Chemistry:Cyclopentadienyl nickel nitrosyl

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Cyclopentadienyl nickel nitrosyl
Names
IUPAC name
azanylidyneoxidanium;cyclopenta-1,3-diene;nickel
Other names
Cyclopentadienylnickelnitrosyl (6CI);

Nickel, nitrosylcyclopentadienyl- (7CI);
Nickel, p-cyclopentadienylnitrosyl- (8CI);
(Cyclopentadienyl)nitrosylnickel;;
(h5-Cyclopentadienyl)(nitrosyl)nickel;
Cyclopentadienylnitrosylnickel(II);

p-Cyclopentadienylnitrosylnickel
Identifiers
3D model (JSmol)
ChemSpider
Properties
(C5H5)NiNO
Molar mass 153.7927 g/mol
Appearance Blood-red liquid
Odor Unpleasant, disagreeable[1]
Melting point −41 °C (−42 °F; 232 K)
Boiling point 144–145 °C (291–293 °F; 417–418 K)
Insoluble[1]
Solubility Very soluble in all organic compounds
Hazards
Main hazards Extremely Toxic (T+)
GHS pictograms GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondFlammability code 0: Will not burn. E.g. waterHealth code 4: Very short exposure could cause death or major residual injury. E.g. VX gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
0
4
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Cyclopentadienyl nickel nitrosyl is an organonickel compound with the formula (C
5H
5)NiNO. It is a diamagnetic, volatile, relatively air-stable red liquid. It has been reported to be the simplest mono-cyclopentadienyl metal complex.[2] It is prepared by treating nickelocene with nitric oxide.[3] The complex has C5v symmetry.

The compound reacts with lithium aluminium hydride to give the paramagnetic cluster (C
5H
5)
4Ni
4H
3.[4]

The related pentamethylcyclopentadienyl complex (C
5(CH
3)
5)NiNO is also known.[5]

Cyclopentadienyl nickel nitrosyl was the subject of several patents as a fuel additive.[6][7][8]

Safety

Its toxicity is said to be comparable to nickel tetracarbonyl.[2]

See also

References

  1. ↑ 1.0 1.1 Herrmann, Wolfgang A. (2014-05-14). Synthetic Methods of Organometallic and Inorganic Chemistry, Volume 8, 1997: Volume 8: Transition Metals. Thieme. p. 89. ISBN 9783131792419. https://books.google.com/books?id=nouZAwAAQBAJ&q=Cyclopentadienyl+nickel+nitrosyl+poison&pg=PA89. 
  2. ↑ 2.0 2.1 Jolly, P. W. (2012-12-02). The Organic Chemistry of Nickel: Organonickel Complexes. Elsevier. p. 464. ISBN 9780323146906. https://books.google.com/books?id=2KTdG3xA0eIC&q=Cyclopentadienyl+nickel+nitrosyl+toxic&pg=PA464. 
  3. ↑ Piper, T.S.; Cotton, F.A.; Wilkinson, G. (1955). "Cyclopentadienyl-Carbon Monoxide and Related Compounds of Some Transitional Metals". Journal of Inorganic and Nuclear Chemistry 1 (3): 165–174. doi:10.1016/0022-1902(55)80053-x. 
  4. ↑ Koetzle, Thomas F.; Mueller, Joern; Tipton, Donald L.; Hart, Donald W.; Bau, Robert (1979). "Neutron diffraction analysis of the structure of tetrakis(.eta.-cyclopentadienyl)trihydrotetranickel". Journal of the American Chemical Society 101 (19): 5631–5637. doi:10.1021/ja00513a030. 
  5. ↑ Fomitchev, Dmitry V.; Furlani, Thomas R.; Coppens, Philip (1998). "Combined X-ray Diffraction and Density Functional Study of [Ni(NO)(η5-Cp*)] in the Ground and Light-Induced Metastable States". Inorganic Chemistry 37 (7): 1519–1526. doi:10.1021/ic9713644. 
  6. ↑ GB patent application 882747A International Nickel Co.: "Process of Making Cyclopentadienyl Nickel Nitrosyl Compounds" filing date 11.22.1961
  7. ↑ US patent application 3006742 Jerome E. Brown, Hymin Shapiro, Earl G. DeWitt/Ethyl Corporation: "Metal Cyclopentadienyl Compounds as Antiknock Additives" filing date 10.31.1961
  8. ↑ BE patent application 612084 Hubert T. Henderson/Shell Internationale: "Antiknock Fuels" filing date 06.28.1962

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