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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.
In the Vinony graph
Within Vinony's link graph, 2,5-norbornadiene is referenced by 39 other articles, and connects out to Diels–Alder reaction, mass density and solar energy.
Vinony files it under Bicyclic compounds, Chembox having GHS data and Chembox image size set.
Its subject is documented across 20 Wikipedia language editions.
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.