Magnesium anthracene

Magnesium anthracene

File:Magnesium anthracene structure 01.svg
File:GOHRUQ.png
Identifiers
CAS Number	86901-19-1
3D model (JSmol)	Interactive image 3 thf: Interactive image
ChemSpider	3 thf: 9038788
ECHA InfoCard
E number
PubChem CID	21928237 with charge error 3 thf: 10863500
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C14H10.Mg/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1;/h1-10H;/q;+2 Key: UUHXXHJSGPKOGI-UHFFFAOYSA-N 3 thf: InChI=1S/C14H10.3C5H10O.Mg/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1;3*1-2-4-6-5-3-1;/h1-10H;3*1-5H2; Key: RWNAQYFPPNXQES-UHFFFAOYSA-N
SMILES C1=CC=C2C=C3C=CC=CC3=CC2=C1.[Mg] 3 thf: C1CCOCC1.C1CCOCC1.C1CCOCC1.C1=CC=C2C=C3C=CC=CC3=CC2=C1.[Mg]
Properties
Chemical formula	C26H34MgO3
Molar mass	418.860 g·mol−1
Appearance	orange solid
Density	1.184 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Magnesium anthracene is an organomagnesium compound that is almost invariably isolated as its adduct with three tetrahydrofuran (thf) ligands. With the formula Mg(C₁₄H₁₀)(thf)₃, this air- and water-sensitive orange solid is obtained by heating a suspension of magnesium in a thf solution of anthracene.

Structure and reactivity

According to X-ray crystallography, the Mg center is 5-coordinate, occupying a C₂O₃ ligand sphere. The fold angle between the two benzo groups is 72.6°.

The compound behaves as a source of the carbanion [C₁₄H₁₀]^2- as well as a source of highly reactive Mg. With electrophiles, the compound reacts to give dihydroanthracene derivatives C₁₄H₁₀E₂. Electrophiles include ketones, CO₂, organotin chlorides, and organoaluminium chlorides. Ethylene inserts into one Mg-C bond. Hydrogen induces release of anthracene, yielding magnesium hydride (MgH₂).