Theoretical analysis of naproxen reaction with sulfate and hydroxyl radicals in the aqueous phase: Investigating reactive sites and reaction kinetics.

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  • Additional Information
    • Source:
      Publisher: Elsevier Science Ltd Country of Publication: England NLM ID: 0320657 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1879-1298 (Electronic) Linking ISSN: 00456535 NLM ISO Abbreviation: Chemosphere Subsets: MEDLINE
    • Publication Information:
      Publication: Oxford : Elsevier Science Ltd
      Original Publication: Oxford, New York, : Pergamon Press.
    • Subject Terms:
      Naproxen*/chemistry ; Hydroxyl Radical*/chemistry ; Thermodynamics* ; Sulfates*/chemistry; Kinetics ; Water/chemistry ; Models, Chemical
    • Abstract:
      In this study, we have utilized theoretical calculations to predict the reaction active sites of naproxen when reacting with radicals and to further study the thermodynamics and kinetics of the reactions with ·OH and SO 4 -· . The evidence, derived from the average local ionization energy and electrostatic potential, points to the naphthalene ring as the preferred site of attack, especially for the C2, C6, C9, and C10 sites. The changes in Gibbs free energy and enthalpy of the reactions initiated by ·OH and SO 4 -· ranged between -19.6 kcal/mol - 26.3 kcal/mol and -22.3 kcal/mol -18.5 kcal/mol, respectively. More in-depth investigation revealed that RA2 pathway for ·OH exhibited the lowest free energy of activation, suggesting this reaction is more inclined to proceed. The second-order rate constant results indicate the ·OH attacking reaction is faster than reactions initiated by SO 4 ·- , yet controlled by diffusion. The consistency between theoretical findings and experimental data underscores the validity of this computational method for our study.
      Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
      (Copyright © 2024 Elsevier Ltd. All rights reserved.)
    • Contributed Indexing:
      Keywords: Naproxen; Quantum chemistry calculations; Reaction mechanisms; Reactive sites
    • Accession Number:
      57Y76R9ATQ (Naproxen)
      3352-57-6 (Hydroxyl Radical)
      0 (Sulfates)
      059QF0KO0R (Water)
    • Publication Date:
      Date Created: 20240801 Date Completed: 20240820 Latest Revision: 20240820
    • Publication Date:
      20240820
    • Accession Number:
      10.1016/j.chemosphere.2024.142953
    • Accession Number:
      39089337