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Tautomerism of the antiepileptic drug Felbamate: A DFT study

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Abstract

The Felbamate is a novel anticonvulsant and neuropathic pain drug that can exist as three possible tautomers. Herein, employing density functional theory (DFT) and handling the solvent effects with the PCM model, the structural parameters, energy behavior, natural bond orbital analysis (NBO), as well as the tautomerism of Felbamate are investigated. F1 is the kinetically and thermodynamically most stable tautomer of Felbamate, which contains the amide group in each of the carbamate moieties. The calculated NMR chemical shifts and IR vibrational frequencies are in good agreement with the experimental values, confirming the suitability of the optimized geometry for Felbamate. The tautomerization reaction of F1 to each of the other tautomers occurs via an intramolecular proton transfer. This reaction affects considerably the structural parameters and atomic charges of the Felbamate molecule. A large HOMO-LUMO energy gap implies a high stability of the F1 tautomer.

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    A. Khaleghi-Rad, S. A. Beyramabadi, A. Morsali, M. Ebrahimi & M. Khorzandi-Chenarboo

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  1. A. Khaleghi-Rad
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  2. S. A. Beyramabadi
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  3. A. Morsali
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  4. M. Ebrahimi
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  5. M. Khorzandi-Chenarboo
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Corresponding author

Correspondence to S. A. Beyramabadi.

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Original Russian Text © 2017 A. Khaleghi-Rad, S. A. Beyramabadi, A. Morsali, M. Ebrahimi, M. Khorzandi-Chenarboo.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 58, No. 2, pp. 261–268, February–March, 2017.

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Khaleghi-Rad, A., Beyramabadi, S.A., Morsali, A. et al. Tautomerism of the antiepileptic drug Felbamate: A DFT study. J Struct Chem 58, 244–251 (2017). https://doi.org/10.1134/S0022476617020044

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  • DOI: https://doi.org/10.1134/S0022476617020044

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