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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
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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".
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at one position. A variety of derivatives have been synthesised. It is considered to possess a considerable amount of aromatic stability. It and C
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Somers, K. R. F.; Kryachko, E. S.; Ceulemans, A. (2004). "Azonine, a "Nearly" Forgotten
Aromatic Molecule".
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of substituents or nearby cations strongly influences the conformation.
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Except where otherwise noted, data are given for materials in their
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213:Key: HWGJWYNMDPTGTD-UHFFFAOYSA-N
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389:The Journal of Physical Chemistry A
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540:Heterocyclic compounds with 1 ring
483:. You can help Knowledge (XXG) by
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330:are the largest monocyclic all-
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360:(2Z,4Z,6Z,8Z)-Thionine
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475:This article about a
37:Preferred IUPAC name
545:Nine-membered rings
445:10.1021/ja00812a082
401:2004JPCA..108.4059S
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310:is an unsaturated
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409:10.1021/jp037046+
395:(18): 4059–4068.
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68:Identifiers
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312:heterocycle
243:Properties
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371:References
275:Molar mass
120:ChemSpider
96:3D model (
75:CAS Number
453:0002-7863
417:1089-5639
339:See also
316:nitrogen
154:13287582
129:10417810
85:293-57-2
61:-Azonine
17:Azonine
397:Bibcode
365:Oxonine
350:Pyrrole
345:Azepine
308:Azonine
280:119.167
141:PubChem
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320:carbon
227:SMILES
31:Names
479:is a
202:InChI
98:JSmol
481:stub
449:ISSN
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393:108
332:cis
171:EPA
144:CID
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268:N
265:9
262:H
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256:C
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169:(
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59:H
55:Z
51:Z
47:Z
43:Z
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