HF-addition to haloacetyl fluorides in superacidic media.

Autor: Steiner, Sebastian, Shafiq, Zurwa M., Nitzer, Alexander, Hollenwäger, Dirk, Kornath, Andreas J.
Zdroj: New Journal of Chemistry; 8/21/2024, Vol. 48 Issue 31, p13846-13853, 8p
Abstrakt: 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 P1¯ 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index