1-Azabicyclo [3.3. 1] nonan-2-one: Nitrogen Versus Oxygen Protonation

B Sliter, J Morgan, A Greenberg

文献索引：Sliter, Brian; Morgan, Jessica; Greenberg, Arthur Journal of Organic Chemistry, 2011 , vol. 76, # 8 p. 2770 - 2781

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被引用次数: 22

摘要

Protonation of typical unstrained amides and lactams is heavily favored at oxygen. In contrast, protonation of the highly distorted lactam 1-azabicyclo [2.2. 2] octan-2-one is heavily favored at nitrogen. What structures occupy “crossover boundaries” where N-and O- protonation are nearly equienergetic? Density function theory calculations at the B3LYP/6- 31G* level, as well as QCISD (T)/6-31G* calculations, predict that 1-azabicyclo [3.3. 1] ...