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dc.contributor.author
Ismael, Amín
dc.contributor.author
Cristiano, M.L.S.
dc.contributor.author
Fausto, Rui
dc.contributor.author
Gomez Zavaglia, Andrea
dc.date.available
2021-05-04T16:11:35Z
dc.date.issued
2010-11
dc.identifier.citation
Ismael, Amín; Cristiano, M.L.S.; Fausto, Rui; Gomez Zavaglia, Andrea; Tautomer selective photochemistry in 1-(tetrazol-5-yl)ethanol; American Chemical Society; Journal of Physical Chemistry A; 114; 50; 11-2010; 13076-13085
dc.identifier.issn
1089-5639
dc.identifier.uri
http://hdl.handle.net/11336/131307
dc.description.abstract
A 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.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Tetrazole
dc.subject
Photochemistry
dc.subject.classification
Alimentos y Bebidas
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Otras Ingenierías y Tecnologías
dc.subject.classification
INGENIERÍAS Y TECNOLOGÍAS
dc.title
Tautomer selective photochemistry in 1-(tetrazol-5-yl)ethanol
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2021-04-23T13:49:16Z
dc.identifier.eissn
1520-5215
dc.journal.volume
114
dc.journal.number
50
dc.journal.pagination
13076-13085
dc.journal.pais
Estados Unidos
dc.journal.ciudad
New York
dc.description.fil
Fil: Ismael, Amín. Universidad de Algarve; Portugal
dc.description.fil
Fil: Cristiano, M.L.S.. Universidad de Algarve; Portugal
dc.description.fil
Fil: Fausto, Rui. Universidad de Coimbra; Portugal
dc.description.fil
Fil: Gomez Zavaglia, Andrea. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Criotecnología de Alimentos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Criotecnología de Alimentos; Argentina. Universidad de Coimbra; Portugal
dc.journal.title
Journal of Physical Chemistry A
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/jp109215q
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jp109215q
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