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Hydrogen-Bond-Assisted, Concentration-Dependent Molecular Dimerization of Ferrocenyl Hydantoins

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    Hydrogen-Bond-Assisted, Concentration-Dependent Molecular Dimerization of Ferrocenyl Hydantoins
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    † Department of Chemical Sciences, University of Padova, via Marzolo 1, 35131 Padova, Italy
    ‡ Institute of Biomolecular Chemistry, Padova Unit, CNR, via Marzolo 1, 35131 Padova, Italy
    *E-mail for S.S.: [email protected]
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    Organometallics

    Cite this: Organometallics 2017, 36, 11, 2190–2197
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    https://doi.org/10.1021/acs.organomet.7b00248
    Published May 18, 2017
    Copyright © 2017 American Chemical Society
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    Abstract

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    The synthesis and characterization of the ferrocenyl methylhydantoin 5-ferrocenyl-5-methylimidazolidine-2,4-dione, efficiently prepared through a Bucherer–Bergs reaction, and its derivatives carrying tert-butoxycarbonyl (Boc) protecting groups, namely 1,3-bis(tert-butoxycarbonyl)-5-ferrocenyl-5-methylimidazolidine-2,4-dione and 1-(tert-butoxycarbonyl)-5-ferrocenyl-5-methylimidazolidine-2,4-dione, are reported. X-ray diffraction and ESI-mass spectrometry analyses of the ferrocenyl methylhydantoin revealed the presence of C═O···H–N intermolecularly hydrogen-bonded dimers. The mono-Boc derivative formed a hydrogen-bonded dimer in solution, as confirmed by 1H NMR, FT-IR, and cyclic voltammetry experiments at different concentrations in CDCl3 or CHCl3.

    Copyright © 2017 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.organomet.7b00248.

    • Crystal data and structure refinement details for 1 and 2, NMR and ESI spectra of 1–3, and CVs of 3 at different concentrations and scan rates (PDF)

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    CCDC 1531458–1531459 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

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    This article is cited by 7 publications.

    1. Ivette Morales-Salazar, Jean-Philippe Bouillon, Eduardo González-Zamora, Alejandro Islas-Jácome. Non-Isocyanide-Based Three-Component Reactions: From Strecker to Nowadays. Journal of the Mexican Chemical Society 2025, 69 (1) , 185-258. https://doi.org/10.29356/jmcs.v69i1.2301
    2. Jie Jack Li. Bucherer-Bergs-Reaktion. 2024, 58-60. https://doi.org/10.1007/978-3-031-52850-7_18
    3. Juanjuan Li, Yuqing Shi, Tao Cheng. Electronic coupling and electron transfer in hydrogen-bonded mixed-valence compounds. Physical Chemistry Chemical Physics 2023, 25 (24) , 16201-16211. https://doi.org/10.1039/D3CP01337E
    4. Zijie Zhou, Yixin Guo, Xiangmei Kong, Ying Wang, Tianfei Liu. Control of Electron Coupling and Electron Transfer Through Non‐covalent Interactions in Mixed‐Valence Systems. 2023, 349-363. https://doi.org/10.1002/9783527835287.ch11
    5. Martin Kalník, Peter Gabko, Maroš Bella, Miroslav Koóš. The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity. Molecules 2021, 26 (13) , 4024. https://doi.org/10.3390/molecules26134024
    6. Jie Jack Li. Bucherer–Bergs Reaction. 2021, 53-55. https://doi.org/10.1007/978-3-030-50865-4_18
    7. Tulasi Barik, Avishek Ghosh, Abtar Mishra, Rohan Dhiman, Takahiro Sasamori, Saurav Chatterjee. Bioactive 1,1′-unsymmetrical bi-functional ferrocenyl compounds using a novel solvent free one pot multicomponent reaction method. Journal of Organometallic Chemistry 2020, 908 , 121095. https://doi.org/10.1016/j.jorganchem.2019.121095
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    Organometallics

    Cite this: Organometallics 2017, 36, 11, 2190–2197
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.organomet.7b00248
    Published May 18, 2017
    Copyright © 2017 American Chemical Society
    Request reuse permissions

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