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Magnesium anthracene is an organomagnesium compound that is almost invariably isolated as its
adduct An adduct (from the Latin ''adductus'', "drawn toward" alternatively, a contraction of "addition product") is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all co ...
with three
tetrahydrofuran Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
(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 Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is co ...
.


Structure and reactivity

According to
X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...
, the Mg center is 5-coordinate, occupying a C2O3 ligand sphere. The fold angle between the two benzo groups is 72.6°.{{cite journal, authors=L. M. Engelhardt, S. Harvey, C. L. Raston, A. H. White, title=Organomagnesium Reagents: The Crystal Structures of g(anthracene)(THF)3and g(triphenylmethyl)Br(OEt2)2journal= Journal of Organometallic Chemistry, year=1988, volume=341, issue=1–3, page=39, doi=10.1016/0022-328X(88)89061-2 The compound behaves as a source of the carbanion 14H10sup>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 Magnesium hydride is the chemical compound with the molecular formula MgH2. It contains 7.66% by weight of hydrogen and has been studied as a potential hydrogen storage medium. Preparation In 1951 preparation from the elements was first reporte ...
(MgH2).


References

Anthracenes Organomagnesium compounds