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RESEARCH ARTICLE
Contents Vol 73(1)

Effect of Substitution for Insertion of CO2 into Epoxides and Aziridines: An Ab Initio Study

Yunhan Yang https://orcid.org/0000-0003-3790-1606 A , Fenji Li A , Cuicui Yang A , Lijuan Jia A , Lijuan Yang A , Futing Xia A B C and Jinhui Peng B
+ Author Affiliations
- Author Affiliations

A Key Laboratory of Resource Clean Conversion in Ethnic Regions, Education Department of Yunnan, Yunnan Minzu University, Kunming 650500, China.

B State Key Laboratory of Complex Nonferrous Metal Resources Clean Utilization, Kunming University of Science and Technology, Kunming 650500, China.

C Corresponding author. Email: xiafuting@163.com

Australian Journal of Chemistry 73(1) 30-42 https://doi.org/10.1071/CH19296
Submitted: 1 July 2019  Accepted: 28 October 2019   Published: 3 December 2019

Abstract

The insertion of CO2 into epoxides and aziridines has been studied using density functional theory (B3LYP) and ab initio (MP2) methods, and the effect of substitution for the two reactions are further explored. It is found that the reactivity of epoxides and aziridines are similar, and insertion of CO2 proceeds through a concerted mechanism. The substitutions of methyl and phenyl does not change the reaction mechanism, but the transition state for the substitution on the attacking position becomes loose with a lower free energy barrier. The substitutions of methyl and phenyl decrease the free energy barrier, with phenyl substitution having a greater affect. The results also show that the free energy barriers for the insertions of CO2 into aziridines are ~10 kcal mol−1 lower than the corresponding reactions of CO2 with epoxides.


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