Publication:
Exploiting 1,4-naphthoquinone and 3-iodo-1,4- naphthoquinone motifs as anion binding sites by hydrogen or halogen-bonding interactions

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Dalton Trans 2019 48 11813.pdf(1.46 MB)
Date
2019-08-21
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Authors
Navarro García, Encarnación ; Velasco, María D. ; Zapata Fernández, Fabiola ; Bauzá, Antonio ; Frontera, Antonio ; Ramírez de Arellano, Carmen ; Caballero, Antonio
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Publisher
Royal Society of Chemistry
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Química Orgánica
DOI
https://doi.org/10.1039/c9dt02012h
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info:eu-repo/semantics/article
Description
©2019. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ This document is the Accepted, version of a Published Work that appeared in final form in Dalton Transactions. To access the final edited and published work see https://doi.org/10.1039/c9dt02012h
Abstract
We describe here the utilization of 1,4-naphthoquinone and 3-iodo-1,4-naphthoquinone motifs as new anion binding sites by hydrogen- or halogen-bonding interactions, respectively. These binding sites have been integrated in bidentate ester based receptors. Emission experiments reveal that both receptors selectively recognize sulfate anions, which induced a remarkable increase of a new emission band attributed to the formation of π-stacking interactions between two 1,4-naphthoquinone units. Absorption spectroscopy and mass spectrometry indicate the disruption of the ester group of the 1,4- naphthoquinone based receptor in the presence of HP2O7 3−, H2PO4−, F−, AcO− and C6H5CO2− and in the halogenated receptor with HP2O7 3−, F− and AcO− anions, while the presence of sulfate anions showed the clasical complexation behaviour. The 1H-NMR experiment showed a slow exchange process of the receptors with their sulfate complexes. The binding mode of the receptors with sulfate has been studied by DFT calculations along with the Molecular Electrostatic Potential (MEP) surface computational tool that reveals those parts of the receptors which are more suitable for interacting with anions.
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Anion binding , Halogen bonding , Hydrogen bonding
Citation
Dalton Transactions, 48, 2019: 11813–11821
URI
http://hdl.handle.net/10201/138809
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