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Issue 113, 2016, Issue in Progress
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Spectroscopic, single crystal XRD structure, DFT and molecular dynamics investigation of 1-(3-chloro-4-fluorophenyl)-3-[3-(trifluoromethyl)phenyl]thiourea

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Abstract

The title compound 1-(3-chloro-4-fluorophenyl)-3-[3-(trifluoromethyl) phenyl]thiourea (ANF-2) was synthesized and structurally characterized by single crystal XRD. The optimized molecular structure, vibrational frequencies, and corresponding vibrational assignments of ANF-2 have been investigated experimentally and theoretically using Gaussian 09 and Schrödinger Materials Science Suite software packages. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. Gauge-including atomic orbital NMR chemical shifts calculations were carried out and compared with experimental data, while the first hyperpolarizability is 48 times that of the standard NLO material. The maximum negative region is localized over the C[double bond, length as m-dash]S group and 1,3-disubstituted phenyl ring, while the maximum positive region is localized on NH groups indicating a possible site for nucleophilic attack. Average local ionization energies have been mapped to the electron density surface in order to detect molecule sites where electrons are least tightly bound. Other possible reactive centers of the title molecule have been detected by calculation of Fukui functions. In order to investigate the possibility for autoxidation and hydrolysis of the investigated molecule, we have calculated bond dissociation energies and radial distribution functions. Charge hopping properties have been assessed using the Marcus semi-empiric approach and the results were compared with urea and thiourea molecules. The docked ligand forms a stable complex with prostaglandin E synthase and has a binding affinity value of −6.5 kcal mol−1 and the title compound can be a lead compound for developing new analgesic drugs.

Graphical abstract: Spectroscopic, single crystal XRD structure, DFT and molecular dynamics investigation of 1-(3-chloro-4-fluorophenyl)-3-[3-(trifluoromethyl)phenyl]thiourea

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Publication details

The article was received on 25 Aug 2016, accepted on 09 Nov 2016 and first published on 16 Nov 2016


Article type: Paper
DOI: 10.1039/C6RA21396K
Citation: RSC Adv., 2016,6, 111997-112015
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    Spectroscopic, single crystal XRD structure, DFT and molecular dynamics investigation of 1-(3-chloro-4-fluorophenyl)-3-[3-(trifluoromethyl)phenyl]thiourea

    Y. Sheena Mary, V. V. Aswathy, C. Y. Panicker, A. Bielenica, P. Brzózka, O. Savczenko, S. Armaković, S. J. Armaković and C. Van Alsenoy, RSC Adv., 2016, 6, 111997
    DOI: 10.1039/C6RA21396K

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