Magnesium anthracene

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Magnesium anthracene
Magnesium anthracene structure 01.svg
GOHRUQ.png
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.210.465 Edit this at Wikidata
  • 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
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).

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[edit]

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[edit]

  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.{{cite journal}}: CS1 maint: uses authors parameter (link)