Linear Free Energy Relationship Correlation of the Distribution of Solutes between Water and Sodium Dodecyl Sulfate (SDS) Micelles and between Gas and SDS Micelles Page: 1,808
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J. Chem. Inf Model. 2007, 47, 1808-1817
Linear Free Energy Relationship Correlation of the Distribution of Solutes between
Water and Sodium Dodecyl Sulfate (SDS) Micelles and between Gas and SDS Micelles
Laura Sprunger,t William E. Acree, Jr.,*,t and Michael H. Abraham,
Department of Chemistry, P.O. Box 305070, University of North Texas, Denton, Texas 76203-5070, and
Department of Chemistry, University College London, 20 Gordon Street, London WC1H OAJ, U.K.
Received May 22, 2007
Data have been assembled from the published literature on the water-to-micellar sodium dodecyl sulfate
(SDS) partition coefficient data for more than 200 compounds and on the gas-to-micellar SDS partition
coefficient data for more than 140 compounds. It is shown that an Abraham solvation equation with only
five descriptors can be used to correlate the observed partition coefficient data to within a standard deviation
of 0.22 log units. Micellar electrokinetic chromatographic (MEKC) retention factor data measured on a
micellar SDS pseudostationary phase was also gathered from the literature. The water-to-micellar SDS partition
coefficient and MEKC retention factor data were combined into a single database and correlated with the
Abraham model. The derived correlation described the 486 experimental values to within a standard deviation
of 0.15 log units. The micellar SDS system has been compared to various liquid phases in terms of solubility
of gases and vapors and has been shown to be a very selective system-more so than room-temperature
The contamination of soils, sediments, and groundwater
by hazardous organic materials is a widespread environmen-
tal concern. Hydrophobic organic contaminants (HOCs) are
of particular interest because such compounds are strongly
sorbed to soils/sediments, and remediation through desorption
is often a very expensive, time-consuming process due to
the compounds' low aqueous solubilities. Surfactant en-
hanced remediation has been suggested as a viable means
for removal of adsorbed HOCs from soils and sediments.
Published studies have shown that enhanced aqueous solu-
bilization of HOC is achieved in the presence of dissolved
surfactants, particularly at surfactant concentrations above
their critical micelle concentration (cmc). The enhanced
solubilization phenomena observed in aqueous micellar
solutions not only is important in desorption of organic
pollutants from soils/sediments but also is used in numerous
industrial processes, such as protein purification, micellar
catalysis, and drug product formulation.
The enhanced solubility is due to the partitioning of the
organic solute into the micellar phase. Solute transfer from
the bulk aqueous phase to the micellar region is governed
by a partition coefficient, which can be mathematically
described in either mole fraction concentration units
P mole fraction of solute in micellar phase
P mole fraction of solute in aquous phase
mole fraction of solute in aquous phase
or molar concentrations
S=molarity of solute in micellar phase
c molarity of solute in aquous phase
* Corresponding author e-mail: email@example.com.
t University of North Texas.
University College London.
where the solute concentrations in the corresponding phases
are measured near infinite dilution. Sepulveda et al.' reviewed
several experimental solubility and spectroscopic methods
that are used to measure micelle-water partition coefficients.
The authors compiled available partition coefficient data for
solutes in aqueous micellar sodium dodecyl sulfate (SDS),
hexadecyltrimethylammonium bromide (CTAB), dodecylt-
rimethylammonium bromide (DTAB), and hexadecyltrim-
ethylammonium chloride solutions. Additional data compi-
lations are available for sodium dodecyl sulfate2 and
hexadecylpyridinium chloride3 micellar solution. Each pub-
lished correlation contains experimental data for fewer than
200 solutes per surfactant.
To address the scarcity of measured aqueous-micellar
partition coefficient data, researchers have turned to predic-
tive methods as a means to generate desired values. Valsaraj
and Thibodeaux4 observed that there was a good correlation
between the logarithm of the molar SDS-water partition
coefficient log Pc,SDS/water, and the logarithm of the 1-octanol/
water partition coefficient, log POTOH/water
log Pc,SDS/water = 0.32 + 0.827 log POTOHwater (3)
(N= 57, R = 0.9924)
whenever aliphatic amides and lactams were excluded.
Abraham et al. later reanalyzed all of the partition coefficient
data and found
log Pc,SDS/water = 0.740 + 0.693 log POTOH/water (4)
(N = 63, R = 0.9224, SD = 0.38, F = 348)
where N denotes the number of data points, R is the
correlation coefficient, SD refers to the standard deviation,
and F is the Fisher F-statistic. Valsaraj and Thibodeaux also
developed a bond contribution method as well as a group
10.1021/ci700174q CCC: $37.00 2007 American Chemical Society
Published on Web 07/27/2007
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Sprunger, Laura M.; Acree, William E. (William Eugene) & Abraham, M. H. (Michael H.). Linear Free Energy Relationship Correlation of the Distribution of Solutes between Water and Sodium Dodecyl Sulfate (SDS) Micelles and between Gas and SDS Micelles, article, July 27, 2007; [Washington, D.C.]. (digital.library.unt.edu/ark:/67531/metadc172345/m1/1/: accessed September 25, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.