Nitronium ion
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| Names | |||
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| IUPAC name
Nitronium ion
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| Systematic IUPAC name
Dioxidonitrogen(1+)[1] | |||
| Identifiers | |||
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3D model (JSmol)
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PubChem CID
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| Properties | |||
| Page Module:Chem2/styles.css has no content.[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).
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Template:Chembox Footer/trackingTemplate:Short description
The nitronium ion, Page Module:Chem2/styles.css has no content.[NO2]+, is a cation. It is an onium ion because its nitrogen atom has +1 charge, similar to ammonium ion Page Module:Chem2/styles.css has no content.[NH4]+. It is created by the removal of an electron from the paramagnetic nitrogen dioxide molecule Page Module:Chem2/styles.css has no content.NO2, or the protonation of nitric acid Page Module:Chem2/styles.css has no content.HNO3 (with removal of Page Module:Chem2/styles.css has no content.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:
- Page Module:Chem2/styles.css has no content.H2SO4 + HNO3 → HSO−4 + [NO2]+ + H2O
Structure
The nitronium ion is isoelectronic with carbon dioxide and has the same linear structure and bond angle of 180°. For this reason it has a similar vibrational spectrum to carbon dioxide. Historically, the nitronium ion was detected by Raman spectroscopy, because its symmetric stretch is Raman-active but infrared-inactive. The Raman-active symmetrical stretch was first used to identify the ion in nitrating mixtures.[3]
Salts
A few stable nitronium salts with anions of weak nucleophilicity can be isolated. These include nitronium perchlorate Page Module:Chem2/styles.css has no content.[NO2]+[ClO4]−, nitronium tetrafluoroborate Page Module:Chem2/styles.css has no content.[NO2]+[BF4]−, nitronium hexafluorophosphate Page Module:Chem2/styles.css has no content.[NO2]+[PF6]−, nitronium hexafluoroarsenate Page Module:Chem2/styles.css has no content.[NO2]+[AsF6]−, and nitronium hexafluoroantimonate Page Module:Chem2/styles.css has no content.[NO2]+[SbF6]−. These are all very hygroscopic compounds.[4]
The solid form of dinitrogen pentoxide, Page Module:Chem2/styles.css has no content.N2O5, actually consists of nitronium and nitrate ions, so it is an ionic compound, nitronium nitrate Page Module:Chem2/styles.css has no content.[NO2]+[NO3]−, not a molecular solid. However, dinitrogen pentoxide in liquid or gaseous state is molecular and does not contain nitronium ions.[2][5]
Related species
The compounds nitryl fluoride, Page Module:Chem2/styles.css has no content.NO2F, and nitryl chloride, Page Module:Chem2/styles.css has no content.NO2Cl, are not nitronium salts but molecular compounds, as shown by their low boiling points (−72 °C and −6 °C respectively) and short nitrogen–halogen bond lengths (N–F 135 pm, N–Cl 184 pm).[6]
Addition of one electron forms the neutral nitryl radical, Page Module:Chem2/styles.css has no content.NO2•; in fact, this is fairly stable and known as the compound nitrogen dioxide.
The related negatively charged species is Page Module:Chem2/styles.css has no content.NO−2, the nitrite ion.
See also
References
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- ^ Page Module:Citation/CS1/styles.css has no content."dioxidonitrogen(1+) (CHEBI:29424)". Chemical Entities of Biological Interest (ChEBI). UK: European Bioinformatics Institute.
- ^ a b Page Module:Citation/CS1/styles.css has no content.Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. doi:10.1016/C2009-0-30414-6. ISBN 978-0-08-037941-8.
- ^ Page Module:Citation/CS1/styles.css has no content.Ingold, C. K.; Millen, D. J.; Poole, H. G. (1946). "Spectroscopic Identification of the Nitronium Ion". Nature. 158 (4014): 480–481. Bibcode:1946Natur.158..480I. doi:10.1038/158480c0. S2CID 4106964.
- ^ Page Module:Citation/CS1/styles.css has no content.Kenneth Schofield (1980). Aromatic nitration. CUP Archive. p. 88. ISBN 0-521-23362-3.
- ^ Page Module:Citation/CS1/styles.css has no content.Cantrell, C. A.; Davidson, J. A.; McDaniel, A. H.; Shetter, R. E.; Calvert, J. G. (1988). "The equilibrium constant for N2O5⇄NO2+NO3: Absolute determination by direct measurement from 243 to 397 K". The Journal of Chemical Physics. 88 (8): 4997–5006. doi:10.1063/1.454679.
- ^ F. A. Cotton and G.Wilkinson, Advanced Inorganic Chemistry, 5th edition (1988), Wiley, p.333
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