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Studies on hydrogen bonding of adrenaline/acetone and adrenaline/methanol complexes: computational and experimental approach

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Abstract

In this investigation, we elucidate the potential interaction of volatile organic solvents such as acetone and ethanol with adrenaline hormone through hydrogen bonding. There are four potential complexes between adrenaline and acetone and six potential complexes between adrenaline and methanol, which were investigated from several perspectives such as energy, vibrational frequency, and natural bond orbital theory, quantum theory of atoms in molecules, nuclear magnetic resonance, reduced density gradient, and geometrical parameters, utilizing ωB97XD/6-311G++(d,p) level. Finally, the potential interaction was examined experimentally through FTIR which showed a remarkable redshift. The intramolecular H-bond was broken in the first complex forming a newly developed one, leading to structural deformation which in turn led to the destabilization of the developed complex, whereas that intramolecular H-bond was retained in the other three complexes of interest.

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Authors and Affiliations

  1. Qarun Petroleum Company, 1 Str., No 315, New Maadi, 11728 Maadi, Cairo, Egypt

    Amr Mohamed

  2. Department of Green Chemistry, National Research Center, Dokki, Giza, 12622, Egypt

    Asmaa M. Fahim

  3. Physics Department, Special Physics Branch, Faculty of Science, Ain Shams University, Cairo, 11566, Egypt

    Samah Abd Elhamead Ibrahim

  4. Spectroscopy Department, National Research Centre, El-Buhouth Str., 12622, Dokki, Giza, Egypt

    Medhat A. Ibrahim

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  1. Amr Mohamed
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Contributions

Dr. Amr Mohamed: Made theoretical calculation and wrote the manuscript.

Dr. Asmaa M Fahim: Revised the manuscript and elucidated all the manuscript.

Dr. Samah Abd Elhamead Ibrahim: Made theoretical results and made discussion.

Prof Dr Medhat A. Ibrahim: Made the idea of these studies and the principal author of this work and revised the manuscript and focus of results (supervision of this work).

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Correspondence to Asmaa M. Fahim.

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Mohamed, A., Fahim, A.M., Ibrahim, S.A.E. et al. Studies on hydrogen bonding of adrenaline/acetone and adrenaline/methanol complexes: computational and experimental approach. Struct Chem 32, 2115–2138 (2021). https://doi.org/10.1007/s11224-021-01773-3

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