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

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

Keywords:

• Iminophosphoranes
• ³¹P-NMR spectroscopy
• phosphazides intermediates
• DFT calculations
• antioxidant activity

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.