Spectral analysis and detailed quantum mechanical investigation of some acetanilide analogues and their self-assemblies with graphene and fullerene

Almuqrin A. H. , Al-Otaibi J. S. , Mary Y. S. , Thomas R., KAYA S., ÖZBAKIR IŞIN D.

JOURNAL OF MOLECULAR MODELING, vol.26, no.9, 2020 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 26 Issue: 9
  • Publication Date: 2020
  • Doi Number: 10.1007/s00894-020-04485-3
  • Journal Indexes: Science Citation Index Expanded, Scopus, Academic Search Premier, Biotechnology Research Abstracts, CAB Abstracts, EMBASE, MEDLINE, Veterinary Science Database
  • Keywords: DFT, Graphene, Fullerene, Acetanilide, Molecular docking, IMIDAZOLE DERIVATIVES, RAMAN-SPECTRA, ADSORPTION, C-60, BENZAMIDE, MOLECULES, PYRIDINE, DFT, CO


Spectroscopic analysis and different quantum mechanical studies of four pharmaceutically active compounds phenacetin, p-acetanisidide, 4 '-butoxyacetanilide, and 4 '-(3-chloropropoxy)acetanilide are reported in this manuscript. Simulated IR spectrum of these compounds was compared with experimentally available data, and essential functional group assignments were made. We also report the frontier orbital properties and other derived local energy descriptors which talks about the relative stability and reactivity. Photovoltaic efficiency of the compounds was studied from the simulated electronic spectra. The compound was found to interact with graphene and fullerene, to form molecular self-assembly. These self-assemblies showed tremendous enhancement in various physicochemical properties when compared with its constituents. The nature of the interactions between studied chemical species was discussed with the help of chemical reactivity principles. Biological activity of the compounds was predicted using molecular docking studies. It is interesting to see that on adsorption with a graphene/fullerene surface, all adsorbed complex shows enhancement in the Raman activity giving surface enhanced Raman spectra (SERS). This can be used for the detection of these drugs in a pharmacological or biological sample. Interestingly the graphene/fullerene drug molecular assembly shows enhanced biological activity when compared with individual drug molecules.