Nitrosonium

Short description: Diatomic cation

Nitrosonium  |

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Names
Systematic IUPAC name

Oxidonitrogen(1+)[1]

Other names

Nitrosonium
Iminooxidanium

Identifiers

CAS Number

* 14452-93-8

3D model (JSmol)

* Interactive image

Abbreviations  | NO(+)
ChEBI |

* CHEBI:29120

ChemSpider |

* 76569

Gmelin Reference

| 456

PubChem CID

* 84878

InChI

* InChI=1S/NO/c1-2/q+1

Key: KEJOCWOXCDWNID-UHFFFAOYSA-N

SMILES

* N#[O+]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

The nitrosonium ion is NO+
, in which the nitrogen atom is bonded to an oxygen atom with a bond order of 3, and the overall diatomic species bears a positive charge. It can be viewed as nitric oxide with one electron removed. This ion is usually obtained as the following salts: NOClO
4, NOSO
4H (nitrosylsulfuric acid, more descriptively written ONSO
3OH) and NOBF
4. The ClO−
4 and BF−
4 salts are slightly soluble in acetonitrile CH
3CN. NOBF4 can be purified by sublimation at 200–250 °C and 0.01 mmHg (1.3 Pa).

NO+
is isoelectronic with CO, CN−
and N
2. It arises via protonation of nitrous acid:

HONO + H+ ⇌ NO+ \+ H2O

## Contents

* 1 Chemical properties
* 1.1 Hydrolysis
* 1.2 As a diazotizing agent
* 1.3 As an oxidizing agent
* 1.4 Nitrosylation of arenes
* 1.5 As a source of nitrosyl complexes
* 2 See also
* 3 References

## Chemical properties

### Hydrolysis

NO+
reacts readily with water to form nitrous acid:

NO+ \+ H
2O → HONO + H+

For this reason, nitrosonium compounds must be protected from water or even moist air. With base, the reaction generates nitrite:

NO+ \+ 2 NaOH → NaNO
2 \+ Na+ \+ H

### As a diazotizing agent

NO+
reacts with aryl amines, ArNH
2, to give diazonium salts, ArN+
2. The resulting diazonium group is easily displaced (unlike the amino group) by a variety of nucleophiles.

Reaction of nitrosonium with aniline to form a diazonium salt

### As an oxidizing agent

NO+
, e.g. as NOBF
4, is a strong oxidizing agent:[2]

* vs. ferrocene/ferrocenium, [NO]+
in CH
2Cl
2 solution has a redox potential of 1.00 V (or 1.46–1.48 V vs SCE),
* vs. ferrocene/ferrocenium, [NO]+
in CH
3CN solution has a redox potential of 0.87 V vs. (or 1.27–1.25 V vs SCE).

NOBF
4 is a convenient oxidant because the byproduct NO is a gas, which can be swept from the reaction using a stream of N
2. Upon contact with air, NO forms NO
2, which can cause secondary reactions if it is not removed. NO
2 is readily detectable by its characteristic orange color.

### Nitrosylation of arenes

Electron-rich arenes are nitrosylated using NOBF4.[3] One example involves anisole:

CH3OC6H5 \+ NOBF4 → CH3OC6H4NO + HBF4

Nitrosonium, NO+
, is sometimes confused with nitronium, NO+2, the active agent in nitrations. These species are quite different, however. Nitronium is a more potent electrophile than is nitrosonium, as anticipated by the fact that the former is derived from a strong acid (nitric acid) and the latter from a weak acid (nitrous acid).

### As a source of nitrosyl complexes

Main page: Chemistry:Metal nitrosyl complex

NOBF4 reacts with some metal carbonyl complexes to yield related metal nitrosyl complexes.[4] One must be careful that [NO]+ is transferred vs. electron transfer (see above).

(C6Et6)Cr(CO)3 \+ NOBF4 → [(C6Et6)Cr(CO)2(NO)]BF4 \+ CO

## See also

* Nitronium
* Nitric oxide

## References

1. ↑ Nomenclature of Inorganic Chemistry : IUPAC Recommendations 2005 (Red Book). Cambridge: The Royal Society of Chemistry. 2005. p. 315. ISBN 978-0-85404-438-2. https://archive.org/details/nomenclatureinor2005conn.
2. ↑ N. G. Connelly, W. E. Geiger (1996). "Chemical Redox Agents for Organometallic Chemistry". Chem. Rev. 96 (2): 877–910. doi:10.1021/cr940053x. PMID 11848774.
3. ↑ E. Bosch and J. K. Kochi. "Direct Nitrosation of Aromatic Hydrocarbons and Ethers with the Electrophilic Nitrosonium Cation". Journal of Organic Chemistry, 1994, volume 59, pp. 5573–5586.
4. ↑ T. W. Hayton, P. Legzdins, W. B. Sharp. "Coordination and Organometallic Chemistry of Metal-NO Complexes". Chemical Reviews 2002, volume 102, pp. 935–991.

* v
* t
* e

Nitric oxide signaling modulators

Forms|

* Nitroxyl anion (NO−; oxonitrate(1-), hyponitrite anion)
* Nitric oxide (NO⋅; nitrogen monoxide)
* Nitrosonium (NO+; nitrosyl cation)

Targets|

| sGC|

* Activators/stimulators: Ataciguat
* BAY 41-2272
* BAY 41-8543
* BAY 60-4552
* BI-703704
* Cinaciguat (BAY 58-2667)
* GSK-2181236A
* Praliciguat
* Riociguat (BAY 63-2521)
* Vericiguat

* Inhibitors: ODQ

|

NO donors
(prodrugs)|

* Nitrates: Diethylene glycol dinitrate (DEGDN)
* Erythritol tetranitrate (ETN)
* Ethylene glycol dinitrate (EGDN; nitroglycol)
* Isosorbide mononitrate (ISMN)
* Isosorbide dinitrate (ISDN)
* Itramin tosilate
* Mannitol hexanitrate
* Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
* NCX-466
* NCX-2216
* NCX-4016
* NCX 4040
* NCX-4215
* Nicorandil
* Nipradilol (K-351)
* Nitrate (NO−3)
* Nitroatorvastatin (NCX-6560)
* Nitroflurbiprofen (HCT-1026)
* Nitrofluvastatin
* Nitroglycerin (glyceryl trinitrate (GTN))
* Nitropravastatin (NCX-6550)
* Pentaerithrityl tetranitrate (PETN)
* Propatylnitrate
* Propylene glycol dinitrate (PGDN)
* Sodium trioxodinitrate (Angeli's salt)
* Tenitramine
* Trolnitrate

* Nitroso compounds/nitrites: Nitrite (NO−2); O-Nitroso compounds (alkyl nitrites): Amyl nitrite (isoamyl nitrite, isopentyl nitrite)
* Cyclohexyl nitrite
* Ethyl nitrite
* Hexyl nitrite
* Isobutyl nitrite (2-methylpropyl nitrite)
* Isopropyl nitrite
* Methyl nitrite
* n-Butyl nitrite
* Pentyl nitrite
* tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810
* S-Nitrosoalbumin (SNALB)
* S-Nitrosated AR545C
* S-Nitroso-N-acetylcysteine (SNAC)
* S-Nitroso-N-acetylpenicillamine (SNAP)
* S-Nitroso-N-valerylpenicillamine (SNVP)
* S-Nitrosocaptopril (SNO-Cap)
* S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
* S-Nitrosodiclofenac
* S-Nitrosoglutathione (GSNO, SNOG)
* SNO-t-PA
* SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A

* Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt
* Roussin's red salt
* Sodium nitroprusside (SNP)

* NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)
* Diethylenetriamine/NO (DETA/NO)
* GLO/NO
* JS-K
* Methylamine hexamethylene methylamine/NO (MAHMA/NO)
* PROLI/NO
* Spermine/NO (SPER/NO)
* V-PYRRO/NO

* Heterocyclic compounds: Furoxans: Furoxan
* REC15/2739; Sydnonimines: Feprosidnine
* Linsidomine (SIN-1)
* Molsidomine (SIN-10)
* Sydnonimine

* Unsorted: Cimlanod
* FK-409
* FR144220
* FR146881
* N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide

Enzyme
(inhibitors)|

| NOS|

| nNOS|

* 3-Bromo-7-nitroindazole
* 3-Chloroindazole
* 3-Chloro-5-nitroindazole
* 5-Nitroindazole
* 6-Nitroindazole
* 7-Nitroindazole
* A-84643
* Aminoguanidine (pimagedine)
* ARL-17477
* Indazole
* N5-(1-Iminoethyl)-L-ornithine (L-NIO)
* Nω-Methyl-L-arginine (L-NMA)
* Nω-Propyl-L-arginine (L-NPA)
* Nitroarginine (NNA, NOARG)
* Pentamidine isethionate
* TRIM

|

iNOS|

* 1-Amino-2-hydroxyguanidine
* 2-Ethylaminoguanidine
* 2-Iminopiperidine
* 1400W
* AEITU
* Aminoguanidine (pimagedine)
* AMT
* AR-C 102222
* BYK-191023
* Canavanine
* Cindunistat (SD-6010)
* EITU
* IPTU
* MITU
* N5-(1-Iminoethyl)-L-ornithine (L-NIO)
* N6-(1-Iminoethyl)-L-lysine (L-NIL)
* Nω-Methyl-L-arginine (L-NMA)
* Ronopterin (VAS-203)
* TRIM

eNOS|

* Aminoguanidine (pimagedine)
* N5-(1-Iminoethyl)-L-ornithine (L-NIO)
* Nω-Methyl-L-arginine (L-NMA)
* Nitroarginine (NNA, NOARG)

Unsorted|

* Asymmetric dimethylarginine (ADMA)
* CKD-712
* Guanidinoethyldisulfide (GED)
* GW-273629
* Indospicine
* KD-7040
* Nitroarginine methyl ester (NAME)
* NCX-456
* NXN-462
* ONO-1714
* VAS-2381

Arginase|

* ABH
* Nω-Hydroxy-L-arginine (NOHA)
* chlorogenic acid
* ginseng
* epicatechin
* ornithine
* norvaline
* lysine
* alpha aminoacids

CAMK|

* Calmidazolium
* W-7

Others|

* Precursors: L-Arginine
* Nω-Hydroxy-L-arginine (NOHA)

* Cofactors: NADPH
* FAD
* FMN
* Heme
* BH4
* CaM
* O2
* Ca2+

* Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
* ETB receptor antagonists (e.g., bosentan)
* L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
* Nebivolol (beta blocker)
* PDE5 inhibitors (e.g., sildenafil)
* Statins (e.g., simvastatin)

See also: Receptor/signaling modulators

* v
* t
* e

Nitrogen species

* Hydrides:
* NH3
* NH4+
* NH2− MNH2
* N3−
* NH2OH
* N2H4
* N3–
* Organic:
* -NH2
* -CHR=NHR
* -CONHR2
* HCN
* CN−
* C2N2
* H2NCN
* CH2N2
* Oxides:
* N2O
* NO
* NO2
* N2O3
* N2O4
* N2O5
* H2N2O2
* H4N2O4
* HNO2
* HNO3
* HONO3
* HN2O2−
* N2O22−
* NO2−
* ONOO−
* NO3−
* NO43−
* O2NOO−
* NO+
* NO2+
* Halides:
* NF3
* NCl3
* NBr3
* NI3
* FN3
* ClN3
* BrN3
* NH2Cl
* NHCl2

Chemical formulas

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