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

Abstract

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.

IUPAC-NIST Solubility Data Series. 102. Solubility of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) in Neat Organic Solvents and Organic Solvent Mixtures

“…Solution models have been used with success to rationalize the solubility behavior of a given solute molecule in a series of organic solvents. Of the models developed in recent years, the general solvation parameter developed by Abraham and coworkers [19][20][21][22][23][24][25][26][27] is probably the most widely used approach in correlating the solubilities of crystalline organic compounds. The model is based on two linear free energy relationships describing solute transfer between two immiscible phases.…”

The solubility of liquid and solid compounds in dry octan-1-ol

“…The very useful statistic, PSD, the predicted standard deviation is obtained from the leave-one-out Finally, we combine the two data sets, together with some additional compounds taken from the literature (Alexander et al, 1977;Gharavi et al, 1983;Martin, Wu and Beerbower, 1984;Niimi, 1991;Pinsuwan, Li and Yalkowsky, 1995;Bernazzani et al, 1995;Kristl and Vesnaver, 1995;Bustamante, Pena and Barra, 1998;Martinez and Gomez, 2001;Avila and Martínez, 2002;Perlovich et al, 2003Perlovich et al, , 2010Perlovich et al, , 2011Ran et al, 2002;Sepassi and Yalkowsky, 2006;Quingzhu et al, 2007Quingzhu et al, , 2008Thimmasetty et al, 2008) or from our own previous work (Fletcher et al, 1998;Hoover et al, 2004Hoover et al, , 2005aHoover et al, , 2005bHoover et al, , 2006Charlton et al, 2005;Stovall et al, 2005aStovall et al, , 2005bFlanagan et al, 2006aFlanagan et al, , 2006bHolley et al, 2011;Ye et al, 2011;Stephens et al, 2012;Wilson et al, 2012;Bowen et al, 2013). For most of the common compounds in the Admire and Raevsky data sets, the listed log Soct(mol/L) values were the same.…”

“…(13) (13) is much simpler than that of eq. (6), and eq (13) Fletcher et al, 1998;Hoover et al, 2004Hoover et al, , 2005aHoover et al, , 2005bHoover et al, , 2006Charlton et al, 2005;9 Stovall et al, 2005a9 Stovall et al, , 2005bFlanagan et al, 2006aFlanagan et al, , 2006bHolley et al, 2011;Ye et 10 al., 2011;Stephens et al, 2012;Wilson et al, 2012;Bowen et al, 2013 …”

QSPR Modeling using Catalan Solvent and Solute Parameters

“…7 Abraham solvent parameters were collected from the literature. [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] Regression analyses were performed to find the relationships between the corresponding polarity/polarizability, hydrogenbonding basicity, and hydrogen-bonding acidity scales of Abraham and Catalan.…”

“…Solute descriptors were calculated using Catalan solvent parameters (as explained above) for 27 solutes for which aqueous solubility and Abraham solute descriptors [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42] were available through recent publications. For these solutes, the new solute parameters were compared with Abraham solute descriptors in terms of: the accuracy of the original equation used for the estimation of solute parameters; and the accuracy of the models developed for the estimation of aqueous solubility of 27 solutes.…”