Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization

Autores
Ramos Guerrero, Luis Alejandro; Ulic, Sonia Elizabeth; Romano, Rosana Mariel; Tong, Shengrui; Ge, Maofa; Vishnevskiy, Yuri V.; Berger, Raphael J.; Mitzel, Norbert W.; Beckers, Helmut; Willner, Helge; Della Vedova, Carlos Omar
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The novel molecule difluorochloroacetyl cyanide, ClF2CC(O)CN, has been characterized by IR (gas phase, Ar matrix), Raman (liquid), 19F and 13C NMR, and photoelectron (PES) spectroscopies; photoionization mass spectrometry (PIMS); and gas electron diffraction (GED). The conformational properties of ClF2CC(O)CN have been studied by joint application of vibrational spectroscopy, GED, and quantum chemical calculations. The existence of two conformers is detected in the gas and liquid phases, in which the C Cl bond adopts gauche and syn orientations with respect to the CdO group. The computed enthalpy difference is in harmony with the experimental results of the gauche being more stable than the syn conformer by ΔH = 1.3 kcal mol 1 (MP2/ccpVTZ). The valence electronic properties and the possible ionization and dissociation processes of the title compound are studied using the PES and PIMS. The experimental first vertical ionization energy of 12.0 eV corresponds to the ejection of an electron of the oxygen lone pairs. Taking into account the properties and broad applications of acyl cyanides, ClF2CC(O)CN is a promising new precursor in preparative chemistry.
Fil: Ramos Guerrero, Luis Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; Argentina
Fil: Romano, Rosana Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Tong, Shengrui. Chinese Academy of Sciences; República de China
Fil: Ge, Maofa. Chinese Academy of Sciences; República de China
Fil: Vishnevskiy, Yuri V.. Universitat Bielefeld; Alemania
Fil: Berger, Raphael J.. Universitat Bielefeld; Alemania
Fil: Mitzel, Norbert W.. Universitat Bielefeld; Alemania
Fil: Beckers, Helmut. Universität Wuppertal; Alemania
Fil: Willner, Helge. Universität Wuppertal; Alemania
Fil: Della Vedova, Carlos Omar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Materia
Vibrational spectroscopy
Gas electron diffraction
Matrix isolation
Cyanides
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:11336/280295
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/280295
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic CharacterizationRamos Guerrero, Luis AlejandroUlic, Sonia ElizabethRomano, Rosana MarielTong, ShengruiGe, MaofaVishnevskiy, Yuri V.Berger, Raphael J.Mitzel, Norbert W.Beckers, HelmutWillner, HelgeDella Vedova, Carlos OmarVibrational spectroscopyGas electron diffractionMatrix isolationCyanideshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The novel molecule difluorochloroacetyl cyanide, ClF2CC(O)CN, has been characterized by IR (gas phase, Ar matrix), Raman (liquid), 19F and 13C NMR, and photoelectron (PES) spectroscopies; photoionization mass spectrometry (PIMS); and gas electron diffraction (GED). The conformational properties of ClF2CC(O)CN have been studied by joint application of vibrational spectroscopy, GED, and quantum chemical calculations. The existence of two conformers is detected in the gas and liquid phases, in which the C Cl bond adopts gauche and syn orientations with respect to the CdO group. The computed enthalpy difference is in harmony with the experimental results of the gauche being more stable than the syn conformer by ΔH = 1.3 kcal mol 1 (MP2/ccpVTZ). The valence electronic properties and the possible ionization and dissociation processes of the title compound are studied using the PES and PIMS. The experimental first vertical ionization energy of 12.0 eV corresponds to the ejection of an electron of the oxygen lone pairs. Taking into account the properties and broad applications of acyl cyanides, ClF2CC(O)CN is a promising new precursor in preparative chemistry.Fil: Ramos Guerrero, Luis Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; ArgentinaFil: Romano, Rosana Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Tong, Shengrui. Chinese Academy of Sciences; República de ChinaFil: Ge, Maofa. Chinese Academy of Sciences; República de ChinaFil: Vishnevskiy, Yuri V.. Universitat Bielefeld; AlemaniaFil: Berger, Raphael J.. Universitat Bielefeld; AlemaniaFil: Mitzel, Norbert W.. Universitat Bielefeld; AlemaniaFil: Beckers, Helmut. Universität Wuppertal; AlemaniaFil: Willner, Helge. Universität Wuppertal; AlemaniaFil: Della Vedova, Carlos Omar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaAmerican Chemical Society2011-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/280295Ramos Guerrero, Luis Alejandro; Ulic, Sonia Elizabeth; Romano, Rosana Mariel; Tong, Shengrui; Ge, Maofa; et al.; Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization; American Chemical Society; Inorganic Chemistry; 50; 19; 9-2011; 9650-96590020-1669CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/ic201390hinfo:eu-repo/semantics/altIdentifier/doi/10.1021/ic201390hinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-02-06T12:55:10Zoai:ri.conicet.gov.ar:11336/280295instacron: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:34982026-02-06 12:55:10.58CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization
title Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization
spellingShingle Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization
Ramos Guerrero, Luis Alejandro
Vibrational spectroscopy
Gas electron diffraction
Matrix isolation
Cyanides
title_short Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization
title_full Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization
title_fullStr Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization
title_full_unstemmed Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization
title_sort Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization
dc.creator.none.fl_str_mv Ramos Guerrero, Luis Alejandro
Ulic, Sonia Elizabeth
Romano, Rosana Mariel
Tong, Shengrui
Ge, Maofa
Vishnevskiy, Yuri V.
Berger, Raphael J.
Mitzel, Norbert W.
Beckers, Helmut
Willner, Helge
Della Vedova, Carlos Omar
author Ramos Guerrero, Luis Alejandro
author_facet Ramos Guerrero, Luis Alejandro
Ulic, Sonia Elizabeth
Romano, Rosana Mariel
Tong, Shengrui
Ge, Maofa
Vishnevskiy, Yuri V.
Berger, Raphael J.
Mitzel, Norbert W.
Beckers, Helmut
Willner, Helge
Della Vedova, Carlos Omar
author_role author
author2 Ulic, Sonia Elizabeth
Romano, Rosana Mariel
Tong, Shengrui
Ge, Maofa
Vishnevskiy, Yuri V.
Berger, Raphael J.
Mitzel, Norbert W.
Beckers, Helmut
Willner, Helge
Della Vedova, Carlos Omar
author2_role author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Vibrational spectroscopy
Gas electron diffraction
Matrix isolation
Cyanides
topic Vibrational spectroscopy
Gas electron diffraction
Matrix isolation
Cyanides
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 novel molecule difluorochloroacetyl cyanide, ClF2CC(O)CN, has been characterized by IR (gas phase, Ar matrix), Raman (liquid), 19F and 13C NMR, and photoelectron (PES) spectroscopies; photoionization mass spectrometry (PIMS); and gas electron diffraction (GED). The conformational properties of ClF2CC(O)CN have been studied by joint application of vibrational spectroscopy, GED, and quantum chemical calculations. The existence of two conformers is detected in the gas and liquid phases, in which the C Cl bond adopts gauche and syn orientations with respect to the CdO group. The computed enthalpy difference is in harmony with the experimental results of the gauche being more stable than the syn conformer by ΔH = 1.3 kcal mol 1 (MP2/ccpVTZ). The valence electronic properties and the possible ionization and dissociation processes of the title compound are studied using the PES and PIMS. The experimental first vertical ionization energy of 12.0 eV corresponds to the ejection of an electron of the oxygen lone pairs. Taking into account the properties and broad applications of acyl cyanides, ClF2CC(O)CN is a promising new precursor in preparative chemistry.
Fil: Ramos Guerrero, Luis Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; Argentina
Fil: Romano, Rosana Mariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Tong, Shengrui. Chinese Academy of Sciences; República de China
Fil: Ge, Maofa. Chinese Academy of Sciences; República de China
Fil: Vishnevskiy, Yuri V.. Universitat Bielefeld; Alemania
Fil: Berger, Raphael J.. Universitat Bielefeld; Alemania
Fil: Mitzel, Norbert W.. Universitat Bielefeld; Alemania
Fil: Beckers, Helmut. Universität Wuppertal; Alemania
Fil: Willner, Helge. Universität Wuppertal; Alemania
Fil: Della Vedova, Carlos Omar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
description The novel molecule difluorochloroacetyl cyanide, ClF2CC(O)CN, has been characterized by IR (gas phase, Ar matrix), Raman (liquid), 19F and 13C NMR, and photoelectron (PES) spectroscopies; photoionization mass spectrometry (PIMS); and gas electron diffraction (GED). The conformational properties of ClF2CC(O)CN have been studied by joint application of vibrational spectroscopy, GED, and quantum chemical calculations. The existence of two conformers is detected in the gas and liquid phases, in which the C Cl bond adopts gauche and syn orientations with respect to the CdO group. The computed enthalpy difference is in harmony with the experimental results of the gauche being more stable than the syn conformer by ΔH = 1.3 kcal mol 1 (MP2/ccpVTZ). The valence electronic properties and the possible ionization and dissociation processes of the title compound are studied using the PES and PIMS. The experimental first vertical ionization energy of 12.0 eV corresponds to the ejection of an electron of the oxygen lone pairs. Taking into account the properties and broad applications of acyl cyanides, ClF2CC(O)CN is a promising new precursor in preparative chemistry.
publishDate 2011
dc.date.none.fl_str_mv 2011-09
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/11336/280295
Ramos Guerrero, Luis Alejandro; Ulic, Sonia Elizabeth; Romano, Rosana Mariel; Tong, Shengrui; Ge, Maofa; et al.; Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization; American Chemical Society; Inorganic Chemistry; 50; 19; 9-2011; 9650-9659
0020-1669
CONICET Digital
CONICET
url http://hdl.handle.net/11336/280295
identifier_str_mv Ramos Guerrero, Luis Alejandro; Ulic, Sonia Elizabeth; Romano, Rosana Mariel; Tong, Shengrui; Ge, Maofa; et al.; Chlorodifluoroacetyl Cyanide, ClF 2 CC(O)CN: Synthesis, Structure, and Spectroscopic Characterization; American Chemical Society; Inorganic Chemistry; 50; 19; 9-2011; 9650-9659
0020-1669
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/ic201390h
info:eu-repo/semantics/altIdentifier/doi/10.1021/ic201390h
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
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 13.106097

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