Work

Estimation of multicomponent reactions’ yields from networks of mechanistic steps

Year: 2024

Type: article

Abstract: This work describes estimation of yields of complex, multicomponent reactions (MCRs) based on the modeled networks of mechanistic steps spanning both the main reaction pathway as well as immediate and downstream side reactions. Because experimental values of the kinetic rate constants for individual mechanistic transforms are extremely sparse, these constants are approximated here using Mayr’s nucleophilicity and electrophilicity parameters fine-tuned by correction terms grounded in linear free-energy relationships. With this formalism, the model trained on the mechanistic networks of only 20 – but mechanistically- and yield-diverse MCRs – transfers well to newly discovered MCRs that are based on markedly different mechanisms and types of individual mechanistic transforms. These results suggest that mechanistic-level approach to yield estimation may be a useful alternative to models that are derived from full-reaction data and lack information about yield-lowering side reactions. The ability to predict the yields of organic reactions is of tremendous value for synthetic chemistry, limiting the number of unproductive experiments. Here, the authors describe estimation of yields of complex, multicomponent reactions (MCRs) based on the modeled networks of mechanistic steps spanning both the main reaction pathway as well as immediate and downstream side reactions.

Source: Nature Communications

DOI: 10.1038/s41467-024-54550-1

Authors: Sara Szymkuć, Agnieszka Wołos, Rafał Roszak, Bartosz A. Grzybowski

Institutions: Institute of Organic Chemistry, Polish Academy of Sciences, Institute for Basic Science, Ulsan National Institute of Science and Technology

Language: English

Topic: Chemical Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,790

Funder: Institute for Basic Science