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Nickel bis(stilbenedithiolate)

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Nickel bis(stilbenedithiolate)
Names
Other names bisnickel
bis(dithiobenzil)nickel(II)
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.853 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • C1=CC=C(C=C1)/C(=C(/)\C2=CC=CC=C2)/.C1=CC=C(C=C1)/C(=C(/)\C2=CC=CC=C2)/.
Properties
Chemical formula C28H20NiS4
Molar mass 543.40 g·mol
Appearance black-green solid
Density 1.466 g/cm
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 nmα = 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 , 100 kPa). Infobox references
Chemical compound

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.

Limiting resonance structures of a R2C2S2M ring

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.

References

  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 = Ni, Pd, Pt) 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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