Azonine is an unsaturated

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

of nine atoms, with a

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

replacing a

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

at one position. A variety of derivatives have been synthesised. It is considered to possess a considerable amount of aromatic stability. It and C₉H₉^– are the largest monocyclic all-''cis'' ring systems to be aromatic and close to planar. Due to a balance between angle strain (~20°) and aromaticity, a planar conformation and distorted conformation are very close in energy and the two are observable as an equilibrium mixture in the solution phase in acetone. Furthermore, the presence of substituents or nearby cations strongly influences the conformation.

References

Nitrogen heterocycles Simple aromatic rings Heterocyclic compounds with 1 ring Nine-membered rings {{Heterocyclic-stub

See also

References