Noncovalent Interactions in the Crystal Structures of a Series of Polyfluorinated Diaryldisulfanes S2(Arf)2

A method for the preparation of polyfluorinated diaryldisulfanes using 65% nitric acid as an oxidizing agent was achieved. Crystals of S2(Arf)2 [Arf = 2,3,5,6-tetrafluorophenyl, 4-chloro-2,3,5,6-tetrafluorophenyl, 2,3,5-trifluoro-3,6-bis(trifluoromethyl)phenyl] were produced and characterized by X-ray diffraction (XRD). It turned out that, in the case of Arf = 2,3,5-trifluoro-4,6-bis(trifluoromethyl)phenyl, the resulting S2(Arf)2 was accompanied by S(Arf)2, whose structure was also determined by X-ray diffraction. Noncovalent interactions play a very important role in the structures of such polyfluorinated compounds. Their geometric analysis was carried out, and in the case of S2(Arf)2 (Arf = 2,3,5,6-tetrafluorophenyl, 4-chloro-2,3,5,6-tetrafluorophenyl), the energy of the Cl···S interactions was estimated using quantum chemical calculations.