N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions

Autores
Nayak, Mithilesh Kumar; Stubbe, Jessica; Neuman, Nicolás Ignacio; Narayanan, Ramakirushnan Suriya; Maji, Sandipan; Schulzke, Carola; Chandrasekhar, Vadapalli; Sarkar, Biprajit; Jana, Anukul
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We present here a stepwise reversible two-electrontransfer induced hydrogen shift leading to the conversion of a bis-pyrrolinium cation to an E-diaminoalkene and vice versa.Remarkably, the forward and the reverse reaction, which are bothreversible, follow two completely different reaction pathways.Establishing such unprecedented property in this type of processeswas possible by developing of a novel synthetic route towards thestarting dication. All intermediates involved in both the forward andthe backward reactions were comprehensively characterized by acombination of spectroscopic, crystallographic, electrochemical,spectroelectrochemical, and theoretical methods. The presentedsynthetic route opens up new possibilities for the generation of multi-pyrrolinium cation scaffold-based organic redox systems, whichconstitute decidedly sought-after molecules in contemporarychemistry.
Fil: Nayak, Mithilesh Kumar. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Stubbe, Jessica. Freie Universität Berlin.; Alemania
Fil: Neuman, Nicolás Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Narayanan, Ramakirushnan Suriya. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Maji, Sandipan. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Schulzke, Carola. ERNST MORITZ ARNDT UNIVERSITÄT GREIFSWALD (UG);
Fil: Chandrasekhar, Vadapalli. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Sarkar, Biprajit. Freie Universität Berlin.; Alemania
Fil: Jana, Anukul. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Materia
E-DIAMINOALKENE
CAAC
BISTABILITY
H-ATOM SHIFT
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:11336/106972
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/106972
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation ReactionsNayak, Mithilesh KumarStubbe, JessicaNeuman, Nicolás IgnacioNarayanan, Ramakirushnan SuriyaMaji, SandipanSchulzke, CarolaChandrasekhar, VadapalliSarkar, BiprajitJana, AnukulE-DIAMINOALKENECAACBISTABILITYH-ATOM SHIFThttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We present here a stepwise reversible two-electrontransfer induced hydrogen shift leading to the conversion of a bis-pyrrolinium cation to an E-diaminoalkene and vice versa.Remarkably, the forward and the reverse reaction, which are bothreversible, follow two completely different reaction pathways.Establishing such unprecedented property in this type of processeswas possible by developing of a novel synthetic route towards thestarting dication. All intermediates involved in both the forward andthe backward reactions were comprehensively characterized by acombination of spectroscopic, crystallographic, electrochemical,spectroelectrochemical, and theoretical methods. The presentedsynthetic route opens up new possibilities for the generation of multi-pyrrolinium cation scaffold-based organic redox systems, whichconstitute decidedly sought-after molecules in contemporarychemistry.Fil: Nayak, Mithilesh Kumar. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Stubbe, Jessica. Freie Universität Berlin.; AlemaniaFil: Neuman, Nicolás Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaFil: Narayanan, Ramakirushnan Suriya. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Maji, Sandipan. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Schulzke, Carola. ERNST MORITZ ARNDT UNIVERSITÄT GREIFSWALD (UG);Fil: Chandrasekhar, Vadapalli. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Sarkar, Biprajit. Freie Universität Berlin.; AlemaniaFil: Jana, Anukul. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaWiley VCH Verlag2020-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/106972Nayak, Mithilesh Kumar; Stubbe, Jessica; Neuman, Nicolás Ignacio; Narayanan, Ramakirushnan Suriya; Maji, Sandipan; et al.; N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions; Wiley VCH Verlag; Chemistry- A European Journal; 3-20200947-6539CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202000255info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.202000255info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:40:35Zoai:ri.conicet.gov.ar:11336/106972instacron: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:34982025-11-12 09:40:35.655CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
title N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
spellingShingle N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
Nayak, Mithilesh Kumar
E-DIAMINOALKENE
CAAC
BISTABILITY
H-ATOM SHIFT
title_short N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
title_full N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
title_fullStr N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
title_full_unstemmed N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
title_sort N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
dc.creator.none.fl_str_mv Nayak, Mithilesh Kumar
Stubbe, Jessica
Neuman, Nicolás Ignacio
Narayanan, Ramakirushnan Suriya
Maji, Sandipan
Schulzke, Carola
Chandrasekhar, Vadapalli
Sarkar, Biprajit
Jana, Anukul
author Nayak, Mithilesh Kumar
author_facet Nayak, Mithilesh Kumar
Stubbe, Jessica
Neuman, Nicolás Ignacio
Narayanan, Ramakirushnan Suriya
Maji, Sandipan
Schulzke, Carola
Chandrasekhar, Vadapalli
Sarkar, Biprajit
Jana, Anukul
author_role author
author2 Stubbe, Jessica
Neuman, Nicolás Ignacio
Narayanan, Ramakirushnan Suriya
Maji, Sandipan
Schulzke, Carola
Chandrasekhar, Vadapalli
Sarkar, Biprajit
Jana, Anukul
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv E-DIAMINOALKENE
CAAC
BISTABILITY
H-ATOM SHIFT
topic E-DIAMINOALKENE
CAAC
BISTABILITY
H-ATOM SHIFT
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv We present here a stepwise reversible two-electrontransfer induced hydrogen shift leading to the conversion of a bis-pyrrolinium cation to an E-diaminoalkene and vice versa.Remarkably, the forward and the reverse reaction, which are bothreversible, follow two completely different reaction pathways.Establishing such unprecedented property in this type of processeswas possible by developing of a novel synthetic route towards thestarting dication. All intermediates involved in both the forward andthe backward reactions were comprehensively characterized by acombination of spectroscopic, crystallographic, electrochemical,spectroelectrochemical, and theoretical methods. The presentedsynthetic route opens up new possibilities for the generation of multi-pyrrolinium cation scaffold-based organic redox systems, whichconstitute decidedly sought-after molecules in contemporarychemistry.
Fil: Nayak, Mithilesh Kumar. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Stubbe, Jessica. Freie Universität Berlin.; Alemania
Fil: Neuman, Nicolás Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Narayanan, Ramakirushnan Suriya. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Maji, Sandipan. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Schulzke, Carola. ERNST MORITZ ARNDT UNIVERSITÄT GREIFSWALD (UG);
Fil: Chandrasekhar, Vadapalli. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Sarkar, Biprajit. Freie Universität Berlin.; Alemania
Fil: Jana, Anukul. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
description We present here a stepwise reversible two-electrontransfer induced hydrogen shift leading to the conversion of a bis-pyrrolinium cation to an E-diaminoalkene and vice versa.Remarkably, the forward and the reverse reaction, which are bothreversible, follow two completely different reaction pathways.Establishing such unprecedented property in this type of processeswas possible by developing of a novel synthetic route towards thestarting dication. All intermediates involved in both the forward andthe backward reactions were comprehensively characterized by acombination of spectroscopic, crystallographic, electrochemical,spectroelectrochemical, and theoretical methods. The presentedsynthetic route opens up new possibilities for the generation of multi-pyrrolinium cation scaffold-based organic redox systems, whichconstitute decidedly sought-after molecules in contemporarychemistry.
publishDate 2020
dc.date.none.fl_str_mv 2020-03
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/11336/106972
Nayak, Mithilesh Kumar; Stubbe, Jessica; Neuman, Nicolás Ignacio; Narayanan, Ramakirushnan Suriya; Maji, Sandipan; et al.; N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions; Wiley VCH Verlag; Chemistry- A European Journal; 3-2020
0947-6539
CONICET Digital
CONICET
url http://hdl.handle.net/11336/106972
identifier_str_mv Nayak, Mithilesh Kumar; Stubbe, Jessica; Neuman, Nicolás Ignacio; Narayanan, Ramakirushnan Suriya; Maji, Sandipan; et al.; N , N′ ‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E ‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions; Wiley VCH Verlag; Chemistry- A European Journal; 3-2020
0947-6539
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://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202000255
info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.202000255
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
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
_version_ 1848597518829486080
score 13.24909

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