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dc.contributor.author
Gomez Zavaglia, Andrea
dc.contributor.author
Kaczor, Agnieszka
dc.contributor.author
Coelho, Daniela
dc.contributor.author
Cristiano, M. Lurdes S.
dc.contributor.author
Fausto, Rui
dc.date.available
2022-04-12T11:57:26Z
dc.date.issued
2009-02
dc.identifier.citation
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
dc.identifier.issn
0022-2860
dc.identifier.uri
http://hdl.handle.net/11336/155007
dc.description.abstract
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.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Saccharines
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Benzisothiazoles
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Molecular structure
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IR spectra
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Matrix isolation
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Molecular orbital calculation
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Alimentos y Bebidas
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Otras Ingenierías y Tecnologías
dc.subject.classification
INGENIERÍAS Y TECNOLOGÍAS
dc.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
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2022-03-14T16:42:25Z
dc.identifier.eissn
1872-8014
dc.journal.volume
919
dc.journal.number
1-3
dc.journal.pagination
271-276
dc.journal.pais
Países Bajos
dc.journal.ciudad
Amsterdam
dc.description.fil
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
dc.description.fil
Fil: Kaczor, Agnieszka. Universidad de Coimbra; Portugal. Jagiellonian University; Polonia
dc.description.fil
Fil: Coelho, Daniela. Universidad de Coimbra; Portugal. Universidad de Algarve; Portugal
dc.description.fil
Fil: Cristiano, M. Lurdes S.. Universidad de Algarve; Portugal
dc.description.fil
Fil: Fausto, Rui. Universidad de Coimbra; Portugal
dc.journal.title
Journal of Molecular Structure
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1016/j.molstruc.2008.09.013
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0022286008006182
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