A Dataset of Computational Reaction Barriers for the Claisen Rearrangement: Chemical and Numerical Analysis

Hiroaki Okada; Satoshi Maeda

doi:10.1002/minf.202100216

A Dataset of Computational Reaction Barriers for the Claisen Rearrangement: Chemical and Numerical Analysis

Mol Inform. 2022 Mar;41(3):e2100216. doi: 10.1002/minf.202100216. Epub 2021 Oct 18.

Authors

Hiroaki Okada¹, Satoshi Maeda^{2

3

4

5}

Affiliations

¹ Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
² Department of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
³ Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Hokkaido 001-0021, Japan.
⁴ ERATO Maeda Artificial Intelligence for Chemical Reaction Design and Discovery Project, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
⁵ Research and Services Division of Materials Data and Integrated System (MaDIS), National Institute for Materials Science (NIMS), Tsukuba, Ibaraki 305-0044, Japan.

PMID: 34661976
DOI: 10.1002/minf.202100216

Abstract

Theoretical reaction screening based on Gibbs energy barriers would be promising to accelerate chemical reactions mining. The number of quantum chemical calculations can be reduced by using an optimization algorithm such as genetic algorithm (GA) and Bayesian optimization (BO). The focus of this study is to generate a dataset of reaction barriers of size ∼100000. Such a dataset would be useful to quickly evaluate various implementations of an optimization algorithm such as GA and BO. The dataset includes Gibbs energy barriers of the Claisen rearrangement for ∼100000 molecules computed on the basis of a semiempirical theory PM7. After evaluating its chemical and numerical features, it is found that the dataset well reflects chemical trends of various substitutions and is useful in testing various implementations of an optimization algorithm. The dataset is available in the supplementary material of this paper.

Keywords: Claisen rearrangement; Genetic algorithm; Quantum chemical calculation; Reaction barrier dataset; Transition state.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bayes Theorem*