Synthesis and structural properties of adamantane-substituted amines and amides containing an additional adamantane, azaadamantane or diamantane moiety
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: https://orcid.org/0000-0003-3652-6015 and Geerts, Yves;-
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Item type: Article ID code: 79840 Dates: DateEvent4 March 2022Published4 March 2022Published Online11 February 2022AcceptedSubjects: 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