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cyclooctatetraene
Sign in to saveAlso known as 1,3,5,7-cyclooctatetraene, cycloocta-1,3,5,7-tetraene, COT, [8]-annulene, (Z,Z,Z,Z)-1,3,5,7-cyclooctatetraene
1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane. It is a colorless flammable liquid at room temperature. COT is an antiaromatic compound as it possesses 8 π electrons. In contrast to the aromaticity commonly seen in benzene rings; antiaromaticity destabilises the COT molecule. This destabilisation effect is so strong that COT avoids it by adopting a non-planar 'tub' conformation, which prevents all of the π orbitals from forming a single conjugated system. As a result, COT possesses significant polyene character and will undergo many reactions that benzene rings wil
In the Vinony graph
Vinony's link graph records 193 inbound references to cyclooctatetraene, and connects out to aromaticity, aqueous solution and polyene.
It is catalogued under topics including Annulenes, Antiaromatic compounds and Chembox having GHS data.
Vinony links it to 23 Wikipedia language editions.
Chemical data
- Formula
- C8H8
- Molecular weight
- 104.15 g/mol
- IUPAC name
- cyclooctatetraene
- SMILES
- C\1=C\C=C/C=C\C=C1
- InChIKey
- KDUIUFJBNGTBMD-DLMDZQPMSA-N
- XLogP
- 3.1
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
Show 5 more facts
- canonical SMILES
- C1=CC=CC=CC=C1
- chemical formula
- C₈H₈
- Commons category
- Cyclooctatetraene
- isomeric SMILES
- C1=C/C=C\C=C/C=C\1
- melting point
- -5
Sources (2)
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Encyclopedic overview
9 sectionsContents
- History
- Structure and bonding
- Synthesis
- Derivatives
- Natural occurrence
- Reactions
- Cyclooctatetraenide as a ligand and ligand precursor
- See also
- References
1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane. It is a colorless flammable liquid at room temperature. COT is an antiaromatic compound as it possesses 8 π electrons. In contrast to the aromaticity commonly seen in benzene rings; antiaromaticity destabilises the COT molecule. This destabilisation effect is so strong that COT avoids it by adopting a non-planar 'tub' conformation, which prevents all of the π orbitals from forming a single conjugated system. As a result, COT possesses significant polyene character and will undergo many reactions that benzene rings will not. This been the subject of much research and historically some controversy.
==History== 1,3,5,7-Cyclooctatetraene was initially synthesized by Richard Willstätter in Munich in 1905 using pseudopelletierine as the starting material and the Hofmann elimination as the key transformation: class=skin-invert-image|450px|Willstätter's synthesis of cyclooctatetraene (1905).
Excerpted from Wikipedia’s “cyclooctatetraene” article, available under the CC BY-SA 4.0 licence.