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| Naji, M. |
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| Motta, Antonella |
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| Aletan, Dirar |
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| Mohamed, Tarek |
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| Ertürk, Emre |
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| Taccardi, Nicola |
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| Kononenko, Denys |
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| Petrov, R. H. | Madrid |
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| Alshaaer, Mazen | Brussels |
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| Bih, L. |
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| Casati, R. |
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| Muller, Hermance |
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| Kočí, Jan | Prague |
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| Šuljagić, Marija |
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| Kalteremidou, Kalliopi-Artemi | Brussels |
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| Azam, Siraj |
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| Ospanova, Alyiya |
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| Blanpain, Bart |
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| Ali, M. A. |
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| Popa, V. |
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| Rančić, M. |
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| Ollier, Nadège |
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| Azevedo, Nuno Monteiro |
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| Landes, Michael |
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| Rignanese, Gian-Marco |
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Thoms, Erik
Université Libre de Bruxelles
in Cooperation with on an Cooperation-Score of 37%
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article
Chemical Variants of the Dicyanamide Anion, and a Landscape for Basic and Superbasic Ionic Liquids
Abstract
<jats:p>We describe the properties of three new aprotic ionic liquids (ILs) with irreducible cations and anions which are close relatives of the commonly used <jats:sup>−</jats:sup>N(CN)<jats:sub>2</jats:sub> anion, namely <jats:sup>−</jats:sup>N(CHO)<jats:sub>2</jats:sub> (diformylamide) and <jats:sup>−</jats:sup>N(CO)<jats:sub>2</jats:sub>(CH<jats:sub>2</jats:sub>)<jats:sub>2</jats:sub> (succinimide), having p<jats:italic>K</jats:italic><jats:sub>a</jats:sub> values which are slightly more basic than the p<jats:italic>K</jats:italic><jats:sub>a</jats:sub> of OH<jats:sup>−</jats:sup> ions of aqueous solution chemistry. In addition to using the well-known <jats:italic>N</jats:italic>-butyl-<jats:italic>N</jats:italic>-methyl pyrrolidinium cation, P<jats:sub>14</jats:sub><jats:sup>+</jats:sup>, we report the use of the tetrabutylammonium cation, <jats:sup>+</jats:sup>N[CH<jats:sub>3</jats:sub>(CH<jats:sub>2</jats:sub>)<jats:sub>3</jats:sub>]<jats:sub>4</jats:sub>, in forming an ionic liquid with the diformylamide anion. The formation and purity of these ILs was assessed by <jats:sup>1</jats:sup>H NMR spectroscopy. The broadband dielectric spectra for all three ionic liquids were analyzed and the glass transition temperatures (<jats:italic>T</jats:italic><jats:sub>g</jats:sub>) estimated from the dielectric data matched well with those obtained from differential scanning calorimetry. The results demonstrate that pure aprotic ILs with high-p<jats:italic>K</jats:italic><jats:sub>a</jats:sub> equivalent anions can be obtained by metathesis reactions despite their low p<jats:italic>K</jats:italic><jats:sub>a</jats:sub> difference of 2 to 3. By contrast, protic analogues of these cation-anion pairs would fail to produce ILs, for which larger p<jats:italic>K</jats:italic><jats:sub>a</jats:sub> differences are required. These new aprotic ILs are glass-forming with <jats:italic>T</jats:italic><jats:sub>g</jats:sub>’s near 210 K and show DC-conductivities near 0.1 mS cm<jats:sup>−1</jats:sup> at ambient temperatures.</jats:p>