353239-08-4Relevant academic research and scientific papers
Inter- and intramolecular interactions in imidazolium protic ionic liquids
Moschovi, Anastasia Maria,Dracopoulos, Vassileios,Nikolakis, Vladimiros
, p. 8673 - 8683 (2014)
The interactions of alkyl substituted imidazolium bis(trifluoromethanolsulfonyl)imide protic ionic liquids (PILs) HC nImNTf2 (n = 0-12) were studied using vibrational spectroscopy (FT-IR/ATR and FT-Raman) and differential scanning calorimetry (DSC). The effect of alkyl substituent length (n = 0-12) and temperature on the relative magnitude of the different interactions is elucidated. For short carbon alkyl chains (n 3 the van der Waals forces between the chains and ??-?? interaction between neighboring imidazolium rings become important. The tendency of reducing the melting point and increasing glass transition values with the lengthening of the alkyl chain was also noticed as a result the increasing contribution of the van der Waals forces to the overall interactions. Finally, we also show that the conformational isomerism of the anion (expressed by ??Heq) is a good indicator of the relative magnitude of the interactions. When Coulombic interactions are predominant, the trans conformer is the most probable, while when other type of interactions (HB, vdW, etc.) become important the cis conformer is favored. ? 2014 American Chemical Society.
Metal- And solvent-free synthesis of aniline- And phenol-based triarylmethanes: Via Br?nsted acidic ionic liquid catalyzed Friedel-Crafts reaction
Jaratjaroonphong, Jaray,Saeeng, Rungnapha,Senapak, Warapong,Sirion, Uthaiwan,ponpao, nipaphorn
, p. 22692 - 22709 (2021/07/21)
A beneficial, scalable and efficient methodology for the synthesis of aniline-based triarylmethanes has been established through the double Friedel-Crafts reaction of commercial aldehydes and primary, secondary or tertiary anilines using Br?nsted acidic ionic liquid as a powerful catalyst, namely [bsmim][NTf2]. This protocol was successfully performed under metal- and solvent-free conditions with a broad range of substrates, giving the corresponding aniline-based triarylmethane products in good to excellent yields (up to 99%). In addition, alternative aromatic nucleophiles such as phenols and electron-rich arenes were also studied using this useful approach to achieve a diversity of triarylmethane derivatives in high to excellent yields. This journal is
Synthesis and crystal structures of 1-alkoxy-3-alkylimidazolium salts including ionic liquids, 1-alkylimidazole 3-oxides and 1-alkylimidazole perhydrates
Laus, Gerhard,Schwaerzler, Alexander,Bentivoglio, Gino,Hummel, Michael,Kahlenberg, Volker,Wurst, Klaus,Kristeva, Elka,Schuetz, Johannes,Kopacka, Holger,Kreutz, Christoph,Bonn, Guenther,Andriyko, Yuriy,Nauer, Gerhard,Schottenberger, Herwig
experimental part, p. 447 - 464 (2009/01/31)
Functionalized quaternary imidazolium salts were prepared with the intention to obtain new ionic liquids (ILs). Thus, more than forty 3-alkoxy-1-alkylimidazolium salts, 3-alkoxy-1-alkyl-2-methylimidazolium salts, 1-methylimidazole 3-oxide and 1,2-dimethylimidazole 3-oxide as well as their salts, 1,3-dihydroxyimidazolium salts and 1,3-dihydroxy-2-methylimidazolium salts were synthesized and characterized by spectroscopy and, to a limited extent, by viscosity and conductivity measurements. Results of fourteen single crystal X-ray structure determinations are reported, among them also the parent compounds 1-hydroxyimidazole 3-oxide and 1-hydroxy-2-methylimidazole 3-oxide. Selective debenzylation of 1-benzyloxy-3-methylimidazolium salts and mono-demethoxylation of 1,3-dimethoxyimidazolium salts were achieved by hydrogenolysis. In addition, a crystalline semiperhydrate of 1,2-dimethylimidazole was characterized. Furthermore, an addition compound of 1-methylimidazole 3-oxide with tris(2-thienyl)borane and a silver carbene complex derived from 1-benzyloxy-3-methylimidazolium hexafluorophosphate was crystallized and characterized.
