Cupferron

Cupferron
Names
	Other names cupferron; ammonium N-nitrosophenylhydroxylamine
Identifiers
CAS Number	135-20-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	2006262 ;
ECHA InfoCard	100.004.713
PubChem CID	2724103;
UNII	V66QK963ED ;
CompTox Dashboard (EPA)	DTXSID1020352 ;
	InChI InChI=1S/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1 Key: GDEBSAWXIHEMNF-UHFFFAOYSA-O ; InChI=1/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1 Key: GDEBSAWXIHEMNF-IKLDFBCSAP;
	SMILES O=NN([O-])c1ccccc1.[NH4+];
Properties
Chemical formula	C6H9N3O2
Molar mass	155.15 g/mol
Melting point	150 to 155 °C (302 to 311 °F; 423 to 428 K)
Solubility in water	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 is jargon for the ammonium salt of the conjugate base derived from N-nitroso-N-phenylhydroxylamine. It once was a common reagent for the complexation of metal ions, being of interest in the area of qualitative inorganic analysis. Its formula is NH₄[C₆H₅N(O)NO]. The anion binds to metal cations through the two oxygen atoms, forming five-membered chelate rings.

Synthesis and complexes

Cupferron is prepared from phenylhydroxylamine and an NO⁺ source:[1]

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

Being a bidentate mono-anionic ligand, CU⁻ forms complexes analogous to those produced with acetylacetonate. Illustrative complexes include Cu(CU)₂, Fe(CU)₃, and Zr(CU)₄.[2][3][4]

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References

C. S. Marvel (1925). "Cupferron". Organic Syntheses. 4: 19. doi:10.15227/orgsyn.004.0019.
Elerman, Y.; Atakol, O.; Svoboda, I.; Geselle, M. (1995). "Bis(cupferronato)copper(II), [Cu(C6H5N2O2)2]". Acta Crystallographica Section C Crystal Structure Communications. 51 (8): 1520–1522. doi:10.1107/S0108270195002770.
Van Der Helm, D.; Merritt, L. L.; Degeilh, R.; MacGillavry, C. H. (1965). "The crystal structure of iron cupferron Fe(O2N2C6H5)3". Acta Crystallographica. 18 (3): 355–362. doi:10.1107/S0365110X65000816.
Mark, Wanda; Aava, Ulf; Haaland, A.; Resser, Dag; Rasmussen, S. E.; Sunde, Erling; Sørensen, Nils Andreas (1970). "The Crystal Structure of Zirconium Cupferrate, Zr(C6H5N2O2)4". Acta Chemica Scandinavica. 24: 1398–1414. doi:10.3891/acta.chem.scand.24-1398.

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[1] C. S. Marvel (1925). "Cupferron". Organic Syntheses. 4: 19. doi:10.15227/orgsyn.004.0019.

[2] Elerman, Y.; Atakol, O.; Svoboda, I.; Geselle, M. (1995). "Bis(cupferronato)copper(II), [Cu(C6H5N2O2)2]". Acta Crystallographica Section C Crystal Structure Communications. 51 (8): 1520–1522. doi:10.1107/S0108270195002770.

[3] Van Der Helm, D.; Merritt, L. L.; Degeilh, R.; MacGillavry, C. H. (1965). "The crystal structure of iron cupferron Fe(O2N2C6H5)3". Acta Crystallographica. 18 (3): 355–362. doi:10.1107/S0365110X65000816.

[4] Mark, Wanda; Aava, Ulf; Haaland, A.; Resser, Dag; Rasmussen, S. E.; Sunde, Erling; Sørensen, Nils Andreas (1970). "The Crystal Structure of Zirconium Cupferrate, Zr(C6H5N2O2)4". Acta Chemica Scandinavica. 24: 1398–1414. doi:10.3891/acta.chem.scand.24-1398.