Cyclohexanehexathione is a cyclic
covalent compound consisting of a six-
carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent
In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...
ring with a
sulfur
Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...
bonded to each. It has been generated by neutralization of its mono
anion
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...
() in a
mass spectrometer. This compound is the
thioketone analog of
cyclohexanehexone
Cyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is an organic compound with formula , the sixfold ketone of cyclohexane. It is an oxide of carbon (an oxocarbon), a hexamer of carbon monoxide.
The compound is expected to be ...
; that oxygen variant is expected to be substantially less stable.
Synthesis of by
photolysis
Photodissociation, photolysis, photodecomposition, or photofragmentation is a chemical reaction in which molecules of a chemical compound are broken down by photons. It is defined as the interaction of one or more photons with one target molecule. ...
or
pyrolysis
The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...
to extrude three equivalents of
carbon monoxide
Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...
from a precursor containing adjacent pairs of sulfurs as cyclic
dithiocarbonate Thiocarbonate describes a family of anions with the general chemical formula (''x'' = 0, 1, or 2):
*for ''x'' = 2 it is monothiocarbonate ion
*for ''x'' = 1 it is dithiocarbonate ion
*for ''x'' = 0 it is trithiocarbonate ion
Like the carbonate
...
units gave what is more likely a different
valence isomer In organic chemistry, two molecules are valence isomers when they are constitutional isomers that can interconvert through pericyclic reactions.
Benzene
There are many valence isomers one can draw for the C6H6 formula benzene. Some were originally ...
, as various
dithiete-containing structures are predicted to be more stable than the hexathione form.
:
This theoretical analysis of the various isomers and experimental analysis of this reaction cast doubt on whether the mass spectrometric approach really did produce the hexathione isomer as originally claimed. The increased stability of dithietes as compared to
dioxetane-like rings is one of theoretical bases for proposing is more stable than the oxygen analog.
References
{{chem-stub
Inorganic carbon compounds
Inorganic sulfur compounds
Thioketones