A Quantitative Study of the Halogenophilic Nucleophilic Substitution (S2X) Reaction and Chalcogenophilic Nucleophilic Substitution (S2Ch) Reaction.

Halogenophilic nucleophilic substitution (S2X) has a distinctly different reaction pathway compared to the bimolecular nucleophilic substitution reaction (S2), but they can lead to the same reaction product. However, their differences can be distinguished by studying stereoselective reactions in which both reaction pathways are possible. Herein, we utilize the stereospecific nature of S2 and the presence of a pro-chiral anion intermediate in S2X to conduct a quantitative study in which both S2 and S2X reactions exist.