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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

2009Journal article Restricted access
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dc.contributor.authorGómez-Zavaglia, A.
dc.contributor.authorKaczor, A.
dc.contributor.authorCoelho, Daniela
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorFausto, R.
dc.date.accessioned2014-06-11T12:22:12Z
dc.date.available2014-06-11T12:22:12Z
dc.date.issued2009
dc.date.updated2014-06-05T11:00:20Z
dc.description.abstract2-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, Sk0 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 Sk0 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 Sk0 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.por
dc.identifier.citationGómez-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, Journal of Molecular Structure, 919, 1-3, 271-276, 2009.por
dc.identifier.doihttp://dx.doi.org/10.1016/j.molstruc.2008.09.013
dc.identifier.issn0022-2860
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4263
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
dc.subjectBenzisothiazolespor
dc.subjectMolecular structurepor
dc.subjectIR spectrapor
dc.subjectMatrix isolationpor
dc.subjectMolecular orbital calculationspor
dc.titleConformational and structural analysis of 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide as probed by matrix-isolation spectroscopy and quantum chemical calculationspor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage276por
oaire.citation.issue1-3por
oaire.citation.startPage271por
oaire.citation.titleJournal of Molecular Structurepor
oaire.citation.volume919por
person.familyNameCristiano
person.givenNameMaria de Lurdes
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id9238724800
rcaap.rightsrestrictedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublicationb16751a6-748e-44b0-9c59-058cbd5b2cc3
relation.isAuthorOfPublication.latestForDiscoveryb16751a6-748e-44b0-9c59-058cbd5b2cc3

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