- hydrocarbon - Structure and bonding
- hydrocarbon - Aromatic hydrocarbons
- chemical bonding - The role of delocalization
- aromatic compound
- heterocyclic compound - The nature of heteroaromaticity
- hydrocarbon - Polycyclic nonaromatic compounds
- hydrocarbon - Annulenes and the Hückel rule
- hydrocarbon - Nonbenzenoid aromatic compounds
Why are aromatic hydrocarbons more stable than simple Lewis structures suggest?
Aromatic hydrocarbons are more stable than simple Lewis structures suggest because those structures fail to account for the phenomenon of resonance and the resulting delocalization of electrons.
In a simple Lewis structure, electrons are depicted as localized in specific double bonds. However, in aromatic compounds like benzene, the electrons are delocalized over the entire ring. Because each electron feels the attractive force of all the carbon nuclei in the ring rather than being restricted to just two, the electrons are more strongly held, which significantly increases the molecule's stability.12
This special stability, known as aromaticity, is associated with planar, cyclic conjugated systems that follow the Hückel rule, which requires the presence of electrons (where is a whole number). Compounds that satisfy these criteria exhibit lower reactivity than expected for unsaturated hydrocarbons, often favoring substitution reactions over the addition reactions typical of alkenes.123