title: Quantification of nitrate-π interactions and selective transport of nitrate using calix[4]pyrroles with two aromatic walls.
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 nitrate⊂calix[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.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ) , Avda. Països Catalans 16, 43007 Tarragona, Spain.
authors.forename: Louis
authors.initials: L
authors.lastname: Adriaenssens
authors.forename: Carolina
authors.initials: C
authors.lastname: Estarellas
authors.forename: Andreas
authors.initials: A
authors.lastname: Vargas Jentzsch
authors.forename: Marta
authors.initials: M
authors.lastname: Martinez Belmonte
authors.forename: Stefan
authors.initials: S
authors.lastname: Matile
authors.forename: Pablo
authors.initials: P
authors.lastname: Ballester
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009566:Nitrates / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry*; D013816:Thermodynamics
chemical_list: D006841:Hydrocarbons, Aromatic; D009566:Nitrates; D011166:Porphyrins; C469811:calix(4)pyrrole; D047250:Calixarenes