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

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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?

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Publication details

The article was received on 16 Feb 2019, accepted on 03 Apr 2019 and first published on 04 Apr 2019


Article type: Research Article
DOI: 10.1039/C9QO00251K
Citation: Org. Chem. Front., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9QO00251K

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