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, Julius Semenya, Kelli N. Chapman, Allison N. Knoll, Hannah F. Brinkman, James I. Malone, Ajit Sharma

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

6 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 language	English
Article number	151607
Journal	Tetrahedron Letters
Volume	61
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2020.151607
State	Published - Mar 12 2020

Keywords

Antioxidant
DPPH
Dendrimer
Electronic effect

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10.1016/j.tetlet.2020.151607

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title = "Electronic (donating or withdrawing) effects of ortho-phenolic substituents in dendritic antioxidants",

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.",

keywords = "Antioxidant, DPPH, Dendrimer, Electronic effect",

author = "Lee, {Choon Young} and Charles Anamoah and Julius Semenya and Chapman, {Kelli N.} and Knoll, {Allison N.} and Brinkman, {Hannah F.} and Malone, {James I.} and Ajit Sharma",

note = "Funding Information: We are grateful to the Central Michigan University Office of Research and Sponsored Programs and Department of Chemistry and Biochemistry for funding. Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

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journal = "Tetrahedron Letters",

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T1 - Electronic (donating or withdrawing) effects of ortho-phenolic substituents in dendritic antioxidants

AU - Lee, Choon Young

AU - Anamoah, Charles

AU - Semenya, Julius

AU - Chapman, Kelli N.

AU - Knoll, Allison N.

AU - Brinkman, Hannah F.

AU - Malone, James I.

AU - Sharma, Ajit

N1 - Funding Information: We are grateful to the Central Michigan University Office of Research and Sponsored Programs and Department of Chemistry and Biochemistry for funding. Publisher Copyright: © 2020 Elsevier Ltd

PY - 2020/3/12

Y1 - 2020/3/12

N2 - 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.

AB - 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.

KW - Antioxidant

KW - DPPH

KW - Dendrimer

KW - Electronic effect

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DO - 10.1016/j.tetlet.2020.151607

M3 - Article

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VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 11

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ER -

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

Abstract

Keywords

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