Organic reactivity from mechanism to machine learning

As more data are introduced in the building of models of chemical reactivity, the mechanistic component can be reduced until 'big data' applications are reached. These methods no longer depend on underlying mechanistic hypotheses, potentially learning them implicitly through extensive data training. Reactivity models often focus on reaction barribers, but can also be trained to directly predict lab-relevant properties, such as yields or conditions. Calculations with a quantum-mechanical component are still preferred for quantitative predictions of reactivity. Although big data applications tend to be more qualitative, they have the advantage to be broadly applied to different kinds of reactions. There is a continuum of methods in between these extremes, such as methods that use quantum-derived data or descriptors in machine learning models. Here, we present an overview of the recent machine learning applications in the field of chemical reactivity from a mechanistic perspective. Starting with a summary of how reactivity questions are addressed by quantum-mechanical methods, we discuss methods that augment or replace quantum-based modelling with faster alternatives relying on machine learning.

Automated summary

The introduction of more data in chemical reactivity models reduces the dependence on mechanistic hypotheses, as 'big data' applications potentially learn them implicitly through data training. These models can predict reaction barriers, lab-relevant properties, and calculations with a quantum-mechanical component are preferred for quantitative predictions of reactivity. Big data applications tend to be more qualitative but can be broadly applied to different kinds of reactions.