Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods

Autores
Erben, Mauricio Federico; Della Vedova, Carlos Omar; Boese, Roland; Willner, Helge; Oberhammer, Heinz
Año de publicación
2004
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The gas phase conformational properties and geometric structure of trifluoromethyl chloroformate, CIC(O)-OCF3, have been studied by vibrational spectroscopy (IR (gas), IR (matrix), and Raman (liquid)), gas electron diffraction (GED), and quantum chemical calculation (HF, B3LYP and MP2 methods with 6-311G* basis sets). The molecule exhibits only one form having Cs symmetry with synperiplanar orientation of the O-C single bond relative to the C=O double bond. If heated Ar:CIC(O)OCF3 mixtures are deposited as a matrix at 14 K, bands appear in the IR spectra which are assigned to the anti form. At room temperature, the contribution of the anti rotamer is estimated to be less than 1%. This high energy conformer is not observed in the GED experiment. The structure of solid CIC(O)OCF3 was determined by X-ray diffraction analysis from crystals obtained at low temperature, using a miniature zone melting procedure. The molecule crystallizes forming a dimeric structure belonging to the monoclinic crystal system and adopts the P21/n spatial group. Furthermore, we report the structure of the similar molecule trifluoroacetyl chloride. CF3C(O)Cl, in its crystalline phase by using the same method.
Fil: Erben, Mauricio Federico. 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: 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. Universidad Nacional de La Plata; Argentina
Fil: Boese, Roland. Universitat Essen; Alemania
Fil: Willner, Helge. Universitat Essen; Alemania. Bergische Universität Wuppertal; Alemania
Fil: Oberhammer, Heinz. Eberhard Karls Universität Tübingen; Alemania
Materia
ClC(O)OCF3
Theoretical Methods
Trifluoromethyl Chloroformate
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:11336/192606
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/192606
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methodsErben, Mauricio FedericoDella Vedova, Carlos OmarBoese, RolandWillner, HelgeOberhammer, HeinzClC(O)OCF3Theoretical MethodsTrifluoromethyl Chloroformatehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The gas phase conformational properties and geometric structure of trifluoromethyl chloroformate, CIC(O)-OCF3, have been studied by vibrational spectroscopy (IR (gas), IR (matrix), and Raman (liquid)), gas electron diffraction (GED), and quantum chemical calculation (HF, B3LYP and MP2 methods with 6-311G* basis sets). The molecule exhibits only one form having Cs symmetry with synperiplanar orientation of the O-C single bond relative to the C=O double bond. If heated Ar:CIC(O)OCF3 mixtures are deposited as a matrix at 14 K, bands appear in the IR spectra which are assigned to the anti form. At room temperature, the contribution of the anti rotamer is estimated to be less than 1%. This high energy conformer is not observed in the GED experiment. The structure of solid CIC(O)OCF3 was determined by X-ray diffraction analysis from crystals obtained at low temperature, using a miniature zone melting procedure. The molecule crystallizes forming a dimeric structure belonging to the monoclinic crystal system and adopts the P21/n spatial group. Furthermore, we report the structure of the similar molecule trifluoroacetyl chloride. CF3C(O)Cl, in its crystalline phase by using the same method.Fil: Erben, Mauricio Federico. 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: 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. Universidad Nacional de La Plata; ArgentinaFil: Boese, Roland. Universitat Essen; AlemaniaFil: Willner, Helge. Universitat Essen; Alemania. Bergische Universität Wuppertal; AlemaniaFil: Oberhammer, Heinz. Eberhard Karls Universität Tübingen; AlemaniaAmerican Chemical Society2004-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/192606Erben, Mauricio Federico; Della Vedova, Carlos Omar; Boese, Roland; Willner, Helge; Oberhammer, Heinz; Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods; American Chemical Society; Journal of Physical Chemistry A; 108; 4; 12-2004; 699-7061089-5639CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/jp036966pinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp036966pinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:03:35Zoai:ri.conicet.gov.ar:11336/192606instacron: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:34982025-10-22 11:03:35.416CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods
title Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods
spellingShingle Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods
Erben, Mauricio Federico
ClC(O)OCF3
Theoretical Methods
Trifluoromethyl Chloroformate
title_short Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods
title_full Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods
title_fullStr Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods
title_full_unstemmed Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods
title_sort Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods
dc.creator.none.fl_str_mv Erben, Mauricio Federico
Della Vedova, Carlos Omar
Boese, Roland
Willner, Helge
Oberhammer, Heinz
author Erben, Mauricio Federico
author_facet Erben, Mauricio Federico
Della Vedova, Carlos Omar
Boese, Roland
Willner, Helge
Oberhammer, Heinz
author_role author
author2 Della Vedova, Carlos Omar
Boese, Roland
Willner, Helge
Oberhammer, Heinz
author2_role author
author
author
author
dc.subject.none.fl_str_mv ClC(O)OCF3
Theoretical Methods
Trifluoromethyl Chloroformate
topic ClC(O)OCF3
Theoretical Methods
Trifluoromethyl Chloroformate
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 gas phase conformational properties and geometric structure of trifluoromethyl chloroformate, CIC(O)-OCF3, have been studied by vibrational spectroscopy (IR (gas), IR (matrix), and Raman (liquid)), gas electron diffraction (GED), and quantum chemical calculation (HF, B3LYP and MP2 methods with 6-311G* basis sets). The molecule exhibits only one form having Cs symmetry with synperiplanar orientation of the O-C single bond relative to the C=O double bond. If heated Ar:CIC(O)OCF3 mixtures are deposited as a matrix at 14 K, bands appear in the IR spectra which are assigned to the anti form. At room temperature, the contribution of the anti rotamer is estimated to be less than 1%. This high energy conformer is not observed in the GED experiment. The structure of solid CIC(O)OCF3 was determined by X-ray diffraction analysis from crystals obtained at low temperature, using a miniature zone melting procedure. The molecule crystallizes forming a dimeric structure belonging to the monoclinic crystal system and adopts the P21/n spatial group. Furthermore, we report the structure of the similar molecule trifluoroacetyl chloride. CF3C(O)Cl, in its crystalline phase by using the same method.
Fil: Erben, Mauricio Federico. 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: 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. Universidad Nacional de La Plata; Argentina
Fil: Boese, Roland. Universitat Essen; Alemania
Fil: Willner, Helge. Universitat Essen; Alemania. Bergische Universität Wuppertal; Alemania
Fil: Oberhammer, Heinz. Eberhard Karls Universität Tübingen; Alemania
description The gas phase conformational properties and geometric structure of trifluoromethyl chloroformate, CIC(O)-OCF3, have been studied by vibrational spectroscopy (IR (gas), IR (matrix), and Raman (liquid)), gas electron diffraction (GED), and quantum chemical calculation (HF, B3LYP and MP2 methods with 6-311G* basis sets). The molecule exhibits only one form having Cs symmetry with synperiplanar orientation of the O-C single bond relative to the C=O double bond. If heated Ar:CIC(O)OCF3 mixtures are deposited as a matrix at 14 K, bands appear in the IR spectra which are assigned to the anti form. At room temperature, the contribution of the anti rotamer is estimated to be less than 1%. This high energy conformer is not observed in the GED experiment. The structure of solid CIC(O)OCF3 was determined by X-ray diffraction analysis from crystals obtained at low temperature, using a miniature zone melting procedure. The molecule crystallizes forming a dimeric structure belonging to the monoclinic crystal system and adopts the P21/n spatial group. Furthermore, we report the structure of the similar molecule trifluoroacetyl chloride. CF3C(O)Cl, in its crystalline phase by using the same method.
publishDate 2004
dc.date.none.fl_str_mv 2004-12
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/11336/192606
Erben, Mauricio Federico; Della Vedova, Carlos Omar; Boese, Roland; Willner, Helge; Oberhammer, Heinz; Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods; American Chemical Society; Journal of Physical Chemistry A; 108; 4; 12-2004; 699-706
1089-5639
CONICET Digital
CONICET
url http://hdl.handle.net/11336/192606
identifier_str_mv Erben, Mauricio Federico; Della Vedova, Carlos Omar; Boese, Roland; Willner, Helge; Oberhammer, Heinz; Trifluoromethyl chloroformate, CIC(O)OCF3: Structure, conformation, and vibrational analysis studied by experimental and theoretical methods; American Chemical Society; Journal of Physical Chemistry A; 108; 4; 12-2004; 699-706
1089-5639
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/jp036966p
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp036966p
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
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 12.982451

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