Hexamethylbenzene
Encyclopedia
Hexamethylbenzene is white crystalline solid with chemical formula C6(CH3)6. It is a synthetic aromatic hydrocarbon
with six methyl groups stemming from the carbon centres of the ring. Hexamethylbenzene has historical significance in the field of X-ray crystallography
. In 1929, Kathleen Lonsdale
first proved the shape of hexamethylbenzene and thus showed that the benzene ring, and by implication its six hydrogen centres, is hexagonal and flat.
. Two examples from organoruthenium chemistry
are the sandwich complexes Ru(ɳ4-C6(CH3)6)(ɳ6-C6(CH3)6) and the dication [Ru(ɳ6-C6(CH3)6)2]2+.
Aromatic hydrocarbon
An aromatic hydrocarbon or arene is a hydrocarbon with alternating double and single bonds between carbon atoms. The term 'aromatic' was assigned before the physical mechanism determining aromaticity was discovered, and was derived from the fact that many of the compounds have a sweet scent...
with six methyl groups stemming from the carbon centres of the ring. Hexamethylbenzene has historical significance in the field of X-ray crystallography
X-ray crystallography
X-ray crystallography is a method of determining the arrangement of atoms within a crystal, in which a beam of X-rays strikes a crystal and causes the beam of light to spread into many specific directions. From the angles and intensities of these diffracted beams, a crystallographer can produce a...
. In 1929, Kathleen Lonsdale
Kathleen Lonsdale
Dame Kathleen Lonsdale, DBE FRS was a crystallographer, who established the structure of benzene by X-ray diffraction methods in 1929, and hexachlorobenzene by Fourier spectral methods in 1931...
first proved the shape of hexamethylbenzene and thus showed that the benzene ring, and by implication its six hydrogen centres, is hexagonal and flat.
Uses
Hexamethylbenzene has no significant commercial uses. The six methyl groups enhance the proton affinity of the central ring. Because it is electron-rich, hexamethylbenzene can be used as a ligand in organometallic chemistryOrganometallic chemistry
Organometallic chemistry is the study of chemical compounds containing bonds between carbon and a metal. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character...
. Two examples from organoruthenium chemistry
Organoruthenium chemistry
Organoruthenium chemistry is the chemistry of organometallic compounds containing a carbon to ruthenium chemical bond. The interest is mostly academic although several organoruthenium catalysts are of commercial interest. The chemistry has many similarities with organoiron chemistry, as iron is...
are the sandwich complexes Ru(ɳ4-C6(CH3)6)(ɳ6-C6(CH3)6) and the dication [Ru(ɳ6-C6(CH3)6)2]2+.