Mass spectrometry of 8-hydroxyquinoline derivatives

Autor: Ermakov, A. I., Voronin, V. G., Sorokin, A. A., Épshtein, N. I., Muravskaya, I. D., Chistyakov, V. V., Zuev, A. P.
Zdroj: Chemistry of Heterocyclic Compounds; June 1984, Vol. 20 Issue: 6 p637-642, 6p
Abstrakt: In contrast to the fragmentation of the corresponding alkyl aryl ethers, characteristic [M-H]+ and [M-H, -CO]+ fragments were observed in the fragmentation of 5-nitro(halo)-substituted 8-alkoxyquinolines. It was found by means of deuterium labeling that a hydrogen atom is split out primarily from the alkoxy group. It was demonstrated that an [M-H, -CO]+ fragment was formed from the [M-H]+ ion, which has a three-ring structure and a quaternary nitrogen atom. The formation of an [M-CO]+ fragment is characteristic for the fragmentation of 5(7)-nitro(halo)-substituted 8-hydroxyquinolines. The interrelationship between the intensities of the [M-H]+, [M-H, -CO]+, and [M-CO]+ ion peaks and the protonation constants (pKa) of the investigated compounds is discussed.
Databáze: Supplemental Index