Solute-solvent interactions in imidazolium camphorsulfonate ionic liquids.
We directly observe the interaction between 1-butyl-3-methylimidazolium (bmim) or 1-butyl-2,3-dimethylimidazolium (bm(2)im) and the solute, ethyl acrylate (EA), which is the popular dienophile in the Diels-Alder reaction and an H-bonding acceptor, by using specially designed electrospray mass spectrometry. In imidazolium ionic liquids, cation-anion interactions are controlled by selecting the appropriate anion, and the naked C(2)-H of imidazolium, which loosely interacts with its counterion, can readily interact with an H-bonding acceptable solute. The ion-counterion (solvent-solvent) interaction affects the ion-solute (solvent-solute) interaction. This relation is one of the key criteria for selecting the cation-anion combination in tailoring ILs.
Nobuoka
Kaoru
K
Department of Applied Chemistry, Faculty of Engineering, Oita University, Oita, 700 Dannoharu, Japan. ishichem@cc.oita-u.ac.jp
Kitaoka
Satoshi
S
Iio
Masashi
M
Harran
Thomas
T
Ishikawa
Yuichi
Y
D000179:Acrylates / Q000737:chemistry*; D002164:Camphor / Q000031:analogs & derivatives* / Q000737:chemistry; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D048288:Imidazolines / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000295:instrumentation / Q000379:methods; D015394:Molecular Structure; D012995:Solubility; D012997:Solvents / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000295:instrumentation / Q000379:methods; D017550:Spectroscopy, Fourier Transform Infrared / Q000295:instrumentation / Q000379:methods
C525965:1-butyl-2,3-dimethylimidazolium; C525963:1-butyl-3-methylimidazolium; D000179:Acrylates; D007093:Imidazoles; D048288:Imidazolines; D052578:Ionic Liquids; D012997:Solvents; C040833:ethyl acrylate; D002164:Camphor; C006881:10-camphorsulfonic acid