Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Syntheses of 3-(Carboxyalkyl)salicylaldehyde Derivatives and Their Copper Chelates
Tsuguo Tanaka
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1972 Volume 45 Issue 7 Pages 2113-2120


In order to study the influence of the side-chain carboxylic acid groups on the formation of the metal chelates, 5-bromo-3-carboxymethyl-, 5-methyl-3-β-carboxyethyl-, and 5-chloro-3-β-carboxyethyl-salicylaldehyde (2a, b c) were synthesized. The green binuclear copper chelates of these aldehydes, di-μ-aquo-bis-(5-bromo-3-carboxymethylsalicylaldehyde)-, di-μ-aquo-bis-(5-methyl-3-β-carboxyethylsalicylaldehyde)-, and di-μ-aquo-bis-(5-chloro-3-β-carboxyethylsalicylaldehyde)-dicopper (11a, b, c) yielded the green binuclear bis-ethylenediimine chelates (12a, b, c), while bis-(5-bromo-3-carboxymethylsalicylaldehyde)-, bis-(5-methyl-3-β-carboxyethylsalicylaldehyde)-, and bis-(5-chloro-3-β-carboxyethylsalicylaldehyde)-ethylenediimine (14a, b, c) gave a brown (13a) and gray-purple (13b, c) mononuclear copper chelates. The reduction of 14a, b, c with sodium borohydride yielded the ihexadentate ligands N,N′-bis-(5-bromo-2-hydroxy-3-carboxymethylbenzyl)-, N,N′,-bis-(5-methyl-2-hydroxy-3-β-carboxyethylbenzyl)-, and N,N′-bis-(5-chloro-2-hydroxy-3-β-carboxyethylbenzyl)-ethylenediamine (15a, b, c), which proved useful for the spectrophotometric determination of the copper (II) ion from solutions containing copper (II) and nickel (II) ions, and the iron (II) ion from solutions containing iron (II) and nickel (II) ions.

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