Sodium maleonitriledithiolate

Sodium maleonitriledithiolate

File:Sodium maleonitriledithiolate.svg
Names
Preferred IUPAC name Disodium (Z)-1,2-dicyanoethene-1,2-bis(thiolate)
Other names Sodium mnt sodium maleonitriledithiolate
Identifiers
CAS Number	5466-54-6 checkY
3D model (JSmol)	Interactive image
ChemSpider	5013443 checkY
ECHA InfoCard
E number
PubChem CID	6523934
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C4H2N2S2.2Na/c5-1-3(7)4(8)2-6;;/h7-8H;;/q;2*+1/p-2/b4-3+;; checkY Key: UIEQIOFOWZBELJ-CZEFNJPISA-L checkY InChI=1/C4H2N2S2.2Na/c5-1-3(7)4(8)2-6;;/h7-8H;;/q;2*+1/p-2/b4-3+;; Key: UIEQIOFOWZBELJ-YWCBZGCUBZ
SMILES [Na+].[Na+].[S-]/C(C#N)=C(/[S-])C#N
Properties
Chemical formula	C4N2Na2S2
Molar mass	186.16 g·mol−1
Appearance	yellow solid
Solubility in ethanol, DMF	Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). checkY verify (what is checkY☒N ?) Infobox references

Sodium maleonitriledithiolate is the chemical compound described by the formula Na₂S₂C₂(CN)₂. The name refers to the cis compound, structurally related to maleonitrile ((CH(CN))₂). Maleonitriledithiolate is often abbreviated mnt. It is a "dithiolene", i.e. a chelating alkene-1,2-dithiolate. It is a prototypical non-innocent ligand in coordination chemistry. Several complexes are known, such as Ni(mnt)₂]²⁻.

File:(Et4N)2Ni(mnt)2.jpg

Sample of ([(CH₃CH₂)₄N]⁺)₂[Ni(mnt)₂]²⁻.

The salt is synthesized by treating carbon disulfide with sodium cyanide to give the cyanodithioformate salt, which eliminates elemental sulfur in aqueous solution:

8 NaCN + 8 CS₂ → 4 Na₂S₂C₂(CN)₂ + S₈

The compound was first described in 1958.