Acid-Promoted Hydrolysis of m-Cl-Phenyl Phosphorotriamidate leading to its Highly Basic Nature by Kinetic Means

Hydrolysis of m-Cl-Phenyl Phosphorotriamidate has been performed in the acid range, 0.01to 7.0M –HCl,in 12%AcoH-H2O (v/v) at 98(±0.5) oC. The continuous second-order rate rise with the absence of a rate maximum in the entire acid range is significant, leading to its highly basic nature. In this respect, it differs from other related(o-Cl-Ph-&p-Cl-Ph-) members of the phosphorotriamidate group. The salt effect variable study leads to the presence and reactivity of the two major reactive species with the Neutral Species(I) working in the entire acid range; while the Conjugate acid form(II) was observed operating between 4.0-7.0M HCl region only. Both uni-and bi-molecular mechanisms for the two reactive forms with P-N bond fission have been decided for the C-N-P ester. The hydrolysis is shown to be decreased by the action of the series of the nucleophilic reagents and I’shows the optimum effect here. Role of a chloro-group in the unusual meta position in each aryl matix during hydrolysis was particularly the important feature of this study.