Structure-reactivity relationship of piperidine nitroxide: Electrochemical, ESR and computational studies

Toshihide Yamasaki, Fumiya Mito, Yuko Ito, Sokkar Pandian, Yuichi Kinoshita, Koji Nakano, Ramachandran Murugesan, Kiyoshi Sakai, Hideo Utsumi, Ken Ichi Yamada

研究成果: ジャーナルへの寄稿学術誌査読

63 被引用数 (Scopus)

抄録

We have synthesized several nitroxides with different substituents which vary the steric and electronic environment around the N-O moiety and have systematically investigated the role of substituents on the stability of the radicals. Our results demonstrated the reactivity toward ascorbate correlates with the redox potential of the derivatives. Furthermore, ab initio calculations also indicated a correlation between the reduction rate and the computed singly occupied molecular orbital-lowest unoccupied molecular orbital energy gap, but not with solvent accessible surface area of the N-O moiety, supporting the experimental results and suggesting that the electronic factors largely determine the radicals' stability. Hence, it is possible to perform virtual screening of nitroxides to optimize their stability, which can help to rationally design novel nitroxides for their potential use in vivo.

本文言語英語
ページ(範囲)435-440
ページ数6
ジャーナルJournal of Organic Chemistry
76
2
DOI
出版ステータス出版済み - 1月 21 2011

!!!All Science Journal Classification (ASJC) codes

  • 有機化学

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