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- Title
The Formation of Imidazolium Salt Intimate (Contact) Ion Pairs in Solution.
- Authors
Zanatta, Marcileia; Girard, Anne-Lise; Simon, Nathalia M.; Ebeling, Gunter; Stassen, Hubert K.; Livotto, Paolo R.; dos Santos, Francisco P.; Dupont, Jairton
- Abstract
1- n-Butyl-2,3-dimethylimidazolium (BMMI) ionic liquids (ILs) associated with different anions undergo H/D exchange preferentially at 2-Me group of the imidazolium in deuterated solvents. This process is mainly related to the existence of ion pairs rather than the anion basicity. The H/D exchange occurs in solvents (CDCl3 and MeCN for instance) in which intimate contact ion pairs are present and the anion possesses a labile H in its structure, such as hydrogen carbonate and prolinate. In D2O, separated ion pairs are formed and the H/D exchange does not occur. A plausible catalytic cycle is that the IL behaves as a neutral base in the course of all H/D exchange processes. NMR experiments, density functional calculations, and molecular dynamics simulations corroborate these hypotheses.
- Subjects
CHEMICAL synthesis; IMIDAZOLES; CONTACT ion pairs; HYDROGENATION; IONIC liquids; EXCHANGE reactions; BASICITY
- Publication
Angewandte Chemie, 2014, Vol 126, Issue 47, p13031
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201408151