5-Phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde
CAS Number:
881676-90-0
Molecular Formula:
C16H12N2O3S
Why electrostatically enhanced thiourea is better than Schreiner's thiourea in both catalytic activity and regioselectivity?
Literature Information
Publication Date
2019-04-04
DOI
10.1039/C9QO00251K
Impact Factor
5.281
Authors
Chao-Xian Yan, Rui-Zhi Wu, Ka Lu, Fang-Ling Yang, Xiao-Shan Yang, Rui Wang, Xing Yang, Pan-Pan Zhou, Xiangfeng Shao
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(S)-3-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylpropanoic acid
CAS Number:
1217663-60-9
Molecular Formula:
C24H21NO4
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