CAAC-Based Thiele and Schlenk Hydrocarbons

Autores
Maiti, Avijit; Stubbe, Jessica; Neuman, Nicolás Ignacio; Kalita, Pankaj; Duari, Prakash; Schulzke, Carola; Chandrasekhar, Vadapalli; Sarkar, Biprajit; Jana, Anukul
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Diradicals have been of tremendous interest for over a century ever since the first reports of p- and m-phenylene-bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele´s hydrocarbon, a Kekulé diradical, and Schlenk´s hydrocarbon, a non-Kekulé diradical, without using CAAC as a precursor. The CAAC analogue of Thiele´s hydrocarbon has a singlet ground state, whereas the CAAC analogue of Schlenk´s hydrocarbon contains two unpaired electrons. The latter forms a dimer, by an intermolecular double head-to-tail dimerization. This straightforward synthetic methodology is modular and can be extended for the generation of redox-active organic compounds.
Fil: Maiti, Avijit. 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: Kalita, Pankaj. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Duari, Prakash. 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
CAAC
Diradicals
Redox-Active Organic Compounds
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:11336/107025
Acceder
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network_name_str CONICET Digital (CONICET)
spelling CAAC-Based Thiele and Schlenk HydrocarbonsMaiti, AvijitStubbe, JessicaNeuman, Nicolás IgnacioKalita, PankajDuari, PrakashSchulzke, CarolaChandrasekhar, VadapalliSarkar, BiprajitJana, AnukulCAACDiradicalsRedox-Active Organic Compoundshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Diradicals have been of tremendous interest for over a century ever since the first reports of p- and m-phenylene-bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele´s hydrocarbon, a Kekulé diradical, and Schlenk´s hydrocarbon, a non-Kekulé diradical, without using CAAC as a precursor. The CAAC analogue of Thiele´s hydrocarbon has a singlet ground state, whereas the CAAC analogue of Schlenk´s hydrocarbon contains two unpaired electrons. The latter forms a dimer, by an intermolecular double head-to-tail dimerization. This straightforward synthetic methodology is modular and can be extended for the generation of redox-active organic compounds.Fil: Maiti, Avijit. 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: Kalita, Pankaj. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Duari, Prakash. 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/11336/107025Maiti, Avijit; Stubbe, Jessica; Neuman, Nicolás Ignacio; Kalita, Pankaj; Duari, Prakash; et al.; CAAC-Based Thiele and Schlenk Hydrocarbons; Wiley VCH Verlag; Angewandte Chemie; 3-2020; 1-71433-7851CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://doi.wiley.com/10.1002/anie.201915802info:eu-repo/semantics/altIdentifier/doi/10.1002/anie.201915802info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:38:51Zoai:ri.conicet.gov.ar:11336/107025instacron: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 09:38:51.911CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv CAAC-Based Thiele and Schlenk Hydrocarbons
title CAAC-Based Thiele and Schlenk Hydrocarbons
spellingShingle CAAC-Based Thiele and Schlenk Hydrocarbons
Maiti, Avijit
CAAC
Diradicals
Redox-Active Organic Compounds
title_short CAAC-Based Thiele and Schlenk Hydrocarbons
title_full CAAC-Based Thiele and Schlenk Hydrocarbons
title_fullStr CAAC-Based Thiele and Schlenk Hydrocarbons
title_full_unstemmed CAAC-Based Thiele and Schlenk Hydrocarbons
title_sort CAAC-Based Thiele and Schlenk Hydrocarbons
dc.creator.none.fl_str_mv Maiti, Avijit
Stubbe, Jessica
Neuman, Nicolás Ignacio
Kalita, Pankaj
Duari, Prakash
Schulzke, Carola
Chandrasekhar, Vadapalli
Sarkar, Biprajit
Jana, Anukul
author Maiti, Avijit
author_facet Maiti, Avijit
Stubbe, Jessica
Neuman, Nicolás Ignacio
Kalita, Pankaj
Duari, Prakash
Schulzke, Carola
Chandrasekhar, Vadapalli
Sarkar, Biprajit
Jana, Anukul
author_role author
author2 Stubbe, Jessica
Neuman, Nicolás Ignacio
Kalita, Pankaj
Duari, Prakash
Schulzke, Carola
Chandrasekhar, Vadapalli
Sarkar, Biprajit
Jana, Anukul
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv CAAC
Diradicals
Redox-Active Organic Compounds
topic CAAC
Diradicals
Redox-Active Organic Compounds
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Diradicals have been of tremendous interest for over a century ever since the first reports of p- and m-phenylene-bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele´s hydrocarbon, a Kekulé diradical, and Schlenk´s hydrocarbon, a non-Kekulé diradical, without using CAAC as a precursor. The CAAC analogue of Thiele´s hydrocarbon has a singlet ground state, whereas the CAAC analogue of Schlenk´s hydrocarbon contains two unpaired electrons. The latter forms a dimer, by an intermolecular double head-to-tail dimerization. This straightforward synthetic methodology is modular and can be extended for the generation of redox-active organic compounds.
Fil: Maiti, Avijit. 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: Kalita, Pankaj. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Duari, Prakash. 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 Diradicals have been of tremendous interest for over a century ever since the first reports of p- and m-phenylene-bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele´s hydrocarbon, a Kekulé diradical, and Schlenk´s hydrocarbon, a non-Kekulé diradical, without using CAAC as a precursor. The CAAC analogue of Thiele´s hydrocarbon has a singlet ground state, whereas the CAAC analogue of Schlenk´s hydrocarbon contains two unpaired electrons. The latter forms a dimer, by an intermolecular double head-to-tail dimerization. This straightforward synthetic methodology is modular and can be extended for the generation of redox-active organic compounds.
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/11336/107025
Maiti, Avijit; Stubbe, Jessica; Neuman, Nicolás Ignacio; Kalita, Pankaj; Duari, Prakash; et al.; CAAC-Based Thiele and Schlenk Hydrocarbons; Wiley VCH Verlag; Angewandte Chemie; 3-2020; 1-7
1433-7851
CONICET Digital
CONICET
url http://hdl.handle.net/11336/107025
identifier_str_mv Maiti, Avijit; Stubbe, Jessica; Neuman, Nicolás Ignacio; Kalita, Pankaj; Duari, Prakash; et al.; CAAC-Based Thiele and Schlenk Hydrocarbons; Wiley VCH Verlag; Angewandte Chemie; 3-2020; 1-7
1433-7851
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://doi.wiley.com/10.1002/anie.201915802
info:eu-repo/semantics/altIdentifier/doi/10.1002/anie.201915802
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
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 13.24909

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