UNIGE document Scientific Article
previous document  unige:28405  next document
add to browser collection
Title

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

Authors
Adriaenssens, Louis
Estarellas, Carolina
Martinez Belmonte, Marta
Ballester, Pablo
Published in Journal of the American Chemical Society. 2013, vol. 135, no. 22, p. 8324-8330
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.
Identifiers
Full text
Article (Published version) (2.6 MB) - document accessible for UNIGE members only Limited access to UNIGE
Article (Accepted version) (1.3 MB) - public document Free access
Structures
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 https://archive-ouverte.unige.ch/unige:28405

435 hits

176 downloads

Update

Deposited on : 2013-06-05

Export document
Format :
Citation style :