Aromatic compounds are unusually stable

Aromatic structures are more stable than their open-

chain counterparts. For example, benzene is more stable than 1,3,5-hexatriene

CH2 CH2

To be classified as aromatic, a compound must meet both of the following criteria:

1. It must have an uninterrupted cyclic cloud of pi

electrons (often called a cloud) above and below the plane of the molecule.
For the pi cloud to be cyclic, the molecule must be

cyclic. For the pi cloud to be uninterrupted, every atom in the ring must have a p orbital. For the pi cloud to form, each p orbital must overlap with the p orbitals on either side of it. Therefore, the molecule must be planar.

2. The pi cloud must contain an odd number of pairs of pi electrons.

Huckels Rule or the (4n+2) rule

The rule states that for a planar, cyclic compound to be aromatic, its

uninterrupted cloud must contain (4n+2) pi electrons, where n is any whole number. According to Hckels rule, then, an aromatic compound must have 2 (n=0), 6 (n=1), 10(n=2), 14(n=3), 18(n=4) etc., electrons. Systems with 4n pi electrons, with n an integer, are ANTIAROMATIC. For example cyclobutadiene (4 pi electrons)

Antiaromatic compounds are highly unstable

Aromaticity is characterized by stability, whereas antiaromaticity is

characterized by instability. An antiaromatic compound is planar, cyclic and has an uninterrupted ring of p orbital-bearing atoms, and has an even pair of pi electrons.

CH2 CH2
Less stable More stable

Aromatic Heterocylcic Compounds

Classify each as aromatic, antiaromatic, or nonaromatic

Convince yourselves that these structures are AROMATIC

CH
-

CH

CH

CH CH
-

N H