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Schickinger, Manuel; Zischka, Florian; Stierstorfer, Karin and Kornath, Andreas (2019): Investigation of Malonic Acid in Superacidic Solutions. In: European Journal of Organic Chemistry, Vol. 2019, No. 9: pp. 1876-1882

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Abstract

Malonic acid reacts with the superacidic solutions XF/MF5 (X = H, D;M = As, Sb) to form their corresponding salts [(OH)(2)CCH2C(O)OH][MF6] and [(OH)(2)CCH2C(OH)(2)][MF6](2). The hexafluoridometalates of the mono- and diprotonated malonic acid have been characterized by vibrational spectroscopy and single-crystal X-ray structure analyses. Monoprotonated malonic acid, [(OH)(2)CCH2C(O)OH][AsF6], crystallizes in the orthorhombic space group Pbca with eight formula units per unit cell: a = 9.6739(4) angstrom, b = 11.8355(5) angstrom, c = 13.9826(6) angstrom, and diprotonated malonic acid, [(OH)(2)CCH2C(OH)(2)][AsF6](2), crystallizes in the monoclinic space group P2(1)/n with four formula units per unit cell: a = 7.3348(2) angstrom, b = 9.8437(3) angstrom, c = 16.6903(6) angstrom, beta = 97.818(3)degrees. The experimental data are compared to quantum chemical calculations at the MP2/aug-cc-pVTZ-level of theory for the free cations [(OH)(2)CCH2C(O)OH](+) and [(OH)(2)CCH2C(OH)(2)](2+). A six-membered ring-like structure containing an intramolecular hydrogen bond was found for the monoprotonated species of malonic acid.

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