Cyclooctyne
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3D model (JSmol)
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| 1209275 | |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C8H12 | |
| Molar mass | 108.184 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclooctyne is the cycloalkyne with a formula C
8H
12. Its molecule has a ring of 8 carbon atoms, connected by seven single bonds and one triple bond.
Cyclooctyne is the smallest cycloalkyne that is stable enough to be isolated, although the chemical is still highly reactive. The alkyne region of the structure attempts to adopt a linear molecular geometry, but the nature of the ring creates substantial ring strain. As a result, cyclooctyne and other compounds containing this ring structure readily react in ways that reduce the ring strain by converting the alkyne to a functional group that does not require linear geometry. An important application of this reactivity is in click chemistry, where cyclooctynes undergo cycloaddition reactions with azides[1] or nitrones,[2] forming triazoles or isoxazolines, respectively.
References
[edit | edit source]External links
[edit | edit source]- Error creating thumbnail: File missing Media related to Lua error in Module:Commons_link at line 62: attempt to index field 'wikibase' (a nil value). at Wikimedia Commons
