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Tautomer selective photochemistry in 1-(Tetrazol-5-yl)ethanol

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dc.contributor.authorIsmael, Amin
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorFausto, R.
dc.contributor.authorGómez-Zavaglia, A.
dc.date.accessioned2014-06-07T11:19:00Z
dc.date.available2014-06-07T11:19:00Z
dc.date.issued2010
dc.date.updated2014-06-05T09:06:58Z
dc.description.abstractA combined matrix isolation FTIR and theoretical DFT/B3LYP/6-311++G(d,p) study of the molecular structure and photochemistry of 1-(tetrazol-5-yl)ethanol [1-TE] was performed. The potential energy surface landscapes of the 1H and 2H tautomers of the compound were investigated and the theoretical results were used to help characterize the conformational mixture existing in equilibrium in the gas phase prior to deposition of the matrices, as well as the conformers trapped in the latter. In the gas phase, at room temperature, the compound exists as a mixture of 12 conformers (five of the 1H tautomer and seven of the 2H tautomer). Upon deposition of the compound in an argon matrix at 10 K, only three main forms survive, because the low barriers for conformational isomerization allow extensive conformational cooling during deposition. Deposition of the matrix at 30 K led to further simplification of the conformational mixture with only one conformer of each tautomer of 1-TE surviving. These conformers correspond to the most stable forms of each tautomer, which bear different types of intramolecular H-bonds: 1H-I has an NH· · ·O hydrogen bond, whereas 2H-I has an OH· · ·N hydrogen bond. Upon irradiating with UV light (λ > 200 nm), a matrix containing both 1H-I and 2H-I forms, an unprecedented tautomer selective photochemistry was observed, with the 2H tautomeric form undergoing unimolecular decomposition to azide + hydroxypropanenitrile and the 1H-tautomer being photostable.por
dc.identifier.citationIsmael, A.; Cristiano, M. L. S.; Fausto, R.; Gomez-Zavaglia, A. Tautomer Selective Photochemistry in 1-(Tetrazol-5-yl)ethanol, The Journal of Physical Chemistry A, 114, 50, 13076-13085, 2010.por
dc.identifier.doihttp://dx.doi.org/10.1021/jp109215q
dc.identifier.issn1089-5639
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4244
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherAmerican Chemical Societypor
dc.titleTautomer selective photochemistry in 1-(Tetrazol-5-yl)ethanolpor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage13085por
oaire.citation.issue50por
oaire.citation.startPage13076por
oaire.citation.titleThe Journal of Physical Chemistry Apor
oaire.citation.volume114por
person.familyNameIsmael
person.familyNameCristiano
person.givenNameAmin
person.givenNameMaria de Lurdes
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-7346-5998
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridA-8153-2013
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id35203489500
person.identifier.scopus-author-id9238724800
rcaap.rightsrestrictedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublicationfa01ef7f-7a2a-4f74-a405-714360b862f3
relation.isAuthorOfPublicationb16751a6-748e-44b0-9c59-058cbd5b2cc3
relation.isAuthorOfPublication.latestForDiscoveryfa01ef7f-7a2a-4f74-a405-714360b862f3

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