Structural Characterization, Theoretical Investigation and Hirshfeld Surface Analysis of 2,6-(E,E)-bis((thiophene-2-yl)methylene)cyclohexanone

Year 2019, , 47 - 58, 15.12.2019

Gül Yakalı , Abdullah Biçer , Günseli Turgut Cin

https://doi.org/10.33435/tcandtc.457453

Cited By: 1

Abstract

The bis(chalcone) compound, 2,6-(E,E)-bis((thiophene-2-yl)methylene)cyclohexanone,
has been synthesized and characterized by FTIR, ¹H-NMR, ¹³C-NMR
techniques, X-ray structure analysis. The optimized molecular structure of the
studied compound is calculated using DFT/B3LYP with 6-31G (d,p) level.
The calculated geometrical parameters are in good agreement with the
experimental data obtained from our reported X-ray structure. The calculated IR
fundamental bands, ¹H and ¹³C NMR chemical shifts of the
compound  were assigned and compared with
the experimental data. Additionally, frontier
molecular orbital energies (HOMO, LUMO), their energy gap (, molecular electrostatic potential analysis of the compound
have been calculated by the same method. The molecular electrostatic potential
(MEP) was used to visualize the charge distribution on the molecule. In
addition, the
intercontacts in the crystal structure are analyzed using Hirshfeld surfaces
computational method. The title compound (C₁₆H₁₄OS₂)
crystallizes in the monoclinic
chiral space group P21/c with a=15.0492(10)Å, b=12.0085(9)Å, c=7.6283(6)
Å, β=95.883(7)^o, V=1371.31(17)ų, D_calc=1.387g/cm³. The central cyclohexanone
ring has a flattened chair conformation and the
substituents at the vinyl group of each chalcone moiety exhibit a trans
(entgegen) disposition, and the two thiophene rings adopt a syn orientation and
are located on the both side of the cyclohexanone. The asymmetric unit
of the title compound, C₁₆H₁₄OS₂, contains one-half
of a molecule. The other half of the molecule is generated with (x,y,-z)  symmetry operator. In the molecule there are two weak
C-H…S and C-H…O intramolecular and only C-H…O intermolecular hydrogen bonds. In
addition, π…π interactions are found in the crystal structure between the
thiophene rings.

Keywords

Bis(chalcone), X-ray crystallography, DFT

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