17O NMR and 15N 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 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.

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
Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

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

Cite this

Pace, Vittorio ; Holzer, Wolfgang ; Ielo, Laura ; Shi, Shicheng ; Meng, Guangrong ; Hanna, Mina ; Szostak, Roman ; Szostak, Michal. / 17O NMR and 15N 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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17O NMR and 15N 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 - 17O NMR and 15N 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 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.

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