Solubility of nonelectrolytes in polar solvents. V. Estimation of the solubility of aliphatic monofunctional compounds in water using a molecular surface area approach

G. L. Amidon, S. H. Yalkowsky, S. T. Anik, S. C. Valvani

Research output: Contribution to journalArticlepeer-review

125 Scopus citations

Abstract

The molecular surface areas for 158 aliphatic hydrocarbons, olefins, alcohols, ethers, ketones, aldehydes, esters, and fatty acids have been computed and correlated with their aqueous solubilities. The hydrocarbon and functional group contributions to the free energy of solution are compared and discussed with particular regard to the chosen standard state. The results indicate that the functional group contributions to the free energy of solution in water are nearly equivalent from the pure liquid standard state while being significantly different when the gas phase (1 mmHg) standard state is chosen. The interpretation of the differing hydrocarbon surface area slopes is shown to be complicated by mutual miscibility considerations (water solubility in the pure liquid) and by the presence of curvature for the longer chain length (greater than C10) compounds. The curvature in the alcohol and fatty acid data is shown to become very evident when correction is made to the pure (supercooled) liquid standard state for the solid compounds. Finally the surface area method is shown to hold considerable promise in its extension to the solubility estimation of complex organic molecules with limited aqueous solubilities.

Original languageEnglish (US)
Pages (from-to)2239-2246
Number of pages8
JournalJournal of physical chemistry
Volume79
Issue number21
DOIs
StatePublished - Jan 1 1975
Externally publishedYes

ASJC Scopus subject areas

  • Engineering(all)
  • Physical and Theoretical Chemistry

Fingerprint Dive into the research topics of 'Solubility of nonelectrolytes in polar solvents. V. Estimation of the solubility of aliphatic monofunctional compounds in water using a molecular surface area approach'. Together they form a unique fingerprint.

Cite this