Nickel bis(dimethylglyoximate)

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.^[1]

Nickel bis(dimethylglyoximate)

Names
IUPAC name nickel;N-[(Z)-3-nitrosobut-2-en-2-yl]hydroxylamine
Other names Bis(butanedione dioximato)nickel
Identifiers
CAS Number	13478-93-8 Y
3D model (JSmol)	Interactive image
ChemSpider	4584372
EC Number	236-782-7
PubChem CID	5475696
UNII	7CZ5340YUM Y
InChI InChI=1S/2C4H8N2O2.Ni/c2*1-3(5-7)4(2)6-8;/h2*5,7H,1-2H3;/b2*4-3-; Key: CNOULSXJEKYGTK-FDGPNNRMSA-N
SMILES CC(=C(C)N=O)NO.CC(=C(C)N=O)NO.[Ni]
Properties
Chemical formula	C8H14N4NiO4
Molar mass	288.917 g·mol−1
Appearance	red solid
Density	1.698 g/cm3
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H335, H351
Precautionary statements	P201, P202, P261, P264, P271, P272, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Structure

The geometry of the nickel(II) ion is square planar.^[2] 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.^[3]