Proline catalyzed Transamidation of amides: DFT study

초록

L-proline is known to catalyze the transamidation reaction between carboxamides and amines. The role of the catalyst was studied theoretically with the B3LYP//6-31++g* level of theory using Gaussian 09 package. The transamidation reaction without catalyst requires a higher barrier of 47.89 kcal/mol. In the presence of catalyst, however, the reaction proceeds through a multi-step mechanism and the energy barrier is much lower than the reaction without catalyst. We also studied the reaction mechanism in solvent, higher temperature, and the role of bulky groups in the real system. From this study, novel mechanism for dehydration is also proposed.