In an effort to circumvent the use of quantum chemical calculations to predict regioselectivity using well-established electronic descriptors without the need for quantum chemical calculations, we applied Hammett parameters to experimental ortho (N-heteroarene-only), meta, and para positions in N-heteroarenes (Supplementary Section 6.7). Summing the Hammett parameters for each functional group at every active site resulted in an accuracy of 53% when compared to the ground truth (Supplementary Section 6.7). We attribute this relatively low accuracy to the possibility that the relationship between Hammett parameters and alkylation regioselectivity is not additive. Consequently, we turned to other methods to better understand and predict this complex relationship.