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Synthesis and Structural Properties of Adamantane‐Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety
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 BH(3) ⋅ THF. The obtained...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9535505/ https://www.ncbi.nlm.nih.gov/pubmed/35243816 http://dx.doi.org/10.1002/open.202200031 |
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author | Bonsir, Maxime Kennedy, Alan R. Geerts, Yves |
author_facet | Bonsir, Maxime Kennedy, Alan R. Geerts, Yves |
author_sort | Bonsir, Maxime |
collection | PubMed |
description | 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 BH(3) ⋅ 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)=11.5–13.3 kcal ⋅ mol(−1)). |
format | Online Article Text |
id | pubmed-9535505 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-95355052022-10-12 Synthesis and Structural Properties of Adamantane‐Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety Bonsir, Maxime Kennedy, Alan R. Geerts, Yves ChemistryOpen Research Articles 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 BH(3) ⋅ 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)=11.5–13.3 kcal ⋅ mol(−1)). John Wiley and Sons Inc. 2022-03-04 /pmc/articles/PMC9535505/ /pubmed/35243816 http://dx.doi.org/10.1002/open.202200031 Text en © 2022 The Authors. Published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Research Articles Bonsir, Maxime Kennedy, Alan R. Geerts, Yves Synthesis and Structural Properties of Adamantane‐Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety |
title | Synthesis and Structural Properties of Adamantane‐Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety |
title_full | Synthesis and Structural Properties of Adamantane‐Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety |
title_fullStr | Synthesis and Structural Properties of Adamantane‐Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety |
title_full_unstemmed | Synthesis and Structural Properties of Adamantane‐Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety |
title_short | Synthesis and Structural Properties of Adamantane‐Substituted Amines and Amides Containing an Additional Adamantane, Azaadamantane or Diamantane Moiety |
title_sort | synthesis and structural properties of adamantane‐substituted amines and amides containing an additional adamantane, azaadamantane or diamantane moiety |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9535505/ https://www.ncbi.nlm.nih.gov/pubmed/35243816 http://dx.doi.org/10.1002/open.202200031 |
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