Although both oxidants and Lewis acids can steal electrons, they work in different ways. Oxidants acquire electrons via ionic bonds or polar covalent bonds, while Lewis acids form dative bonds with lone electron pairs. As a result, redox reactions are generally not considered acid base reactions. However, in some rare cases oxygen atoms can form dative bonds with lone pairs. For example, trimethylamine can donate a lone pair to an oxygen atom and become TMAO. Does that mean the oxygen atom acts as a Lewis acid in TMAO? And what’s the Lewis acidity of oxygen atoms?

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    $\begingroup$ Reactions with radicals such as O or O2 can be written as acid-base reactions but the mechanism is more likely radical single electron transfers rather than dative electron pair transfer or sharing. Some reactions of oxidizing agents such as I2, Br2 and even Cl2 such as the Friedel Grafts reaction or the halogenation of carbon double or triple bonds do have a Lewis acid mechanism; the reaction does not involve radicals. $\endgroup$
    – jimchmst
    May 1, 2022 at 2:47


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