Rapid estimation of octanol-water partition coefficients using synthesized vesicles in electrokinetic chromatography.
Vesicle electrokinetic chromatography (VEKC) using vesicles synthesized from the oppositely charged surfactants cetyltrimethylammonium bromide (CTAB) and sodium octyl sulfate (SOS) and from the double-chained anionic surfactant bis(2-ethylhexyl)sodium sulfosuccinate (AOT) was applied to the indirect measurement of octanol-water partition coefficients (log Po/w). A variety of small organic molecules with varying functional groups, pesticides, and organic acids were evaluated by correlating log Po/w and the logarithm of the retention factor (log k') and comparing the calibrations. A linear solvation energy relationship (LSER) analysis was conducted to describe the retention behavior of the vesicle systems and compared to that of octanol-water partitioning. The solute hydrogen bond donating behavior is slightly different with the vesicle interactions using CTAB-SOS vesicles as compared to the octanol-water partitioning model. The AOT vesicle and octanol-water partitioning systems showed similar partitioning characteristics. VEKC provides rapid separations for determinations of log Po/w in the range of 0.5 to 5 using CTAB-SOS vesicles and 0 to 5.5 using AOT vesicles.
Klotz
W L
WL
Department of Chemistry, Villanova University, Villanova, PA 19085, USA. wklotz@rohmhaas.com
Schure
M R
MR
Foley
J P
JP
D000077286:Cetrimonium; D002593:Cetrimonium Compounds / Q000737:chemistry; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D009795:Octanes / Q000737:chemistry; D000442:Octanols / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D002593:Cetrimonium Compounds; D009795:Octanes; D000442:Octanols; D014867:Water; C034597:octyl-2-sulfate; D000077286:Cetrimonium