Synthesis, Crystal Structure, Hirshfeld Surface Analysis, Energy Framework Calculations, and Halogen Bonding Investigation of Benzene-1,3,5-triyltris((4-chlorophenyl)methanone)

Abstract

We synthesized 1,3,5-triyltris((4-chlorophenyl)methanone) by a condensation reaction in glacial acetic acid and studied utilizing spectroscopic and analytical techniques such as ultraviolet, infrared, mass, elemental, and nuclear magnetic resonance (NMR) spectroscopy, as well as X-ray crystallography. The effect of chlorine substitution in the 1,3,5-triaroylbenzene compound in solid-state arrangements was studied. Halogen bonds are detected in the solid-state structures of the titled compound. A dimeric structure is formed due to the presence of two C-Cl···Cl Type I halogen interactions. Additionally, a delocalized Type III C-Cl···π interaction were reported. C-Cl···H hydrogen bonding and π···π interaction were also reported. Hirshfeld surface analysis, 3D fingerprint, the energy framework, and the electro-optic potential were used to evaluate such interactions.

Keywords

• halogen bonding
• Hirshfeld surface
• 1,3,5-triyltris((4-chlorophenyl)methanone)
• energy framework calculations