To further show the value of our approach, we sought to apply the ds2 models to real examples from the cycloaddition literature given the popularity of the distortion/interaction model in this field. The papers selected examined the reaction of cyclic dienes with various cycloalkenones and cyclopropene reactions with butadiene (Fig. ); as detailed in the introduction, both studies use the distortion/interaction model to explain reactivity. Predictions were made using geometries that were taken from these two studies after optimising them with AM1 and DFT (see the methodology section outlined above for the full computational procedure). Model performance on ds2 was strongest using SVR thus we utilised this model for our external test set predictions (Table ). The dienes used in the external test sets were part of ds2 therefore, diene distortion was not predicted to avoid a trained model predicting on a previously seen datapoint. Furthermore, any dienophiles that were present in ds2 were removed from the external test sets.