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Solubility of Crystalline Nonelectrolyte Solutes in Organic Solvents: Mathematical Correlation of Benzil Solubilities with the Abraham General Solvation Model

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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 form

$$\log ({{C_{S}} \mathord{\left/ {\vphantom {{C_{S}}{C_{W}}}} \right. \kern-\nulldelimiterspace} {C_{W}}}) = c + r \cdot R_2 + s \cdot {\pi }_{2}^{H} + a \cdot \sum {\alpha _2^{H} + b \cdot \sum {\beta _2^{H} + v \cdot V_{x}}}$$
$$\log ({{C_{S}} \mathord{\left/ {\vphantom {{C_{S}}{C_{G}}}} \right. \kern-\nulldelimiterspace} {C_{G}}}) = c + r \cdot R_2 + s \cdot {\pi }_{2}^{H} + a \cdot \sum {\alpha _2^{H} + b \cdot \sum {\beta _2^{H} + l \cdot \log L^{[16]} } } $$

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, C 2 is the solute excess molar refraction, V x is the McGowan volume of the solute, \(\sum {\alpha _2^{H}}\) and \(\sum {\beta _2^{H}}\) are measures of the solute hydrogen-bond acidity and basicity, \({\pi }_{2}^{H}\) 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 cm3-mol−1 and calculate V x as 163.74 cm3-mol−1, and then solve a total of 51 equations to yield \({\pi }_{2}^{H}\) = 1.59, \(\sum {\beta _2^{H}}\) = 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.

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Authors and Affiliations

  1. Department of Chemistry, University of North Texas, P.O. Box 305070, Denton, Texas, 76203-5070

    William E. Acree Jr.

  2. Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, U.K

    Michael H. Abraham

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  1. William E. Acree Jr.
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Acree, W.E., Abraham, M.H. Solubility of Crystalline Nonelectrolyte Solutes in Organic Solvents: Mathematical Correlation of Benzil Solubilities with the Abraham General Solvation Model. Journal of Solution Chemistry 31, 293–303 (2002). https://doi.org/10.1023/A:1015853220711

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