Not to be confused with Nitrosonium, a separate nitrogen-oxygen cation.
Nitronium ion
Skeletal formula of nitronium with some dimensions added
Spacefill model of nitronium
Names
IUPAC name
Nitronium ion
Systematic IUPAC name
Dioxidonitrogen(1+)[1]
Identifiers
CAS Number
12269-46-4
3D model (JSmol)
Interactive image
ChEBI
CHEBI:29424
ChemSpider
2844644Y
PubChem CID
3609161
CompTox Dashboard (EPA)
DTXSID60893596
InChI
InChI=1S/NO2/c2-1-3/q+1
Key: OMBRFUXPXNIUCZ-UHFFFAOYSA-N
SMILES
O=[N+]=O
Properties
Chemical formula
[NO2]+
Molar mass
46.005 g·mol−1
Thermochemistry
Std molar entropy (S⦵298)
233.86 J K−1 mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
The nitronium ion, [NO2]+, is a cation. It is an onium ion because its nitrogen atom has +1 charge, similar to ammonium ion [NH4]+. It is created by the removal of an electron from the paramagnetic nitrogen dioxide molecule NO2, or the protonation of nitric acid HNO3 (with removal of H2O).[2]
It is stable enough to exist in normal conditions, but it is generally reactive and used extensively as an electrophile in the nitration of other substances. The ion is generated in situ for this purpose by mixing concentrated sulfuric acid and concentrated nitric acid according to the equilibrium:
H2SO4 + HNO3 → HSO−4 + [NO2]+ + H2O
^"dioxidonitrogen(1+) (CHEBI:29424)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
^Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
The nitroniumion, [NO2]+, is a cation. It is an onium ion because its nitrogen atom has +1 charge, similar to ammonium ion [NH4]+. It is created by the...
the nitroniumion (NO2+), which is the active species in aromatic nitration. This active ingredient, which can be isolated in the case of nitronium tetrafluoroborate...
intermediates. The nitration of benzene is achieved via the action of the nitroniumion as the electrophile. The sulfonation with fuming sulfuric acid gives...
no more than one atom, for example, the protonitronium ion O=N+=O+—H (a protonated nitroniumion). And, in distonic superelectrophiles, they are separated...
chlorine. Pure solid N2O5 is a salt, consisting of separated linear nitroniumions NO+2 and planar trigonal nitrate anions NO−3. Both nitrogen centers...
formation of the nitroniumion (NO2+), followed by an electrophilic aromatic substitution reaction of it with benzene. The nitroniumion is generated by...
sometimes confused with nitronium, NO+ 2, the active agent in nitrations. These species are quite different, however. Nitronium is a more potent electrophile...
cation is the nitroniumion (O=N+=O). Linear geometry also occurs in AX2E3 molecules, such as xenon difluoride (XeF2) and the triiodide ion (I−3) with one...
using a mixture of nitric acid and sulfuric acid, which produce the nitroniumion (NO+2), which is the electrophile: + H+ The nitration product produced...
sulfuric acid acts both as an acid and a dehydrating agent, forming the nitroniumion NO+2, which is important in nitration reactions involving electrophilic...
H2SO4 ⇌ [NO2]+ + [H3O]+ + 2 HSO−4; Equilibrium constant: K ≈ 22 The nitroniumion, [NO2]+, is the active reagent in aromatic nitration reactions. Since...
a polyatomic ion with a positive charge that contains oxygen. Dioxygenyl ion, O+ 2 Nitrosonium ion,NO+ Nitroniumion, NO+ 2 Vanadyl ion, VO2+, a very...
Richard; Garfunkel, Eric; He, Huixin (4 April 2012). "Microwave- and NitroniumIon-Enabled Rapid and Direct Production of Highly Conductive Low-Oxygen...
First, the nitroniumion is formed from nitric acid and sulfuric acid. 2-(1-methylpropyl)phenol takes up the nitroniumion to form the arenium ion, which...
ions such as iminium and nitrilium. A simple onium ion has a charge of +1. A larger ion that has two onium ion subgroups is called a double onium ion...
different from an electrophilic aromatic substitution reaction in which nitroniumions are the electrophile. The addition of glycerol results in an exothermic...
Maciejko, James J.; Busman, Stanley C. (1973). "Reaction between azide and nitroniumions. Formation and decomposition of nitryl azide". J. Am. Chem. Soc. 95...
conditions, since the nitrate ion is a much weaker ligand than water, and if water is present the simple nitrate of the hydrated metal ion will form. The anhydrous...
rise to nitrogen oxide which forms strong metal nitrosyl complexes; nitroniumions (NO2+) are similarly obversed. In some cases, nitrate complexes are...
tetraperchloratoaluminate ion results. When hydrated aluminium nitrate reacts with dinitrogen pentoxide it forms a nitronium salt: [NO2]+[Al(NO3)4]−. A...
derivatives are useful detergents. In nitration, benzene reacts with nitroniumions (NO2+), which is a strong electrophile produced by combining sulfuric...
there can be metal cations, quaternary ammonium cations or other ions, for example, nitronium cation (NO+2). The term perchlorate can also describe perchlorate...
one can heat aluminium nitrate in the presence of nitrosonium or nitronium perchlorate at a temperature of 125 °C: 10–14 [NO]ClO4 + Al(NO3)3 → [NO2]3[Al(ClO4)6]...
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