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Artículo

NMR characterization of hydrate and aldehyde forms of imidazole-2- carboxaldehyde and derivatives

Lazaro Martinez, Juan ManuelIcon ; Romasanta, Pablo NicolasIcon ; Chattah, Ana KarinaIcon ; Buldain, Graciela YolandaIcon
Fecha de publicación: 05/2010
Editorial: American Chemical Society
Revista: Journal of Organic Chemistry
ISSN: 0022-3263
e-ISSN: 1520-6904
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
Química Orgánica

Resumen

The existence and stability of the aldehyde-hydrate form of imidazole-2-carboxaldehyde (4) were studied using FTIR together with solution- and solid-state NMR experiments. The results allowed us to conclude that the hydrate form was stable and precipitated at pH = 8.0 and that the aldehyde form was isolated at pH = 6.5 and 9.5. Moreover, the presence of the aldehyde-hydrate form was studied through NMR experiments in D2O at both alkaline and acidic pH. In addition, the tautomeric forms of the 2-substituted imidazole compounds were also analyzed to investigate the influence of the hybridization on the carbon adjacent to the imidazole ring, by 13C NMR in DMSO-d6, acetone-d6, and CDCl3. The presence of the syn- and anti-isomers of oxime 8 obtained from 4 were characterized by solid-state NMR and variable-temperature NMR experiments in acetone-d 6.
Palabras clave: Imidazole-2-carboxaldehyde , Hydrate , NMR , Aldehyde forms
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/112934
URL: https://pubs.acs.org/doi/10.1021/jo902588s
DOI: https://doi.org/10.1021/jo902588s
Colecciones
Articulos(IFEG)
Articulos de INST.DE FISICA ENRIQUE GAVIOLA
Articulos(OCA HOUSSAY)
Articulos de OFICINA DE COORDINACION ADMINISTRATIVA HOUSSAY
Citación
Lazaro Martinez, Juan Manuel; Romasanta, Pablo Nicolas; Chattah, Ana Karina; Buldain, Graciela Yolanda; NMR characterization of hydrate and aldehyde forms of imidazole-2- carboxaldehyde and derivatives; American Chemical Society; Journal of Organic Chemistry; 75; 10; 5-2010; 3208-3213
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