Tetra-tert-butylmethane

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.

Tetra-tert-butylmethane
Names
Preferred IUPAC name
3,3-Di-tert-butyl-2,2,4,4-tetramethylpentane
Identifiers
3D model (JSmol)
ChemSpider
Properties
C17H36
Molar mass 240.475 g·mol−1
Related compounds
Related alkanes
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

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

  1. 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.
  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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