Azonine

Names
Preferred IUPAC name (2Z,4Z,6Z,8Z)-1H-Azonine
Identifiers
CAS Number	293-57-2 Y
3D model (JSmol)	Interactive image
ChemSpider	10417810 Y
PubChem CID	13287582
CompTox Dashboard (EPA)	DTXSID90534844
InChI InChI=1S/C8H9N/c1-2-4-6-8-9-7-5-3-1/h1-9H Key: HWGJWYNMDPTGTD-UHFFFAOYSA-N
SMILES C1=CC=CNC=CC=C1
Properties
Chemical formula	C8H9N
Molar mass	119.167 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Azonine is an unsaturated heterocycle of nine atoms, with a nitrogen replacing a carbon at one position.^[1] A variety of derivatives have been synthesised.^[2] 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.^[1]

1. ^ ^{a b} Somers, K. R. F.; Kryachko, E. S.; Ceulemans, A. (2004). "Azonine, a "Nearly" Forgotten Aromatic Molecule". The Journal of Physical Chemistry A. 108 (18): 4059–4068. Bibcode:2004JPCA..108.4059S. doi:10.1021/jp037046+. ISSN 1089-5639.
2. ^ Chiang, Chian C.; Paul, Iain C.; Anastassiou, A. G.; Eachus, S. W. (1974). "Molecular structure of an N-substituted azonine. Demonstration of polyenic character in a member of this class of compounds". Journal of the American Chemical Society. 96 (5): 1636–1638. doi:10.1021/ja00812a082. ISSN 0002-7863.

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