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.
| Original language | English |
|---|---|
| Pages (from-to) | 775-781 |
| Number of pages | 7 |
| Journal | Journal of Physical Organic Chemistry |
| Volume | 15 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 2002 Nov 1 |
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All Science Journal Classification (ASJC) codes
- Physical and Theoretical Chemistry
- Organic Chemistry
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Keto-enol tautomerism of β-ketoamides and characterization of a sterically crowded α-amido-β-ketoamide. / Sung, Kuang-Sen; Wu, Ru Rong; Sun, Shu Yi.
In: Journal of Physical Organic Chemistry, Vol. 15, No. 11, 01.11.2002, p. 775-781.Research output: Contribution to journal › Article
TY - JOUR
T1 - Keto-enol tautomerism of β-ketoamides and characterization of a sterically crowded α-amido-β-ketoamide
AU - Sung, Kuang-Sen
AU - Wu, Ru Rong
AU - Sun, Shu Yi
PY - 2002/11/1
Y1 - 2002/11/1
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.
UR - http://www.scopus.com/inward/record.url?scp=0036851425&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036851425&partnerID=8YFLogxK
U2 - 10.1002/poc.554
DO - 10.1002/poc.554
M3 - Article
VL - 15
SP - 775
EP - 781
JO - Journal of Physical Organic Chemistry
JF - Journal of Physical Organic Chemistry
SN - 0894-3230
IS - 11
ER -