Bis(cyclooctadiene)nickel(0)

Bis(cyclooctadiene)nickel(0) is the organonickel compound with the formula Ni(C8H12)2. This highly air-sensitive yellow solid is a common source of Ni(0) in chemical synthesis.[1] If exposed to air at room temperature, decomposition to nickel(II) oxide is rapid,[2] occurring in minutes. As a result, this compound is generally handled in a glovebox.[3][4]

Bis(cyclooctadiene)nickel(0)
Names
Other names
nickel biscod, Ni(COD)2
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.702
EC Number
  • 215-072-0
RTECS number
  • QR6135000
UN number 1325
Properties
C16H24Ni
Molar mass 275.06 g/mol
Appearance Yellow solid
Melting point 60 °C (140 °F; 333 K) (N2, decomposes)
Solubility soluble in benzene, tetrahydrofuran, toluene, diethyl ether, dimethylformamide
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H228, H317, H334, H350, H351
P201, P202, P210, P240, P241, P261, P272, P280, P281, P285, P302+352, P304+341, P308+313, P321, P333+313, P342+311, P363, P370+378, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Bis(cyclooctadiene)nickel(0), or Ni(cod)2, is a diamagnetic coordination complex featuring tetrahedral nickel(0) bound to the alkene groups in two 1,5-cyclooctadiene ligands. The complex is prepared by reduction of anhydrous nickel(II) acetylacetonate in the presence of the diolefin:

1/3 [Ni3(acac)6] + 2 cod + 2 AlEt3 → Ni(cod)2 + 2 acacAlEt2 + C2H6 + C2H4

Ni(cod)2 is moderately soluble in several organic solvents.[5][6] One or both 1,5-cyclooctadiene ligands are readily displaced by phosphines, phosphites, bipyridine, and isocyanides.

References
  1. Wilke, G. (1988). "Contributions to Organo-Nickel Chemistry". Angewandte Chemie International Edition. 27 (1): 185–206. doi:10.1002/anie.198801851.
  2. Zhu, Kake; D'Souza, Lawrence; Richards, Ryan M. (September 2005). "Planting of bis(1,5-cyclooctadiene) nickel upon silica to harvest NiO (<5 nm) nanoparticles in a silica matrix". Applied Organometallic Chemistry. 19 (9): 1065–1069. doi:10.1002/aoc.974.
  3. "The Garg Research Group at UCLA". www.tcichemicals.com. Retrieved 18 May 2019.
  4. Tasker, Sarah Z.; Standley, Eric A.; Jamison, Timothy F. (2014). "Recent advances in homogeneous nickel catalysis". Nature. 509 (7500): 299–309. doi:10.1038/nature13274. PMC 4344729. PMID 24828188.
  5. Schunn, R. A.; Ittel, S. D.; Cushing, M. A. (1990). Bis(1,5-Cyclooctadiene)Nickel(0). Inorganic Syntheses. 28. pp. 94–98. doi:10.1002/9780470132593.ch25. ISBN 978-0-470-13259-3.
  6. Wender, Paul A.; Smith, Thomas E.; Duong, Hung A.; Louie, Janis; Standley, Eric A.; Tasker, Sarah Z. (2015). "Bis(1,5-cyclooctadiene)nickel(0)". Encyclopedia of Reagents for Organic Synthesis. American Cancer Society: 1–15. doi:10.1002/047084289x.rb118.pub3.
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