Quantitative Evaluation of the Catalytic Activity of Dendrimers with Only One Active Center at the Core:  Application to the Nitroaldol (Henry) Reaction

Quantitative Evaluation of the Catalytic Activity of Dendrimers with Only One Active Center at the Core:  Application to the Nitroaldol (Henry) Reaction

One reference tertiary amine and three families of structurally related trialkylamines and dendrimers have been synthesized, characterized, and studied by molecular dynamics simulations. The catalytic activity of these amines in the nitroaldol (Henry) reaction between 2-nitroethanol and benzaldehyde...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 126; no. 16; pp. 5243 - 5252
Main Authors: Zubia, Aizpea, Cossío, Fernando P, Morao, Iñaki, Rieumont, Marina, Lopez, Xabier
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 28-04-2004
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
Nitro compound
Kinetic control
Catalytic reaction
Catalyst selectivity
Benzaldehyde
Molecular dynamics method
Theoretical study
Experimental study
Homogeneous catalysis
Tertiary amine
Benzenic compound
Catalyst activity
Mass spectrometry
Dendritic structure
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Summary:One reference tertiary amine and three families of structurally related trialkylamines and dendrimers have been synthesized, characterized, and studied by molecular dynamics simulations. The catalytic activity of these amines in the nitroaldol (Henry) reaction between 2-nitroethanol and benzaldehyde has been measured by FT-IR spectroscopy. It is found that, in this kind of molecule with only one catalytic center at the core, the efficiency of the catalytic process decreases with the size and/or the degree of ramification of the dendrimer. According to these results, there is a linear departure from the behavior predicted by the hard sphere collision theory (HSCT) as the size of the dendrimer increases. Therefore, the behavior of structurally related dendrimers can be quantified in terms of their molecular weight and reagent accessible surfaces.
Bibliography:ark:/67375/TPS-2HRH0B3L-T
istex:18CA9409B318B4E940EC58E7E874578313D70FF8
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja039888s