Theoretical investigation on hydrogen bond interaction between adrenaline and hydrogen sulfide
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ORIGINAL PAPER
Theoretical investigation on hydrogen bond interaction between adrenaline and hydrogen sulfide Amr Mohamed 1 & Asmaa M. Fahim 2
&
Medhat A. Ibrahim 3
Received: 21 August 2020 / Accepted: 8 November 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract In this study, we elucidated the formation of hydrogen bond between adrenaline (AD) and hydrogen sulfide utilizing computational studies. Six potential complexes were studied including geometrical parameters, energy, vibrational frequency, topological analysis, natural bond orbital (NBO), quantum theory of atoms in molecules (QTAIM), and NMR analysis. Moreover, these calculations were examined through DFT/ωB97XD/6-311G++(d,p) level. It was found that there are no indication on formation on hydrogen bonding between the two catecholic OHs where the one formed between the amino group and the hydroxyl oxygen atom of adrenaline monomer was broken in AS1 to form two new interactions namely SH...N and O1H1...S, while it retained in other complexes. Furthermore, the bond became stronger due to cooperativity in AS3 and AS6, for the presence of withdrawing effect of the phenyl ring, the H-bonds formed with the side chain oxygen atom. The adrenaline and H2S interaction was experimentally examined via FT-IR spectrometry and thin layer chromatography for confirmation of our theoretical study. Keywords Adrenaline . H-bonding . Sulfide . ωB97XD/6-311G++(d,p) . NBO . FT-IR . QTAIM . NMR, GIAO, NCI, and RDG
Introduction Molecular modeling is a promising computational tool for elucidating the molecular structure of molecules especially those of biological origin [1–4]. It could be an effective tool also to be utilized alone to investigate biological molecules [5–7], while it can fulfill the molecular spectroscopic methods in other approaches [8–11]. Such a class of computational work is dedicated to studying important chemical as well as physical parameters of the molecules. Adrenaline (AD) which is also known as epinephrine is a hormone and neurotransmitter [12]. It is classified as a catecholamine type of neurotransmitters; it
* Asmaa M. Fahim [email protected] Medhat A. Ibrahim [email protected] 1
Qarun Petroleum Company, 1 Str., No 315, New Maadi, Cairo 11728, Egypt
2
Department of Green Chemistry, National Research Center, Dokki, Giza 12622, Egypt
3
Spectroscopy Department, National Research Centre, El-Buhouth Str., Dokki, Giza 12622, Egypt
is described as the emergency hormone which helps us to fight or run away from danger “fight or flight response” as described by Walter Cannon [13]. It is also having control over many physiological and biological processes depending on the receptor type. In some cases, it can be used as medication [14]. Studies of the gas phase structures of biomolecules provide an important connection to theoretical methods for modeling complex chemical structures because key features like conformational flexibility, intermolecular interactions pose major challenges to common spectroscopic techniques
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