Diphenylketene

Diphenylketene

Names
IUPAC name 2,2-Di(phenyl)ethenone
Other names Diphenylethenone
Identifiers
CAS Number	525-06-4 Y
ChemSpider	109691 Y
Jmol interactive 3D	Image Image
PubChem	123069
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
SMILES C1=CC=C(C=C1)C(=C=O)C2=CC=CC=C2 O=C=C(c1ccccc1)c2ccccc2
Properties
Chemical formula	C14H10O
Molar mass	194.23 g·mol−1
Appearance	Red-orange oil
Melting point	8 to 9 °C (46 to 48 °F; 281 to 282 K)
Boiling point	118 to 120 at 1mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

Reactivity

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

Synthesis

Diphenylketene is produced by the elimination of hydrogen chloride from diphenylacetyl chloride in the presence of triethylamine.^[1]

Preparation of Diphenylketene

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 267 nm

IR - charicteristic ketene abs. at 2100 cm⁻¹

References

1. ↑ Submitted by Edward C. Taylor Alexander McKillop, and George H. Hawks. Checked by C. J. Michejda, D. D. von Riesen, R. W. Comnick, and Henry E. Baumgarten. (1972). "DIPHENYLKETENE [Ethenone, diphenyl-]". Organic Syntheses 52: 36. doi:10.15227/orgsyn.052.0036.  line feed character in |authors= at position 71 (help)