期刊
JOURNAL OF CHEMINFORMATICS
卷 11, 期 1, 页码 -出版社
BMC
DOI: 10.1186/s13321-019-0381-4
关键词
Computational chemistry; Density functional theory; Hydrogen bond strength; Free energy prediction; Cheminformatics
类别
资金
- Bayer AG
- ETH Zurich
We present machine learning (ML) models for hydrogen bond acceptor (HBA) and hydrogen bond donor (HBD) strengths. Quantum chemical (QC) free energies in solution for 1:1 hydrogen-bonded complex formation to the reference molecules 4-fluorophenol and acetone serve as our target values. Our acceptor and donor databases are the largest on record with 4426 and 1036 data points, respectively. After scanning over radial atomic descriptors and ML methods, our final trained HBA and HBD ML models achieve RMSEs of 3.8 kJ mol(-1) (acceptors), and 2.3 kJ mol(-1) (donors) on experimental test sets, respectively. This performance is comparable with previous models that are trained on experimental hydrogen bonding free energies, indicating that molecular QC data can serve as substitute for experiment. The potential ramifications thereof could lead to a full replacement of wetlab chemistry for HBA/HBD strength determination by QC. As a possible chemical application of our ML models, we highlight our predicted HBA and HBD strengths as possible descriptors in two case studies on trends in intramolecular hydrogen bonding.
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