The Kinetic Acidity of Oligofluorobenzenes Correlated with Their Gas Phase Deprotonation Energies

The relative reactivities of fluorobenzene, all di‐, tri‐, and tetrafluorobenzenes and pentafluorobenzene toward sec ‐butyllithium have been assessed in tetrahydrofuran at −100 °C. At this temperature no subsequent transmetalation reactions take place but those compromise the outcome of the competition experiments if the latter are conducted at −75 °C. The rates determined at −100 °C reflect the basicity differences between the naked (oligo)fluorophenyl anions to the extent of 10 %.