dc.contributorUniversidade Federal de Santa Catarina (UFSC)
dc.contributorUniversity of California
dc.contributorUniversidade Estadual de Campinas (UNICAMP)
dc.contributorUniversidade Estadual Paulista (Unesp)
dc.date.accessioned2014-05-27T11:24:02Z
dc.date.accessioned2022-10-05T18:18:04Z
dc.date.available2014-05-27T11:24:02Z
dc.date.available2022-10-05T18:18:04Z
dc.date.created2014-05-27T11:24:02Z
dc.date.issued2009-11-06
dc.identifierJournal of Organic Chemistry, v. 74, n. 21, p. 8254-8260, 2009.
dc.identifier0022-3263
dc.identifierhttp://hdl.handle.net/11449/71233
dc.identifier10.1021/jo9017638
dc.identifier2-s2.0-70350728453
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/3920435
dc.description.abstract(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.
dc.languageeng
dc.relationJournal of Organic Chemistry
dc.relation4.805
dc.relation1,846
dc.rightsAcesso restrito
dc.sourceScopus
dc.subjectAromatic carbon
dc.subjectCetyltrimethylammonium bromide
dc.subjectDephosphorylations
dc.subjectDinitrophenols
dc.subjectDinitrophenyl
dc.subjectDodecyltrimethylammonium bromides
dc.subjectHydroxamate
dc.subjectHydroxamic acids
dc.subjectMixed micelles
dc.subjectMole fraction
dc.subjectNucleophilic attack
dc.subjectpH range
dc.subjectReactive species
dc.subjectSpontaneous hydrolysis
dc.subjectAmmonium compounds
dc.subjectDyes
dc.subjectMicelles
dc.subjectOrganic acids
dc.subjectPhenols
dc.subjectPhosphorus
dc.subjectCationic surfactants
dc.subject2,4 dinitrophenol
dc.subjectcarbon
dc.subjectcationic surfactant
dc.subjectcetrimide
dc.subjectdecylamine
dc.subjectdodecyltrimethylammonium bromide
dc.subjecthydroxamic acid derivative
dc.subjectisocyanic acid derivative
dc.subjectnucleophile
dc.subjectphosphate
dc.subjectphosphorus
dc.subjecturea derivative
dc.subjectconcentration (parameters)
dc.subjectdephosphorylation
dc.subjectelectrospray mass spectrometry
dc.subjecthydrolysis
dc.subjectionization
dc.subjectkinetics
dc.subjectmass spectrometry
dc.subjectmicelle
dc.subjectmicellization
dc.subjectpH
dc.subjectspecies
dc.subjectCations
dc.subjectHydroxamic Acids
dc.subjectKinetics
dc.subjectMagnetic Resonance Spectroscopy
dc.subjectPhosphoric Acid Esters
dc.subjectPhosphorylation
dc.subjectPotentiometry
dc.subjectSpectrometry, Mass, Electrospray Ionization
dc.subjectSurface-Active Agents
dc.titleThe mechanism of dephosphorylation of bis(2,4-dinitrophenyl) phosphate in mixed micelles of cationic surfactants and lauryl hydroxamic acid
dc.typeArtigo


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