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

SMILES

* [CH-]1C=CC=C1.N#[O+].[Ni]

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:

Pictograms

NFPA 704 (fire diamond)  |

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 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]

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[edit]

* Cyclopentadienyl
* Cyclopentadienyl complex
* Cyclopentadiene

## Notes[edit]

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 c Jolly, P. W. (2012-12-02). The Organic Chemistry of Nickel: Organonickel Complexes. Elsevier. 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.[1]

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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  | 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

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