Arenium Ion Intermediate

An arenium ion intermediate is a short-lived, resonance-stabilized carbocation formed when an electrophile adds to an aromatic ring, making it a central species in electrophilic aromatic substitution. During this step, the attacked carbon changes from sp2 to sp3 hybridization and aromaticity is temporarily disrupted, while the positive charge is delocalized across the ring; loss of a proton then restores the aromatic system. This intermediate helps explain reactions such as nitration, halogenation, sulfonation, and Friedel–Crafts alkylation or acylation, including their regioselectivity and the effects of substituents on reaction rates and product distribution.

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JoVE Core - Cell Biology

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Common Ion Effect

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