Abstract
Reversible dimerization of the anion radicals of carbonyl compounds was studied by cyclic voltammetry, chronoamperometry, electrolysis, digital simulation and quantum chemical calculations using electroreduction of 9-fluorenone in DMF/0.1 M Bu4NClO4 as an example. The experimental data confirmed that this reaction is thermodynamically unfavorable as it was predicted by DFT calculations. In contrast with some other anion radicals, neither ion pairing of 9-fluorenone anion radicals with lithium cation nor their hydrogen bonding with water shifts the dimerization equilibrium to the dimeric product. Reversibility of the dimerization decreases in the presence of phenol due to the protonation of the dimeric dianion and to the irreversibility of dimerization of the anion radical – phenol complexes. The contribution of these two pathways to general hydrodimerization process is discussed.
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