Micellar Synthesis and Acid Hydrolysis of a Phosphoric Diamide

Abstract

Phosphoric bis-(2,4-dimethoxyphenyl amide) chloride, a
C—N—P containing bis-amide, has been kinetically examined (a
rate maximum at 4.0 M) during hydrolysis in 0.01-7.0 M HCl at
40 ±0.5°C. Zwitter ionic-neutral (or protonated-neutral) and conjugate
acid species have been assessed as the major reactive forms,
undergoing bimolecular hydrolysis with P—N bond fission.
Arrhenius parameters and other concepts support bimolecular mode
with 3-4 water molecules involved in the transfer of proton, formation
of transition state and overall hydrolysis. Out of 20, only 3
reaction routes operate during hydrolysis. Synthesis has been performed
using both parent amine as well as POCl₃ in the presence
of meagre amount of CTAB.