Armilenium
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| Names | |
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| IUPAC name
1,2,4a,5,6,8a-Hexahydro-1,2,5-methenonaphthalen-6-ylium
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| Other names
[3.5.3]Armilenium; 9-Tetracyclo[5.4.0.04,5.03,8]undeca-5,10-dienyl cation
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| Identifiers | |
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C11H11+ | |
| Molar mass | [cannot calculate]Expression error: Unexpected < operator |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
Armilenium is a C
11H+
11 carbocation and was originally proposed as the first entirely organic sandwich compound. Named for its resemblance to an armillary sphere, NMR evidence for the carbocation was first described by Melvin J. Goldstein and Stanley A. Klein at Cornell University in 1973.[1][2][3][4][5] In subsequent 13C NMR experiments by Goldstein and Joseph P. Dinnocenzo in 1984, the C
11H+
11 carbocation was generated under stable ion conditions at lower temperature and at higher magnetic field than previously possible.[6] These experiments revealed the carbocation to be fluxional. Fitting of the dynamic NMR process ruled out the sandwich species even as an intermediate in the 20-fold degenerate rearrangement of the carbocation.
References
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- ^ Page Module:Citation/CS1/styles.css has no content.Goldstein MJ, Kline SA (1973). "A C11H11 cation of unusual structure". Journal of the American Chemical Society. 95 (3): 935–936. doi:10.1021/ja00784a058.
- ^ Page Module:Citation/CS1/styles.css has no content.Tennant G (1973). "Molecular rearrangements". Annual Reports on the Progress of Chemistry, Section B: Organic Chemistry. Vol. 70. The Chemical Society. p. 221. doi:10.1039/OC9737000206. ISBN 0-85186-061-3.
- ^ Page Module:Citation/CS1/styles.css has no content.Hogeveen H, Kwant PW (1975). "Pyramidal mono- and dications: Bridge between organic and organometallic chemistry". Accounts of Chemical Research. 8 (12): 413–420. doi:10.1021/ar50096a004.
- ^ Page Module:Citation/CS1/styles.css has no content.Goldstein MJ, Tomoda S, Pressman EJ, Dodd JA (1981). "The automerization of C11H11 chlorides and the stability of their cations". Journal of the American Chemical Society. 103 (21): 6530–6532. doi:10.1021/ja00411a059.
- ^ Page Module:Citation/CS1/styles.css has no content.Ahlberg P, Jonäll G, Engdahl C (1983). "Degenerate carbocation rearrangements". In Gold V, Bethell D (eds.). Advancements in Physical Organic Chemistry. Advances in Physical Organic Chemistry. Vol. 19. Academic Press. pp. 366–367. doi:10.1016/s0065-3160(08)60224-5. ISBN 0-12-033519-0.
- ^ Page Module:Citation/CS1/styles.css has no content.Goldstein MJ, Dinnocenzo JP (1984). "Automerization mechanism and structure of the C11H11 armilenyl cation". Journal of the American Chemical Society. 106 (8): 2473–2475. doi:10.1021/ja00320a062.
