Authors
Francisco Rodriguez-Llansola, Beatriu Escuder, Juan F Miravet
Publication date
2009/8/19
Journal
Journal of the American Chemical Society
Volume
131
Issue
32
Pages
11478-11484
Publisher
American Chemical Society
Description
An l-proline-derived low molecular weight gelator forms gels in nitromethane and nitroethane and acts as a basic catalyst for the Henry nitroaldol reaction of these solvents with 4-nitrobenzaldehyde and 4-chlorobenzaldehyde. The reported catalyst is efficient only upon aggregation into self-assembled fibrillar networks. The formation of the gels is associated to a basicity boost of the l-proline residues. Gel dissociation blocks the catalytic efficiency for the nitroaldol reaction but enhances a reaction pathway leading to alkenes. Because of the reversible nature of supramolecular gels, subtle temperature changes allow for a reversible sol−gel transition associated to an activation of the catalyst. The catalytic gel from nitroethane is significantly more active than the one from nitromethane probably because of its different structure as revealed by X-ray diffraction and thermal stability studies. The results shown indicate that in …
Total citations
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Scholar articles
F Rodriguez-Llansola, B Escuder, JF Miravet - Journal of the American Chemical Society, 2009