ArticleChemical science2018
Fast and accurate prediction of the regioselectivity of electrophilic aromatic substitution reactions.
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 80 citations in OpenAlex.
- Deprotonative Single-Electron Oxidation as a General and Controllably Selective Platform for Benzylic C-H Functionalization.Journal of the American Chemical Society · 2026Article
- Rega: A Platform for the Prediction of the Regioselectivity of C-H Functionalization Reactions.Journal of chemical information and modeling · 2026Article
- Predicting the Stability of Base-mediated C─H Carboxylation Adducts Using Data Science Tools.Angewandte Chemie (International ed. in English) · 2026Article
- A database of steric and electronic properties of heteroaryl substituents.Scientific data · 2025Article
- Computational tools for the prediction of site- and regioselectivity of organic reactions.Chemical science · 2025Review
- Enhancing chemical synthesis planning: automated quantum mechanics-based regioselectivity prediction for C-H activation with directing groups.Beilstein journal of organic chemistry · 2025Article
- meta-Selective C-H arylation of phenols via regiodiversion of electrophilic aromatic substitution.Nature chemistry · 2023Article
- Analysis of Laboratory-Evolved Flavin-Dependent Halogenases Affords a Computational Model for Predicting Halogenase Site Selectivity.Chem catalysis · 2022Article
- Mini-Review on Structure-Reactivity Relationship for Aromatic Molecules: Recent Advances.ACS omega · 2022Review
- Machine Learning Applied to the Modeling of Pharmacological and ADMET Endpoints.Methods in molecular biology (Clifton, N.J.) · 2022Review
- High Site Selectivity in Electrophilic Aromatic Substitutions: Mechanism of C-H Thianthrenation.Journal of the American Chemical Society · 2021Article
- Real-time prediction ofChemical science · 2021Article
- Teaching a neural network to attach and detach electrons from molecules.Nature communications · 2021Article
- Precise equilibrium structure of thiazole (c-CThe Journal of chemical physics · 2021Article
- Selectivity in the Elaboration of Bicyclic Borazarenes.Advanced synthesis & catalysis · 2021Article
- Organic reactivity from mechanism to machine learning.Nature reviews. Chemistry · 2021Review
- RegioSQM20: improved prediction of the regioselectivity of electrophilic aromatic substitutions.Journal of cheminformatics · 2021Article
- Energetics of Electron Pairs in Electrophilic Aromatic Substitutions.Molecules (Basel, Switzerland) · 2021Article
- Computational generation of an annotated gigalibrary of synthesizable, composite peptidic macrocycles.Proceedings of the National Academy of Sciences of the United States of America · 2020Article
- Molecular Transformer: A Model for Uncertainty-Calibrated Chemical Reaction Prediction.ACS central science · 2019Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
While computational prediction of chemical reactivity is possible it usually requires expert knowledge and there are relatively few computational tools that can be used by a bench chemist to help guide synthesis. The RegioSQM method for predicting the regioselectivity of electrophilic aromatic substitution reactions of heteroaromatic systems is presented in this paper. RegioSQM protonates all aromatic C-H carbon atoms and identifies those with the lowest free energies in chloroform using the PM3 semiempirical method as the most nucleophilic center. These positions are found to correlate qualitatively with the regiochemical outcome in a retrospective analysis of 96% of more than 525 literature examples of electrophilic aromatic halogenation reactions. The method is automated and requires only a SMILES string of the molecule of interest, which can easily be generated using chemical drawing programs such as ChemDraw. The computational cost is 1-10 minutes per molecule depending on size, using relatively modest computational resources and the method is freely available
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.