1-Nitroso-2-naphthol explained

1-Nitroso-2-naphthol is an organic compound with the formula . It is one of several possible nitrosonaphthols, and the most studied for applications as an indicator and a dye.^[1]

Synthesis and reactions

1-Nitroso-2-naphthol can be prepared by treatment of 2-naphthol with nitrous acid:^[2]

Its conjugate base forms deeply colored complexes with iron(II) and cobalt(II), complexes [M(C₁₀H₆(NO)O)₃]^2-.^[3] The deep colors of these complexes results from the delocalized bonding within each five-membered chelate ring. These species can be classified as nitroso complexes.

See also

• Naphthol Green B, the iron complex of a sulfonated derivative of 1-nitroso-2-naphthol

References

1. 10.1016/0304-4203(94)90012-4 . Determination of complexation of iron(III) with natural organic complexing ligands in seawater using cathodic stripping voltammetry . 1994 . Gledhill . Martha . Van Den Berg . Constant M.G. . Marine Chemistry . 47 . 1 . 41–54 . 1994MarCh..47...41G .
2. 10.15227/orgsyn.002.0061. Organic Syntheses . 1922 . 2 . 61 . Nitroso-β-Naphthol . C. S.. Marvel. P. K.. Porter.
3. 10.1002/aoc.3178 . Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H₂O₂ . 2014 . Wang . Xiao . Zhang . Tianyong . Li . Bin . Yang . Qiusheng . Jiang . Shuang . Applied Organometallic Chemistry . 28 . 9 . 666–672 .