Wikipedia

Cyclopentadienyl nickel nitrosyl

Cyclopentadienyl nickel nitrosyl is an organonickel compound with the formula (C5H5)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] Its toxicity is said to be comparable to nickel tetracarbonyl.[2] The complex has C5v symmetry.

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.[Ni+]([N+]#[O-])
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:
GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 0: Will not burn. E.g. waterInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
0
1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

The compound reacts with lithium aluminium hydride to give the paramagnetic cluster (C5H5)4Ni4H3.[4]

The related pentamethylcyclopentadienyl complex (C5(CH3)5)NiNO is also known.[5]

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

See also

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References

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  1. ^ a b 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.
  2. ^ a b Jolly, P. W. (2012-12-02). The Organic Chemistry of Nickel: Organonickel Complexes. Elsevier. p. 464. ISBN 9780323146906.
  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 application 882747A  International Nickel Co.: "Process of Making Cyclopentadienyl Nickel Nitrosyl Compounds" filing date 11.22.1961
  7. ^ US 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 application 612084  Hubert T. Henderson/Shell Internationale: "Antiknock Fuels" filing date 06.28.1962
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