Computational work in our group has shown a direct relationship between arene-cation binding energies and the aromatic quadrupole moment. Thus, an ability to predict the aromatic quadrupole moment based on the substitution pattern would allow for easy prediction of arene-cation binding energies. We will present computational work detailing the development of substituent constants for the prediction of aromatic quadrupole moments based on the substitution pattern. The accuracy of the approach will be discussed along with the ability of the predicted quadrupole moments to estimate cation-arene binding energies. Finally we will discuss the effects of aromatic substituent rotation on the aromatic quadrupole moment and how this affects cation binding.