Quantification of nitrate−π interactions and selective transport of nitrate using calix4pyrroles with two aromatic walls

Adriaenssens, L. and Estarellas, C. and Vargas Jentzsch, A. and Martinez Belmonte, M. and Matile, S. and Ballester, P. (2013) Quantification of nitrate−π interactions and selective transport of nitrate using calix4pyrroles with two aromatic walls. Journal of the American Chemical Society, 135 (22). pp. 8324-8330. ISSN 0002-7863

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Abstract

Herein we disclose the results of our investigations regarding the interactions between the biologically relevant nitrate oxoanion and several "two-wall" aryl-extended calix4pyrroles. There exists a clear relationship between the electronic nature of the aromatic walls of the calix4pyrroles and the stability of the nitrateâŠcalix4pyrrole complex. This suggests that NO3--� 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 calix4pyrroles. Finally, the "two-wall" aryl-extended calix4pyrroles 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. © 2013 American Chemical Society.

Keywords:Binding geometries, Calix4pyrrole, Electronic natures, Electrostatic components, Ion transports, Nitrate anions, Selective transport, Aromatic compounds, Negative ions, Potassium compounds, Nitrates, anion, calix4pyrrole derivative, nitrate, phenyl group, pyrrole derivative, unclassified drug, article, chemical bond, chemical interaction, chemical structure, geometry, ion transport, lipid membrane, static electricity, Calixarenes, Hydrocarbons, Aromatic, Models, Molecular, Molecular Structure, Nitrates, Porphyrins, Thermodynamics
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
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ID Code:22735
Deposited On:30 Jul 2016 21:52

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