Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex

In this work we analyze the whole molecular mechanism for intramolecular aromatic hydroxylation through O2 activation by a Schiff hexaazamacrocyclic dicopper(I) complex, [CuI2(bsH2m)]2+. Assisted by DFT calculations, we unravel the reaction pathway for the overall intramolecular aromatic hydroxylati...

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Detalles Bibliográficos
Autores: Poater Teixidor, Albert, Solà i Puig, Miquel
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2013
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/8382
Acceso en línea:http://hdl.handle.net/10256/8382
Access Level:acceso abierto
Palabra clave:Compostos aromàtics
Aromatic compounds
Enllaços químics
Chemical bonds
Química quàntica
Quantum chemistry
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spelling Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complexPoater Teixidor, AlbertSolà i Puig, MiquelCompostos aromàticsAromatic compoundsEnllaços químicsChemical bondsQuímica quànticaQuantum chemistryIn this work we analyze the whole molecular mechanism for intramolecular aromatic hydroxylation through O2 activation by a Schiff hexaazamacrocyclic dicopper(I) complex, [CuI2(bsH2m)]2+. Assisted by DFT calculations, we unravel the reaction pathway for the overall intramolecular aromatic hydroxylation, i.e., from the initial O2 reaction with the dicopper(I) species to first form a CuICuII-superoxo species, the subsequent reaction with the second CuI center to form a μ-η2:η2-peroxo-CuII 2 intermediate, the concerted peroxide O–O bond cleavage and C–O bond formation, followed finally by a proton transfer to an alpha aromatic carbon that immediately yields the product [CuII 2(bsH2m-O)(μ-OH)]2+Beilstein-InstitutMinisterio de Ciencia e Innovación (Espanya)Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca2013info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/8382http://hdl.handle.net/10256/8382Beilstein Journal of Organic Chemistry, 2013, núm. 9, p. 585-593Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.9.63info:eu-repo/semantics/altIdentifier/eissn/1860-5397info:eu-repo/grantAgreement/MICINN//RYC-2009-05226info:eu-repo/grantAgreement/MICINN//CTQ2011-23156AGAUR/2009-2014/2009 SGR-637AGAUR/2011BE100793info:eu-repo/grantAgreement/EC/FP7/293900Attribution 3.0 Spainhttp://creativecommons.org/licenses/by/3.0/es/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/83822026-05-29T05:05:01Z
dc.title.none.fl_str_mv Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex
title Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex
spellingShingle Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex
Poater Teixidor, Albert
Compostos aromàtics
Aromatic compounds
Enllaços químics
Chemical bonds
Química quàntica
Quantum chemistry
title_short Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex
title_full Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex
title_fullStr Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex
title_full_unstemmed Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex
title_sort Complete σ* intramolecular aromatic hydroxylation mechanism through O2 activation by a Schiff base macrocyclic dicopper (I) complex
dc.creator.none.fl_str_mv Poater Teixidor, Albert
Solà i Puig, Miquel
author Poater Teixidor, Albert
author_facet Poater Teixidor, Albert
Solà i Puig, Miquel
author_role author
author2 Solà i Puig, Miquel
author2_role author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca
dc.subject.none.fl_str_mv Compostos aromàtics
Aromatic compounds
Enllaços químics
Chemical bonds
Química quàntica
Quantum chemistry
topic Compostos aromàtics
Aromatic compounds
Enllaços químics
Chemical bonds
Química quàntica
Quantum chemistry
description In this work we analyze the whole molecular mechanism for intramolecular aromatic hydroxylation through O2 activation by a Schiff hexaazamacrocyclic dicopper(I) complex, [CuI2(bsH2m)]2+. Assisted by DFT calculations, we unravel the reaction pathway for the overall intramolecular aromatic hydroxylation, i.e., from the initial O2 reaction with the dicopper(I) species to first form a CuICuII-superoxo species, the subsequent reaction with the second CuI center to form a μ-η2:η2-peroxo-CuII 2 intermediate, the concerted peroxide O–O bond cleavage and C–O bond formation, followed finally by a proton transfer to an alpha aromatic carbon that immediately yields the product [CuII 2(bsH2m-O)(μ-OH)]2+
publishDate 2013
dc.date.none.fl_str_mv 2013
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/8382
http://hdl.handle.net/10256/8382
url http://hdl.handle.net/10256/8382
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3762/bjoc.9.63
info:eu-repo/semantics/altIdentifier/eissn/1860-5397
info:eu-repo/grantAgreement/MICINN//RYC-2009-05226
info:eu-repo/grantAgreement/MICINN//CTQ2011-23156
AGAUR/2009-2014/2009 SGR-637
AGAUR/2011BE100793
info:eu-repo/grantAgreement/EC/FP7/293900
dc.rights.none.fl_str_mv Attribution 3.0 Spain
http://creativecommons.org/licenses/by/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution 3.0 Spain
http://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Beilstein-Institut
publisher.none.fl_str_mv Beilstein-Institut
dc.source.none.fl_str_mv Beilstein Journal of Organic Chemistry, 2013, núm. 9, p. 585-593
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.811543

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