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Dual Chalcogen-Bonding Interactions for the Conformational Control of Urea
https://kyoto-phu.repo.nii.ac.jp/records/2000274
https://kyoto-phu.repo.nii.ac.jp/records/20002742d7b1499-8dd7-4aed-ada6-2aec26c1ebd0
| 名前 / ファイル | ライセンス | アクション |
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ChemEurJ_29_60_2023_inoue.pdf (7.7 MB)
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Supporting information for revision.pdf (24.2 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2025-12-12 | |||||
| タイトル | ||||||
| タイトル | Dual Chalcogen-Bonding Interactions for the Conformational Control of Urea | |||||
| 言語 | en | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 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 | |||||
| 著者 |
INOUE, Takumi
× INOUE, Takumi× OTA, Moe× AMIJIMA, Yui× TAKAHASHI, Haru× HAMADA, Shohei× NAKAMURA, Seikou× KOBAYASHI, Yusuke× SASAMORI, Takahiro× FURUTA, Takumi |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Dual chalcogen-bonding interactions is proposed as a novel means for the conformational control of urea derivatives. The formation of a chalcogen-bonding interaction at both sides of the urea carbonyl group was unambiguously confirmed by X-ray diffraction as well as computational studies including non-covalent interaction (NCI) plot index analysis, quantum theory of atoms in molecules (QTAIM) analysis, and natural bond orbital (NBO) analysis via DFT calculations. By virtue of this dual interaction, urea derivatives that bear chalcogen atoms (X=S and Se) adopt a planar structure via the carbonyl oxygen (O) with an X⋅⋅⋅O⋅⋅⋅X arrangement on the same side of the molecule. The rigidity of the conformational lock was evaluated using the molecular arrangement in the crystal and the rotational barrier of benzochalcogenophene ring, which indicated a stronger conformational lock in benzoselenophene than in benzothiophene urea derivatives. Furthermore, the acidity of the urea derivatives increases according to the Lewis-acidic properties of the chalcogen-bonding interactions, whereby benzoselenophene urea is more acidic than benzothiophene urea. Tweezer-shaped urea derivatives were prepared, and their stereostructure proved the viability of the conformational control for defining the location of the substituents on the urea framework. | |||||
| 言語 | en | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | chalcogen-bonding interaction | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | urea | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | conformational control | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | acidity | |||||
| キーワード | ||||||
| 主題Scheme | Other | |||||
| 主題 | tweezer-shaped molecule | |||||
| 書誌情報 |
en : Chemistry : a European journal. 巻 29, 号 60, p. e202302139, 発行日 2023-10-26 |
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| 出版者 | ||||||
| 出版者 | Wiley | |||||
| 言語 | en | |||||
| ISSN | ||||||
| 収録物識別子タイプ | PISSN | |||||
| 収録物識別子 | 0947-6539 | |||||
| PubMed番号 | ||||||
| 識別子タイプ | PMID | |||||
| 関連識別子 | 37507838 | |||||
| DOI | ||||||
| 関連タイプ | isVersionOf | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | https://doi.org/10.1002/chem.202302139 | |||||
| 権利 | ||||||
| 言語 | en | |||||
| 権利情報Resource | https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html | |||||
| 権利情報 | "This is the peer reviewed version of the following article: [Takumi Inoue, Moe Ota, Yui Amijima, Haru Takahashi, Shohei Hamada, Seikou Nakamura, Yusuke Kobayashi, Takahiro Sasamori, Takumi Furuta, Dual Chalcogen-Bonding Interactions for the Conformational Control of Urea. Chemistry : a European journal. 2023, e202302139.], which has been published in final form at [https://doi: 10.1002/chem.202302139]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited." | |||||
| 著者版フラグ | ||||||
| 出版タイプ | AM | |||||
| 出版タイプResource | http://purl.org/coar/version/c_ab4af688f83e57aa | |||||
