On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study

Autores
Silva, Oscar Fernando; Chessa, Juana Josefa; Hoyos, Maria Rita Micaela; Correa, Nestor Mariano; Fernández, Mariana Adela
Año de publicación
2007
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The formation of reverse micelles (RMs) of sodium 1,4-bis(2-ethylhexyl)sulfosuccinate (AOT) in n-heptane including two different â-cyclodextrin (â-CD) derivatives (hydroxypropyl-â-CD, hp-â-CD, and decenyl succinyl-â-CD, Mod-â-CD) is reported. Both cyclodextrins can be incorporated into AOT RMs in different zones within the aggregate, while â-CD cannot. Using UV-vis and induced circular dichroism (ICD) spectroscopy and different achiral molecular probes (some azo dyes, p-nitroaniline and ferrocene), it was possible to determine that Mod-â-CD is located with its cavity at the oil side of the AOT RM interface, while for hp-â-CD the cavity is inside the RM water pool. Among the molecular probes used, methyl orange (MO) was the only one which gave the ICD signal when dissolved in the AOT RMs with hp-â-CD, so a detailed study of MO behavior in homogeneous media was also performed to compare with the microheterogeneous media. The solvatochromic behavior of the dye depends not only on the polarity of the media but also on other specific solvent properties. A Kamlet-Taft analysis shows that the MO absorption spectrum shifts to longer wavelength with an increase in the solvent polarity-polarizability (π*) and the hydrogen donor ability (R) of the medium. MO appears to be almost 3 times more sensitive to the π* parameter than to the R parameter. In addition, from the MO absorption spectral changes with the hp-â-CD concentration, the association equilibrium constants in pure water (K11W) and inside the RMs (K11RM) were computed. The results show that K11W is almost 10 times larger than the value inside the RMs. The latter can be explained considering that MO resides anchored to the RM interface through hydrogen bond interaction with the hydration bound water. This study shows for the first time that the cyclodextrin chiral cavity is available for a guest in an organic medium such as the RMs; therefore, we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.
Fil: Silva, Oscar Fernando. 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: Chessa, Juana Josefa. 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: Correa, Nestor Mariano. 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: Fernández, Mariana Adela. 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
AOT
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:11336/240795
Acceder
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network_name_str CONICET Digital (CONICET)
spelling On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism StudySilva, Oscar FernandoChessa, Juana JosefaHoyos, Maria Rita MicaelaCorrea, Nestor MarianoFernández, Mariana AdelaAOThttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The formation of reverse micelles (RMs) of sodium 1,4-bis(2-ethylhexyl)sulfosuccinate (AOT) in n-heptane including two different â-cyclodextrin (â-CD) derivatives (hydroxypropyl-â-CD, hp-â-CD, and decenyl succinyl-â-CD, Mod-â-CD) is reported. Both cyclodextrins can be incorporated into AOT RMs in different zones within the aggregate, while â-CD cannot. Using UV-vis and induced circular dichroism (ICD) spectroscopy and different achiral molecular probes (some azo dyes, p-nitroaniline and ferrocene), it was possible to determine that Mod-â-CD is located with its cavity at the oil side of the AOT RM interface, while for hp-â-CD the cavity is inside the RM water pool. Among the molecular probes used, methyl orange (MO) was the only one which gave the ICD signal when dissolved in the AOT RMs with hp-â-CD, so a detailed study of MO behavior in homogeneous media was also performed to compare with the microheterogeneous media. The solvatochromic behavior of the dye depends not only on the polarity of the media but also on other specific solvent properties. A Kamlet-Taft analysis shows that the MO absorption spectrum shifts to longer wavelength with an increase in the solvent polarity-polarizability (π*) and the hydrogen donor ability (R) of the medium. MO appears to be almost 3 times more sensitive to the π* parameter than to the R parameter. In addition, from the MO absorption spectral changes with the hp-â-CD concentration, the association equilibrium constants in pure water (K11W) and inside the RMs (K11RM) were computed. The results show that K11W is almost 10 times larger than the value inside the RMs. The latter can be explained considering that MO resides anchored to the RM interface through hydrogen bond interaction with the hydration bound water. This study shows for the first time that the cyclodextrin chiral cavity is available for a guest in an organic medium such as the RMs; therefore, we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.Fil: Silva, Oscar Fernando. 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: Chessa, Juana Josefa. 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: Correa, Nestor Mariano. 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: Fernández, Mariana Adela. 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; ArgentinaAmerican Chemical Society2007-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/240795Silva, Oscar Fernando; Chessa, Juana Josefa; Hoyos, Maria Rita Micaela; Correa, Nestor Mariano; Fernández, Mariana Adela; On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study; American Chemical Society; Journal of Physical Chemistry B; 111; 36; 12-2007; 10703-107121089-56471520-6106CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp0724424info:eu-repo/semantics/altIdentifier/doi/10.1021/jp0724424info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:52:03Zoai:ri.conicet.gov.ar:11336/240795instacron: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 09:52:04.241CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study
title On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study
spellingShingle On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study
Silva, Oscar Fernando
AOT
title_short On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study
title_full On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study
title_fullStr On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study
title_full_unstemmed On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study
title_sort On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study
dc.creator.none.fl_str_mv Silva, Oscar Fernando
Chessa, Juana Josefa
Hoyos, Maria Rita Micaela
Correa, Nestor Mariano
Fernández, Mariana Adela
author Silva, Oscar Fernando
author_facet Silva, Oscar Fernando
Chessa, Juana Josefa
Hoyos, Maria Rita Micaela
Correa, Nestor Mariano
Fernández, Mariana Adela
author_role author
author2 Chessa, Juana Josefa
Hoyos, Maria Rita Micaela
Correa, Nestor Mariano
Fernández, Mariana Adela
author2_role author
author
author
author
dc.subject.none.fl_str_mv AOT
topic AOT
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 formation of reverse micelles (RMs) of sodium 1,4-bis(2-ethylhexyl)sulfosuccinate (AOT) in n-heptane including two different â-cyclodextrin (â-CD) derivatives (hydroxypropyl-â-CD, hp-â-CD, and decenyl succinyl-â-CD, Mod-â-CD) is reported. Both cyclodextrins can be incorporated into AOT RMs in different zones within the aggregate, while â-CD cannot. Using UV-vis and induced circular dichroism (ICD) spectroscopy and different achiral molecular probes (some azo dyes, p-nitroaniline and ferrocene), it was possible to determine that Mod-â-CD is located with its cavity at the oil side of the AOT RM interface, while for hp-â-CD the cavity is inside the RM water pool. Among the molecular probes used, methyl orange (MO) was the only one which gave the ICD signal when dissolved in the AOT RMs with hp-â-CD, so a detailed study of MO behavior in homogeneous media was also performed to compare with the microheterogeneous media. The solvatochromic behavior of the dye depends not only on the polarity of the media but also on other specific solvent properties. A Kamlet-Taft analysis shows that the MO absorption spectrum shifts to longer wavelength with an increase in the solvent polarity-polarizability (π*) and the hydrogen donor ability (R) of the medium. MO appears to be almost 3 times more sensitive to the π* parameter than to the R parameter. In addition, from the MO absorption spectral changes with the hp-â-CD concentration, the association equilibrium constants in pure water (K11W) and inside the RMs (K11RM) were computed. The results show that K11W is almost 10 times larger than the value inside the RMs. The latter can be explained considering that MO resides anchored to the RM interface through hydrogen bond interaction with the hydration bound water. This study shows for the first time that the cyclodextrin chiral cavity is available for a guest in an organic medium such as the RMs; therefore, we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.
Fil: Silva, Oscar Fernando. 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: Chessa, Juana Josefa. 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: Correa, Nestor Mariano. 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: Fernández, Mariana Adela. 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 formation of reverse micelles (RMs) of sodium 1,4-bis(2-ethylhexyl)sulfosuccinate (AOT) in n-heptane including two different â-cyclodextrin (â-CD) derivatives (hydroxypropyl-â-CD, hp-â-CD, and decenyl succinyl-â-CD, Mod-â-CD) is reported. Both cyclodextrins can be incorporated into AOT RMs in different zones within the aggregate, while â-CD cannot. Using UV-vis and induced circular dichroism (ICD) spectroscopy and different achiral molecular probes (some azo dyes, p-nitroaniline and ferrocene), it was possible to determine that Mod-â-CD is located with its cavity at the oil side of the AOT RM interface, while for hp-â-CD the cavity is inside the RM water pool. Among the molecular probes used, methyl orange (MO) was the only one which gave the ICD signal when dissolved in the AOT RMs with hp-â-CD, so a detailed study of MO behavior in homogeneous media was also performed to compare with the microheterogeneous media. The solvatochromic behavior of the dye depends not only on the polarity of the media but also on other specific solvent properties. A Kamlet-Taft analysis shows that the MO absorption spectrum shifts to longer wavelength with an increase in the solvent polarity-polarizability (π*) and the hydrogen donor ability (R) of the medium. MO appears to be almost 3 times more sensitive to the π* parameter than to the R parameter. In addition, from the MO absorption spectral changes with the hp-â-CD concentration, the association equilibrium constants in pure water (K11W) and inside the RMs (K11RM) were computed. The results show that K11W is almost 10 times larger than the value inside the RMs. The latter can be explained considering that MO resides anchored to the RM interface through hydrogen bond interaction with the hydration bound water. This study shows for the first time that the cyclodextrin chiral cavity is available for a guest in an organic medium such as the RMs; therefore, we have created a potentially powerful nanoreactor with two different confined regions in the same aggregate: the polar core of the RMs and the chiral hydrophobic cavity of cyclodextrin.
publishDate 2007
dc.date.none.fl_str_mv 2007-12
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/11336/240795
Silva, Oscar Fernando; Chessa, Juana Josefa; Hoyos, Maria Rita Micaela; Correa, Nestor Mariano; Fernández, Mariana Adela; On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study; American Chemical Society; Journal of Physical Chemistry B; 111; 36; 12-2007; 10703-10712
1089-5647
1520-6106
CONICET Digital
CONICET
url http://hdl.handle.net/11336/240795
identifier_str_mv Silva, Oscar Fernando; Chessa, Juana Josefa; Hoyos, Maria Rita Micaela; Correa, Nestor Mariano; Fernández, Mariana Adela; On the Possibility That Cyclodextrins' Chiral Cavities Can Be Available on AOT n -Heptane Reverse Micelles. A UV−Visible and Induced Circular Dichroism Study; American Chemical Society; Journal of Physical Chemistry B; 111; 36; 12-2007; 10703-10712
1089-5647
1520-6106
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp0724424
info:eu-repo/semantics/altIdentifier/doi/10.1021/jp0724424
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
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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