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dc.contributor.author
Petelski, Andre Nicolai
dc.contributor.author
Marquez, Josefina
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Pamies, Silvana Carina
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Sosa, Gladis Laura
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Peruchena, Nelida Maria
dc.date.available
2022-01-20T15:40:16Z
dc.date.issued
2021-02
dc.identifier.citation
Petelski, Andre Nicolai; Marquez, Josefina; Pamies, Silvana Carina; Sosa, Gladis Laura; Peruchena, Nelida Maria; Understanding the Chloride Affinity of Barbiturates for Anion Receptor Design; Wiley VCH Verlag; Chemphyschem; 22; 7; 2-2021; 665-674
dc.identifier.issn
1439-4235
dc.identifier.uri
http://hdl.handle.net/11336/150432
dc.description.abstract
Due to their potential binding sites, barbituric acid (BA) and its derivatives have been used in metal coordination chemistry. Yet their abilities to recognize anions remain unexplored. In this work, we were able to identify four structural features of barbiturates that are responsible for a certain anion affinity. The set of coordination interactions can be finely tuned with covalent decorations at the methylene group. DFT-D computations at the BLYP-D3(BJ)/aug-cc-pVDZ level of theory show that the C−H bond is as effective as the N−H bond to coordinate chloride. An analysis of the electron charge density at the C−H⋅⋅⋅Cl− and N−H⋅⋅⋅Cl− bond critical points elucidates their similarities in covalent character. Our results reveal that the special acidity of the C−H bond shows up when the methylene group moves out of the ring plane and it is mainly governed by the orbital interaction energy. The amide and carboxyl groups are the best choices to coordinate the ion when they act together with the C−H bond. We finally show how can we use this information to rationally improve the recognition capability of a small cage-like complex that is able to coordinate NaCl.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Wiley VCH Verlag
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
ANIONS
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COORDINATION MODES
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DENSITY FUNCTIONAL CALCULATIONS
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HYDROGEN BONDS
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RECEPTORS
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Físico-Química, Ciencia de los Polímeros, Electroquímica
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Understanding the Chloride Affinity of Barbiturates for Anion Receptor Design
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2022-01-20T13:11:23Z
dc.journal.volume
22
dc.journal.number
7
dc.journal.pagination
665-674
dc.journal.pais
Alemania
dc.journal.ciudad
Weinheim
dc.description.fil
Fil: Petelski, Andre Nicolai. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Química Básica y Aplicada del Nordeste Argentino. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina
dc.description.fil
Fil: Marquez, Josefina. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Departamento de Ingeniería Química. Laboratorio de Química Teórica y Experimental; Argentina
dc.description.fil
Fil: Pamies, Silvana Carina. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Departamento de Ingeniería Química. Laboratorio de Química Teórica y Experimental; Argentina
dc.description.fil
Fil: Sosa, Gladis Laura. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Departamento de Ingeniería Química. Laboratorio de Química Teórica y Experimental; Argentina
dc.description.fil
Fil: Peruchena, Nelida Maria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Química Básica y Aplicada del Nordeste Argentino. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina
dc.journal.title
Chemphyschem
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/cphc.202100008
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/cphc.202100008
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