SOLUBILITY PREDICTIONS FOR SOLID NITRILES AND TERTIARY AMIDES BASED ON THE MOBILE ORDER THEORY

The solubilities of hexadecanenitrile, octadecanenitrile, N,N-diphenyl capramide, and N,N-diphenyl lauramide are predicted in common organic nonelectrolyte solvents using the solubility equation derived from th e mobile order theory. In the framework of this theory, the formation of hydrogen bonds is treated on the basis of stability constants. Two values characterizing the nitrile-alcohol and the tertiary amide-alcoh ol hydrogen bonds, 175 and 600 cm(3) mol(-1), respectively, are determ ined. Although the formation of solute-solvent specific molecular inte ractions brings about a net increase in the solubility, the solubiliti es of the nitriles and amides in alcohols remain lower than those meas ured in nonassociated solvents because of the large negative hydrophob ic effect of the alcohol molecules.