TY - JOUR
T1 - Relayed Proton Brake in N-Pyridyl-2-iso-propylaniline Derivative
T2 - Two Brakes with One Proton
AU - Furukawa, Gaku
AU - Shirai, Takeshi
AU - Homma, Yuki
AU - Caytan, Elsa
AU - Vanthuyne, Nicolas
AU - Farran, Daniel
AU - Roussel, Christian
AU - Kitagawa, Osamu
N1 - Funding Information:
This work was partly supported by JSPS KAKENNHI (Grant C 17K08220).
Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/4/3
Y1 - 2020/4/3
N2 - The addition of methanesulfonic acid to N-(2,6-dimethylpyridin-4-yl)-N-methyl-2-iso-propylaniline led to the selective protonation of the pyridine nitrogen atom, resulting in a significant deceleration of the rotation rates around both N-pyridyl and N-(i-Pr)phenyl bonds through a relayed brake mechanism.
AB - The addition of methanesulfonic acid to N-(2,6-dimethylpyridin-4-yl)-N-methyl-2-iso-propylaniline led to the selective protonation of the pyridine nitrogen atom, resulting in a significant deceleration of the rotation rates around both N-pyridyl and N-(i-Pr)phenyl bonds through a relayed brake mechanism.
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U2 - 10.1021/acs.joc.0c00284
DO - 10.1021/acs.joc.0c00284
M3 - Article
C2 - 32138515
AN - SCOPUS:85083882426
SN - 0022-3263
VL - 85
SP - 5109
EP - 5113
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 7
ER -