Keto-enol tautomerism of β-ketoamides and characterization of a sterically crowded α-amido-β-ketoamide

Kuangsen Sung; Ru Rong Wu; Shu Yi Sun

doi:10.1002/poc.554

Keto-enol tautomerism of β-ketoamides and characterization of a sterically crowded α-amido-β-ketoamide

Kuangsen Sung, Ru Rong Wu, Shu Yi Sun

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

An α-amido-β-ketoamide (1) and two α-alkyl-β-ketoamides (2 and 3) were prepared and characterized, and their keto-enol tautomerism was studied by H/¹³C NMR spectroscopy. Both α-alkyl-β-ketoamides 2 and 3 are in the keto form in CDCl₃, and their enol forms cannot be detected by ¹H/¹³C NMR spectroscopy, whereas the α-amido-β-ketoamide 1 shows both keto and enol forms in CDCl₃ with an experimental K_E of 0,70 at 298 K.

Original language	English
Pages (from-to)	775-781
Number of pages	7
Journal	Journal of Physical Organic Chemistry
Volume	15
Issue number	11
DOIs	https://doi.org/10.1002/poc.554
Publication status	Published - 2002 Nov

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry

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title = "Keto-enol tautomerism of β-ketoamides and characterization of a sterically crowded α-amido-β-ketoamide",

abstract = "An α-amido-β-ketoamide (1) and two α-alkyl-β-ketoamides (2 and 3) were prepared and characterized, and their keto-enol tautomerism was studied by H/13C NMR spectroscopy. Both α-alkyl-β-ketoamides 2 and 3 are in the keto form in CDCl3, and their enol forms cannot be detected by 1H/13C NMR spectroscopy, whereas the α-amido-β-ketoamide 1 shows both keto and enol forms in CDCl3 with an experimental KE of 0,70 at 298 K.",

author = "Kuangsen Sung and Wu, {Ru Rong} and Sun, {Shu Yi}",

year = "2002",

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Y1 - 2002/11

N2 - An α-amido-β-ketoamide (1) and two α-alkyl-β-ketoamides (2 and 3) were prepared and characterized, and their keto-enol tautomerism was studied by H/13C NMR spectroscopy. Both α-alkyl-β-ketoamides 2 and 3 are in the keto form in CDCl3, and their enol forms cannot be detected by 1H/13C NMR spectroscopy, whereas the α-amido-β-ketoamide 1 shows both keto and enol forms in CDCl3 with an experimental KE of 0,70 at 298 K.

AB - An α-amido-β-ketoamide (1) and two α-alkyl-β-ketoamides (2 and 3) were prepared and characterized, and their keto-enol tautomerism was studied by H/13C NMR spectroscopy. Both α-alkyl-β-ketoamides 2 and 3 are in the keto form in CDCl3, and their enol forms cannot be detected by 1H/13C NMR spectroscopy, whereas the α-amido-β-ketoamide 1 shows both keto and enol forms in CDCl3 with an experimental KE of 0,70 at 298 K.

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Keto-enol tautomerism of β-ketoamides and characterization of a sterically crowded α-amido-β-ketoamide

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