Correlation between the Basicity of Carbanions and Their Ability to Transfer an Electron

Article abstract of DOI:10.1021/jo00318a043

In Me2SO solution electron transfer from 9-arylfluorenyl carbanions, 9-ArFl^-, to electron acceptors including PhSO2CH2Br, PhSO2CH2I, or R2C(NO2)2 follows second-order kinetics and results in the formation of dimers, (9-ArFl-)2, in high yields.Broensted-type correlations of log k₂ vs. pK_a (Table I) show that these electron-transfer processes have a much higher sensitivity to changes in 9-ArFl^- ion basicity (β_Nu>1.0) than do S_N2 reactions of RX with these carbanions (β_Nu=0.3-0.5).