Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations

Autores
Gomez Zavaglia, Andrea; Kaczor, Agnieszka; Coelho, Daniela; Cristiano, M. Lurdes S.; Fausto, Rui
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
2-Allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (ABIOD) has been studied by matrix-isolation infrared spectroscopy and quantum chemical calculations. A conformational search on the B3LYP/6-311++G(3df,3pd) potential energy surface of the molecule demonstrated the existence of three conformers, Sk, Sk′ and C, with similar energies, differing in the orientation of the allyl group. The calculations predicted the Sk form as the most stable in the gaseous phase, whereas the Sk′ and C conformers have calculated relative energies of ca. 0.6 and 0.8–3.0 kJ mol−1, respectively (depending on the level of theory). In agreement with the relatively large (>6 kJ mol−1) calculated barriers for conformational interconversion, the three conformers could be efficiently trapped in an argon matrix at 10 K, the experimental infrared spectrum of the as-deposited matrix fitting well the simulated spectrum built from the calculated spectra for individual conformers scaled by their predicted populations at the temperature of the vapour of the compound prior to matrix deposition. Upon annealing the matrix at 24 K, however, both Sk and Sk′ conformers were found to convert to the more polar C conformer, indicating that this latter form becomes the most stable ABIOD conformer in the argon matrix.
Fil: Gomez Zavaglia, Andrea. Universidad de Coimbra; Portugal. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; Argentina
Fil: Kaczor, Agnieszka. Universidad de Coimbra; Portugal. Jagiellonian University; Polonia
Fil: Coelho, Daniela. Universidad de Coimbra; Portugal. Universidad de Algarve; Portugal
Fil: Cristiano, M. Lurdes S.. Universidad de Algarve; Portugal
Fil: Fausto, Rui. Universidad de Coimbra; Portugal
Materia
Saccharines
Benzisothiazoles
Molecular structure
IR spectra
Matrix isolation
Molecular orbital calculation
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:11336/155007
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculationsGomez Zavaglia, AndreaKaczor, AgnieszkaCoelho, DanielaCristiano, M. Lurdes S.Fausto, RuiSaccharinesBenzisothiazolesMolecular structureIR spectraMatrix isolationMolecular orbital calculationhttps://purl.org/becyt/ford/2.11https://purl.org/becyt/ford/22-Allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (ABIOD) has been studied by matrix-isolation infrared spectroscopy and quantum chemical calculations. A conformational search on the B3LYP/6-311++G(3df,3pd) potential energy surface of the molecule demonstrated the existence of three conformers, Sk, Sk′ and C, with similar energies, differing in the orientation of the allyl group. The calculations predicted the Sk form as the most stable in the gaseous phase, whereas the Sk′ and C conformers have calculated relative energies of ca. 0.6 and 0.8–3.0 kJ mol−1, respectively (depending on the level of theory). In agreement with the relatively large (>6 kJ mol−1) calculated barriers for conformational interconversion, the three conformers could be efficiently trapped in an argon matrix at 10 K, the experimental infrared spectrum of the as-deposited matrix fitting well the simulated spectrum built from the calculated spectra for individual conformers scaled by their predicted populations at the temperature of the vapour of the compound prior to matrix deposition. Upon annealing the matrix at 24 K, however, both Sk and Sk′ conformers were found to convert to the more polar C conformer, indicating that this latter form becomes the most stable ABIOD conformer in the argon matrix.Fil: Gomez Zavaglia, Andrea. Universidad de Coimbra; Portugal. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; ArgentinaFil: Kaczor, Agnieszka. Universidad de Coimbra; Portugal. Jagiellonian University; PoloniaFil: Coelho, Daniela. Universidad de Coimbra; Portugal. Universidad de Algarve; PortugalFil: Cristiano, M. Lurdes S.. Universidad de Algarve; PortugalFil: Fausto, Rui. Universidad de Coimbra; PortugalElsevier Science2009-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/155007Gomez Zavaglia, Andrea; Kaczor, Agnieszka; Coelho, Daniela; Cristiano, M. Lurdes S.; Fausto, Rui; Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations; Elsevier Science; Journal of Molecular Structure; 919; 1-3; 2-2009; 271-2760022-28601872-8014CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2008.09.013info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286008006182info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:09:11Zoai:ri.conicet.gov.ar:11336/155007instacron: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 10:09:11.311CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations
title Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations
spellingShingle Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations
Gomez Zavaglia, Andrea
Saccharines
Benzisothiazoles
Molecular structure
IR spectra
Matrix isolation
Molecular orbital calculation
title_short Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations
title_full Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations
title_fullStr Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations
title_full_unstemmed Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations
title_sort Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations
dc.creator.none.fl_str_mv Gomez Zavaglia, Andrea
Kaczor, Agnieszka
Coelho, Daniela
Cristiano, M. Lurdes S.
Fausto, Rui
author Gomez Zavaglia, Andrea
author_facet Gomez Zavaglia, Andrea
Kaczor, Agnieszka
Coelho, Daniela
Cristiano, M. Lurdes S.
Fausto, Rui
author_role author
author2 Kaczor, Agnieszka
Coelho, Daniela
Cristiano, M. Lurdes S.
Fausto, Rui
author2_role author
author
author
author
dc.subject.none.fl_str_mv Saccharines
Benzisothiazoles
Molecular structure
IR spectra
Matrix isolation
Molecular orbital calculation
topic Saccharines
Benzisothiazoles
Molecular structure
IR spectra
Matrix isolation
Molecular orbital calculation
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.11
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv 2-Allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (ABIOD) has been studied by matrix-isolation infrared spectroscopy and quantum chemical calculations. A conformational search on the B3LYP/6-311++G(3df,3pd) potential energy surface of the molecule demonstrated the existence of three conformers, Sk, Sk′ and C, with similar energies, differing in the orientation of the allyl group. The calculations predicted the Sk form as the most stable in the gaseous phase, whereas the Sk′ and C conformers have calculated relative energies of ca. 0.6 and 0.8–3.0 kJ mol−1, respectively (depending on the level of theory). In agreement with the relatively large (>6 kJ mol−1) calculated barriers for conformational interconversion, the three conformers could be efficiently trapped in an argon matrix at 10 K, the experimental infrared spectrum of the as-deposited matrix fitting well the simulated spectrum built from the calculated spectra for individual conformers scaled by their predicted populations at the temperature of the vapour of the compound prior to matrix deposition. Upon annealing the matrix at 24 K, however, both Sk and Sk′ conformers were found to convert to the more polar C conformer, indicating that this latter form becomes the most stable ABIOD conformer in the argon matrix.
Fil: Gomez Zavaglia, Andrea. Universidad de Coimbra; Portugal. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; Argentina
Fil: Kaczor, Agnieszka. Universidad de Coimbra; Portugal. Jagiellonian University; Polonia
Fil: Coelho, Daniela. Universidad de Coimbra; Portugal. Universidad de Algarve; Portugal
Fil: Cristiano, M. Lurdes S.. Universidad de Algarve; Portugal
Fil: Fausto, Rui. Universidad de Coimbra; Portugal
description 2-Allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (ABIOD) has been studied by matrix-isolation infrared spectroscopy and quantum chemical calculations. A conformational search on the B3LYP/6-311++G(3df,3pd) potential energy surface of the molecule demonstrated the existence of three conformers, Sk, Sk′ and C, with similar energies, differing in the orientation of the allyl group. The calculations predicted the Sk form as the most stable in the gaseous phase, whereas the Sk′ and C conformers have calculated relative energies of ca. 0.6 and 0.8–3.0 kJ mol−1, respectively (depending on the level of theory). In agreement with the relatively large (>6 kJ mol−1) calculated barriers for conformational interconversion, the three conformers could be efficiently trapped in an argon matrix at 10 K, the experimental infrared spectrum of the as-deposited matrix fitting well the simulated spectrum built from the calculated spectra for individual conformers scaled by their predicted populations at the temperature of the vapour of the compound prior to matrix deposition. Upon annealing the matrix at 24 K, however, both Sk and Sk′ conformers were found to convert to the more polar C conformer, indicating that this latter form becomes the most stable ABIOD conformer in the argon matrix.
publishDate 2009
dc.date.none.fl_str_mv 2009-02
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/11336/155007
Gomez Zavaglia, Andrea; Kaczor, Agnieszka; Coelho, Daniela; Cristiano, M. Lurdes S.; Fausto, Rui; Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations; Elsevier Science; Journal of Molecular Structure; 919; 1-3; 2-2009; 271-276
0022-2860
1872-8014
CONICET Digital
CONICET
url http://hdl.handle.net/11336/155007
identifier_str_mv Gomez Zavaglia, Andrea; Kaczor, Agnieszka; Coelho, Daniela; Cristiano, M. Lurdes S.; Fausto, Rui; Conformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculations; Elsevier Science; Journal of Molecular Structure; 919; 1-3; 2-2009; 271-276
0022-2860
1872-8014
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2008.09.013
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286008006182
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 Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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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