Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules

Autores
Petelski, Andre Nicolai; Pamies, Silvana Carina; Márquez, María Josefina; Peruchena, Nélida María; Sosa, Gladis Laura
Año de publicación
2022
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Melamine (M) is a popular triamine triazine compound in the field of supramolecular materials. In this work, we have computationally investigated how substituents can be exploited to improve the binding strength of M supramolecules. Two types of covalent modifications were studied: the substitution of an H atom within an amine group NHR, and the replacement of the whole NH2 group (R=H, F, CH3 and COCH3). Through our dispersion-corrected density functional theory computations, we explain which covalent modification will show the best self-assembling capabilities, and why the binding energy is enhanced. Our charge density and molecular orbital analyses indicate that the best substituents are those that generate a charge accumulation on the endocyclic N atom, providing an improvement of the electrostatic attraction. At the same time the substituent assists the main N H···N hydrogen bonds by interacting with the amino group of the other monomer. We also show how the selected group notably boosts the strength of hexameric rosettes. This research, therefore, provides molecular tools for the rational design of emerging materials based on uneven hydrogen-bonded arrangements.
Fil: Petelski, Andre Nicolai. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina. Fil: Petelski, Andre Nicolai. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.
Fil: Pamies, Silvana Carina. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina.
Fil: Márquez, María Josefina. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina.
Fil: Sosa, Gladis Laura. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación en Química Teórica y Experimental; Argentina.
Fil: Peruchena, Nélida María. Universidad Nacional del Nordeste. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.
Fil: Sosa, Gladis Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.
Fil: Peruchena, Nélida María. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Laboratorio de Estructura Molecular y Propiedades; Argentina.
Peer Reviewed
Materia
amines
hydrogen bonds
self-assembly
substituent effects
isomers
Nivel de accesibilidad
acceso abierto
Condiciones de uso
2023-10-27T22:50:15Z
Repositorio
Repositorio Institucional Abierto (UTN)
Institución
Universidad Tecnológica Nacional
OAI Identificador
oai:ria.utn.edu.ar:20.500.12272/8653
Acceder
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network_acronym_str RIAUTN
repository_id_str a
network_name_str Repositorio Institucional Abierto (UTN)
spelling Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramoleculesPetelski, Andre NicolaiPamies, Silvana CarinaMárquez, María JosefinaPeruchena, Nélida MaríaSosa, Gladis Lauraamineshydrogen bondsself-assemblysubstituent effectsisomersMelamine (M) is a popular triamine triazine compound in the field of supramolecular materials. In this work, we have computationally investigated how substituents can be exploited to improve the binding strength of M supramolecules. Two types of covalent modifications were studied: the substitution of an H atom within an amine group NHR, and the replacement of the whole NH2 group (R=H, F, CH3 and COCH3). Through our dispersion-corrected density functional theory computations, we explain which covalent modification will show the best self-assembling capabilities, and why the binding energy is enhanced. Our charge density and molecular orbital analyses indicate that the best substituents are those that generate a charge accumulation on the endocyclic N atom, providing an improvement of the electrostatic attraction. At the same time the substituent assists the main N H···N hydrogen bonds by interacting with the amino group of the other monomer. We also show how the selected group notably boosts the strength of hexameric rosettes. This research, therefore, provides molecular tools for the rational design of emerging materials based on uneven hydrogen-bonded arrangements.Fil: Petelski, Andre Nicolai. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina. Fil: Petelski, Andre Nicolai. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.Fil: Pamies, Silvana Carina. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina.Fil: Márquez, María Josefina. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina.Fil: Sosa, Gladis Laura. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación en Química Teórica y Experimental; Argentina.Fil: Peruchena, Nélida María. Universidad Nacional del Nordeste. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.Fil: Sosa, Gladis Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.Fil: Peruchena, Nélida María. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Laboratorio de Estructura Molecular y Propiedades; Argentina.Peer Reviewed2023-10-27T22:50:15Z2023-10-27T22:50:15Z2022-04-14info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articulopdfapplication/pdfhttp://hdl.handle.net/20.500.12272/8653doi.org/10.1002/cphc.202200151enginfo:eu-repo/semantics/openAccess2023-10-27T22:50:15ZAcceso abiertoreponame:Repositorio Institucional Abierto (UTN)instname:Universidad Tecnológica Nacional2026-09-24T12:45:39Zoai:ria.utn.edu.ar:20.500.12272/8653instacron:UTNInstitucionalhttp://ria.utn.edu.ar/Universidad públicaNo correspondehttp://ria.utn.edu.ar/oaigestionria@rec.utn.edu.ar; fsuarez@rec.utn.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:a2026-09-24 12:45:41.032Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacionalfalse
dc.title.none.fl_str_mv Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules
title Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules
spellingShingle Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules
Petelski, Andre Nicolai
amines
hydrogen bonds
self-assembly
substituent effects
isomers
title_short Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules
title_full Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules
title_fullStr Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules
title_full_unstemmed Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules
title_sort Impact of covalent modifications on the hydrogen bond strengths in diaminotriazine supramolecules
dc.creator.none.fl_str_mv Petelski, Andre Nicolai
Pamies, Silvana Carina
Márquez, María Josefina
Peruchena, Nélida María
Sosa, Gladis Laura
author Petelski, Andre Nicolai
author_facet Petelski, Andre Nicolai
Pamies, Silvana Carina
Márquez, María Josefina
Peruchena, Nélida María
Sosa, Gladis Laura
author_role author
author2 Pamies, Silvana Carina
Márquez, María Josefina
Peruchena, Nélida María
Sosa, Gladis Laura
author2_role author
author
author
author
dc.subject.none.fl_str_mv amines
hydrogen bonds
self-assembly
substituent effects
isomers
topic amines
hydrogen bonds
self-assembly
substituent effects
isomers
dc.description.none.fl_txt_mv Melamine (M) is a popular triamine triazine compound in the field of supramolecular materials. In this work, we have computationally investigated how substituents can be exploited to improve the binding strength of M supramolecules. Two types of covalent modifications were studied: the substitution of an H atom within an amine group NHR, and the replacement of the whole NH2 group (R=H, F, CH3 and COCH3). Through our dispersion-corrected density functional theory computations, we explain which covalent modification will show the best self-assembling capabilities, and why the binding energy is enhanced. Our charge density and molecular orbital analyses indicate that the best substituents are those that generate a charge accumulation on the endocyclic N atom, providing an improvement of the electrostatic attraction. At the same time the substituent assists the main N H···N hydrogen bonds by interacting with the amino group of the other monomer. We also show how the selected group notably boosts the strength of hexameric rosettes. This research, therefore, provides molecular tools for the rational design of emerging materials based on uneven hydrogen-bonded arrangements.
Fil: Petelski, Andre Nicolai. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina. Fil: Petelski, Andre Nicolai. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.
Fil: Pamies, Silvana Carina. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina.
Fil: Márquez, María Josefina. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación Química Teórica Experimental; Argentina.
Fil: Sosa, Gladis Laura. Universidad Tecnológica Nacional. Facultad Regional Resistencia. Grupo de Investigación en Química Teórica y Experimental; Argentina.
Fil: Peruchena, Nélida María. Universidad Nacional del Nordeste. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.
Fil: Sosa, Gladis Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Química Básica y Aplicada del Nordeste Argentino; Argentina.
Fil: Peruchena, Nélida María. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas y Naturales y Agrimensura. Laboratorio de Estructura Molecular y Propiedades; Argentina.
Peer Reviewed
description Melamine (M) is a popular triamine triazine compound in the field of supramolecular materials. In this work, we have computationally investigated how substituents can be exploited to improve the binding strength of M supramolecules. Two types of covalent modifications were studied: the substitution of an H atom within an amine group NHR, and the replacement of the whole NH2 group (R=H, F, CH3 and COCH3). Through our dispersion-corrected density functional theory computations, we explain which covalent modification will show the best self-assembling capabilities, and why the binding energy is enhanced. Our charge density and molecular orbital analyses indicate that the best substituents are those that generate a charge accumulation on the endocyclic N atom, providing an improvement of the electrostatic attraction. At the same time the substituent assists the main N H···N hydrogen bonds by interacting with the amino group of the other monomer. We also show how the selected group notably boosts the strength of hexameric rosettes. This research, therefore, provides molecular tools for the rational design of emerging materials based on uneven hydrogen-bonded arrangements.
publishDate 2022
dc.date.none.fl_str_mv 2022-04-14
2023-10-27T22:50:15Z
2023-10-27T22:50:15Z
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/20.500.12272/8653
doi.org/10.1002/cphc.202200151
url http://hdl.handle.net/20.500.12272/8653
identifier_str_mv doi.org/10.1002/cphc.202200151
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
2023-10-27T22:50:15Z
Acceso abierto
eu_rights_str_mv openAccess
rights_invalid_str_mv 2023-10-27T22:50:15Z
Acceso abierto
dc.format.none.fl_str_mv pdf
application/pdf
dc.source.none.fl_str_mv reponame:Repositorio Institucional Abierto (UTN)
instname:Universidad Tecnológica Nacional
reponame_str Repositorio Institucional Abierto (UTN)
collection Repositorio Institucional Abierto (UTN)
instname_str Universidad Tecnológica Nacional
repository.name.fl_str_mv Repositorio Institucional Abierto (UTN) - Universidad Tecnológica Nacional
repository.mail.fl_str_mv gestionria@rec.utn.edu.ar; fsuarez@rec.utn.edu.ar
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score 13.24418

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