The decision tree nodes can be interpreted as being associated with the computed molecular features, which are connected to the success of product formation. The first node is defined by the calculated C NMR shift for the ispo carbon in electrophile. With a value of NMR shift > 38.1, reactions are categorized into two groups effectively identifying those with no product. While the absolute value is not directly comparable to experimental values, the relative values are accurate in comparison to each other. This decision boundary is directly related to electrophilicity. The subsequent node uses the carbon-sulfur bond distance (dC-S) in the nucleophile. Reactions involving nucleophiles with dC-S > 1.83 are classified as 'no'. This distance shows a correlation (r 2 =0.93) to nucleophile experimental pKa values, indicating the availability of sulfur for reaction (see correlation analysis, Scheme S12). The final node incorporates the sterimol B5 parameter computed for the carbon-halogen axis in the electrophile. Electrophiles with B5 < 3.3 values tend to be larger, suggesting that steric repulsion that can prevent product formation.