Suicide nucleophilic attack: Reactions of benzohydroxamate anion with bis(2,4-dinitrophenyl) phosphate

(Chemical Equation Presented) The reaction between the benzohydroxamate anion (BHO-) and bis(2,4-dinitrophenyl)phosphate (BDNPP) has been examined kinetically, and the products were characterized by mass and NMR spectroscopy. The nucleophilic attack of BHO- follows two reaction paths: (i) at phosphorus, giving an unstable intermediate that undergoes a Lossen rearrangement to phenyl isocyanate, aniline, diphenylurea, and O-phenylcarbamyl benzohydroxamate; and (ii) on the aromatic carbon, giving an intermediate that was detected but slowly decomposes to aniline and 2,4-dinitrophenol. Thus, the benzohydroxamate anion can be considered a self-destructive molecular scissor since it reacts and loses its nucleophilic ability. © 2009 American Chemical Society.

Keywords

Aromatic carbon, Chemical equations, Dinitrophenol, Dinitrophenyl, Diphenylurea, Molecular scissor, NMR spectroscopy, Nucleophilic attack, Phenyl isocyanates, Reaction paths, Aniline, Chemical reactions, Nuclear magnetic resonance spectroscopy, Phenols, Phosphorus, Urea, Negative ions, 2 phenylcarbamylbenzohydroxamate, 2,4 dinitrophenol, aniline, benzohydroxamic acid, bis(2,4 dinitrophenyl)phosphate, diphenylurea, nucleophile, phenyl isocyanate, phosphorus, unclassified drug, urea derivative, chemical reaction kinetics, decomposition, lossen rearrangement reaction, mass spectrometry, molecular stability, nonhuman, nuclear magnetic resonance spectroscopy, 2,4-Dinitrophenol, Anions, Benzene, Hydroxamic Acids, Kinetics, Magnetic Resonance Spectroscopy, Molecular Structure, Phosphates