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Why electrostatically enhanced thiourea is better than Schreiner's thiourea in both catalytic activity and regioselectivity?

Authors :
Chaoxian Yan
Rui Wang
Panpan Zhou
Rui-Zhi Wu
Ka Lu
Xiao-Shan Yang
Xiangfeng Shao
Xing Yang
Fang-Ling Yang
Source :
Organic Chemistry Frontiers. 6:1821-1831
Publication Year :
2019
Publisher :
Royal Society of Chemistry (RSC), 2019.

Abstract

Electrostatically enhanced thiourea behaves more efficiently than Schreiner's thiourea in the ring-opening aminolysis of styrene oxide with aniline, and the underlying reasons were uncovered by DFT calculations, the distortion/interaction theory, and NBO and QTAIM analyses. Electrostatically enhanced thiourea combines with a substrate much stronger than Schreiner's thiourea, so it activates the substrate more efficiently and thus lowers the activation energy more significantly, leading to a higher reaction rate and a greater conversion.

Details

ISSN :
20524129
Volume :
6
Database :
OpenAIRE
Journal :
Organic Chemistry Frontiers
Accession number :
edsair.doi...........5000e77031dbb097b682393adfc3052e
Full Text :
https://doi.org/10.1039/c9qo00251k