University of Surrey

Test tubes in the lab Research in the ATI Dance Research

An Asymmetric N-Rim Partially Substituted Calix[4]pyrrole: Its Affinity for Ag(I) and its Destruction by Hg(II)

Chaaban, Jinane, Hakawati, Nawal Al, Howlin, Brendan, Bance-Soualhi, Rachida and Danil de Namor, Angela (2020) An Asymmetric N-Rim Partially Substituted Calix[4]pyrrole: Its Affinity for Ag(I) and its Destruction by Hg(II) Arabian Journal of Chemistry.

[img] Text
Manuscript Arabian Journal of Chemistry.docx - Accepted version Manuscript

Download (71kB)
Arabian Journal of Chemistry.pdf - Version of Record
Available under License Creative Commons Attribution Non-commercial No Derivatives.

Download (2MB) | Preview


A new partially substituted calix[4] pyrrole derivative obtained by the introduction of three thioamide functionalities in the N-rim has been synthesised and fully characterised by 1H,13C, HSQC, ROESY NMR and mass spectroscopy. Computer modelling suggested an alternate conformation which was confirmed through ROESY 1H NMR. The receptor interacts only with the silver cation as shown by 1H NMR. The strength of interaction is quantitatively assessed by titration calorimetry. N-rim modification eliminates the possibility of interaction with anions. Unlike calix[4] pyrrole derivatives obtained by the introduction of functionalities through the meso-position, addition of Hg(NO3)2 leads to the degeneration of the receptor as demonstrated by 1H NMR, FTIR and XPS analyses. This is for the first time reported. Molecular simulation studies show significant strain in the mercury bound ligand in bonds, angles, torsions leading to the destruction of the receptor. Given the negative environmental impact produced by the availability of silver ions in aquatic organisms, the fundamental studies indicate that this receptor offers potential applications for monitoring silver (ion selective electrode) or indeed as a decontaminating material for removing silver ions from water.

Item Type: Article
Divisions : Faculty of Engineering and Physical Sciences > Chemistry
Authors :
Chaaban, Jinane
Hakawati, Nawal Al
Danil de Namor,
Date : 22 January 2020
Funders : Leverhulme Trust
DOI : 10.1016/j.arabjc.2019.12.015
Copyright Disclaimer : © 2020 The Author(s). Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (
Uncontrolled Keywords : Supramolecular Chemistry; Asymmetric calix[4] pyrrole; Selectivity; Silver Complexation; thermodynamics.
Depositing User : James Marshall
Date Deposited : 30 Jan 2020 09:37
Last Modified : 02 Mar 2020 13:03

Actions (login required)

View Item View Item


Downloads per month over past year

Information about this web site

© The University of Surrey, Guildford, Surrey, GU2 7XH, United Kingdom.
+44 (0)1483 300800