Probing molecular interactions, electronic properties, and reactivity of monoamine neurotransmitters in different protonation states via quantum chemical investigation

Yousif Hussein Azeez; Khdir Ahmed Othman; Rebaz Anwar Omer; Aryan Fathulla Qader

doi:10.17308/kcmf.2024.26/12214

Yousif Hussein Azeez University of Halabja, College of Science, Department of Physics, Halabja, Iraq https://orcid.org/0000-0001-5357-7856
Khdir Ahmed Othman Department of Chemistry, Faculty of Science and Health, Koya University, Danielle Mitterrand Boulevard, Koya KOY45, Kurdistan Region – F.R., Iraq https://orcid.org/0000-0002-7763-2976
Rebaz Anwar Omer Department of Chemistry, Faculty of Science and Health, Koya University, Danielle Mitterrand Boulevard, Koya KOY45, Kurdistan Region – F.R., Iraq; Knowledge University, College of Pharmacy, Department of Pharmacy, Erbil 44001, Iraq https://orcid.org/0000-0002-3774-6071
Aryan Fathulla Qader Qader Department of Chemistry, Faculty of Science and Health, Koya University, Danielle Mitterrand Boulevard, Koya KOY45, Kurdistan Region – F.R., Iraq https://orcid.org/0000-0002-2547-7708

DOI: https://doi.org/10.17308/kcmf.2024.26/12214

Keywords: Quantum chemistry, Molecular interactions, Monoamine neurotransmitters, electronic properties and Protonation states

Abstract

Amphetamine, dopamine, norepinephrine, serotonin, and tryptamine are a group of monoamine neurotransmitters that regulate diverse brain functions. This work examined these compounds’ neutral, protonated, and deprotonated, structural, energetic, and optical properties using quantum chemistry methods. Noncovalent interactions (NCI) and reduced density gradient (RDG) investigations revealed weak intermolecular forces and electron density distribution. The RDG values were observed to span from 0.12 to 0.43, indicating varying degrees of repulsion or attraction. The hydrogen bonding patterns and their strength and nature were also investigated using the Atoms in Molecules (AIM) and B3LYP methods. The
quantification was done using —^2 r(r), H(r), and energy density values, which showed a variation from -0.014 to 0.026 Hartree/Bohr3, reflecting covalent or electrostatic interactions. A comparison was made between the compounds based on their physical and chemical attributes, such as polar surface area (ranging from 41.81 to 86.71 Å²), rotatable bonds (which were identical), and proton affinity (a measure of stability). Lewis structures and natural bond orbital (NBO) analysis showed resonance and electron delocalization. The study also examined their molecular orbitals (MOs) and found that protonation and deprotonation could significantly change their electronic characteristics, including the energies of the highest occupied
(HOMO) and lowest unoccupied (LUMO), the energy gap, and the shape and size of their lobes. The nonlinear optical properties were also assessed, affected by polarizability and hyperpolarizability indices, ranging from 2.267 a.u. (Dopamine) to 7.891 a.u. (Protonated Serotonin). These properties pointed to the applications of these compounds in optical devices

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Author Biographies

Yousif Hussein Azeez, University of Halabja, College of Science, Department of Physics, Halabja, Iraq

MSc in Advanced Materials Science, Lecturer at the Department of physics, Halabja University (Iraq)

Khdir Ahmed Othman, Department of Chemistry, Faculty of Science and Health, Koya University, Danielle Mitterrand Boulevard, Koya KOY45, Kurdistan Region – F.R., Iraq

MSc In Organic Chemistry, Lecturer at the Department of Chemistry, Faculty of Science and Health, Koya University, (Kurdistan Region – F.R., Iraq)

Rebaz Anwar Omer, Department of Chemistry, Faculty of Science and Health, Koya University, Danielle Mitterrand Boulevard, Koya KOY45, Kurdistan Region – F.R., Iraq; Knowledge University, College of Pharmacy, Department of Pharmacy, Erbil 44001, Iraq

PhD in Organic Chemistry,
Head of Chemistry Department, Faculty of Science and
Health, Koya University (Kurdistan Region – F.R., Iraq),
Department of Pharmacy, College of Pharmacy,
Knowledge University (Erbil, Iraq)

Aryan Fathulla Qader, Qader Department of Chemistry, Faculty of Science and Health, Koya University, Danielle Mitterrand Boulevard, Koya KOY45, Kurdistan Region – F.R., Iraq

PhD in Analytical Chemistry,
Lecturer at the Departmet of Chemistry, Faculty of
Science and Health, Koya University (Kurdistan
Region – F.R., Iraq)

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