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A molecular electron density theory investigation of the molecular mechanism, regioselectivity, stereoselectivity and chemoselectivity of cycloaddition reaction between acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole

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Abstract

The cycloaddition reactions (32CA) of acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole 1 have been examined employing the molecular electron density theory through DFT calculations at the B3LYP/6-31G ++(d,p) computational level. Investigation of the relative energies related to the competitive ortho and meta reaction paths demonstrates a high chemo-, stereo- and regioselectivity for this 32CA reaction in clear conformity with the experimental results. The topological study of the electron localisation function of the certain points of the IRC associated with the construction of the As–C and C–O single bonds shows a zwitterionic-type structure. The 32CA reaction takes place via a two-stage one-step mechanism initialised with the formation of the As–C single bond.

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Authors and Affiliations

  1. Molecular Modeling and Spectroscopy Research Team, Faculty of Science, Chouaïb Doukkali University, P.O. Box 20, 24000, El Jadida, Morocco

    Abdellah Zeroual, Mohammed El Idrissi, Ouled Aitouna Anas, Mohammed Salah & Habib El Alaoui El Abdallaoui

  2. Department of Organic Chemistry, University of Valencia, Dr. Moliner 50, 46100, Burjassot, Valencia, Spain

    Mar Ríos-Gutiérrez & Luis Ramon Domingo

  3. Laboratory of Organic and Analytical Chemistry, Faculty of Sciences and Techniques, Sultan Moulay Slimane University, B. P. 523, Beni-Mellal, Morocco

    Mohamed El Ghozlani

  4. Department of Chemistry, Polydisciplinary Faculty, Sultan Moulay Slimane University, Beni-Mellal, Morocco

    Mohammed El Idrissi

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  1. Abdellah Zeroual
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  2. Mar Ríos-Gutiérrez
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  3. Mohamed El Ghozlani
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  4. Mohammed El Idrissi
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  6. Mohammed Salah
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  7. Habib El Alaoui El Abdallaoui
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  8. Luis Ramon Domingo
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Correspondence to Abdellah Zeroual.

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Zeroual, A., Ríos-Gutiérrez, M., El Ghozlani, M. et al. A molecular electron density theory investigation of the molecular mechanism, regioselectivity, stereoselectivity and chemoselectivity of cycloaddition reaction between acetonitrile N-oxide and 2,5-dimethyl-2H-[1,2,3]diazarsole. Theor Chem Acc 139, 37 (2020). https://doi.org/10.1007/s00214-020-2547-6

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