Cyclopentadienyl nickel nitrosyl

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
CAS Number
  • 12071-73-7
3D model (JSmol)
  • Interactive image
ChemSpider
  • 65322142
PubChem CID
  • 42621475
InChI
  • 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
Chemical formula
 (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)
Solubility in water
 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).
Infobox references
Chemical compound

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.

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

References

  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
  • v
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  • e
Salts and covalent derivatives of the Cyclopentadienide ion
CpH He
LiCp Be B CpMe N C5H4O F Ne
NaCp MgCp2

MgCpBr

Al Si P S Cl Ar
K CaCp2 ScCp3 TiCp2Cl2

(TiCp2Cl)2
TiCpCl3
TiCp2S5
TiCp2(CO)2
TiCp2Me2

VCp2

VCpCh
VCp2Cl2
VCp(CO)4

CrCp2

(CrCp(CO)3)2

MnCp2 FeCp2

Fe(η5-C5H4Li)2
((C5H5)Fe(C5H4))2
(C5H4-C5H4)2Fe2
FeCp2PF6
FeCp(CO)2I

CoCp2

CoCp(CO)2

NiCp2

NiCpNO

Cu Zn Ga Ge As Se Br Kr
Rb Sr Y(C5H5)3 ZrCp2Cl2

ZrCp2ClH

NbCp2Cl2 MoCp2H2

MoCp2Cl2
(MoCp(CO)3)2

Tc RuCp2

RuCp(PPh3)2Cl
RuCp(MeCN)3PF6

RhCp2 PdCp(C3H5) Ag Cd InCp SnCp2 Sb Te I Xe
Cs Ba * LuCp3 HfCp2Cl2 Ta (WCp(CO)3)2 ReCp2H OsCp2 IrCp2 Pt Au Hg TlCp PbCp2 Bi Po At Rn
Fr Ra ** Lr Rf Db Sg Bh HsCp2 Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
 
* LaCp3 CeCp3 PrCp3 NdCp3 PmCp3 SmCp3 Eu Gd Tb DyCp3 Ho ErCp3 TmCp3 YbCp3
** Ac ThCp3
ThCp4 		Pa UCp4 Np Pu Am Cm Bk Cf Es Fm Md No