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diphenylketene
Sign in to saveDiphenylketene is a chemical substance of the ketene family. Diphenylketene, like most stable disubstituted ketenes, is a red-orange oil at room temperature and pressure. Due to the successive double bonds in the ketene structure R1R2C=C=O, diphenyl ketene is a heterocumulene. The most important reaction of diphenyl ketene is the [2+2] cycloaddition at C-C, C-N, C-O, and C-S multiple bonds.
Chemical data
- Formula
- C14H10O
- Molecular weight
- 194.23 g/mol
- IUPAC name
- 2,2-diphenylethenone
- SMILES
- C1=CC=C(C=C1)C(=C=O)C2=CC=CC=C2
- InChIKey
- ZWJPCOALBPMBIC-UHFFFAOYSA-N
- XLogP
- 4.2
- Polar surface area
- 17.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 194.073
Show 3 more facts
- canonical SMILES
- C1=CC=C(C=C1)C(=C=O)C2=CC=CC=C2
- chemical formula
- C₁₄H₁₀O
- Commons category
- Diphenylketene
Sources (2)
via Wikidata · CC0
~6 min read
Encyclopedic overview
6 sectionsContents
- History
- Preparation
- Properties
- Reactivity
- Application
- References
Diphenylketene is a chemical substance of the ketene family. Diphenylketene, like most stable disubstituted ketenes, is a red-orange oil at room temperature and pressure. Due to the successive double bonds in the ketene structure R1R2C=C=O, diphenyl ketene is a heterocumulene. The most important reaction of diphenyl ketene is the [2+2] cycloaddition at C-C, C-N, C-O, and C-S multiple bonds.
==History== Diphenyl ketene was first isolated by Hermann Staudinger in 1905 and identified as the first example of the exceptionally reactive class of ketenes with the general formula R1R2C=C=O (R1=R2=phenyl group).
Excerpted from Wikipedia’s “diphenylketene” article, available under the CC BY-SA 4.0 licence.