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

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 intermolecu...

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Autores principales: Saeed, Aamer, Flörke, Ulrich, Fantoni, Adolfo Carlos, Khurshid, Asma, Pérez, Hiram, Erben, Mauricio Federico
Formato: Articulo
Lenguaje:Inglés
Publicado: 2017
Materias:
Química
Intermolecular interactions
Electrostatic potentials
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/103581
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-103581
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Intermolecular interactions
Electrostatic potentials
spellingShingle Química
Intermolecular interactions
Electrostatic potentials
Saeed, Aamer
Flörke, Ulrich
Fantoni, Adolfo Carlos
Khurshid, Asma
Pérez, Hiram
Erben, Mauricio Federico
Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
topic_facet Química
Intermolecular interactions
Electrostatic potentials
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.
format Articulo
Articulo
author Saeed, Aamer
Flörke, Ulrich
Fantoni, Adolfo Carlos
Khurshid, Asma
Pérez, Hiram
Erben, Mauricio Federico
author_facet Saeed, Aamer
Flörke, Ulrich
Fantoni, Adolfo Carlos
Khurshid, Asma
Pérez, Hiram
Erben, Mauricio Federico
author_sort Saeed, Aamer
title Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
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
publishDate 2017
url http://sedici.unlp.edu.ar/handle/10915/103581
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