Is pyridine an aromatic compound?

The 4 conditions a molecule must fulfil in order to be aromatic.

  1. It must be cyclic
  2. every atom around the ring must have an available p-orbital
  3. The number of electrons in the pi system must be 2, 6, 10, 14, 18, or a higher number in the set that increases from 18 in increments of 4 (22, 26, 30…. Etc). We usually abbreviate this as [4n+2] pi electrons.
  4. The molecule must be flat.

The structure of pyridine considerably resembles that of benzene. Pyridine is aromatic based on the following facts.

  • The protons of pyridine display chemical shifts in the NMR spectrum that are typical of aromatic protons.
  • The nitrogen of pyridine is sp2-hybridized and possesses one lone electron pair. This electron pair is located in a sp2 orbital that is parallel to the ring plane.
  • As an aromatic compound, pyridine may participate in electrophilic substitutions as an electrophile.
  • Pyridine is cyclic, conjugated, and has three pi bonds. There is a total of six pi electrons, which is a Huckel number and the molecule is aromatic.

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