Magnesium anthracene

Magnesium anthracene
Identifiers
CAS Number
  • 86901-19-1
3D model (JSmol)
  • Interactive image
  • 3 thf: Interactive image
ChemSpider
  • 3 thf: 9038788
ECHA InfoCard 100.210.465 Edit this at Wikidata
PubChem CID
  • 21928237 with charge error
  • 3 thf: 10863500
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
  • 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
Chemical compound

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.[1]

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°.[2]

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).[1]

References

  1. ^ a b Borislav Bogdanovic (1988). "Magnesium Anthracene Systems and Their Application in Synthesis and Catalysis". Accounts of Chemical Research. 21 (7): 261–267. doi:10.1021/ar00151a002.
  2. ^ L. M. Engelhardt; S. Harvey; C. L. Raston; A. H. White (1988). "Organomagnesium Reagents: The Crystal Structures of [Mg(anthracene)(THF)3] and [Mg(triphenylmethyl)Br(OEt2)2]". Journal of Organometallic Chemistry. 341 (1–3): 39. doi:10.1016/0022-328X(88)89061-2.