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Machine learned prediction of reaction template applicability for data-driven retrosynthetic predictions of energetic materials
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Description
Accepted version
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404.65 KB
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Adobe PDF
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57568ca3e9fe40dacb0cde404bb949dd
Author(s) • • •
Fortunato, ME
Coley, CW
Barnes, BC
Jensen, KF
Date Issued
2020
Journal
AIP Conference Proceedings
Publisher
AIP Publishing
Citation
Fortunato, ME, Coley, CW, Barnes, BC and Jensen, KF. 2020. "Machine learned prediction of reaction template applicability for data-driven retrosynthetic predictions of energetic materials." AIP Conference Proceedings, 2272.
Version
Author's final manuscript
Abstract
State of the art computer-aided synthesis planning models are naturally biased toward commonly reported chemical reactions, thus reducing the usefulness of those models for the unusual chemistry relevant to shock physics. To address this problem, a neural network was trained to recognize reaction template applicability for small organic molecules to supplement the rare reaction examples of relevance to energetic materials. The training data for the neural network was generated by brute force determination of template subgraph matching for product molecules from a database of reactions in U.S. patent literature. This data generation strategy successfully augmented the information about template applicability for rare reaction mechanisms in the reaction database. The increased ability to recognize rare reaction templates was demonstrated for reaction templates of interest for energetic material synthesis such as heterocycle ring formation.
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
10.1063/12.0000850