Solubility predictions for crystalline nonelectrolyte solutes dissolved in organic solvents based upon the Abraham general solvation model

2001 ◽  
Vol 79 (10) ◽  
pp. 1466-1476 ◽  
Author(s):  
William E Acree, Jr. ◽  
Michael H Abraham
Keyword(s):  
Hydrogen Bond ◽  
Gas Phase ◽  
Organic Solvents ◽  
Molar Refraction ◽  
Solvation Model ◽  
Absolute Deviation ◽  
Solubility Behavior ◽  
Water Solvent ◽  
Solubility Predictions ◽  
Hydrogen Bond Acidity

The Abraham general solvation model is used to predict the saturation solubility of crystalline nonelectrolyte solutes in organic solvents. The derived equations take the form of log (CS/CW) = c + rR2 + sπ2H + aΣα2H + bΣβ2H + vVx and log (CS/CG) = c + rR2 + sπ2H + aΣα2H + bΣβ2H + l log L(16) where CS and CW refer to the solute solubility in the organic solvent and water, respectively, CG is a gas-phase concentration, R2 is the solute's excess molar refraction, Vx is McGowan volume of the solute, Σα2H and Σβ2H are measures of the solute's hydrogen-bond acidity and hydrogen-bond basicity, π2H denotes the solute's dipolarity and (or) polarizability descriptor, and log L(16) is the solute's gas-phase dimensionless Ostwald partition coefficient into hexadecane at 298 K. The remaining symbols in the above expressions are known equation coefficients, which have been determined previously for a large number of gas–solvent and water–solvent systems. Computations show that the Abraham general solvation model predicts the observed solubility behavior of anthracene, phenanthrene, and hexachlorobenzene to within an average absolute deviation of about ±35%.Key words: solubility predictions, organic solvents, nonelectrolyte solutes, partition coefficients.

Thermochemical behavior of dissolved carboxylic acid solutes: Solubilities of 3-methylbenzoic acid and 4-chlorobenzoic acid in organic solvents

2003 ◽  
Vol 81 (12) ◽  
pp. 1492-1501 ◽  
Author(s):  
Charlisa R Daniels ◽  
Amanda K Charlton ◽  
Rhiannon M Wold ◽  
William E Acree, Jr. ◽  
Michael H Abraham
Keyword(s):  
Hydrogen Bond ◽  
Gas Phase ◽  
Molar Refraction ◽  
Solvation Model ◽  
Chlorobenzoic Acid ◽  
Solubility Behavior ◽  
Water Solvent ◽  
Experimental Solubility Data ◽  
Hydrogen Bond Acidity ◽  
Alcohol Solvents

The Abraham general solvation model is used to correlate the solubility behavior of 3-methylbenzoic acid and 4-chlorobenzoic acid in alcohol and ether solvents. The mathematical correlations take the form of [Formula: see text] [Formula: see text] where CS and CW refer to the solute solubility in the organic solvent and water, respectively; CG is a gas-phase concentration; R2 is the solute excess molar refraction; Vx is the McGowan volume of the solute; ΣαH2 and ΣβH2 are measures of the solute hydrogen-bond acidity and hydrogen-bond basicity; πH2 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. The Abraham general solvation model was found to describe the experimental solubility data and published literature partitioning data of 3-methylbenzoic acid and 4-chlorobenzoic acid to within overall standard deviations of 0.079 log units and 0.085 log units, respectively. Key words: 3-methylbenzoic acid solubilities, 4-chlorobenzoic acid solubilities, alcohol solvents, partition coefficients, molecular solute descriptors, solubility predictions.

Solubility of crystalline nonelectrolyte solutes in organic solvents — Mathematical correlation of 2-methoxybenzoic acid and 4-methoxybenzoic acid solubilities with the Abraham solvation parameter model

2004 ◽  
Vol 82 (9) ◽  
pp. 1353-1360 ◽  
Author(s):  
Kaci R Hoover ◽  
Dawn M Stovall ◽  
Eric Pustejovsky ◽  
Rodrick Coaxum ◽  
Krisztina Pop ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Gas Phase ◽  
Organic Solvents ◽  
Molar Refraction ◽  
Solvation Parameter Model ◽  
Water Solvent ◽  
Mathematical Correlation ◽  
Solvation Parameter ◽  
Methoxybenzoic Acid ◽  
Solute Descriptors

The Abraham solvation parameter model is used to calculate the numerical values of the solute descriptors for 2-methoxybenzoic acid and 4-methoxybenzoic acid from experimental solubilities in organic solvents. The mathematical correlations take the form of [Formula: see text] [Formula: see text] where CS and CW refer to the solute solubility in the organic solvent and water, respectively, CG is a gas phase concentration, E is the solute excess molar refraction, V is the 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 and published literature partitioning data of 2-methoxybenzoic acid and 4-methoxybenzoic acid to within overall standard deviations of 0.146 log units and 0.114 log units, respectively.Key words: 2-methoxybenzoic acid solubilities, 4-methoxybenzoic acid solubilities, partition coefficients, molecular solute descriptors, solubility predictions.

Solubility of diphenyl sulfone in organic nonelectrolyte solvents. Comparison of observed versus predicted values based upon the general solvation model

1999 ◽  
Vol 77 (7) ◽  
pp. 1214-1217 ◽  
Author(s):  
Kristin A Fletcher ◽  
Carmen E Hernández ◽  
Lindsay E Roy ◽  
Karen S Coym ◽  
William E Acree, Jr.
Keyword(s):  
Organic Solvent ◽  
Organic Solvents ◽  
Predictive Ability ◽  
Molar Refraction ◽  
Solvation Model ◽  
Absolute Deviation ◽  
Diphenyl Sulfone ◽  
Solubility Behavior ◽  
Aqueous Solvent ◽  
Equilibrium Data

Experimental solubilities are reported for diphenyl sulfone dissolved in 8 alkane, 10 alcohol, and in aqueous solvent media at 25°C. Results of these measurements are used to test the predictive ability of the general solvation model log CA,orgsat/CA,aqsat = c + rR2 + sπ2H + aΣα2H + bΣβ2H + vVxwhere CA,orgsat and CA,aqsat refer to the solute solubility in the organic solvent and in water, respectively, R2 is the solute's excess molar refraction, Vx is the McGowan characteristic volume of the solute, π2H denotes the solute's dipolarity/ polarizability, and Σα2H and Σβ2H are the overall hydrogen-bond acidity and basicity descriptors for the solute. The remaining symbols in the above expression are known solvent coefficients, which have been determined previously through regressional analysis of published organic solvent - water partition coefficient and vapor-liquid equilibrium data. Computations show that the general solvation model predicts the solubility behavior of diphenyl sulfone in the 11 organic solvents for which predictions could be made to within an overall average absolute deviation of about ±20%. Key words: diphenyl sulfone solubilities, organic solvents, solubility predictions, general solvation model.

The solubility of gases and vapours in ethanol - the connection between gaseous solubility and water-solvent partition

1998 ◽  
Vol 76 (6) ◽  
pp. 703-709 ◽  
Author(s):  
Michael H Abraham ◽  
Gary S Whiting ◽  
Wendel J Shuely ◽  
Ruth M Doherty
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Correlation Equation ◽  
Strong Hydrogen Bond ◽  
Log P ◽  
Water Solvent ◽  
Chemical Factors ◽  
Solubility Of Gases ◽  
Solubility Coefficients ◽  
Hydrogen Bond Acidity

Ostwald solubility coefficients, as log L, for solutes in water and ethanol have been combined to give log PEtOH for partition between the two pure solvents. Sixty-four such values have been correlated through our solvation equation, the coefficients of which lead to the conclusion that ethanol and water solvents are equally strong hydrogen-bond bases, but that ethanol is much weaker as a hydrogen-bond acid. A slightly different solvation equation has been used to correlate 68 values of log LEtOH; the coefficients in this equation yield the same conclusions as to the hydrogen-bond acidity and basicity of bulk ethanol. In addition, an analysis of the various terms in the log LEtOH correlation equation allows the elucidation of the various chemical factors that govern the solubility of gaseous solutes in ethanol solvent at 298 K.Key words: solubility, partition, hydrogen-bonding, ethanol, water.

Gas Phase Detection of the NH–P Hydrogen Bond and Importance of Secondary Interactions

2015 ◽  
Vol 119 (44) ◽  
pp. 10988-10998 ◽  
Author(s):  
Kristian H. Møller ◽  
Anne S. Hansen ◽  
Henrik G. Kjaergaard
Keyword(s):  
Hydrogen Bond ◽  
Gas Phase ◽  
Phase Detection ◽  
Secondary Interactions

Solubility of the pesticide diuron in organic nonelectrolyte solvents. Comparison of observed vs. predicted values based upon Mobile Order theory

2000 ◽  
Vol 78 (2) ◽  
pp. 184-190 ◽  
Author(s):  
Karina M De Fina ◽  
Tina L Sharp ◽  
Michael A Spurgin ◽  
Ivette Chuca ◽  
William E Acree, Jr. ◽  
...  
Keyword(s):  
Order Theory ◽  
Average Absolute Deviation ◽  
Absolute Deviation ◽  
Solubility Predictions ◽  
Mobile Order Theory ◽  
Dimethyl Urea ◽  
Organic Nonelectrolyte ◽  
Predicted Values ◽  
Alcohol Solvents ◽  
Mobile Order

Experimental solubilities are reported at 25.0°C for diuron (also called 3-(3,4-dichlorophenyl)-1,1-dimethyl urea) dissolved in 49 different organic nonelectrolyte solvents containing ether-, chloro-, hydroxy-, ester-, methyl-, and tert-butyl-functional groups. Results of these measurements are used to test the applications and limitations of expressions derived from Mobile Order theory. For the 28 nonalcoholic 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 60.1%. Diuron solubilities in the alcohol solvents are used to calculate stability constants for presumed solute-solvent hydrogen bonds that are believed to occur in solution.Key words: pesticide, diuron solubilities, organic nonelectrolyte solvents, solubility predictions.

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