SYNTHESIS, X-RAY STRUCTURE AND ALKALI-METAL BINDING-PROPERTIES OF A NEW HEXAHOMOTRIAZACALIX[3]ARENE

Hexahomotriazacalix[3] arene dagger 1 has been synthesized by the reac tion of 2,6-bis(chloromethyl)-4-methylphenol 6 with glycine methyl est er hydrochloride under high-dilution conditions, The crystal structure of 1 indicates that the macrocycle adopts a cone shape in the solid s tate with all three ester groups on the same side and within the cone of the macrocycle. In contrast with the calixarenes, macrocycle 1 exhi bits only a modest degree of cupping, H-1 NMR spectra indicate that th e cone and partial cone isomers of 1 are rapidly interconverting in th e NMR timescale at room temperature, Macrocycle 1 exhibits no signific ant extraction of alkali metal picrates from aqueous solution.