Superaromaticity

Superaromaticity is the extra stable nature of some aromatic macrocycle compounds.^[1] These structures contain a number of aromatic rings.

References

↑ Aihara, Jun-ichi (2003), "Hückel-like rule of superaromaticity for charged paracyclophanes", Chemical Physics Letters, 381 (1-2): 147–153, doi:10.1016/j.cplett.2003.09.114

By symmetry	Sigma (σ) Pi (π) Delta (δ) Phi (φ)
By multiplicity	1 (single) 2 (double) 3 (triple) 4 (quadruple) 5 (quintuple) 6 (sextuple)
Miscellaneous	Agostic Bent Coordinate (dipolar) Pi backbond Charge-shift Hapticity Conjugation Hyperconjugation Antibonding
Resonant	Electron deficiency 3c–2e 4c–2e Hypercoordination 3c–4e Aromaticity möbius super sigma homo spiro σ-bishomo spherical Y-

van der Waals forces	London dispersion
Hydrogen	Low-barrier Resonance-assisted Symmetric Dihydrogen bonds C–H···O interaction
Noncovalent other	Mechanical Halogen Aurophilicity Intercalation Stacking Cation–pi Anion–pi Salt bridge

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