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
EC Number	205-183-2;
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
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H315, H319, H335, H351
GHS precautionary statements	P201, P202, P261, P264, P270, P271, P280, P281, P301+310, P302+352, P304+340, P305+351+338, P308+313, P312, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501
	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]

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.