葫芦脲[7]对季铵盐正离子和二价阳离子 C(2)-H 活性的抑制作用。

Inhibition of C(2)-H Activity on Alkylated Imidazolium Monocations and Dications upon Inclusion by Cucurbit[7]uril.

机构信息

State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.

Department of Chemistry, Queen's University , 90 Bader Lane, Kingston, ON K7L 3N6, Canada.

出版信息

J Org Chem. 2016 Oct 7;81(19):9494-9498. doi: 10.1021/acs.joc.6b01853. Epub 2016 Sep 15.

DOI:10.1021/acs.joc.6b01853

PMID:27602525

Abstract

The inclusions of 1-methyl-3-alkylimidazolium cations (ICn, n = 4, 6, and 8) and 3,3'-bis(3-(1-methylimidazolium))-1,n-alkane (DICn, n = 4, 6, and 8) in the macrocyclic cucurbit[7]uril result in a decrease (up to 25-fold) of the C(2)-H/D exchange rate constants and an increase in the C(2)-H pK values (ΔpK = 0.34 to 1.45). The alkyl chain lengths were found to play an important role in the extent of C(2)-H activity inhibition, upon complexation with cucurbit[7]uril.

摘要

1-甲基-3-烷基咪唑阳离子（ICn，n = 4、6 和 8）和 3,3'-双（3-（1-甲基咪唑基））-1，n-烷烃（DICn，n = 4、6 和 8）在大环瓜环[7]脲中的包含导致 C（2）-H/D 交换速率常数降低（高达 25 倍）和 C（2）-H pK 值增加（ΔpK = 0.34 至 1.45）。发现烷基链长度在与瓜环[7]脲络合时对 C（2）-H 活性抑制的程度起着重要作用。