cupferron
{{chembox
| Watchedfields = changed
| verifiedrevid = 420653113
| Name = Cupferron
| ImageFile = cupferron.svg
| ImageName = Cupferron
| OtherNames = cupferron
ammonium N-nitrosophenylhydroxylamine
|Section1={{Chembox Identifiers
| SMILES = O=NN([O-])c1ccccc1.[NH4+]
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2006262
| PubChem = 2724103
| EC_number = 205-183-2
| InChI = 1/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1
| InChIKey = GDEBSAWXIHEMNF-IKLDFBCSAP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GDEBSAWXIHEMNF-UHFFFAOYSA-O
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 135-20-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V66QK963ED
}}
|Section2={{Chembox Properties
| C=6 | H=9 | N=3 | O=2
| Solubility = Soluble
| MeltingPtC = 150 to 155
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|315|319|335|351 }}
| PPhrases = {{P-phrases|201|202|261|264|270|271|280|281|301+310|302+352|304+340|305+351+338|308+313|312|321|330|332+313|337+313|362|403+233|405|501}}
}}
}}
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[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:{{cite journal|doi=10.15227/orgsyn.004.0019|title=Cupferron|journal=Organic Syntheses|year=1925|volume=4|pages=19|author=C. S. Marvel}}
::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.{{cite journal|doi=10.1107/S0108270195002770|title=Bis(cupferronato)copper(II), [Cu(C6H5N2O2)2]|year=1995|last1=Elerman|first1=Y.|last2=Atakol|first2=O.|last3=Svoboda|first3=I.|last4=Geselle|first4=M.|journal=Acta Crystallographica Section C Crystal Structure Communications|volume=51|issue=8|pages=1520–1522}}{{cite journal|doi=10.1107/S0365110X65000816|title=The Crystal Structure of IIron Cupferron Fe(O2N2C6H5)3|year=1965|last1=Van Der Helm|first1=D.|last2=Merritt|first2=L. L.|last3=Degeilh|first3=R.|last4=MacGillavry|first4=C. H.|journal=Acta Crystallographica|volume=18|issue=3|pages=355–362|doi-access=free}}{{cite journal|doi=10.3891/acta.chem.scand.24-1398|title=The Crystal Structure of Zirconium Cupferrate, Zr(C6H5N2O2)4|year=1970|last1=Mark|first1=Wanda|last2=Aava|first2=Ulf|last3=Haaland|first3=A.|last4=Resser|first4=Dag|last5=Rasmussen|first5=S. E.|last6=Sunde|first6=Erling|last7=Sørensen|first7=Nils Andreas|journal=Acta Chemica Scandinavica|volume=24|pages=1398–1414|doi-access=free}}
References
{{aromatic-stub}}
{{Ammonium salts}}