Erin Hart

Abraham model correlations for describing solute transfer into ionic liquid solvents: calculation of ion-specific equation coefficients for the 4,5-dicyano-2-(trifluoromethyl)imidazolide anion

Gas-to-ionic liquid (IL) partition coefficients have been compiled from the published literature for solutes dissolved in anhydrous 1-butyl-3-methylimidazolium 4,5-dicyano-2-(trifluoromethyl)imidazolide, ([BMIm]+[TDI]–), and 3-methyl-N-butylpyridinium 4,5-dicyano-2-(trifluoromethyl)imidazolide, ([3-MBPy]+[TDI]–). The compiled partition coefficients were converted to water-to-IL partition coefficients using the corresponding gas-to-water partition coefficients. Both sets of partition coefficients were analysed using the ion-specific equation coefficient version of the Abraham solvation parameter model. Equation coefficients are determined for the first time for 4,5-dicyano-2-(trifluoromethyl)imidazolide. Mathematical correlations derived from the Abraham model describe the observed gas-to-IL and water-to-IL partition coefficient data to within a standard deviation of 0.07 and 0.11 log units, respectively.

Determination of Abraham model solute descriptors for isophthalic acid from experimental solubility data in organic solvents at 298 K

ABSTRACT Experimental solubilities have been measured for isophthalic acid dissolved in eleven primary alcohol, three secondary alcohol and three alkoxyalcohol solvents at 298 K. Results of the experimental measurements, combined with published solubility data for isophthalic acid in ethyl acetate, acetic acid, acetophenone, acetone, cyclohexanone, propyl acetate, N-methyl-2-pyrrolidone and tetrahydrofuran, were used to determine the Abraham model solute descriptors for isophthalic acid. The calculated solute descriptors described the measured solubility data to within an overall average standard deviation of 0.15 log units.

Abraham model enthalpy of solvation correlations for solutes dissolved in dimethyl carbonate and diethyl carbonate

Experimental data have been compiled from the published chemical and engineering literature on the enthalpies of solvation for 80 different inorganic gases and organic vapours in diethyl carbonate and for 57 different gaseous compounds in dimethyl carbonate. The compiled data are used to derive mathematical correlations based on the Abraham solvation parameter model. The derived expressions describe the experimental solvation enthalpies in diethyl carbonate and dimethyl carbonate to within standard deviations of 2.1 and 2.7 kJ mol−1, respectively.

Determination of Abraham model solute descriptors for 2-methyl-3-nitrobenzoic acid from measured solubility data in alcohol, alkyl ether, alkyl acetate and 2-alkoxyalcohol mono-solvents

ABSTRACT Spectroscopic methods are employed to measure the solubility of 2-methyl-3-nitrobenzoic acid dissolved in 10 alcohol, 3 alkyl ether, 5 alkyl acetate and 3 alkoxyalcohol solvents at 298.2 K. 2-Methyl-3-nitrobenzoic acid is believed to exist in monomeric form in each of the organic solvents studied. The measured solubilities are used to calculate the Abraham model solute descriptors for the monomeric form of 2-methyl-3-nitrobenzoic acid, which will enable one to predict the solubility of 2-methyl-3-nitrobenzoic acid in additional organic solvents. The derived solute descriptors back-calculated the observed solubility data to within 0.06 log units.

Abraham model enthalpy of solvation correlations for solutes dissolved in 1-alkanol solvents (C4–C6)

Experimental data have been compiled from the published literature pertaining to enthalpies of solvation of inorganic gases and organic solutes dissolved in 1-butanol, 1-pentanol and 1-hexanol at 298 K. It is shown that the Abraham model can be used to satisfactorily correlate the measured enthalpies of solvation in 1-butanol, 1-pentanol and 1-hexanol to within standard deviations of 2.86 kJ/mole for 131 data points, 2.67 kJ/mole for 92 data points and 2.89 kJ/mole for 84 data points, respectively. The derived equations were validated by training set and test set analyses.

Abraham model expressions for describing water-to-organic solvent and gas-to-organic solvent partition coefficients for solute transfer into anhydrous poly(ethylene glycol) dialkyl ether solvents at 298.15 K

ABSTRACT Henry’s law constants and infinite dilution activity coefficients were compiled from the published chemical and engineering literature for gaseous solutes and organic liquids in butyl diglyme, butyl triglyme and tetraglyme. The published literature values were converted into water-to-liquid and gas-to-liquid partition coefficients using standard thermodynamic relationships. The calculated partition coefficients were correlated mathematically with the Abraham solvation parameter model. The derived Abraham model correlations can be used to predict the partitioning behaviour of additional solutes into dry, anhydrous butyl diglyme, butyl triglyme and tetraglyme.

Development of Abraham model correlations for describing the transfer of molecular solutes into propanenitrile and butanenitrile from water and from the gas phase

ABSTRACT Experimental solubilities were measured for 20 crystalline organic solutes dissolved in propanenitrile and for 13 crystalline organic solutes dissolved in butanenitrile at 298.15 K. Infinite dilution activity coefficient data for solutes dissolved in propanenitrile and butanenitrile have been compiled from the published chemical and engineering literature and converted into gas-to-liquid partition coefficients and water-to-organic solvent partition coefficients through standard thermodynamic relationships. Abraham model correlations were developed for describing solute transfer into both propanenitrile and butanenitrile by combining our measured solubility data with the partition coefficients that we calculated from the published activity coefficient data. The derived Abraham model correlations were found to back-calculate the observed partition coefficients and molar solubility data to within 0.14 log units.

Solubility of sorbic acid in organic mono-solvents: calculation of Abraham model solute descriptors from measured solubility data

ABSTRACT Experimental mole fraction solubilities are reported for sorbic acid dissolved in methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-propanol, 2-methyl-2-propanol, 2-pentanol, diisopropyl ether, methyl tert-butyl ether, tetrahydrofuran and 1,4-dioxane at 298.15 K. Results of the experimental measurements, combined with a published water-to-octanol partition coefficient and published solubility data for sorbic dissolved in acetone, ethyl acetate and acetonitrile, were used to calculate Abraham model solute descriptors for the sorbic acid monomer. The calculated solute descriptors were found to describe the measured solubility and partition coefficient data to within 0.10 log units. The calculated solute descriptors can be used to predict sorbic acid solubilities at 298.15 K in additional organic solvents in which sorbic acid is expected to exist predominately in monomeric form.

Development of Abraham model expressions for predicting the enthalpies of solvation of solutes dissolved in acetic acid

ABSTRACT Experimental data have been compiled from the published chemical and engineering literature on the enthalpies of solvation for 92 different inorganic gases and organic vapours in acetic acid. The compiled data are used to derive mathematical correlations based on the Abraham solvation parameter model. The derived expressions describe the experimental solvation enthalpies in acetic acid to within a standard deviation (SD) of 2.2 kJ mol−1. Principal Component Analysis (PCA) on the five equation coefficients from a derived Abraham model correlation shows that acetic acid does not resemble hydroxylic solvents in terms of enthalpic interactions, but is more akin to moderately polar solvents such as ethyl acetate or acetone.

Determination of Abraham Model Correlations for Solute Transfer into Propyl Acetate Based on Experimental Activity Coefficient and Solubility Data

Experimental infinite dilution activity coefficients, gas-to-liquid partition coefficients, and molar solubility data have been measured for numerous organic solutes dissolved in propyl acetate. Results of our experimental measurements, combined with published solubility data retrieved from the published literature, have been used to derive Abraham model correlations for describing solute transfer into propyl acetate. The derived Abraham model correlations describe the experimental data to within 0.11 log10 units. Calculation of Abraham model solute descriptors for boscalid was illustrated using our derived solute transfer correlations into propyl acetate. Predictions using the calculated solute descriptors indicate that boscalid would show significant partitioning into the skin and fat tissues in the body, and would exhibit considerable baseline toxicity towards the eight aquatic organisms (five fish species and three water flea species).