Hydroxyl radical induced transformation of phenylurea herbicides: A theoretical study

Viktória Mile, Ildikó Harsányi, Krisztina Kovács, Tamás Földes, Erzsébet Takács, L. Wojnárovits

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Aromatic ring hydroxylation reactions occurring during radiolysis of aqueous solutions are studied on the example of phenylurea herbicides by Density Functional Theory calculations. The effect of the aqueous media is taken into account by using the Solvation Model Based on Density model. Hydroxyl radical adds to the ring because the activation free energies (0.4–47.2 kJ mol−1) are low and also the Gibbs free energies have high negative values ((−27.4) to (−5.9) kJ mol−1). According to the calculations in most of cases the ortho- and para-addition is preferred in agreement with the experimental results. In these reactions hydroxycyclohexadienyl type radicals form. In a second type reaction, when loss of chlorine atom takes place, OH/Cl substitution occurs without cyclohexadienyl type intermediate.

Original languageEnglish
Pages (from-to)16-21
Number of pages6
JournalRadiation Physics and Chemistry
Volume132
DOIs
Publication statusPublished - Mar 1 2017

Keywords

  • Advanced oxidation processes
  • DFT calculations
  • Dehalogenation
  • Hydroxyl radical
  • Phenylurea herbicide
  • Radiolysis

ASJC Scopus subject areas

  • Radiation

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