Term: homoaromatic
https://doi.org/10.1351/goldbook.H02839

Definition:
Whereas in an aromatic molecule there is continuous overlap of p-orbitals over a cyclic array of atoms, in a homoaromatic molecule there is a formal discontinuity in this overlap resulting from the presence of a single sp 3 hybridized atom at one or several positions within the ring; p-orbital overlap apparently bridges these sp 3 centres, and features associated with aromaticity are manifest in the properties of the compound. Pronounced homoaromaticity is not normally associated with neutral molecules, but mainly with species bearing an electrical charge, e.g. the 'homotropylium' cation, (C8H9+): H02839.png In bis, tris, (etc.) homoaromatic species, two, three, (etc.) single sp 3 centres separately interrupt the π-electron system.

Related Terms:
1) homoconjugation (note. 2) (http://doi.org/10.1351/goldbook.H02842).
2) aromatic (http://doi.org/10.1351/goldbook.A00441).
3) aromaticity (http://doi.org/10.1351/goldbook.A00442).
4) cation (http://doi.org/10.1351/goldbook.C00907).

Image: Not defined (https://goldbook.iupac.org/img/inline/H02839.png) 

Source: PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1121 (https://doi.org/10.1351/pac199466051077)

Citation: 'homoaromatic' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. https://doi.org/10.1351/goldbook.H02839

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