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Equilibrium phase diagrams of the p-dichlorobenzene-hexafluorobenzene and the p-chlorotoluene-hexafluorobenzene binary systems are experimentally determined by differential scanning calorimetry and X-ray diffraction analysis and optimized by computational thermodynamic analyses. Resulting data are thermodynamically assessed through a substituted model for liquid phase and lead to the Gibbs free energy of complexation in the case of the p-chlorotoluene-hexafluorobenzene system. The first diagram is of the eutectic type, and the second one presents an equimolar complex. The comparison of these two systems with the benzene-hexafluorobenzene and the chlorobenzene-hexafluorobenzene binaries shows that the stability of the complex decreases with number of H atoms substituted by Cl atoms in the benzenic ring.