There are also other types of interactions that generalize the idea of interacting p orbitals in a conjugated system.  The concept of hyperconjugation holds that certain σ bonds can also delocalize into a low-lying unoccupied orbital of a π system or an unoccupied p orbital. Hyperconjugation is commonly invoked to explain the stability of alkyl substituted radicals and carbocations. Hyperconjugation is less important for species in which all atoms satisfy the octet rule, but a recent computational study supports hyperconjugation as the origin of the increased stability of alkenes with a higher degree of substitution (Zaitsev's rule).
Homoconjugation is an overlap of two π-systems separated by a non-conjugating group, such as CH. Unambiguous examples are comparatively rare in neutral systems, due to a comparatively minor energetic benefit that is easily overridden by a variety of other factors; however, they are common in cationic systems in which a large energetic benefit can be derived from delocalization of positive charge (see the article on homoaromaticity for details.). Neutral systems generally require constrained geometries favoring interaction to produce significant degrees of homoconjugation. In the example below, the carbonyl stretching frequencies of the IR spectra of the respective compounds demonstrate homoconjugation, or lack thereof, in the neutral ground state molecules.
Due to the partial π character of formally σ bonds in a cyclopropane ring, evidence for transmission of "conjugation" through cyclopropanes has also been obtained.
Two appropriately aligned π systems whose ends meet at right angles can engage in spiroconjugation.
Vinylogy is the extension of a functional group through a conjugated organic bonding system, which transmits electronic effects.