Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline

Autores
Paez Jerez, Ana Laura; Chemes, Doly María; Cutin, Edgardo Hugo; Oberhammer, Heinz; Robles, Norma Lis
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis of m-fluorosulfinylaniline together with a tentative assignment of the vibrational, NMR and mass spectra are reported. Quantum chemical calculations predict two stable conformers, with very similar energies, both of which possess in the liquid phase syn structure 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). Both conformers belong to the CS symmetry group and differ by the relative orientation of the fluorine atom and the NSO group. However, the FT-IR, FT-Raman and NMR spectra do not allow a distinction between these two conformers. The experimentally observed spectral data (FT-IR, FT-Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with the spectral data obtained by quantum chemical calculations and the gauge including atomic orbital (GIAO) method (DFT/B3LYP approximation using 6-311+G(df), 6-311++G(df,pd) and cc-pVTZ basis sets). Moreover, natural bond orbital (NBO) analysis is applied for studying the stability of the molecule upon charge delocalization in order to provide an explanation of its electronic properties.
Fil: Paez Jerez, Ana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Fil: Chemes, Doly María. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Fisica; Argentina
Fil: Cutin, Edgardo Hugo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Fil: Oberhammer, Heinz . Universität Tübingen. Institut für Physikalische und Theoretische Chemie; Alemania
Fil: Robles, Norma Lis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Materia
M-FLUOROSULFINYLANILINE
HALOGEN SUBSTITUTED SULFINYLANILINE
QUANTUM CHEMISTRY
VIBRATIONAL SPECTRA
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:11336/6688
Acceder
id CONICETDig_47cd8317aabc9506553eb0bab66edb1a
oai_identifier_str oai:ri.conicet.gov.ar:11336/6688
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, experimental and theoretical characterization of m-fluorosulfinylanilinePaez Jerez, Ana LauraChemes, Doly MaríaCutin, Edgardo HugoOberhammer, Heinz Robles, Norma LisM-FLUOROSULFINYLANILINEHALOGEN SUBSTITUTED SULFINYLANILINEQUANTUM CHEMISTRYVIBRATIONAL SPECTRAhttps://purl.org/becyt/ford/1.7https://purl.org/becyt/ford/1The synthesis of m-fluorosulfinylaniline together with a tentative assignment of the vibrational, NMR and mass spectra are reported. Quantum chemical calculations predict two stable conformers, with very similar energies, both of which possess in the liquid phase syn structure 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). Both conformers belong to the CS symmetry group and differ by the relative orientation of the fluorine atom and the NSO group. However, the FT-IR, FT-Raman and NMR spectra do not allow a distinction between these two conformers. The experimentally observed spectral data (FT-IR, FT-Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with the spectral data obtained by quantum chemical calculations and the gauge including atomic orbital (GIAO) method (DFT/B3LYP approximation using 6-311+G(df), 6-311++G(df,pd) and cc-pVTZ basis sets). Moreover, natural bond orbital (NBO) analysis is applied for studying the stability of the molecule upon charge delocalization in order to provide an explanation of its electronic properties.Fil: Paez Jerez, Ana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; ArgentinaFil: Chemes, Doly María. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Fisica; ArgentinaFil: Cutin, Edgardo Hugo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; ArgentinaFil: Oberhammer, Heinz . Universität Tübingen. Institut für Physikalische und Theoretische Chemie; AlemaniaFil: Robles, Norma Lis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; ArgentinaRoyal Society Of Chemistry2015-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6688Paez Jerez, Ana Laura; Chemes, Doly María; Cutin, Edgardo Hugo; Oberhammer, Heinz ; Robles, Norma Lis; Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline; Royal Society Of Chemistry; New Journal Of Chemistry; 39; 6; 3-2015; 4445-44511144-0546enginfo:eu-repo/semantics/altIdentifier/doi/10.1039/C5NJ00200Ainfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/NJ/c5nj00200a#!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 Técnicas2025-10-22T11:54:44Zoai:ri.conicet.gov.ar:11336/6688instacron: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 11:54:44.609CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline
title Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline
spellingShingle Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline
Paez Jerez, Ana Laura
M-FLUOROSULFINYLANILINE
HALOGEN SUBSTITUTED SULFINYLANILINE
QUANTUM CHEMISTRY
VIBRATIONAL SPECTRA
title_short Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline
title_full Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline
title_fullStr Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline
title_full_unstemmed Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline
title_sort Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline
dc.creator.none.fl_str_mv Paez Jerez, Ana Laura
Chemes, Doly María
Cutin, Edgardo Hugo
Oberhammer, Heinz
Robles, Norma Lis
author Paez Jerez, Ana Laura
author_facet Paez Jerez, Ana Laura
Chemes, Doly María
Cutin, Edgardo Hugo
Oberhammer, Heinz
Robles, Norma Lis
author_role author
author2 Chemes, Doly María
Cutin, Edgardo Hugo
Oberhammer, Heinz
Robles, Norma Lis
author2_role author
author
author
author
dc.subject.none.fl_str_mv M-FLUOROSULFINYLANILINE
HALOGEN SUBSTITUTED SULFINYLANILINE
QUANTUM CHEMISTRY
VIBRATIONAL SPECTRA
topic M-FLUOROSULFINYLANILINE
HALOGEN SUBSTITUTED SULFINYLANILINE
QUANTUM CHEMISTRY
VIBRATIONAL SPECTRA
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.7
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The synthesis of m-fluorosulfinylaniline together with a tentative assignment of the vibrational, NMR and mass spectra are reported. Quantum chemical calculations predict two stable conformers, with very similar energies, both of which possess in the liquid phase syn structure 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). Both conformers belong to the CS symmetry group and differ by the relative orientation of the fluorine atom and the NSO group. However, the FT-IR, FT-Raman and NMR spectra do not allow a distinction between these two conformers. The experimentally observed spectral data (FT-IR, FT-Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with the spectral data obtained by quantum chemical calculations and the gauge including atomic orbital (GIAO) method (DFT/B3LYP approximation using 6-311+G(df), 6-311++G(df,pd) and cc-pVTZ basis sets). Moreover, natural bond orbital (NBO) analysis is applied for studying the stability of the molecule upon charge delocalization in order to provide an explanation of its electronic properties.
Fil: Paez Jerez, Ana Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Fil: Chemes, Doly María. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Fisica; Argentina
Fil: Cutin, Edgardo Hugo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Fil: Oberhammer, Heinz . Universität Tübingen. Institut für Physikalische und Theoretische Chemie; Alemania
Fil: Robles, Norma Lis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Tucumán. Instituto de Quimica del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
description The synthesis of m-fluorosulfinylaniline together with a tentative assignment of the vibrational, NMR and mass spectra are reported. Quantum chemical calculations predict two stable conformers, with very similar energies, both of which possess in the liquid phase syn structure 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). Both conformers belong to the CS symmetry group and differ by the relative orientation of the fluorine atom and the NSO group. However, the FT-IR, FT-Raman and NMR spectra do not allow a distinction between these two conformers. The experimentally observed spectral data (FT-IR, FT-Raman, 1H and 13C and GC-mass spectrometry) of the title compound are compared with the spectral data obtained by quantum chemical calculations and the gauge including atomic orbital (GIAO) method (DFT/B3LYP approximation using 6-311+G(df), 6-311++G(df,pd) and cc-pVTZ basis sets). Moreover, natural bond orbital (NBO) analysis is applied for studying the stability of the molecule upon charge delocalization in order to provide an explanation of its electronic properties.
publishDate 2015
dc.date.none.fl_str_mv 2015-03
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/11336/6688
Paez Jerez, Ana Laura; Chemes, Doly María; Cutin, Edgardo Hugo; Oberhammer, Heinz ; Robles, Norma Lis; Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline; Royal Society Of Chemistry; New Journal Of Chemistry; 39; 6; 3-2015; 4445-4451
1144-0546
url http://hdl.handle.net/11336/6688
identifier_str_mv Paez Jerez, Ana Laura; Chemes, Doly María; Cutin, Edgardo Hugo; Oberhammer, Heinz ; Robles, Norma Lis; Synthesis, experimental and theoretical characterization of m-fluorosulfinylaniline; Royal Society Of Chemistry; New Journal Of Chemistry; 39; 6; 3-2015; 4445-4451
1144-0546
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/C5NJ00200A
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2015/NJ/c5nj00200a#!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
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 12.982451

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