Tetraethynylmethane is an organic compound with formula C9H4, consisting of four ethynyl groups bonded to a central carbon atom. It is an alkyne, and one of the most compact possible hydrocarbons. It has been synthesised for potential applications in the synthesis of polymeric forms of carbon such as synthetic diamond and fullerenes.[1][2][3][4][5][6]
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| Names | |
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| Preferred IUPAC name
3,3-diethynylpenta-1,4-diyne | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C9H4 | |
| Molar mass | 112.131 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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See also
edit- Neopentane
- Tetraethylmethane
- Tetravinylmethane
- Tetra-tert-butylmethane
- Tetracyclopropylmethane
- Tetraphenylmethane
- Tetrakis(trimethylsilyl)methane
- Methanetetracarboxylate
- Tetramethoxymethane
- Tetrafluoromethane
- Tetrachloromethane
- Tetrabromomethane
- Tetraiodomethane
- Tetraazidomethane
- Tetracyanomethane
- Tetranitromethane
References
edit- ^ Feldman KS, Kraebel CM, Parvez M (May 1993). "Tetraethynylmethane". Journal of the American Chemical Society. 115 (9): 3846–3847. doi:10.1021/ja00062a089.
- ^ Feldman KS, Weinreb CK, Youngs WJ, Bradshaw JD (October 1994). "Preparation and some subsequent transformations of tetraethynylmethane". Journal of the American Chemical Society. 116 (20): 9019–9026. doi:10.1021/ja00099a020.
- ^ Feldman KS, Mareska DA, Weinreb CK, Chasmawala M (January 1996). "Preliminary studies towards crosslinking polymerizations with tetraethynylmethane and its derivatives: evidence for unusually facile alkyne hydration". Chemical Communications (7): 865–866. doi:10.1039/CC9960000865.
- ^ Amemiya R, et al. One-Step Synthesis of Triethynylvinylmethanes and Tetraethynylmethanes by GaCl 3 -Promoted Diethynylation of 1,4-Enynes and 1,4-Diynes. Journal of the American Chemical Society 2005; 127(23):8252-3. doi:10.1021/ja051416l
- ^ Zhao Z, et al. A 3D Organically Synthesized Porous Carbon Material for Lithium-Ion Batteries. Angewandte Chemie 2018; 57(37): 11952-11956. doi:10.1002/anie.201805924
- ^ Kilde MD, Murray AH, Andersen CL, et al. Synthesis of radiaannulene oligomers to model the elusive carbon allotrope 6,6,12-graphyne. Nat Commun 2019;10:3714. doi:10.1038/s41467-019-11700-0
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