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

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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.

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Authors and Affiliations

  1. Polymers Laboratory, Chemistry Center, Institute of Sciences, Autonomous University of Puebla, Complex of Sciences, ICUAP, 103H, Puebla, Mexico

    M. Judith Percino, Maria Eugenia Castro, Margarita Ceron, Guillermo Soriano-Moro & Victor M. Chapela

  2. Theoretical Chemistry Laboratory, Investigation Center, Department of Physical Chemistry, Faculty of Chemical Sciences, Autonomous University of Puebla, 105L, 22 Sur y San Claudio, University City, Puebla City, Pue., 72570, Mexico

    Francisco J. Melendez

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  1. M. Judith Percino
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  2. Maria Eugenia Castro
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  3. Margarita Ceron
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  4. Guillermo Soriano-Moro
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  5. Victor M. Chapela
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  6. Francisco J. Melendez
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Correspondence to M. Judith Percino.

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Percino, M.J., Castro, M.E., Ceron, M. et al. X-ray molecular structure and theoretical study of 1,4-bis[2-cyano-2-(o-pyridyl)ethenyl]benzene. Chem. Pap. 68, 272–282 (2014). https://doi.org/10.2478/s11696-013-0434-5

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