Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene

Autores
Miñambres, Guadalupe Gloria; Jaques, Thomas Serpa; Veglia, Alicia Viviana; Lazzarotto, Márcio; Nachtigall, Francine Furtado
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Spectrophotometric titrations of calix[4]arene and p-tert-butylcalix[6]arene with LiOH, NaOH, KOH, tetramethylmmonium and tetrabutylammonium hydroxides as bases were carried in ethanol 95 % and acetonitrile. The dependence of pKa of the first deprotonation of calix[4]- arene with the nature of the cation was only modest in ethanol 95 %, spanning from 8.53 pKa unit for NaOH until 9.00 for LiOH, whereas in acetonitrile the proton transfer is quantitative. The first deprotonation of p-t-butylcalix[ 6]arene in both solvents is quantitative and the extension of the second deprotonation is very dependent of the nature of the cation in ethanol and acetonitrile. Tetramethylammonium hydroxide was the strongest base for both solvents, and both deprotonations proceed quantitatively and concomitantly in ethanol, followed by potassium hydroxide, and the weakest base was tetrabutylammonium hydroxide. This behavior indicates that the ability to form N+-C-H-π and K+-π interactions plays an important role to stabilize the mono and dianion calixarene. Lithium and sodium exhibit non-usual acid-base behavior in acetonitrile, attributed to aggregation of the species.
Fil: Miñambres, Guadalupe Gloria. 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: Jaques, Thomas Serpa. Universidade Federal do Rio Grande do Sul; Brasil
Fil: Veglia, Alicia 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: Lazzarotto, Márcio. Universidade Federal do Rio Grande do Sul; Brasil
Fil: Nachtigall, Francine Furtado. Superintendência do Rio Grande do Sul. INMETRO; Brasil
Materia
Calixarenes
Pka
Solvent Effects
Supramolecular Chemistry
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:11336/50183
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/50183
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]areneMiñambres, Guadalupe GloriaJaques, Thomas SerpaVeglia, Alicia VivianaLazzarotto, MárcioNachtigall, Francine FurtadoCalixarenesPkaSolvent EffectsSupramolecular Chemistryhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Spectrophotometric titrations of calix[4]arene and p-tert-butylcalix[6]arene with LiOH, NaOH, KOH, tetramethylmmonium and tetrabutylammonium hydroxides as bases were carried in ethanol 95 % and acetonitrile. The dependence of pKa of the first deprotonation of calix[4]- arene with the nature of the cation was only modest in ethanol 95 %, spanning from 8.53 pKa unit for NaOH until 9.00 for LiOH, whereas in acetonitrile the proton transfer is quantitative. The first deprotonation of p-t-butylcalix[ 6]arene in both solvents is quantitative and the extension of the second deprotonation is very dependent of the nature of the cation in ethanol and acetonitrile. Tetramethylammonium hydroxide was the strongest base for both solvents, and both deprotonations proceed quantitatively and concomitantly in ethanol, followed by potassium hydroxide, and the weakest base was tetrabutylammonium hydroxide. This behavior indicates that the ability to form N+-C-H-π and K+-π interactions plays an important role to stabilize the mono and dianion calixarene. Lithium and sodium exhibit non-usual acid-base behavior in acetonitrile, attributed to aggregation of the species.Fil: Miñambres, Guadalupe Gloria. 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: Jaques, Thomas Serpa. Universidade Federal do Rio Grande do Sul; BrasilFil: Veglia, Alicia 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: Lazzarotto, Márcio. Universidade Federal do Rio Grande do Sul; BrasilFil: Nachtigall, Francine Furtado. Superintendência do Rio Grande do Sul. INMETRO; BrasilSpringer2015-04info: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/11336/50183Miñambres, Guadalupe Gloria; Jaques, Thomas Serpa; Veglia, Alicia Viviana; Lazzarotto, Márcio; Nachtigall, Francine Furtado; Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene; Springer; Journal Of Inclusion Phenomena And Macrocyclic Chemistry; 81; 3-4; 4-2015; 311-3191388-31271573-1111CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s10847-014-0458-7info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs10847-014-0458-7info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:31:10Zoai:ri.conicet.gov.ar:11336/50183instacron: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:34982025-09-29 10:31:11.135CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
title Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
spellingShingle Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
Miñambres, Guadalupe Gloria
Calixarenes
Pka
Solvent Effects
Supramolecular Chemistry
title_short Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
title_full Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
title_fullStr Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
title_full_unstemmed Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
title_sort Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
dc.creator.none.fl_str_mv Miñambres, Guadalupe Gloria
Jaques, Thomas Serpa
Veglia, Alicia Viviana
Lazzarotto, Márcio
Nachtigall, Francine Furtado
author Miñambres, Guadalupe Gloria
author_facet Miñambres, Guadalupe Gloria
Jaques, Thomas Serpa
Veglia, Alicia Viviana
Lazzarotto, Márcio
Nachtigall, Francine Furtado
author_role author
author2 Jaques, Thomas Serpa
Veglia, Alicia Viviana
Lazzarotto, Márcio
Nachtigall, Francine Furtado
author2_role author
author
author
author
dc.subject.none.fl_str_mv Calixarenes
Pka
Solvent Effects
Supramolecular Chemistry
topic Calixarenes
Pka
Solvent Effects
Supramolecular Chemistry
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Spectrophotometric titrations of calix[4]arene and p-tert-butylcalix[6]arene with LiOH, NaOH, KOH, tetramethylmmonium and tetrabutylammonium hydroxides as bases were carried in ethanol 95 % and acetonitrile. The dependence of pKa of the first deprotonation of calix[4]- arene with the nature of the cation was only modest in ethanol 95 %, spanning from 8.53 pKa unit for NaOH until 9.00 for LiOH, whereas in acetonitrile the proton transfer is quantitative. The first deprotonation of p-t-butylcalix[ 6]arene in both solvents is quantitative and the extension of the second deprotonation is very dependent of the nature of the cation in ethanol and acetonitrile. Tetramethylammonium hydroxide was the strongest base for both solvents, and both deprotonations proceed quantitatively and concomitantly in ethanol, followed by potassium hydroxide, and the weakest base was tetrabutylammonium hydroxide. This behavior indicates that the ability to form N+-C-H-π and K+-π interactions plays an important role to stabilize the mono and dianion calixarene. Lithium and sodium exhibit non-usual acid-base behavior in acetonitrile, attributed to aggregation of the species.
Fil: Miñambres, Guadalupe Gloria. 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: Jaques, Thomas Serpa. Universidade Federal do Rio Grande do Sul; Brasil
Fil: Veglia, Alicia 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: Lazzarotto, Márcio. Universidade Federal do Rio Grande do Sul; Brasil
Fil: Nachtigall, Francine Furtado. Superintendência do Rio Grande do Sul. INMETRO; Brasil
description Spectrophotometric titrations of calix[4]arene and p-tert-butylcalix[6]arene with LiOH, NaOH, KOH, tetramethylmmonium and tetrabutylammonium hydroxides as bases were carried in ethanol 95 % and acetonitrile. The dependence of pKa of the first deprotonation of calix[4]- arene with the nature of the cation was only modest in ethanol 95 %, spanning from 8.53 pKa unit for NaOH until 9.00 for LiOH, whereas in acetonitrile the proton transfer is quantitative. The first deprotonation of p-t-butylcalix[ 6]arene in both solvents is quantitative and the extension of the second deprotonation is very dependent of the nature of the cation in ethanol and acetonitrile. Tetramethylammonium hydroxide was the strongest base for both solvents, and both deprotonations proceed quantitatively and concomitantly in ethanol, followed by potassium hydroxide, and the weakest base was tetrabutylammonium hydroxide. This behavior indicates that the ability to form N+-C-H-π and K+-π interactions plays an important role to stabilize the mono and dianion calixarene. Lithium and sodium exhibit non-usual acid-base behavior in acetonitrile, attributed to aggregation of the species.
publishDate 2015
dc.date.none.fl_str_mv 2015-04
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/11336/50183
Miñambres, Guadalupe Gloria; Jaques, Thomas Serpa; Veglia, Alicia Viviana; Lazzarotto, Márcio; Nachtigall, Francine Furtado; Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene; Springer; Journal Of Inclusion Phenomena And Macrocyclic Chemistry; 81; 3-4; 4-2015; 311-319
1388-3127
1573-1111
CONICET Digital
CONICET
url http://hdl.handle.net/11336/50183
identifier_str_mv Miñambres, Guadalupe Gloria; Jaques, Thomas Serpa; Veglia, Alicia Viviana; Lazzarotto, Márcio; Nachtigall, Francine Furtado; Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene; Springer; Journal Of Inclusion Phenomena And Macrocyclic Chemistry; 81; 3-4; 4-2015; 311-319
1388-3127
1573-1111
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s10847-014-0458-7
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1007%2Fs10847-014-0458-7
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 Springer
publisher.none.fl_str_mv Springer
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 13.069144

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