Reactivity of Phosphonothioamidates with Acid Chlorides and Primary Amines: Synthesis and Conformational Study of N-Acylated Phosphonothioamidates and Phosphonoamidines

GRAPHICAL ABSTRACT

Abstract

Various N-acyl phosphonothioamidate derivatives, 2, were obtained from N-acylation of phosphonothioamidates, 1, with different acid chlorides. Phosphonoamidines, 3, were prepared in high yields by reacting phosphonothioamidates, 1, with primary amines at room temperature, to short reaction periods. All compounds were characterized on the basis of IR and NMR spectroscopy (¹H, ¹³C, ¹⁹F, and ³¹P) and in some cases by elemental analysis and calculations using Density Functional Theory (DFT)-B3LYP// 3-21G+** and evolution study by ³¹P-NMR and ¹⁹F-NMR spectroscopy using an external lock with D₂O.

Keywords:

• Phosphonothioamidates
• N-acyl-phosphonothioamidates
• phosphonoamidines
• DFT
• evolution study