Suicide nucleophilic attack: Reactions of benzohydroxamate anion with bis(2,4-dinitrophenyl) phosphate

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dc.contributor.authorOrth, Elisa S.
dc.contributor.authorDa Silva, Pedro L. F.
dc.contributor.authorMello, Renata S.
dc.contributor.authorBunton, Clifford A.
dc.contributor.authorMilagre, Humberto M. S. [UNESP]
dc.contributor.authorEberlin, Marcos N.
dc.contributor.authorFiedler, Haidi D.
dc.contributor.authorNome, Faruk
dc.contributor.institutionUniversidade Federal de Santa Catarina (UFSC)
dc.contributor.institutionUniversity of California
dc.contributor.institutionUniversidade Estadual de Campinas (UNICAMP)
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.date.accessioned2014-05-27T11:23:56Z
dc.date.available2014-05-27T11:23:56Z
dc.date.issued2009-07-17
dc.description.abstract(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.en
dc.description.affiliationDepartamento de Química Universidade Federal de Santa Catarina, 88040-900 Florianópolis, SC
dc.description.affiliationDepartment of Chemistry and Biochemistry University of California, Santa Barbara, CA 93106
dc.description.affiliationThoMSon Mass Spectrometry Laboratory Institute of Chemistry University of Campinas, 13083-970, Campinas, SP
dc.description.affiliationDepartament of Biochemistry and Microbiology São Paulo State University, 13506-900, Rio Claro, SP
dc.description.affiliationUnespDepartament of Biochemistry and Microbiology São Paulo State University, 13506-900, Rio Claro, SP
dc.format.extent5011-5016
dc.identifierhttp://dx.doi.org/10.1021/jo9007354
dc.identifier.citationJournal of Organic Chemistry, v. 74, n. 14, p. 5011-5016, 2009.
dc.identifier.doi10.1021/jo9007354
dc.identifier.issn0022-3263
dc.identifier.scopus2-s2.0-67650413660
dc.identifier.urihttp://hdl.handle.net/11449/71091
dc.language.isoeng
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.ispartofjcr4.805
dc.relation.ispartofsjr1,846
dc.rights.accessRightsAcesso restrito
dc.sourceScopus
dc.subjectAromatic carbon
dc.subjectChemical equations
dc.subjectDinitrophenol
dc.subjectDinitrophenyl
dc.subjectDiphenylurea
dc.subjectMolecular scissor
dc.subjectNMR spectroscopy
dc.subjectNucleophilic attack
dc.subjectPhenyl isocyanates
dc.subjectReaction paths
dc.subjectAniline
dc.subjectChemical reactions
dc.subjectNuclear magnetic resonance spectroscopy
dc.subjectPhenols
dc.subjectPhosphorus
dc.subjectUrea
dc.subjectNegative ions
dc.subject2 phenylcarbamylbenzohydroxamate
dc.subject2,4 dinitrophenol
dc.subjectaniline
dc.subjectbenzohydroxamic acid
dc.subjectbis(2,4 dinitrophenyl)phosphate
dc.subjectdiphenylurea
dc.subjectnucleophile
dc.subjectphenyl isocyanate
dc.subjectphosphorus
dc.subjectunclassified drug
dc.subjecturea derivative
dc.subjectchemical reaction kinetics
dc.subjectdecomposition
dc.subjectlossen rearrangement reaction
dc.subjectmass spectrometry
dc.subjectmolecular stability
dc.subjectnonhuman
dc.subjectnuclear magnetic resonance spectroscopy
dc.subject2,4-Dinitrophenol
dc.subjectAnions
dc.subjectBenzene
dc.subjectHydroxamic Acids
dc.subjectKinetics
dc.subjectMagnetic Resonance Spectroscopy
dc.subjectMolecular Structure
dc.subjectPhosphates
dc.titleSuicide nucleophilic attack: Reactions of benzohydroxamate anion with bis(2,4-dinitrophenyl) phosphateen
dc.typeArtigo
dcterms.licensehttp://pubs.acs.org/paragonplus/copyright/jpa_form_a.pdf
unesp.campusUniversidade Estadual Paulista (Unesp), Instituto de Biociências, Rio Claropt

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