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Comparative study on the methods for predicting the reactive site of nucleophilic reaction

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Abstract

Predicting the reactivity of nucleophilic reaction at different sites has important theoretical and practical significance. Many prediction methods solely based on the electronic structure of reactants have been proposed. In this paper, detailed comparative analyses on the reliability of 14 methods are carried out and three series of molecules, carbonyl compounds, aromatic hydrocarbons and pyridine derivatives are exploited as test systems. It is found that the methods reflecting local electronic softness, such as condensed dual descriptor, have satisfactory prediction ability; while the ones reflecting electrostatic effect, such as atomic charge analysis and electrostatic potential analysis, have evidently worse overall performance. For all systems of interest, condensed dual descriptor and Hirshfeld charge display the most robust predictive capacity.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, School of Chemical and Biological Engineering, University of Science and Technology Beijing, Beijing, 100083, China

    Jingsi Cao, Qing Ren & Feiwu Chen

  2. Beijing Kein Research Center for Natural Sciences, Beijing, 100022, China

    Tian Lu

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  1. Jingsi Cao
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  2. Qing Ren
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  3. Feiwu Chen
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  4. Tian Lu
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Correspondence to Feiwu Chen.

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Dedicated to Professor Lemin Li on the occasion of his 80th birthday.

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Cao, J., Ren, Q., Chen, F. et al. Comparative study on the methods for predicting the reactive site of nucleophilic reaction. Sci. China Chem. 58, 1845–1852 (2015). https://doi.org/10.1007/s11426-015-5494-7

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  • DOI: https://doi.org/10.1007/s11426-015-5494-7

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