Theoretical studies on the aminolysis mechanism of propylene carbonate with ammonia
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- 作者：Rong Chen (1)
Xiaoling Luo (1)
Guoming Liang (1)
1. College of Chemistry ; Chongqing Normal University ; Chongqing ; 401331 ; China - 关键词：Aminolysis of ester ; Propylene carbonate ; Catalytic role ; Mechanism ; PCM model
- 刊名：Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta)
- 出版年：2015
- 出版时间：March 2015
- 年：2015
- 卷：134
- 期：3
- 全文大小：1,725 KB
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- 刊物主题：Chemistry
Theoretical and Computational Chemistry
Inorganic Chemistry
Organic Chemistry
Physical Chemistry - 出版者：Springer Berlin / Heidelberg
- ISSN：1432-2234
文摘
The possible mechanisms of the aminolysis reaction of propylene carbonate with ammonia were investigated by computational techniques. Optimized structures for all the stationary points were examined by employing the B3LYP/6-311++G(d,p) and MP2/6-311++G(d,p) methods. The uncatalyzed, base-catalyzed and acid-catalyzed aminolysis reactions were taken into account. Two possible mechanisms of the concerted process and the addition/elimination stepwise pathway are investigated, and the first stages of the stepwise mechanism for all pathways are the rate-limiting processes. The results indicate that the concerted process of non-catalyzed aminolysis has lower energy barrier in comparison with the stepwise mechanism. Concerning the base-catalyzed and acid-catalyzed aminolysis, the neutral stepwise pathway is more favorable than the concerted mechanism and the energy barriers of all steps are lower than those of the uncatalyzed aminolysis. The solvent effect by a polarized continuum model does not significantly change the conclusion.