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Conformational Switch of Benzanilide Derivative Induced by Acid; Effect of Pentafluorobenzoyl Group

  • Ryu Yamasaki*
    Ryu Yamasaki
    Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
    *Email: [email protected]
    More by Ryu Yamasaki
  • Misuzu Harada
    Misuzu Harada
    Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
  • Rino Nagata
    Rino Nagata
    Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
    More by Rino Nagata
  • Ai Ito
    Ai Ito
    Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
    More by Ai Ito
  • Kazuo Fukuda
    Kazuo Fukuda
    Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
    More by Kazuo Fukuda
  • , and 
  • Iwao Okamoto
    Iwao Okamoto
    Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan
    More by Iwao Okamoto
Cite this: J. Org. Chem. 2022, 87, 13, 8469–8479
Publication Date (Web):June 8, 2022
https://doi.org/10.1021/acs.joc.2c00593
Copyright © 2022 American Chemical Society

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    Abstract

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    Amide-based molecular switches had its limitation on structural diversities. In this work, we designed and synthesized a series of pentafluorobenzoyl-based benzanilide compounds. The conformational ratio of these compounds in solution was correlated linearly with Hammett’s σp value of the substituent on the anilide ring, reflecting the repulsive interaction between the carbonyl group and the electron-rich aryl group. The addition of acid into the solution of 6, bearing pentafluorobenzoyl group, switched the stable amide conformation. In addition, the sizeable rotational barrier of 6 induced by the pentafluorobenzoyl moiety enabled us to monitor the conformational transition by means of 1H NMR spectroscopy.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.2c00593.

    • Crystal structure and parameter, NMR spectral (1H, 13C, 19F NMR), and VT-NMR and line shape analysis (PDF)

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    CCDC 21497832149789 and 2149792 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

    This article is cited by 5 publications.

    1. Ning Yu, Jing-Fang Lv, Shi-Mei He, Kui-Cheng He, Wei-Hao Zheng, Yu-Qiang Zhou, Kun Jiang, Xi-Chun Pan, Ye Wei. Modular Assembly of 2-Aminoaniline Derivatives by Merging Hydroxylamine-Passerini and Hetero-Cope Rearrangement. Organic Letters 2024, 26 (7) , 1358-1363. https://doi.org/10.1021/acs.orglett.3c04270
    2. Ryu Yamasaki, Mariko Ono, Kento Morita, Ai Ito, Kazuo Fukuda, Iwao Okamoto. Structures and Reactivities of N-Alkenyl-Substituted Anilides: The “Magic” Methyl Effect on Alkene. The Journal of Organic Chemistry 2023, 88 (20) , 14487-14493. https://doi.org/10.1021/acs.joc.3c01487
    3. Hongtao Zhao, Jonas Brånalt, Matthew Perry, Christian Tyrchan. The Role of Allylic Strain for Conformational Control in Medicinal Chemistry. Journal of Medicinal Chemistry 2023, 66 (12) , 7730-7755. https://doi.org/10.1021/acs.jmedchem.3c00446
    4. Anastasiya S. Soldatenko, Irina V. Sterkhova, Nataliya F. Lazareva. Synthesis and structure of N-(silylmethyl)benzanilides with SiC3OCl and SiC2OCl2 coordination units. Journal of Organometallic Chemistry 2023, 987-988 , 122634. https://doi.org/10.1016/j.jorganchem.2023.122634
    5. Ryu Yamasaki, Misuzu Harada, Ai Ito, Kazuo Fukuda, Shota Matsumoto, Satoru Karasawa, Iwao Okamoto. Reversible on/off conformational switching of pentafluorobenzoyl amide triggered by acid vapor and sublimation. CrystEngComm 2022, 24 (35) , 6226-6231. https://doi.org/10.1039/D2CE00972B

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