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

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...

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Published inJournal of organic chemistry Vol. 87; no. 12; pp. 8118 - 8125
Main Authors Homma, Daiki, Taketani, Shuhei, Shirai, Takeshi, Caytan, Elsa, Roussel, Christian, Elguero, José, Alkorta, Ibon, Kitagawa, Osamu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.06.2022
Amer Chemical Soc
Subjects
Chemical Sciences
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RATES
NMR
ATROPISOMERISM
MOLECULAR BRAKE
PROTONATION
Purification
Substituents
Mixtures
Hydrogen
Column chromatography
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00845