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

Daiki Homma (1) , Shuhei Taketani (1) , Takeshi Shirai (1) , Elsa Caytan (2) , Christian Roussel (3) , José Elguero (4) , Ibon Alkorta (5) , Osamu Kitagawa (1)

1 Shibaura Institute of Technology
2 ISCR - Institut des Sciences Chimiques de Rennes
3 ISM2 - Institut des Sciences Moléculaires de Marseille
4 CSIC - Instituto de Quimica Médica
5 CSIC - Spanish National Research Council

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 5-position.

Keywords: Column chromatography; Hydrogen; Mixtures; Purification; Substituents

Domains: Chemical Sciences

Daiki Homma, Shuhei Taketani, Takeshi Shirai, Elsa Caytan, Christian Roussel, et al.. Rotational Behavior of N -(5-Substituted-pyrimidin-2-yl)anilines: Relayed Electronic Effect in Two N–Ar Bond Rotations. Journal of Organic Chemistry, 2022, 87 (12), pp.8118-8125. ⟨10.1021/acs.joc.2c00845⟩. ⟨hal-03706002⟩