Determination of sets of solute descriptors from chromatographic measurements

Prediction of solubility of drugs and other compounds in organic solvents

On the preferential solvation of drugs and PAHs in binary solvent mixtures

Determination of solute descriptors by chromatographic methods.

Separation characteristics of wall-coated open-tubular columns for gas chromatography.

Solubilities of trans-stilbene in 17 nonaqueous solvents are reported. These may be combined with literature values for the solubility in water and for the vapour pressure of stilbene to give 17 values of water–solvent partitions, P, and 17 values of gas–solvent partitions, L. Coefficients in the general solvation equations (i) and (ii) are known for all 34 of these systems, together with two additional equations for gas–water partitions. In equations (i) and (ii), the independent variables are solute descriptors as follows: R2 is an excess molar refraction, π2H is the dipolarity/polarizability, Σα2H and Σβ2H are the overall hydrogen-bond acidity and basicity, Vx is the McGowan characteristic volume, and log L16 is a descriptor where L16 is the solute L-coefficient on hexadecane at 298 K.     log SP = c + rR2 + sπ2H + aΣα2H + bΣβ2H + vVx     (i)     log SP = c + rR2 + sπ2H + aΣα2H + bΣβ2H + l log L16     (ii)We estimate R2 as 1.45 and calculate Vx as 1.563, and then solve the total set of 36 equations to yield π2H = 1.04, Σα2H = 0.00, Σβ2H = 0.34 and log L16 = 7.525 units. These descriptors reproduce the 36 observed log P and log L values with a standard deviation of only 0.086 log units. This represents an entirely new method for determining solvation descriptors and is also a quite novel method for the correlation and estimation of solubilities.

/pdf/descriptors-for-solutes-from-the-solubility-of-solids-trans-3ph21y0lpa.pdf

Descriptors for solutes from the solubility of solids: trans-stilbene as an example

Experimental solubilities are reported at 25.0°C for thioxanthen-9-one dissolved in thirty-five different organic nonelectrolyte solvents containing ester-, ether-, hydroxy-, methyl- 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 26 solvents for which predictions could be made computations show that Mobile Order theory does provide fairly reasonable (although by no means perfect) estimates of the saturation mole fraction solubilities. Average absolute deviation between predicted and observed values is circa 45%. In comparison, the average absolute deviation increases significantly to 420% when ideal solution behavior is assumed.

Carmen E. Hernández

Papers

Descriptors for solutes from the solubility of solids: trans-stilbene as an example

Solubility of thioxanthen-9-one in organic nonelectrolyte solvents. Comparison of observed versus predicted values based upon mobile order theory

Solubility of pyrene in binary (alkane + 2-butanol) solvent mixtures

Solubility of anthracene in ternary (propanol + heptane + cyclohexane) and (butanol + heptane + cyclohexane) solvent mixtures

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