Synthesis, molecular structure, FT-IR, Raman, XRD and theoretical investigations of (2E)-1-(5-chlorothiophen-2-yl)-3-(naphthalen-2-yl) prop-2-en-1-one

A novel (2E)-1-(5-chlorothiophen-2-yl)-3-(naphthalen-2-yl)prop-2-en-1-one [C17H11ClOS] compound has been synthesized and its structure has been characterized by FT-IR, Raman and single-crystal X-ray diffraction techniques. The isomers, optimized geometrical parameters, normal mode frequencies and corresponding vibrational assignments of the compound have been examined by means of the density functional theory method, employing, the Becke-3-Lee-Yang-Parr functional and the 6-311+G(3df,p) basis set. Reliable vibrational assignments and molecular orbitals have been investigated by the potential energy distribution and natural bonding orbital analyses, respectively. The compound crystallizes in the monoclinic space group P2(1)/c with the unit cell parameters a = 5.7827(8) angstrom, b = 14.590(2) angstrom, c = 16.138(2) angstrom and beta = 89.987 (degrees). The C=C bond of the central enone group adopts an E configuration. There is a good agreement between the theoretically predicted structural parameters and vibrational frequencies and those obtained experimentally. (C) 2014 Elsevier B.V. All rights reserved.