Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide

Autores
Manetti, Martin Diego; Burgos Paci, Maximiliano Alberto; Argüello, Gustavo Alejandro
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This paper reports for the first time the synthesis and characterization of trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F. The new trioxide is obtained from the gas-phase photolytic reaction of CF 3C(O)OC(O)CF3and FC(O)C(O)F at 223-228 K. It is a very thermally labile molecule that decomposes at room temperature by rupture of either of the CF3OC(O)O-O-OC(O)F bonds. These bonds are nonequivalent, and a branching ratio of 0.8 for fragmentation through the CF3OC(O)OO-OC(O)F bond was obtained. Unambiguous identification was possible through reaction of the trioxide with an excess of NO2. Potential-energy surfaces (PES) of the different rotamers were studied by the B3LYP/6-311+G* method, and analysis of the IR frequency of the possible mixture of rotamers agrees excellently with the experimental IR spectrum. This molecule is the first nonsymmetric acyl trioxide reported in the literature.
Fil: Manetti, Martin Diego. Universidad Nacional de Cordoba. Facultad de Cs.quimicas. Centro de Quimica Aplicada; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Burgos Paci, Maximiliano Alberto. 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, Gustavo Alejandro. 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
Fluorinated Compounds
Thermal Decompositions
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:11336/76928
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/76928
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxideManetti, Martin DiegoBurgos Paci, Maximiliano AlbertoArgüello, Gustavo AlejandroFluorinated CompoundsThermal Decompositionshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This paper reports for the first time the synthesis and characterization of trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F. The new trioxide is obtained from the gas-phase photolytic reaction of CF 3C(O)OC(O)CF3and FC(O)C(O)F at 223-228 K. It is a very thermally labile molecule that decomposes at room temperature by rupture of either of the CF3OC(O)O-O-OC(O)F bonds. These bonds are nonequivalent, and a branching ratio of 0.8 for fragmentation through the CF3OC(O)OO-OC(O)F bond was obtained. Unambiguous identification was possible through reaction of the trioxide with an excess of NO2. Potential-energy surfaces (PES) of the different rotamers were studied by the B3LYP/6-311+G* method, and analysis of the IR frequency of the possible mixture of rotamers agrees excellently with the experimental IR spectrum. This molecule is the first nonsymmetric acyl trioxide reported in the literature.Fil: Manetti, Martin Diego. Universidad Nacional de Cordoba. Facultad de Cs.quimicas. Centro de Quimica Aplicada; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Burgos Paci, Maximiliano Alberto. 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, Gustavo Alejandro. 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; ArgentinaAmerican Chemical Society2009-07info: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/11336/76928Manetti, Martin Diego; Burgos Paci, Maximiliano Alberto; Argüello, Gustavo Alejandro; Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide; American Chemical Society; Journal of Physical Chemistry A; 113; 30; 7-2009; 8523-85281089-56391520-5215CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp9022772info:eu-repo/semantics/altIdentifier/doi/10.1021/jp9022772info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:31:02Zoai:ri.conicet.gov.ar:11336/76928instacron: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:34982025-09-29 10:31:03.019CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide
title Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide
spellingShingle Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide
Manetti, Martin Diego
Fluorinated Compounds
Thermal Decompositions
title_short Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide
title_full Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide
title_fullStr Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide
title_full_unstemmed Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide
title_sort Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide
dc.creator.none.fl_str_mv Manetti, Martin Diego
Burgos Paci, Maximiliano Alberto
Argüello, Gustavo Alejandro
author Manetti, Martin Diego
author_facet Manetti, Martin Diego
Burgos Paci, Maximiliano Alberto
Argüello, Gustavo Alejandro
author_role author
author2 Burgos Paci, Maximiliano Alberto
Argüello, Gustavo Alejandro
author2_role author
author
dc.subject.none.fl_str_mv Fluorinated Compounds
Thermal Decompositions
topic Fluorinated Compounds
Thermal Decompositions
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 paper reports for the first time the synthesis and characterization of trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F. The new trioxide is obtained from the gas-phase photolytic reaction of CF 3C(O)OC(O)CF3and FC(O)C(O)F at 223-228 K. It is a very thermally labile molecule that decomposes at room temperature by rupture of either of the CF3OC(O)O-O-OC(O)F bonds. These bonds are nonequivalent, and a branching ratio of 0.8 for fragmentation through the CF3OC(O)OO-OC(O)F bond was obtained. Unambiguous identification was possible through reaction of the trioxide with an excess of NO2. Potential-energy surfaces (PES) of the different rotamers were studied by the B3LYP/6-311+G* method, and analysis of the IR frequency of the possible mixture of rotamers agrees excellently with the experimental IR spectrum. This molecule is the first nonsymmetric acyl trioxide reported in the literature.
Fil: Manetti, Martin Diego. Universidad Nacional de Cordoba. Facultad de Cs.quimicas. Centro de Quimica Aplicada; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Burgos Paci, Maximiliano Alberto. 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, Gustavo Alejandro. 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 This paper reports for the first time the synthesis and characterization of trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F. The new trioxide is obtained from the gas-phase photolytic reaction of CF 3C(O)OC(O)CF3and FC(O)C(O)F at 223-228 K. It is a very thermally labile molecule that decomposes at room temperature by rupture of either of the CF3OC(O)O-O-OC(O)F bonds. These bonds are nonequivalent, and a branching ratio of 0.8 for fragmentation through the CF3OC(O)OO-OC(O)F bond was obtained. Unambiguous identification was possible through reaction of the trioxide with an excess of NO2. Potential-energy surfaces (PES) of the different rotamers were studied by the B3LYP/6-311+G* method, and analysis of the IR frequency of the possible mixture of rotamers agrees excellently with the experimental IR spectrum. This molecule is the first nonsymmetric acyl trioxide reported in the literature.
publishDate 2009
dc.date.none.fl_str_mv 2009-07
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/11336/76928
Manetti, Martin Diego; Burgos Paci, Maximiliano Alberto; Argüello, Gustavo Alejandro; Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide; American Chemical Society; Journal of Physical Chemistry A; 113; 30; 7-2009; 8523-8528
1089-5639
1520-5215
CONICET Digital
CONICET
url http://hdl.handle.net/11336/76928
identifier_str_mv Manetti, Martin Diego; Burgos Paci, Maximiliano Alberto; Argüello, Gustavo Alejandro; Trifluoromethyl fluoroformyl trioxicarbonate, CF3OC(O)OOOC(O)F: The first nonsymmetric acyl trioxide; American Chemical Society; Journal of Physical Chemistry A; 113; 30; 7-2009; 8523-8528
1089-5639
1520-5215
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://pubs.acs.org/doi/10.1021/jp9022772
info:eu-repo/semantics/altIdentifier/doi/10.1021/jp9022772
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 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
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score 13.070432

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