Nickel bis(dimethylglyoximate)
{{Chembox
| ImageFile1 = NIMGLO12.png
| ImageSize1 = 180
| ImageFile2 = Ni(dmg)2.JPG
| ImageSize2 = 200
| ImageAlt =
| IUPACName = nickel;N-[(Z)-3-nitrosobut-2-en-2-yl]hydroxylamine
| OtherNames = Bis(butanedione dioximato)nickel
|Section1={{Chembox Identifiers
| CASNo = 13478-93-8
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7CZ5340YUM
| PubChem = 5475696
| ChemSpiderID = 4584372
| EC_number = 236-782-7| StdInChI=1S/2C4H8N2O2.Ni/c2*1-3(5-7)4(2)6-8;/h2*5,7H,1-2H3;/b2*4-3-;
| StdInChIKey = CNOULSXJEKYGTK-FDGPNNRMSA-N
| SMILES = CC(=C(C)N=O)NO.CC(=C(C)N=O)NO.[Ni]
}}
|Section2={{Chembox Properties
| C=8|H=14|N=4|O=4|Ni=1
| MolarMass =
| Appearance = red solid
| Density = 1.698 g/cm3
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS08}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|317|319|335|351}}
| PPhrases = {{P-phrases|201|202|261|264|271|272|280|281|302+352|304+340|305+351+338|308+313|312|321|332+313|333+313|337+313|362|363|403+233|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
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Nickel bis(dimethylglyoximate) is the coordination complex with the formula Ni[ONC(CH3)C(CH3)NOH]2. The compound is a bright red solid. It achieved prominence for its use in the qualitative analysis of nickel.{{Greenwood&Earnshaw2nd}}
Structure
The geometry of the nickel(II) ion is square planar.{{cite journal|title=Crystal Structures of Nickel and Palladium Dimethylglyoximes
|author=Donald E. Williams |author2=Gabriele Wohlauer |author3=R. E. Rundle
|journal=J. Am. Chem. Soc.
|year=1959
|volume=81
|issue=3
|pages=755–756
|doi=10.1021/ja01512a066}} It is surrounded by two equivalents of the conjugate base (dmgH−) of dimethylglyoxime (dmgH2). The pair of organic ligands are joined through hydrogen bonds to give a macrocyclic ligand. The complex is distinctively colored and insoluble leading to its use as a chelating agent in the gravimetric analysis of nickel.
The use of dimethylglyoxime as a reagent to detect nickel was reported by L. A. Chugaev in 1905.{{cite journal
| title = Über ein neues, empfindliches Reagens auf Nickel|first=Lev
| last = Tschugaeff
| journal = Berichte der Deutschen Chemischen Gesellschaft
| volume = 38
| issue = 3
| pages = 2520–2522
| year = 1905|language=de|trans-title=About a new, sensitive reagent on nickel
| url = https://zenodo.org/record/1426158
| doi = 10.1002/cber.19050380317 }}
