Kinetic Stability of A Phosphoric Mono-Substituted Aryl Amide in an Acid Range

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Phosphoric mono-o-methoxyphenyl amide (DCHA salt), a C-N-P ester hydrolyses biomolecularly in acid (0.01-7.0 M HCl) at 40 (± 0.5)°C, with P-N bond cleavage, leading to the active role of Zwitterionic, neutral and the conjugate acid (>2.0 M) species. The presence of o-MeO substituent increases the range of participation of the sole conjugate acid form, beyond 2.0M HCl. A rigid and compact T.S. is decided in terms of DS#, while its polar nature is supported by solvent polarity changes. Phosphorylation of the parent amine (with CTAB catalyst) with POCl3 led to the formation of the C-N-P ester (31p studies) under observation.

Phosphoric amide; C-N-P ester; Hydrolysis; Kinetic stability