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Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study

2008Journal article Open Access
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dc.contributor.authorFrija, L.
dc.contributor.authorKhmelinskii, Igor
dc.contributor.authorSerpa, C.
dc.contributor.authorReva, I. D.
dc.contributor.authorFausto, R.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.date.accessioned2014-06-06T13:31:23Z
dc.date.available2014-06-06T13:31:23Z
dc.date.issued2008
dc.date.updated2014-06-05T11:37:19Z
dc.description.abstractThe photochemistry of three 5-allyloxy-tetrazoles, in methanol, acetonitrile and cyclohexane was studied by product analysis and laser flash photolysis. The exclusive primary photochemical process identified was molecular nitrogen elimination, with formation of 1,3-oxazines. These compounds were isolated in reasonable yields by column chromatography on silica gel and were fully characterized. DFT(B3LYP)/6-31G(d,p)calculations predict that these 1,3-oxazines can adopt two tautomeric forms (i) with the NH group acting as a bridge connecting the oxazine and phenyl rings and (ii) with the –N=bridge and the proton shifted to the oxazine ring. Both tautomeric forms are relevant in the photolysis of oxazines in solution. Secondary reactions were observed, leading to the production of phenyl vinyl-hydrazines, enamines, aniline and phenyl-isocyanate. Transient absorption, detected by laser flash photolysis, is attributed to the formation of triplet 1,3-biradicals generated from the excited 5-allyloxy-tetrazoles. The 1,3-biradicals are converted to 1,6-biradicals by proton transfer, which, after intersystem crossing, decay to generate the products. Solvent effects on the photoproduct distribution and rate of decomposition are negligible.por
dc.identifier.citationFrija, L. M. T.; Khmelinskii, I. V.; Serpa, C.; Reva, I. D.; Fausto, R.; Cristiano, M. L. S. Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study, Organic & Biomolecular Chemistry, 6, 6, 1046-1046, 2008.por
dc.identifier.doihttp://dx.doi.org/10.1039/b718104c
dc.identifier.issn1477-0520
dc.identifier.otherAUT: IKH00165; MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4217
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherRoyal Society of Chemistrypor
dc.relationStudies on the reactivity of derivatives of tetrazole and isothiazole; isothiazolyltetrazoles as potential bidentate ligands and their application in catalysis
dc.relationPhotochemistry and Matrix Isolation Spectroscopy of Molecular Species with Astrophysical and Atmospheric Relevance
dc.relationMatrix Isolation Spectroscopy and Study of the Condensed Phases of Molecules with Potential Cryoprotectant Activity
dc.relation.publisherversionView Article Onlinepor
dc.titlePhotochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis studypor
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleStudies on the reactivity of derivatives of tetrazole and isothiazole; isothiazolyltetrazoles as potential bidentate ligands and their application in catalysis
oaire.awardTitlePhotochemistry and Matrix Isolation Spectroscopy of Molecular Species with Astrophysical and Atmospheric Relevance
oaire.awardTitleMatrix Isolation Spectroscopy and Study of the Condensed Phases of Molecules with Potential Cryoprotectant Activity
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FQUI%2F67674%2F2006/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/POCI/POCI%2FQUI%2F58937%2F2004/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F17945%2F2004/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/POCI/POCI%2FQUI%2F59019%2F2004/PT
oaire.citation.endPage1055por
oaire.citation.issue6por
oaire.citation.startPage1046por
oaire.citation.titleOrganic & Biomolecular Chemistrypor
oaire.citation.volume6por
oaire.fundingStream3599-PPCDT
oaire.fundingStreamPOCI
oaire.fundingStreamSFRH
oaire.fundingStreamPOCI
person.familyNameKhmelinskii
person.familyNameCristiano
person.givenNameIgor
person.givenNameMaria de Lurdes
person.identifier0000000420541031
person.identifier.ciencia-id0D1A-CB6C-6316
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-6116-184X
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridC-9587-2011
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id6701444934
person.identifier.scopus-author-id9238724800
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspor
rcaap.typearticlepor
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