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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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dc.contributor.authorNavarro García, Encarnación
dc.contributor.authorVelasco, María D.
dc.contributor.authorZapata Fernández, Fabiola
dc.contributor.authorBauzá, Antonio
dc.contributor.authorFrontera, Antonio
dc.contributor.authorRamírez de Arellano, Carmen
dc.contributor.authorCaballero, Antonio
dc.contributor.departmentQuímica Orgánica
dc.date.accessioned2024-02-07T08:49:44Z
dc.date.available2024-02-07T08:49:44Z
dc.date.issued2019-08-21
dc.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
dc.description.abstractWe 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.es
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dc.format.extent9es
dc.identifier.citationDalton Transactions, 48, 2019: 11813–11821
dc.identifier.doihttps://doi.org/10.1039/c9dt02012h
dc.identifier.issnPrint: 1477-9226
dc.identifier.issnElectronic: 1477-9234
dc.identifier.urihttp://hdl.handle.net/10201/138809
dc.languageenges
dc.publisherRoyal Society of Chemistryes
dc.relationMinisterio de Economía y Competitividad of Spain and the FEDER (projects CTQ2013- 46096-P, CTQ2017-85821-R and CTQ2017-86775-P) Fundación Séneca Región de Murcia (CARM) (projects 18948/ JLI/13 and 20819/PI/18)es
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.rightsAttribution-NoCommercial-NoDerivatives 4.0 Internacional
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectAnion bindinges
dc.subjectHalogen bonding
dc.subjectHydrogen bonding
dc.subject.otherCDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánicaes
dc.titleExploiting 1,4-naphthoquinone and 3-iodo-1,4- naphthoquinone motifs as anion binding sites by hydrogen or halogen-bonding interactionses
dc.typeinfo:eu-repo/semantics/articlees
dspace.entity.typePublicationes
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