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Experiments and Calculations for Determination of the Stabilities of Benzyl, Benzhydryl, and Fluorenyl Carbocations: Antiaromaticity Revisited

The following pK R values for the formation of benzyl, benzhydryl, and fluorenyl carbocations in 50:50 (v:v) trifluoroethanol/water at I=0.50 (NaClO 4 ) were determined as pK R =-log (k HOH [H 2 O]/k H ), where k H is the second-order rate constant for acid-catalyzed reaction of the alcohol to form the carbocation and k HOH is the second-order rate constant for capture of the carbocation by water