Magnesium anthracene

Structural formula
General
Surname	Magnesium anthracene
other names	Magnesium anthracene tetrahydrofuran adduct; Bogdanović Magnesium; 9,10-dihydro-9,10-anthracenediyl-tris (tetrahydrofuran) magnesium; Magnesium anthracene dianion; Magnesium anthracene;
Molecular formula	MgC 14 H 10 • 3 C 4 H 8 O
Brief description	orange powder
External identifiers / databases
EC number	685-033-4
ECHA InfoCard	100.210.465
Wikidata	Q19295563
properties
Molar mass	202.54 g mol −1 ; 418.85 g mol −1 as a tetrahydrofuran adduct;
Physical state	firmly
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 250-261
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Magnesium anthracene is a magnesium complex that is sensitive to air and hydrolysis and is usually handled as a tetrahydrofuran adduct. The compound is also known as Bogdanović magnesium.

history

The complex was first presented in 1965 by Hugh E. Ramsden. In the 1980s, Borislav Bogdanović began to systematically examine the complex at the Max Planck Institute for Coal Research in Mülheim an der Ruhr .

While the production of magnesium hydride from the elements requires high hydrogen pressures and high reaction temperatures of 500 ° C, magnesium anthracene can easily be converted into magnesium hydride under mild conditions, which is considered an excellent metal hydride storage device with a high mass-related hydrogen storage capacity.

Presentation and structure

The air- and water-sensitive solid is synthesized by stirring a metallic magnesium suspension in anthracene , tetrahydrofuran and dibromomethane in a temperature range between 20 and 60 ° C. The orange powder is formed in good yields. The pure substance is obtained by washing with tetrahydrofuran. At higher temperatures, the compound breaks down again into the starting materials.

The X-ray shows a five-fold coordinated Mg-center. The angle between the two benzo groups is 72.6 °.

use

The compound can be used both as a source of the carbanion [C ₁₄ H ₁₀ ] ^2– and as a source of highly reactive Mg. The compound reacts with electrophiles such as ketones or carbon dioxide to form dihydroanthracene derivatives of the general formula C ₁₄ H ₁₀ E ₂ . Magnesium anthracene is used, among other things, in solar power plants to store the electrical energy generated as magnesium hydride (MgH ₂ ). Magnesium anthracene is also an alternative to the use of metallic magnesium in the production of Grignard compounds .

Individual evidence

↑ ^a ^b ^c ^d Entry on magnesium anthracene. In: Römpp Online . Georg Thieme Verlag, accessed on December 26, 2014.
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of Magnesiumanthracene tetrahydrofuran complex in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 14, 2016, is reproduced from a self-classification by the distributor .
↑ Patent US3354190 : Magnesium and tin derivatives of fusedring hydrocarbons and the preparation thereof. Filed January 4, 1965 , published November 21, 1967 , Applicant: Exxon Research Engineering Co. , Inventor: Hugh E. Ramsden. ‌
↑ Borislav Bogdanović: Magnesium anthracene systems and their application in synthesis and catalysis. In: Accounts of Chemical Research . 21, 1988, pp. 261-267, doi : 10.1021 / ar00151a002 .
↑ Borislav Bogdanovic, Shih-tsien Liao, Manfred Schwickardi, Peter Sikorsky, Bernd Spliethoff: Catalytic Synthesis of Magnesium Hydride under Mild Conditions. In: Angewandte Chemie International Edition . 19, 1980, pp. 818-819, doi : 10.1002 / anie.198008181 .
↑ Lutz M. Engelhardt, Stephen Harvey, Colin L. Raston, Allan H. White: Organo-magnesium reagents: the crystal structures of [Mg (anthracene) (THF) 3] and [Mg (triphenylmethyl) Br (OEt2) 2] . In: Journal of Organometallic Chemistry. 341, 1988, pp. 39-51, doi: 10.1016 / 0022-328X (88) 89061-2 .
↑ Solar energy - gentle breeder. In: DER SPIEGEL. September 19, 1988. Retrieved December 26, 2014 .
↑ Colin L. Raston, Geoffrey Salem: Magnesium anthracene: an alternative to magnesium in the high yield synthesis of Grignard reagents. In: Journal of the Chemical Society, Chemical Communications . 1984, p. 1702, doi : 10.1039 / C39840001702 .

[roempp-1] Entry on magnesium anthracene. In: Römpp Online . Georg Thieme Verlag, accessed on December 26, 2014.

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of Magnesiumanthracene tetrahydrofuran complex in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 14, 2016, is reproduced from a self-classification by the distributor .

[3] Patent US3354190 : Magnesium and tin derivatives of fusedring hydrocarbons and the preparation thereof. Filed January 4, 1965 , published November 21, 1967 , Applicant: Exxon Research Engineering Co. , Inventor: Hugh E. Ramsden. ‌

[4] Borislav Bogdanović: Magnesium anthracene systems and their application in synthesis and catalysis. In: Accounts of Chemical Research . 21, 1988, pp. 261-267, doi : 10.1021 / ar00151a002 .

[5] Borislav Bogdanovic, Shih-tsien Liao, Manfred Schwickardi, Peter Sikorsky, Bernd Spliethoff: Catalytic Synthesis of Magnesium Hydride under Mild Conditions. In: Angewandte Chemie International Edition . 19, 1980, pp. 818-819, doi : 10.1002 / anie.198008181 .

[LMEngelhardt-6] Lutz M. Engelhardt, Stephen Harvey, Colin L. Raston, Allan H. White: Organo-magnesium reagents: the crystal structures of [Mg (anthracene) (THF) 3] and [Mg (triphenylmethyl) Br (OEt2) 2] . In: Journal of Organometallic Chemistry. 341, 1988, pp. 39-51, doi: 10.1016 / 0022-328X (88) 89061-2 .

[7] Solar energy - gentle breeder. In: DER SPIEGEL. September 19, 1988. Retrieved December 26, 2014 .

[8] Colin L. Raston, Geoffrey Salem: Magnesium anthracene: an alternative to magnesium in the high yield synthesis of Grignard reagents. In: Journal of the Chemical Society, Chemical Communications . 1984, p. 1702, doi : 10.1039 / C39840001702 .