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The estimation of ΔHsolv using the method described in ref 10 monitors the chemical shift of the proton in the 2-position of the ring as a function of the concentration of the imidazolium salt in acetonitrile. At low concentration the ions are assumed to be completely solvated, and at high concentration it is assumed that they interact. The interactions, while being predominantly Coulombic, also involve H-bonding between the 2-proton of the imidazolium cation and the iodide anion, thus influencing the chemical shift of the 2-proton. For the ether-containing anion in 3 we also explored the interaction between the protons on the C atoms next to the O atoms of the ether groups, but no correlation was observed, so any contribution toward solvation from the ether group was ignored
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solv using the method described in ref 10 monitors the chemical shift of the proton in the 2-position of the ring as a function of the concentration of the imidazolium salt in acetonitrile. At low concentration the ions are assumed to be completely solvated, and at high concentration it is assumed that they interact. The interactions, while being predominantly Coulombic, also involve H-bonding between the 2-proton of the imidazolium cation and the iodide anion, thus influencing the chemical shift of the 2-proton. For the ether-containing anion in 3 we also explored the interaction between the protons on the C atoms next to the O atoms of the ether groups, but no correlation was observed, so any contribution toward solvation from the ether group was ignored.
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Electrospray ionization mass spectrometry was also used to determine if 3 interacted more strongly with inorganic salts compared to 1. It is well known that ionic liquids are often observed as aggregates in ESI-MS. Halide impurities are also observed forming aggregates with the ionic liquid cations. However, in a direct comparison of 1 and 3 containing NaI no differences were observed between the aggregates observed, indicating that the magnitudes of the interaction between the two IL cations and iodide are essentially the same. See for example:(a) Dyson, P. J.; McIndoe, J. S.; Zhao, D. Chem. Commun. 2003, 508.
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Electrospray ionization mass spectrometry was also used to determine if 3 interacted more strongly with inorganic salts compared to 1. It is well known that ionic liquids are often observed as aggregates in ESI-MS. Halide impurities are also observed forming aggregates with the ionic liquid cations. However, in a direct comparison of 1 and 3 containing NaI no differences were observed between the aggregates observed, indicating that the magnitudes of the interaction between the two IL cations and iodide are essentially the same. See for example:(a) Dyson, P. J.; McIndoe, J. S.; Zhao, D. Chem. Commun. 2003, 508.
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1H NMR spectrum following this process.
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