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Photochemistry of 1-phenyl-tetrazolone isolated in solid argon

2006Journal article Restricted
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dc.contributor.authorGómez-Zavaglia, A.
dc.contributor.authorReva, I. D.
dc.contributor.authorFrija, L.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorFausto, R.
dc.date.accessioned2014-06-11T12:46:58Z
dc.date.available2014-06-11T12:46:58Z
dc.date.issued2006
dc.date.updated2014-06-05T10:07:16Z
dc.description.abstractThe molecular structure, vibrational spectra, tautomerism and photochemistry of the derivative of tetrazole, 1-phenyl-tetrazolone (C7H6N4O; PT) have been studied by FT-IR matrix isolation spectroscopy and DFT/B3LYP/6-311++G(d,p) calculations. Among the five structures in which PT could be expected to exist (two keto tautomers, one mesoionic olate-form and two different conformers of the hydroxyl tautomer), only the most stable species, 1-phenyl-1,4-dihydro-5H-tetrazol-5-one, could be experimentally observed in low temperature argon matrices. Monomers of this tautomer give rise to an IR spectrum that fits nicely the calculated spectrum obtained at the DFT/B3LYP/6-311++G(d,p) level of theory. In situ UV irradiation (λ > 235 nm) of the matrix-isolated PT induces three main photochemical processes, all of them involving cleavage of the tetrazole ring: e.g. (1) molecular nitrogen loss, with production of 1-phenyl-diaziridin-3-one; this compound reacts subsequently to form 1-aza-1,2,4,6-cycloheptatetraene and isocyanic acid (eventually, also to form CO plus phenyldiazene); (2) cleavage of the C(5)–N(1) and N(3)–N(4) tetrazole-ring bonds, with production of phenylazide and isocyanic acid, with phenylazide then losingN2 to yield as final product 1-aza-1,2,4,6-cycloheptatetraene; and (3) cleavage of the N(1)–N(2) and N(4)–C(5) tetrazole-ring bonds, to yield phenylisocyanate and azide. The observed photochemical processes are distinct from the preferred thermal fragmentation channel, where CO is produced together with a weak IR absorbant species.por
dc.identifier.citationGómez-Zavaglia, A.; Reva, I.D.; Frija, L.; Cristiano, M.L.; Fausto, R. Photochemistry of 1-phenyl-tetrazolone isolated in solid argon, Journal of Photochemistry and Photobiology A: Chemistry, 179, 3, 243-255, 2006.por
dc.identifier.doihttp://dx.doi.org/10.1016/j.jphotochem.2005.08.021
dc.identifier.issn1010-6030
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4265
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
dc.subject1-Phenyl-tetrazolonepor
dc.subject1-Aza-1,2,4,6-cycloheptatetraenepor
dc.subjectPhenyldiazenepor
dc.subjectPhenylisocyanatepor
dc.subjectAzidepor
dc.subjectIsocyanic acidpor
dc.subjectPhenylazidepor
dc.subject1-Phenyl-1,2-dihydrotetrazetepor
dc.subjectTetrazole-ring cleavagepor
dc.subjectMatrix isolation IR spectroscopypor
dc.subjectDFT/B3LYPpor
dc.subject6-311++G(d,p) calculationspor
dc.subjectPhotochemical fragmentationpor
dc.titlePhotochemistry of 1-phenyl-tetrazolone isolated in solid argonpor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage255por
oaire.citation.issue3por
oaire.citation.startPage243por
oaire.citation.titleJournal of Photochemistry and Photobiology A: Chemistrypor
oaire.citation.volume179por
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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