The Hydrophobic Effect. 2. Relative Importance of the Hydrophobic Effect on the Solubility of Hydrophobes and Pharmaceuticals in H-Bonded Solvents

The quantitative development of the nonergodic mobile order thermodynamics involving the new interpretation of the hydrophobic effect leads to a general solubility equation. This equation is applied to predict the aqueous and alcohol solubility of chemicals ranging from nonpolar or slightly polar wi...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1998-08, Vol.87 (8), p.998-1014
Main Authors: Ruelle, Paul, Kesselring, Ulrich W.
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chemical Phenomena
Chemistry, Physical
General pharmacology
Hydrogen Bonding
Medical sciences
Pharmaceutical Preparations - chemistry
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
Solubility
Solvents - chemistry
Thermodynamics
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Summary:The quantitative development of the nonergodic mobile order thermodynamics involving the new interpretation of the hydrophobic effect leads to a general solubility equation. This equation is applied to predict the aqueous and alcohol solubility of chemicals ranging from nonpolar or slightly polar with no H-bonding capacity to polyfunctional polar compounds including pharmaceuticals. The analysis of the relative importance of the contributions involved in the solubility model [i.e., the fluidization of the solute (for solids), the correction for the mixing entropy, the change of the nonspecific cohesion forces, and the formation of solvent-solvent (hydrophobic effect), solute–solute, and solute–solvent H-bonds] unambiguously demonstrates that the hydrophobic effect is essential for predicting the aqueous or alcohol solubility of any substance in general, and of nonpolar compounds in particular. The difference between the origin of the solubility of hydrocarbons in water and of water in hydrocarbons is furthermore presented. in both cases, the quasilinear solubility dependence on the molar volume of the hydrocarbon is of an entropic nature
ISSN:0022-3549
1520-6017
DOI:10.1021/js9702980