Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series

Autores
Paez Jerez, Ana Laura; Alonso de Armiño, Diego Javier; Robles, Norma Lis
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis of o-fluorosulfinylaniline is reported with the aim to complete the fluorinated sulfinylaniline series. The FT-IR and Raman spectra of o-fluorosulfinylaniline are recorded and the fundamental modes of its vibrational frequencies are assigned together with a tentative assignment of the NMR and mass spectra. Quantum chemical calculations on the optimized geometry predict in the liquid phase a planar structure with syn orientation of the –N[double bond, length as m-dash]S[double bond, length as m-dash]O moiety (syn of the S[double bond, length as m-dash]O double bond relative to the C–N single bond), which belongs to the CS symmetry group. The experimentally observed spectral data (FT-IR, Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with those obtained theoretically from DFT calculations and the gauge including atomic orbital (GIAO) method. Vibrational frequencies were assigned with the aid of anharmonic variational methods (VSCF) obtaining a significantly better agreement with experiment than with simple harmonic oscillator methods. Moreover, stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital (NBO) analysis.
Fil: Paez Jerez, Ana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Alonso de Armiño, Diego Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto Superior de Investigaciones Biológicas. Universidad Nacional de Tucumán. Instituto Superior de Investigaciones Biológicas; Argentina
Fil: Robles, Norma Lis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Materia
o-FLUOROSULFINYLANILINE
SYNTHESIS
VIBRATIONAL SPECTROSCOPY
SUBSTITUENT INFLUENCE
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:11336/43672
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/43672
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network_name_str CONICET Digital (CONICET)
spelling Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline seriesPaez Jerez, Ana LauraAlonso de Armiño, Diego JavierRobles, Norma Liso-FLUOROSULFINYLANILINESYNTHESISVIBRATIONAL SPECTROSCOPYSUBSTITUENT INFLUENCEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis of o-fluorosulfinylaniline is reported with the aim to complete the fluorinated sulfinylaniline series. The FT-IR and Raman spectra of o-fluorosulfinylaniline are recorded and the fundamental modes of its vibrational frequencies are assigned together with a tentative assignment of the NMR and mass spectra. Quantum chemical calculations on the optimized geometry predict in the liquid phase a planar structure with syn orientation of the –N[double bond, length as m-dash]S[double bond, length as m-dash]O moiety (syn of the S[double bond, length as m-dash]O double bond relative to the C–N single bond), which belongs to the CS symmetry group. The experimentally observed spectral data (FT-IR, Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with those obtained theoretically from DFT calculations and the gauge including atomic orbital (GIAO) method. Vibrational frequencies were assigned with the aid of anharmonic variational methods (VSCF) obtaining a significantly better agreement with experiment than with simple harmonic oscillator methods. Moreover, stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital (NBO) analysis.Fil: Paez Jerez, Ana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Alonso de Armiño, Diego Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto Superior de Investigaciones Biológicas. Universidad Nacional de Tucumán. Instituto Superior de Investigaciones Biológicas; ArgentinaFil: Robles, Norma Lis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaRoyal Society of Chemistry2015-10info: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/11336/43672Paez Jerez, Ana Laura; Alonso de Armiño, Diego Javier; Robles, Norma Lis; Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series; Royal Society of Chemistry; New Journal of Chemistry; 39; 12; 10-2015; 9894-99021144-0546CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/C5NJ02252Einfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/NJ/C5NJ02252E#!divAbstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:57:10Zoai:ri.conicet.gov.ar:11336/43672instacron: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 09:57:10.769CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series
title Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series
spellingShingle Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series
Paez Jerez, Ana Laura
o-FLUOROSULFINYLANILINE
SYNTHESIS
VIBRATIONAL SPECTROSCOPY
SUBSTITUENT INFLUENCE
title_short Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series
title_full Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series
title_fullStr Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series
title_full_unstemmed Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series
title_sort Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series
dc.creator.none.fl_str_mv Paez Jerez, Ana Laura
Alonso de Armiño, Diego Javier
Robles, Norma Lis
author Paez Jerez, Ana Laura
author_facet Paez Jerez, Ana Laura
Alonso de Armiño, Diego Javier
Robles, Norma Lis
author_role author
author2 Alonso de Armiño, Diego Javier
Robles, Norma Lis
author2_role author
author
dc.subject.none.fl_str_mv o-FLUOROSULFINYLANILINE
SYNTHESIS
VIBRATIONAL SPECTROSCOPY
SUBSTITUENT INFLUENCE
topic o-FLUOROSULFINYLANILINE
SYNTHESIS
VIBRATIONAL SPECTROSCOPY
SUBSTITUENT INFLUENCE
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 synthesis of o-fluorosulfinylaniline is reported with the aim to complete the fluorinated sulfinylaniline series. The FT-IR and Raman spectra of o-fluorosulfinylaniline are recorded and the fundamental modes of its vibrational frequencies are assigned together with a tentative assignment of the NMR and mass spectra. Quantum chemical calculations on the optimized geometry predict in the liquid phase a planar structure with syn orientation of the –N[double bond, length as m-dash]S[double bond, length as m-dash]O moiety (syn of the S[double bond, length as m-dash]O double bond relative to the C–N single bond), which belongs to the CS symmetry group. The experimentally observed spectral data (FT-IR, Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with those obtained theoretically from DFT calculations and the gauge including atomic orbital (GIAO) method. Vibrational frequencies were assigned with the aid of anharmonic variational methods (VSCF) obtaining a significantly better agreement with experiment than with simple harmonic oscillator methods. Moreover, stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital (NBO) analysis.
Fil: Paez Jerez, Ana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Alonso de Armiño, Diego Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto Superior de Investigaciones Biológicas. Universidad Nacional de Tucumán. Instituto Superior de Investigaciones Biológicas; Argentina
Fil: Robles, Norma Lis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
description The synthesis of o-fluorosulfinylaniline is reported with the aim to complete the fluorinated sulfinylaniline series. The FT-IR and Raman spectra of o-fluorosulfinylaniline are recorded and the fundamental modes of its vibrational frequencies are assigned together with a tentative assignment of the NMR and mass spectra. Quantum chemical calculations on the optimized geometry predict in the liquid phase a planar structure with syn orientation of the –N[double bond, length as m-dash]S[double bond, length as m-dash]O moiety (syn of the S[double bond, length as m-dash]O double bond relative to the C–N single bond), which belongs to the CS symmetry group. The experimentally observed spectral data (FT-IR, Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with those obtained theoretically from DFT calculations and the gauge including atomic orbital (GIAO) method. Vibrational frequencies were assigned with the aid of anharmonic variational methods (VSCF) obtaining a significantly better agreement with experiment than with simple harmonic oscillator methods. Moreover, stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital (NBO) analysis.
publishDate 2015
dc.date.none.fl_str_mv 2015-10
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/11336/43672
Paez Jerez, Ana Laura; Alonso de Armiño, Diego Javier; Robles, Norma Lis; Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series; Royal Society of Chemistry; New Journal of Chemistry; 39; 12; 10-2015; 9894-9902
1144-0546
CONICET Digital
CONICET
url http://hdl.handle.net/11336/43672
identifier_str_mv Paez Jerez, Ana Laura; Alonso de Armiño, Diego Javier; Robles, Norma Lis; Synthesis and characterization of o-fluorosulfinylaniline: A comparative vibrational study of fluorinated sulfinylaniline series; Royal Society of Chemistry; New Journal of Chemistry; 39; 12; 10-2015; 9894-9902
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/C5NJ02252E
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/NJ/C5NJ02252E#!divAbstract
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 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
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score 13.070432

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