Cupferron

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Cupferron
Cupferron
Names
Other names
cupferron
ammonium N-nitrosophenylhydroxylamine
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.004.713
Properties
C6H9N3O2
Molar mass 155.15 g/mol
Melting point 150 to 155 °C (302 to 311 °F; 423 to 428 K)
soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cupferron, the ammonium salt of N-nitroso-N-phenylhydroxylamine, is a common reagent for the complexation of metal ions. Its formula is NH4[C6H5N(O)NO]. The anion binds to metal cations through the two oxygen atoms, forming five-membered chelate rings.

Cupferron is prepared from phenylhydroxylamine and an NO+ source:

C6H5NHOH + C4H9ONO + NH3 → NH4[C6H5N(O)NO] + C4H9OH

References[edit]

  • C. S. Marvel "Cupferron" Organic Syntheses, Coll. Vol. 1, p. 177; Vol. 4, p. 19.
  • D. Van der Helm, L. L. Merritt Jnr, R. Degeilh and C. H. MacGillavry "The crystal structure of iron cupferron Fe(O2N2C6H5)3" Acta Crystallogr. (1965). 18, 355–362
  • Merck 13,2649; Beil. 16,IV,891