342789-81-5Relevant articles and documents
Aggregation behavior of 1-dodecyl-3-methylimidazolium bromide in aqueous solution: Effect of ionic liquids with aromatic anions
Gu, Yingqiu,Shi, Lijuan,Cheng, Xiyuan,Lu, Fei,Zheng, Liqiang
, p. 6213 - 6220 (2013)
The effects of ionic liquids (ILs), 1-butyl-3-methylimidazolium methylsulfonate (bmimMsa), 1-butyl-3-methylimidazolium benzenesulfonate (bmimBsa), and 1-butyl-3-methylimidazolium 2-naphthalenesulfonate (bmimNsa), on the aggregation behavior of 1-dodecyl-3-methylimidazolium bromide (C 12mimBr) in aqueous solution were investigated by surface tension, dynamic light scattering measurements, and 1H NMR spectroscopy. The ability to promote the surfactant aggregation is in the order bmimNsa > bmimBsa > bmimMsa. Nevertheless, only bmimNsa distinctly reduces both the CMC value and the surface tension at CMC. Due to the penetration of C 10H7SO3-anions into the surfactant aggregate, bmimNsa is found to induce a phase transition from micelles to vesicles, whereas the other ILs only slightly increase the sizes of micelles. The combined effect of intermolecular interactions, such as hydrophobic effect, electrostatic attractions, and π-π stacking interactions, is supposed to be responsible for this structural transformation, in which π-π stacking plays an important role.
SN2 Fluorination reactions in ionic liquids: A mechanistic study towards solvent engineering
Oh, Young-Ho,Jang, Hyeong Bin,Im, Suk,Song, Myoung Jong,Kim, So-Yeon,Park, Sung-Woo,Chi, Dae Yoon,Song, Choong Eui,Lee, Sungyul
, p. 418 - 422 (2011)
In the catalysis of SN2 fluorination reactions, the ionic liquid anion plays a key role as a Lewis base by binding to the counterion Cs + and thereby reducing the retarding Coulombic influence of Cs + on the nucleophile F-. The reaction rates also depend critically on the structures of ionic liquid cation, for example, n-butyl imidazolium gives no SN2 products, whereas n-butylmethyl imidazolium works well. The origin of the observed phenomenal synergetic effects by the ionic liquid [mim-tOH][OMs], in which t-butanol is bonded covalently to the cation [mim], is that the t-butanol moiety binds to the leaving group of the substrate, moderating the retarding interactions between the acidic hydrogen and F-. This work is a significant step toward designing and engineering solvents for promoting specific chemical reactions.
Convenient synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter-solvent: Readily access to non-ionic triazolylglycoside surfactants for evaluation of cytotoxic activity
Ketsomboon, Nutthanicha,Saeeng, Rungnapha,Srisook, Klaokwan,Sirion, Uthaiwan
, (2021/08/26)
A convenient method for the one-pot synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter and solvent is described via a sequential one-pot two-step glycosidation-CuAAc click reaction. The reaction was carried out using commercially available substrates, including glycosyl bromides, sodium azide and various long alkyl-chain alkynes to achieve the corresponding products in moderate to high yields. Furthermore, this approach was successfully applied for the preparation of non-ionic monocatenary triazolylglycoside surfactants in excellent yields through simple deacetylation. Subsequently, these surfactants were further evaluated for their cytotoxic activity.