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

Vittorio Pace, Wolfgang Holzer, Laura Ielo, Shicheng Shi, Guangrong Meng, Mina Hanna, Roman Szostak, Michal Szostak

Research output: Contribution to journalArticle

Abstract

The structure and spectroscopic properties of the amide bond are a topic of fundamental interest in chemistry and biology. Herein, we report 17 O NMR and 15 N NMR spectroscopic data for four series of sterically-hindered acyclic amides. Despite the utility of 17 O NMR and 15 N 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 17 O NMR and 15 N 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.

Original languageEnglish (US)
Pages (from-to)4423-4426
Number of pages4
JournalChemical Communications
Volume55
Issue number30
DOIs
StatePublished - Jan 1 2019

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Chemical shift
Amides
Ground state
Nuclear magnetic resonance
Anhydrides
Carboxylic Acids
Fluorides
Carboxylic acids
Electronic properties
Nuclear magnetic resonance spectroscopy
Substitution reactions

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Pace, Vittorio ; Holzer, Wolfgang ; Ielo, Laura ; Shi, Shicheng ; Meng, Guangrong ; Hanna, Mina ; Szostak, Roman ; Szostak, Michal. / 17 O NMR and 15 N NMR chemical shifts of sterically-hindered amides : Ground-state destabilization in amide electrophilicity. In: Chemical Communications. 2019 ; Vol. 55, No. 30. pp. 4423-4426.
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17 O NMR and 15 N NMR chemical shifts of sterically-hindered amides : Ground-state destabilization in amide electrophilicity. / Pace, Vittorio; Holzer, Wolfgang; Ielo, Laura; Shi, Shicheng; Meng, Guangrong; Hanna, Mina; Szostak, Roman; Szostak, Michal.

In: Chemical Communications, Vol. 55, No. 30, 01.01.2019, p. 4423-4426.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 17 O NMR and 15 N NMR chemical shifts of sterically-hindered amides

T2 - Ground-state destabilization in amide electrophilicity

AU - Pace, Vittorio

AU - Holzer, Wolfgang

AU - Ielo, Laura

AU - Shi, Shicheng

AU - Meng, Guangrong

AU - Hanna, Mina

AU - Szostak, Roman

AU - Szostak, Michal

PY - 2019/1/1

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AB - The structure and spectroscopic properties of the amide bond are a topic of fundamental interest in chemistry and biology. Herein, we report 17 O NMR and 15 N NMR spectroscopic data for four series of sterically-hindered acyclic amides. Despite the utility of 17 O NMR and 15 N 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 17 O NMR and 15 N 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.

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