Bisacodyl in aqueous co-solvent solutions of isopropanol/methanol/ethanol: Solubility modeling, preferential solvation and density functional theory study
JOURNAL OF CHEMICAL THERMODYNAMICS(2023)
摘要
At the microscopic level, quantitative analysis of molecular surface was used to highlight the electrostatic properties of acidity/basicity of bisacodyl. The -C = O and -N = groups are the principal targets of electrophilic attack because they have the lowest global electrostatic potentials, ranging from -157.6 kJmol-1 to -144.8 kJmol-1. The Hirshfeld partition analysis-based independent gradient model was used to visually examine the weak interactions between bisacodyl and the solvents, including methanol, ethanol, isopropanol, and water. The isothermal shake-flask method was used to evaluate the bisacodyl solubility in three aqueous co-solvent blends of isopropanol, methanol, and ethanol, under 101.2 kPa. The solubility data of bisacodyl in neat methanol is increased from 5.507 to 44.86 to 10-4 when the temperature rose from 278.15 to 323.15 K, whereas it climbed from 1.134 to 17.94 to 10-4 in neat isopropanol. The solubility variation is mostly caused by solvent-solvent interactions, which are explained by the solubility parameter, and solute-solvent interactions, which are explained by the dipolarity-polarizability of the solute. Three models-the Jouyban-Acree model, the modified van't Hoff-Jouyban-Acree-model, and the modified Wilson model were used to analyze the connection between solubility and experimental temperature and cosolvent composition, producing the largest relative average deviation of 9.41%. At temperatures between 293.15 K and 313.15 K, the preferred solvation of bisacodyl was examined using a method based on inverse Kirkwood-Buff integrals. The preferred solvation parameters of bisacodyl had positive values in the medium and rich concentrations of isopropanol/NMP (taken from a published work)/methanol/ethanol, suggesting that bisacodyl was preferentially solvated by these solvents. A quartic polynomial formulation of the interaction term as a function of the Hildebrand solubility parameter using an EHSA was used to accurately describe the solubility of bisacodyl in the four solutions. The dissolution of bisacodyl was entropy-driven process in all solvent mixtures.
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关键词
Bisacodyl, Solubility, Preferential solvation, Solvent effect, Enthalpy -entropy compensation, Quantitative molecular surface analysis
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