Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins

Autores
Rougier, Natalia Mercedes; Vico, Raquel Viviana; Hoyos, Maria Rita Micaela; Bujan, Elba Ines
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The reaction of Fenitrothion with O and N nucleophiles (H2O2, NH2OH, n-butylamine and piperidine) was studied at 25 °C in water containing 2% 1,4-dioxane in the presence of native cyclodextrins (α-, β-, and γ-CD). For all the nucleophiles, the presence of CD produces reaction inhibition with saturation kinetics. The greatest effect in all cases is observed with β-CD, and the greatest inhibition was observed for the reaction of Fenitrothion with H2O2 (81%), which is the most efficient nucleophile in promoting Fenitrothion degradation in homogeneous media. In the absence of CD, competition between the SN2(P) and the SN2(C) pathways was observed with piperidine as was reported before for the reaction with NH2OH and n-butylamine. The presence of β-CD does not modify product distribution in the case of the reaction with NH2OH and n-butylamine, whereas there is an increase in SN2(C) pathway when the nucleophile is piperidine.
Fil: Rougier, Natalia Mercedes. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Vico, Raquel Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Hoyos, Maria Rita Micaela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Bujan, Elba Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
Aminolysis
Cyclodextrins
Host Guest Systems
Hydrogen Peroxide
Inclusion Complexes
Organophosphorus Insecticides
Reaction Mechanisms
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/31558
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/31558
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrinsRougier, Natalia MercedesVico, Raquel VivianaHoyos, Maria Rita MicaelaBujan, Elba InesAminolysisCyclodextrinsHost Guest SystemsHydrogen PeroxideInclusion ComplexesOrganophosphorus InsecticidesReaction Mechanismshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The reaction of Fenitrothion with O and N nucleophiles (H2O2, NH2OH, n-butylamine and piperidine) was studied at 25 °C in water containing 2% 1,4-dioxane in the presence of native cyclodextrins (α-, β-, and γ-CD). For all the nucleophiles, the presence of CD produces reaction inhibition with saturation kinetics. The greatest effect in all cases is observed with β-CD, and the greatest inhibition was observed for the reaction of Fenitrothion with H2O2 (81%), which is the most efficient nucleophile in promoting Fenitrothion degradation in homogeneous media. In the absence of CD, competition between the SN2(P) and the SN2(C) pathways was observed with piperidine as was reported before for the reaction with NH2OH and n-butylamine. The presence of β-CD does not modify product distribution in the case of the reaction with NH2OH and n-butylamine, whereas there is an increase in SN2(C) pathway when the nucleophile is piperidine.Fil: Rougier, Natalia Mercedes. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Vico, Raquel Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Hoyos, Maria Rita Micaela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Bujan, Elba Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaJohn Wiley & Sons Ltd2014-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/31558Bujan, Elba Ines; Hoyos, Maria Rita Micaela; Vico, Raquel Viviana; Rougier, Natalia Mercedes; Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 27; 12; 11-2014; 935-9430894-3230CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/poc.3373info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/poc.3373/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-12-17T14:15:57Zoai:ri.conicet.gov.ar:11336/31558instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-12-17 14:15:58.031CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
title Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
spellingShingle Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
Rougier, Natalia Mercedes
Aminolysis
Cyclodextrins
Host Guest Systems
Hydrogen Peroxide
Inclusion Complexes
Organophosphorus Insecticides
Reaction Mechanisms
title_short Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
title_full Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
title_fullStr Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
title_full_unstemmed Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
title_sort Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins
dc.creator.none.fl_str_mv Rougier, Natalia Mercedes
Vico, Raquel Viviana
Hoyos, Maria Rita Micaela
Bujan, Elba Ines
author Rougier, Natalia Mercedes
author_facet Rougier, Natalia Mercedes
Vico, Raquel Viviana
Hoyos, Maria Rita Micaela
Bujan, Elba Ines
author_role author
author2 Vico, Raquel Viviana
Hoyos, Maria Rita Micaela
Bujan, Elba Ines
author2_role author
author
author
dc.subject.none.fl_str_mv Aminolysis
Cyclodextrins
Host Guest Systems
Hydrogen Peroxide
Inclusion Complexes
Organophosphorus Insecticides
Reaction Mechanisms
topic Aminolysis
Cyclodextrins
Host Guest Systems
Hydrogen Peroxide
Inclusion Complexes
Organophosphorus Insecticides
Reaction Mechanisms
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The reaction of Fenitrothion with O and N nucleophiles (H2O2, NH2OH, n-butylamine and piperidine) was studied at 25 °C in water containing 2% 1,4-dioxane in the presence of native cyclodextrins (α-, β-, and γ-CD). For all the nucleophiles, the presence of CD produces reaction inhibition with saturation kinetics. The greatest effect in all cases is observed with β-CD, and the greatest inhibition was observed for the reaction of Fenitrothion with H2O2 (81%), which is the most efficient nucleophile in promoting Fenitrothion degradation in homogeneous media. In the absence of CD, competition between the SN2(P) and the SN2(C) pathways was observed with piperidine as was reported before for the reaction with NH2OH and n-butylamine. The presence of β-CD does not modify product distribution in the case of the reaction with NH2OH and n-butylamine, whereas there is an increase in SN2(C) pathway when the nucleophile is piperidine.
Fil: Rougier, Natalia Mercedes. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Vico, Raquel Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Hoyos, Maria Rita Micaela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Bujan, Elba Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description The reaction of Fenitrothion with O and N nucleophiles (H2O2, NH2OH, n-butylamine and piperidine) was studied at 25 °C in water containing 2% 1,4-dioxane in the presence of native cyclodextrins (α-, β-, and γ-CD). For all the nucleophiles, the presence of CD produces reaction inhibition with saturation kinetics. The greatest effect in all cases is observed with β-CD, and the greatest inhibition was observed for the reaction of Fenitrothion with H2O2 (81%), which is the most efficient nucleophile in promoting Fenitrothion degradation in homogeneous media. In the absence of CD, competition between the SN2(P) and the SN2(C) pathways was observed with piperidine as was reported before for the reaction with NH2OH and n-butylamine. The presence of β-CD does not modify product distribution in the case of the reaction with NH2OH and n-butylamine, whereas there is an increase in SN2(C) pathway when the nucleophile is piperidine.
publishDate 2014
dc.date.none.fl_str_mv 2014-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/31558
Bujan, Elba Ines; Hoyos, Maria Rita Micaela; Vico, Raquel Viviana; Rougier, Natalia Mercedes; Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 27; 12; 11-2014; 935-943
0894-3230
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31558
identifier_str_mv Bujan, Elba Ines; Hoyos, Maria Rita Micaela; Vico, Raquel Viviana; Rougier, Natalia Mercedes; Stabilization of the pesticide Fenitrothion toward O and N nucleophiles in the presence of cyclodextrins; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 27; 12; 11-2014; 935-943
0894-3230
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.3373
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/poc.3373/abstract
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.176297

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