Nickel bis(stilbenedithiolate)

Nickel bis(stilbenedithiolate)
Names
	Other names bis[1,2-diphenyl-1,2-ethenedithiolato]nickel; bis(dithiobenzil)nickel(II)
Identifiers
CAS Number	28984-20-5;
3D model (JSmol)	Interactive image;
ChemSpider	44211332;
ECHA InfoCard	100.044.853
PubChem CID	5374634;
CompTox Dashboard (EPA)	DTXSID5067427;
	InChI InChI=1S/2C14H12S2.Ni/c215-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12;/h21-10,15-16H;/p-4/b2*14-13-; Key: LJISAPFYPQSNRX-DEWSNNOYSA-J;
	SMILES 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
Chemical formula	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
Crystal structure	monoclinic
Space group	P21/n
Lattice constant	a = 0.5836 nm, b = 1.097 nm, c = 1.836 nm α = 90°, β = 91.4°, γ = 90°
Hazards
	GHS labelling:
Hazard statements	H317, H334, H350, H372
Precautionary statements	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.^[2] 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.^[3]

The complex was prepared originally by treating nickel sulfide with diphenylacetylene.^[4] 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.^[5]

References

^ Sartain, D.; Truter, Mary R. (1967). "The crystal structure of bis(dithiobenzil)nickel". Journal of the Chemical Society A: Inorganic, Physical, Theoretical: 1264. doi:10.1039/J19670001264.
^ Karlin, K. D.; Stiefel, E. I., Eds. “Progress in Inorganic Chemistry, Dithiolene Chemistry: Synthesis, Properties, and Applications” Wiley-Interscience: New York, 2003. ISBN 0-471-37829-1
^ Miao, Qingqing; Gao, Junxiong; Wang, Zeqing; Yu, Hang; Luo, Yi; Ma, Tingli (2011). "Syntheses and Characterization of Several Nickel Bis(dithiolene) Complexes with Strong and Broad Near-IR Absorption". Inorganica Chimica Acta. 376: 619–627. doi:10.1016/j.ica.2011.07.046.
^ Schrauzer, G. N.; Mayweg, V. (1962). "Reaction of Diphenylacetylene with Nickel Sulfides". Journal of the American Chemical Society. 84 (16): 3221. doi:10.1021/ja00875a061.
^ Obanda, Antony; Martinez, Kristina; Schmehl, Russell H.; Mague, Joel T.; Rubtsov, Igor V.; MacMillan, Samantha N.; Lancaster, Kyle M.; Sproules, Stephen; Donahue, James P. (2017). "Expanding the Scope of Ligand Substitution from [M(S2C2Ph2] (M = Ni²⁺, Pd²⁺, Pt²⁺) to Afford New Heteroleptic Dithiolene Complexes" (PDF). Inorganic Chemistry. 56 (17): 10257–10267. doi:10.1021/acs.inorgchem.7b00971. PMID 28820242.

[1] Sartain, D.; Truter, Mary R. (1967). "The crystal structure of bis(dithiobenzil)nickel". Journal of the Chemical Society A: Inorganic, Physical, Theoretical: 1264. doi:10.1039/J19670001264.

[2] Karlin, K. D.; Stiefel, E. I., Eds. “Progress in Inorganic Chemistry, Dithiolene Chemistry: Synthesis, Properties, and Applications” Wiley-Interscience: New York, 2003. ISBN 0-471-37829-1

[3] Miao, Qingqing; Gao, Junxiong; Wang, Zeqing; Yu, Hang; Luo, Yi; Ma, Tingli (2011). "Syntheses and Characterization of Several Nickel Bis(dithiolene) Complexes with Strong and Broad Near-IR Absorption". Inorganica Chimica Acta. 376: 619–627. doi:10.1016/j.ica.2011.07.046.

[4] Schrauzer, G. N.; Mayweg, V. (1962). "Reaction of Diphenylacetylene with Nickel Sulfides". Journal of the American Chemical Society. 84 (16): 3221. doi:10.1021/ja00875a061.

[5] Obanda, Antony; Martinez, Kristina; Schmehl, Russell H.; Mague, Joel T.; Rubtsov, Igor V.; MacMillan, Samantha N.; Lancaster, Kyle M.; Sproules, Stephen; Donahue, James P. (2017). "Expanding the Scope of Ligand Substitution from [M(S2C2Ph2] (M = Ni²⁺, Pd²⁺, Pt²⁺) to Afford New Heteroleptic Dithiolene Complexes" (PDF). Inorganic Chemistry. 56 (17): 10257–10267. doi:10.1021/acs.inorgchem.7b00971. PMID 28820242.

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