Can oxygen atoms be regarded as a Lewis acid?

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?


