TY - JOUR
T1 - Rotational Behavior of N-(5-Substituted-pyrimidin-2-yl)anilines
T2 - Relayed Electronic Effect in Two N-Ar Bond Rotations
AU - Homma, Daiki
AU - Taketani, Shuhei
AU - Shirai, Takeshi
AU - Caytan, Elsa
AU - Roussel, Christian
AU - Elguero, José
AU - Alkorta, Ibon
AU - Kitagawa, Osamu
N1 - Funding Information:
This work was partly supported by JSPS KAKENHI Grant Number C 20K06945. VT-NMR experiments have been performed using the PRISM core facility (Biogenouest, UMS Biosit, Université de Rennes 1- Campus de Villejean- 35043 RENNES Cedex, FRANCE).
Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/6/17
Y1 - 2022/6/17
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.2c00845
DO - 10.1021/acs.joc.2c00845
M3 - Article
AN - SCOPUS:85132026992
SN - 0022-3263
VL - 87
SP - 8118
EP - 8125
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 12
ER -