Nickel bis(stilbenedithiolate)

Nickel bis(stilbenedithiolate)
Names
Other names
bis[1,2-diphenyl-1,2-ethenedithiolato]nickel
bis(dithiobenzil)nickel(II)
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.853
  • InChI=1S/2C14H12S2.Ni/c2*15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12;/h2*1-10,15-16H;/p-4/b2*14-13-;
    Key: LJISAPFYPQSNRX-DEWSNNOYSA-J
  • C1=CC=C(C=C1)/C(=C(/[S-])\C2=CC=CC=C2)/[S-].C1=CC=C(C=C1)/C(=C(/[S-])\C2=CC=CC=C2)/[S-].[Ni]
Properties
C28H20NiS4
Molar mass 543.40 g·mol−1
Appearance black-green solid
Density 1.466 g/cm3
Melting point 260 °C (500 °F; 533 K)
Structure
monoclinic
P21/n
a = 0.5836 nm, b = 1.097 nm, c = 1.836 nm
α = 90°, β = 91.4°, γ = 90°
Hazards
GHS labelling:
H317, H334, H350, H372
P260, P270, P272, P280
Safety data sheet (SDS) Bis(dithiobenzil)nickel(II). TCI
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Nickel bis(stilbenedithiolate) or bis(dithiobenzil)nickel is a coordination complex with the formula Ni(S2C2Ph2)2 (where Ph = phenyl). It exists as a black solid that gives green solutions in toluene due to a strong absorption at 855 nm. The complex is a prototype of a large family of bis(dithiolene) complexes or the formula Ni(S2C2R2)2 (R = H, alkyl, aryl). These complexes have attracted much attention as dyes. They are of academic interest because the dithiolenes are noninnocent ligands. The lengths of the C-S and C-C bonds in the backbone, respectively 1.71 and 1.39 Å, are intermediate between double and single bonds.

The complex was prepared originally by treating nickel sulfide with diphenylacetylene. High yielding syntheses involve treating nickel salts with sulfided benzoin. The complex reacts with ligands to form monodithiolene complexes of the type Ni(S2C2Ph2)L2.

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