Solubility measurement, correlation, thermodynamic analysis and molecular simulation of 1-nitronaphthalene in twelve pure solvents

The solid–liquid equilibrium data of 1-nitronaphthalene in twelve pure solvents (methanol, ethanol, n -propanol, i-propanol, n -butanol, i-butanol, acetone, acetonitrile, dichloromethane, methyl acetate, ethyl acetate and cyclohexane) were systematically determined by isothermal saturation method in the temperatures ranging from 273.15 K to 308.15 K under atmospheric pressure (0.1 MPa). Molecular electrostatic potential surface and Hirshfeld surface analysis were applied to obtain the visual analysis of crystal structure and the overall charge distribution. The effect of solvent multiple physicochemical factors including polarity, hydrogen bond donor, hydrogen bond acceptor and cohesive energy density of solvent was explored to the solubility behavior. Then the experimental solubility data were correlated by the modified Apelblat equation, λ h equation, Van't Hoff equation and Wilson model, the ARD% was used to check the accuracy of the four equations and the modified Apelblat showed the best fitting. Furthermore, the mixing thermodynamic properties were calculated based on Wilson model, which indicates the dissolution of 1-nitronaphthalene is a spontaneous, endothermic and entropy-driving process. Finally, molecular dynamic simulations were employed to further analyze the dissolution behavior from solute-solvent interaction perspective.