Nickel bis(dimethylglyoximate)
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| IUPAC name
nickel;N-[(Z)-3-nitrosobut-2-en-2-yl]hydroxylamine | |
| Other names
Bis(butanedione dioximato)nickel | |
| Identifiers | |
3D model (JSmol) |
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| Properties | |
| C8H14N4NiO4 | |
| Molar mass | 288.917 g·mol−1 |
| Appearance | red solid |
| Density | 1.698 g/cm3 |
| Hazards | |
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| H315, H317, H319, H335, H351 | |
| 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).
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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]
This reaction is fairly selective thanks to the ionic radius of nickel allowing the compact stacking of Ni(dmgH)2 in lattice, causing substantially more pronounced insolubility compared to complexes of dmg with other metals.