Unraveling non-covalent interactions in bis-chalcone: A crystallographic and theoretical studies

A new bis-chalcone THXA, (2E,2 ' E)-1,1 '-(((1,4-phenylenebis(methylene))bis(oxy))bis(2,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one) is synthesized and characterized by spectroscopic and single crystal X-ray diffraction techniques from chalcone (E)-1-(2-hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one) and xylene dibromide. The intermolecular non-covalent interactions such as pi center dot center dot center dot pi, C-H center dot center dot center dot S and C-H center dot center dot center dot pi participate decisive roles in the development of supramolecular structures. An inclusive Hirshfeld surface analysis discloses the presence of intermolecular non-covalent interactions. The 2D fingerprint plots reveal individual atom's percentage contributions in construction of the non-covalent interactions. Hirshfeld energy framework study affirms dominance of the dispersive pi-pi interaction in THXA. Further, energetic estimation for non-covalent interactions of dimeric unit has been calculated through density functional theory (DFT). The molecular electrostatic potential (MEP) surfaces help to describe the charge distribution in THXA. Additionally, the non-covalent interactions in THXA are also examined by computational tools like non-covalent interaction (NCI) plot index and quantum theory of atoms in molecules (QTAIM) analysis.

Automated summary

The structure and intermolecular interactions of a newly synthesized bis-chalcone THXA were studied using experimental and computational methods. The importance of non-covalent interactions such as pi center dot center dot center dot pi, C-H center dot center dot center dot S, and C-H center dot center dot center dot pi was revealed.