Solid–liquid phase equilibrium and thermodynamic analysis of novel thiazolidine-2,4-dione derivative in different solvents

Abstract

Novel (5Z)-3-(3-(4-acetylpiperazin-1-yl)-2-hydroxypropyl)-5-(4-chlorobenzylidene)thiazolidine-2,4-dione was synthesized as a potent antimicrobial agent. Its melting enthalpy and melting point temperature were measured to be 44.4 kJ∙mol−1 and 433.9 K, respectively. The solubility of the compound studied was determined in pharmaceutically and industrially relevant organic solvents within the temperature range of 293.15–313.15 К. The solubility was found to increase in the systems with the following solvents: hexane, buffer рН 7.4, buffer рН 2.0, 1-octanol, 1-propanol, ethanol, and methanol. The compound solubility values were correlated by the modified Apelblat equation, two-suffix Margules and Wilson models with good agreement. The activity coefficients at infinite dilution and excess thermodynamic functions of the compound in eaсh solvent were calculated. The compound ability to disperse, polar and hydrogen interactions were described using Hansen solubility parameters. The temperature dependences of the distribution coefficients of the compound in 1-octanol/buffer (pH 2.0 and 7.4) two-phase systems were determined. The distribution process was characterized as thermodynamically favorable, endotermic and entropy-driven.