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X-ray molecular structure and theoretical study of 1,4-bis[2-cyano-2-(o-pyridyl)ethenyl]benzene

  • M. Percino EMAIL logo , Maria Castro , Margarita Ceron , Guillermo Soriano-Moro , Victor Chapela und Francisco Melendez
Veröffentlicht/Copyright: 30. Oktober 2013
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Chemical Papers
Aus der Zeitschrift Chemical Papers Band 68 Heft 2

Abstract

The structural characterisation of the molecule 1,4-bis[2-cyano-2-(o-pyridyl)ethenyl] benzene obtained through Knoevenagel condensation is reported. The single crystals, as light brown rods, were cultured from a chloroform solution using a slow evaporation method at ambient temperature. The compound crystallised in the monoclinic system belonging to the C2/c space group with a = 26.4556(9) Å, b = 3.73562(10) Å, c = 18.4230(6) Å, β = 109.841(4)° and the asymmetric unit comprising Z = 4. The structure is ordered and the molecules of the title compound exhibited a lattice with water molecules located at sites of inversion and two-fold axial symmetries. Thus, only halves of the molecules are symmetrically independent. The lattice is reported and contrasted with X-ray single-crystal diffraction and theoretical calculations of 1,4-bis(1-cyano-2-phenylethenyl)benzene. By using density functional theory (DFT) and second order Moller-Plesset (MP2) theoretical calculations, the ground state geometry in the whole molecule at the B3LYP/6-31+G(d,p), and MP2/6-31+G(d,p) theory levels, respectively, were optimised. The DFT calculations showed a quasi-planar structure of the molecule, whereas the wave function-based MP2 method afforded a non-planar optimised structure with significant torsion angles between the pyridine and phenyl rings.

Keywords: cyano-substituted acrylonitrile compound; X-ray structure; molecular structure; DFT and MP2 calculations

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Published Online: 2013-10-30
Published in Print: 2014-2-1

© 2013 Institute of Chemistry, Slovak Academy of Sciences

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https://doi.org/10.2478/s11696-013-0434-5
Schlagwörter für diesen Artikel
cyano-substituted acrylonitrile compound; X-ray structure; molecular structure; DFT and MP2 calculations

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