Diphenylketene

Diphenylketene

IUPAC name 2,2-Di(phenyl)ethenone
Other names Diphenylethenone
Identifiers
CAS number	525-06-4^Y
PubChem	123069
ChemSpider	109691^Y
Jmol-3D images	Image 1 Image 2
SMILES C1=CC=C(C=C1)C(=C=O)C2=CC=CC=C2 O=C=C(c1ccccc1)c2ccccc2
InChI InChI=1S/C14H10O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H^Y Key: ZWJPCOALBPMBIC-UHFFFAOYSA-N^Y InChI=1/C14H10O/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10H Key: ZWJPCOALBPMBIC-UHFFFAOYAQ
Properties
Molecular formula	C₁₄H₁₀O
Molar mass	194.2286
Appearance	Red/orange oil
Melting point	8–9 °C
Boiling point	118–120 °C at 1mmHg
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Diphenylketene is a chemical of the ketene family. Diphenylketene, like most disubstituted ketenes is a red/orange oil at room temperature and pressure.

Chemistry and reactivity

Diphenylketene can undergo nucleophilic attack from a host of nucleophiles, including alcohols, amines, and enolates with fairly slow rates. These rates can be increased in the presence of various catalysts. At present the mechanism of attack is unknown, but various work is underway to determine the exact mechanism.

Spectroscopic information

¹H NMR - Ar protons only (delta shifts between 7 and 8 ppm, showing 1 doublet and two triplets.

UV/vis - Lambda max at 267nm

IR - charicteristic ketene abs. at 2100 cm^-1