Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis

Autores
Rodriguez Pirani, Lucas Sebastian; Erben, Mauricio Federico; Boese, Roland; Pozzi, Carlos Gustavo; Fantoni, Adolfo Carlos; Della Vedova, Carlos Omar
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The molecular structure of ethyl chlorothioformate, ClC(O)SCH2CH3, has been investigated in the solid phase by X-ray diffraction analysis at low temperature using a miniature zone-melting procedure and IR laser radiation. The crystalline solid consists exclusively of molecules with thesynperiplanar conformation with respect to the CO double bond and the SC single bond, and gauche orientation of the ethyl group (syn-gauche). These results coincide with previous studies devoted to gas-phase conformational properties. The conformational preference for the  ClC(O)SY (Y = Cl, CF3, CH3 and CH2CH3) series of molecules was rationalized using the natural bond orbital (NBO) scheme. It was found that both resonance (mesomeric) and anomeric (hyperconjugation) intermolecular charge-transfer interactions are important for describing the syn/anti equilibrium, also illustrating the effect of electronegativity of the substituent in the  conformation preference of the ClC(O)S moiety. On the basis of the atoms in molecules (AIM) theory, intermolecular interactions have been characterized in the B3LYP/6-31G** periodic  boundary electron density.
Fil: Rodriguez Pirani, Lucas Sebastian. 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
Fil: Pozzi, Carlos Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; 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
Materia
X-ray
conformation
sulfenyl carbonyl compounds
AIM
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:11336/278199
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/278199
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysisRodriguez Pirani, Lucas SebastianErben, Mauricio FedericoBoese, RolandPozzi, Carlos GustavoFantoni, Adolfo CarlosDella Vedova, Carlos OmarX-rayconformationsulfenyl carbonyl compoundsAIMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The molecular structure of ethyl chlorothioformate, ClC(O)SCH2CH3, has been investigated in the solid phase by X-ray diffraction analysis at low temperature using a miniature zone-melting procedure and IR laser radiation. The crystalline solid consists exclusively of molecules with thesynperiplanar conformation with respect to the CO double bond and the SC single bond, and gauche orientation of the ethyl group (syn-gauche). These results coincide with previous studies devoted to gas-phase conformational properties. The conformational preference for the  ClC(O)SY (Y = Cl, CF3, CH3 and CH2CH3) series of molecules was rationalized using the natural bond orbital (NBO) scheme. It was found that both resonance (mesomeric) and anomeric (hyperconjugation) intermolecular charge-transfer interactions are important for describing the syn/anti equilibrium, also illustrating the effect of electronegativity of the substituent in the  conformation preference of the ClC(O)S moiety. On the basis of the atoms in molecules (AIM) theory, intermolecular interactions have been characterized in the B3LYP/6-31G** periodic  boundary electron density.Fil: Rodriguez Pirani, Lucas Sebastian. 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; AlemaniaFil: Pozzi, Carlos Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; 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"; ArgentinaWiley Blackwell Publishing, Inc2011-07info: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/11336/278199Rodriguez Pirani, Lucas Sebastian; Erben, Mauricio Federico; Boese, Roland; Pozzi, Carlos Gustavo; Fantoni, Adolfo Carlos; et al.; Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section B-Structural Science; 67; 4; 7-2011; 350-3560108-7681CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/iucr/doi/10.1107/S0108768111017575info:eu-repo/semantics/altIdentifier/doi/10.1107/S0108768111017575info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-04-15T10:08:27Zoai:ri.conicet.gov.ar:11336/278199instacron: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:34982026-04-15 10:08:28.245CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis
title Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis
spellingShingle Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis
Rodriguez Pirani, Lucas Sebastian
X-ray
conformation
sulfenyl carbonyl compounds
AIM
title_short Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis
title_full Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis
title_fullStr Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis
title_full_unstemmed Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis
title_sort Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis
dc.creator.none.fl_str_mv Rodriguez Pirani, Lucas Sebastian
Erben, Mauricio Federico
Boese, Roland
Pozzi, Carlos Gustavo
Fantoni, Adolfo Carlos
Della Vedova, Carlos Omar
author Rodriguez Pirani, Lucas Sebastian
author_facet Rodriguez Pirani, Lucas Sebastian
Erben, Mauricio Federico
Boese, Roland
Pozzi, Carlos Gustavo
Fantoni, Adolfo Carlos
Della Vedova, Carlos Omar
author_role author
author2 Erben, Mauricio Federico
Boese, Roland
Pozzi, Carlos Gustavo
Fantoni, Adolfo Carlos
Della Vedova, Carlos Omar
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv X-ray
conformation
sulfenyl carbonyl compounds
AIM
topic X-ray
conformation
sulfenyl carbonyl compounds
AIM
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 molecular structure of ethyl chlorothioformate, ClC(O)SCH2CH3, has been investigated in the solid phase by X-ray diffraction analysis at low temperature using a miniature zone-melting procedure and IR laser radiation. The crystalline solid consists exclusively of molecules with thesynperiplanar conformation with respect to the CO double bond and the SC single bond, and gauche orientation of the ethyl group (syn-gauche). These results coincide with previous studies devoted to gas-phase conformational properties. The conformational preference for the  ClC(O)SY (Y = Cl, CF3, CH3 and CH2CH3) series of molecules was rationalized using the natural bond orbital (NBO) scheme. It was found that both resonance (mesomeric) and anomeric (hyperconjugation) intermolecular charge-transfer interactions are important for describing the syn/anti equilibrium, also illustrating the effect of electronegativity of the substituent in the  conformation preference of the ClC(O)S moiety. On the basis of the atoms in molecules (AIM) theory, intermolecular interactions have been characterized in the B3LYP/6-31G** periodic  boundary electron density.
Fil: Rodriguez Pirani, Lucas Sebastian. 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
Fil: Pozzi, Carlos Gustavo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Fantoni, Adolfo Carlos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; 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
description The molecular structure of ethyl chlorothioformate, ClC(O)SCH2CH3, has been investigated in the solid phase by X-ray diffraction analysis at low temperature using a miniature zone-melting procedure and IR laser radiation. The crystalline solid consists exclusively of molecules with thesynperiplanar conformation with respect to the CO double bond and the SC single bond, and gauche orientation of the ethyl group (syn-gauche). These results coincide with previous studies devoted to gas-phase conformational properties. The conformational preference for the  ClC(O)SY (Y = Cl, CF3, CH3 and CH2CH3) series of molecules was rationalized using the natural bond orbital (NBO) scheme. It was found that both resonance (mesomeric) and anomeric (hyperconjugation) intermolecular charge-transfer interactions are important for describing the syn/anti equilibrium, also illustrating the effect of electronegativity of the substituent in the  conformation preference of the ClC(O)S moiety. On the basis of the atoms in molecules (AIM) theory, intermolecular interactions have been characterized in the B3LYP/6-31G** periodic  boundary electron density.
publishDate 2011
dc.date.none.fl_str_mv 2011-07
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/11336/278199
Rodriguez Pirani, Lucas Sebastian; Erben, Mauricio Federico; Boese, Roland; Pozzi, Carlos Gustavo; Fantoni, Adolfo Carlos; et al.; Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section B-Structural Science; 67; 4; 7-2011; 350-356
0108-7681
CONICET Digital
CONICET
url http://hdl.handle.net/11336/278199
identifier_str_mv Rodriguez Pirani, Lucas Sebastian; Erben, Mauricio Federico; Boese, Roland; Pozzi, Carlos Gustavo; Fantoni, Adolfo Carlos; et al.; Conformational preference of chlorothioformate species: molecular structure of ethyl chlorothioformate, ClC(O)SCH 2 CH 3 , in the solid phase and NBO analysis; Wiley Blackwell Publishing, Inc; Acta Crystallographica Section B-Structural Science; 67; 4; 7-2011; 350-356
0108-7681
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://onlinelibrary.wiley.com/iucr/doi/10.1107/S0108768111017575
info:eu-repo/semantics/altIdentifier/doi/10.1107/S0108768111017575
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 Wiley Blackwell Publishing, Inc
publisher.none.fl_str_mv Wiley Blackwell Publishing, Inc
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 13.203462

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