Phenyl(trichloromethyl)mercury is an
organomercury compound with the formula
C6H5HgCCl
3. It is a white solid that is soluble in
organic solvent
A solvent (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...
s. The compound is used as a source of
dichlorocarbene
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapi ...
, e.g. in
cyclopropanation
In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane () Ring (chemistry), rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insectic ...
reactions, because the products are particularly easy to extract from the reaction mixture. Strong nucleophiles may catalyze the reaction by displacing CCl from mercury, although the free ion is not believed to form in the process. Unusually, the pure organomercury compound reacts with electron-poor alkenes, converting tetrachloroethylene to hexachlorocyclopropane:
:C
6H
5HgCCl
3 → C
6H
5HgCl + CCl
2
:CCl
2 + Cl
2C=CCl
2 → C
3Cl
6
The compound is prepared by treating with sources of dichlorocarbene. These include the base/
haloform reaction and thermolysis of
sodium trichloroacetate:
:NaO
2CCCl
3 + C
6H
5HgCl → C
6H
5HgCCl
3 + NaCl + CO
2
Related compounds
Closely related compounds include phenyl(bromodichloromethyl)mercury (CAS
registry number 3294-58-4) and phenyl(tribromomethyl)mercury (CAS registry number 3294-60-8). According to
X-ray crystallography
X-ray crystallography is the experimental science of determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to Diffraction, diffract in specific directions. By measuring th ...
, the former has nearly linear coordination geometry at mercury, with a C-Hg-C angle of 179° and Hg-C distances of 2.047 Å.
Also known is bis(trichloromethyl)mercury, Hg(CCl
3)
2.
References
{{Mercury compounds
Organomercury compounds
Phenyl compounds
Trichloromethyl compounds