Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases
- Autores
- Arce, Valeria Beatriz; Della Vedova, Carlos Omar; Downs, Anthony J.; Parsons, Simon; Romano, Rosana Mariel
- Año de publicación
- 2006
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- The conformational properties of gaseous trichloromethyl chloroformate (or “diphosgene”), ClC(O)- OCCl3, have been studied by vibrational spectroscopy [IR (gas), IR (matrix), and Raman (liquid)] and quantum chemical calculations (MP2 and B3LYP with 6-311G* basis sets); in addition, the structure of a single crystal at low temperature has been determined by X-ray diffraction. ClC(O)OCCl3 exhibits only one conformational form having Cs symmetry with a synperiplanar orientation of the C-O single bond relative to the CdO double bond. The calculated energy difference between the syn and anti forms, 5.73 kcal mol-1 (B3LYP) or 7.06 kcal mol-1 (MP2), is consistent with the experimental findings for the gas and liquid phases. The crystalline solid at 150 K [monoclinic, P21/n, a ) 5.5578(5) Å, b ) 14.2895(12) Å, c ) 8.6246(7) Å, â ) 102.443(2)°, Z ) 4] likewise consists only of molecules in the syn form.
Fil: Arce, Valeria Beatriz. 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. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Servicios a la Industria y al Sistema Científico; Argentina
Fil: Downs, Anthony J.. University of Oxford; Reino Unido
Fil: Parsons, Simon. University of Edinburgh; Reino Unido
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 - Materia
-
DIPHOSGENE
VIBRATIONAL SPECTROSCOPY
QUANTUM CHEMICAL CALCULATIONS
SYN FORM - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/186636
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Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phasesArce, Valeria BeatrizDella Vedova, Carlos OmarDowns, Anthony J.Parsons, SimonRomano, Rosana MarielDIPHOSGENEVIBRATIONAL SPECTROSCOPYQUANTUM CHEMICAL CALCULATIONSSYN FORMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The conformational properties of gaseous trichloromethyl chloroformate (or “diphosgene”), ClC(O)- OCCl3, have been studied by vibrational spectroscopy [IR (gas), IR (matrix), and Raman (liquid)] and quantum chemical calculations (MP2 and B3LYP with 6-311G* basis sets); in addition, the structure of a single crystal at low temperature has been determined by X-ray diffraction. ClC(O)OCCl3 exhibits only one conformational form having Cs symmetry with a synperiplanar orientation of the C-O single bond relative to the CdO double bond. The calculated energy difference between the syn and anti forms, 5.73 kcal mol-1 (B3LYP) or 7.06 kcal mol-1 (MP2), is consistent with the experimental findings for the gas and liquid phases. The crystalline solid at 150 K [monoclinic, P21/n, a ) 5.5578(5) Å, b ) 14.2895(12) Å, c ) 8.6246(7) Å, â ) 102.443(2)°, Z ) 4] likewise consists only of molecules in the syn form.Fil: Arce, Valeria Beatriz. 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. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Servicios a la Industria y al Sistema Científico; ArgentinaFil: Downs, Anthony J.. University of Oxford; Reino UnidoFil: Parsons, Simon. University of Edinburgh; Reino UnidoFil: 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"; ArgentinaAmerican Chemical Society2006-12info: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/11336/186636Arce, Valeria Beatriz; Della Vedova, Carlos Omar; Downs, Anthony J.; Parsons, Simon; Romano, Rosana Mariel; Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases; American Chemical Society; Journal of Organic Chemistry; 71; 9; 12-2006; 3423-34280022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jo052260ainfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo052260ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:20:59Zoai:ri.conicet.gov.ar:11336/186636instacron: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 10:20:59.599CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases |
title |
Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases |
spellingShingle |
Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases Arce, Valeria Beatriz DIPHOSGENE VIBRATIONAL SPECTROSCOPY QUANTUM CHEMICAL CALCULATIONS SYN FORM |
title_short |
Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases |
title_full |
Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases |
title_fullStr |
Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases |
title_full_unstemmed |
Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases |
title_sort |
Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases |
dc.creator.none.fl_str_mv |
Arce, Valeria Beatriz Della Vedova, Carlos Omar Downs, Anthony J. Parsons, Simon Romano, Rosana Mariel |
author |
Arce, Valeria Beatriz |
author_facet |
Arce, Valeria Beatriz Della Vedova, Carlos Omar Downs, Anthony J. Parsons, Simon Romano, Rosana Mariel |
author_role |
author |
author2 |
Della Vedova, Carlos Omar Downs, Anthony J. Parsons, Simon Romano, Rosana Mariel |
author2_role |
author author author author |
dc.subject.none.fl_str_mv |
DIPHOSGENE VIBRATIONAL SPECTROSCOPY QUANTUM CHEMICAL CALCULATIONS SYN FORM |
topic |
DIPHOSGENE VIBRATIONAL SPECTROSCOPY QUANTUM CHEMICAL CALCULATIONS SYN FORM |
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 conformational properties of gaseous trichloromethyl chloroformate (or “diphosgene”), ClC(O)- OCCl3, have been studied by vibrational spectroscopy [IR (gas), IR (matrix), and Raman (liquid)] and quantum chemical calculations (MP2 and B3LYP with 6-311G* basis sets); in addition, the structure of a single crystal at low temperature has been determined by X-ray diffraction. ClC(O)OCCl3 exhibits only one conformational form having Cs symmetry with a synperiplanar orientation of the C-O single bond relative to the CdO double bond. The calculated energy difference between the syn and anti forms, 5.73 kcal mol-1 (B3LYP) or 7.06 kcal mol-1 (MP2), is consistent with the experimental findings for the gas and liquid phases. The crystalline solid at 150 K [monoclinic, P21/n, a ) 5.5578(5) Å, b ) 14.2895(12) Å, c ) 8.6246(7) Å, â ) 102.443(2)°, Z ) 4] likewise consists only of molecules in the syn form. Fil: Arce, Valeria Beatriz. 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. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Servicios a la Industria y al Sistema Científico; Argentina Fil: Downs, Anthony J.. University of Oxford; Reino Unido Fil: Parsons, Simon. University of Edinburgh; Reino Unido 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 |
description |
The conformational properties of gaseous trichloromethyl chloroformate (or “diphosgene”), ClC(O)- OCCl3, have been studied by vibrational spectroscopy [IR (gas), IR (matrix), and Raman (liquid)] and quantum chemical calculations (MP2 and B3LYP with 6-311G* basis sets); in addition, the structure of a single crystal at low temperature has been determined by X-ray diffraction. ClC(O)OCCl3 exhibits only one conformational form having Cs symmetry with a synperiplanar orientation of the C-O single bond relative to the CdO double bond. The calculated energy difference between the syn and anti forms, 5.73 kcal mol-1 (B3LYP) or 7.06 kcal mol-1 (MP2), is consistent with the experimental findings for the gas and liquid phases. The crystalline solid at 150 K [monoclinic, P21/n, a ) 5.5578(5) Å, b ) 14.2895(12) Å, c ) 8.6246(7) Å, â ) 102.443(2)°, Z ) 4] likewise consists only of molecules in the syn form. |
publishDate |
2006 |
dc.date.none.fl_str_mv |
2006-12 |
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/11336/186636 Arce, Valeria Beatriz; Della Vedova, Carlos Omar; Downs, Anthony J.; Parsons, Simon; Romano, Rosana Mariel; Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases; American Chemical Society; Journal of Organic Chemistry; 71; 9; 12-2006; 3423-3428 0022-3263 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/186636 |
identifier_str_mv |
Arce, Valeria Beatriz; Della Vedova, Carlos Omar; Downs, Anthony J.; Parsons, Simon; Romano, Rosana Mariel; Trichloromethyl chloroformate ("diphosgene"), ClC(O)OCCl 3: Structure and conformational properties in the gaseous and condensed phases; American Chemical Society; Journal of Organic Chemistry; 71; 9; 12-2006; 3423-3428 0022-3263 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/jo052260a info:eu-repo/semantics/altIdentifier/doi/10.1021/jo052260a |
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 |
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CONICET Digital (CONICET) |
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CONICET Digital (CONICET) |
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Consejo Nacional de Investigaciones Científicas y Técnicas |
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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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1844614195339853824 |
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13.070432 |