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Schickinger, Manuel; Morgenstern, Yvonne; Stierstorfer, Karin; Kornath, Andreas (2017): Protonation of Malononitrile in Superacidic Solutions. In: Zeitschrift für Anorganische und Allgemeine Chemie, Vol. 643, No. 21: pp. 1431-1435
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Malononitrile reacts in superacidic solutions HF/MF5 (M = As, Sb) with formation of the corresponding salts [H2C(CNX)(2)][MF6](2) (M = As, Sb;X = H, D). The occurrence of double protonation is strongly dependent on the stoichiometric ratio of the Lewis acid with regard to malononitrile. Deuterated species were obtained by replacing hydrogen fluoride with deuterium fluoride. The double protonated salts were characterized by vibrational spectroscopy and in the case of [H2C(CNH)(2)][AsF6](2)center dot HF (3) by a single-crystal X-ray structure analysis. The salt crystallizes in the monoclinic space group P2(1)/c with four formula units per unit cell. The vibrational spectra were compared to quantum chemical calculations of the free cation [(CN)H2C(CNH)](+).