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

doi:10.1016/j.tetlet.2020.151607

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

Choon Young Lee, Charles Anamoah + Show 6 more

https://doi.org/10.1016/j.tetlet.2020.151607

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Journal: Tetrahedron Letters	Publication Date: Jan 10, 2020
Citations: 11

Affiliation: Central Michigan University

#Electron Donating Groups #Electron Withdrawing Groups + Show 8 more

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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.

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