Models for Liquid–Liquid Partition in the System Ethylene Glycol–Organic Solvent and Their Use for Estimating Descriptors for Organic Compounds

Karunasekara, Thushara; Poole, Colin F.

doi:10.1007/s10337-011-1996-4

Cited by 28 publications

(9 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…All 3 also have the advantage of not being limited to a specific partition system. Both COSMOtherm and SPARC require only the molecular structure of the partitioning chemical and the partition phases as input information (except for polymers; see Materials and Methods and Model implementations for more details), and ABSOLV requires the molecular structure of the chemical and calibrated linear solvation energy relationship (LSER) system parameters for all concerned partition systems; the latter are available for a large number of systems [9][10][11][12][13][14][15][16][17]. Over the years, we have also collected system parameters from the literature in a database that is now publicly available [18].…”

Section: Introductionmentioning

confidence: 99%

Prediction of partition coefficients for complex environmental contaminants: Validation of COSMOtherm, ABSOLV, and SPARC

Stenzel

Goss

Endo

2014

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

Prediction of partition coefficients is essential for screening of environmentally relevant compounds. Prediction methods using only the molecular structure as input are especially useful for this purpose. In the present study, the authors validated 3 prediction method-COSMOtherm, ABSOLV, and SPARC-which are based on more mechanistic approaches than most other quantitative structure-activity relationships. Validation was based on a consistent experimental data set of up to 270 compounds, mostly pesticides and flame retardants. The validation systems included 3 gas chromatographic (GC) columns and 4 liquid/liquid systems that represent all relevant types of intermolecular interactions. Results revealed that the overall prediction accuracy of COSMOtherm and ABSOLV is comparable, whereas SPARC performance is substantially lower than the other methods. For instance, the root mean squared error for the 4 liquid/liquid partition coefficients was 0.65 log units to 0.93 log units for COSMOtherm, 0.64 log units to 0.95 log units for ABSOLV, and 1.43 to 2.85 log units for SPARC. In addition, version and parameterization influences of COSMOtherm on the prediction accuracy were determined.

show abstract

Section: Introductionmentioning

confidence: 99%

Prediction of partition coefficients for complex environmental contaminants: Validation of COSMOtherm, ABSOLV, and SPARC

Stenzel

Goss

Endo

2014

Enviro Toxic and Chemistry

View full text Add to dashboard Cite

show abstract

“…For several of the comparisons the author likely utilized solute parameters/properties rather than solvent parameters/properties because the required information was not readily available. This was particularly true in the case of the Abraham model as solvent parameters (called process or solvent equation coefficients) had been determined for about 300 water/organic solvent, air/organic solvent, and totally organic solvents biphasic partitioning systems [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Abraham model solvent equation coefficients were not available for solvents such as acetic acid, pyridine, propionitrile, diethyl phthalate, limonene, α-pinene, α-terpineol, glycerol and 1,3-propanediol.…”

Section: Introductionmentioning

confidence: 99%

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

Sedov

Stolov

Hart

et al. 2015

Journal of Molecular Liquids

View full text Add to dashboard Cite

Infinite dilution activity coefficients (γ∞) were measured at 298 K for 12 different aliphatic hydrocarbons (alkanes, cycloalkanes, alkenes), 11 different aromatic compounds (benzene, alkylbenzenes, halobenzenes, naphthalene), and 2-chloro-2-methylpropane dissolved in 2-butoxyethanol at 298 K using a headspace gas chromatographic method. As part of the experimental study solubilities of 19 crystalline nonelectrolyte solutes (2-hydroxybenzoic acid, acetylsalicylic acid, 3,5-dinitro-2-methylbenzoic acid, acenaphthene, trans-stilbene, xanthene, phenothiazine, 3,5-dinitrobenzoic acid, 3-chlorobenzoic acid, 2-methylbenzoic acid, 4-chloro-3-nitrobenzoic acid, 2-chloro-5-nitrobenzoic acid, benzoic acid, 4-aminobenzoic acid, benzil, thioxanthen-9-one, 3-nitrobenzoic acid, fluoranthene, and diphenyl sulfone) were determined in 2-butoxyethanol at 298 K using a static, spectrophotometric method. The experimental values 2 were converted to gas-to-2-butoxyethanol, water-to-2-butoxyethanol partition coefficients, and molar solubility ratios using standard thermodynamic relationships. Abraham model correlations for solute transfer into 2-butoxyethanol were derived from the calculated partition coefficients and solubility ratios. The derived Abraham model describes the observed partition coefficient and solubility data to within 0.14 log units (or less).

show abstract

“…The system constants for the totally organic biphasic systems are summarized in Table 2 [82][83][84][85][86][87][88][89][90][91]. The models may differ slightly from the cited references as they have been updated to include results for recently determined partition coefficients and also improved estimates for descriptor values for some compounds.…”

Section: System Constants For Totally Organic Biphasic Systemsmentioning

confidence: 99%

Totally organic biphasic solvent systems for extraction and descriptor determinations

Poole

Karunasekara

Ariyasena

2012

J of Separation Science

Self Cite

View full text Add to dashboard Cite

Partition between two immiscible solvents is widely used in sample preparation procedures for matrix simplification and isolation of target analytes, for separations using countercurrent, centrifugal partition, and liquid-liquid chromatography, and as a method for determining descriptors for use in modeling chemical, biological, and environmental processes. Until recently, most applications employed water as one component of the biphasic system. For compounds of low water solubility or stability, a series of totally organic biphasic systems have been developed to enhance the application range of liquid-liquid partition methods. These systems, their characterization using the solvation parameter model, and applications to sample preparation and the determination of descriptors are described in this review.

show abstract

Models for Liquid–Liquid Partition in the System Ethylene Glycol–Organic Solvent and Their Use for Estimating Descriptors for Organic Compounds

Cited by 28 publications

References 26 publications

Prediction of partition coefficients for complex environmental contaminants: Validation of COSMOtherm, ABSOLV, and SPARC

Prediction of partition coefficients for complex environmental contaminants: Validation of COSMOtherm, ABSOLV, and SPARC

Abraham model correlations for describing solute transfer into 2-butoxyethanol from both water and the gas phase at 298K

Totally organic biphasic solvent systems for extraction and descriptor determinations

Contact Info

Product

Resources

About