Silva, MarceloMello, Renata S.Farrukh, M. AkhyarVenturini, JanioBunton, Clifford A.Milagre, Humberto M. S. [UNESP]Eberlin, Marcos N.Fiedler, Haidi D.Nome, Faruk2014-05-272014-05-272009-11-06Journal of Organic Chemistry, v. 74, n. 21, p. 8254-8260, 2009.0022-3263http://hdl.handle.net/11449/71233(Figure Presented) Mixed micelles of cetyltrimethylammonium bromide (CTABr) or dodecyltrimethylammonium bromide (DTABr) and the α-nucleophile, lauryl hydroxamic acid (LHA) accelerate dephosphorylation of bis(2,4-dinitrophenyl) phosphate (BDNPP) over the pH range 4-10. With a 0.1 mole fraction of LHA in DTABr or CTABr, dephosphorylation of BDNPP is approximately 10 4-fold faster than its spontaneous hydrolysis, and monoanionic LHA - is the reactive species. The results are consistent with a mechanism involving concurrent nucleophilic attack by hydroxamate ion (i) on the aromatic carbon, giving an intermediate that decomposes to undecylamine and 2,4-dinitrophenol, and (ii) at phosphorus, giving an unstable intermediate that undergoes a Lossen rearrangement yielding a series of derivatives including N,N-dialkylurea, undecylamine, undecyl isocyanate, and carbamyl hydroxamate. © 2009 American Chemical Society.8254-8260engAromatic carbonCetyltrimethylammonium bromideDephosphorylationsDinitrophenolsDinitrophenylDodecyltrimethylammonium bromidesHydroxamateHydroxamic acidsMixed micellesMole fractionNucleophilic attackpH rangeReactive speciesSpontaneous hydrolysisAmmonium compoundsDyesMicellesOrganic acidsPhenolsPhosphorusCationic surfactants2,4 dinitrophenolcarboncationic surfactantcetrimidedecylaminedodecyltrimethylammonium bromidehydroxamic acid derivativeisocyanic acid derivativenucleophilephosphatephosphorusurea derivativeconcentration (parameters)dephosphorylationelectrospray mass spectrometryhydrolysisionizationkineticsmass spectrometrymicellemicellizationpHspeciesCationsHydroxamic AcidsKineticsMagnetic Resonance SpectroscopyPhosphoric Acid EstersPhosphorylationPotentiometrySpectrometry, Mass, Electrospray IonizationSurface-Active AgentsArtigo10.1021/jo9017638Acesso restrito2-s2.0-70350728453