Naphthalene cation radicals, predominant

Oxidation of naphthalene (xii) and durene (xiii) was investigated in [C2mim] [N(Tf)2], [C4mim][N(Tf)2], [C4mim][PF6], and [Ni,8,8,8][N(Tf)2] ILs [10], An irreversible electrochemical process was detected for xii. Similar results are commonly observed in molecular solvents, where the reactivity of the radical cation of a polyaromatic hydrocarbon is known to decrease with the size of the aromatic hydrocarbon [10]. Less delocalized cation radicals of alkylbenzenes, like the one obtained from xiii, are known to display a different reactivity due to the C-H acidity, and the deprotonation from the cation radical is the predominant type of decay (Eq. 11). The nature of the electrochemical mechanism was found to follow the same ECE-DISPl mechanism (DISP = disproportiOTiation) as that in acetonitrile (Eqs. 15.10-15.13) [10]. 

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