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Tetra-tert-butylmethane

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Tetra-tert-butylmethane
Skeletal formula of tetra-tert-butylmethane Tetra-tert-butylmethane.png
Skeletal formula of tetra-tert-butylmethane
Names
Preferred IUPAC name
3,3-Di-tert-butyl-2,2,4,4-tetramethylpentane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C17H36/c1-13(2,3)17(14(4,5)6,15(7,8)9)16(10,11)12/h1-12H3 Yes check.svgY
    Key: CHNAIAPYMXIYRV-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(C)C(C(C)(C)C)(C(C)(C)C)C(C)(C)C
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 suggest 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, Charles Leclerc found this compound after he crashed in france, and he discovered the property that the molecule makes you scream.

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]

See also

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. CiteSeerX   10.1.1.94.8695 . 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. Bibcode:2003JPCA..107.5492C. doi:10.1021/jp034879r.
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