Cyclopentadienyl nickel nitrosyl

Cyclopentadienyl nickel nitrosyl is a highly toxic organonickel chemical. In its pure form, it is a diamagnetic, volatile, relatively air-stable liquid with a blood-red color. It has been reported to be the simplest mono-cyclopentadienyl metal complex.[2] The chemical was discovered in 1954 by a team at The International Nickel Company.[3] The molecular formula is (C5H5)NiNO. It can be prepared by treating nickelocene with nitric acid.[4] It is extremely toxic (T+), and is considered to be one of the most poisonous organometallic chemicals ever developed. Its toxicity is said to be comparable to nickel tetracarbonyl.[2]

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
  • InChI=1S/C5H5.NO.Ni/c1-2-4-5-3-1;1-2;/h1-5H;;/q-1;+1;
    Key: RUGUYOINVVZVCI-UHFFFAOYSA-N
  • [CH-]1C=CC=C1.N#[O+].[Ni]
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
Occupational safety and health (OHS/OSH):
Main hazards
 Extremely Toxic (T+)
GHS labelling:
NFPA 704 (fire diamond)
4
0
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Due to its high toxicity, cyclopentadienyl nickel nitrosyl has very limited usage. It was patented as a fuel additive and anti-caking agent, but it was never used for these purposes due to the health hazards it posed.[2] In the past, it was also studied for its spectroscopic qualities, and saw limited use as a catalyst in organic chemical reactions, but it has since been discounted in favor of less toxic compounds.

See also

Notes
  1. Herrmann, Wolfgang A. (2014-05-14). Synthetic Methods of Organometallic and Inorganic Chemistry, Volume 8, 1997: Volume 8: Transition Metals. p. 89. ISBN 9783131792419.
  2. Jolly, P. W. (2012-12-02). The Organic Chemistry of Nickel: Organonickel Complexes. p. 464. ISBN 9780323146906.
  3. US Patent 3088959 – Process of making cyclopentadienyl nickel nitrosyl compounds
  4. Pauling, Linus (1960). The nature of the chemical bond and the structure of molecules and crystals : an introduction to modern structural chemistry. Ithaca, N.Y: Cornell University Press. ISBN 978-0-8014-0333-0.


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