Nitrosyl chloride
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| Names | |
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Preferred IUPAC name
Nitrosyl chloride
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Systematic IUPAC name
Nitrooyl chloride
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Other names
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| Identifiers | |
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3D model (Jmol)
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| ChemSpider | |
| ECHA InfoCard | 100.018.430 |
| EC Number | 220-273-1 |
| E number | E919 (glazing agents, ...) |
| MeSH | nitrosyl+chloride |
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PubChem CID
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| RTECS number | QZ7883000 |
| UN number | 1069 |
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| Properties | |
| NOCl | |
| Molar mass | 65.459 g mol−1 |
| Appearance | Yellow gas |
| Density | 2.872 mg mL−1 |
| Melting point | −59.4 °C (−74.9 °F; 213.8 K) |
| Boiling point | −5.55 °C (22.01 °F; 267.60 K) |
| Reacts | |
| Structure | |
| Dihedral, digonal | |
| Hybridisation | sp2 at N |
| 1.90 D | |
| Thermochemistry | |
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Std molar
entropy (S |
261.68 J K−1 mol−1 |
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Std enthalpy of
formation (ΔfH |
51.71 kJ mol−1 |
| Hazards | |
| Safety data sheet | inchem.org |
| NFPA 704 | |
| Related compounds | |
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Nitrosyl chloride is the chemical compound with the formula 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. It is a strong electrophile and oxidizing agent.
The molecule is bent. 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°.
Since nitrosyl chloride is chemically simple and stable at room temperature and below, it can be produced in many ways.
NOCl also arises from the combination of hydrochloric and nitric acids according to the following reaction:
In nitric acid, NOCl is readily oxidized into nitrogen dioxide. The presence of NOCl in aqua regia was described by Edmund Davy in 1831.
NOCl behaves as an electrophile and an oxidant in most of its reactions. With halide acceptors, for example antimony pentachloride, converts to nitrosonium salts:
In a related reaction, sulfuric acid gives nitrosylsulfuric acid, the mixed acid anhydride of nitrous and sulfuric acid:
NOCl reacts with silver thiocyanate to give silver chloride and the pseudohalogen nitrosyl thiocyanate:
Nitrosyl chloride is used to prepare metal nitrosyl complexes. With molybdenum hexacarbonyl, NOCl gives the dinitrosyldichloride complex:
Aside from its role in the production of caprolactam, NOCl finds some other uses In organic synthesis. It adds to alkenes to afford α-chloro oximes. The initial addition of NOCl follows the Markovnikov rule. Ketenes also add NOCl, giving nitrosyl derivatives:
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