Electrophile - Superelectrophiles

Superelectrophiles are defined as cationic electrophilic reagents with greatly enhanced reactivities in the presence of superacids. These compounds were first described by George A. Olah. Superelectrophiles form as a doubly electron deficient superelectrophile by protosolvation of a cationic electrophile. As observed by Olah, a mixture of acetic acid and boron trifluoride is able to remove a hydride ion from isobutane when combined with hydrofluoric acid via the formation of a superacid from BF₃ and HF. The responsible reactive intermediate is the CH₃CO₂H₃ dication. Likewise, methane can be nitrated to nitromethane with nitronium tetrafluoroborate NO+
2BF−
4 only in presence of a strong acid like fluorosulfuric acid.

In gitionic (gitonic) superelectrophiles, charged centers are separated by no more than one atom, for example, the protonitronium ion O=N+=O+—H (a protonated nitronium ion). And, in distonic superelectrophiles, they are separated by 2 or more atoms, for example, in the fluorination reagent F-TEDA-BF₄