Sodium 1,3-dithiole-2-thione-4,5-dithiolate is the
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 ...
with the formula Na
2C
3S
5, abbreviated Na
2dmit. It is the sodium salt of the conjugate base of the 4,5-bis(sulfanyl)-
1,3-dithiole-2-thione. The salt is a precursor to
dithiolene complexes and
tetrathiafulvalene
Tetrathiafulvalene (TTF) is an organosulfur compound with the formula . It is the parent of many tetrathiafulvenes. Studies on these heterocyclic compound contributed to the development of molecular electronics, although no practical applications ...
s.
Reduction of
carbon disulfide
Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula and structure . It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used as ...
with sodium affords sodium 1,3-dithiole-2-thione-4,5-dithiolate together with sodium
trithiocarbonate 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 d ...
:
:4 Na + 4 CS
2 → Na
2C
3S
5 + Na
2CS
3
Before the characterization of dmit
2-, reduction of CS
2 was thought to give tetrathiooxalate (Na
2C
2S
4).
The dianion C
3S
52- is purified as the
tetraethylammonium
Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula , consisting of four ethyl groups (, denoted Et) attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salt ...
salt of the zincate complex
3S5)2">n(C3S5)2sup>2-. This salt converts to the bis(thioester) upon treatment with
benzoyl chloride
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula . It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring () with an acyl chloride () substituent. It is ...
:
[
: 2H5)4">(C2H5)4sub>2 3S5)2">n(C3S5)2+ 4 C6H5COCl → 2 C3S3(SC(O)C6H5)2 + 2H5)4">(C2H5)4sub>2 4">nCl4Cleavage of the thioester with ]sodium methoxide
Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed by the deprotonation of methanol. It is a widely used reagent in industry and the laboratory. It is also a dangerously caustic base.
...
gives sodium 1,3-dithiole-2-thione-4,5-dithiolate:
:C3S3(SC(O)C6H5)2 + 2 NaOCH3 → Na2C3S5 + 2 C6H5CO2Me
Na2dmit undergoes S-alkylation.[{{cite journal, author=Niels Svenstrup , author2=Jan Becher , title=The Organic Chemistry of 1,3-Dithiole-2-thione-4,5-dithiolate (DMIT), journal=Synthesis, year=1995, volume=1995, issue=3, pages=215–235, doi=10.1055/s-1995-3910, s2cid=196762382] Heating solutions of Na2dmit gives the isomeric 1,2-dithioledithiolate.
References
Thiolates
Alkene derivatives
Sodium compounds