Chemical compound
1-Nitroso-2-naphthol is an organic compound with the formula C10H6(NO)OH. It is one of several possible nitrosonaphthols, and the most studied for applications as an indicator and a dye.[2]
Synthesis and reactions
1-Nitroso-2-naphthol can be prepared by treatment of 2-naphthol with nitrous acid:[3]
- C10H7OH + HNO2 → C10H6(NO)OH + H2O
Its conjugate base forms deeply colored complexes with iron(II) and cobalt(II), complexes [M(C10H6(NO)O)3]2-.[4] 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-Nitroso-2-naphthol". pubchem.ncbi.nlm.nih.gov.
- ^ Gledhill, Martha; Van Den Berg, Constant M.G. (1994). "Determination of complexation of iron(III) with natural organic complexing ligands in seawater using cathodic stripping voltammetry". Marine Chemistry. 47 (1): 41–54. Bibcode:1994MarCh..47...41G. doi:10.1016/0304-4203(94)90012-4.
- ^ Marvel, C. S.; Porter, P. K. (1922). "Nitroso-β-Naphthol". Organic Syntheses. 2: 61. doi:10.15227/orgsyn.002.0061.
- ^ Wang, Xiao; Zhang, Tianyong; Li, Bin; Yang, Qiusheng; Jiang, Shuang (2014). "Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H2O2". Applied Organometallic Chemistry. 28 (9): 666–672. doi:10.1002/aoc.3178.
