Synthesis and structural properties of adamantane-substituted amines and amides containing an additional adamantane, azaadamantane or diamantane moiety

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Bonsir, Maxime and Kennedy, Alan R. and Geerts, Yves (2022) Synthesis and structural properties of adamantane-substituted amines and amides containing an additional adamantane, azaadamantane or diamantane moiety. ChemistryOpen, 11 (10). e202200031. ISSN 2191-1363 (https://doi.org/10.1002/open.202200031)

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Abstract

Introduction of adamantane moieties on diamondoids such as adamantane, 2-azaadamantane or diamantane by amide formation and reduction to the corresponding amine was performed in a straightforward and easy way by amidation under Schotten–Baumann conditions and reduction with BH3·THF. The obtained amides and amines were studied in terms of structural properties towards the perspective of transformation into nanodiamonds. Crystal structure and dynamic NMR experiments of the most crowded amide obtained gave structural insights into the effect of bulkiness and steric strain on out-of-planarity of amide bonds(16.0°) and the kinetics and thermodynamics of amide bond rotation (ΔG≠298K=11.5–13.3kcal·mol1).

ORCID iDs

Bonsir, Maxime, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Geerts, Yves;
  • Item type:Article
    ID code:79840
    Dates:
    Date
    Event
    4 March 2022
    Published
    4 March 2022
    Published Online
    11 February 2022
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:08 Mar 2022 13:52
    Last modified:02 Dec 2024 01:26
    URI:https://strathprints.strath.ac.uk/id/eprint/79840
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