Abstract
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 the 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–alcohol hydrogen bonds, 175 and 600 cm3 mol−1, respectively, are determined. Although the formation of solute–solvent specific molecular interactions brings about a net increase in the solubility, the solubilities of the nitriles and amides in alcohols remain lower than those measured in nonassociated solvents because of the large negative hydrophobic effect of the alcohol molecules.
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REFERENCES
P. L. Huyskens. Thermodynamic and spectroscopic entities. J. Mol. Liquids 46:285–296 (1985).
P. L. Huyskens and G. G. Siegel. Fundamental questions about entropy. III. A kind of mobile order in liquids: Preferential contacts between molecular groups. Bull. Soc. Chim. Belg. 97:821–824 (1988).
G. G. Siegel, P. L. Huyskens, and L. Vanderheyden. Competition between solute-solvent and solvent-solvent hydrogen bonds: pyridines in alcohols and in water. Ber. Bunsen-Ges. Phys. Chem. 94:549–553 (1990).
P. L. Huyskens. Mobile and static molecular disorder in liquids. J. Mol. Struct. 274:223–246 (1992).
P. Ruelle, C. Rey-Mermet, M. Buchmann, Hô Nam-Tran, U. W. Kesselring, and P. L. Huyskens. A new predictive equation for the solubility of drugs based on the thermodynamics of mobile disorder. Pharm. Res. 8:840–850 (1991).
P. Ruelle, M. Buchmann, Hô Nam-Tran, and U. W. Kesselring. The mobile order theory versus UNIFAC and regular solution theory-derived models for predicting the solubility of solid substances. Pharm. Res. 9:788–791 (1992).
P. Ruelle, M. Buchmann, and U. W. Kesselring. The hydrophobic effect at the origin of the low solubility of inert solid substances in hydrogen-bonded solvents. J. Pharm. Sci. (in press).
P. Ruelle, M. Buchmann, Hô Nam-Tran, and U. W. Kesselring. Comparison of the solubility of polycyclic aromatic hydrocarbons in non-associated and associated solvents: The hydrophobic effect. Int. J. Pharm. 87:47–57 (1992).
P. Ruelle, M. Buchmann, Hô Nam-Tran, and U. W. Kesselring. Enhancement of the solubilities of polycyclic aromatic hydrocarbons by weak hydrogen bonds with water. J. Comput.-Aided Mol. Design 6:431–448 (1992).
P. Ruelle, M. Buchmann, Hô Nam-Tran, and U. W. Kesselring. Application of the mobile order theory to the prediction of aqueous solubility of chlorinated benzenes and biphenyls. J. Environ. Sci. Technol. 27:266–270 (1993).
P. Ruelle, E. Sarraf, L. Van Den Berge, K. Seghers, M. Buchmann, and U. W. Kesselring. The effect of proton-acceptor sites of the solute on its solubility in proton-donor solvents. Pharm. Acta Helv. 68:49–60 (1993).
C. W. Hoerr, E. F. Binkerd, W. O. Pool, and A. W. Ralston. Solubilities of high molecular weight normal aliphatic nitriles. J. Org. Chem. 9:68–80 (1944).
A. W. Ralston, C. W. Hoerr, and W. O. Pool. Solubilities of some normal aliphatic amides, anilides, and N,N-diphenyl-amides. J. Org. Chem. 8:473–488 (1943).
C. W. Hoerr and H. J. Harwood. Solubilities of high molecular weight aliphatic compounds in n-hexane. J. Org. Chem. 16:779–791 (1951).
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Ruelle, P., Kesselring, U.W. Solubility Predictions for Solid Nitriles and Tertiary Amides Based on the Mobile Order Theory. Pharm Res 11, 201–205 (1994). https://doi.org/10.1023/A:1018990904867
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DOI: https://doi.org/10.1023/A:1018990904867