25965-81-5Relevant academic research and scientific papers
Versatile Method for the Simultaneous Synthesis of Two Ionic Liquids, Otherwise Difficult to Obtain, with High Atom Economy
Szpecht, Andrea,Zajac, Adrian,Zielinski, Dawid,Maciejewski, Hieronim,Smiglak, Marcin
, p. 972 - 983 (2019)
A new synthetic approach and full spectral (NMR, IR, MS) and ion chromatographic characterization (IC) of nitrogen-based ionic liquids bearing allyl- or ethyl- substituent and triflate, tosylate, methyl sulfate or methanesulfonate anion has been presented. On a sample of 16 new ionic liquids, the versatility of the anion exchange method has been proven. In the metathesis reactions that have been carried out, the halide anion was exchanged in ionic liquid with an alkyl sulfonate based anion using alkylating agents. The results obtained using ion chromatographic analysis on the newly synthesized compounds have been discussed. Also, the utilization of a gaseous methyl halide by-product, obtained in the metathesis reaction and otherwise difficult to synthesize, has been presented. This approach ensured high atom economy of the overall process, which makes the proposed methodology sustainable and eco-friendly.
Synthesis and characterization of nitrogen-based ionic liquids bearing allyl groups and examples of their application
Zajac, Adrian,Szpecht, Andrea,Szymanska, Anna,Zielinski, Dawid,Stolarska, Olga,Smiglak, Marcin,Maciejewski, Hieronim
, p. 12274 - 12288 (2020/07/30)
The syntheses and full spectral (NMR, MS, and IR), thermal (DSC) and ion chromatographic characterization of two series of amine-derived ionic liquids bearing allyl substituents and having chloride or bis(trifluoromethanesulfonyl)amide anions have been presented. The analysis of the dependence of the 1H NMR chemical shift values of the selected protons on the cation and anion structure has been conducted. DSC analysis records together with ion chromatography analysis results have been presented and interpreted. Moreover, a selection of obtained chloride ionic liquids have been transformed into the corresponding chlorocobaltates and chlorozincates or used as substrates in thiol-ene click reactions to indicate their potential as precursors of catalysts or various surface modifiers.
Synthesis and evaluation of influenza A viral neuraminidase candidate inhibitors based on a bicyclo[3.1.0]hexane scaffold
Colombo, Cinzia,Pinto, B. Mario,Bernardi, Anna,Bennet, Andrew J.
, p. 6539 - 6553 (2016/07/16)
This manuscript describes a novel class of derivatives based on a bicyclo[3.1.0]hexane scaffold, proposed as mimics of sialic acid in a distorted boat conformation that is on the catalytic pathway of neuraminidases (sialidases). A general synthetic route for these constrained-ring molecules was developed using a photochemical reaction followed by a Johnson-Corey-Chaykovsky cyclopropanation. Functionalization with the goal of occupying the 150-cavity was also exploited. Inhibition assays demonstrated low micromolar inhibition against both group-1 (H5N1) and group-2 (H9N2) influenza neuraminidase subtypes, indicating good affinity for the alpha and beta sialic acid mimics and 150-cavity-targeted derivatives. These results provide a validation of a bicyclo[3.1.0]hexane scaffold as a mimic of a distorted sialic acid bound in the neuraminidase active site during catalysis.
Ionic liquids as solvents for rhodium and platinum catalysts used in hydrosilylation reaction
Zielinski, Witold,Kukawka, Rafal,Maciejewski, Hieronim,Smiglak, Marcin
, (2016/09/23)
A group of imidazolium and pyridinium based ionic liquids has been synthetized, and their ability to dissolve and activate the catalysts used in hydrosilylation reaction of 1-octane and 1,1,1,3,5,5,5-heptamethyltrisiloxane was investigated. An organometallic catalyst as well as inorganic complexes of platinum and rhodium dissolved in ionic liquids were used, forming liquid solutions not miscible with the substrates or with the products of the reaction. The results show that application of such a simple biphasic catalytic system enables reuse of ionic liquid phase with catalysts in multiple reaction cycles reducing the costs and decreasing the amount of catalyst needed per mole of product.
