Synthesis, characterization, and crystal structure of several novel acidic ionic liquids based on the corresponding 1-alkylbenzimidazole with tetrafluoroboric acid

A series of acidic task-specific ionic liquids 1-R-2-2-R(1)benzimidazolium tetrafluoroborate (R-1 = Me, R-2 = Me, Et, Pr-n, Bu-n, Pen-n) were prepared by simple acid-base neutralization of the corresponding 1-alkylbenzimidazole and tetrafluoroboric acid. The compounds were characterized by FTIR spectra, elemental analysis, (HNMR)-H-1 spectra and thermo-gravimetric analysis. These new ionic liquids are nonvolatile, and have potential use as alternatives to conventional organic solvents due to their solubility and thermal stability. These novel tetrafluoroborate salts show good catalytic activity to esterification of carboxylic acids with alcohols under mild reaction conditions, which could maintain good catalytic performance after recycling at least six times. Furthermore, a crystal of one compound, [H-bmBim]BF4, was prepared, with the crystal structure determined by X-ray diffraction analysis. The molecular structure is formed by weak pi-pi interactions and intermolecular hydrogen bonds between the benzimidazole rings, yielding a three-dimensional net-like supramolecule. (C) 2010 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.