An asymmetric N-rim partially substituted calix[4]pyrrole: Its affinity for Ag(I) and its destruction by Hg(II)
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 confir...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2020-03-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535220300022 |
| _version_ | 1818498867308527616 |
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| author | Jinane K. Chaaban Nawal Al Hakawati Brendan Howlin Rachida Bance-Soualhi Angela F. Danil de Namor |
| author_facet | Jinane K. Chaaban Nawal Al Hakawati Brendan Howlin Rachida Bance-Soualhi Angela F. Danil de Namor |
| author_sort | Jinane K. Chaaban |
| collection | DOAJ |
| description | 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. Keywords: Supramolecular chemistry, Asymmetric calix[4] pyrrole, Selectivity, Silver complexation, Thermodynamics |
| first_indexed | 2024-12-10T20:21:26Z |
| format | Article |
| id | doaj.art-95235a11f9604dafa2b5d823a879947e |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-10T20:21:26Z |
| publishDate | 2020-03-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-95235a11f9604dafa2b5d823a879947e2022-12-22T01:35:02ZengElsevierArabian Journal of Chemistry1878-53522020-03-0113348244834An asymmetric N-rim partially substituted calix[4]pyrrole: Its affinity for Ag(I) and its destruction by Hg(II)Jinane K. Chaaban0Nawal Al Hakawati1Brendan Howlin2Rachida Bance-Soualhi3Angela F. Danil de Namor4Lebanese University, Department Of Chemistry, Faculty of Sciences, Section I, Hadath, LebanonThermochemistry Laboratory. Chemistry Department, University of Surrey, Guildford, Surrey GU2 7XH, UK; Natural Sciences Department, School of Arts and Sciences, Lebanese American University, P.O.Box 13–5053, Chouran Beirut, 1102 2801 Beirut, LebanonThermochemistry Laboratory. Chemistry Department, University of Surrey, Guildford, Surrey GU2 7XH, UKThermochemistry Laboratory. Chemistry Department, University of Surrey, Guildford, Surrey GU2 7XH, UKThermochemistry Laboratory. Chemistry Department, University of Surrey, Guildford, Surrey GU2 7XH, UK; Instituto Nacional de Tecnologia Industrial, Ministry of Production, Argentina; Corresponding author at: Thermochemistry Laboratory, Chemistry Department, University of Surrey, Guildford, Surrey GU2 7XH, UK.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. Keywords: Supramolecular chemistry, Asymmetric calix[4] pyrrole, Selectivity, Silver complexation, Thermodynamicshttp://www.sciencedirect.com/science/article/pii/S1878535220300022 |
| spellingShingle | Jinane K. Chaaban Nawal Al Hakawati Brendan Howlin Rachida Bance-Soualhi Angela F. Danil de Namor An asymmetric N-rim partially substituted calix[4]pyrrole: Its affinity for Ag(I) and its destruction by Hg(II) Arabian Journal of Chemistry |
| title | An asymmetric N-rim partially substituted calix[4]pyrrole: Its affinity for Ag(I) and its destruction by Hg(II) |
| title_full | An asymmetric N-rim partially substituted calix[4]pyrrole: Its affinity for Ag(I) and its destruction by Hg(II) |
| title_fullStr | An asymmetric N-rim partially substituted calix[4]pyrrole: Its affinity for Ag(I) and its destruction by Hg(II) |
| title_full_unstemmed | An asymmetric N-rim partially substituted calix[4]pyrrole: Its affinity for Ag(I) and its destruction by Hg(II) |
| title_short | An asymmetric N-rim partially substituted calix[4]pyrrole: Its affinity for Ag(I) and its destruction by Hg(II) |
| title_sort | asymmetric n rim partially substituted calix 4 pyrrole its affinity for ag i and its destruction by hg ii |
| url | http://www.sciencedirect.com/science/article/pii/S1878535220300022 |
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