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Molecular Simulation of Enantiodifferentiating Photoisomerization of Cyclooctene by Chiral Sensitizers
http://hdl.handle.net/10232/0002000530
http://hdl.handle.net/10232/00020005309032d184-a020-44a7-8bc2-3f3637b024b6
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
7_135 (742.3 KB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2024-10-24 | |||||
| タイトル | ||||||
| タイトル | Molecular Simulation of Enantiodifferentiating Photoisomerization of Cyclooctene by Chiral Sensitizers | |||||
| タイトル言語 | en | |||||
| 著者 |
Hashimoto, Hiromitsu
× Hashimoto, Hiromitsu× 下茂, 徹朗× Atsuchi, Mikito× 満塩, 勝× 染川, 賢一 |
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| 言語 | ||||||
| 言語 | eng | |||||
| キーワード | ||||||
| 主題言語 | en | |||||
| 主題Scheme | Other | |||||
| 主題 | Molecular simulation | |||||
| キーワード | ||||||
| 主題言語 | en | |||||
| 主題Scheme | Other | |||||
| 主題 | PM5 | |||||
| キーワード | ||||||
| 主題言語 | en | |||||
| 主題Scheme | Other | |||||
| 主題 | Enantiodifferentiation | |||||
| キーワード | ||||||
| 主題言語 | en | |||||
| 主題Scheme | Other | |||||
| 主題 | Photoisomerization | |||||
| キーワード | ||||||
| 主題言語 | en | |||||
| 主題Scheme | Other | |||||
| 主題 | Cyclooctene | |||||
| キーワード | ||||||
| 主題言語 | en | |||||
| 主題Scheme | Other | |||||
| 主題 | Chiral sensitizer | |||||
| キーワード | ||||||
| 主題言語 | en | |||||
| 主題Scheme | Other | |||||
| 主題 | Benzenepolycarboxylate | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| アクセス権 | ||||||
| アクセス権 | open access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_abf2 | |||||
| 要約 | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | For theoretical study on interesting enantiodifferenciating photoisomerization of (Z)-cyclooctene (1Z) to (E)-cyclooctene (1E) by chiral benzenepolycarboxylates (2a) in solution, the profiles of energy and stereochemical change of the sensitized photoisomerization were inferred by molecular simulation by use of MOPAC-PM5 method. The energy, stereochemical change and equilibrium of the ground states and excited singlet states of 1Z, 1E, tetramethyl 1,2,4,5-benzenetetracarboxylate (2b), dimethyl 3,5-bis(trifluoromethyl)benzoate (2c), and (R)- and (S)-dimenthyl 3,5-bis(trifluoromethyl)benzoate (2dr and 2ds) as a chiral model of 2a were first interpreted. 1Z has an asymmetric conformer and the isomerization to (R)- or (S)-1E may be dependent on preferential one-side rotation. Inferred exciplexes (Ex1) such as 1Z·2b* (2b*: excited singlet state of 2b) occur via energy transfers through some interactions to bring the next loose exciplexes (Ex2) such as 1E*·2b, which give 1E at the respective 1E/1Z ratio. The Ex1 and Ex2 structures were inferred to possess proper π*/π and C-H/π interactions, ester C=O/HC (olefin and allyl) and F/H hydrogen bondings, placed in parallel or alongside depending on the substituents. The photoisomerization may depend on the energy difference between the two exciplexes, and the transition state (TS) energy. The carbonyl groups and π components on the enantiomeric polycarboxylates make selective hydrogen bondings, π*/π and CH/π interactions with the olefin and allyl groups on asymmetric 1Z, and bring diastereomeric Ex1. Those interaction accumulations are inferred to bring enantiodifferentiating energy transfer by one-side rotation (asymmetric environment) of the two molecules for (R)-1E or (S)-1E like enzymes. |
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| 内容記述言語 | en | |||||
| 収録雑誌名 |
en : Journal of Computer Chemistry, Japan 巻 7, 号 4, p. 135-142, 発行日 2008-12-15 |
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| 作成日 | ||||||
| 日付 | 2008-12-15 | |||||
| 日付タイプ | Issued | |||||
| ISSN | ||||||
| 収録物識別子タイプ | EISSN | |||||
| ISSN | 13473824 | |||||
| NII書誌ID（雑誌） | ||||||
| 収録物識別子タイプ | NCID | |||||
| NC ID | AA11657986 | |||||
| DOI | ||||||
| 識別子タイプ | DOI | |||||
| DOI | https://doi.org/10.2477/jccj.H2009 | |||||
| 権利 | ||||||
| 権利情報の言語 | en | |||||
| 権利情報 | (c) 2008 Society of Computer Chemistry, Japan | |||||
| 出版タイプ | ||||||
| 出版タイプ | VoR | |||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
| 公開者・出版者 | ||||||
| 出版者 | 日本コンピュータ化学会 | |||||
| 出版者言語 | ja | |||||
