Abstract
The title compound, (E,E)-3-methyl-2,5-bis-(4-methyl-benzyl-idene)cyclo-penta-none (MBMCP), C22H22O, was obtained by Claisen-Schmidt condensation of 4-methyl-benzaldehyde with 3-methyl-cyclo-penta-none in good yield. The structure of MBMCP was studied using UV, FT-IR and Raman spectroscopy, single-crystal X-ray diffraction (XRD) measurements, and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The mol-ecular structure of MBMCP is fully extended in the E,E configuration. C-H⋯π stacking inter-actions play a significant role in the stabilization of the mol-ecular packing. Hirshfeld surface analysis was used to qu-antify the non-covalent inter-actions in the crystal lattice. Microbiological studies were performed to investigate the anti-microbial activity of this new product.
Highlights
The Claisen–Schmidt reaction has great importance in the synthesis of organic compounds (Rajput & Kaur, 2012), in particular in the synthesis of bis(substituted-benzylidene)cycloalkanones
The structure of MBMCP was investigated by UV, Fourier–transform infrared (FT–IR) and Raman spectroscopy, single crystal X-ray diffraction (XRD) measurements and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy
The above findings prompted us to evaluate the antibacterial activity of MBMCP in vitro against four bacterial strains
Summary
The Claisen–Schmidt reaction has great importance in the synthesis of organic compounds (Rajput & Kaur, 2012), in particular in the synthesis of bis(substituted-benzylidene)cycloalkanones. This reaction is catalysed using strong acids (Dhar & Barton, 1981; Gall et al, 1999) and base with or without solvents (Geissman & Clinton, 1946; Shan et al, 2010). Numerous , 0-bis(substitutedbenzylidene)cycloalkanones exhibit biological activities (Robinson et al, 2005; Piantadosi et al, 1973) They are used as precursors for the preparation of biologically active heterocyclic compounds, such as pyrimidines (Deli et al, 1984; Guilford et al, 1999) and pyrazolines (Ziani et al, 2013). The above findings prompted us to evaluate the antibacterial activity of MBMCP in vitro against four bacterial strains
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