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Linear free-energy relationships for water/hexadec-1-ene and water/deca-1,9-diene partitions, and for permeation through lipid bilayers; comparison of permeation systems

2012/01/01 by Michael H. Abraham, William E. Acree · 1 citation
Chemistry · Biochemistry, Genetics and Molecular Biology · Chemical Engineering · #Analytical Chemistry and Chromatography #Lipid Membrane Structure and Behavior #Thermodynamic properties of mixtures

paper · doi:10.1039/c2nj40262a

openalex publication_date 2012/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28

Abstract

Linear free energy relationships based on Abraham descriptors have been obtained for partition from water and the gas phase into hexadec-1-ene and into deca-1,9-diene, and for permeation through egg lecithin bilayers. Comparison with equations for partition into a large number of organic solvents shows that hexadec-1-ene and deca-1,9-diene are excellent models for permeation through egg lecithin bilayers. Wet octanol is a poor model, as are all polar organic solvents. The egg lecithin bilayer is non-polar and has only weak hydrogen bond acidity and weak hydrogen bond basicity. Comparison of equations for permeation through egg lecithin bilayers, through the human intestinal membrane, through the blood-brain membrane and through human skin shows that these four permeation processes are chemically far apart. It is not possible to obtain any general model for permeation: each permeation process requires a different model system.

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