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Norcorrole: Aromaticity and Antiaromaticity in Contest

Cite this: Org. Lett. 2020, 22, 21, 8676–8680
Publication Date (Web):October 26, 2020
https://doi.org/10.1021/acs.orglett.0c03254
Copyright © 2020 American Chemical Society

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    Abstract

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    Magnetic shielding studies demonstrate that nickel norcorrole (NiNc) and norcorrole (H2Nc) provide unusual examples of stable molecules with high antagonistic levels of antiaromaticity and aromaticity: Both incorporate an antiaromatic “core”, a 14-membered cyclic conjugated subsystem with 16 π electrons, surrounded by an aromatic “halo” in the form of a ring of either 14 atoms and 14 π electrons with a new type of homoconjugation (NiNc), or 18 atoms with 18 π electrons (H2Nc).

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.0c03254.

    • Bond lengths in the local minimum geometries of NiNc and H2Nc; NPA charges for NiNc and H2Nc; NICS values and isotropic shieldings for benzene, cyclobutadiene, NiNc and H2Nc; computational details including optimized geometries; additional references (PDF)

    • Zip archive of Gaussian cube files with isotropic shielding values for benzene, cyclobutadiene, NiNc, and H2Nc (ZIP)

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    Cited By

    This article is cited by 12 publications.

    1. Peter B. Karadakov, Muntadar A. H. Al-Yassiri. Excited-State Aromaticity Reversals in Naphthalene and Anthracene. The Journal of Physical Chemistry A 2023, 127 (14) , 3148-3162. https://doi.org/10.1021/acs.jpca.3c00485
    2. Peter B. Karadakov. How Different are the Diamagnetic and Paramagnetic Contributions to Off‐Nucleus Shielding in Aromatic and Antiaromatic Rings?. ChemPhysChem 2023, 24 (9) https://doi.org/10.1002/cphc.202300038
    3. Peter B. Karadakov, Tom Riley. The Effect of Hydrogenation on the Contest between Aromaticity and Antiaromaticity in Norcorrole. Chemistry – A European Journal 2023, 29 (12) https://doi.org/10.1002/chem.202203400
    4. Peter B. Karadakov. Off-nucleus magnetic shielding: Theory and applications. 2022, 95-131. https://doi.org/10.1016/bs.arnmr.2022.07.001
    5. Peter B. Karadakov, Nicholas Preston. Aromaticity reversals and their effect on bonding in the low-lying electronic states of cyclooctatetraene. Physical Chemistry Chemical Physics 2021, 23 (43) , 24750-24756. https://doi.org/10.1039/D1CP04394C
    6. Michael Mauksch, Svetlana B. Tsogoeva. Disclosure of Ground‐State Zimmerman‐Möbius Aromaticity in the Radical Anion of [6]Helicene and Evidence for 4π Periodic Aromatic Ring Currents in a Molecular “Metallic” Möbius Strip. Chemistry – A European Journal 2021, 27 (59) , 14660-14671. https://doi.org/10.1002/chem.202102230
    7. Peter B. Karadakov, Brett VanVeller. Magnetic shielding paints an accurate and easy-to-visualize portrait of aromaticity. Chemical Communications 2021, 57 (75) , 9504-9513. https://doi.org/10.1039/D1CC03701C
    8. Jens Krumsieck, Martin Bröring. PorphyStruct : A Digital Tool for the Quantitative Assignment of Non‐Planar Distortion Modes in Four‐Membered Porphyrinoids. Chemistry – A European Journal 2021, 27 (45) , 11580-11588. https://doi.org/10.1002/chem.202101243
    9. Sha Li, Oskar Smaga, Yahan Sun, Xiaofang Li, Miłosz Pawlicki, Marzena Sukniewicz, Piotr J. Chmielewski. Friedel–Crafts acylation of antiaromatic norcorroles: electronic and steric modulation of the paratropic current. Organic Chemistry Frontiers 2021, 8 (14) , 3639-3652. https://doi.org/10.1039/D1QO00621E
    10. Felix Plasser, Florian Glöcklhofer. Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity**. European Journal of Organic Chemistry 2021, 2021 (17) , 2529-2539. https://doi.org/10.1002/ejoc.202100352
    11. Jiří Czernek, Jiří Brus. A Volumetric Analysis of the 1H NMR Chemical Shielding in Supramolecular Systems. International Journal of Molecular Sciences 2021, 22 (7) , 3333. https://doi.org/10.3390/ijms22073333
    12. Albert Artigas, Denis Hagebaum-Reignier, Yannick Carissan, Yoann Coquerel. Visualizing electron delocalization in contorted polycyclic aromatic hydrocarbons. Chemical Science 2021, 115 https://doi.org/10.1039/D1SC03368A

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