68370-50-3Relevant academic research and scientific papers
N?C Axially Chiral Anilines: Electronic Effect on Barrier to Rotation and A Remote Proton Brake
Iwasaki, Yumiko,Morisawa, Ryuichi,Yokojima, Satoshi,Hasegawa, Hiroshi,Roussel, Christian,Vanthuyne, Nicolas,Caytan, Elsa,Kitagawa, Osamu
, p. 4453 - 4458 (2018)
N-Aryl-N-methyl-2-tert-butyl-6-methylaniline derivatives exhibit a rotationally stable N?C axially chiral structure and the rotational barriers around an N?C chiral axis increased with the increase in electron-withdrawing character of para-substituent on the aryl group. X-ray crystal structural analysis and the DFT calculation suggested that the considerable change of the rotational barriers by the electron effect of para-substituents is due to the disappearance of resonance stabilization energy caused by the twisting of para-substituted phenyl group in the transition state. This structural property of the N?C axially chiral anilines was employed to reveal a new acid-decelerated molecular rotor caused by the protonation at the remote position (remote proton brake).
