Nickel bis(stilbenedithiolate)

{{Chembox

| ImageFile1 = NIDPDS03.png

| ImageFile2 = Ni(S2C2Ph2)2.jpg

| ImageSize =

| ImageAlt =

| IUPACName =

| OtherNames =bis[1,2-diphenyl-1,2-ethenedithiolato]nickel
bis(dithiobenzil)nickel(II)

|Section1={{Chembox Identifiers

| CASNo = 28984-20-5

| PubChem = 5374634

| ChemSpiderID = 44211332

| DTXSID = DTXSID5067427

| StdInChI=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-;

| StdInChIKey = 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]

}}

|Section2={{Chembox Properties

| Ni=1|C=28|H=20|S=4

| MolarMass =

| Appearance = black-green solid

| Density = 1.466 g/cm³

| MeltingPtC = 260

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Structure

| Structure_ref ={{cite journal|doi=10.1039/J19670001264|title=The crystal structure of bis(dithiobenzil)nickel |year=1967 |last1=Sartain |first1=D. |last2=Truter |first2=Mary R. |journal=Journal of the Chemical Society A: Inorganic, Physical, Theoretical |page=1264 }}

| CrystalStruct = monoclinic

| SpaceGroup = P2₁/n

| Coordination =

| UnitCellFormulas =

| LattConst_a = 0.5836 nm

| LattConst_b = 1.097 nm

| LattConst_c = 1.836 nm

| LattConst_beta = 91.4

}}

|Section8={{Chembox Hazards

| ExternalSDS = [https://www.tcichemicals.com/JP/en/p/B1350 Bis(dithiobenzil)nickel(II)]. TCI

| MainHazards =

| FlashPt =

| AutoignitionPt =

| HPhrases = {{H-phrases|317|334|350|372}}

| PPhrases = {{P-phrases|260|270|272|280}}

}}

}}

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.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}} 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.{{cite journal|doi=10.1016/j.ica.2011.07.046|title=Syntheses and Characterization of Several Nickel Bis(dithiolene) Complexes with Strong and Broad Near-IR Absorption|journal=Inorganica Chimica Acta|volume=376|pages=619–627|year=2011|last1=Miao|first1=Qingqing|last2=Gao|first2=Junxiong|last3=Wang|first3=Zeqing|last4=Yu|first4=Hang|last5=Luo|first5=Yi|last6=Ma|first6=Tingli}}

:File:Resonance_structures_of_dithiolene_complex.png

The complex was prepared originally by treating nickel sulfide with diphenylacetylene.{{cite journal|doi=10.1021/ja00875a061|title=Reaction of Diphenylacetylene with Nickel Sulfides|journal=Journal of the American Chemical Society|volume=84|issue=16|pages=3221|year=1962|last1=Schrauzer|first1=G. N.|last2=Mayweg|first2=V.}} 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.{{cite journal|doi=10.1021/acs.inorgchem.7b00971|pmid = 28820242|title=Expanding the Scope of Ligand Substitution from [M(S2C2Ph2] (M = Ni²⁺, Pd²⁺, Pt²⁺) to Afford New Heteroleptic Dithiolene Complexes|journal=Inorganic Chemistry|volume=56|issue = 17|pages=10257–10267|year=2017|last1=Obanda|first1=Antony|last2=Martinez|first2=Kristina|last3=Schmehl|first3=Russell H.|last4=Mague|first4=Joel T.|last5=Rubtsov|first5=Igor V.|last6=MacMillan|first6=Samantha N.|last7=Lancaster|first7=Kyle M.|last8=Sproules|first8=Stephen|last9=Donahue|first9=James P.|url=http://eprints.gla.ac.uk/146400/1/146400.pdf}}