Publicação: Suicide nucleophilic attack: Reactions of benzohydroxamate anion with bis(2,4-dinitrophenyl) phosphate
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(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.
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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
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Journal of Organic Chemistry, v. 74, n. 14, p. 5011-5016, 2009.
