Английская Википедия:8-Hydroxyquinoline

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8-Hydroxyquinoline (also known as oxine) is an organic compound derived from the heterocycle quinoline. A colorless solid, its conjugate base is a chelating agent, which is used for the quantitative determination of metal ions.

In aqueous solution 8-hydroxyquinoline has a pKa value of ca. 9.9[1] It reacts with metal ions, losing the proton and forming 8-hydroxyquinolinato-chelate complexes.

Файл:Mer-tris(8-hydroxyquinoline)aluminium(III)-from-xtal-2000-CM-3D-ellipsoids.png
Tris(8-hydroxyquinolinato)aluminium[2]

The aluminium complex,[3] is a common component of organic light-emitting diodes (OLEDs). Substituents on the quinoline ring affect the luminescence properties.[4]

In its photo-induced excited-state, 8-hydroxyquinoline converts to zwitterionic isomers, in which the hydrogen atom is transferred from oxygen to nitrogen.[5]

Bioactivity

The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties,[6][7] functioning as a transcription inhibitor.[8] Its solution in alcohol is used in liquid bandages. It once was of interest as an anti-cancer drug.[9]

A thiol analogue, 8-mercaptoquinoline is also known.[10]

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.[11]

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See also

References

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Шаблон:Antiseptics and disinfectants Шаблон:Gynecological anti-infectives and antiseptics Шаблон:Antiprotozoal agent