Sodium 1,3-dithiole-2-thione-4,5-dithiolate

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Sodium 1,3-dithiole-2-thione-4,5-dithiolate

Sodium 1,3-dithiole-2-thione-4,5-dithiolate is the organosulfur compound with the formula Na2C3S5, abbreviated Na2dmit. 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 tetrathiafulvalenes.[1]

Quick Facts Names, Identifiers ...
Sodium 1,3-dithiole-2-thione-4,5-dithiolate
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Names
Preferred IUPAC name
Disodium 2-sulfanylidene-2H-1,3-dithiole-4,5-bis(thiolate)
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C3H2S5.2Na/c4-1-2(5)7-8-3(1)6;;/h4-5H;;/q;2*+1/p-2
    Key: JTYXTCNFMIILHG-UHFFFAOYSA-L
  • InChI=1S/C3H2S5.2Na/c4-1-2(5)8-3(6)7-1;;/h4-5H;;/q;2*+1/p-2
  • C1([S-])SC(SC=1[S-])=S.[Na+].[Na+]
Properties
C3Na2S5
Molar mass 242.31 g·mol−1
Appearance yellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reduction of carbon disulfide with sodium affords sodium 1,3-dithiole-2-thione-4,5-dithiolate together with sodium trithiocarbonate:

4 Na + 4 CS2 → Na2C3S5 + Na2CS3

Before the characterization of dmit2-, reduction of CS2 was thought to give tetrathiooxalate (Na2C2S4).[2]

The dianion C3S52- is purified as the tetraethylammonium salt of the zincate complex [Zn(C3S5)2]2-. This salt converts to the bis(thioester) upon treatment with benzoyl chloride:[3][1]

[N(C2H5)4]2[Zn(C3S5)2] + 4 C6H5COCl → 2 C3S3(SC(O)C6H5)2 + [N(C2H5)4]2[ZnCl4]

Cleavage of the thioester with sodium methoxide gives sodium 1,3-dithiole-2-thione-4,5-dithiolate:

C3S3(SC(O)C6H5)2 + 2 NaOCH3 → Na2C3S5 + 2 C6H5CO2Me
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Structure of [Zn(dmit)2]2-.[4]

Na2dmit undergoes S-alkylation.[5] Heating solutions of Na2dmit gives the isomeric 1,2-dithioledithiolate.

References

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