Novel bridgehead bicyclic lactams: (a) Molecules predicted to have O-protonated and N-protonated tautomers of comparable stability; (b) hyperstable lactams and their O-protonated tautomers

作者：Morgan Jessica^*; Greenberg Arthur

来源：Journal of Chemical Thermodynamics, 2014, 73: 206-212.

DOI：10.1016/j.jct.2013.12.034

• 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.

• 出版日期2014-6