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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
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)
via Wikidata · CC0
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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.