Electronic (donating or withdrawing) effects of ortho-phenolic substituents in dendritic antioxidants

Choon Young Lee, Charles Anamoah, Julius Semenya, Kelli N. Chapman, Allison N. Knoll, Hannah F. Brinkman, James I. Malone, Ajit Sharma

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

We report the first study on the electronic effects of ortho-substituents in dendritic antioxidants. Six antioxidants were designed to contain a common phenol ring to provide a baseline antioxidant activity, attached to two other phenol rings with H atoms (reference compound), electron donating groups (EDGs), or electron withdrawing groups (EWGs) ortho to the phenolic OH. These antioxidants were synthesized via reductive amination. Based on the DPPH assay, EDGs (o-OCH3) strongly enhanced while EWGs (o-NO2) significantly decreased the antioxidant activity. The halogens (o-Cl and o-Br) did not show any significant effect.

Original languageEnglish
Article number151607
JournalTetrahedron Letters
Volume61
Issue number11
DOIs
StatePublished - Mar 12 2020

Keywords

  • Antioxidant
  • DPPH
  • Dendrimer
  • Electronic effect

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