Solubility of Bis(salicylidene)-trans-1,2-cyclo-hexanediamine: Determination, Modeling, and Simulation Study

The solubility of bis(salicylidene)-trans-1,2-cyclohexanediamine (compound 1) in 12 pure solvents was determined by gravimetric analysis in the temperature range of 273.15 to 313.15 K. ¹H NMR, ¹³C NMR, and high-resolution mass spectrometry characterized the structure of compound 1. The melting point and fusion enthalpy of compound 1 were obtained by TG-DSC. The molecular electrostatic potential quantified the electrostatic potential energy of the surface. The intermolecular interaction of compound 1 was described by Hirshfeld surface analysis. The order of solubility was tetrahydrofuran > dichloromethane > 1,2-dichloroethane > toluene > acetone > ethyl acetate > methyl acetate > acetonitrile > 1-propanol > ethanol > n-hexane > methanol. The KAT-LSER model demonstrated the influence of various factors between solvents and the solute on the solubility. Moreover, seven thermodynamic models were used to correlate the solubility data. The NRTL model was determined to be the most appropriate by comparing the average relative deviation and the root mean squared deviation. The findings of this study substantially support the isolation and crystallization of such compounds.