Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 26, Pages 8836-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja101690u
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Funding
- National Institute of General Medical Sciences [GM-49093]
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The straightforward protonation of lactams by treatment with acid and the full structural characterization of three resulting N-protonated lactams are disclosed. This work provides experimental evidence that N-protonation of amide bonds results in a dramatic increase in nonplanarity about the C-N amide bond. The resulting compounds are discussed in structural, spectroscopic, and reactivity terms. The data suggest that distortion of these amide bonds by similar to 50 degrees is sufficient for their effective N-activation.
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