Tetra-tert-butylmethane

Tetra-*tert*-butylmethane
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). verify (what is ?) Infobox references

Tetra-tert-butylmethane is a hypothetical organic compound with formula C₁₇H₃₆, or ((H₃C)₃C)₄C. It would be an alkane, specifically the most compact branched isomer of heptadecane. The systematic name is 3,3-di-tert-butyl-2,2,4,4-tetramethylpentane.

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] However others suggest that the molecule would be stable, with C–C bonds of 0.1661 nm — longer than the typical C−C bond 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 and Information 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.

[deSilva-1] Silva, K.M.; Goodman, J.M. (2005). "What is the smallest saturated acyclic alkane that cannot be made?". Journal of Chemical and Information 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.

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