Dithiete is an unsaturated
heterocyclic compound
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...
that contains two adjacent sulfur atoms and two sp
2-hybridized carbon centers.
Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of
aromatic
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
organosulfur compound
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
s. A few 1,2-dithietes have been isolated; one (low-yielding) route is oxidation of a
dithiolene complex.
is a particularly stable example.
Unsubstituted 1,2-dithiete has been generated in thermolytic reactions and was characterized by
microwave spectroscopy
Microwave spectroscopy is the spectroscopy method that employs microwaves, i.e. electromagnetic radiation at GHz frequencies, for the study of matter.
History
The ammonia molecule NH3 is shaped like a pyramid 0.38 Å in height, with an equilatera ...
,
ultraviolet photoelectron spectroscopy
Ultraviolet photoelectron spectroscopy (UPS) refers to the measurement of kinetic energy spectra of photoelectrons emitted by molecules that have absorbed ultraviolet photons, in order to determine molecular orbital energies in the valence regio ...
and
infrared spectroscopy
Infrared spectroscopy (IR spectroscopy or vibrational spectroscopy) is the measurement of the interaction of infrared radiation with matter by absorption, emission, or reflection. It is used to study and identify chemical substances or functio ...
in a low temperature matrix. The open ring isomer, dithioglyoxal, HC(S)C(S)H, is less stable than the 1,2-dithiete.
The dithione can be prepared (as ''trans''-dithioglyoxal) by low temperature
photolysis
Photodissociation, photolysis, photodecomposition, or photofragmentation is a chemical reaction in which molecules of a chemical compound are broken down by absorption of light or photons. It is defined as the interaction of one or more photons wi ...
of 1,3-dithiol-2-one. Quantum chemical calculations reproduce the observed greater stability of 1,2-dithiete only if large basis-sets with
polarization functions are used.
:
See also
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Dithietane
A dithietane is a saturated heterocyclic compound that contain two Valence (chemistry), divalent sulfur atoms and two Orbital hybridisation, sp3-hybridized carbon atoms. Two isomers are possible for this class of organosulfur compounds:
1,2-Dith ...
- the corresponding saturated ring
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Thiete
Thiete is a heterocyclic compound containing an unsaturated four-membered ring with three carbon atoms and one sulfur atom. It is more commonly encountered not on its own, but in anellated derivatives, several of which have been synthesized. Thi ...
- an analogue with only one sulfur atom
Additional reading
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References
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Organic disulfides
Sulfur heterocycles
Four-membered rings