Prediction of Homolytic Bond Dissociation Enthalpies for Organic Molecules at near Chemical Accuracy with Sub-Second Computational Cost

15 November 2019, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Bond dissociation enthalpies (BDEs) of organic molecules play a fundamental role in determining chemical reactivity. However, BDE computations at sufficiently high levels of quantum mechanical (QM) theory require substantial computing resources. We have therefore developed A machine-Learning derived, Fast, Accurate Bond dissociation Enthalpy Tool (ALFABET), capable of accurately predicting BDEs for organic molecules in a fraction of a second. Automated density functional theory (DFT) calculations at the M06-2X/def2-TZVP level of theory were performed for 42,577 small organic molecules, resulting in a dataset of 290,664 BDEs. A graph neural network was trained on a subset of these results, achieving a mean absolute error of 0.58 kcal/mol for the BDE values of unseen molecules. An interface for the developed prediction tool is available online at https://ml.nrel.gov/bde. The model rapidly and accurately predicts major sites of hydrogen abstraction in metabolism of drug-like molecules and determines the dominant molecular fragmentation pathways during soot formation.

Keywords

machine learning
Bond Dissociation Enthalpies
radicals

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