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dc.contributor.author
Bravo, Maria Virginia
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dc.contributor.author
Fernandez, Jose Luis
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dc.contributor.author
Adam, Claudia Guadalupe
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dc.contributor.author
Della Rosa, Claudia Daniela
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dc.date.available
2020-07-24T14:13:29Z
dc.date.issued
2019-07
dc.identifier.citation
Bravo, Maria Virginia; Fernandez, Jose Luis; Adam, Claudia Guadalupe; Della Rosa, Claudia Daniela; Understanding the Role of Protic Ionic Liquids (PILs) in Reactive Systems: Rational Selection of PILs for the Design of Green Synthesis Strategies for Allylic Amines and β‐Amino Esters; Wiley-VCH Verlag; ChemPlusChem; 84; 7; 7-2019; 919-926
dc.identifier.issn
2192-6506
dc.identifier.uri
http://hdl.handle.net/11336/110142
dc.description.abstract
The reactive behaviour of protic ionic liquids (PILs) has been shown to be governed not only by their chemical structures but also by their global compositions, which include the presence of free acids and bases at equilibrium with ionic pairs. Six PILs composed of primary, secondary, or tertiary alkyl ammonium cations with two couterions, nitrate or acetate, were tested in model reactions with unsaturated substrates. The free species that were naturally present in these liquids were identified by cyclic voltammetry. Only tributylammonium nitrate was found to be mostly composed just of the ionic pair; the other five PILs also contain variable amounts of free acid and amine. In reactive systems, these free species determine the products of the reaction. In particular, allylic amines and β-amino esters were obtained in good yields (91 and 75 %, respectively) by reaction of conjugated dienes and acrylates in the presence of PILs. By taking into account the actual composition of each PIL, it was possible to direct the reaction path towards a specific product with good yields, to ensure acid catalysis, to avoid polymerization of the substrate, and to promote phase transfer of products. These results establish some useful guidelines for the rational design of new PIL-based one-step synthetic strategies.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Wiley-VCH Verlag
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
PROTIC IONIC LIQUIDS
dc.subject
IONIC PAIRS
dc.subject
CYCLIC VOLTAMMETRY
dc.subject
GREEN SYNTHESIS
dc.subject.classification
Físico-Química, Ciencia de los Polímeros, Electroquímica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Understanding the Role of Protic Ionic Liquids (PILs) in Reactive Systems: Rational Selection of PILs for the Design of Green Synthesis Strategies for Allylic Amines and β‐Amino Esters
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-07-20T16:23:08Z
dc.journal.volume
84
dc.journal.number
7
dc.journal.pagination
919-926
dc.journal.pais
Alemania
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dc.journal.ciudad
Weinheim
dc.description.fil
Fil: Bravo, Maria Virginia. Universidad Nacional del Litoral. Instituto de Química Aplicada del Litoral. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Química Aplicada del Litoral.; Argentina
dc.description.fil
Fil: Fernandez, Jose Luis. (conicet/unlit); Argentina. Universidad Nacional del Litoral. Instituto de Química Aplicada del Litoral. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Química Aplicada del Litoral.; Argentina
dc.description.fil
Fil: Adam, Claudia Guadalupe. Universidad Nacional del Litoral. Instituto de Química Aplicada del Litoral. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Química Aplicada del Litoral.; Argentina
dc.description.fil
Fil: Della Rosa, Claudia Daniela. Universidad Nacional del Litoral. Instituto de Química Aplicada del Litoral. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Química Aplicada del Litoral.; Argentina
dc.journal.title
ChemPlusChem
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/cplu.201900318
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/cplu.201900318
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