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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 35, Number 9
BKCSDE 35(9)
September 20, 2014 

Theoretical Insight into the Mechanism of an Efficient L-Proline-catalyzed Transamidation of Acetamide with Benzylamine
Weirong Wu
Transamidation, L-Proline-catalydst, Pyrrolidine-catalydst, Acetamide, Benzylamine
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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