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Abstract:

The UV-C induced photoaddition of water to N-alkyl-N′-methylimidazolium cations was studied. The main photoreaction products exhibit chemical additions of a proton and a hydroxyl group to either positions 4 or 5 of the imidazolium ring. For unsymmetrical imidazolium cations, two positional isomers were obtained as products. In these cases, the most abundant isomer is the one in which the hydroxyl group adds at the side of the ring having the longer alkyl substituent. Experiments performed in D2O solutions reveal that the additions of proton and hydroxyl group never take place at the same carbon atom, in a reaction that produces equal amounts of diastereoisomers. Moreover, the formation of diastereoisomers at equal proportions suggests that the reaction proceeds in an unconcerted fashion. © 2015 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Photochemistry of imidazolium cations. Water addition to methylimidazolium ring induced by UV radiation in aqueous solution
Autor:Sarmiento, G.P.; Zelcer, A.; Espinosa, M.S.; Babay, P.A.; Mirenda, M.
Filiación:Gerencia Química, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Av. Gral. Paz 1499, San Martín, Buenos Aires B1650KNA, Argentina
CONICET, Av. Rivadavia 1917, Buenos Aires, C1033AAJ, Argentina
ECyT-UNSAM, 25 de Mayo y Francia, San Martín, Buenos Aires C.P.: 1650, Argentina
Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. II, Buenos Aires, C1428EHA, Argentina
Palabras clave:Imidazolium; Ionic liquid; Photoaddition; UV-C reaction; Water addition
Año:2016
Volumen:314
Página de inicio:155
Página de fin:163
DOI: http://dx.doi.org/10.1016/j.jphotochem.2015.07.018
Título revista:Journal of Photochemistry and Photobiology A: Chemistry
Título revista abreviado:J. Photochem. Photobiol. A Chem.
ISSN:10106030
CODEN:JPPCE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10106030_v314_n_p155_Sarmiento

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Citas:

---------- APA ----------
Sarmiento, G.P., Zelcer, A., Espinosa, M.S., Babay, P.A. & Mirenda, M. (2016) . Photochemistry of imidazolium cations. Water addition to methylimidazolium ring induced by UV radiation in aqueous solution. Journal of Photochemistry and Photobiology A: Chemistry, 314, 155-163.
http://dx.doi.org/10.1016/j.jphotochem.2015.07.018
---------- CHICAGO ----------
Sarmiento, G.P., Zelcer, A., Espinosa, M.S., Babay, P.A., Mirenda, M. "Photochemistry of imidazolium cations. Water addition to methylimidazolium ring induced by UV radiation in aqueous solution" . Journal of Photochemistry and Photobiology A: Chemistry 314 (2016) : 155-163.
http://dx.doi.org/10.1016/j.jphotochem.2015.07.018
---------- MLA ----------
Sarmiento, G.P., Zelcer, A., Espinosa, M.S., Babay, P.A., Mirenda, M. "Photochemistry of imidazolium cations. Water addition to methylimidazolium ring induced by UV radiation in aqueous solution" . Journal of Photochemistry and Photobiology A: Chemistry, vol. 314, 2016, pp. 155-163.
http://dx.doi.org/10.1016/j.jphotochem.2015.07.018
---------- VANCOUVER ----------
Sarmiento, G.P., Zelcer, A., Espinosa, M.S., Babay, P.A., Mirenda, M. Photochemistry of imidazolium cations. Water addition to methylimidazolium ring induced by UV radiation in aqueous solution. J. Photochem. Photobiol. A Chem. 2016;314:155-163.
http://dx.doi.org/10.1016/j.jphotochem.2015.07.018