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Thermally induced sigmatropic isomerization of pseudosaccharyl allylic ether

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dc.contributor.authorGómez-Zavaglia, A.
dc.contributor.authorKaczor, A.
dc.contributor.authorAlmeida, R.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorEusébio, M. E. S.
dc.contributor.authorMaria, T. M. R.
dc.contributor.authorMobili, P.
dc.contributor.authorFausto, R.
dc.date.accessioned2014-06-06T18:27:46Z
dc.date.available2014-06-06T18:27:46Z
dc.date.issued2009
dc.date.updated2014-06-05T11:11:29Z
dc.description.abstractThe thermally induced sigmatropic isomerization of the pseudosaccharyl allylic ether [3-(allyloxy)-1,2-benzisothiazole 1,1-dioxide; ABID] has been investigated by a multidisciplinary approach using temperature dependent infrared spectroscopy, differential scanning calorimetry, and polarized light thermomicroscopy, complemented by theoretical methods. Migration of the allylic system from O to N occurs in the melted ABID, and the thermally obtained 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (ABIOD) starts to be produced at ca. 150 °C, in a process with an activation energy of ∼92 kJ mol-1. From kinetic data, a concerted [3,3′] sigmatropic mechanism is proposed. In the temperature range investigated, ABIOD was found to exhibit polymorphism. Cooling of the molten compound leads to the production of a metastable crystalline form, which upon annealing at room temperature might be transformed to the stable crystalline phase. ABID shows a single crystalline variety. Assignments were proposed for the infrared spectra of the observed neat condensed phases of the two compounds.por
dc.identifier.citationGo¿?mez-Zavaglia, A.; Kaczor, A.; Almeida, R.; Cristiano, M. L. S.; Euse¿?bio, M. E. S.; Maria, T. M. R.; Mobili, P.; Fausto, R. Thermally Induced Sigmatropic Isomerization of Pseudosaccharyl Allylic Ether, The Journal of Physical Chemistry A, 113, 15, 3517-3522, 2009.por
dc.identifier.issn1089-5639
dc.identifier.otherAUT: MCR00716
dc.identifier.urihttp://hdl.handle.net/10400.1/4240
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherAmerican Chemical Societypor
dc.titleThermally induced sigmatropic isomerization of pseudosaccharyl allylic etherpor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage3522por
oaire.citation.issue15por
oaire.citation.startPage3517por
oaire.citation.titleThe Journal of Physical Chemistry Apor
oaire.citation.volume113por
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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