Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands

Autores
Mahata, Alok; Rudolf, Richard; Walter, Robert R. M.; Neuman, Nicolás Ignacio; Sarkar, Biprajit
Año de publicación
2025
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this study, we report our recent findings on the synthesis and reactivity of a novel 1,2,3-triazolin-5-imine-type mesoionic imine-carbodiimide (MII-CDI) adduct. Unlike reported NHC-CDI adducts, formed by the reactions of N-heterocyclic carbene (NHC) with CDI, these zwitterionic compounds undergo a spontaneous 1,3-hydrogen shift (1,3-H shift), resulting in guanidine-type compounds. The mechanism of this 1,3-H shift has been investigated through quantum chemical calculations. The MII-CDI adduct serves as a valuable synthon for the synthesis of mesoionic carbene-acyclic diamino carbene (MIC-ADC)-based nitreone (N(I)) compounds. We have conducted a detailed investigation into the electronic properties, chemical reactivity, and electrochemical behavior of these nitreone (N(I)) compounds. Additionally, the potential of these MII-CDI adducts as guanidinate ligands is explored. Our investigations here display the distinct reactivities of MII in contrast to their N-heterocyclic imine (NHI) congeners.
Fil: Mahata, Alok. Universitat Stuttgart; Alemania
Fil: Rudolf, Richard. Universitat Stuttgart; Alemania
Fil: Walter, Robert R. M.. Universitat Stuttgart; 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: Sarkar, Biprajit. Freie Universität Berlin; Alemania
Materia
MESOIONIC IMINE
NITREONE
RHODIUM
DENSITY FUNCTIONAL THEORY
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:11336/279817
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type LigandsMahata, AlokRudolf, RichardWalter, Robert R. M.Neuman, Nicolás IgnacioSarkar, BiprajitMESOIONIC IMINENITREONERHODIUMDENSITY FUNCTIONAL THEORYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this study, we report our recent findings on the synthesis and reactivity of a novel 1,2,3-triazolin-5-imine-type mesoionic imine-carbodiimide (MII-CDI) adduct. Unlike reported NHC-CDI adducts, formed by the reactions of N-heterocyclic carbene (NHC) with CDI, these zwitterionic compounds undergo a spontaneous 1,3-hydrogen shift (1,3-H shift), resulting in guanidine-type compounds. The mechanism of this 1,3-H shift has been investigated through quantum chemical calculations. The MII-CDI adduct serves as a valuable synthon for the synthesis of mesoionic carbene-acyclic diamino carbene (MIC-ADC)-based nitreone (N(I)) compounds. We have conducted a detailed investigation into the electronic properties, chemical reactivity, and electrochemical behavior of these nitreone (N(I)) compounds. Additionally, the potential of these MII-CDI adducts as guanidinate ligands is explored. Our investigations here display the distinct reactivities of MII in contrast to their N-heterocyclic imine (NHI) congeners.Fil: Mahata, Alok. Universitat Stuttgart; AlemaniaFil: Rudolf, Richard. Universitat Stuttgart; AlemaniaFil: Walter, Robert R. M.. Universitat Stuttgart; 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: Sarkar, Biprajit. Freie Universität Berlin; AlemaniaWiley VCH Verlag2025-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/279817Mahata, Alok; Rudolf, Richard; Walter, Robert R. M.; Neuman, Nicolás Ignacio; Sarkar, Biprajit; Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands; Wiley VCH Verlag; Angewandte Chemie; 64; 34; 7-2025; 1-121433-7851CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/anie.202502097info:eu-repo/semantics/altIdentifier/doi/10.1002/anie.202502097info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-02-26T10:34:54Zoai:ri.conicet.gov.ar:11336/279817instacron: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:34982026-02-26 10:34:54.713CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands
title Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands
spellingShingle Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands
Mahata, Alok
MESOIONIC IMINE
NITREONE
RHODIUM
DENSITY FUNCTIONAL THEORY
title_short Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands
title_full Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands
title_fullStr Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands
title_full_unstemmed Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands
title_sort Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands
dc.creator.none.fl_str_mv Mahata, Alok
Rudolf, Richard
Walter, Robert R. M.
Neuman, Nicolás Ignacio
Sarkar, Biprajit
author Mahata, Alok
author_facet Mahata, Alok
Rudolf, Richard
Walter, Robert R. M.
Neuman, Nicolás Ignacio
Sarkar, Biprajit
author_role author
author2 Rudolf, Richard
Walter, Robert R. M.
Neuman, Nicolás Ignacio
Sarkar, Biprajit
author2_role author
author
author
author
dc.subject.none.fl_str_mv MESOIONIC IMINE
NITREONE
RHODIUM
DENSITY FUNCTIONAL THEORY
topic MESOIONIC IMINE
NITREONE
RHODIUM
DENSITY FUNCTIONAL THEORY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this study, we report our recent findings on the synthesis and reactivity of a novel 1,2,3-triazolin-5-imine-type mesoionic imine-carbodiimide (MII-CDI) adduct. Unlike reported NHC-CDI adducts, formed by the reactions of N-heterocyclic carbene (NHC) with CDI, these zwitterionic compounds undergo a spontaneous 1,3-hydrogen shift (1,3-H shift), resulting in guanidine-type compounds. The mechanism of this 1,3-H shift has been investigated through quantum chemical calculations. The MII-CDI adduct serves as a valuable synthon for the synthesis of mesoionic carbene-acyclic diamino carbene (MIC-ADC)-based nitreone (N(I)) compounds. We have conducted a detailed investigation into the electronic properties, chemical reactivity, and electrochemical behavior of these nitreone (N(I)) compounds. Additionally, the potential of these MII-CDI adducts as guanidinate ligands is explored. Our investigations here display the distinct reactivities of MII in contrast to their N-heterocyclic imine (NHI) congeners.
Fil: Mahata, Alok. Universitat Stuttgart; Alemania
Fil: Rudolf, Richard. Universitat Stuttgart; Alemania
Fil: Walter, Robert R. M.. Universitat Stuttgart; 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: Sarkar, Biprajit. Freie Universität Berlin; Alemania
description In this study, we report our recent findings on the synthesis and reactivity of a novel 1,2,3-triazolin-5-imine-type mesoionic imine-carbodiimide (MII-CDI) adduct. Unlike reported NHC-CDI adducts, formed by the reactions of N-heterocyclic carbene (NHC) with CDI, these zwitterionic compounds undergo a spontaneous 1,3-hydrogen shift (1,3-H shift), resulting in guanidine-type compounds. The mechanism of this 1,3-H shift has been investigated through quantum chemical calculations. The MII-CDI adduct serves as a valuable synthon for the synthesis of mesoionic carbene-acyclic diamino carbene (MIC-ADC)-based nitreone (N(I)) compounds. We have conducted a detailed investigation into the electronic properties, chemical reactivity, and electrochemical behavior of these nitreone (N(I)) compounds. Additionally, the potential of these MII-CDI adducts as guanidinate ligands is explored. Our investigations here display the distinct reactivities of MII in contrast to their N-heterocyclic imine (NHI) congeners.
publishDate 2025
dc.date.none.fl_str_mv 2025-07
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/11336/279817
Mahata, Alok; Rudolf, Richard; Walter, Robert R. M.; Neuman, Nicolás Ignacio; Sarkar, Biprajit; Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands; Wiley VCH Verlag; Angewandte Chemie; 64; 34; 7-2025; 1-12
1433-7851
CONICET Digital
CONICET
url http://hdl.handle.net/11336/279817
identifier_str_mv Mahata, Alok; Rudolf, Richard; Walter, Robert R. M.; Neuman, Nicolás Ignacio; Sarkar, Biprajit; Exploring Mesoionic Imine‐Carbodiimide (MII‐CDI) Adducts: 1,3 H‐Shift, N(I) Compounds and Guanidinate‐Type Ligands; Wiley VCH Verlag; Angewandte Chemie; 64; 34; 7-2025; 1-12
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/https://onlinelibrary.wiley.com/doi/10.1002/anie.202502097
info:eu-repo/semantics/altIdentifier/doi/10.1002/anie.202502097
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
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score 12.665996

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