Solubility, dissolution thermodynamics, Hansen solubility parameter and molecular simulation of 4-chlorobenzophenone with different solvents

Authors：Ouyang, Jinbo^*; Liu, Lishan; Zhou, Limin; Liu, Zhirong; Li, Yunyun; Zhang, Chuntao^*

Source：Journal of Molecular Liquids, 2022, 360: 119438.

DOI：10.1016/j.molliq.2022.119438

• Solubility
• 4-chlorobenzophenone
• Dissolution
• Molecular interaction

Equilibrium mole fraction solubility of 4-chlorobenzophenone in eleven organic solvents, as well as in neat water, was determined at temperatures ranging from 278.15 K to 323.15 K. Solubility of 4-hlorobenzophenone in these solvents increased with rising of temperatures, and the data was adequately correlated with several well-known thermodynamic models with the average relative deviations (100ARD) of 0.03 to 12.91%, suggesting good correlation. The effects of solvent polarity on solubility were also investigated, and 4-chlorobenzophenone dissolved more in less polar solvents (ester solvents) than in strong polar solvents (alcohol solvents) due to the weak polarity functional groups of 4-hlorobenzophenone. Respective apparent thermodynamic functions, i.e. Gibbs energy, enthalpy, and entropy, for the dissolution process, were calculated using the Wilson equation. Results showed that the dissolution process of 4-chlorobenzophenone was endothermic and spontaneous. Furthermore, Hansen solubility parameters (HSPs) were applied to further discuss the miscibility of 4-hlorobenzophenone in the selected solvents. Molecular dynamics simulation explored the molecular interaction between 4-chlorobenzophenone and solvents, and strong interaction between 4-hlorobenzophenone and ester solvents contributed to the higher solubility.