The Stabilizing Role of the Intramolecular C-H center dot center dot center dot O Hydrogen Bond in Cyclic Amides Derived From alpha-Methylbenzylamine

摘要

A series of five, six-, seven-, and eight-membered lactams containing the chiral auxiliary alpha-methylbenzylamine were structurally analyzed and further studied by DFT calculations with the purpose to examine with detail the previously detected intromolecular C-H center dot center dot center dot O hydrogen-bonding interaction formed between the hydrogen atom of the alpha-methylbenzylamine and the carbonyl group of the cyclic amide. The main objective was to establish whether its presence does have a tangible relevance in their spatial arrangement in solution and in the solid state or is a simple and not stabilizing interaction.