Structural Motifs in Enantiopure Halogenated Aryl Benzyl Sulfoxides: Effect of Fluorine Substitution

A series of enantiopure crystalline
aryl benzyl sulfoxides, bearing
different substituents on both the aryl groups, were synthesized by
an enantioselective oxidation of the corresponding sulfides. Structural
investigations, achieved by means of single-crystal X-ray diffraction,
allowed us to recognize the main assembling interactions. The same
procedure was repeated for some corresponding fluorinated aryl benzyl
sulfoxides. The synthesis of the enantiomers of a new fluorinated
compound, which shows unusual structural patterns, prompted us to
compare the structural motifs of the two families of sulfoxides (fluorinated
and unfluorinated) and to investigate the changes due to the fluorine
substitution. Some short contacts involving the fluorine atom were
discussed in more details, taking into account the recent interest
in these sometimes controversial interactions.