Tetra-tert-butylmethane

Tetra-*tert*-butylmethane
Names
	Preferred IUPAC name 3,3-Di-tert-butyl-2,2,4,4-tetramethylpentane
Identifiers
CAS Number	4103-17-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	14288112 ;
PubChem CID	14123361;
CompTox Dashboard (EPA)	DTXSID10556285 ;
	InChI InChI=1S/C17H36/c1-13(2,3)17(14(4,5)6,15(7,8)9)16(10,11)12/h1-12H3 Key: CHNAIAPYMXIYRV-UHFFFAOYSA-N ;
	SMILES CC(C)(C)C(C(C)(C)C)(C(C)(C)C)C(C)(C)C;
Properties
Chemical formula	C17H36
Molar mass	240.475 g·mol−1
Related compounds
Related alkanes	2,2-Dimethylbutane; 2,3-Dimethylbutane; Triptane; Tetramethylbutane; Tetraethylmethane; 2,2,4-Trimethylpentane; 2,3,3-Trimethylpentane; 2,3,4-Trimethylpentane; 2,3-Dimethylhexane; 2,5-Dimethylhexane;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Tetra-tert-butylmethane is a hypothetical organic compound with formula C₁₇H₃₆, consisting of four tert-butyl groups bonded to a central carbon atom. It would be an alkane, specifically the most compact branched isomer of heptadecane.

Some calculations suggests this compound cannot exist due to the steric hindrance among the closely packed tert-butyl groups, which would make it one of the smallest, if not the smallest itself, saturated and acyclic hydrocarbon that cannot exist.[1]

Other calculations suggest that the molecule would be stable, with the C–C bonds to the central ("methane") carbon having a length of 166.1 pm — longer than the typical C−C bond in order to reduce steric effects, but still shorter than those found in some other real molecules.[2]

References

da Silva, K.M.; Goodman, J.M. (2005). "What is the smallest saturated acyclic alkane that cannot be made?". Journal of Chemical Information and Modeling. 45 (1): 81–87. doi:10.1021/ci0497657. PMID 15667132.
Cheng, M-F; Li, W-K (2003). "Structural and energetics studies of tri- and tetra-tert-butylmethane". Journal of Physical Chemistry A. 78 (1): 5492–5498. doi:10.1021/jp034879r.

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[deSilva-1] Silva, K.M.; Goodman, J.M. (2005). "What is the smallest saturated acyclic alkane that cannot be made?". Journal of Chemical Information and Modeling. 45 (1): 81–87. doi:10.1021/ci0497657. PMID 15667132.

[Cheng-2] Cheng, M-F; Li, W-K (2003). "Structural and energetics studies of tri- and tetra-tert-butylmethane". Journal of Physical Chemistry A. 78 (1): 5492–5498. doi:10.1021/jp034879r.