Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives

Autores
Martinis, Estefanía Mabel; Montellano, Alejandro; Sartorel, Andrea; Carraro, Mauro; Prato, Maurizio; Bonchio, Marcella
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The cycloaddition of azomethine ylides to [60]fullerene (C60) has been studied in ortho-dichlorobenzene (o-DCB) by evaluating the impact of an ionic liquid (IL) additive. The solvent effect has been addressed by evaluating the activation parameters of the cycloaddition and the boosting effect of the microwave (MW) induced dielectric heating. The IL additive plays a twofold role of stabilizing the dipolar ylide intermediate and favoring the retro-cycloaddition at high temperature regime. Under the conditions explored, a combined kinetic and thermodynamic preference favors the selective formation of trans bis-fulleropyrrolidine regioisomers, in agreement with the DFT computational analysis.
Fil: Martinis, Estefanía Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza; Argentina. Università di Padova; Italia. Universidad Nacional de Cuyo. Facultad de Ingeniería; Argentina
Fil: Montellano, Alejandro. Università degli Studi di Trieste; Italia
Fil: Sartorel, Andrea. Università di Padova; Italia
Fil: Carraro, Mauro. Università di Padova; Italia
Fil: Prato, Maurizio. Università degli Studi di Trieste; Italia. Basque Research and Technology Alliance; España. Basque Foundation for Science; España
Fil: Bonchio, Marcella. Università di Padova; Italia
Materia
1,3-DIPOLAR CYCLOADDITION
FULLERENES
IONIC LIQUIDS
MICROWAVES
TEMPERATURE EFFECT
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/167601
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additivesMartinis, Estefanía MabelMontellano, AlejandroSartorel, AndreaCarraro, MauroPrato, MaurizioBonchio, Marcella1,3-DIPOLAR CYCLOADDITIONFULLERENESIONIC LIQUIDSMICROWAVESTEMPERATURE EFFECThttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The cycloaddition of azomethine ylides to [60]fullerene (C60) has been studied in ortho-dichlorobenzene (o-DCB) by evaluating the impact of an ionic liquid (IL) additive. The solvent effect has been addressed by evaluating the activation parameters of the cycloaddition and the boosting effect of the microwave (MW) induced dielectric heating. The IL additive plays a twofold role of stabilizing the dipolar ylide intermediate and favoring the retro-cycloaddition at high temperature regime. Under the conditions explored, a combined kinetic and thermodynamic preference favors the selective formation of trans bis-fulleropyrrolidine regioisomers, in agreement with the DFT computational analysis.Fil: Martinis, Estefanía Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza; Argentina. Università di Padova; Italia. Universidad Nacional de Cuyo. Facultad de Ingeniería; ArgentinaFil: Montellano, Alejandro. Università degli Studi di Trieste; ItaliaFil: Sartorel, Andrea. Università di Padova; ItaliaFil: Carraro, Mauro. Università di Padova; ItaliaFil: Prato, Maurizio. Università degli Studi di Trieste; Italia. Basque Research and Technology Alliance; España. Basque Foundation for Science; EspañaFil: Bonchio, Marcella. Università di Padova; ItaliaWiley VCH Verlag2021-07info: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/11336/167601Martinis, Estefanía Mabel; Montellano, Alejandro; Sartorel, Andrea; Carraro, Mauro; Prato, Maurizio; et al.; Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives; Wiley VCH Verlag; European Journal of Organic Chemistry; 2021; 25; 7-2021; 3545-35511434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100546info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202100546info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-17T11:36:53Zoai:ri.conicet.gov.ar:11336/167601instacron: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:34982025-09-17 11:36:53.572CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives
title Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives
spellingShingle Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives
Martinis, Estefanía Mabel
1,3-DIPOLAR CYCLOADDITION
FULLERENES
IONIC LIQUIDS
MICROWAVES
TEMPERATURE EFFECT
title_short Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives
title_full Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives
title_fullStr Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives
title_full_unstemmed Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives
title_sort Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives
dc.creator.none.fl_str_mv Martinis, Estefanía Mabel
Montellano, Alejandro
Sartorel, Andrea
Carraro, Mauro
Prato, Maurizio
Bonchio, Marcella
author Martinis, Estefanía Mabel
author_facet Martinis, Estefanía Mabel
Montellano, Alejandro
Sartorel, Andrea
Carraro, Mauro
Prato, Maurizio
Bonchio, Marcella
author_role author
author2 Montellano, Alejandro
Sartorel, Andrea
Carraro, Mauro
Prato, Maurizio
Bonchio, Marcella
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv 1,3-DIPOLAR CYCLOADDITION
FULLERENES
IONIC LIQUIDS
MICROWAVES
TEMPERATURE EFFECT
topic 1,3-DIPOLAR CYCLOADDITION
FULLERENES
IONIC LIQUIDS
MICROWAVES
TEMPERATURE EFFECT
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 cycloaddition of azomethine ylides to [60]fullerene (C60) has been studied in ortho-dichlorobenzene (o-DCB) by evaluating the impact of an ionic liquid (IL) additive. The solvent effect has been addressed by evaluating the activation parameters of the cycloaddition and the boosting effect of the microwave (MW) induced dielectric heating. The IL additive plays a twofold role of stabilizing the dipolar ylide intermediate and favoring the retro-cycloaddition at high temperature regime. Under the conditions explored, a combined kinetic and thermodynamic preference favors the selective formation of trans bis-fulleropyrrolidine regioisomers, in agreement with the DFT computational analysis.
Fil: Martinis, Estefanía Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mendoza; Argentina. Università di Padova; Italia. Universidad Nacional de Cuyo. Facultad de Ingeniería; Argentina
Fil: Montellano, Alejandro. Università degli Studi di Trieste; Italia
Fil: Sartorel, Andrea. Università di Padova; Italia
Fil: Carraro, Mauro. Università di Padova; Italia
Fil: Prato, Maurizio. Università degli Studi di Trieste; Italia. Basque Research and Technology Alliance; España. Basque Foundation for Science; España
Fil: Bonchio, Marcella. Università di Padova; Italia
description The cycloaddition of azomethine ylides to [60]fullerene (C60) has been studied in ortho-dichlorobenzene (o-DCB) by evaluating the impact of an ionic liquid (IL) additive. The solvent effect has been addressed by evaluating the activation parameters of the cycloaddition and the boosting effect of the microwave (MW) induced dielectric heating. The IL additive plays a twofold role of stabilizing the dipolar ylide intermediate and favoring the retro-cycloaddition at high temperature regime. Under the conditions explored, a combined kinetic and thermodynamic preference favors the selective formation of trans bis-fulleropyrrolidine regioisomers, in agreement with the DFT computational analysis.
publishDate 2021
dc.date.none.fl_str_mv 2021-07
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/11336/167601
Martinis, Estefanía Mabel; Montellano, Alejandro; Sartorel, Andrea; Carraro, Mauro; Prato, Maurizio; et al.; Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives; Wiley VCH Verlag; European Journal of Organic Chemistry; 2021; 25; 7-2021; 3545-3551
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/167601
identifier_str_mv Martinis, Estefanía Mabel; Montellano, Alejandro; Sartorel, Andrea; Carraro, Mauro; Prato, Maurizio; et al.; Microwave-assisted 1,3-dipolar cycloaddition of azomethine ylides to [60]fullerene: thermodynamic control of bis-addition with ionic liquids additives; Wiley VCH Verlag; European Journal of Organic Chemistry; 2021; 25; 7-2021; 3545-3551
1434-193X
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://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202100546
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202100546
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 13.001348

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