Influence of water-soluble pillararene hosts on Kemp elimination

Since pillar[5]arene was first discovered in 2008, it has developed into a multifunctional supramolecular host. Its application covers many fields from drug delivery and chemical sensing to the construction of molecular machines, and so on. Supramolecular catalysis based on pillar[ n ]arenes is one...

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Bibliographic Details
Published in:RSC advances 2021-11, Vol.11 (6), p.38115-38119
Main Authors: Liu, Qian, Tian, Xueqi, Shen, Yuhong, Huang, Xingyi, Wang, Kaiya, Hu, Xiao-Yu
Format: Article
Language:English
Subjects:
Acceleration
Aromatic compounds
Chemistry
Molecular machines
Water chemistry
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Summary:Since pillar[5]arene was first discovered in 2008, it has developed into a multifunctional supramolecular host. Its application covers many fields from drug delivery and chemical sensing to the construction of molecular machines, and so on. Supramolecular catalysis based on pillar[ n ]arenes is one of the hot research topics that has emerged in recent years. In this paper, we have synthesized two water-soluble pillar[5]arenes with peripheral rims bearing opposite charges and investigated their influence on Kemp elimination reaction of 1,2-phenylisoxazole derivatives. It is found that both hosts have a moderate rate acceleration effect on the reaction, and the positively charged host H1 has a greater impact on the reaction rate than the negatively charged host H2 . Water-soluble pillar[5]arenes with different rim charges have been successfully used to catalyze Kemp elimination reaction of 1,2-phenylisoxazole derivatives.
ISSN:2046-2069
2046-2069
DOI:10.1039/d1ra07958a