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Steiner, Sebastian ORCID logoORCID: https://orcid.org/0000-0002-5286-3567; Djordjevic, Kristina; Bockmair, Valentin ORCID logoORCID: https://orcid.org/0009-0007-4048-6374; Hollenwäger, Dirk und Kornath, Andreas J. ORCID logoORCID: https://orcid.org/0000-0002-7307-4516 (2024): Protonated oxalyl chloride and the ClCO+ cation. In: Acta Crystallographica Section C Structural Chemistry, Bd. 80, Nr. 12: S. 792-797 [PDF, 2MB]

Abstract

The reactions of oxalyl chloride were investigated in the binary superacidic systems HF/SbF5 and DF/SbF5. O-Monoprotonated oxalyl chloride was isolated and represents the first example of a protonated acyl chloride. Diprotonated oxalyl chloride is only stable in solution. Salts of the ClCO+ cation were synthesized from the reactions of oxalyl chloride or COClF with SbF5 in 1,1,1,2- tetrafluoroethane (R-134a, CF3CFH2). The colourless salts were characterized by low-temperature vibrational spectroscopy, NMR spectroscopy and singlecrystal X-ray diffraction (1,2-Dichloro-2-oxoethylidene) oxidanium hexafluoridoantimonate(V), [C2O(OH)Cl2][SbF6], crystallizes in the monoclinic space group P21 and carbonyl chloride hexadecafluoridotriarsenate(V) [ClCO]-[Sb3F16], in the trigonal space group P31, with two and three formula units per unit cell, respectively. Monoprotonated oxalyl chloride and the ClCO+ cation both display very short C—Cl bonds with a strong double-bond character.

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