Atomic charges play a fundamental role in qualitative pictures of reactivity and selectivity, and are integral ingredients used to construct quantitative relationships between chemical structure and reaction outcomes. The theoretical foundations of different charge models have been described extensively, and significant effort has gone into comparing the various methods for computing atomic charge. Cramer and Truhlar charges; (III) those obtained by fitting to reproduce a physical observable, (such as dipole moment or a computed electrostatic potential) seen in the CHarges from ELectrostatic Potentials using a Grid-based method (CHELPG), Merz-Kollman charges using Universal force field radii (MKUFF), Hu, Lu, Yang charges with standard atomic densities (HLYGat) and Atomic Polar Tensor (APT) 27 charges; or (IV) those based on semi-empirical adjustments to Class II or III methods, such as in Charge Model 5 (CM5). With the above categories another important distinction arises between methods that project the molecular wavefunction onto atom-centered basis functions, like NPA, and those that are based directly on the electron density as a function of space, such as the Hirshfeld scheme. In this work we observe a distinct performance difference between these two groupings.