Solubility of p-Nitrobenzeneacetonitrile in 16 Pure Solvents: Thermodynamic Correlation, Molecular Simulation, and Solvent Effect Analysis

The molar solubility of p -Nitrobenzeneacetonitrile (PNBC) in 16 pure organic solvents was determined gravimetrically over the temperature range of 272.15 to 323.65 K at 101.3 kPa. Five thermodynamic models, namely the modified Apelblat, λh , NRTL, Wilson and Yaws models, were applied to correlate the solubility data, with the Yaws and modified Apelblat models showing the highest fitting accuracy. Molecular electrostatic potential surface (MEPS) analysis identified nitro oxygen and cyano nitrogen as the main hydrogen-bond acceptor sites of PNBC. Density functional theory (DFT) calculations further elucidated solute-solvent interaction energies and the underlying intermolecular interaction mechanisms. KAT-LSER model analysis revealed that solvent dipole/polarizability ( π *) promotes PNBC solubility, while hydrogen-bonding acidity ( α ) and basicity ( β ) exert inhibitory effects. Mixing thermodynamic properties (Δ mix G , Δ mix H , Δ mix S ) calculated via the Wilson model indicated that the mixing process of PNBC with solvents is spontaneous, entropy-driven, and endothermic. This work establishes a reliable PNBC solubility database, and clarifies its dissolution mechanism from macro to micro scales, offering critical thermodynamic support for the industrial crystallization and purification of PNBC.