A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction

Autores
Crosio, Matias Ariel; Correa, Nestor Mariano; Silber, Juana J.; Falcone, Ruben Dario
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, we have explored how the confinement of the protic ionic liquid (IL) ethylammonium nitrate (EAN) 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. To the best of our knowledge this is the first report where toluene/BHDC RMs use EAN as a polar component and it is used as a nanoreactor for carrying out kinetic experiments. Dynamic light scattering results reveal the formation of RMs containing the protic IL. The kinetic results show that upon confinement, EAN becomes a suitable solvent for the SN2 reaction while in homogeneous media it is a bad option. Entrapped in BHDC RMs, due to the strong hydrogen bond interactions, EAN behaves as an aprotic-like IL which cannot deactivate the nucleophilic power of Cl- and yet increases the substrate solubility. These facts show the versatility of this kind of organized system to alter the polar solvent entrapped and its influence on the reaction rate when it is used as a nanoreactor.
Fil: Crosio, Matias Ariel. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto; Argentina. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Silber, Juana J.. Universidad Nacional de Río Cuarto; Argentina
Fil: Falcone, Ruben Dario. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Materia
Reverse Micelle
Protic Ionic Liquid
Nucleophilic substitution
Ethylammonium nitrate
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:11336/160965
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/160965
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reactionCrosio, Matias ArielCorrea, Nestor MarianoSilber, Juana J.Falcone, Ruben DarioReverse MicelleProtic Ionic LiquidNucleophilic substitutionEthylammonium nitratehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work, we have explored how the confinement of the protic ionic liquid (IL) ethylammonium nitrate (EAN) 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. To the best of our knowledge this is the first report where toluene/BHDC RMs use EAN as a polar component and it is used as a nanoreactor for carrying out kinetic experiments. Dynamic light scattering results reveal the formation of RMs containing the protic IL. The kinetic results show that upon confinement, EAN becomes a suitable solvent for the SN2 reaction while in homogeneous media it is a bad option. Entrapped in BHDC RMs, due to the strong hydrogen bond interactions, EAN behaves as an aprotic-like IL which cannot deactivate the nucleophilic power of Cl- and yet increases the substrate solubility. These facts show the versatility of this kind of organized system to alter the polar solvent entrapped and its influence on the reaction rate when it is used as a nanoreactor.Fil: Crosio, Matias Ariel. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto; Argentina. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaFil: Silber, Juana J.. Universidad Nacional de Río Cuarto; ArgentinaFil: Falcone, Ruben Dario. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; ArgentinaRoyal Society of Chemistry2016-02info: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/11336/160965Crosio, Matias Ariel; Correa, Nestor Mariano; Silber, Juana J.; Falcone, Ruben Dario; A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 14; 11; 2-2016; 3170-31771477-05201477-0539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c5ob02664dinfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2016/OB/C5OB02664Dinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:49:39Zoai:ri.conicet.gov.ar:11336/160965instacron: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 09:49:40.018CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction
title A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction
spellingShingle A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction
Crosio, Matias Ariel
Reverse Micelle
Protic Ionic Liquid
Nucleophilic substitution
Ethylammonium nitrate
title_short A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction
title_full A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction
title_fullStr A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction
title_full_unstemmed A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction
title_sort A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction
dc.creator.none.fl_str_mv Crosio, Matias Ariel
Correa, Nestor Mariano
Silber, Juana J.
Falcone, Ruben Dario
author Crosio, Matias Ariel
author_facet Crosio, Matias Ariel
Correa, Nestor Mariano
Silber, Juana J.
Falcone, Ruben Dario
author_role author
author2 Correa, Nestor Mariano
Silber, Juana J.
Falcone, Ruben Dario
author2_role author
author
author
dc.subject.none.fl_str_mv Reverse Micelle
Protic Ionic Liquid
Nucleophilic substitution
Ethylammonium nitrate
topic Reverse Micelle
Protic Ionic Liquid
Nucleophilic substitution
Ethylammonium nitrate
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, we have explored how the confinement of the protic ionic liquid (IL) ethylammonium nitrate (EAN) 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. To the best of our knowledge this is the first report where toluene/BHDC RMs use EAN as a polar component and it is used as a nanoreactor for carrying out kinetic experiments. Dynamic light scattering results reveal the formation of RMs containing the protic IL. The kinetic results show that upon confinement, EAN becomes a suitable solvent for the SN2 reaction while in homogeneous media it is a bad option. Entrapped in BHDC RMs, due to the strong hydrogen bond interactions, EAN behaves as an aprotic-like IL which cannot deactivate the nucleophilic power of Cl- and yet increases the substrate solubility. These facts show the versatility of this kind of organized system to alter the polar solvent entrapped and its influence on the reaction rate when it is used as a nanoreactor.
Fil: Crosio, Matias Ariel. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Correa, Nestor Mariano. Universidad Nacional de Río Cuarto; Argentina. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
Fil: Silber, Juana J.. Universidad Nacional de Río Cuarto; Argentina
Fil: Falcone, Ruben Dario. Universidad Nacional de Río Cuarto. Instituto para el Desarrollo Agroindustrial y de la Salud. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto para el Desarrollo Agroindustrial y de la Salud; Argentina
description In this work, we have explored how the confinement of the protic ionic liquid (IL) ethylammonium nitrate (EAN) 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. To the best of our knowledge this is the first report where toluene/BHDC RMs use EAN as a polar component and it is used as a nanoreactor for carrying out kinetic experiments. Dynamic light scattering results reveal the formation of RMs containing the protic IL. The kinetic results show that upon confinement, EAN becomes a suitable solvent for the SN2 reaction while in homogeneous media it is a bad option. Entrapped in BHDC RMs, due to the strong hydrogen bond interactions, EAN behaves as an aprotic-like IL which cannot deactivate the nucleophilic power of Cl- and yet increases the substrate solubility. These facts show the versatility of this kind of organized system to alter the polar solvent entrapped and its influence on the reaction rate when it is used as a nanoreactor.
publishDate 2016
dc.date.none.fl_str_mv 2016-02
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/11336/160965
Crosio, Matias Ariel; Correa, Nestor Mariano; Silber, Juana J.; Falcone, Ruben Dario; A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 14; 11; 2-2016; 3170-3177
1477-0520
1477-0539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/160965
identifier_str_mv Crosio, Matias Ariel; Correa, Nestor Mariano; Silber, Juana J.; Falcone, Ruben Dario; A protic ionic liquid, when entrapped in cationic reverse micelles, can be used as a suitable solvent for a bimolecular nucleophilic substitution reaction; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 14; 11; 2-2016; 3170-3177
1477-0520
1477-0539
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c5ob02664d
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2016/OB/C5OB02664D
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 13.13397

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