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

File:Fe(CU)3.svg

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