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The influence of Lewis acid catalyst on the kinetic and molecular mechanism of nitrous acid elimination from 5-nitro-3-phenyl-4,5-dihydroisoxazole: DFT computational study

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Chemistry of Heterocyclic Compounds Aims and scope

The molecular mechanism of nitrous acid elimination from 5-nitro-3-phenyl-4,5-dihydroisoxazole systems has been explored using DFT computational study. It was found that under both catalytic and non-catalytic conditions, these processes proceed according to a one-step asynchronous mechanism. The asynchronicity of transition state is determined by presence of Lewis acid catalyst. However, it is not enough to force an ionic mechanism. The proposed pattern can be considered as a general mechanism for this group of heterocyclic compounds.

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All calculations reported in this manuscript were performed on Prometheus cluster in the CYFRONET regional computational center in Cracow.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Technology, Cracow University of Technology, 24 Warszawska St., 31-155, Cracow, Poland

    Agnieszka Łapczuk-Krygier, Jolanta Jaśkowska & Radomir Jasiński

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  1. Agnieszka Łapczuk-Krygier
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  2. Jolanta Jaśkowska
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  3. Radomir Jasiński
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Correspondence to Radomir Jasiński.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(12), 1172–1174

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Łapczuk-Krygier, A., Jaśkowska, J. & Jasiński, R. The influence of Lewis acid catalyst on the kinetic and molecular mechanism of nitrous acid elimination from 5-nitro-3-phenyl-4,5-dihydroisoxazole: DFT computational study. Chem Heterocycl Comp 54, 1172–1174 (2018). https://doi.org/10.1007/s10593-019-02410-y

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  • DOI: https://doi.org/10.1007/s10593-019-02410-y

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