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Research Articles

Iminophosphoranes: Synthesis, evolution of synthesis by 31P-NMR, DFT calculations and antioxidant activity

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Pages 1238-1247 | Received 17 Feb 2022, Accepted 30 May 2022, Published online: 13 Jun 2022
 

Abstract

New mono-iminophosphoranes and new bis-iminophosphoranes 3 were prepared by reaction of triphenylphosphine or tri-alkyl phosphite and azides 1. In order to reduce the reaction time and detect the phosphazides intermediates 2, the reactions of synthesis of iminophosphoranes 3 were evaluated by 31P-NMR spectroscopy. Two phosphazides intermediates 2 in the Z/E form were detected. Density Functional Theory (DFT) calculations were performed at B3LYP/6-311++G** and M062X/def2TZVP to determine the relative stability of Z/E intermediates. Antioxidant activities of iminophosphoranes 3 were evaluated by a 1,1-diphenyl-2-picryl hydrazyl (DPPH) test. The compounds were characterized on the basis of IR, NMR spectroscopy (1H, 13C and 31P) and by HRMS.

GRAPHICAL ABSTRACT

Acknowledgments

We thank Pr. Bayoudh Chaari O. and Pr. Belhaj A. (Faculty of sciences of Tunis) for English language editing.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported financially by the general directorate of scientific research, Tunisian ministry of high education and scientific research.

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