An Attempt to Classify Elementary Reactions on the Basis of TS Motifs

TL;DR

This paper explores classifying organic chemistry reactions based on transition state motifs using a self-organizing map.

Contribution

A novel approach to classify elementary reactions using TS motif descriptors and Kohonen self-organization maps.

Findings

102 elementary reactions were successfully clustered based on their TS motifs.

A Kohonen map trained with 13 TS descriptors effectively classified the reactions.

The method allows identifying reactions with similar TS motifs efficiently.

Abstract

Reactions commonly used in synthetic organic chemistry are named after their discoverers or developers. They are called the name reactions and generally consist of several elementary reactions. Quantum chemical calculations can optimize transition state (TS) structures of the elementary reactions. The geometrical feature of TS is called TS motif. We have constructed a database (QMRDB) with the TS motif information and have been continuing to accumulate them. In the present study, we extracted 102 elementary reactions from the QMRDB and attempted to classify them using the Kohonen self‐organization map. As the results, all the TS motifs were clustered. By firing a target compound on a Kohonen map generated, we expect to be able to easily find the TS motifs most similar to the target.

The geometric characteristics of the TS structure are called TS motifs. In this study, we calculated 13 descriptors from the TS motifs and created Kohonen maps trained with these descriptors. As a result, we found that the obtained map could classify 102 elementary reactions.

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