Repozytorium

17O NMR and 15N NMR chemical shifts of sterically-hindered amides: ground-state destabilization in amide electrophilicity.

Autorzy

Vittorio Pace

Wolfgang Holzer

Laura Lelo

Shicheng Shi

Guangrong Meng

Mina Hanna

Roman Szostak

Michal Szostak

Rok wydania

2019

Czasopismo

Chemical Communications

Numer woluminu

55

Strony

4423-4426

DOI

10.1039/c9cc01402k

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

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

Strona internetowa wydawcy

https://www.rsc.org/

Podobne publikacje
2020

Electrophilicity scale of activated amides: 17O NMR and 15N NMR chemical shifts of acyclic twisted amides in N−C(O) cross‐coupling.

Ielo Laura, Pace Vittorio, Holzer Wolfgang, Rahman Md. Mahbubur, Meng Guangrong, Szostak Roman, Szostak Michal

2020

H/D isotope effects on 1H-NMR chemical Shifts in cyclic heterodimers and heterotrimers of phosphinic and phosphoric acids.

Mulloyarova Valeriia V., Ustimchuk Daria O., Filarowski Aleksander, Tolstoy Peter M.