Tetra-''tert''-butylmethane is a hypothetical

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with formula C₁₇H₃₆, consisting of four ''tert''-butyl groups bonded to a central carbon atom. It would be an

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...

, specifically the most compact branched

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

heptadecane Heptadecane is an organic compound, an alkane hydrocarbon with the chemical formula C17H36. The name may refer to any of 24894 theoretically possible structural isomers, or to a mixture thereof. The unbranched isomer is normal or ''n''-heptadecane ...

. Some calculations suggests this compound cannot exist due to the

steric hindrance Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivity of ions ...

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. Other calculations suggest that the molecule would be stable, with the C–C bonds to the central ("methane") carbon having a

length Length is a measure of distance. In the International System of Quantities, length is a quantity with dimension distance. In most systems of measurement a base unit for length is chosen, from which all other units are derived. In the Interna ...

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.

References

Alkanes Hypothetical chemical compounds Tert-butyl compounds {{theoretical-chem-stub