Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene

Autores
Bouchet, Lydia María; Pierini, Adriana Beatriz; Brunetti, Veronica; Argüello, Juan Elias
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The initiation step of the photosubstitution reaction between 1-bromonaphthalene and a number of nucleophilic sulphur and selenium centred anions to afford 1-naphthylsulphide/selenide derivatives was investigated experimentally and by means of quantum chemical calculations. The frontier orbital energies of the anions were computed, and the values obtained agree with the lack of reactivity in the ground state. This model fails in accounting different reactivity of the anions toward the triplet state of 1-bromonaphthalene. Basicity and Eox were also calculated for all the anions finding a better agreement with the experimental reactivity and other measured properties such as pKa and oxidation potentials.
Fil: Bouchet, Lydia María. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Brunetti, Veronica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
Dft
Electrochemistry
Electron Transfer
Redox
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:11336/43404
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthaleneBouchet, Lydia MaríaPierini, Adriana BeatrizBrunetti, VeronicaArgüello, Juan EliasDftElectrochemistryElectron TransferRedoxhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The initiation step of the photosubstitution reaction between 1-bromonaphthalene and a number of nucleophilic sulphur and selenium centred anions to afford 1-naphthylsulphide/selenide derivatives was investigated experimentally and by means of quantum chemical calculations. The frontier orbital energies of the anions were computed, and the values obtained agree with the lack of reactivity in the ground state. This model fails in accounting different reactivity of the anions toward the triplet state of 1-bromonaphthalene. Basicity and Eox were also calculated for all the anions finding a better agreement with the experimental reactivity and other measured properties such as pKa and oxidation potentials.Fil: Bouchet, Lydia María. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Brunetti, Veronica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaJohn Wiley & Sons Ltd2016-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/43404Bouchet, Lydia María; Pierini, Adriana Beatriz; Brunetti, Veronica; Argüello, Juan Elias; Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 29; 11; 5-2016; 620-6280894-3230CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/poc.3568info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.3568info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-17T11:00:08Zoai:ri.conicet.gov.ar:11336/43404instacron: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:34982025-09-17 11:00:08.714CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene
title Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene
spellingShingle Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene
Bouchet, Lydia María
Dft
Electrochemistry
Electron Transfer
Redox
title_short Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene
title_full Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene
title_fullStr Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene
title_full_unstemmed Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene
title_sort Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene
dc.creator.none.fl_str_mv Bouchet, Lydia María
Pierini, Adriana Beatriz
Brunetti, Veronica
Argüello, Juan Elias
author Bouchet, Lydia María
author_facet Bouchet, Lydia María
Pierini, Adriana Beatriz
Brunetti, Veronica
Argüello, Juan Elias
author_role author
author2 Pierini, Adriana Beatriz
Brunetti, Veronica
Argüello, Juan Elias
author2_role author
author
author
dc.subject.none.fl_str_mv Dft
Electrochemistry
Electron Transfer
Redox
topic Dft
Electrochemistry
Electron Transfer
Redox
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The initiation step of the photosubstitution reaction between 1-bromonaphthalene and a number of nucleophilic sulphur and selenium centred anions to afford 1-naphthylsulphide/selenide derivatives was investigated experimentally and by means of quantum chemical calculations. The frontier orbital energies of the anions were computed, and the values obtained agree with the lack of reactivity in the ground state. This model fails in accounting different reactivity of the anions toward the triplet state of 1-bromonaphthalene. Basicity and Eox were also calculated for all the anions finding a better agreement with the experimental reactivity and other measured properties such as pKa and oxidation potentials.
Fil: Bouchet, Lydia María. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Pierini, Adriana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Brunetti, Veronica. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Argüello, Juan Elias. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description The initiation step of the photosubstitution reaction between 1-bromonaphthalene and a number of nucleophilic sulphur and selenium centred anions to afford 1-naphthylsulphide/selenide derivatives was investigated experimentally and by means of quantum chemical calculations. The frontier orbital energies of the anions were computed, and the values obtained agree with the lack of reactivity in the ground state. This model fails in accounting different reactivity of the anions toward the triplet state of 1-bromonaphthalene. Basicity and Eox were also calculated for all the anions finding a better agreement with the experimental reactivity and other measured properties such as pKa and oxidation potentials.
publishDate 2016
dc.date.none.fl_str_mv 2016-05
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/11336/43404
Bouchet, Lydia María; Pierini, Adriana Beatriz; Brunetti, Veronica; Argüello, Juan Elias; Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 29; 11; 5-2016; 620-628
0894-3230
CONICET Digital
CONICET
url http://hdl.handle.net/11336/43404
identifier_str_mv Bouchet, Lydia María; Pierini, Adriana Beatriz; Brunetti, Veronica; Argüello, Juan Elias; Electrochemical and computational study of the initiation step in the photoinduced electron transfer reaction between sulphur and selenide nucleophiles toward 1-bromonaphthalene; John Wiley & Sons Ltd; Journal Of Physical Organic Chemistry; 29; 11; 5-2016; 620-628
0894-3230
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/poc.3568
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.3568
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
application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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_ 1843606289469407232
score 13.001348

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