Conjugated System - Mechanism

Mechanism

Conjugation is possible by means of alternating single and double bonds. As long as each contiguous atom in a chain has available a p-orbital, the system can be considered conjugated. For example, furan (see picture) is a five-membered ring with two alternating double bonds and an oxygen in position 1. Oxygen has two lone pairs, one of which occupies a p-orbital on that position, thereby maintaining the conjugation of that five-membered ring. The presence of a nitrogen in the ring or groups α to the ring like a carbonyl group (C=O), an imine group (C=N), a vinyl group (C=C), or an anion will also suffice as a source of pi orbitals to maintain conjugation.

There are also other ways of conjugation. Homoconjugation is an overlap of two π-systems separated by a non-conjugating group, such as CH₂. For example, the molecule CH₂=CH–CH₂–CH=CH₂ (1,4-pentadiene) is homoconjugated because the two C=C double bonds (which are π-systems because each double bond contains one π bond) are separated by one CH₂ group.