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 tem-peratures ranging from 273.15 K to 308.15 K under atmospheric pressure (0.1 MPa). Molecular electro-static 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, kh 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 indi-cates 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.(c) 2022 Elsevier B.V. All rights reserved.

Automated summary

In this study, the solid-liquid equilibrium data and solubility behavior of 1-nitronaphthalene in twelve pure solvents were systematically investigated using experimental and computational methods. It was found that the physicochemical properties of the solvents have significant effects on the solubility, and the modified Apelblat equation provided the best fitting to the experimental data. Furthermore, the calculation of mixing thermodynamic properties indicated that the dissolution of 1-nitronaphthalene is a spontaneous, endothermic, and entropy-driving process.