Synthesis with a twist

Article Abstract:

Amide is one of the most fundamental functional groups in chemistry, a link between amino acids in peptides and proteins, and thus a key to the structure of many biological systems. Amides are surprisingly robust compared with structurally related derivatives, and it is believed that this linkage gains stability from electron delocalization and the amide group can be thought of in terms of two structures, one of which is apolar, and the other dipolar.

Connecticut, Protein research, Amides, Isomerism, Isomers (Chemistry)

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Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate

Article Abstract:

Typical acyclic amides are planar, but the amide groups of bicyclic bridgehead lactams are highly twisted, and this distortion from planarity can dramatically affect the stability and reactivity of these amides, increasing the basicity of the nitrogen so that it often behaves more like an amine than a typical planar amide. As a result, the structures and reactivity profiles of these anti-Bredt amides differ significantly from those of planar amides.

California, Ring formation (Chemistry), Cyclization (Chemistry), Borates

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