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Quantification of Nitrate−π Interactions and Selective Transport of Nitrate Using Calix[4]pyrroles with Two Aromatic Walls

Published inJournal of the American Chemical Society, vol. 135, no. 22, p. 8324-8330
Publication date2013
Abstract

Herein we disclose the results of our investigations regarding the interactions between the biologically relevant nitrate oxoanion and several “two-wall” aryl-extended calix[4]pyrroles. There exists a clear relationship between the electronic nature of the aromatic walls of the calix[4]pyrroles and the stability of the nitratecalix[4]pyrrole complex. This suggests that NO3––π interactions have an important electrostatic component. We provide energetic estimates for the interaction of nitrate with several phenyl derivatives. Additionally, we report solid-state evidence for a preferred binding geometry of the nitrate anion included in the calix[4]pyrroles. Finally, the “two-wall” aryl-extended calix[4]pyrroles show excellent activity in ion transport through lipid-based lamellar membranes. Notably the best anion transporters are highly selective for transport of nitrate over other anions.

Citation (ISO format)
ADRIAENSSENS, Louis et al. Quantification of Nitrate−π Interactions and Selective Transport of Nitrate Using Calix[4]pyrroles with Two Aromatic Walls. In: Journal of the American Chemical Society, 2013, vol. 135, n° 22, p. 8324–8330. doi: 10.1021/ja4021793
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ISSN of the journal0002-7863
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Technical informations

Creation06/05/2013 9:20:00 AM
First validation06/05/2013 9:20:00 AM
Update time03/14/2023 8:17:54 PM
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