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17O NMR and 15N NMR chemical shifts of sterically-hindered amides: ground-state destabilization in amide electrophilicity.
Autorzy
Rok wydania
2019
Czasopismo
Numer woluminu
55
Strony
4423-4426
DOI
10.1039/c9cc01402k
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The structure and spectroscopic properties of the amide bond are a topic of fundamental interest in chemistry and biology. Herein, we report 17O NMR and 15N NMR spectroscopic data for four series of sterically-hindered acyclic amides. Despite the utility of 17O NMR and 15N NMR spectroscopy, these methods are severely underutilized in the experimental determination of electronic properties of the amide bond. The data demonstrate that a combined use of 17O NMR and 15N NMR serves as a powerful tool in assessing electronic effects of the amide bond substitution as a measure of electrophilicity of the amide bond. Notably, we demonstrate that steric destabilization of the amide bond results in electronically-activated amides that are comparable in terms of electrophilicity to acyl fluorides and carboxylic acid anhydrides.
Adres publiczny
http://dx.doi.org/10.1039/c9cc01402k
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