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|Type:||Artigo de periódico|
|Title:||Suicide Nucleophilic Attack: Reactions of Benzohydroxamate Anion with Bis(2,4-dinitrophenyl) Phosphate|
da Silva, PLF
|Abstract:||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 phosphor-us, 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.|
|Editor:||Amer Chemical Soc|
|Appears in Collections:||Artigos e Materiais de Revistas Científicas - Unicamp|
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