Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)

Autores
Baquero, Edwin A.; Silbestri, Gustavo Fabián; Gómez Sal, Pilar; Flores, Juan C.; de Jesús, Ernesto
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This report describes the synthesis of water-soluble silver(I) and platinum(II) complexes bearing sulfonated mono- or dianionic N-heterocyclic carbene ligands. Thus, treatment of the corresponding zwitterionic imidazolium derivative with silver(I) oxide in water afforded the light-sensitive bis(carbene) complexes Ag[Ag- (NHC)2] (2Ag+), which were transformed into the stable salts Na[Ag(NHC)2] (2) by addition of sodium chloride. In contrast, the same reaction in dmso afforded mono(carbenes) of general formula Na[AgCl(NHC)] (3). The solvent-dependence of the reaction product can be rationalized on the basis of the equilibrium [AgCl2]- --> AgCl + Cl-. The precipitation of silver chloride is more favored in protic solvents than in aprotic solvents such as dmso, thus explaining the formation of bis(carbenes) in water. The formation of silver chloride may also promote the hydrolysis of silver NHC complexes under some conditions. The water-soluble platinum(II) complexes Na[PtCl2(dmso)(NHC)] were synthesized by using either mono(carbene) silver complexes 3 as carbene-transfer agents or by direct metalation of the imidazolium salt with cis- [PtCl2(dmso)2] in the presence of NaHCO3 as base. The (NHC)Pt(II) complexes were tested as catalysts for the hydration of alkynes in the aqueous phase and found to be active in neat water without the need for acidic cocatalysts.
Fil: Baquero, Edwin A.. Universidad de Alcala. Facultad de Ciencias; España
Fil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad de Alcala; España
Fil: Gómez Sal, Pilar. Universidad de Alcala. Facultad de Ciencias; España
Fil: Flores, Juan C.. Universidad de Alcala. Facultad de Ciencias; España
Fil: de Jesús, Ernesto. Universidad de Alcala. Facultad de Ciencias; España
Materia
Nhc-Silver(I)
Nhc-Pt(Ii)
Sulfonated Nhc
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:11336/5421
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/5421
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)Baquero, Edwin A.Silbestri, Gustavo FabiánGómez Sal, PilarFlores, Juan C.de Jesús, ErnestoNhc-Silver(I)Nhc-Pt(Ii)Sulfonated Nhchttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This report describes the synthesis of water-soluble silver(I) and platinum(II) complexes bearing sulfonated mono- or dianionic N-heterocyclic carbene ligands. Thus, treatment of the corresponding zwitterionic imidazolium derivative with silver(I) oxide in water afforded the light-sensitive bis(carbene) complexes Ag[Ag- (NHC)2] (2Ag+), which were transformed into the stable salts Na[Ag(NHC)2] (2) by addition of sodium chloride. In contrast, the same reaction in dmso afforded mono(carbenes) of general formula Na[AgCl(NHC)] (3). The solvent-dependence of the reaction product can be rationalized on the basis of the equilibrium [AgCl2]- --> AgCl + Cl-. The precipitation of silver chloride is more favored in protic solvents than in aprotic solvents such as dmso, thus explaining the formation of bis(carbenes) in water. The formation of silver chloride may also promote the hydrolysis of silver NHC complexes under some conditions. The water-soluble platinum(II) complexes Na[PtCl2(dmso)(NHC)] were synthesized by using either mono(carbene) silver complexes 3 as carbene-transfer agents or by direct metalation of the imidazolium salt with cis- [PtCl2(dmso)2] in the presence of NaHCO3 as base. The (NHC)Pt(II) complexes were tested as catalysts for the hydration of alkynes in the aqueous phase and found to be active in neat water without the need for acidic cocatalysts.Fil: Baquero, Edwin A.. Universidad de Alcala. Facultad de Ciencias; EspañaFil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad de Alcala; EspañaFil: Gómez Sal, Pilar. Universidad de Alcala. Facultad de Ciencias; EspañaFil: Flores, Juan C.. Universidad de Alcala. Facultad de Ciencias; EspañaFil: de Jesús, Ernesto. Universidad de Alcala. Facultad de Ciencias; EspañaAmerican Chemical Society2013-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/5421Baquero, Edwin A.; Silbestri, Gustavo Fabián; Gómez Sal, Pilar; Flores, Juan C.; de Jesús, Ernesto; Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II); American Chemical Society; Organometallics; 32; 9; 4-2013; 2814-28260276-7333enginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/om400228sinfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1021/om400228sinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:03:37Zoai:ri.conicet.gov.ar:11336/5421instacron: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:34982025-09-03 10:03:37.83CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)
title Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)
spellingShingle Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)
Baquero, Edwin A.
Nhc-Silver(I)
Nhc-Pt(Ii)
Sulfonated Nhc
title_short Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)
title_full Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)
title_fullStr Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)
title_full_unstemmed Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)
title_sort Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II)
dc.creator.none.fl_str_mv Baquero, Edwin A.
Silbestri, Gustavo Fabián
Gómez Sal, Pilar
Flores, Juan C.
de Jesús, Ernesto
author Baquero, Edwin A.
author_facet Baquero, Edwin A.
Silbestri, Gustavo Fabián
Gómez Sal, Pilar
Flores, Juan C.
de Jesús, Ernesto
author_role author
author2 Silbestri, Gustavo Fabián
Gómez Sal, Pilar
Flores, Juan C.
de Jesús, Ernesto
author2_role author
author
author
author
dc.subject.none.fl_str_mv Nhc-Silver(I)
Nhc-Pt(Ii)
Sulfonated Nhc
topic Nhc-Silver(I)
Nhc-Pt(Ii)
Sulfonated Nhc
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv This report describes the synthesis of water-soluble silver(I) and platinum(II) complexes bearing sulfonated mono- or dianionic N-heterocyclic carbene ligands. Thus, treatment of the corresponding zwitterionic imidazolium derivative with silver(I) oxide in water afforded the light-sensitive bis(carbene) complexes Ag[Ag- (NHC)2] (2Ag+), which were transformed into the stable salts Na[Ag(NHC)2] (2) by addition of sodium chloride. In contrast, the same reaction in dmso afforded mono(carbenes) of general formula Na[AgCl(NHC)] (3). The solvent-dependence of the reaction product can be rationalized on the basis of the equilibrium [AgCl2]- --> AgCl + Cl-. The precipitation of silver chloride is more favored in protic solvents than in aprotic solvents such as dmso, thus explaining the formation of bis(carbenes) in water. The formation of silver chloride may also promote the hydrolysis of silver NHC complexes under some conditions. The water-soluble platinum(II) complexes Na[PtCl2(dmso)(NHC)] were synthesized by using either mono(carbene) silver complexes 3 as carbene-transfer agents or by direct metalation of the imidazolium salt with cis- [PtCl2(dmso)2] in the presence of NaHCO3 as base. The (NHC)Pt(II) complexes were tested as catalysts for the hydration of alkynes in the aqueous phase and found to be active in neat water without the need for acidic cocatalysts.
Fil: Baquero, Edwin A.. Universidad de Alcala. Facultad de Ciencias; España
Fil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina. Universidad de Alcala; España
Fil: Gómez Sal, Pilar. Universidad de Alcala. Facultad de Ciencias; España
Fil: Flores, Juan C.. Universidad de Alcala. Facultad de Ciencias; España
Fil: de Jesús, Ernesto. Universidad de Alcala. Facultad de Ciencias; España
description This report describes the synthesis of water-soluble silver(I) and platinum(II) complexes bearing sulfonated mono- or dianionic N-heterocyclic carbene ligands. Thus, treatment of the corresponding zwitterionic imidazolium derivative with silver(I) oxide in water afforded the light-sensitive bis(carbene) complexes Ag[Ag- (NHC)2] (2Ag+), which were transformed into the stable salts Na[Ag(NHC)2] (2) by addition of sodium chloride. In contrast, the same reaction in dmso afforded mono(carbenes) of general formula Na[AgCl(NHC)] (3). The solvent-dependence of the reaction product can be rationalized on the basis of the equilibrium [AgCl2]- --> AgCl + Cl-. The precipitation of silver chloride is more favored in protic solvents than in aprotic solvents such as dmso, thus explaining the formation of bis(carbenes) in water. The formation of silver chloride may also promote the hydrolysis of silver NHC complexes under some conditions. The water-soluble platinum(II) complexes Na[PtCl2(dmso)(NHC)] were synthesized by using either mono(carbene) silver complexes 3 as carbene-transfer agents or by direct metalation of the imidazolium salt with cis- [PtCl2(dmso)2] in the presence of NaHCO3 as base. The (NHC)Pt(II) complexes were tested as catalysts for the hydration of alkynes in the aqueous phase and found to be active in neat water without the need for acidic cocatalysts.
publishDate 2013
dc.date.none.fl_str_mv 2013-04
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/11336/5421
Baquero, Edwin A.; Silbestri, Gustavo Fabián; Gómez Sal, Pilar; Flores, Juan C.; de Jesús, Ernesto; Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II); American Chemical Society; Organometallics; 32; 9; 4-2013; 2814-2826
0276-7333
url http://hdl.handle.net/11336/5421
identifier_str_mv Baquero, Edwin A.; Silbestri, Gustavo Fabián; Gómez Sal, Pilar; Flores, Juan C.; de Jesús, Ernesto; Sulfonated Water-soluble N-Heterocyclic Carbene Silver(I) Complexes: Behavior in Aqueous Medium and as NHC-transfer Agents to Platinum(II); American Chemical Society; Organometallics; 32; 9; 4-2013; 2814-2826
0276-7333
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/om400228s
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1021/om400228s
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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_ 1842269811007029248
score 13.13397

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