Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties

Autores
Torrico Vallejos, Sonia; Erben, Mauricio Federico; Boese, Roland; Della Vedova, Carlos Omar
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Pure methoxycarbonyl trifluoromethyl disulfide, CH3OC(O) SSCF3, has been prepared quantitatively by the reaction of CH 3OC(O)SCl and Hg(SCF3)2. The conformational properties of the novel molecule have been studied by vibrational spectroscopy [IR(gas) and Raman(liquid)] and quantum chemical calculations (B3LYP and MP2 methods). The gaseous compound exhibits a conformational equilibrium at room temperature where the most stable form has C1 symmetry with a synperiplanar (syn) orientation of the CO double bond with respect to the S-S disulfide bond. A second form is observed in the gaseous IR spectra corresponding to a conformer with the carbonyl bond CO in antiperiplanar (anti) position with respect to the S-S single bond. The structure of a single crystal of CH3OC(O)SSCF3 has been determined by X-ray diffraction analysis at low temperature using a miniature zone melting procedure. The crystalline solid (triclinic, P1, a = 6.4698(5) Å, b = 9.0499(8) Å, c = 12.5700(11) Å, α = 97.219(6)°, β = 93.131(5)°, γ = 96.888(5)°and Z = 4) consists exclusively of molecules with the synperiplanar conformation and the usual gauche orientation around the disulfide bond [(CS-SC) = 91.06(15)°] is adopted. The geometrical parameters agree with those obtained from quantum chemical calculations. © 2010 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Fil: Torrico Vallejos, Sonia. 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: 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: Boese, Roland. Universitat Essen; Alemania. Universität Duisburg-Essen; Alemania
Fil: Della Vedova, Carlos Omar. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Servicios a la Industria y al Sistema Científico; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina
Materia
Conformational Analysis
x-ray Diffraction
Vibrational Properties
Quantum Chemical Calculations
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:11336/151274
Acceder
id CONICETDig_e29d179a954d22518376833d59da3c1e
oai_identifier_str oai:ri.conicet.gov.ar:11336/151274
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational propertiesTorrico Vallejos, SoniaErben, Mauricio FedericoBoese, RolandDella Vedova, Carlos OmarConformational Analysisx-ray DiffractionVibrational PropertiesQuantum Chemical Calculationshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Pure methoxycarbonyl trifluoromethyl disulfide, CH3OC(O) SSCF3, has been prepared quantitatively by the reaction of CH 3OC(O)SCl and Hg(SCF3)2. The conformational properties of the novel molecule have been studied by vibrational spectroscopy [IR(gas) and Raman(liquid)] and quantum chemical calculations (B3LYP and MP2 methods). The gaseous compound exhibits a conformational equilibrium at room temperature where the most stable form has C1 symmetry with a synperiplanar (syn) orientation of the CO double bond with respect to the S-S disulfide bond. A second form is observed in the gaseous IR spectra corresponding to a conformer with the carbonyl bond CO in antiperiplanar (anti) position with respect to the S-S single bond. The structure of a single crystal of CH3OC(O)SSCF3 has been determined by X-ray diffraction analysis at low temperature using a miniature zone melting procedure. The crystalline solid (triclinic, P1, a = 6.4698(5) Å, b = 9.0499(8) Å, c = 12.5700(11) Å, α = 97.219(6)°, β = 93.131(5)°, γ = 96.888(5)°and Z = 4) consists exclusively of molecules with the synperiplanar conformation and the usual gauche orientation around the disulfide bond [(CS-SC) = 91.06(15)°] is adopted. The geometrical parameters agree with those obtained from quantum chemical calculations. © 2010 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.Fil: Torrico Vallejos, Sonia. 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: 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: Boese, Roland. Universitat Essen; Alemania. Universität Duisburg-Essen; AlemaniaFil: Della Vedova, Carlos Omar. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Servicios a la Industria y al Sistema Científico; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; ArgentinaRoyal Society of Chemistry2010-04-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/151274Torrico Vallejos, Sonia; Erben, Mauricio Federico; Boese, Roland; Della Vedova, Carlos Omar; Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties; Royal Society of Chemistry; New Journal of Chemistry; 34; 7; 9-4-2010; 1365-13721144-0546CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/B9NJ00382Ginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2010/nj/b9nj00382ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:06:50Zoai:ri.conicet.gov.ar:11336/151274instacron: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:34982025-09-03 10:06:50.786CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties
title Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties
spellingShingle Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties
Torrico Vallejos, Sonia
Conformational Analysis
x-ray Diffraction
Vibrational Properties
Quantum Chemical Calculations
title_short Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties
title_full Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties
title_fullStr Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties
title_full_unstemmed Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties
title_sort Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties
dc.creator.none.fl_str_mv Torrico Vallejos, Sonia
Erben, Mauricio Federico
Boese, Roland
Della Vedova, Carlos Omar
author Torrico Vallejos, Sonia
author_facet Torrico Vallejos, Sonia
Erben, Mauricio Federico
Boese, Roland
Della Vedova, Carlos Omar
author_role author
author2 Erben, Mauricio Federico
Boese, Roland
Della Vedova, Carlos Omar
author2_role author
author
author
dc.subject.none.fl_str_mv Conformational Analysis
x-ray Diffraction
Vibrational Properties
Quantum Chemical Calculations
topic Conformational Analysis
x-ray Diffraction
Vibrational Properties
Quantum Chemical Calculations
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Pure methoxycarbonyl trifluoromethyl disulfide, CH3OC(O) SSCF3, has been prepared quantitatively by the reaction of CH 3OC(O)SCl and Hg(SCF3)2. The conformational properties of the novel molecule have been studied by vibrational spectroscopy [IR(gas) and Raman(liquid)] and quantum chemical calculations (B3LYP and MP2 methods). The gaseous compound exhibits a conformational equilibrium at room temperature where the most stable form has C1 symmetry with a synperiplanar (syn) orientation of the CO double bond with respect to the S-S disulfide bond. A second form is observed in the gaseous IR spectra corresponding to a conformer with the carbonyl bond CO in antiperiplanar (anti) position with respect to the S-S single bond. The structure of a single crystal of CH3OC(O)SSCF3 has been determined by X-ray diffraction analysis at low temperature using a miniature zone melting procedure. The crystalline solid (triclinic, P1, a = 6.4698(5) Å, b = 9.0499(8) Å, c = 12.5700(11) Å, α = 97.219(6)°, β = 93.131(5)°, γ = 96.888(5)°and Z = 4) consists exclusively of molecules with the synperiplanar conformation and the usual gauche orientation around the disulfide bond [(CS-SC) = 91.06(15)°] is adopted. The geometrical parameters agree with those obtained from quantum chemical calculations. © 2010 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Fil: Torrico Vallejos, Sonia. 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: 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: Boese, Roland. Universitat Essen; Alemania. Universität Duisburg-Essen; Alemania
Fil: Della Vedova, Carlos Omar. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Servicios a la Industria y al Sistema Científico; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina
description Pure methoxycarbonyl trifluoromethyl disulfide, CH3OC(O) SSCF3, has been prepared quantitatively by the reaction of CH 3OC(O)SCl and Hg(SCF3)2. The conformational properties of the novel molecule have been studied by vibrational spectroscopy [IR(gas) and Raman(liquid)] and quantum chemical calculations (B3LYP and MP2 methods). The gaseous compound exhibits a conformational equilibrium at room temperature where the most stable form has C1 symmetry with a synperiplanar (syn) orientation of the CO double bond with respect to the S-S disulfide bond. A second form is observed in the gaseous IR spectra corresponding to a conformer with the carbonyl bond CO in antiperiplanar (anti) position with respect to the S-S single bond. The structure of a single crystal of CH3OC(O)SSCF3 has been determined by X-ray diffraction analysis at low temperature using a miniature zone melting procedure. The crystalline solid (triclinic, P1, a = 6.4698(5) Å, b = 9.0499(8) Å, c = 12.5700(11) Å, α = 97.219(6)°, β = 93.131(5)°, γ = 96.888(5)°and Z = 4) consists exclusively of molecules with the synperiplanar conformation and the usual gauche orientation around the disulfide bond [(CS-SC) = 91.06(15)°] is adopted. The geometrical parameters agree with those obtained from quantum chemical calculations. © 2010 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
publishDate 2010
dc.date.none.fl_str_mv 2010-04-09
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/11336/151274
Torrico Vallejos, Sonia; Erben, Mauricio Federico; Boese, Roland; Della Vedova, Carlos Omar; Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties; Royal Society of Chemistry; New Journal of Chemistry; 34; 7; 9-4-2010; 1365-1372
1144-0546
CONICET Digital
CONICET
url http://hdl.handle.net/11336/151274
identifier_str_mv Torrico Vallejos, Sonia; Erben, Mauricio Federico; Boese, Roland; Della Vedova, Carlos Omar; Methoxycarbonyl trifluoromethyl disulfide, CH3OC(O)SSCF 3: Synthesis, structure and conformational properties; Royal Society of Chemistry; New Journal of Chemistry; 34; 7; 9-4-2010; 1365-1372
1144-0546
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/B9NJ00382G
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2010/nj/b9nj00382g
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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_ 1842269977003950080
score 13.13397

Publicaciones similares