Spiroaromaticity

Spiroaromaticity in organic chemistry refers to a special case of aromaticity in which conjugation is interrupted by a single spiroatom. Although this spiro center disrupts the continuous overlap of p-orbitals, traditionally thought to be a requirement for aromaticity, considerable thermodynamic stability and many of the spectroscopic, magnetic, and chemical properties associated with aromatic compounds are still observed for such compounds.

References

Chemical bonds

Intramolecular
("strong")

Covalent bond

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 bond Bent bond Dipolar bond Pi backbond Charge-shift bond Hapticity Conjugation Hyperconjugation Antibonding

Resonant bonding	Electron deficiency 3c–2e 4c–2e Hypercoordination 3c–4e Aromaticity möbius super sigma homo spiro σ-bishomo spherical Y-

Metallic bonding

Metal aromaticity

Ionic bonding

Intermolecular
("weak")

van der Waals forces	London dispersion force

Hydrogen bond	Low-barrier Resonance-assisted Symmetric Dihydrogen bonds C–H···O interaction

Other noncovalent	Mechanical bond Halogen bond Aurophilicity Intercalation Stacking Cation–pi bond Anion–pi bond Salt bridge

Concepts in organic chemistry

Aromaticity Covalent bonding Functional groups Nomenclature Organic compounds Organic reactions Organic synthesis Publications Spectroscopy Stereochemistry List of organic compounds

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Spiroaromaticity

See also

References