dc.contributor | Universidade Federal de Santa Catarina (UFSC) | |
dc.contributor | University of California | |
dc.contributor | Universidade Estadual de Campinas (UNICAMP) | |
dc.contributor | Universidade Estadual Paulista (Unesp) | |
dc.date.accessioned | 2014-05-27T11:24:02Z | |
dc.date.accessioned | 2022-10-05T18:18:04Z | |
dc.date.available | 2014-05-27T11:24:02Z | |
dc.date.available | 2022-10-05T18:18:04Z | |
dc.date.created | 2014-05-27T11:24:02Z | |
dc.date.issued | 2009-11-06 | |
dc.identifier | Journal of Organic Chemistry, v. 74, n. 21, p. 8254-8260, 2009. | |
dc.identifier | 0022-3263 | |
dc.identifier | http://hdl.handle.net/11449/71233 | |
dc.identifier | 10.1021/jo9017638 | |
dc.identifier | 2-s2.0-70350728453 | |
dc.identifier.uri | http://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.language | eng | |
dc.relation | Journal of Organic Chemistry | |
dc.relation | 4.805 | |
dc.relation | 1,846 | |
dc.rights | Acesso restrito | |
dc.source | Scopus | |
dc.subject | Aromatic carbon | |
dc.subject | Cetyltrimethylammonium bromide | |
dc.subject | Dephosphorylations | |
dc.subject | Dinitrophenols | |
dc.subject | Dinitrophenyl | |
dc.subject | Dodecyltrimethylammonium bromides | |
dc.subject | Hydroxamate | |
dc.subject | Hydroxamic acids | |
dc.subject | Mixed micelles | |
dc.subject | Mole fraction | |
dc.subject | Nucleophilic attack | |
dc.subject | pH range | |
dc.subject | Reactive species | |
dc.subject | Spontaneous hydrolysis | |
dc.subject | Ammonium compounds | |
dc.subject | Dyes | |
dc.subject | Micelles | |
dc.subject | Organic acids | |
dc.subject | Phenols | |
dc.subject | Phosphorus | |
dc.subject | Cationic surfactants | |
dc.subject | 2,4 dinitrophenol | |
dc.subject | carbon | |
dc.subject | cationic surfactant | |
dc.subject | cetrimide | |
dc.subject | decylamine | |
dc.subject | dodecyltrimethylammonium bromide | |
dc.subject | hydroxamic acid derivative | |
dc.subject | isocyanic acid derivative | |
dc.subject | nucleophile | |
dc.subject | phosphate | |
dc.subject | phosphorus | |
dc.subject | urea derivative | |
dc.subject | concentration (parameters) | |
dc.subject | dephosphorylation | |
dc.subject | electrospray mass spectrometry | |
dc.subject | hydrolysis | |
dc.subject | ionization | |
dc.subject | kinetics | |
dc.subject | mass spectrometry | |
dc.subject | micelle | |
dc.subject | micellization | |
dc.subject | pH | |
dc.subject | species | |
dc.subject | Cations | |
dc.subject | Hydroxamic Acids | |
dc.subject | Kinetics | |
dc.subject | Magnetic Resonance Spectroscopy | |
dc.subject | Phosphoric Acid Esters | |
dc.subject | Phosphorylation | |
dc.subject | Potentiometry | |
dc.subject | Spectrometry, Mass, Electrospray Ionization | |
dc.subject | Surface-Active Agents | |
dc.title | The mechanism of dephosphorylation of bis(2,4-dinitrophenyl) phosphate in mixed micelles of cationic surfactants and lauryl hydroxamic acid | |
dc.type | Artigo | |