ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Mono-N-substituted azamacrocycles 2-7, containing a carboxyalkyl or carboxyaryl side-chain, are obtained by reacting a five-fold excess of the macrocycle with 1 equiv. of a suitable halogenocarboxylic acid in alkaline aqueous EtOH. For halogenocarboxylic acids, which easily lactonize under alkaline conditions, a variant with the corresponding ester or nitrile as alkylating agent is also described. The salient point of this synthesis lies in the use of an excess of the macrocycle over the alkylating agent, thus reducing the amount of polyalkylation to a minimum, and in the easy separation of the excess of unreacted educt from the aminocarboxylic acid. These new ligands form Ni2+ and Cu2+ complexes, the spectral properties of which have been studied. In the case of the Cu2+ complexes with ligand 2, 3, and 6, a pH-dependent color change is observed. This is explained with an equilibrium between a species, in which the carboxylate group is bound to the metal, and one, in which it is protonated and non-coordinated. In the case of the Ni2+ complexes with the same ligands, only the species with a coordinated carboxylate was observed. In the Cu2+ and Ni2+ complexes with ligands 4 and 5, however, the carboxylate group does not coordinate at all, because of the length or the special structure of the chain.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19860690832
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