Linear solvation energy relationships: 36. Molecular properties governing solubilities of organic nonelectrolytes in water

Molar solubilities of non-hydrogen bond donor and weak hydrogen bond donor liquid aliphatic solutes in water, or the nearly equivalent quantities, Sg/Kgw, where Kgw is the gas-water partition coefficient and Sg is the solute concentration in the solute saturated vapor (Sg = Patm/24.5) are well corre...

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Published inJournal of pharmaceutical sciences Vol. 75; no. 4; p. 338
Main Authors Kamlet, M J, Doherty, R M, Abboud, J L, Abraham, M H, Taft, R W
Format Journal Article
LanguageEnglish
Published United States 01.04.1986
Subjects
Alcohols
Chemical Phenomena
Chemistry, Physical
Hydrogen Bonding
Kinetics
Solubility
Water
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Summary:Molar solubilities of non-hydrogen bond donor and weak hydrogen bond donor liquid aliphatic solutes in water, or the nearly equivalent quantities, Sg/Kgw, where Kgw is the gas-water partition coefficient and Sg is the solute concentration in the solute saturated vapor (Sg = Patm/24.5) are well correlated by the equation: log Sw congruent to log (Sg/Kgw) = 0.54 - 3.32V/100 + 0.46 pi* + 5.17 (beta or beta m) (at 25 degrees C) n = 105, r = 0.9954, SD = 0.137 V is the solute molar volume (the molecular weight divided by the liquid density at 20 degrees C), and pi* and beta are the solvatochromic parameters that are measures of solute dipolarity-polarizability and hydrogen bond acceptor basicity. The equation, which applies to liquid monofunctional aliphatic solutes is used to calculate additional new beta and beta m values. The beta m values, which are intended to apply to self-associated compounds when acting as "monomer" solutes, are: methanol, 0.42; all primary alkanols, 0.45; all secondary alkanols, 0.51; and all tertiary alkanols, 0.57.
ISSN:0022-3549
DOI:10.1002/jps.2600750405