Rotational Behavior of N-(5-Substituted-pyrimidin-2-yl)anilines: Relayed Electronic Effect in Two N-Ar Bond Rotations

N-Methyl-2-methoxymethylanilines 1 bearing various 5-substituted-pyrimidin-2-yl groups were prepared, and their rotational behaviors were explored in detail. It was revealed that the rotational barriers around two N-Ar bonds increase in proportion to the electron-withdrawing ability of substituents X at the S-position.

Automated summary

In this study, N-methyl-2-methoxymethylanilines bearing various 5-substituted-pyrimidin-2-yl groups were synthesized and their rotational behaviors were investigated. The results revealed that the rotational barriers around the N-Ar bonds increase proportionally to the electron-withdrawing ability of the substituent X at the S position.