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Electronic and ESR spectroscopy was used to show that the reactions of dimethylaminomethylcalix[4]resorcinarene with Cu(II) salicylaldiminates bearing alkyl substituents at the salicylaldiminate nitrogen atom give 1 : 1 adducts with the dimethylamino group coordinated axially to the Cu(II) complex. The spatially organized calix[4]resorcinarene structure and the possibility of outer-sphere interactions favor a much higher stability of the adduct compared with the similar complex with 2-dimethylaminomethylphenol. In going from alkyl to aryl substituents, salicylaldiminates are replaced by the anion derived from dimethylaminomethylcalix[4]resocinarene. The same replacement takes place in the reaction with 2-dimethylaminomethylphenol.