期刊
JOURNAL OF CHEMICAL THERMODYNAMICS
卷 73, 期 -, 页码 206-212出版社
ACADEMIC PRESS LTD- ELSEVIER SCIENCE LTD
DOI: 10.1016/j.jct.2013.12.034
关键词
Bicyclic lactams; Hyperstability; Nitrogen vs. oxygen protonation
The N- and O-protonated tautomers of 1-azabicyclo[3.3.1] nonan-2-one are predicted computationally to be comparable in stability. This was experimentally verified. The same theoretical models are employed to explore a wider range of bridgehead bicyclic lactams. Some additional examples are identified: some slightly preferring N-protonation and some O-protonation. Winkler-Dunitz parameters are employed to see if a pattern in geometry would emerge to help in the prediction of protonation preference. A number of larger bicyclic lactams are identified as possibly being hyperstable in O-protonation. (C) 2014 Elsevier Ltd. All rights reserved.
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