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The electrochemical behavior of aniline derivatives relies on the availability of the lone pair of electrons on the NH2 moiety to be in conjugation with the aryl π-system rendering the aromatic molecule electron-rich. Upon binding to Lewis acids, the nitrogen becomes quartenary and its lone pair of electrons is less energetically accessible. As will be detailed elsewhere, the oxidation potentials of the protonated ligand [H2(pzAnMe, BF4) and even that of the cationic [Me2C(N,N-pzAnMe, BF4, with an sp2-hybridized amino nitrogen) occur above 2.3 V
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