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Steiner, Sebastian ORCID logoORCID: https://orcid.org/0000-0002-5286-3567; Shafiq, Zurwa M.; Nitzer, Alexander; Hollenwäger, Dirk and Kornath, Andreas J. ORCID logoORCID: https://orcid.org/0000-0002-7307-4516 (2024): HF-addition to haloacetyl fluorides in superacidic media. In: New Journal of Chemistry, Vol. 48, No. 31: pp. 13846-13853 [PDF, 1MB]

Abstract

The reactions of difluoroacetyl fluoride and trifluoroacetyl fluoride were investigated in the binary superacid HF/SbF5 by low-temperature NMR spectroscopy. Whereas both haloacetyl fluorides form oxonium species after the addition of HF, the protonated acyl fluorides were not observed. Protonated 1,1,2,2-tetrafluoroethanol was isolated as a solid and represents an example of a protonated α-fluoroalcohol. The salt was characterized by low-temperature vibrational spectroscopy and single-crystal X-ray diffraction. [CHF2CF2OH2][SbF6] crystallizes in the triclinic space group P[1 with combining macron] with two formula units per unit cell. Protonated perfluoroethanol is only stable in solution. The reactivity of both haloacyl fluorides is discussed based on quantum chemical calculations at the MP2/aug-cc-pVTZ-level of theory.

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