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cyclooctyne
Sign in to saveCyclooctyne is the cycloalkyne with a formula . Its molecule has a ring of 8 carbon atoms, connected by seven single bonds and one triple bond.
In the Vinony graph
Within Vinony's link graph, cyclooctyne is referenced by 107 other articles, and connects out to pentene, carbon and methane.
It is catalogued under topics including Cycloalkynes and Eight-membered rings.
Its subject is documented across 4 Wikipedia language editions.
Chemical data
- Formula
- C8H12
- Molecular weight
- 108.18 g/mol
- IUPAC name
- cyclooctyne
- SMILES
- C1CCCC#CCC1
- InChIKey
- ZPWOOKQUDFIEIX-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 108.094
Show 3 more facts
- chemical formula
- C₈H₁₂
- canonical SMILES
- C1CCCC#CCC1
- Commons category
- Cyclooctyne
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
Cyclooctyne is the cycloalkyne with a formula . 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 or nitrones, forming triazoles or isoxazolines, respectively.
Excerpted from Wikipedia’s “cyclooctyne” article, available under the CC BY-SA 4.0 licence.