Work

Synthesis and Conformational Analysis of N-Azulenyl-N-methyl Amides: Influence of Coplanarity on Amide Conformational Preference

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide We synthesized a series of N -azulenyl- N -methylamides and investigated their conformational preferences in solution and in the solid state. N -(1-Azulenyl)- N -methyl amides 12 and N -(6-azulenyl)- N -methyl amides 14 adopt the cis form almost exclusively in solution and in the crystal state, like general N -methyl aromatic amides such as N -methylbenzanilide and N -methylacetanilide. However, N -(2-azulenyl)- N -methyl amides 13 exhibit high ratios of the trans form in solution and adopt the trans form in the solid state due to the high degree of coplanarity of the 2-azulenyl moiety and the amide plane.

Source: ACS Omega

DOI: 10.1021/acsomega.5c00334