Tetralithiomethane, also known as tetralithium carbide, is an organolithium compound with the formula CLi4. It is an extremely pyrophoric red solid and is the lithium analog of methane.[2]
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| Names | |
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| IUPAC name
Tetralithiomethane
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Other names
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| Identifiers | |
3D model (JSmol)
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| Properties | |
| CLi4 | |
| Molar mass | 39.77 g·mol−1 |
| Appearance | Red solid |
| Melting point | 225 °C (437 °F; 498 K)[1] (decomposes) |
| Hydrolysis | |
| Solubility | Soluble in cyclohexane |
| Hazards | |
| GHS labelling: | |
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| Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production
editIts main route of production is by the lithiation of tetrakis(chloromercurio)methane (C(HgCl)4) by tert-butyllithium. It can also be produced by the reaction of lithium metal and carbon tetrachloride at 900 °C:[2][3]
- 8 Li + CCl4 → CLi4 + 4 LiCl
However, this method also produces byproducts, such as lithium carbide.
Reactions
editTetralithiomethane hydrolyzes vigorously in contact with water producing methane gas and lithium hydroxide:[2]
- CLi4 + 4 H2O → CH4 + 4 LiOH
Deuterated methane CD4 can also be produced by reacting heavy water with tetralithiomethane.
- CLi4 + 4 D2O → CD4 + 4 LiOD
When tetralithiomethane is heated to 225 °C, it decomposes to lithium carbide and lithium metal.[1][2]
Due to the known affinity of lithium ions Li+ for hydrogen molecules H2 and therefore potential applications in hydrogen storage materials, tetralithiomethane has been studied computationally for its aggregation, H2 affinity, and binding to various graphene-type surfaces.[4]
References
edit- ^ a b Lawrence A. Shimp; John A. Morrison; John A. Gurak; John W. Chinn Jr.; Richard J. Lagow (1981). "Observations on the nature of polylithium organic compounds and their rearrangements". Journal of the American Chemical Society. 103 (19): 5951–5953. doi:10.1021/ja00409a074.
- ^ a b c d Adalbert Maercker; Manfred Theis (1984). "Tetralithiomethane". Angewandte Chemie International Edition. 23 (12): 995–996. doi:10.1002/anie.198409951.
- ^ C. Chung; R. J. Lagow (1972). "Reaction of lithium atoms at 800 °C with chlorocarbons; a new route to polylithium compounds". Journal of the Chemical Society, Chemical Communications (19): 1078–1079. doi:10.1039/C3972001078B.
- ^ Er, Süleyman; de Wijs, Gilles A.; Brocks, Geert (2009). "Hydrogen Storage by Polylithiated Molecules and Nanostructures". J. Phys. Chem. C. 113 (20): 8997–9002. arXiv:0902.2339. doi:10.1021/jp901305h. S2CID 17237753.