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Type: Artigo de periódico
Title: The Mechanism of Dephosphorylation of Bis(2,4-dinitrophenyl) Phosphate in Mixed Micelles of Cationic Surfactants and Lauryl Hydroxamic Acid
Author: Silva, M
Mello, RS
Farrukh, MA
Venturini, J
Bunton, CA
Milagre, HMS
Eberlin, MN
Fiedler, HD
Nome, F
Abstract: Mixed micelles of cetyltrimethylammonum bromide (CTABr) or dodecyltrimethylammonium bromide (DTABr) and the alpha-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
Country: EUA
Editor: Amer Chemical Soc
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 74, n. 21, n. 8254, n. 8260, 2009.
Rights: fechado
Identifier DOI: 10.1021/jo9017638
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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