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Abstract

The Abraham general solvation model is used to calculate the numerical values of the solute descriptors for benzil from experimental solubilities in organic solvents. The mathematical correlations take the formwhere C S and C W refer to the solute solubility in the organic solvent and water, respectively, C G is a gas-phase concentration, R 2 is the solute excess molar refraction, V x is the McGowan volume of the solute, fi H 2 and fl H 2 are measures of the solute hydrogenbond acidity and basicity, … H 2 denotes the solute dipolarity/polarizability descriptor, and L [16] is the solute gas-phase dimensionless Ostwald partition coefficient into hexadecane at 25 • C. 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 14.45 cm 3 -mol −1 and calculate V x as 163.74 cm 3 -mol −1 , and then solve a total of 51 equations to yield … H 2 = 1.59, fl H 2 = 0.620 and log L [16] = 7.6112. These descriptors reproduce the 51 observed log(C S /C W ) and log(C S /C G ) values with a standard deviation of only 0.115 log units.

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

“…35 Standard deviations for aspirin dissolved in 13 alcohols, 4 ethers, and ethyl ethanoate were 0.123 and 0.138 log 10 units. 25 Benzil 48 and aspirin 25 exhibited solubilities exceeding 1 molar in several of the organic solvents studied. In the case of aspirin it could be argued that the model's success relates back to when the equation coefficients were originally calculated for the dry solvents.…”