Orth, Elisa S.Da Silva, Pedro L. F.Mello, Renata S.Bunton, Clifford A.Milagre, Humberto M. S. [UNESP]Eberlin, Marcos N.Fiedler, Haidi D.Nome, Faruk2014-05-272014-05-272009-07-17Journal of Organic Chemistry, v. 74, n. 14, p. 5011-5016, 2009.0022-3263http://hdl.handle.net/11449/71091(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.5011-5016engAromatic carbonChemical equationsDinitrophenolDinitrophenylDiphenylureaMolecular scissorNMR spectroscopyNucleophilic attackPhenyl isocyanatesReaction pathsAnilineChemical reactionsNuclear magnetic resonance spectroscopyPhenolsPhosphorusUreaNegative ions2 phenylcarbamylbenzohydroxamate2,4 dinitrophenolanilinebenzohydroxamic acidbis(2,4 dinitrophenyl)phosphatediphenylureanucleophilephenyl isocyanatephosphorusunclassified drugurea derivativechemical reaction kineticsdecompositionlossen rearrangement reactionmass spectrometrymolecular stabilitynonhumannuclear magnetic resonance spectroscopy2,4-DinitrophenolAnionsBenzeneHydroxamic AcidsKineticsMagnetic Resonance SpectroscopyMolecular StructurePhosphatesArtigo10.1021/jo9007354Acesso restrito2-s2.0-67650413660