Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†

Autores
Siano, Gastón; Crespi, Stefano; Bonesi, Sergio Mauricio
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.
Fil: Siano, Gastón. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Crespi, Stefano. University of Groningen; Países Bajos
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Materia
photochemistry
aryl benzoates
Photo-Fries rearrangement
Micellar environment
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:11336/181388
Acceder
id CONICETDig_20dc99ca83e634811391983298e98f98
oai_identifier_str oai:ri.conicet.gov.ar:11336/181388
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†Siano, GastónCrespi, StefanoBonesi, Sergio Mauriciophotochemistryaryl benzoatesPhoto-Fries rearrangementMicellar environmenthttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.Fil: Siano, Gastón. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Crespi, Stefano. University of Groningen; Países BajosFil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaWiley Blackwell Publishing, Inc2021-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/vnd.openxmlformats-officedocument.wordprocessingml.documentapplication/pdfhttp://hdl.handle.net/11336/181388Siano, Gastón; Crespi, Stefano; Bonesi, Sergio Mauricio; Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 97; 6; 11-2021; 1298-13090031-8655CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1111/php.13431info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1111/php.13431info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:59:36Zoai:ri.conicet.gov.ar:11336/181388instacron: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:34982025-10-15 14:59:37.172CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†
title Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†
spellingShingle Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†
Siano, Gastón
photochemistry
aryl benzoates
Photo-Fries rearrangement
Micellar environment
title_short Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†
title_full Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†
title_fullStr Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†
title_full_unstemmed Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†
title_sort Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†
dc.creator.none.fl_str_mv Siano, Gastón
Crespi, Stefano
Bonesi, Sergio Mauricio
author Siano, Gastón
author_facet Siano, Gastón
Crespi, Stefano
Bonesi, Sergio Mauricio
author_role author
author2 Crespi, Stefano
Bonesi, Sergio Mauricio
author2_role author
author
dc.subject.none.fl_str_mv photochemistry
aryl benzoates
Photo-Fries rearrangement
Micellar environment
topic photochemistry
aryl benzoates
Photo-Fries rearrangement
Micellar environment
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 carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.
Fil: Siano, Gastón. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Crespi, Stefano. University of Groningen; Países Bajos
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
description In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.
publishDate 2021
dc.date.none.fl_str_mv 2021-11
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/11336/181388
Siano, Gastón; Crespi, Stefano; Bonesi, Sergio Mauricio; Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 97; 6; 11-2021; 1298-1309
0031-8655
CONICET Digital
CONICET
url http://hdl.handle.net/11336/181388
identifier_str_mv Siano, Gastón; Crespi, Stefano; Bonesi, Sergio Mauricio; Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment†; Wiley Blackwell Publishing, Inc; Photochemistry and Photobiology; 97; 6; 11-2021; 1298-1309
0031-8655
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1111/php.13431
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1111/php.13431
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/vnd.openxmlformats-officedocument.wordprocessingml.document
application/pdf
dc.publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
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_ 1846083136229736448
score 13.22299

Publicaciones similares