Synthesis, structural, theoretical studies and biological activities of 3-(arylamino)-2-phenyl-1H-inden-1-one derivative

Article abstract of DOI:10.1016/j.molstruc.2014.03.042

Five derivatives of 2-phenyl-1H-indene-1-one have been prepared and fully characterized. Spectroscopic techniques such as FT-IR, ¹H NMR, mass spectrometry, and elemental analysis were used to investigate the chemical structures and physical pro

Full text of DOI:10.1016/j.molstruc.2014.03.042

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Accepted Manuscript
Synthesis, Structural, Theoretical Studies and Biological Activities of 3-(aryla-
mino)-2-phenyl-1H-inden-1-one Derivative
Hamdy S. El–Sheshtawy, Ahmed M. Abou Baker
PII:
S0022-2860(14)00310-X
DOI:
http://dx.doi.org/10.1016/j.molstruc.2014.03.042
MOLSTR 20476
Reference:
Journal of Molecular Structure
To appear in:
Received Date:
Revised Date:
Accepted Date:
7 November 2013
13 March 2014
14 March 2014
Please cite this article as: H.S. El–Sheshtawy, A.M. Abou Baker, Synthesis, Structural, Theoretical Studies and
Biological Activities of 3-(arylamino)-2-phenyl-1H-inden-1-one Derivative, Journal of Molecular Structure (2014),
doi: http://dx.doi.org/10.1016/j.molstruc.2014.03.042
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Synthesis, Structural, Theoretical Studies and Biological Activities of 3-(arylamino)-2-
phenyl-1H-inden-1-one Derivative
Hamdy S. El−Sheshtawya*, and Ahmed M. Abou Bakera
a Chemistry Department, Faculty of Science, South Valley University, 83523 Qena, Egypt
Abstract
Five derivatives of 2-phenyl-1H-indene-1-one have been prepared and fully characterized.
Spectroscopic techniques such as FT-IR, 1H-NMR, mass spectrometry, and elemental analysis
were used to investigate the chemical structures and physical properties of the prepared
compounds. The optimized structures and the distribution of the frontier molecular orbital
were obtained using density functional theory (DFT) at B3LYP/6-311++G(d,p) level of
theory. Additionally, the UV spectral properties of the indene compounds were corroborated
by frontier orbital (HOMO and LUMO) calculations. Intramolecular charge transfer (ICT)
peak has been observed in the UV spectra of the compounds and theoretically confirmed by
the HOMO and LUMO analysis. The potential use of these compounds as antibacterial agents
was investigated. The results show that indene-1-one derivatives have an antibacterial activity
for both gram-negative (Pseudomonas aeruginosa) and gram-positive (Methicillin Resistant
Staphylococcus aureus) bacteria.

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Keywords: 3-(arylamino)-2-phenyl-1H-inden-1-one, spectral properties, DFT calculations,
biological activities.
_________________________________________________________________
a*Corresponding author:
Tel.: +201062668020,
Fax: +2096-5211279
E-mail: h.elsheshtawy@sci.svu.edu.eg
1. Introduction
Indene compounds have recently attracted the interest of researchers as important
intermediates for the synthesis of a wide range of chemicals such as polymers, liquid crystals
and enzyme inhibitors [1-6]. In particular, metal complexes of indene derivatives have shown
an exceptional catalytic efficiency in the polymerization of ethylene and propylene (Ziegler-
Natta type catalysis). Furthermore, indene derivatives have been widely used as cancer
inhibition drugs, pesticides and antimicrobial agents [7, 8]. Remarkably, 2-phenyl-1H-inden-
1-one has been well known as anticoagulant and vitamin K antagonist [9, 10]. Therefore,
efficient synthetic pathways to indene derivatives are in high demand. The second position is
particularly reactive and indan-1,3-dione derivatives with unique chemical and physical
properties [11, 12] may be obtained by functionalizing the methylene bridge [11-13]. The
photophysical properties of the derivatives obtained are mainly due to the strong electron-
accepting ketone moieties that may couple with electron-donating substitutents such as phenyl
[11]. On the other hand, addition reactions on the carbonyl groups of 2-phenyl-indan-1,3-
dione in the literature is scarce [14].

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Donor−acceptor (D−A) molecules have been intensively explored for their potential use
as efficient electroluminescent and nonlinear optical materials [15-18]. In this context, the
efficiency largely depends on the optimum choice of a good donor-acceptor pair and the
proper spacing group. Most of the previously reported materials were based on conjugated
polymers [19-21]. Only recently, small molecules with intramolecular charge transfer (ICT)
are being investigated for their potential use as nonlinear optics materials [22-24].
In this work five derivatives of 3-(arylamino)-2-phenyl-1H-inden-1-one have been
1
synthesized and characterized with spectroscopic techniques such as FT−IR, H-NMR, mass
spectrometry and elemental analysis for their possible use as electroluminescent and nonlinear
optical materials. Quantum chemical calculations were performed using density-functional
theory (DFT) at B3LYP/6-311++G(d,p) level of theory for more insight on the electronic
structure and the confirmations of the compounds. The UV-Vis spectroscopic studies, along
with the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular
orbital (LUMO) analysis have been used to explain the ICT phenomena within these
molecules. In addition, the potential use of the studied compounds as antibacterial agents was
investigated.
2. Experimental
2.1 Materials, measurments, and calculations
All chemicals and reagents used for the synthesis were purchased from Merck KGaA,
Darmstadt, Germany, and used without further purification. Melting points (uncorrected)
were recorded on a Griffin & George melting point apparatus . The UV-vis absorption spectra
1
were recorded on a UV-2401PC "UV-VIS Recording Spectrophotometer". The H-NMR
spectra were recorded on a Varian Mercury-300BB "NMR300" spectrometer using a TMS
internal reference. Electron impact mass spectra were obtained at 70 eV electron impact