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

Sodium 1,3-dithiole-2-thione-4,5-dithiolate
Names
	Preferred IUPAC name Disodium 2-sulfanylidene-2H-1,3-dithiole-4,5-bis(thiolate)
Identifiers
CAS Number	54995-24-3;
3D model (JSmol)	Interactive image;
ChemSpider	9405301;
PubChem CID	129790408;
	InChI 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;
	SMILES C1()SC(SC=1)=S..;
Properties
Chemical formula	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 , 100 kPa). Infobox references

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]

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 dmit^2-, reduction of CS₂ was thought to give tetrathiooxalate (Na₂C₂S₄).^[2]

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

₂ + 4 C₆H₅COCl → 2 C₃S₃(SC(O)C₆H₅)₂ + ₂

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

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

References

^ ^a ^b "4,5-Dibenzoyl-1,3-dithiole-1-thione". Org. Synth. 73: 270. 1996. doi:10.15227/orgsyn.073.0270.
^ Dietzsch, W.; Strauch, P.; Hoyer, E. (1992). "Thio-oxalates: Their Ligand Properties and Coordination Chemistry". Coord. Chem. Rev. 121: 43–130. doi:10.1016/0010-8545(92)80065-Y.
^ G. S. Girolami, T. B. Rauchfuss and R. J. Angelici (1999) Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA.ISBN 0-935702-48-2
^ W.T.A. Harrison; R.A. Howie; J.L. Wardell; S.M.S.V. Wardell; N.M. Comerlato; L.A.S. Costa; A.C. Silvino; A.I. de Oliveira; R.M. Silva (2000). "Crystal structures of three ²⁻ salts: ₂ (Q = 1,4-Me₂-pyridinium or NEt₄) and ₂·DMSO. Comparison of the dianion packing arrangements in ₂". Polyhedron. 19 (7): 821–827. doi:10.1016/S0277-5387(00)00322-3.
^ Niels Svenstrup; Jan Becher (1995). "The Organic Chemistry of 1,3-Dithiole-2-thione-4,5-dithiolate (DMIT)". Synthesis. 1995 (3): 215–235. doi:10.1055/s-1995-3910. S2CID 196762382.

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[OS-1] "4,5-Dibenzoyl-1,3-dithiole-1-thione". Org. Synth. 73: 270. 1996. doi:10.15227/orgsyn.073.0270.

[2] Dietzsch, W.; Strauch, P.; Hoyer, E. (1992). "Thio-oxalates: Their Ligand Properties and Coordination Chemistry". Coord. Chem. Rev. 121: 43–130. doi:10.1016/0010-8545(92)80065-Y.

[3] G. S. Girolami, T. B. Rauchfuss and R. J. Angelici (1999) Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA.ISBN 0-935702-48-2

[4] W.T.A. Harrison; R.A. Howie; J.L. Wardell; S.M.S.V. Wardell; N.M. Comerlato; L.A.S. Costa; A.C. Silvino; A.I. de Oliveira; R.M. Silva (2000). "Crystal structures of three ²⁻ salts: ₂ (Q = 1,4-Me₂-pyridinium or NEt₄) and ₂·DMSO. Comparison of the dianion packing arrangements in ₂". Polyhedron. 19 (7): 821–827. doi:10.1016/S0277-5387(00)00322-3.

[5] Niels Svenstrup; Jan Becher (1995). "The Organic Chemistry of 1,3-Dithiole-2-thione-4,5-dithiolate (DMIT)". Synthesis. 1995 (3): 215–235. doi:10.1055/s-1995-3910. S2CID 196762382.

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