Neutral tetrakis(methylimidazole) (1) and the novel cationic tetrakis(methylimidazolium) (2) calixarenes have been prepared and their solid-state and solution behaviour examined. The neutral imidazole forms a mono-zwitterion at elevated temperature, a feature that has been observed both in solution and in the solid-state. The cationic imidazolium exhibits a range of hydrogen bond interactions with anions, with the titration curves upon binding to basic anions suggesting sequential binding to both the upper and lower rims.
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Bullough et al. (2012) studied this question.
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