Studies on New Derivatives of 8-Quinolinol as Chelating Agents. II. Chelate Formation of Some Aminomethyl Derivatives Derived from 8-Hydroxyquinoline-2-carbaldehyde with Metal Ions

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The reactions of new oxine derivatives with additional coordinative sites, 8-hydroxyquinoline-2-carbaldehyde, 2-(p-chlorophenylaminomethyl)-, 2-(naphthylaminomethyl)-, 2-(p-tolylaminomethyl)-, and 2-(o-hydroxyphenylaminomethyl)-8-hydroxyquinoline, and N,N′-bis(8-hydroxy-2-quinolylmethyl)ethylenedianiine (abbreviated as HQA, CAMHQ, NAMHQ, TAMHQ, PAMHQ, and BHQED respectively), with Cu2+, Co2+, Ni2+, Zn2+, Cd2+, Mn2+, Mg2+, and Ca2+ were investigated by potentiometric and spectrophotometric methods. The stability constants of the metal chelates were determined in a 50 v/v % aqueous dioxane solution at 25°C. The stability constants of metal chelates of HQA, NAMHQ, CAMHQ, and TAMHQ with a ligand-to-metal ratio of 2:1 are lower than those of oxine. In these ligands, steric hindrance due to the aminomethyl group results in lower stability constants of the metal chelates. PAMHQ reacts as a terdentate ligand with Cu2+, Mn2+, Mg2+, and Ca2+to form 1:1 chelates by coordination with quinoline nitrogen and two phenolate oxygens. BHQED reacts with Cu2+, Co2+, Ni2+, Cd2+, and Mn2+ to form a protonated chelate, MHL+, in the acid region, while, in the neutral region, one proton is released from the protonated chelate to form a deprotonated chelate, ML, by coordination with six donor groups, namely, two imino and hydroxyl groups, and two quinoline nitrogens. BHQED acts as a sexadentate ligand to form the most stable chelates among these oxine derivatives.
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Studies on New Derivatives of 8-Quinolinol as Chelating Agents. II. Chelate Formation of Some Aminomethyl Derivatives Derived from 8-Hydroxyquinoline-2-carbaldehyde with Metal Ions

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