Impact of noise on inverse design: the case of NMR spectra matching

Author(s)
Dominik Lemm, Guido Falk von Rudorff, O. Anatole von Lilienfeld
Abstract

Despite its fundamental importance and widespread use for assessing reaction success in organic chemistry, deducing chemical structures from nuclear magnetic resonance (NMR) measurements has remained largely manual and time consuming. To keep up with the accelerated pace of automated synthesis in self driving laboratory settings, robust computational algorithms are needed to rapidly perform structure elucidations. We analyse the effectiveness of solving the NMR spectra matching task encountered in this inverse structure elucidation problem by systematically constraining the chemical search space, and correspondingly reducing the ambiguity of the matching task. Numerical evidence collected for the twenty most common stoichiometries in the QM9-NMR database indicate systematic trends of more permissible machine learning prediction errors in constrained search spaces. Results suggest that compounds with multiple heteroatoms are harder to characterize than others. Extending QM9 by ∼10 times more constitutional isomers with 3D structures generated by Surge, ETKDG and CREST, we used ML models of chemical shifts trained on the QM9-NMR data to test the spectra matching algorithms. Combining both 13C and 1H shifts in the matching process suggests twice as permissible machine learning prediction errors than for matching based on 13C shifts alone. Performance curves demonstrate that reducing ambiguity and search space can decrease machine learning training data needs by orders of magnitude.

Organisation(s)
Computational Materials Physics
External organisation(s)
Universität Kassel, University of Toronto, Vector Institute for Artificial Intelligence, Technische Universität Berlin
Journal
Digital Discovery
Volume
3
Pages
136-144
No. of pages
9
ISSN
2635-098X
DOI
https://doi.org/10.48550/arXiv.2307.03969
Publication date
10-2023
Peer reviewed
Yes
Austrian Fields of Science 2012
103006 Chemical physics
ASJC Scopus subject areas
Chemistry (miscellaneous)
Portal url
https://ucrisportal.univie.ac.at/en/publications/fbd5e7cc-c7c1-4d12-b859-ee4cf0d60677