Other oxidants like trityl cations, ketones, and triaryl boranes also exhibit hydride abstraction capabilities . Here, the QM workflow (MCC: 0.66) outperforms both the regressor (MCC: 0.56) and ALFABET (MCC: 0.63), indicating most of the reactions are controlled by a hydride transfer from the best C-H hydride donor. The regressor is underperforming compared to the other methods, most likely due to little training data. In summary, some reactions favor hydride abstraction, while others favor hydrogen abstraction or involve complex intermediates with partial charges. Substrates, catalysts, additives, or solvents can alter mechanisms, necessitating more research to understand these pathways fully. Based on the reactions we use to evaluate our QM workflow, regressor, and ALFABET, it is clear that it is nearly impossible to get a reaction dataset solely with hydride abstraction, as competing pathways often are in play. Therefore, it is important to evaluate both hydricity and BDEs as thermodynamic properties along with other factors such as sterics and kinetics. ,N-diisobutylamine, and N-(p-methoxybenzyl)-N,N-diisobutylamine where the aliphatic:benzylic ratio is 5.9:1, >20:1, and 3.7:1, respectively when reacting with the tropylium ion. They further speculate that the reaction appears to be sensitive to steric factors and an electron-donor-acceptor complex with especially aromatic substrates and the tropylium ion could alter both the reactivity and selectivity, explaining why poor efficiency to no benzylic oxidations occurs, see Figure . This explanation also aligns with what they found for the reaction between N-(p-methoxybenzyl)-N,Ndiisobutylamine, and substituting the tropylium ion with DDQ. Here, the aliphatic:benzylic selectivity ratio is reversed to 1.0:1. ). The article notes that steric and electronic effects control site selectivity, with substituted sites electronically favored but counterbalanced by steric demands. Therefore, they explore different dirhodium catalysts and find that, e.g., for Rh 2 (R-DOSP) 4 , C-H functionalization is generally preferred at secondary C-H bonds. Still, both could also occur at sterically accessible tertiary C-H bonds or electronically activated primary C-H bonds. The paper finds exceptional site selectivity for C-H functionalization when using the Rh 2 (R/S-BPCP) 4 complex due to the bulky nature of the catalyst. The catalyst is so selective that it produces no other regioisomers for Scheme 1h. This explains why we cannot predict the primary allylic C-H bond, as it is not the most thermodynamically stable reaction site but is controlled by steric effects. In summary, our QM workflow and ML model generally predict the most thermodynamically stable C-H sites. In contrast, ALFABET performs slightly worse than our QM workflow and ML model for the examples above. Discrepancies between QM and ML predictions often arise from minor energy differences or insufficient training data. Reactions are complex, and factors such as catalysts and additives can alter the reaction outcome. Therefore, theoretical predictions should be used cautiously, and the limitations of our methods should be considered. Refer to section 6 in the Supporting Information for more details.