Transition‐Metal‐Free Synthesis of Perdeuterated Imidazolium Ionic Liquids by Alkylation and H/D Exchange

Abstract

Economic, transition-metal-free syntheses of partially or completely deuterated imidazolium ionic liquids (ILs) were developed. Double alkylation starting from imidazole afforded side-chain deuterated imidazolium ionic liquids, which subsequently were fully deuterated by H/D-exchange on the cation ring. Isotopic exchange was studied for a range

BIOnic Liquids: Imidazolium-based Ionic Liquids with Antimicrobial Activity

“…Syntheses [C 4 mim]Br, [C 8 mim]Br and [C 16 mim]Br have been prepared according to established literature procedures [15]. The BIOnic Liquids have subsequently been synthesized by transforming the corresponding imidazolium bromide into the hydroxide via ion exchange resin.…”

Heteronuclear NOE Spectroscopy of Ionic Liquids

“…For the last eight years our group has focussed on the establishment and application of NMR spectroscopy in neat ILs. [4][5][6][7][8] It is long established that the nuclear Overhauser effect (NOE) [9] is a powerful tool for the determination of intermolecular interactions. [10][11][12] This effect arises due to dipolar cross relaxation between two spatially neighbouring nuclear spins (typically below 5 ).…”

Kinetic Study of Michael Addition Catalyzed by N‐Methylimidazole in Ionic Liquids: Residual N‐Methylimidazole in Ionic Liquids as a Strong Base

“…Small amounts (1-5 mol-%) of N-methylimidazole, as a basic impurity significantly affected H/D exchange in the synthesis of perdeuterated ILs. [15] ILs have been described as solvent media able to increase amine basicity with respect to conventional solvents. [16] This is in accord with our observation [1] that -proline and piperidine were much better catalysts for Michael additions of methylene-active compounds to chalcone in ILs than in dichloromethane.…”