The electronic effects of substituents onⁿJ_PX(n = 2, 3; X = H, C) coupling constants and phosphorus chemical shifts; syntheses and spectroscopic investigation of some phosphoramidates

Abstract

New phosphoramidates with the general formulae Me 2 NP(O)Cl(p-NHC 6 H 4 -R) (A) and Me 2 NP(O)(p-NHC 6 H 4 -R) 2 (B), where R = H, CH 3 and NO 2 , F, Cl, Br, I, were synthesized and characterized by 1 H, 13 C, 31 P NMR and IR spectroscopy and elemental analysis. The electronic effects of donor, acceptor and neutral groups on n J PX coupling constants (n = 2, 3; X = H, C) and phosphorus chemical shifts are discussed. NMR data show that only the 4-nitroaniline substituent resulted in the disappearance of all coupling ( n J PX = 0.0 Hz). Two nearly linear correlations were obtained between para-substituent constants (s p ) and phosphorus chemical shifts for the two series A and B.

Phosphoramidates: Molecular Packing and Hydrogen Bond Strength in Compounds Having a P(O)(N)n(O)3-n (n = 1, 2, 3) Skeleton

“…Another strategy for preparation of phosphoramidate compounds is the application of sodium amide salts which produces sodium halide as a by-product [82] (Scheme 4).…”