The Evolution of Data-Driven Modeling in Organic Chemistry

Organic chemistry is replete with complex relationships: for example, how a reactant’s structure relates to the resulting product formed; how reaction conditions relate to yield; how a catalyst’s structure relates to enantioselectivity. Questions like these are at the foundation of understanding reactivity and developing novel and improved reactions. An approach to probing these questions that is both longstanding and contemporary is data-driven modeling. Here, we provide a synopsis of the history of data-driven modeling in organic chemistry and the terms used to describe these endeavors. We include a timeline of the steps that led to its current state. The case studies included highlight how, as a community, we have advanced physical organic chemistry tools with the aid of computers and data to augment the intuition of expert chemists and to facilitate the prediction of structure–activity and structure–property relationships.