FT-IR, FT-Raman and NMR characterization of 2-isopropyl-5-methylcyclohexyl quinoline-2-carboxylate and investigation of its reactive and optoelectronic properties by molecular dynamics simulations and DFT calculations
Graphical abstract
Introduction
Quinoline is characterized by a double ring structure composed of a benzene and a pyridine ring fused at two adjacent carbon atoms [1]. Methylcyclohexane is a monosubstituted cyclohexane, which has one branching via the attachment of one methyl group on one carbon atom of the cyclohexane ring and the lowest form of this monosubstituted methylcyclohexane occurs when the methyl group occupies an equatorial rather than an axial position [2]. Quinoline derivatives are well known for their nonlinear optical properties [3], [4] and invite much interest due to their great potent application in the field of organic light emitting diodes (OLEDs) [5], [6], [7], [8] and are used as dopants in the polymer LED materials [9]. Certain quinoline derivatives could generate a sharp green electroluminescence and a high quantum efficiency of emission in the blue and green region [10], [11], [12], [13]. Quinoline derivatives are well known for anti-amoebic, antiviral, anti-parasitic, anti-microbial and anti-tubercular activities and possess anti-proliferative, anti-neoplastic, and cytotoxic properties [14], [15], [16], [17]. Substituted quinoline derivatives possess a broad range of bioactivities such as anticancer, anti-malarial, antibiotic, antihypertensive, platelet-derived growth factor-receptors tyrosine kinase (PDGF-RTK) inhibition, DNA-intercalating carrier, anti-inflammatory, analgesic, anti-HIV, anti-tumour, DNA binding capability and many other functional material [18], [19], [20], [21]. A series of tetracyclic indenoquinolines is used as potential anticancer agents. The compounds, which are obtained through the photo isomerization of Diels–Alder adducts formed between purpurogallin derivatives and nitrosobenzene, have in vitro anti-proliferative activities against breast (MCF-7), lung epithelial (A-549) and cervical (HeLa) adenocarcinoma cells [22]. Several novel functionalized quinolones, which exhibited potential antineoplastic activity against eukaryotic type II topoisomerases [23]. In addition to the antibacterial quinolones, specific members of this drug family display high activity against eukaryotic type II topoisomerases, as well as cultured mammalian cells and invivo tumour models. These antineoplastic quinolones represent an exploitable source of new anticancer agents which might also help addressing undesirable-toxicity and resistance phenomena [23], [24]. Jayashree et al. [25] reported the molecular docking experiments of 4-oxotheino [3,2-c]quinoline-2-carboxylates with DNA and their potential anticancer property. The author's group reported the vibrational spectroscopic studies of a number of quinoline derivatives [26], [27], [28], [29], [30], [31]. The crystal structure of the title compound, C20H25NO2 is reported Fazal et al. [32]. The present study carries out the vibrational spectral analysis of the title compound, 2-isopropyl-5-methylcyclohexyl quinoline-2-carboxylate (EF3) to elucidate the correlation amongst the molecular structure and prediction of normal modes. The redistribution of electron density in various bonding and antibonding orbitals along with stabilization energies have been calculated by natural bond orbital analysis to give clear proof of stabilization originating from hyper-conjugation of a variety of intra-molecular interaction. NMR spectra were also reported both experimentally and theoretically. The nonlinear optical properties and global chemical descriptors are also reported. Average local ionization energy maps (ALIE), bond dissociation energies (BDE) and radial distribution functions (RDF) are also reported in the present work.
Section snippets
Experimental details
All the solvents and reagents used for the synthesis were of analytical grade and procured from Sigma Chemical Co. (St. Louis, MO, USA) and quinaldic acid and menthol from Hi Media Ltd., Mumbai, India. The title compound was synthesized (Scheme 1) as reported Fazal et al. [33]. Elemental analyses were recorded on Varioel elemental analyzer (Elementar Americas, Inc. NJ, USA). NMR spectra (1H and 13C) for the compound were recorded on a 500 MHz NMR Spectrometer (Bruker advance, Reinstetten,
Results and discussion
In the following discussion, the 1,2-disubstituted phenyl ring, cyclohexyl ring and quinoline ring are designated as PhI, PhII and PhIII, respectively.
Conclusions
The theoretical optimized geometrical parameters and wave numbers have been compared with the experimental data and extensive level of relationship has been perceived. Vibrational assignments involving wave numbers tend to be created towards potential energy distribution. The calculated geometrical parameters are in agreement with the XRD data. The rings PhI and PhIII are nearly planar while the cyclohexyl ring and carbonyl group are tilted from each other. The ring breathing mode of the phenyl
Acknowledgments
Part of this work has been performed thanks to the support received from Schrödinger Inc. Part of this study was conducted within the projects supported by the Ministry of Education, Science and Technological Development of Serbia, grant numbers ON171039, TR34019. CVA is thankful to University of Antwerp for access to the university's CalcCA Supercomputer cluster.
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