Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability

Autores
Blach Vargas, Diana; Pessêgo, Marcia; Chessa, Juana Josefa; Correa, Nestor Mariano; Garcia Rio, Luis; Falcone, Ruben Dario
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work was explored how the confinement of two ionic liquids (ILs), 1-butyl-3-methylimidazolium chloride (bmimCl) and 1-butyl-3-methylimidazolium tetrafluoroborate (bmimBF4), inside toluene/benzyl-n-hexadecyldimethylammonium chloride (BHDC) reverse micelles (RMs) affects the Cl– nucleophilicity on the bimolecular nucleophilic substitution (SN2) reaction between this anion and dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate. The results obtained show that, upon confinement, the ionic interactions between the ILs with the cationic surfactant polar head group and the surfactant counterion modify substantially the performance of both ILs as solvents. In toluene/BHDC/bmimCl RMs, the Cl– interacts strongly with bmim+ (and/or BHD+) in such a way that its nucleophilicity is reduced in comparison with neat IL. In toluene/BHDC/bmimBF4 RMs, an ionic exchange equilibrium produces segregation of bmim+ and BF4– ions, changing the composition of the RMs interface and affecting dramatically the Cl– availability. These results show the versatility of this kind of organized system to alter the ionic organization and influence on reaction rate when used as nanoreactors.
Fil: Blach Vargas, Diana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Pessêgo, Marcia. Universidad de Santiago de Compostela; España. Universidade do Algarve; Portugal
Fil: Chessa, Juana Josefa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Garcia Rio, Luis. Universidad de Santiago de Compostela; España
Fil: Falcone, Ruben Dario. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
Ionic Liquids
Reverse Micelles
Bhdc
Sn2
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:11336/33968
Acceder
id CONICETDig_f8ccc74f146369fd693bc4cdd41bc480
oai_identifier_str oai:ri.conicet.gov.ar:11336/33968
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion AvailabilityBlach Vargas, DianaPessêgo, MarciaChessa, Juana JosefaCorrea, Nestor MarianoGarcia Rio, LuisFalcone, Ruben DarioIonic LiquidsReverse MicellesBhdcSn2https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work was explored how the confinement of two ionic liquids (ILs), 1-butyl-3-methylimidazolium chloride (bmimCl) and 1-butyl-3-methylimidazolium tetrafluoroborate (bmimBF4), inside toluene/benzyl-n-hexadecyldimethylammonium chloride (BHDC) reverse micelles (RMs) affects the Cl– nucleophilicity on the bimolecular nucleophilic substitution (SN2) reaction between this anion and dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate. The results obtained show that, upon confinement, the ionic interactions between the ILs with the cationic surfactant polar head group and the surfactant counterion modify substantially the performance of both ILs as solvents. In toluene/BHDC/bmimCl RMs, the Cl– interacts strongly with bmim+ (and/or BHD+) in such a way that its nucleophilicity is reduced in comparison with neat IL. In toluene/BHDC/bmimBF4 RMs, an ionic exchange equilibrium produces segregation of bmim+ and BF4– ions, changing the composition of the RMs interface and affecting dramatically the Cl– availability. These results show the versatility of this kind of organized system to alter the ionic organization and influence on reaction rate when used as nanoreactors.Fil: Blach Vargas, Diana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Pessêgo, Marcia. Universidad de Santiago de Compostela; España. Universidade do Algarve; PortugalFil: Chessa, Juana Josefa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Garcia Rio, Luis. Universidad de Santiago de Compostela; EspañaFil: Falcone, Ruben Dario. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaAmerican Chemical Society2014-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/33968Blach Vargas, Diana; Pessêgo, Marcia; Chessa, Juana Josefa; Correa, Nestor Mariano; Garcia Rio, Luis; et al.; Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability; American Chemical Society; Langmuir; 30; 41; 4-2014; 12130-121370743-7463CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/la501496ainfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/la501496ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:44:27Zoai:ri.conicet.gov.ar:11336/33968instacron: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:34982025-09-03 09:44:28.236CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability
title Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability
spellingShingle Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability
Blach Vargas, Diana
Ionic Liquids
Reverse Micelles
Bhdc
Sn2
title_short Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability
title_full Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability
title_fullStr Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability
title_full_unstemmed Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability
title_sort Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability
dc.creator.none.fl_str_mv Blach Vargas, Diana
Pessêgo, Marcia
Chessa, Juana Josefa
Correa, Nestor Mariano
Garcia Rio, Luis
Falcone, Ruben Dario
author Blach Vargas, Diana
author_facet Blach Vargas, Diana
Pessêgo, Marcia
Chessa, Juana Josefa
Correa, Nestor Mariano
Garcia Rio, Luis
Falcone, Ruben Dario
author_role author
author2 Pessêgo, Marcia
Chessa, Juana Josefa
Correa, Nestor Mariano
Garcia Rio, Luis
Falcone, Ruben Dario
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Ionic Liquids
Reverse Micelles
Bhdc
Sn2
topic Ionic Liquids
Reverse Micelles
Bhdc
Sn2
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work was explored how the confinement of two ionic liquids (ILs), 1-butyl-3-methylimidazolium chloride (bmimCl) and 1-butyl-3-methylimidazolium tetrafluoroborate (bmimBF4), inside toluene/benzyl-n-hexadecyldimethylammonium chloride (BHDC) reverse micelles (RMs) affects the Cl– nucleophilicity on the bimolecular nucleophilic substitution (SN2) reaction between this anion and dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate. The results obtained show that, upon confinement, the ionic interactions between the ILs with the cationic surfactant polar head group and the surfactant counterion modify substantially the performance of both ILs as solvents. In toluene/BHDC/bmimCl RMs, the Cl– interacts strongly with bmim+ (and/or BHD+) in such a way that its nucleophilicity is reduced in comparison with neat IL. In toluene/BHDC/bmimBF4 RMs, an ionic exchange equilibrium produces segregation of bmim+ and BF4– ions, changing the composition of the RMs interface and affecting dramatically the Cl– availability. These results show the versatility of this kind of organized system to alter the ionic organization and influence on reaction rate when used as nanoreactors.
Fil: Blach Vargas, Diana. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Pessêgo, Marcia. Universidad de Santiago de Compostela; España. Universidade do Algarve; Portugal
Fil: Chessa, Juana Josefa. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Garcia Rio, Luis. Universidad de Santiago de Compostela; España
Fil: Falcone, Ruben Dario. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description In this work was explored how the confinement of two ionic liquids (ILs), 1-butyl-3-methylimidazolium chloride (bmimCl) and 1-butyl-3-methylimidazolium tetrafluoroborate (bmimBF4), inside toluene/benzyl-n-hexadecyldimethylammonium chloride (BHDC) reverse micelles (RMs) affects the Cl– nucleophilicity on the bimolecular nucleophilic substitution (SN2) reaction between this anion and dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate. The results obtained show that, upon confinement, the ionic interactions between the ILs with the cationic surfactant polar head group and the surfactant counterion modify substantially the performance of both ILs as solvents. In toluene/BHDC/bmimCl RMs, the Cl– interacts strongly with bmim+ (and/or BHD+) in such a way that its nucleophilicity is reduced in comparison with neat IL. In toluene/BHDC/bmimBF4 RMs, an ionic exchange equilibrium produces segregation of bmim+ and BF4– ions, changing the composition of the RMs interface and affecting dramatically the Cl– availability. These results show the versatility of this kind of organized system to alter the ionic organization and influence on reaction rate when used as nanoreactors.
publishDate 2014
dc.date.none.fl_str_mv 2014-04
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/11336/33968
Blach Vargas, Diana; Pessêgo, Marcia; Chessa, Juana Josefa; Correa, Nestor Mariano; Garcia Rio, Luis; et al.; Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability; American Chemical Society; Langmuir; 30; 41; 4-2014; 12130-12137
0743-7463
CONICET Digital
CONICET
url http://hdl.handle.net/11336/33968
identifier_str_mv Blach Vargas, Diana; Pessêgo, Marcia; Chessa, Juana Josefa; Correa, Nestor Mariano; Garcia Rio, Luis; et al.; Ionic Liquids Entrapped in Reverse Micelles as Nanoreactors for Bimolecular Nucleophilic Substitution Reaction. Effect of the Confinement on the Chloride Ion Availability; American Chemical Society; Langmuir; 30; 41; 4-2014; 12130-12137
0743-7463
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/la501496a
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/10.1021/la501496a
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
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
_version_ 1842268668524756992
score 13.13397

Publicaciones similares