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Nitrosyl chloride

Names
Preferred IUPAC name Nitrosyl chloride
Systematic IUPAC name Nitrooyl chloride
Other names Nitrogen oxychloride Nitrosonium chloride
Identifiers
CAS Number	2696-92-6
3D model (JSmol)	Interactive image
ChemSpider	16641
ECHA InfoCard	100.018.430
EC Number	220-273-1
E number	E919 (glazing agents, ...)
MeSH	Nitrosyl+chloride
PubChem CID	17601
RTECS number	QZ7883000
UN number	1069
CompTox Dashboard (EPA)	DTXSID5051945
InChI InChI=1S/ClNO/c1-2-3Key: VPCDQGACGWYTMC-UHFFFAOYSA-N InChI=1S/ClNO/c1-2-3Key: VPCDQGACGWYTMC-UHFFFAOYSA-N InChI=1/ClNO/c1-2-3Key: VPCDQGACGWYTMC-UHFFFAOYAB
SMILES ClN=O
Properties
Chemical formula	ClNO
Molar mass	65.46 g/mol
Appearance	yellow gas, red liquid
Density	1.273 g/cm (liquid, -12 °C) 2.872 g/L (gas)
Melting point	-59.4 °C
Boiling point	-5.55 °C
Solubility in water	decomposes
Solubility in chlorocarbons	soluble
Structure
Molecular shape	sp at N
Dipole moment	1.90 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Highly toxic
NFPA 704 (fire diamond)	3 0 1W
Related compounds
Other anions	Nitrosyl fluoride Nitrosyl bromide
Other cations	Thionyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Nitrosyl chloride is the chemical compound NOCl. It is a yellow gas that is most commonly encountered as a decomposition product of aqua regia, a mixture of hydrochloric acid and nitric acid. The related nitrosyl halides nitrosyl fluoride, NOF, and nitrosyl bromide, NOBr, are also known.

Structure and synthesis

A double bond exists between N and O (distance = 1.16 Å) and a single bond between N and Cl (distance = 1.69 Å). The O-N-Cl angle is 113°.

NOCl can be prepared by the direct combination of chlorine and nitric oxide. Alternatively, nitrosylsulfuric acid and HCl also affords the compound:

HCl + NOHSO₄ → NOCl + H₂SO₄

It also arises from the combination of hydrochloric and nitric acids according to the following reaction:

HNO₃ + 3 HCl → Cl₂ + 2 H₂O + NOCl

Although this mixture was used for dissolving gold for a long time the first description of the gas was done by Edmund Davy in 1831.

Reactions

• NOCl reacts with halide acceptors to give the nitrosyl cation, . This species is available as NOBF₄.
• NOCl reacts with water to release HCl.
• Heating NOCl above 100°C gives back Cl₂ and NO.
• In organic synthesis, NOCl is often employed. It adds to alkenes to afford α-chloro oximes.
• NOCl photolyses to NO and a Cl radical.

Safety

NOCl is very toxic and irritating to the lungs, eyes and skin.

References

1. Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
2. L. J. Beckham, W. A. Fessler, M. A. Kise (1951). "Nitrosyl Chloride". Chemical Reviews. 48 (3): 319–396. doi:10.1021/cr60151a001.{{cite journal}}: CS1 maint: multiple names: authors list (link)
3. Edmund Davy (1830 - 1837). "Abstracts of the Papers Printed in the Philosophical Transactions of the Royal Society of London, Vol. 3". JSTOR: 27–29. JSTOR 110250. {{cite journal}}: Check date values in: |year= (help); Cite journal requires |journal= (help); Unknown parameter |titel= ignored (|title= suggested) (help)CS1 maint: year (link)
4. Ohno, M,; Naruse, N.; Terasawa, I. (1973). "7-cyanoheptanal". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 5, p. 266.

• Nitrosyl compounds
• Oxochlorides