{{chembox | Watchedfields = changed | verifiedrevid = 420653113 | Name = Cupferron | ImageFile = cupferron.svg | ImageName = Cupferron | OtherNames = cupferron<br /> 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<sup>−</sup>. 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 NH<sub>4</sub>[C<sub>6</sub>H<sub>5</sub>N(O)NO]. The anion binds to metal cations through the two oxygen atoms, forming five-membered chelate rings.
==Synthesis and complexes== [[File:Fe(CU)3.svg|thumb|left|120px|Structure of ferric cupferron complex]] Cupferron is prepared from phenylhydroxylamine and an NO<sup>+</sup> source:<ref>{{cite journal|doi=10.15227/orgsyn.004.0019|title=Cupferron|journal=Organic Syntheses|year=1925|volume=4|pages=19|author=C. S. Marvel}}</ref> ::C<sub>6</sub>H<sub>5</sub>NHOH + C<sub>4</sub>H<sub>9</sub>ONO + NH<sub>3</sub> → NH<sub>4</sub>[C<sub>6</sub>H<sub>5</sub>N(O)NO] + C<sub>4</sub>H<sub>9</sub>OH
Being a bidentate mono-anionic ligand, CU<sup>−</sup> forms complexes analogous to those produced with acetylacetonate. Illustrative complexes include Cu(CU)<sub>2</sub>, Fe(CU)<sub>3</sub>, and Zr(CU)<sub>4</sub>.<ref>{{cite journal|doi=10.1107/S0108270195002770|title=Bis(cupferronato)copper(II), [Cu(C<sub>6</sub>H<sub>5</sub>N<sub>2</sub>O<sub>2</sub>)<sub>2</sub>]|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}}</ref><ref>{{cite journal|doi=10.1107/S0365110X65000816|title=The Crystal Structure of IIron Cupferron Fe(O<sub>2</sub>N<sub>2</sub>C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>|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}}</ref><ref>{{cite journal|doi=10.3891/acta.chem.scand.24-1398|title=The Crystal Structure of Zirconium Cupferrate, Zr(C<sub>6</sub>H<sub>5</sub>N<sub>2</sub>O<sub>2</sub>)<sub>4</sub>|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}}</ref>
== See also == * Nitroso ** ''N''-nitroso * Phenyl ** Phenylamine (aniline)
==References== <references /> {{aromatic-stub}} {{Ammonium salts}}
Category:Phenyl compounds Category:Ammonium compounds Category:Nitroso compounds