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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1563 - 1570

DOI: https://doi.org/10.6023/cjoc202003012

Mechanism of Synthesis of Phosphinecarboxamides by Reaction of Sodium Phosphaethynolate Anion and Amines under Acid-Free Conditions: Density Functional Theory Investigation

  • Li Zhifeng ,
  • Wang Wenpeng ,
  • Wang Xicun ,
  • Quan Zhengjun
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  • a College of Chemical Engineering and Technology, Tianshui Normal University, Tianshui, Gansu 741001;
    b College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received date: 2020-03-05

  Revised date: 2020-05-17

  Online published: 2020-06-01

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21463023, 21562036) and the Natural Science Foundation of Gansu Province (No. 17JR5RE010).

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Abstract

The reaction of 2-phosphaethynolate anion and primary amines for phosphinecarboxamides synthesis using mechanochemistry has been studied using IR, 13C NMR and 31P NMR spectra, and the reaction occurred under grinding, mild and acid-free conditions at room temperature. In this paper, a comprehensive mechanistic density functional theory (DFT) of B3LYP/6-31G(d,p) study reveals that H shift can be aided/catalyzed with solvents and further the activation free energies barrier can be dramatically decreased, which is responsible for the higher yield of the product in the experiment.

Key words： 2-phosphaethynolate anion; phosphinecarboxamide; reaction mechanism; DFT

Cite this article

Li Zhifeng , Wang Wenpeng , Wang Xicun , Quan Zhengjun . Mechanism of Synthesis of Phosphinecarboxamides by Reaction of Sodium Phosphaethynolate Anion and Amines under Acid-Free Conditions: Density Functional Theory Investigation[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1563 -1570 . DOI: 10.6023/cjoc202003012

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