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Reconciling Experiment and Theory in the Use of Aryl-Extended Calix[4]pyrrole Receptors for the Experimental Quantification of Chloride<br>π Interactions in Solution

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dc.contributor.author Bauzá Riera, Antonio
dc.contributor.author Quiñonero, David
dc.contributor.author Frontera Beccaria, Antonio
dc.contributor.author Ballester Balaguer, Pablo José
dc.date.accessioned 2015-09-18T10:17:07Z
dc.date.available 2015-09-18T10:17:07Z
dc.date.issued 2015
dc.identifier.citation 1661-6596
dc.identifier.uri http://hdl.handle.net/11201/1257
dc.description.abstract In this manuscript we consider from a theoretical point of view the recently reported experimental quantification of anion<br>π interactions (the attractive force between electron deficient aromatic rings and anions) in solution using aryl extended calix[4]pyrrole receptors as model systems. Experimentally, two series of calix[4]pyrrole receptors functionalized, respectively, with two and four aryl rings at the meso positions, were used to assess the strength of chloride<br>π interactions in acetonitrile solution. As a result of these studies the contribution of each individual chloride<br>π interaction was quantified to be very small (<1 kcal/mol). This result is in contrast with the values derived from most theoretical calculations. Herein we report a theoretical study using high-level density functional theory (DFT) calculations that provides a plausible explanation for the observed disagreement between theory and experiment. The study reveals the existence of molecular interactions between solvent molecules and the aromatic walls of the receptors that strongly modulate the chloride<br>π interaction. In addition, the obtained theoretical results also suggest that the chloride-calix[4]pyrrole complex used as reference to dissect experimentally the contribution of the chloride<br>π interactions to the total binding energy for both the two and four-wall aryl-extended calix[4]pyrrole model systems is probably not ideal.
dc.language.iso eng
dc.publisher MDPI AG, Basel, Switzerland
dc.relation.isformatof Reproducció del document publicat a: 10.3390/ijms16048934
dc.relation.ispartof International Journal Of Molecular Sciences, 2015, vol. 16, p. 8934-8948
dc.rights cc-by (c) Bauzá, Antonio et al., 2015
dc.rights.uri http://creativecommons.org/licenses/by/3.0/es
dc.title Reconciling Experiment and Theory in the Use of Aryl-Extended Calix[4]pyrrole Receptors for the Experimental Quantification of Chloride<br>π Interactions in Solution
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/publishedVersion
dc.date.updated 2015-09-18T10:17:08Z
dc.rights.accessRights info:eu-repo/semantics/openAccess


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cc-by (c) Bauzá, Antonio et al., 2015 Except where otherwise noted, this item's license is described as cc-by (c) Bauzá, Antonio et al., 2015

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