Transannular Interaction: Molecular Structure and Conformational Properties of N-Aryl-1-Azacyclooctan-5-Ones

Abstract

Conformational properties of N-aryl-1-azacyclooctan-5- ones with a p-methyl, m-methyl, and p-methoxy group as a substituent have been studied by 1H-NMR, 13C-NMR and IR spectroscopies. Transannular interaction of the two functional groups have been examined from the ring inversion barriers and the carbonyl vibrational frequencies with reference to the corresponding data of the respective monofunctional and difunctional compounds.

Keywords

• transannular interaction
• ring inversion
• pseudorotation
• conformational analysis
• eight-membered rings