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Mechanism of Formation of N-Methyl-N-[2-(diphenylphosphoryl)-ethyl]amide of (Diphenylphosphoryl)acetic Acid

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Abstract

The mechanism of formation of N-methyl-2-(diphenylphosphoryl)acetamide was studied by DFT. The first stage, the reaction of trichlorophosphine with 2-(diphenylphosphoryl)acetic acid, involves three elementary steps, and the explicit inclusion of solvent makes it possible to reduce the activation energy of each of them. The second stage, the reaction of 2-(diphenylphosphoryl)acetyl chloride with a phosphoryl-substituted amine, involves one elementary step.

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ACKNOWLEDGMENTS

The calculations were performed at the Joint Supercomputer Center of the Russian Academy of Sciences (https://www.jscc.ru/).

Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 20-03-00119).

Author information

Authors and Affiliations

  1. Kazan Federal University, 420008, Kazan, Russia

    A. A. Kuznetsova & Ya. A. Vereshchagina

  2. Kazan Department of Joint Supercomputer Center of the Russian Academy of Sciences, Branch of the “Scientific Research Institute for System Analysis of the Russian Academy of Sciences” Federal State Institution, 420111, Kazan, Russia

    D. V. Chachkov

  3. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991, Moscow, Russia

    O. I. Artyushin

  4. Institute of Chemical Reagents and High Purity Chemical Substances, “Kurchatov Institute” National Research Center, 107076, Moscow, Russia

    N. A. Bondarenko

  5. “Kurchatov Institute” National Research Center, 123182, Moscow, Russia

    N. A. Bondarenko

Authors
  1. A. A. Kuznetsova
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  2. D. V. Chachkov
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  3. O. I. Artyushin
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  4. N. A. Bondarenko
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  5. Ya. A. Vereshchagina
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Corresponding author

Correspondence to Ya. A. Vereshchagina.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 2, pp. 211–216 https://doi.org/10.31857/S0514749223020064.

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Kuznetsova, A.A., Chachkov, D.V., Artyushin, O.I. et al. Mechanism of Formation of N-Methyl-N-[2-(diphenylphosphoryl)-ethyl]amide of (Diphenylphosphoryl)acetic Acid. Russ J Org Chem 59, 265–269 (2023). https://doi.org/10.1134/S1070428023020069

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