Abstract
AbstractThe Mannich aminomethylation reaction of aromatic thiols has been used to produce diaza‐18‐crown‐6 ligands containing thiol‐derived side arms. Thiophenols were attached to the azacrown through N‐CH2‐S linkages even in the presence of hydroxy or acetamido groups. Heteroaromatic thiols containing N=C‐SH (or NH‐C=S) structural fragments were attached to diaza‐18‐crown‐6 by N‐CH2‐N linkages with the thiol becoming a thione function. X‐ray crystal structural analyses show the N‐CH2‐S and N‐CH2‐N linkages for some of the new macrocyclic compounds. Interactions of four of the new diaza‐18‐crown‐6 ligands with Na+, K+, Ba2+, Ag+, Zn2+, Cd2+, Ni2+, and Cu2+ were evaluated by calorimetric titration at 25° in methanol. The results show that these ligands form stable complexes with many of the metal ions studied.
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