy, and viscosity). The hydrophobicity is discussed with respect to the chemical structure. It increases with the fraction and size of hydrophobic molecular surface regions.