= Electrophilic substitution
An <electrophilic substitution> replaces an atom or group on a substrate through reaction with an <electrophile>. The major organic example is <electrophilic aromatic substitution>, in which an aromatic carbon-hydrogen bond is replaced while the aromatic system is ultimately restored.
In aromatic nitration, attack on an electrophilic nitrogen species forms a nonaromatic intermediate, followed by loss of a proton. The final restoration of <aromaticity> helps explain substitution rather than net addition. The reacting substrate and the identity of the electrophile determine the actual mechanism and site selectivity.
Back to article page
