Synthesis, XRD single crystal structure analysis, vibrational spectral analysis, molecular dynamics and molecular docking studies of 2-(3-methoxy-4-hydroxyphenyl) benzothiazole

• Published in: Journal of molecular structure 2017-11, Vol.1148, p.282-292
• Main Authors: Sarau Devi, A., Aswathy, V.V., Sheena Mary, Y., Yohannan Panicker, C., Armaković, Stevan, Armaković, Sanja J., Ravindran, Reena, Van Alsenoy, C.
• Format: Article
• Language: English
• Subjects: ALIE; BDE; DFT; Molecular docking; RDF; Thiazole
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2017.07.065

The vibrational spectra and corresponding vibrational assignments of 2-(3-methoxy-4-hydroxyphenyl)benzothiazole is reported. Single crystal XRD data of the title compound is reported and the orientation of methoxy group is cis to nitrogen atom of the thiazole ring. The phenyl ring breathing modes of the title compound are assigned at 1042 and 731 cm−1 theoretically. The charge transfer within the molecule is studied using frontier molecular orbital analysis. The chemical reactivity descriptors are calculated theoretically. The NMR spectral data predicted theoretically are in good agreement with the experimental data. The strong negative region spread over the phenyl rings, nitrogen atom and oxygen atom of the hydroxyl group in the MEP plot is due to the immense conjugative and hyper conjugative resonance charge delocalization of π-electrons. Molecule sites prone to electrophilic attacks have been determined by analysis of ALIE surfaces, while Fukui functions provided further insight into the local reactivity properties of title molecule. Autoxidation properties have been investigated by calculation of bond dissociation energies (BDEs) of hydrogen abstraction, while BDEs of the rest of the single acyclic bonds were valuable for the further investigation of degradation properties. Calculation of radial distribution functions was performed in order to determine which atoms of the title molecule have pronounced interactions with water molecules. The title compound forms a stable complex with aryl hydrocarbon receptor and can be a lead compound for developing new anti-tumor drug. Antimicrobial properties of the title compound was screened against one bacterial culture Escherchia coli and four fungal cultures viz., Aspergillus niger, Pencillum chrysogenum, Saccharomyces cerevisiae and Rhyzopus stolonifer. [Display omitted] •A novel thiazole derivative is synthesized and single crystal XRD is reported.•The recorded FT-IR and FT-Raman spectra were interpreted in detail with the aid of DFT and PED analysis.•Local reactivity properties are investigated by ALIE surfaces and Fukui functions.•Bond dissociation energies are calculated to predict the possible degradation properties.•Docking studies predict that the title compound can be a lead compound for developing anti-tumor drug.