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

doi:10.6023/cjoc202003012

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1563-1570.DOI: 10.6023/cjoc202003012 Previous Articles Next Articles

无酸条件下磷氰酸钠与胺反应合成磷代脲机理的密度泛函理论研究

李志锋^a, 王文鹏^b, 王喜存^b, 权正军^b

a 天水师范学院化学工程与技术学院甘肃天水 741001;
b 西北师范大学化学化工学院兰州 730070

收稿日期:2020-03-05 修回日期:2020-05-17 发布日期:2020-06-01
通讯作者: 权正军 E-mail:quanzhengjun@hotmail.com
基金资助:
国家自然科学基金（Nos.21463023，21562036）和甘肃省自然科学基金（No.17JR5RE010）资助项目.

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

Li Zhifeng^a, Wang Wenpeng^b, Wang Xicun^b, Quan Zhengjun^b

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:2020-03-05 Revised:2020-05-17 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.

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无酸条件下磷氰酸钠与胺反应合成磷代脲机理的密度泛函理论研究

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

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