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- Toshifumi Kobayashi
- Faculty of Pharmacy Keio University 1-5-30 Shibakoen Minato-ku Tokyo 105-8512 Japan
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- Fumitaka Ishiwari
- Laboratory for Chemistry and Life Science Institute of Innovative Research Tokyo Institute of Technology 4259 Nagatsuta, Midori-ku Yokohama 226-8503 Japan
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- Takanori Fukushima
- Laboratory for Chemistry and Life Science Institute of Innovative Research Tokyo Institute of Technology 4259 Nagatsuta, Midori-ku Yokohama 226-8503 Japan
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- Yuki Nojima
- Department of Chemistry Graduate School of Science Kitasato University 1-15-1 Kitasato Minami-ku Sagamihara Kanagawa 252-0373 Japan
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- Masashi Hasegawa
- Department of Chemistry Graduate School of Science Kitasato University 1-15-1 Kitasato Minami-ku Sagamihara Kanagawa 252-0373 Japan
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- Yasuhiro Mazaki
- Department of Chemistry Graduate School of Science Kitasato University 1-15-1 Kitasato Minami-ku Sagamihara Kanagawa 252-0373 Japan
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- Kengo Hanaya
- Faculty of Pharmacy Keio University 1-5-30 Shibakoen Minato-ku Tokyo 105-8512 Japan
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- Takeshi Sugai
- Faculty of Pharmacy Keio University 1-5-30 Shibakoen Minato-ku Tokyo 105-8512 Japan
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- Shuhei Higashibayashi
- Faculty of Pharmacy Keio University 1-5-30 Shibakoen Minato-ku Tokyo 105-8512 Japan
書誌事項
- 公開日
- 2023-06-23
- 資源種別
- journal article
- 権利情報
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- http://creativecommons.org/licenses/by-nc-nd/4.0/
- DOI
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- 10.1002/chem.202301466
- 公開者
- Wiley
この論文をさがす
説明
<jats:title>Abstract</jats:title><jats:p>1,1’,10,10’‐Biphenothiazine and its <jats:italic>S</jats:italic>,<jats:italic>S</jats:italic>,<jats:italic>S</jats:italic>’,<jats:italic>S</jats:italic>’‐tetroxide are diaza[5]helicenes with N−N linkages. Kinetic experiments on racemization together with DFT calculations revealed that they undergo inversion through the N−N bond breaking pathway rather than the general conformational pathway. In these diaza[5]helicenes with this inversion mechanism, the reduction of electronic repulsion in the N−N bond by modification of S to SO<jats:sub>2</jats:sub> at the outer position of the helix led to a significantly higher inversion barrier, 35.3 kcal/mol, compared to [5]helicene. 1,1’,10,10’‐Biphenothiazine <jats:italic>S</jats:italic>,<jats:italic>S</jats:italic>,<jats:italic>S</jats:italic>’,<jats:italic>S</jats:italic>’‐tetroxide was highly resistant to acid‐mediated N−N bond breaking and racemization under acidic conditions.</jats:p>
収録刊行物
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- Chemistry – A European Journal
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Chemistry – A European Journal 29 (43), 2023-06-23
Wiley
