Tetrakis(methylimidazole) and tetrakis(methylimidazolium) calix[4]arenes: Competitive anion binding and deprotonation

Emma K. Bullough; Colin A. Kilner; Marc A. Little; Charlotte E. Willans

doi:10.1039/c2ob07025a

Tetrakis(methylimidazole) and tetrakis(methylimidazolium) calix[4]arenes: Competitive anion binding and deprotonation

Emma K. Bullough, Colin A. Kilner, Marc A. Little, Charlotte E. Willans^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2824-2829
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	14
DOIs	https://doi.org/10.1039/c2ob07025a
Publication status	Published - 7 Apr 2012

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Bullough, Emma K.

AU - Kilner, Colin A.

AU - Little, Marc A.

AU - Willans, Charlotte E.

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AB - 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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Tetrakis(methylimidazole) and tetrakis(methylimidazolium) calix[4]arenes: Competitive anion binding and deprotonation

Abstract

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