Ni Dmg 2

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Dimethylglyoxime
Names
IUPAC name
Other names
  • Dimethylglyoxime
  • Diacetyl dioxime
  • Butane-2,3-dioxime
  • Chugaev's reagent
Identifiers
  • 95-45-4
ChEMBL
ChemSpider
  • 10606175
ECHA InfoCard100.002.201
EC Number
PubChemCID
RTECS number
  • EK2975000
UNII
  • InChI=1S/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+
  • InChI=1/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+
  • CC(=NO)C(C)=NO
Properties
C4H8N2O2
Molar mass116.120 g·mol−1
AppearanceWhite/Off White Powder
Density1.37 g/cm3
Melting point 240 to 241 °C (464 to 466 °F; 513 to 514 K)
Boiling pointdecomposes
low
Structure
0
Hazards
Main hazardsToxic, Skin/Eye Irritant
Safety data sheetExternal MSDS
GHS pictograms
GHS Signal wordDanger
H228, H301
P210, P240, P241, P264, P270, P280, P301+310, P321, P330, P370+378, P405, P501
NFPA 704 (fire diamond)
Related compounds
Hydroxylamine
salicylaldoxime
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The ground state electronic configuration of Ni is Ar 3d8 4s2. So if you fill up the energy levels you will get two unpaired electrons in ground state.

Dimethylglyoxime is a chemical compound described by the formula CH3C(NOH)C(NOH)CH3. Its abbreviation is dmgH2 for neutral form, and dmgH for anionic form, where H stands for hydrogen. This colourless solid is the dioxime derivative of the diketone butane-2,3-dione (also known as diacetyl). DmgH2 is used in the analysis of palladium or nickel. Its coordination complexes are of theoretical interest as models for enzymes and as catalysts. Many related ligands can be prepared from other diketones, e.g. benzil.

Balance the reaction of Ni(NO3)2 + DMG = Ni(DMG)2 + NO3 using this chemical equation balancer! Balance the reaction of Ni(NO3)2 + DMG = Ni(DMG)2 + NO3 using this chemical equation balancer!

  • The hybridization of Ni in Ni(DMG)2 is dsp2. Ni forms octahedral, square planar and tetrahedral complexes in +2 oxidation state. It acquires stability through chelation and intramolecular hydrogen bonding. In Ni(DMG)2 the nickel is in the +2 oxidation state and to have a square planar geometry because of chelation the pairing of electrons takes place.
  • Pour half the nickel ethylene diamine solution into a small hydrometer and add the DMG solution dropwise to form the red precipitate. Hint: Any green precipitate formation is due to Ni(OH)2 precipitate. (Add more ammonia to make it go away.).
  • Examples of molecular weight computations: C14O162, S34O162. Definitions of molecular mass, molecular weight, molar mass and molar weight. Molecular mass (molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12).

Preparation[edit]

Dimethylglyoxime can be prepared from butanone first by reaction with ethyl nitrite to give biacetyl monoxime. The second oxime is installed using sodium hydroxylamine monosulfonate:[1]

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Complexes[edit]

Dimethylglyoxime is used to detect and quantify nickel, which forms the bright red complex nickel bis(dimethylglyoximate) (Ni(dmgH)2). The reaction was discovered by L. A. Chugaev in 1905.[2]

Cobalt complexes have also received much attention. In chloro(pyridine)cobaloxime[3] the macrocycle [dmgH]22− mimics the macrocyclic ligand found in vitamin B12.

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Structure of chloro(pyridine)cobaloxime.

Structure Of Ni(dmg)2 Complex

References[edit]

Ni Nh3 6

Ni(dmg)2 preparation

Ni(dmg)2 Geometry

  1. ^Semon, W. L.; Damerell, V. R. (1930). 'Dimethylglyoxime'. Organic Syntheses. 10: 22. doi:10.15227/orgsyn.010.0022.CS1 maint: multiple names: authors list (link)
  2. ^Lev Tschugaeff (1905). 'Über ein neues, empfindliches Reagens auf Nickel'. Berichte der Deutschen Chemischen Gesellschaft. 38 (3): 2520–2522. doi:10.1002/cber.19050380317.
  3. ^Girolami, G. S.; Rauchfuss, T.B.; Angelici, R. J. (1999). Synthesis and Technique in Inorganic Chemistry: A Laboratory Manual (3rd ed.). pp. 213–215.

Structure Of Ni(dmg)2

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