Phosphoric–carboxylic imides. Part 4. MNDO molecular orbital calculations on N-formylphosphinamide, H2P(O)NHCHO, and related systems

Abstract

MNDO molecular orbital calculations were carried out on the mixed imide H₂P(O)NHC(O)H (1), its conjugate base H₂P(O)NC(O)H^–(1a), and the product of its rearrangement, H₂P(O)OC(NH)H (2), using optimised geometries. The molecular parameters obtained for (1) are in good agreement with those determined for two mixed phosphoric–carboxylic imides by X-ray diffraction. Comparison of (1) and (1a) shows that deprotonation affects mainly the NC(O) fragment. Calculations show that (1) should be more stable than the isomer (2), and that their interconversion should be of a concerted nature.