Synthesis and complexing properties of four imidazolyl acetamido p-tert-butylcalix[4]arenes

Four imidazolyl acetamido p-tert-butylcalix[4]arenes 5–8 have been prepared by reacting the corresponding methyl esters derivatives 1–4 with histamine in 1:1 mixture of methanol:toluene. The yields ranged from 56 to 68%. 5–8 have been shown to be in cone conformation. The complexation behaviour of 5–8 towards monovalent metal picrates M+Pic− with M+ = Li+, Na+, K+, Rb+ and Cs+ and divalent metal picrates M2+(Pic−)2 with M2+ = Mg2+, Ca2+, Sr2+, Ba2+, Pb2+, Cd2+, Zn2+ and Co2+ are given. Tentative localisation of the metal cations in the receptors is given. The binding properties towards these cations have been determined along with stoichiometries of the complexes.