Cupferron
Encyclopedia
Cupferron, the ammonium salt of N-nitroso-N-phenylhydroxylamine, is a common reagent for the complexation
Complex (chemistry)
In chemistry, a coordination complex or metal complex, is an atom or ion , bonded to a surrounding array of molecules or anions, that are in turn known as ligands or complexing agents...

 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
Chelation
Chelation is the formation or presence of two or more separate coordinate bonds between apolydentate ligand and a single central atom....

 rings.

Cupferron is prepared from phenylhydroxylamine
Phenylhydroxylamine
Phenylhydroxylamine is the organic compound with the formula C6H5NHOH. It is an intermediate in the redox-related pair C6H5NH2 and C6H5NO. Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or O-phenylhydroxylamine, is C6H5ONH2.-Preparation and derivatives:This...

and an NO+ source:
C6H5NHOH + C4H9ONO + NH3 → NH4[C6H5N(O)NO] + C4H9OH
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