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	{{Chembox		{{Chembox
			|Watchedfields = changed
	| verifiedrevid = 444026971
			|verifiedrevid = 444028111
	| ImageFileL1 = Nitrosyl-chloride-2D-dimensions.png
			|ImageFile = Nitrosyl-chloride-2D-dimensions.png
	| ImageNameL1 = Wireframe model of nitrosyl chloride
			|ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFileR1 = Nitrosyl-chloride-3D-vdW.png
			|ImageSize = 200
	| ImageNameR1 = Spacefill model of nitrosyl chloride
	| PIN = Nitrosyl chloride		|ImageName = Skeletal formula of nitrosyl chloride with measurements
	| SystematicName = Nitrooyl chloride		|ImageFile1 = Nitrosyl-chloride-3D-vdW.png
			|ImageFile1_Ref = {{chemboximage|correct|??}}
	| OtherNames = Nitrogen oxychloride<br />
			|ImageSize1 = 200
	Nitrosonium chloride
			|ImageName1 = Spacefill model of nitrosyl chloride
	| Section1 = {{Chembox Identifiers
			|IUPACName = Nitrosyl chloride{{Citation needed|date=April 2012}}
	| InChI1 = 1/ClNO/c1-2-3
			|Section1={{Chembox Identifiers
	| InChIKey1 = VPCDQGACGWYTMC-UHFFFAOYAB
	| CASNo = 2696-92-6		|CASNo = 2696-92-6
	| CASNo_Ref = {{cascite|correct|CAS}}		|CASNo_Ref = {{cascite|correct|CAS}}
			|UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem = 17601
			|UNII = NHE5I1E5H6
	| PubChem_Ref = {{Pubchemcite}}
	| ChemSpiderID = 16641		|PubChem = 17601
			|ChemSpiderID = 16641
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| EINECS = 220-273-1		|EINECS = 220-273-1
	| UNNumber = 1069		|UNNumber = 1069
			|MeSHName = nitrosyl+chloride
	| RTECS = QZ7883000
			|RTECS = QZ7883000
	| MeSHName = Nitrosyl+chloride
			|SMILES = ClN=O
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/ClNO/c1-2-3		|StdInChI = 1S/ClNO/c1-2-3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = VPCDQGACGWYTMC-UHFFFAOYSA-N		|StdInChIKey = VPCDQGACGWYTMC-UHFFFAOYSA-N
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| SMILES = ClN=O
	| InChI = 1S/ClNO/c1-2-3
	| InChIKey = VPCDQGACGWYTMC-UHFFFAOYSA-N}}
	| Section2 = {{Chembox Properties
	| Formula = ClNO
	| MolarMass = 65.46 g/mol
	| Appearance = yellow gas, red liquid
	| Density = 1.273 g/cm<sup>3</sup> (liquid, -12 °C)<br/> 2.872 g/L (gas)
	| Solubility = decomposes
	| Solvent = chlorocarbons
	| SolubleOther = soluble
	| MeltingPt = -59.4 °C
	| BoilingPt = -5.55 °C
	}}
	| Section3 = {{Chembox Structure
	| MolShape = sp<sup>2</sup> at N
	| Dipole = 1.90 ]
	}}
	| Section7 = {{Chembox Hazards
	| ExternalMSDS =
	| EUIndex = Not listed
	| MainHazards = Highly toxic
	| RPhrases =
	| SPhrases =
	| NFPA-H = 3
	| NFPA-F = 0
	| NFPA-R = 1
	| NFPA-O = W
	}}
	| Section8 = {{Chembox Related
	| OtherAnions = ]<br/>]
	| OtherCations = ]
	| OtherCpds = ]<br/>]<br/>]<br/>]
	}}
	}}		}}
			|Section2={{Chembox Properties
			|Formula = NOCl
	'''Nitrosyl chloride''' is the ] NOCl. It is a yellow gas that is most commonly encountered as a decomposition product of ], a mixture of ] and ]. The related nitrosyl halides ], NOF, and ], NOBr, are also known.
			|MolarMass = 65.459 g mol<sup>−1</sup>
			|Appearance = yellow gas
			|Density = 2.872 mg mL<sup>−1</sup>
			|MeltingPtC = -59.4
			|BoilingPtC = -5.55
			|Solubility = Reacts
			}}
			|Section3={{Chembox Structure
			|MolShape = Dihedral, digonal
			|OrbitalHybridisation = sp<sup>2</sup> at N
			|Dipole = 1.90 D
			}}
			|Section4={{Chembox Thermochemistry
			|DeltaHf = 51.71 kJ mol<sup>−1</sup>
			|Entropy = 261.68 J K<sup>−1</sup> mol<sup>−1</sup>
			}}
			|Section5={{Chembox Hazards
			|ExternalSDS =
			|NFPA-H = 3
			|NFPA-F = 0
			|NFPA-R = 1
			|NFPA-S = W OX
			}}
			|Section6={{Chembox Related
			| OtherCompounds = {{Unbulleted list|]|]|]|]|]}}
			}}
			}}
			'''Nitrosyl chloride''' is the ] with the formula NOCl. It is a yellow gas that is commonly encountered as a component of ], a mixture of 3 parts concentrated ] and 1 part of concentrated ]. It is a strong ] and ]. It is sometimes called Tilden's reagent, after ], who was the first to produce it as a pure compound.<ref>{{cite journal |last1=Tilden |first1=William A. |title=XXXII.—On aqua regia and the nitrosyl chlorides |journal=J. Chem. Soc. |date=1874 |volume=27 |pages=630–636 |doi=10.1039/JS8742700630|url=https://zenodo.org/record/1716261 }}</ref>
	==Structure and synthesis==		==Structure and synthesis==
	A ] 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°.<ref>Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.</ref>		The molecule is bent. A ] exists between N and O (distance&nbsp;=&nbsp;1.16&nbsp;Å) and a single bond between N and Cl (distance&nbsp;=&nbsp;1.96&nbsp;Å). The O=N–Cl angle is 113°.<ref>{{cite book|last1=Holleman |first1=A. F.|last2= Wiberg |first2=E. |title=Inorganic Chemistry |publisher=Academic Press |location=San Diego |date=2001 |isbn=0-12-352651-5}}</ref>
			===Production===
	NOCl can be prepared by the direct combination of ] and ]. Alternatively, ] and HCl also affords the compound:
			Nitrosyl chloride can be produced in many ways.
	:HCl + NOHSO<sub>4</sub> &rarr; NOCl + ]
			* Combining ] and HCl affords the compound. This method is used industrially.<ref name=Ullmann/>
	It also arises from the combination of hydrochloric and nitric acids according to the following reaction:<ref>{{cite journal|title = Nitrosyl Chloride|author= L. J. Beckham, W. A. Fessler, M. A. Kise| journal= Chemical Reviews|pages=319–396|issue = 3| volume=48| year = 1951 |doi=10.1021/cr60151a001}}</ref>
	:HNO<sub>3</sub> + 3 HCl &rarr; Cl<sub>2</sub> + 2 H<sub>2</sub>O + NOCl		:HCl + NOHSO<sub>4</sub> → ] + NOCl
			* A more convenient laboratory method involves the (reversible) dehydration of ] by HCl<ref>{{cite book |first1=J. R. |last1=Morton |first2=H. W. |last2=Wilcox |first3=Therald |last3=Moellerf |first4=Delwin C. |last4=Edwards |editor-first=John C. Jr |editor-last=Bailar |title=Inorganic Syntheses |chapter=Nitrosyl Chloride |date=1953 |publisher=McGraw-Hill |volume=4 |page=48 |doi=10.1002/9780470132357.ch16 |isbn=9780470132357 |doi-access=free}}</ref>
	Although this mixture was used for dissolving gold for a long time the first description of the gas was done by ] in 1831.<ref>{{cite journal
			: HNO<sub>2</sub> + HCl → H<sub>2</sub>O + NOCl
	| titel = On a New Combination of Chlorine and Nitrous Gas.
			* By the direct combination of ] and ]; This reaction reverses above 100&nbsp;°C.
			: Cl<sub>2</sub> + 2&nbsp;NO → 2&nbsp;NOCl
			* By reduction of nitrogen dioxide with hydrogen chloride:<ref>{{Greenwood&Earnshaw2nd|page=456}}</ref>
			: 2NO<sub>2</sub> + 4&nbsp;HCl → 2NOCl + 2H<sub>2</sub>O + Cl<sub>2</sub>
			===Occurrence in aqua regia===
			NOCl also arises from the combination of hydrochloric and nitric acids according to the following reaction:<ref>{{cite journal|title = Nitrosyl Chloride|first1= L. J.|last1= Beckham |first2=W. A. |last2=Fessler |first3=M. A. |last3=Kise| journal= Chemical Reviews|pages=319–396|issue = 3| volume=48| year = 1951 |doi=10.1021/cr60151a001|pmid= 24541207}}</ref>
			:HNO<sub>3</sub> + 3&nbsp;HCl → 2 + 2&nbsp;H<sub>2</sub>O + NOCl
			In nitric acid, NOCl is readily oxidized into ]. The presence of NOCl in aqua regia was described by ] in 1831.<ref>{{cite journal
			| title = On a New Combination of Chlorine and Nitrous Gas
	| author = Edmund Davy		| author = Edmund Davy
	| title = Abstracts of the Papers Printed in the Philosophical Transactions of the Royal Society of London, Vol. 3.		| journal = Abstracts of the Papers Printed in the Philosophical Transactions of the Royal Society of London
			|volume= 3
	| year = 1830 - 1837
			| year = 1830–1837
	|pages = 27–29
	| publisher = ]		| pages = 27–29
	| jstor=110250}}</ref>		| jstor=110250}}</ref>
	==Reactions==		==Reactions==
			NOCl behaves as an electrophile and an oxidant in most of its reactions. With ] acceptors it gives ] salts, and synthesis of ] is typically performed in liquid NOCl:<ref name="Nitros">{{cite book|title=Nitrosation|first=D.&nbsp;L.&nbsp;H.|last=Williams|publisher=]|location=Cambridge, UK|year=1988|isbn=0-521-26796-X|url=https://archive.org/details/nitrosation0000will|url-access=registration|page=11}}</ref>
	*NOCl reacts with ] acceptors to give the nitrosyl cation, <sup>+</sup>. This species is available as ].
			: NOCl&nbsp;+ FeCl<sub>3</sub>&nbsp;→ <sup>+</sup><sup>−</sup>
	*NOCl reacts with water to release HCl.
	*Heating NOCl above 100°C gives back Cl<sub>2</sub> and NO.
			In a related reaction, sulfuric acid gives ], the mixed ] of nitrous and sulfuric acid:
	*In ], NOCl is often employed. It adds to ]s to afford α-chloro ]s.<ref>{{OrgSynth | author = Ohno, M,; Naruse, N.; Terasawa, I. | title =
			: ClNO + H<sub>2</sub>SO<sub>4</sub> → ONHSO<sub>4</sub> + HCl
	7-cyanoheptanal | collvol = 5 | collvolpages = 266 | year = 1973 | prep = cv5p0266}}</ref>
	*NOCl ] to NO and a Cl radical.
			NOCl reacts with silver thiocyanate to give ] and the ] nitrosyl thiocyanate:
			: ClNO + AgSCN → AgCl + ONSCN
			Similarly, it reacts with silver cyanide to give ].<ref name=Kirby>{{cite journal |doi=10.1039/CS9770600001|title=Tilden Lecture. Electrophilic C-Nitroso Compounds|year=1977|last1=Kirby|first1=G. W.|journal=Chemical Society Reviews|volume=6|page=1}}</ref>
			Nitrosyl chloride is used to prepare ]es. With ], NOCl gives the dinitrosyldichloride complex:<ref>{{cite book|first1=B. F. G. |last1=Johnson |first2=K. H. |last2=Al-Obadi |title=Inorganic Syntheses |chapter=Dihalogenodinitrosylmolybdenum and Dihalogenodinitrosyltungsten |journal=Inorg. Synth.|year=1970 |volume= 12 |pages= 264–266 |doi=10.1002/9780470132432.ch47|isbn=9780470132432 }}</ref>
			:Mo(CO)<sub>6</sub> + 2&nbsp;NOCl → MoCl<sub>2</sub>(NO)<sub>2</sub> + 6&nbsp;CO
			It dissolves platinum:<ref>{{cite book |doi=10.1002/9780470132555.ch63|chapter=Nitrosyl Hexachloroplatinate(IV)|year=1986|volume=24|last1=Moravek|first1=Richard T.|title=Inorganic Syntheses|pages=217–220|isbn=9780470132555}}</ref>
			:Pt + 6&nbsp;NOCl → (NO<sup>+</sup>)<sub>2</sub><sup>2-</sup> + 4&nbsp;NO
			===Applications in organic synthesis===
			Aside from its role in the production of caprolactam, NOCl finds some other uses in ]. It adds to ]s to afford α-chloro ]s.<ref>{{cite journal | last1= Ohno |first1=M. |last2=Naruse |first2=N. |last3=Terasawa |first3=I. | title =7-Cyanoheptanal |journal=Org. Synth. | volume = 49 | page = 27 | year = 1969 | doi = 10.15227/orgsyn.049.0027}}</ref> The addition of NOCl follows the ]. ]s also add NOCl, giving nitrosyl derivatives:
			: H<sub>2</sub>C=C=O + NOCl → ONCH<sub>2</sub>C(O)Cl
			]s ]; and then NOCl attacks the nucleophilic end of the alkene to give a vicinal keto- or aldo-oxime.{{sfn|Williams|1988|p=11}}
			]s react with NOCl to give an α-chloronitritoalkyl derivatives. In the case of propylene oxide, the addition proceeds with high regiochemistry:<ref>{{cite journal|title=Olefin Oxides. IX. Condensation of Olefin Oxides with Nitrosyl Chloride|last1= Malinovskii |first1=M. S. |last2=Medyantseva |first2=N. M.|journal= Zhurnal Obshchei Khimii|year=1953|volume=23|pages=84–6 }} (translated from Russian)</ref>
			:]
			It converts amides to ''N''-nitroso derivatives.<ref>{{cite journal|first1=A. M. |last1=Van Leusen |first2=J. |last2=Strating |title=''p''-Tolylsulfonyldiazomethane |journal=Org. Synth.|date= 1977 |volume= 57 |page=95 |doi=10.15227/orgsyn.057.0095}}</ref> NOCl converts some cyclic amines to the alkenes. For example, ] reacts with NOCl to give ], ] and ].
			==Industrial applications==
			NOCl and ] react ] to give ] hydrochloride. This process exploits the tendency of NOCl to undergo ] into NO and Cl radicals. The cyclohexanone oxime is converted to ], a precursor to ].<ref name=Ullmann>{{Ullmann|first1=Josef |last1=Ritz |first2=Hugo |last2=Fuchs |first3=Heinz |last3=Kieczka |first4=William C. |last4=Moran |chapter=Caprolactam |publisher=Wiley-VCH |location=Weinheim |date=2002 |doi=10.1002/14356007.a05_031|isbn=3527306730}}</ref>{{sfn|Williams|1988|p=12}}
			==Historical importance==
			Before the advent of modern spectroscopic methods for chemical analysis, informative chemical degradation and structure elucidation required the characterization of the individual
			components of various extracts. Notably, the aforementioned introduction of nitrosyl chloride by Tilden in 1875, as a reagent for producing crystalline derivatives of terpenes, e.g. α-pinene from oil of turpentine allowed investigators to readily distinguish one terpene from another.:<ref>{{cite journal|title=The development of strategies for terpenoid structure determination|last1= Hanson|first1=J.S. |journal= Natural Product Reports|year=2001|volume=18|issue= 6|pages=607–617 |doi=10.1039/b103772m}}</ref>
	==Safety==		==Safety==
	NOCl is very toxic and irritating to the lungs, eyes and skin.		Nitrosyl chloride is very toxic and irritating to the lungs, eyes, and skin.
	==References==		==References==
	{{reflist}}		{{reflist}}
			==External links==
	{{DEFAULTSORT:Nitrosyl Chloride}}
			*{{Commonscatinline}}
	]
	]
			{{Chlorides}}
			]
	]
			]
	]
			]
	]
			]
	]
			]
	]
	]
	]
	]
	]
	]
	]
	]