Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives

Autores
Saeed, Aamer; Flörke, Ulrich; Fantoni, Adolfo Carlos; Khurshid, Asma; Pérez, Hiram; Erben, Mauricio Federico
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The crystal structures of four 1-(R-phenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2IJ1H)-thione derivatives [R = 2-chloro (1), 2,3-di-chloro (2), 2,4-di-methyl (3), and 4-methoxy (4)] were determined and analysis of their molecular conformations was carried out. A comparative study of the intermolecular interactions—including eight closely related structures from CSD—was performed and the degree of isostructurality was quantified. The intermolecular interactions were characterized in terms of the periodic system electron density and the topological analysis highlighted the role of N–H⋯SC hydrogen bonds in the stabilization of the different supramolecular architectures. PIXEL lattice energy calculations revealed that the dispersion component was the major contributor, together with the important role of the Coulombic term to the total energy. The interaction energies for molecular pairs involving N–H⋯SC hydrogen bonds indicated a dominant contribution to packing stabilization coming from the Coulombic components. Hirshfeld surfaces and fingerprint plots allowed us to visualize different intermolecular contacts and their relative contributions to the total surface for each compound. Analysis of the electrostatic potentials (ESP) correlated well with the computed energies, thus characterizing the strengths of the different interactions.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Flörke, Ulrich. University of Paderborn; Alemania
Fil: Fantoni, Adolfo Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Khurshid, Asma. Quaid-I-Azam University; Pakistán
Fil: Pérez, Hiram. Universidad de La Habana; Cuba
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Materia
Thiones
Molecular Structure
Intermolecular Interactions
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/48470

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spelling Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivativesSaeed, AamerFlörke, UlrichFantoni, Adolfo CarlosKhurshid, AsmaPérez, HiramErben, Mauricio FedericoThionesMolecular StructureIntermolecular Interactionshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The crystal structures of four 1-(R-phenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2IJ1H)-thione derivatives [R = 2-chloro (1), 2,3-di-chloro (2), 2,4-di-methyl (3), and 4-methoxy (4)] were determined and analysis of their molecular conformations was carried out. A comparative study of the intermolecular interactions—including eight closely related structures from CSD—was performed and the degree of isostructurality was quantified. The intermolecular interactions were characterized in terms of the periodic system electron density and the topological analysis highlighted the role of N–H⋯SC hydrogen bonds in the stabilization of the different supramolecular architectures. PIXEL lattice energy calculations revealed that the dispersion component was the major contributor, together with the important role of the Coulombic term to the total energy. The interaction energies for molecular pairs involving N–H⋯SC hydrogen bonds indicated a dominant contribution to packing stabilization coming from the Coulombic components. Hirshfeld surfaces and fingerprint plots allowed us to visualize different intermolecular contacts and their relative contributions to the total surface for each compound. Analysis of the electrostatic potentials (ESP) correlated well with the computed energies, thus characterizing the strengths of the different interactions.Fil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: Flörke, Ulrich. University of Paderborn; AlemaniaFil: Fantoni, Adolfo Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Khurshid, Asma. Quaid-I-Azam University; PakistánFil: Pérez, Hiram. Universidad de La Habana; CubaFil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaRoyal Society of Chemistry2017-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48470Saeed, Aamer; Flörke, Ulrich; Fantoni, Adolfo Carlos; Khurshid, Asma; Pérez, Hiram; et al.; Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives; Royal Society of Chemistry; CrystEngComm; 19; 11; 3-2017; 1495-15081466-8033CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c6ce02619binfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/CE/C6CE02619Binfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:39:39Zoai:ri.conicet.gov.ar:11336/48470instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:39:39.551CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
title Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
spellingShingle Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
Saeed, Aamer
Thiones
Molecular Structure
Intermolecular Interactions
title_short Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
title_full Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
title_fullStr Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
title_full_unstemmed Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
title_sort Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
dc.creator.none.fl_str_mv Saeed, Aamer
Flörke, Ulrich
Fantoni, Adolfo Carlos
Khurshid, Asma
Pérez, Hiram
Erben, Mauricio Federico
author Saeed, Aamer
author_facet Saeed, Aamer
Flörke, Ulrich
Fantoni, Adolfo Carlos
Khurshid, Asma
Pérez, Hiram
Erben, Mauricio Federico
author_role author
author2 Flörke, Ulrich
Fantoni, Adolfo Carlos
Khurshid, Asma
Pérez, Hiram
Erben, Mauricio Federico
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Thiones
Molecular Structure
Intermolecular Interactions
topic Thiones
Molecular Structure
Intermolecular Interactions
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The crystal structures of four 1-(R-phenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2IJ1H)-thione derivatives [R = 2-chloro (1), 2,3-di-chloro (2), 2,4-di-methyl (3), and 4-methoxy (4)] were determined and analysis of their molecular conformations was carried out. A comparative study of the intermolecular interactions—including eight closely related structures from CSD—was performed and the degree of isostructurality was quantified. The intermolecular interactions were characterized in terms of the periodic system electron density and the topological analysis highlighted the role of N–H⋯SC hydrogen bonds in the stabilization of the different supramolecular architectures. PIXEL lattice energy calculations revealed that the dispersion component was the major contributor, together with the important role of the Coulombic term to the total energy. The interaction energies for molecular pairs involving N–H⋯SC hydrogen bonds indicated a dominant contribution to packing stabilization coming from the Coulombic components. Hirshfeld surfaces and fingerprint plots allowed us to visualize different intermolecular contacts and their relative contributions to the total surface for each compound. Analysis of the electrostatic potentials (ESP) correlated well with the computed energies, thus characterizing the strengths of the different interactions.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Flörke, Ulrich. University of Paderborn; Alemania
Fil: Fantoni, Adolfo Carlos. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Khurshid, Asma. Quaid-I-Azam University; Pakistán
Fil: Pérez, Hiram. Universidad de La Habana; Cuba
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
description The crystal structures of four 1-(R-phenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2IJ1H)-thione derivatives [R = 2-chloro (1), 2,3-di-chloro (2), 2,4-di-methyl (3), and 4-methoxy (4)] were determined and analysis of their molecular conformations was carried out. A comparative study of the intermolecular interactions—including eight closely related structures from CSD—was performed and the degree of isostructurality was quantified. The intermolecular interactions were characterized in terms of the periodic system electron density and the topological analysis highlighted the role of N–H⋯SC hydrogen bonds in the stabilization of the different supramolecular architectures. PIXEL lattice energy calculations revealed that the dispersion component was the major contributor, together with the important role of the Coulombic term to the total energy. The interaction energies for molecular pairs involving N–H⋯SC hydrogen bonds indicated a dominant contribution to packing stabilization coming from the Coulombic components. Hirshfeld surfaces and fingerprint plots allowed us to visualize different intermolecular contacts and their relative contributions to the total surface for each compound. Analysis of the electrostatic potentials (ESP) correlated well with the computed energies, thus characterizing the strengths of the different interactions.
publishDate 2017
dc.date.none.fl_str_mv 2017-03
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/11336/48470
Saeed, Aamer; Flörke, Ulrich; Fantoni, Adolfo Carlos; Khurshid, Asma; Pérez, Hiram; et al.; Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives; Royal Society of Chemistry; CrystEngComm; 19; 11; 3-2017; 1495-1508
1466-8033
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48470
identifier_str_mv Saeed, Aamer; Flörke, Ulrich; Fantoni, Adolfo Carlos; Khurshid, Asma; Pérez, Hiram; et al.; Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives; Royal Society of Chemistry; CrystEngComm; 19; 11; 3-2017; 1495-1508
1466-8033
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c6ce02619b
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/CE/C6CE02619B
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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