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

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• 作者：Aizpea Zubia ; Fernando P. Cossí ; o ; Iñ ; aki Morao ; Marina Rieumont ; and Xabier Lopez
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：April 28, 2004
• 年：2004
• 卷：126
• 期：16
• 页码：5243 - 5252
• 全文大小：445K
• 年卷期：v.126,no.16(April 28, 2004)
• ISSN：1520-5126

文摘

One reference tertiary amine and three families of structurally related trialkylamines anddendrimers have been synthesized, characterized, and studied by molecular dynamics simulations. Thecatalytic activity of these amines in the nitroaldol (Henry) reaction between 2-nitroethanol and benzaldehydehas been measured by FT-IR spectroscopy. It is found that, in this kind of molecule with only one catalyticcenter at the core, the efficiency of the catalytic process decreases with the size and/or the degree oframification of the dendrimer. According to these results, there is a linear departure from the behaviorpredicted 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 andreagent accessible surfaces.