Structure via PubChem · Public domain (PubChem)
2,5-norbornadiene
Sign in to saveAlso known as norbornadiene, bicyclo[2.2.1]hepta-2,5-diene
Norbornadiene is an organic compound and a bicyclic hydrocarbon. Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. It has been intensively studied owing to its high reactivity and distinctive structural property of being a diene that cannot isomerize (isomers would be anti-Bredt alkenes). Norbornadiene is also a useful dienophile in Diels-Alder reactions.
Chemical data
- Formula
- C7H8
- Molecular weight
- 92.14 g/mol
- IUPAC name
- bicyclo[2.2.1]hepta-2,5-diene
- SMILES
- C1C2C=CC1C=C2
- InChIKey
- SJYNFBVQFBRSIB-UHFFFAOYSA-N
- XLogP
- 2.1
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- bicyclic compound
- Has part
- hydrogen
- Mass
- 92.063
Show 4 more facts
- canonical SMILES
- C1C2C=CC1C=C2
- chemical formula
- C₇H₈
- Commons category
- Norbornadiene
- melting point
- -20.0
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Synthesis
- Reactions
- As a ligand
- See also
- References
Norbornadiene is an organic compound and a bicyclic hydrocarbon. Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. It has been intensively studied owing to its high reactivity and distinctive structural property of being a diene that cannot isomerize (isomers would be anti-Bredt alkenes). Norbornadiene is also a useful dienophile in Diels-Alder reactions.
== Synthesis == Norbornadiene can be formed by a Diels-Alder reaction between cyclopentadiene and acetylene 300px|left|Norbornadiene synthesis
Excerpted from Wikipedia’s “2,5-norbornadiene” article, available under the CC BY-SA 4.0 licence.