A thermodynamic analysis of quantitative structure-activity relationships for hydrophobic organic chemicals. 1991

F A Gobas
Great Lakes Institute, University of Windsor, Ontario, Canada.

An experimental analysis is presented of the molecular interactions controlling the activity and solubility of chlorinated dibenzo-p-dioxins (PCDDs) in water. For this purpose, the enthalpy, entropy and free-energy contributions of fusion, vaporization, solvation and aqueous solution are determined. It is shown that, due to enthalpy-entropy compensation in the water, the solvation of hydrophobic organic chemicals in water is independent of molecular size, total surface area or molar volume. The observed relationship between the aqueous solubility and molar volume (or total surface area) is caused by the phenomenon that, with increasing molar volume, molecules require more energy to leave the pure (subcooled liquid) phase. This suggests that the relationship between aqueous solubility and molecular structure, and, consequently, many quantitative structure-activity relationships (QSARs) for hydrophobic organic substances, reflect molecular interactions between the solute molecules in the pure subcooled liquid phase rather than solute-water interactions.

UI MeSH Term Description Entries
D008433 Mathematics The deductive study of shape, quantity, and dependence. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed) Mathematic
D002712 Chlorides Inorganic compounds derived from hydrochloric acid that contain the Cl- ion. Chloride,Chloride Ion Level,Ion Level, Chloride,Level, Chloride Ion
D004147 Dioxins A family of compounds that contain the 1,4-dioxin structure. Many specific dioxin derivatives are listed as CARCINOGENS; TERATOGENS; or MUTAGENS. Dioxin
D012995 Solubility The ability of a substance to be dissolved, i.e. to form a solution with another substance. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 6th ed) Solubilities
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013816 Thermodynamics A rigorously mathematical analysis of energy relationships (heat, work, temperature, and equilibrium). It describes systems whose states are determined by thermal parameters, such as temperature, in addition to mechanical and electromagnetic parameters. (From Hawley's Condensed Chemical Dictionary, 12th ed) Thermodynamic

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