Unexpected Intrinsic Lability of Thiol-Functionalized Carboxylate Imidazolium Ionic Liquids
| Autor: | Cinzia Chiappe, Felicia D'Andrea, Lorenzo Poderelli, Christian Silvio Pomelli, Lorenzo Guazzelli, Andrea Mezzetta |
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| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Models
Molecular Magnetic Resonance Spectroscopy Sulfide Carboxylic Acids Side reaction imidazole 2-thione Ionic Liquids Pharmaceutical Science thiol-functionalized ionic liquids Redox Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound redox systems lcsh:Organic chemistry Drug Discovery Polymer chemistry Imidazole Sulfhydryl Compounds Phosphonium Carboxylate Physical and Theoretical Chemistry Density Functional Theory chemistry.chemical_classification Molecular Structure Communication Organic Chemistry Imidazoles thermal-promoted decomposition chemistry Chemistry (miscellaneous) Ionic liquid Thiol Molecular Medicine Oxidation-Reduction |
| Zdroj: | Molecules, Vol 24, Iss 19, p 3571 (2019) Molecules |
| Popis: | New thiol-functionalized carboxylate ionic liquids (ILs), varying both for the cation and for the anion structures, have been prepared as new potential redox switching systems by reacting either 3-mercapto propionic acid (3-MPA) or N-acetyl-cysteine (NAC) with commercially available methyl carbonate ILs. Different ratios of thiol/disulfide ILs were obtained depending both on the acid employed in the neutralization reaction and on the reaction conditions used. Surprisingly, the imidazolium ILs displayed limited thermal stability which resulted in the formation of an imidazole 2-thione and a new sulfide ionic liquid. Conversely, the formation of the imidazole 2-thione was not observed when phosphonium disulfide ILs were heated, thus confirming the involvement of the imidazolium ring in an unexpected side reaction. An insight into the mechanism of the decomposition has been provided by means of DFT calculations. |
| Databáze: | OpenAIRE |
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