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Journal articles
N-C Axially Chiral Anilines Electronic Effect on Barrier to Rotation and A Remote Proton Brake
Abstract : 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).
Cited literature [19 references]
https://hal-univ-rennes1.archives-ouvertes.fr/hal-01771098
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Sunday, April 7, 2019 - 6:40:05 AM
Last modification on : Wednesday, November 3, 2021 - 4:41:13 AM
Contributor : Laurent Jonchère Connect in order to contact the contributor
Submitted on : Sunday, April 7, 2019 - 6:40:05 AM
Last modification on : Wednesday, November 3, 2021 - 4:41:13 AM
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