Quantum mechanical ab initio computational studies detailing the relationships between arene-arene face-to-face binding energies and the physical properties of the aromatics will be presented. All calculations involve face-to-face interactions between benzene and variously substituted aromatics. A relationship between the aromatic quadrupole moment of the substituted aromatics and the arene-arene binding energies was investigated due to earlier success in our group relating aromatic quadrupole moments and arene-cation binding energies. A direct relationship was not found when all aromatics were grouped together; however relationships were found between subgroups of substituted aromatics and the arene-arene binding energies. The relationship between aromatic polarizability and arene-arene binding energies was also examined and was found to have the same results: dividing the aromatics into subgroups by substituent shows a correlation, however a general correlation does not exist. Finally, we examined the relationship between arene-arene face-to-face binding energies and the combined Hammett σ_p values of the aromatic substituents and this approach gave a very good correlation.