Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction

Autores
Villa, Cristian C.; Correa, Nestor Mariano; Silber, Juana J.; Falcone, Ruben Dario
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The effect of interfacial water entrapped in two types of catanionic reverse micelles (RMs) on the kinetic parameters of the SN2 reaction between dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate (S+) and n-butylamine (BuNH2) was explored. Two catanionic surfactants, composed of a mixture of oppositely charged ionic surfactants without their original counterions, were used to create the RMs. Thus, benzyl-n-hexadecyldimethylammonium 1,4-bis(2-ethylhexyl) sulfosuccinate (BHD-AOT) and cetyltrimethylammonium 1,4-bis(2-ethylhexyl) sulfosuccinate (CTA-AOT) were formed. Also, the well-known anionic surfactant sodium 1,4-bis(2-ethylhexyl) sulfosuccinate (Na-AOT) was employed as a comparison. Our results showed an important catalytic-like effect of all RMs investigated in comparison with a water-benzene mixture, and the rate constant values depend on the type of surfactant used. Faster reaction in BHD-AOT RMs than in CTA-AOT and Na-AOT RMs was observed. This behavior was attributed to the strong interaction (by hydrogen bonding with AOT anion and ion-dipole interaction with BHD+) between the entrapped water and the BHD-AOT interface, which reduces the solvation capacity of water on S+. In CTA-AOT (and Na-AOT) RMs, the water-interface interaction is weaker and the electron pairs of water can solvate S+ ions. In summary, the chemical structure of the counterion on the catanionic surfactant alters the interfacial region, allowing the progress of a reaction inside the RMs to be controlled. ©
Fil: Villa, Cristian C.. Universidad del Quindio; Colombia
Fil: Correa, Nestor Mariano. 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. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; 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. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
REVERSE MICELLES
CATANIONIC SURFACTANTS
IONIC LIQUID SURFACTANTS
CONFINED WATER
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:11336/120837
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/120837
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reactionVilla, Cristian C.Correa, Nestor MarianoSilber, Juana J.Falcone, Ruben DarioREVERSE MICELLESCATANIONIC SURFACTANTSIONIC LIQUID SURFACTANTSCONFINED WATERhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The effect of interfacial water entrapped in two types of catanionic reverse micelles (RMs) on the kinetic parameters of the SN2 reaction between dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate (S+) and n-butylamine (BuNH2) was explored. Two catanionic surfactants, composed of a mixture of oppositely charged ionic surfactants without their original counterions, were used to create the RMs. Thus, benzyl-n-hexadecyldimethylammonium 1,4-bis(2-ethylhexyl) sulfosuccinate (BHD-AOT) and cetyltrimethylammonium 1,4-bis(2-ethylhexyl) sulfosuccinate (CTA-AOT) were formed. Also, the well-known anionic surfactant sodium 1,4-bis(2-ethylhexyl) sulfosuccinate (Na-AOT) was employed as a comparison. Our results showed an important catalytic-like effect of all RMs investigated in comparison with a water-benzene mixture, and the rate constant values depend on the type of surfactant used. Faster reaction in BHD-AOT RMs than in CTA-AOT and Na-AOT RMs was observed. This behavior was attributed to the strong interaction (by hydrogen bonding with AOT anion and ion-dipole interaction with BHD+) between the entrapped water and the BHD-AOT interface, which reduces the solvation capacity of water on S+. In CTA-AOT (and Na-AOT) RMs, the water-interface interaction is weaker and the electron pairs of water can solvate S+ ions. In summary, the chemical structure of the counterion on the catanionic surfactant alters the interfacial region, allowing the progress of a reaction inside the RMs to be controlled. ©Fil: Villa, Cristian C.. Universidad del Quindio; ColombiaFil: Correa, Nestor Mariano. 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. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; 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; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaAmerican Chemical Society2019-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/120837Villa, Cristian C.; Correa, Nestor Mariano; Silber, Juana J.; Falcone, Ruben Dario; Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction; American Chemical Society; Journal of Organic Chemistry; 84; 3; 2-2019; 1185-11910022-32631520-6904CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.8b02492info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.8b02492info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:07:45Zoai:ri.conicet.gov.ar:11336/120837instacron: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 10:07:45.478CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction
title Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction
spellingShingle Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction
Villa, Cristian C.
REVERSE MICELLES
CATANIONIC SURFACTANTS
IONIC LIQUID SURFACTANTS
CONFINED WATER
title_short Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction
title_full Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction
title_fullStr Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction
title_full_unstemmed Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction
title_sort Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction
dc.creator.none.fl_str_mv Villa, Cristian C.
Correa, Nestor Mariano
Silber, Juana J.
Falcone, Ruben Dario
author Villa, Cristian C.
author_facet Villa, Cristian C.
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 MICELLES
CATANIONIC SURFACTANTS
IONIC LIQUID SURFACTANTS
CONFINED WATER
topic REVERSE MICELLES
CATANIONIC SURFACTANTS
IONIC LIQUID SURFACTANTS
CONFINED WATER
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 effect of interfacial water entrapped in two types of catanionic reverse micelles (RMs) on the kinetic parameters of the SN2 reaction between dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate (S+) and n-butylamine (BuNH2) was explored. Two catanionic surfactants, composed of a mixture of oppositely charged ionic surfactants without their original counterions, were used to create the RMs. Thus, benzyl-n-hexadecyldimethylammonium 1,4-bis(2-ethylhexyl) sulfosuccinate (BHD-AOT) and cetyltrimethylammonium 1,4-bis(2-ethylhexyl) sulfosuccinate (CTA-AOT) were formed. Also, the well-known anionic surfactant sodium 1,4-bis(2-ethylhexyl) sulfosuccinate (Na-AOT) was employed as a comparison. Our results showed an important catalytic-like effect of all RMs investigated in comparison with a water-benzene mixture, and the rate constant values depend on the type of surfactant used. Faster reaction in BHD-AOT RMs than in CTA-AOT and Na-AOT RMs was observed. This behavior was attributed to the strong interaction (by hydrogen bonding with AOT anion and ion-dipole interaction with BHD+) between the entrapped water and the BHD-AOT interface, which reduces the solvation capacity of water on S+. In CTA-AOT (and Na-AOT) RMs, the water-interface interaction is weaker and the electron pairs of water can solvate S+ ions. In summary, the chemical structure of the counterion on the catanionic surfactant alters the interfacial region, allowing the progress of a reaction inside the RMs to be controlled. ©
Fil: Villa, Cristian C.. Universidad del Quindio; Colombia
Fil: Correa, Nestor Mariano. 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. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; 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. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description The effect of interfacial water entrapped in two types of catanionic reverse micelles (RMs) on the kinetic parameters of the SN2 reaction between dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate (S+) and n-butylamine (BuNH2) was explored. Two catanionic surfactants, composed of a mixture of oppositely charged ionic surfactants without their original counterions, were used to create the RMs. Thus, benzyl-n-hexadecyldimethylammonium 1,4-bis(2-ethylhexyl) sulfosuccinate (BHD-AOT) and cetyltrimethylammonium 1,4-bis(2-ethylhexyl) sulfosuccinate (CTA-AOT) were formed. Also, the well-known anionic surfactant sodium 1,4-bis(2-ethylhexyl) sulfosuccinate (Na-AOT) was employed as a comparison. Our results showed an important catalytic-like effect of all RMs investigated in comparison with a water-benzene mixture, and the rate constant values depend on the type of surfactant used. Faster reaction in BHD-AOT RMs than in CTA-AOT and Na-AOT RMs was observed. This behavior was attributed to the strong interaction (by hydrogen bonding with AOT anion and ion-dipole interaction with BHD+) between the entrapped water and the BHD-AOT interface, which reduces the solvation capacity of water on S+. In CTA-AOT (and Na-AOT) RMs, the water-interface interaction is weaker and the electron pairs of water can solvate S+ ions. In summary, the chemical structure of the counterion on the catanionic surfactant alters the interfacial region, allowing the progress of a reaction inside the RMs to be controlled. ©
publishDate 2019
dc.date.none.fl_str_mv 2019-02
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/11336/120837
Villa, Cristian C.; Correa, Nestor Mariano; Silber, Juana J.; Falcone, Ruben Dario; Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction; American Chemical Society; Journal of Organic Chemistry; 84; 3; 2-2019; 1185-1191
0022-3263
1520-6904
CONICET Digital
CONICET
url http://hdl.handle.net/11336/120837
identifier_str_mv Villa, Cristian C.; Correa, Nestor Mariano; Silber, Juana J.; Falcone, Ruben Dario; Catanionic reverse micelles as an optimal microenvironment to alter the water electron donor capacity in a SN2 reaction; American Chemical Society; Journal of Organic Chemistry; 84; 3; 2-2019; 1185-1191
0022-3263
1520-6904
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/acs.joc.8b02492
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.8b02492
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
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
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score 13.13397

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