Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1

Autores
Adam, Claudia Guadalupe; Fortunato, Graciela Guadalupe; Mancini, Pedro Maximo Emilio
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This work presents a new approach using ionic liquids, namely ethylammonium nitrate. The aim was to analyze how the addition of small amounts of a protic ionic liquid to a pure molecular solvent, modifies the microscopic characteristics of a reaction medium. In order to achieve this, a kinetic study of nucleophilic aromatic substitution reactions between 1-fluoro-2,4-dinitrobenzene and 1-butylamine or piperidine was developed in this type of binary mixtures. We have detected nucleophiles competition originated by the presence of the ionic solvent at very low concentrations, observing the ethylamine derivative as the main substitution product. Moreover, in the light of previous results we have confirmed that the protic ionic liquid can act as both Brönsted acid and/or nucleophile. In this connection, we have selected the nucleophilic addition of amines to carbonyl compounds as reaction model. The protic ionic liquid in presence of aromatic aldehydes substituted by electron-donating groups makes possible the formation of the corresponding imines with good yields. The results demonstrated that the influence of the protic ionic liquid is very important in the course of both reaction systems.
Fil: Adam, Claudia Guadalupe. Universidad Nacional del Litoral; Argentina
Fil: Fortunato, Graciela Guadalupe. Universidad Nacional del Litoral; Argentina
Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral; Argentina
Materia
ionic liquids
1-fluoro-2,4-dinitrobenzene
amines
reactivity
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:11336/104091
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/104091
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1Adam, Claudia GuadalupeFortunato, Graciela GuadalupeMancini, Pedro Maximo Emilioionic liquids1-fluoro-2,4-dinitrobenzeneaminesreactivityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This work presents a new approach using ionic liquids, namely ethylammonium nitrate. The aim was to analyze how the addition of small amounts of a protic ionic liquid to a pure molecular solvent, modifies the microscopic characteristics of a reaction medium. In order to achieve this, a kinetic study of nucleophilic aromatic substitution reactions between 1-fluoro-2,4-dinitrobenzene and 1-butylamine or piperidine was developed in this type of binary mixtures. We have detected nucleophiles competition originated by the presence of the ionic solvent at very low concentrations, observing the ethylamine derivative as the main substitution product. Moreover, in the light of previous results we have confirmed that the protic ionic liquid can act as both Brönsted acid and/or nucleophile. In this connection, we have selected the nucleophilic addition of amines to carbonyl compounds as reaction model. The protic ionic liquid in presence of aromatic aldehydes substituted by electron-donating groups makes possible the formation of the corresponding imines with good yields. The results demonstrated that the influence of the protic ionic liquid is very important in the course of both reaction systems.Fil: Adam, Claudia Guadalupe. Universidad Nacional del Litoral; ArgentinaFil: Fortunato, Graciela Guadalupe. Universidad Nacional del Litoral; ArgentinaFil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral; ArgentinaJohn Wiley & Sons Ltd2009-05info: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/11336/104091Adam, Claudia Guadalupe; Fortunato, Graciela Guadalupe; Mancini, Pedro Maximo Emilio; Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 22; 5; 5-2009; 460-4650894-3230CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/poc.1501info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:10:11Zoai:ri.conicet.gov.ar:11336/104091instacron: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 10:10:11.701CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
title Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
spellingShingle Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
Adam, Claudia Guadalupe
ionic liquids
1-fluoro-2,4-dinitrobenzene
amines
reactivity
title_short Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
title_full Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
title_fullStr Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
title_full_unstemmed Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
title_sort Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
dc.creator.none.fl_str_mv Adam, Claudia Guadalupe
Fortunato, Graciela Guadalupe
Mancini, Pedro Maximo Emilio
author Adam, Claudia Guadalupe
author_facet Adam, Claudia Guadalupe
Fortunato, Graciela Guadalupe
Mancini, Pedro Maximo Emilio
author_role author
author2 Fortunato, Graciela Guadalupe
Mancini, Pedro Maximo Emilio
author2_role author
author
dc.subject.none.fl_str_mv ionic liquids
1-fluoro-2,4-dinitrobenzene
amines
reactivity
topic ionic liquids
1-fluoro-2,4-dinitrobenzene
amines
reactivity
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv This work presents a new approach using ionic liquids, namely ethylammonium nitrate. The aim was to analyze how the addition of small amounts of a protic ionic liquid to a pure molecular solvent, modifies the microscopic characteristics of a reaction medium. In order to achieve this, a kinetic study of nucleophilic aromatic substitution reactions between 1-fluoro-2,4-dinitrobenzene and 1-butylamine or piperidine was developed in this type of binary mixtures. We have detected nucleophiles competition originated by the presence of the ionic solvent at very low concentrations, observing the ethylamine derivative as the main substitution product. Moreover, in the light of previous results we have confirmed that the protic ionic liquid can act as both Brönsted acid and/or nucleophile. In this connection, we have selected the nucleophilic addition of amines to carbonyl compounds as reaction model. The protic ionic liquid in presence of aromatic aldehydes substituted by electron-donating groups makes possible the formation of the corresponding imines with good yields. The results demonstrated that the influence of the protic ionic liquid is very important in the course of both reaction systems.
Fil: Adam, Claudia Guadalupe. Universidad Nacional del Litoral; Argentina
Fil: Fortunato, Graciela Guadalupe. Universidad Nacional del Litoral; Argentina
Fil: Mancini, Pedro Maximo Emilio. Universidad Nacional del Litoral; Argentina
description This work presents a new approach using ionic liquids, namely ethylammonium nitrate. The aim was to analyze how the addition of small amounts of a protic ionic liquid to a pure molecular solvent, modifies the microscopic characteristics of a reaction medium. In order to achieve this, a kinetic study of nucleophilic aromatic substitution reactions between 1-fluoro-2,4-dinitrobenzene and 1-butylamine or piperidine was developed in this type of binary mixtures. We have detected nucleophiles competition originated by the presence of the ionic solvent at very low concentrations, observing the ethylamine derivative as the main substitution product. Moreover, in the light of previous results we have confirmed that the protic ionic liquid can act as both Brönsted acid and/or nucleophile. In this connection, we have selected the nucleophilic addition of amines to carbonyl compounds as reaction model. The protic ionic liquid in presence of aromatic aldehydes substituted by electron-donating groups makes possible the formation of the corresponding imines with good yields. The results demonstrated that the influence of the protic ionic liquid is very important in the course of both reaction systems.
publishDate 2009
dc.date.none.fl_str_mv 2009-05
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/11336/104091
Adam, Claudia Guadalupe; Fortunato, Graciela Guadalupe; Mancini, Pedro Maximo Emilio; Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 22; 5; 5-2009; 460-465
0894-3230
CONICET Digital
CONICET
url http://hdl.handle.net/11336/104091
identifier_str_mv Adam, Claudia Guadalupe; Fortunato, Graciela Guadalupe; Mancini, Pedro Maximo Emilio; Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 22; 5; 5-2009; 460-465
0894-3230
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.1501
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 John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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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