Cupferron

In this article, we will explore the fascinating world of Cupferron. From its origins to its impact today, Cupferron has been the subject of study, debate and admiration by experts and enthusiasts. Throughout history, Cupferron has played a crucial role in various fields, from science and technology to art and culture. We will learn about its different facets, analyze its influence on society and reflect on its relevance in the current context. Get ready to embark on an exciting journey through Cupferron and discover everything this theme has to offer.

Cupferron
Cupferron
Cupferron
Names
Other names
cupferron
ammonium N-nitrosophenylhydroxylamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.713 Edit this at Wikidata
EC Number
  • 205-183-2
UNII
  • InChI=1S/C6H5N2O2.H3N/c9-7-8(10)6-4-2-1-3-5-6;/h1-5H;1H3/q-1;/p+1 checkY
    Key: GDEBSAWXIHEMNF-UHFFFAOYSA-O checkY
  • 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
  • O=NN()c1ccccc1.
Properties
C6H9N3O2
Molar mass 155.157 g·mol−1
Melting point 150 to 155 °C (302 to 311 °F; 423 to 428 K)
Soluble
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H315, H319, H335, H351
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 checkY☒N ?)

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:[1]

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.[2][3][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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