Jump to main content
Jump to site search

Issue 11, 2017
Previous Article Next Article

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

Author affiliations

Abstract

The crystal structures of four 1-(R-phenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-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[double bond, length as m-dash]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[double bond, length as m-dash]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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 Dec 2016, accepted on 12 Feb 2017 and first published on 13 Feb 2017


Article type: Paper
DOI: 10.1039/C6CE02619B
CrystEngComm, 2017,19, 1495-1508

  •   Request permissions

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

    A. Saeed, U. Flörke, A. Fantoni, A. Khurshid, H. Pérez and M. F. Erben, CrystEngComm, 2017, 19, 1495
    DOI: 10.1039/C6CE02619B

Search articles by author

Spotlight

Advertisements