Hexaphenylethane 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. Th ...
consisting of an
ethane
Ethane ( , ) is an organic chemical compound with chemical formula . At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petro ...
core with six
phenyl
In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydroge ...
substituent
A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and '' functional group'', as well as '' ...
s. All attempts at its
synthesis
Synthesis or synthesize may refer to:
Science Chemistry and biochemistry
*Chemical synthesis, the execution of chemical reactions to form a more complex molecule from chemical precursors
**Organic synthesis, the chemical synthesis of organi ...
have been unsuccessful. The
trityl free radical, Ph
3C, was originally thought to
dimerize to form hexaphenylethane. However, an inspection of the
NMR spectrum of this dimer reveals that it is in fact a non-symmetrical species,
Gomberg's dimer
Gomberg's dimer is the organic compound with the formula Ph2C=C6H5-CPh3, where Ph = C6H5. It is a yellow solid that is air-stable for hours at room temperature and soluble in organic solvents. The compound achieved fame as the dimer of tripheny ...
instead.
A substituted derivative of hexaphenylethane, hexakis(3,5-di-''t''-butylphenyl)ethane, has however been prepared. It features a very long central C–C bond at 167 pm (compared to the typical bond length of 154 pm). Attractive
London dispersion force
London dispersion forces (LDF, also known as dispersion forces, London forces, instantaneous dipole–induced dipole forces, fluctuating induced dipole bonds or loosely as van der Waals forces) are a type of intermolecular force acting between at ...
s between the
''t''-butyl substituents are believed to be responsible for the stability of this very hindered molecule.
See also
*
Tetraphenylmethane
Tetraphenylmethane is an organic compound consisting of a methane core with four phenyl substituents. It was first synthesized by Moses Gomberg in 1898.
Synthesis
Gomberg's classical organic synthesis shown below starts by reacting tripheny ...
References
Literature
*
Hypothetical chemical compounds
Aromatic hydrocarbons
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