Issue 11, 2019

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
16 Feb 2019
Accepted
03 Apr 2019
First published
04 Apr 2019

Org. Chem. Front., 2019,6, 1821-1831

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

C. Yan, R. Wu, K. Lu, F. Yang, X. Yang, R. Wang, X. Yang, P. Zhou and X. Shao, Org. Chem. Front., 2019, 6, 1821 DOI: 10.1039/C9QO00251K

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