Predicting the Adsorption of Amoxicillin and Ibuprofen on Chitosan and Graphene Oxide Materials: A Density Functional Theory Study

Abstract

The occurrence, persistence, and accumulation of antibiotics and non-steroidal anti-inflammatory drugs (NSAIDs) represent a new environmental problem due to their harmful effects on human and aquatic life. A suitable absorbent for a particular type of pollutant does not necessarily absorb other types of compounds, so knowing the compatibility between a particular pollutant and a potential absorbent before experimentation seems to be fundamental. In this work, the molecular interactions between some pharmaceuticals (amoxicillin, ibuprofen, and tetracycline derivatives) with two potential absorbers, chitosan and graphene oxide models (pyrene, GO-1, and coronene, GO-2), were studied using the ωB97X-D/6-311G(2d,p) level of theory. The energetic interaction order found was amoxicillin/chitosan > amoxicillin/GO-1 > amoxicillin/GO-2 > ibuprofen/chitosan > ibuprofen/GO-2 > ibuprofen/GO-1, the negative sign for the interaction energy in all complex formations confirms good compatibility, while the size of Eint between 24–34 kcal/mol indicates physisorption processes. moreover, the free energies of complex formation were negative, confirming the spontaneity of the processes. The larger interaction of amoxicillin GOs, compared to ibuprofen GOs, is consistent with previously reported experimental results, demonstrating the exceptional predictability of these methods. The second-order perturbation theory analysis shows that the amoxicillin complexes are mainly driven by hydrogen bonds, while van der Waals interactions with chitosan and hydrophobic interactions with graphene oxides are modelled for the ibuprofen complexes. Energy decomposition analysis (EDA) shows that electrostatic energy is a major contributor to the stabilization energy in all cases. The results obtained in this work promote the use of graphene oxides and chitosan as potential adsorbents for the removal of these emerging pollutants from water.

DFT Study of Chitosan Ascorbate Nanoparticles Structure

“…ΔG aq values are in the order: CS-AA (-3.37 kcal/mol) < CS-TPP (-3.08 kcal/mol). This demonstrates the influence of solvent polarity on the parameter and the large role of thermodynamic driving forces in the aqueous phase, also for other systems [16,[38][39][40][41][42][43][44].…”

Removal of ibuprofen and amoxicillin in domestic wastewater using activated carbon soaps and moringa seed powder at the laboratory level

“…Ciesielczyk et al (2019) informaron que la interacción electrostática se debe principalmente a los enlaces químicos formados entre los grupos funcionales cargados positivamente de un adsorbente y las moléculas de ibuprofeno cargadas negativamente. Anchique et al,(2021) afirma que "un absorbente adecuado para un tipo particular de contaminante no necesariamente absorbe otros tipos de compuestos, por lo que conocer la compatibilidad entre un contaminante particular y un absorbente potencial antes de la experimentación parece ser fundamental", después de realizar una investigación de adsorción de amoxicilina e ibuprofeno con los adsorbentes quitosano y oxido de grafeno, en sus resultados reporta diferencia en la adsorción de ambos fármacos donde los complejos de amoxicilina están impulsados principalmente por enlaces de hidrógeno, mientras que las interacciones de Van der Waals con el quitosano y las interacciones hidrofóbicas con los óxidos de grafeno se modelan para los complejos de ibuprofeno.…”

Influence of β-Cyclodextrin Methylation on Host-Guest Complex Stability: A Theoretical Study of Intra- and Intermolecular Interactions as Well as Host Dimer Formation

“…The ΔΕ int-FF was calculated as the sum of the electrostatic interaction energy (ΔΕ ele ) and the vdW interaction energy (ΔΕ vdW ) using the potential of pairwise non-covalent interactions (Equations (3) and (4)) [ 61 ]. …”