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

Chandraju Sadolalu Chidan Kumar; Hoong Kun Fun; Cemal Parlak; Lydia Rhyman; Ponnadurai Ramasami; Mahir Tursun; Siddegowda Chandraju; Ching Kheng Quah

doi:10.1016/j.saa.2014.04.155

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

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Nov 11:132:174-82. doi: 10.1016/j.saa.2014.04.155. Epub 2014 May 6.

Authors

Chandraju Sadolalu Chidan Kumar¹, Hoong Kun Fun², Cemal Parlak³, Lydia Rhyman⁴, Ponnadurai Ramasami⁵, Mahir Tursun³, Siddegowda Chandraju⁶, Ching Kheng Quah¹

Affiliations

¹ X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
² X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia; Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia.
³ Department of Physics, Dumlupinar University, Kütahya 43100, Turkey.
⁴ Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit, Mauritius.
⁵ Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit, Mauritius. Electronic address: p.ramasami@uom.ac.mu.
⁶ Department of Sugar Technology and Chemistry, Sir M. Visvesvaraya PG Center, University of Mysore, Tubinakere, Mandya 571402, India.

PMID: 24858359
DOI: 10.1016/j.saa.2014.04.155

Abstract

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 P2₁/c with the unit cell parameters a=5.7827(8)Å, b=14.590(2)Å, c=16.138(2)Å and β=89.987 (°). The CC 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.

Keywords: 5-Chlorothiophene chalcone analogue; Crystal structure; DFT; Vibrational spectra; XRD.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Electrons
Isomerism
Models, Molecular*
Molecular Conformation
Naphthalenes / chemical synthesis*
Naphthalenes / chemistry*
Spectroscopy, Fourier Transform Infrared
Spectrum Analysis, Raman*
Thiophenes / chemical synthesis*
Thiophenes / chemistry*
Vibration
X-Ray Diffraction

Substances

(2E)-1-(5-chlorothiophen-2-yl)-3-(naphthalen-2-yl)prop-2-en-1-one
Naphthalenes
Thiophenes