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Cupferron

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Cupferron
Cupferron
Names
Other names cupferron
ammonium N-nitrosophenylhydroxylamine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.713 Edit this at Wikidata
EC Number
  • 205-183-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1Key: GDEBSAWXIHEMNF-UHFFFAOYSA-O
  • InChI=1/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1Key: GDEBSAWXIHEMNF-IKLDFBCSAP
SMILES
  • O=NN()c1ccccc1.
Properties
Chemical formula C6H9N3O2
Molar mass 155.157 g·mol
Melting point 150 to 155 °C (302 to 311 °F; 423 to 428 K)
Solubility in water Soluble
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H301, H315, H319, H335, H351
Precautionary statements P201, P202, P261, P264, P270, P271, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Cupferron is jargon for the ammonium salt of the conjugate base derived from N-nitroso-N-phenylhydroxylamine. This conjugate base is abbreviated as CU. 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. The anion binds to metal cations through the two oxygen atoms, forming five-membered chelate rings.

Synthesis and complexes

Structure of ferric cupferron complex

Cupferron is prepared from phenylhydroxylamine and an NO source:

C6H5NHOH + C4H9ONO + NH3 → NH4 + 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.

References

  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 IIron 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.
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Ammonium salts
Inorganic salts
monatomic anions
oxyanions
other anions
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