In the original meaning a conjugated system is a molecular entity whose structure may be represented as a system of alternating single and multiple bonds: e.g.
CH2=CH–CH=CH2,
CH2=CH–C≡N. In such systems, conjugation is the interaction of one p-orbital with another across an intervening σ-bond in such structures. (In appropriate molecular entities d-orbitals may be involved.) The term is also extended to the analogous interaction involving a p-orbital containing an unshared electron pair, e.g.
:Cl–CH=CH2.
See also: delocalization, homoconjugation, resonance
Source:
PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1099 (https://doi.org/10.1351/pac199466051077)