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Sodium maleonitriledithiolate

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Sodium maleonitriledithiolate
Names
Preferred IUPAC name
Disodium (Z)-1,2-dicyanoethene-1,2-bis(thiolate)
Other names
Sodium mnt sodium maleonitriledithiolate
Identifiers
3D model (JSmol)
ChemSpider
  • 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
  • [Na+].[Na+].[S-]/C(C#N)=C(/[S-])C#N
Properties
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).
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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−.[2]: 143–146 

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:[3]

8 NaCN + 8 CS2 → 4 Na2S2C2(CN)2 + S8

The compound was first described in 1958.[4]

References

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  1. ^ Chem Sources U.S.A. Directories Publishing Company, Incorporated. 2001. p. 535. ISBN 978-0-937020-34-0.
  2. ^ Day, Peter; Coronado, Eugenio (2004-12-14). Miller, Joel S.; Drillon, Marc (eds.). Molecular Materials Combining Magnetic and Conducting Properties (1 ed.). Wiley. pp. 105–159. doi:10.1002/3527604383.ch4. ISBN 978-3-527-30665-7.
  3. ^ Davison, A.; Holm, R. H.; Benson, R. E.; Mahler, W. (January 1967). Muetterties, Earl L. (ed.). Metal Complexes Derived from cis -1,2-dicyano-1,2-ethylenedithiolate and Bis(Trifluoromethyl)-1,2-dithiete. Vol. 10 (1 ed.). Wiley. pp. 8–26. doi:10.1002/9780470132418.ch3. ISBN 978-0-470-13169-5.
  4. ^ G. Bähr and G. Schleitzer (1957). "Beiträge zur Chemie des Schwefelkohlenstoffs und Selenkohlenstoffs, II. Die Kondensierende Spontan-Entschwefelung von Salzen und Estern der Cyan-Dithioameisensäure. Freie Cyan-Dithioameisensäure". Chemische Berichte. 90 (3): 438–443. doi:10.1002/cber.19570900322.