Tomberg et al. introduced a hierarchy of directing strength for 238 different ortho DGs, which can be used to rapidly predict the regioselectivity of C-H activation in complex molecules. The 238 directing groups are extracted from 150 molecules, taken from Chen et al. , for which reaction sites are known from experiments. For each directing group, the energy of the palladacycle intermediate with H-abstraction at a specific site is calculated using B3LYP-D3/LACVP** (6-31G**, except on heavy atoms where effective core potential was used) in CH 2 Cl 2 , and compiled into a hierarchical list for the determination of the reaction site with the lowest energy. Using the hierarchy, the regioselectivity of C-H activations could be rationalized for the 150 molecules with remarkable accuracy. While this approach performs well on this dataset, it doesn't generalize well to other molecules since not all relevant DGs are covered in the work by . This is evidenced by our analysis using a dataset curated from Reaxys. Using our implementation of the method presented by Tomberg et al. (for further details see section 2), we could only obtain correct predictions for four out of ten molecules, see subsection 4.2. This underscores the necessity for more robust and versatile predictive models that can adapt to the broad spectrum of organic chemistry's structural variability.