Theoretical Insight into the Mechanism of an Efficient L-Proline-catalyzed Transamidation of Acetamide with Benzylamine 


Vol. 35,  No. 9, pp. 2673-2678, Sep.  2014
10.5012/bkcs.2014.35.9.2673


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  Abstract

The detailed mechanisms of the efficient L-proline and pyrrolidine catalyzed transamidation of acetamide with benzylamine have been investigated using density functional theory (DFT) calculations. Our calculated results show: (1) the mechanisms of two catalytic cycle reactions are similar. However, the rate-determining steps of their reactions are different for the whole catalytic process. One is the intramole-cular nucleophilic addition reaction of 1-COM, the other is hydrolysis reaction of 2-C. (2) COOH group of L-proline is essential for efficient transamidation. The computational results are in good agreement withthe experiment finding and mechanism resported by Rao et al. for L-proline-catalyzed synthesis of amidesin good to excellent yields.

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  Cite this article

[IEEE Style]

W. Wu, "Theoretical Insight into the Mechanism of an Efficient L-Proline-catalyzed Transamidation of Acetamide with Benzylamine," Bulletin of the Korean Chemical Society, vol. 35, no. 9, pp. 2673-2678, 2014. DOI: 10.5012/bkcs.2014.35.9.2673.

[ACM Style]

Weirong Wu. 2014. Theoretical Insight into the Mechanism of an Efficient L-Proline-catalyzed Transamidation of Acetamide with Benzylamine. Bulletin of the Korean Chemical Society, 35, 9, (2014), 2673-2678. DOI: 10.5012/bkcs.2014.35.9.2673.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949