Inhibition of C(2)-H Activity on Alkylated Imidazolium Monocations and Dications upon Inclusion by Cucurbit[7]uril.
The inclusions of 1-methyl-3-alkylimidazolium cations (ICn+, n = 4, 6, and 8) and 3,3'-bis(3-(1-methylimidazolium))-1,n-alkane (DICn2+, 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 pKavalues (ΔpKa= 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.
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.
Shengke
S
Li
Department of Chemistry, Queen's University , 90 Bader Lane, Kingston, ON K7L 3N6, Canada.
Ian W
IW
Wyman
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.
Chunming
C
Wang
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.
Yitao
Y
Wang
Department of Chemistry, Queen's University , 90 Bader Lane, Kingston, ON K7L 3N6, Canada.
Donal H
DH
Macartney
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau , Taipa, Macau SAR, China.
Ruibing
R
Wang