945017-57-2Relevant academic research and scientific papers
An intermediate for the clean synthesis of ionic liquids: Isolation and crystal structure of 1,3-dimethylimidazolium hydrogen carbonate monohydrate
Bridges, Nicholas J.,Hines, C. Corey,Smiglak, Marcin,Rogers, Robin D.
, p. 5207 - 5212 (2007)
1,3-Dimethylimidazolium-2-carboxylate and carbonic acid have been used to prepare a 1,3-dimethylimidazolium hydrogen carbonate salt by means of a Krapcho reaction. The ability to form hydrogen carbonate azolium salts allows for them to be used as precursors for fast, efficient, environmentally benign, and halide-free syntheses of many ionic liquids by a simple, acid-base reaction of virtually any acid (inorganic, organic, and organic noncarboxylic) with a pKa less than that of HCO3 -. ditionally, the kinetics of this reaction can be accelerated by employing catalytic amounts of DMSO (a traditional Krapcho solvent used in decarboxylation reactions) to catalyze the decarboxylation. The crystal structure of 1,3-dimethylimidazolium hydrogen carbonate monohydrate is the first example of an imidazolium-based hydrogen carbonate salt. There is a strong 2D hydrogen-bonded network with facially it-stacked imidazolium cations located in the cavities created by this framework.
Base-Free Generation of Organic Electron Donors from Air-Stable Precursors
Tintori, Guillaume,Nabokoff, Pierre,Buhaibeh, Ruqaya,Bergé-Lefranc, David,Redon, Sébastien,Broggi, Julie,Vanelle, Patrice
supporting information, p. 3148 - 3153 (2018/03/13)
Organic electron donors (OEDs) are powerful reducing agents recognized for their potential in the reduction of challenging substrates and in original applications. Nonetheless, their low stability in atmospheric oxygen or over time complicates their manipulation and storage. To overcome these constraints and enhance OED practicality, new air- and moisture-stable aminopyridinium carboxylate and carbonate precursors were synthesized and thermally activated to generate the potent electron donor in situ. Carboxylate adducts proved to be excellent latent OED systems, enabling the facile and efficient reduction of challenging substrates. Their reduction properties were correlated to their structural characteristics by thermogravimetric and spectroscopic analysis.
Electrosynthesis of imidazolium carboxylates
De Robillard, Guillaume,Devillers, Charles H.,Kunz, Doris,Cattey, Helene,Digard, Eric,Andrieu, Jacques
supporting information, p. 4410 - 4413 (2013/09/24)
Synthesis of imidazolium carboxylate compounds was efficiently achieved by electrochemical reduction of imidazolium precursors under very mild conditions.
Ionic liquids as benign catalysts for the carbonylation of amines to formamides
Choi, Young-Seop,Shim, Yu Na,Lee, Jeesun,Yoon, Jung Hee,Hong, Chang Seop,Cheong, Minserk,Kim, Hoon Sik,Jang, Ho Gyeom,Lee, Je Seung
experimental part, p. 87 - 92 (2012/02/05)
1-Butyl-3-methylimidazolium hydrogen carbonate ([BMIm][HCO3]), prepared from the reaction of [BMIm]Cl with K2CO3 in methanol, exhibits high activity for the carbonylation of amines to produce formamides. Computational calculation results on the carbonylation reaction of methylamine implies that such high activity of [BMIm][HCO3] could be ascribed to the bi-functional actions of [HCO3]- as a hydrogen atom acceptor and a donor.
A systematic investigation of factors influencing the decarboxylation of imidazolium carboxylates
Van Ausdall, Bret R.,Glass, Jeremy L.,Wiggins, Kelly M.,Aarif, Atta M.,Louie, Janis
scheme or table, p. 7935 - 7942 (2010/01/16)
(Chemical Equation Presented) A series of 1,3-disubstituted-2-imidazolium carboxylates, an adduct of CO2 and N-heterocyclic carbenes, were synthesized and characterized using single crystal X-ray, thermogravimetric, IR, and NMR analysis. The TG
