Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/17911
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dc.contributor.authorGómez-Zavaglia, A.-
dc.contributor.authorReva, I.D.-
dc.contributor.authorFrija, L.-
dc.contributor.authorCristiano, M. L.-
dc.contributor.authorFausto, R.-
dc.date.accessioned2011-12-14T12:45:23Z-
dc.date.available2011-12-14T12:45:23Z-
dc.date.issued2006-04-
dc.identifier.urihttp://hdl.handle.net/10316/17911-
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 losing N2 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.language.isoengpor
dc.publisherElsevier B.Vpor
dc.rightsopenAccesspor
dc.titlePhotochemistry of 1-phenyl-tetrazolone isolated in solid argonpor
dc.typearticlepor
degois.publication.firstPage243por
degois.publication.lastPage255por
degois.publication.titleJournal of Photochemistry and Photobiology A: Chemistrypor
dc.peerreviewedYespor
dc.identifier.doi10.1016/j.jphotochem.2005.08.021-
degois.publication.volume179por
uc.controloAutoridadeSim-
item.grantfulltextopen-
item.languageiso639-1en-
item.fulltextCom Texto completo-
crisitem.author.deptFaculty of Sciences and Technology-
crisitem.author.deptFaculty of Sciences and Technology-
crisitem.author.parentdeptUniversity of Coimbra-
crisitem.author.parentdeptUniversity of Coimbra-
crisitem.author.researchunitCQC - Coimbra Chemistry Centre-
crisitem.author.researchunitCQC - Coimbra Chemistry Centre-
crisitem.author.parentresearchunitFaculty of Sciences and Technology-
crisitem.author.parentresearchunitFaculty of Sciences and Technology-
crisitem.author.orcid0000-0002-8705-0160-
crisitem.author.orcid0000-0001-5983-7743-
crisitem.author.orcid0000-0003-3252-3482-
crisitem.author.orcid0000-0002-8264-6854-
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais
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