page_title: 8-Hydroxyquinoline
hierarchical_section_title: 8-Hydroxyquinoline
caption_attribution_description: Thermal ellipsoid model of the mer isomer of the tris(8-hydroxyquinolinato)aluminium complex, [Al(C9H6NO)3], as found in the crystal structure. Colour code: Aluminium, Al: pink-brown Carbon, C: black Hydrogen, H: white Nitrogen, N: blue Oxygen, O: red Crystal structure data from J. Am. Chem. Soc. (2000) 122, 5147-5157. Image generated in CrystalMaker 8.3.
context_page_description: 8-Hydroxyquinoline is a chelating agent which has been used for the quantitative determination of metal ions.
  In aqueous solution 8-hydroxyquinoline has a pKₐ value of ca. 9.9 It reacts with metal ions, losing the proton and forming 8-hydroxyquinolinato-chelate complexes.
  The aluminium complex is a common component of organic light-emitting diodes. Variations in the substituents on the quinoline rings affect its luminescence properties.
  In the photochemically induced excited-state zwitterionic isomers are formed in which the hydrogen atom is transferred from oxygen to nitrogen.
  The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties, functioning as a transcription inhibitor. Its solution in alcohol is used in liquid bandages. It once was of interest as an anti-cancer drug.
  A thiol analogue, 8-mercaptoquinoline is also known.
  The roots of the invasive plant Centaurea diffusa release 8-hydroxyquinoline, which has a negative effect on plants that have not co-evolved with it.
context_section_description: 8-Hydroxyquinoline (also known as oxine) is a chelating agent which has been used for the quantitative determination of metal ions.
  In aqueous solution 8-hydroxyquinoline has a pKₐ value of ca. 9.9 It reacts with metal ions, losing the proton and forming 8-hydroxyquinolinato-chelate complexes. 
  The aluminium complex is a common component of organic light-emitting diodes (OLEDs).  Variations in the substituents on the quinoline rings affect its luminescence properties.
  In the photochemically induced excited-state zwitterionic isomers are formed in which the hydrogen atom is transferred from oxygen to nitrogen.
  The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties, functioning as a transcription inhibitor. Its solution in alcohol is used in liquid bandages. It once was of interest as an anti-cancer drug.
  A thiol analogue, 8-mercaptoquinoline is also known.   
  The roots of the invasive plant Centaurea diffusa release 8-hydroxyquinoline, which has a negative effect on plants that have not co-evolved with it.
caption: Tris(8-hydroxyquinolinato)aluminium[11]
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