Synthesis, crystal structure and spectral characterization of (Z)-2,8-dibromo-9-(bromomethylene)-3,5,5-trimethyl-6,7,8,9-tetrahydro-5H-benzo [7] annulene

Abstract A novel (Z)-2,8-dibromo-9-(bromomethylene)-3,5,5-trimethyl-6,7,8,9-tetrahydro-5H-benzo [7] annulene was synthesized by bromination with N-Bromosuccinimide (NBS) of Aryl-Himachalene. The product of this reaction was characterized by 13C NMR, 1H NMR, FT-IR spectroscopy and single crystal X-ray diffraction. In the solid state, the molecules are associated by Br⋯Br halogen bonds, C–H···π interactions and C–H⋯Br hydrogen bonds. The optimized structure parameters of the studied molecule was determined theoretically using density functional theory (DFT/B3LYP) method 6-31 + G(d, p) basis set, and compared with previously reported experimental findings. Calculated chemical shift values and vibrational wavenumbers showed good agreement with the experimental data. The electronic properties, such as HOMO and LUMO energies, and molecular electrostatic potential (MEP) are also performed.