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 chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...
that contains two adjacent sulfur atoms and two sp
2-hybridized carbon centers.
Derivatives
The derivative of a function is the rate of change of the function's output relative to its input value.
Derivative may also refer to:
In mathematics and economics
* Brzozowski derivative in the theory of formal languages
* Formal derivative, an ...
are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of
aromatic
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...
organosulfur compound
Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfu ...
s. A few 1,2-dithietes have been isolated.
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 which have absorbed ultraviolet photons, in order to determine molecular orbital energies in the valence region ...
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 function ...
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 photons. It is defined as the interaction of one or more photons with one target molecule. ...
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
*
Dithietane
Dithietanes are saturated heterocyclic compounds that contain two divalent sulfur atoms and two sp3-hybridized carbon centers. Two isomers are possible for this class of organosulfur compounds:
1,2-Dithietanes
1,2-dithietanes, 4-membered rings ...
- the corresponding saturated ring
*
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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Organosulfur compounds
Organic disulfides
Sulfur heterocycles
Four-membered rings