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- W2514515145 abstract "Abstract Several symmetrical imidazolium salts were obtained from the natural chiral pool of (1R,2S,5R)-(−)-menthol. First 1,3-bis[(1R,2S,5R)-(−)-menthoxymethyl]imidazolium chloride, which is a prototype for ionic liquids, was prepared with the use of two different methods. Furthermore, metathesis of this symmetrical imidazolium chloride with various salts was carried out. The ion exchange reaction goes smoothly, with the satisfactory yield of 97.5 to 99.5%. Obtained 1,3-bis[(1R,2S,5R)-(−)-menthoxymethyl]imidazolium salts are stable in the air, in contact with water and in commonly used organic solvents. Moreover they are non-volatile and non-flammable. Discussed symmetrical salts belong to chiral ionic liquids (CILs) where the chirality resided in the cation and is associated with the presence of optically active (1R,2S,5R)-(−)-menthol. The diastereotopic protons in the 1H NMR were thoroughly described. Moreover, the 1H NMR and 13C NMR spectra indicated notable differences in the chemical shifts depending on the anion used. Comparing the differences between values of the chemical shifts, the anions were ordered according to their increasing shielding capacities. The changing of the electron density surrounding the imidazolium ring was discussed." @default.
- W2514515145 created "2016-09-16" @default.
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- W2514515145 date "2017-01-01" @default.
- W2514515145 modified "2023-10-01" @default.
- W2514515145 title "Synthesis and spectroscopic properties of symmetrical ionic liquids based on (−)-menthol" @default.
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- W2514515145 doi "https://doi.org/10.1016/j.molliq.2016.08.112" @default.
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