Dawn M. Stovall

Solubility of crystalline nonelectrolyte solutes in organic solvents: mathematical correlation of 4-chloro-3-nitrobenzoic acid and 2-chloro-5-nitrobenzoic acid solubilities with the Abraham solvation parameter model

The Abraham solvation parameter model is used to calculate the numerical values of the solute descriptors for both 4-chloro-3-nitrobenzoic acid and 2-chloro-5-nitrobenzoic acid from experimental solubilities in organic solvents. The mathematical correlations take the form of where C S and C W refer to the solute solubility in the organic solvent and water, respectively, C G is a gas phase concentration, E is the solute excess molar refraction, V is McGowan volume of the solute, A and B are measures of the solute hydrogen-bond acidity and basicity, S denotes the solute dipolarity/polarizability descriptor, and L is the logarithm of the solute gas phase dimensionless Ostwald partition coefficient into hexadecane at 298 K. The remaining symbols in the above expressions are known solvent coefficients, which have been determined previously for a large number of gas/solvent and water/solvent systems. The Abraham solvation parameter model was found to describe the experimental solubility data of 4-chloro-3-nitrobenzoic acid and 2-chloro-5-nitrobenzoic to within overall standard deviations of 0.067 and 0.113 log units, respectively.

Thermochemical behavior of dissolved carboxylic acid solutes: part 5 – mathematical correlation of 3,5-dinitrobenzoic acid solubilities with the abraham solvation parameter model

The Abraham general solvation model is used to calculate the numerical values of the solute descriptors for 2-methylbenzoic acid from experimental solubilities in organic solvents. The mathematical correlations take the form of where CS and CW refer to the solute solubility in the organic solvent and water, respectively, CG is a gas phase concentration, R 2 is the solute excess molar refraction, Vx is McGowan volume of the solute, are measures of the solute hydrogen-bond acidity and hydrogen-bond basicity, denotes the solute dipolarity/polarizability descriptor and L (16) is the solute gas phase dimensionless Ostwald partition coefficient into hexadecane at 298 K. The remaining symbols in the above expressions are known solvent coefficients, which have been determined previously for a large number of gas/solvent and water/solvent systems. We estimate R 2 as 0.7300 and calculate Vx as 1.0726, and then solve a total of 47 equations to yield = 0.8400, = 0.4200, = 0.4400 and log L (16) = 4.6770. These descriptors reproduce the observed log(C S /C W ) and log(C S /C G ) values with a standard deviation of only 0.076 log units.

Abraham model correlations for describing solute transfer into anhydrous 1,2-propylene glycol for neutral and ionic species

Abstract Experimental solubility, acid-dissociation constants (pKa) and activity coefficient data have been compiled from the published pharmaceutical and chemical literature for neutral organic molecules and ionic species dissolved in anhydrous 1,2-propylene glycol. The compiled experimental data were transformed into molar solubility ratios, water-to-anhydrous propylene glycol (P) and gas-to-anhydrous propylene glycol (K) using standard thermodynamic relationships. The derived Abraham model correlations described the observed solubility and partition coefficient data of neutral organic compounds and ionic species to within 0.18 log units and 0.18 log units (or less), respectively.

Solubility of crystalline nonelectrolyte solutes in organic solvents: Mathematical correlation of ibuprofen solubilities with the Abraham solvation parameter model

The Abraham solvation parameter model is used to calculate the numerical values of the solute descriptors for ibuprofen from experimental solubilities in organic solvents. The mathematical correlations take the form of where C S and C W refer to the solute solubility in the organic solvent and water, respectively, C G is a gas phase concentration, E is the solute excess molar refraction, V is McGowan volume of the solute, A and B are measures of the solute hydrogen-bond acidity and hydrogen-bond basicity, S denotes the solute dipolarity/polarizability descriptor and L is the logarithm of the solute gas phase dimensionless Ostwald partition coefficient into hexadecane at 298 K. The remaining symbols in the above expressions are known solvent coefficients, which have been determined previously for a large number of gas/solvent and water/solvent systems. The Abraham solvation parameter model was found to describe the experimental solubility data of ibuprofen to within an overall standard deviation of 0.109 log units.

Solubility of 9-Fluorenone in Organic Nonelectrolyte Solvents: Comparison of Observed Versus Predicted Values Based Upon Mobile Order Theory

Experimental solubilities are reported at 25.0C for 9-fluorenone dissolved in 40 different organic nonelectrolyte solvents containing ether-, chloro-, hydroxy-, cyano and t -butyl-functional groups. Results of these measurements are used to test the applications and limitations of expressions derived from Mobile Order theory. For the 29 solvents for which predictions could be made, computations show that Mobile Order theory does provide fairly reasonable estimates of the saturation mole fraction solubilities. Average absolute deviation between predicted and observed values is 39.3%.

SOLUBILITY BEHAVIOR OF CRYSTALLINE POLYCYCLIC AROMATIC HYDROCARBONS (PAHs): PREDICTION OF FLUORENE SOLUBILITIES IN ORGANIC SOLVENTS WITH THE ABRAHAM SOLVATION PARAMETER MODEL

The Abraham solvation parameter model is used to predict the experimental solubilities of fluorene in organic solvents, from the correlation equations, below, and already determined descriptors for fluorene. The mathematical correlations take the form of where C s and C w refer to the solute solubility in the organic solvent and water, respectively, C G is a gas phase concentration, E is the solute excess molar refraction, V is McGowan volume of the solute, A and B are measures of the solute hydrogen-bond acidity and hydrogen-bond basicity, S denotes the solute dipolarity/polarizability descriptor, and L is the logarithm of the solute gas phase dimensionless Ostwald partition coefficient into hexadecane at 298 K. The remaining symbols in the above expressions are known solvent coefficients, which have been determined previously for a large number of gas/solvent and water/solvent systems. The Abraham solvation parameter model was found to predict the experimental solubility data and published gas chromatographic retention data of fluorene to within an overall standard deviation of 0.109 log units.

Solubility of Xanthene in Organic Nonelectrolyte Solvents: Comparison of Observed Versus Predicted Values Based Upon Mobile Order Theory

Experimental solubilities are reported at 25.0°C for xanthene dissolved in 34 different organic nonelectrolyte solvents containing ether-, chloro-, hydroxy-, cyano and t -butyl-functional groups. Results of these measurements are used to test the applications and limitations of expressions derived from Mobile Order theory. For the 27 solvents for which predictions could be made computations show that Mobile order theory does provide fairly reasonable estimates of the saturation mole fraction solubilities. Average absolute deviation between predicted and observed values is 71.4%.

Determination of the solubilising character of 2-methoxyethyl-(dimethyl)ethylammonium tris(pentafluoroethyl)trifluorophosphate based on the Abraham solvation parameter model

Abstract Gas–liquid chromatographic retention factors have been measured for 42 different organic probes on a 2-methoxyethyl(dimethyl)ethylammonium tris(pentafluoroethyl)trifluorophosphate, ([MeoeM2EAm]+[FAP]–), stationary phase capillary column at 323 and 353 K. The measured retention factors were combined with published gas-to-liquid partition coefficient data for solutes dissolved in ([MeoeM2EAm]+[FAP]–) and with published gas-to-water partition coefficient data to yield 107 gas-to-anhydrous ionic liquid and 105 water-to-anhydrous ionic liquid partition coefficients. Abraham model correlations for describing solute transfer into ([MeoeM2EAm]+[FAP]–) were derived from the three sets of experimental partition coefficient data. The derived correlations back-calculated the experimental gas-to-([MeoeM2EAm]+[FAP]–) and water-to-([MeoeM2EAm]+[FAP]–) partition coefficient data to within 0.13 and 0.15 log units, respectively.

Abraham model correlations describing the solubilising ability of peanut oil

Experimental data have been compiled from the published literature for the logarithm of the gas-to-peanut oil partition coefficient, log K, and for the logarithm of the water-to-peanut oil partition coefficient, log P, for a series of 93 solutes having a wide range of solute polarities and hydrogen-bonding character. The two sets of partition coefficients were correlated with the Abraham solvation parameter model. The derived Abraham model correlations described the experimental log K and log P values within standard deviations of 0.13 and 0.14 log units, respectively. Principal component analysis was used to compare the solvent properties of peanut oil to four other natural oils (olive oil, soybean oil, triolein and oleyl alcohol). Peanut oil was found to be close to olive oil and soybean oil, and quite far away from triolein and oleyl alcohol.