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⋯SC 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⋯SC 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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/48470
Ver los metadatos del registro completo
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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⋯SC 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⋯SC 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⋯SC 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⋯SC 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⋯SC 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⋯SC 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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1844613254640304128 |
score |
13.070432 |