3 years ago

Protonation of Malononitrile in Superacidic Solutions

Protonation of Malononitrile in Superacidic Solutions
Manuel Schickinger, Karin Stierstorfer, Andreas Kornath, Yvonne Morgenstern
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·HF (3) by a single-crystal X-ray structure analysis. The salt crystallizes in the monoclinic space group P21/c with four formula units per unit cell. The vibrational spectra were compared to quantum chemical calculations of the free cation [(CN)H2C(CNH)]+.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/zaac.201700220

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