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

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Abstract

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.

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Funding

The authors would like to thank the Center for Promising Research in Social Research and Women’s Studies Deanship of Scientific Research, at Nourah bint Abdulrahman University, for funding this project in 2020.

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Authors and Affiliations

  1. Department of Physics, College of Science, Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia

    Aljawhara H. Almuqrin

  2. Department of Chemistry, College of Science, Princess Nourah bint Abdulrahman University, Riyadh, Saudi Arabia

    Jamelah S. Al-Otaibi

  3. Department of Physics, Fatima Mata National College (Autonomous), Kollam, Kerala, India

    Y. Sheena Mary

  4. Department of Chemistry, St. Berchmans College (Autonomous), Changanacherry, Kerala, India

    Renjith Thomas

  5. Department of Pharmacy, Sivas Cumhuriyet University, Health Services Vocational School, 58140, Sivas, Turkey

    Savaş Kaya

  6. Department of Chemistry, Sivas Cumhuriyet University Faculty of Science, Sivas, Turkey

    Dilara Özbakır Işın

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  1. Aljawhara H. Almuqrin
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  2. Jamelah S. Al-Otaibi
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Correspondence to Y. Sheena Mary.

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Almuqrin, A.H., Al-Otaibi, J.S., Mary, Y.S. et al. Spectral analysis and detailed quantum mechanical investigation of some acetanilide analogues and their self-assemblies with graphene and fullerene. J Mol Model 26, 254 (2020). https://doi.org/10.1007/s00894-020-04485-3

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