Nitrosylsulfuric acid

Source: Wikipedia, the free encyclopedia.
Nitrosylsulfuric acid
Structural formula of nitrosylsulfuric acid
Ball-and-stick model of the nitrosylsulfuric acid molecule
Names
IUPAC name
Nitrosylsulfuric acid
Other names
nitrosonium bisulfate, chamber crystals
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.029.058 Edit this at Wikidata
UNII
  • InChI=1S/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5) checkY
    Key: VQTGUFBGYOIUFS-UHFFFAOYSA-N checkY
  • InChI=1/HNO5S/c2-1-6-7(3,4)5/h(H,3,4,5)
    Key: VQTGUFBGYOIUFS-UHFFFAOYAM
  • O=NOS(=O)(=O)O
Properties
HSO4NO
Molar mass 127.08 g/mol
Appearance Pale yellow crystals[1]
Density 1.865 g/mL in
40% sulfuric acid soln [2]
Melting point 70 °C (158 °F; 343 K)[1]
Boiling point Decomposes
Decomposes
Solubility Soluble in H2SO4[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Oxidizer
Related compounds
Other anions
 NOCl
Other cations
 NaHSO4
Related compounds
NOBF4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Nitrosylsulfuric acid is the

anhydride of sulfuric acid and nitrous acid
.

In organic chemistry, it is used as a reagent for

diazotizing agent, and as an oxidizing agent.[1]

Synthesis and reactions

A typical procedure entails dissolving sodium nitrite in cold sulfuric acid:[4][5]

HNO2 + H2SO4 → HSO4NO + H2O

It can also be prepared by the reaction of nitric acid and sulfur dioxide.[6]

HSO4NO is used in

diazonium salts from amines, for example in the Sandmeyer reaction. Related NO-delivery reagents include nitrosonium tetrafluoroborate [NO]+[BF4]− and nitrosyl chloride
.

In industry, the nitrosodecarboxylation reaction between nitrosylsulfuric acid and cyclohexanecarboxylic acid is used to generate caprolactam:[3]

Safety

Nitrosylsulfuric acid is a hazardous material and precautions are indicated.[1]

References

  1. ^
    ISBN 978-0471936237. {{cite book}}: |journal= ignored (help)CS1 maint: multiple names: authors list (link
    )
  2. ^ "Nitrosylsulfuric acid solution". Merck.
  3. ^
    ISBN 978-3527306732
    .
  4. ^ Hodgson, H. H.; Mahadevan, A. P.; Ward, E. R. (1955). "1,4-Dinitronaphthalene". Organic Syntheses; Collected Volumes, vol. 3, p. 341. (diazodization followed by treatment with nitrite)
  5. ^ Sandin, R. B.; Cairns, T. L. (1943). "1,2,3-Triiodo-5-nitrobenzene". Organic Syntheses; Collected Volumes, vol. 2, p. 604. (diazodization followed by treatment with iodide)
  6. ISBN 9780470132326
    . This procedure generates the nitrosylsulfuric acid as an intermediate en route to NOCl.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Nitrosylsulfuric_acid&oldid=1217244999"