Control of the rotational barrier and spatial disposition of the N-(2'-methylphenyl) group in succinimides by substituent and solvent effects

被引：61

作者：

Kishikawa, K ^{[1
]}

Yoshizaki, K ^{[1
]}

Kohmoto, S ^{[1
]}

Yamamoto, M ^{[1
]}

Yamaguchi, K ^{[1
]}

Yamada, K ^{[1
]}

机构：

[1] CHIBA UNIV, CTR CHEM ANAL, INAGE KU, CHIBA 263, JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 08期

关键词：

D O I：

10.1039/a605896e

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Both the rotational barrier for the N-(2'-methylphenyl) group in benzylamino-N-(2'- methylphenyl)succinimides 1a-h (X = NEt2 OMe, Me, H, F, Cl, CO2Me and NO2) and the spatial disposition of the N-(2'-methylphenyl) group in N-(4'-substituted 2'-methylphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximides 2a-h (X = NEt2, OMe, Me, H, F, Cl, CO2Me and NO2) are controlled by the substituents present mid the solvents used. The rotational barrier of 1 decreases with an increase in sigma(p) (Hammett's para substituent constant of X) and increases in proportion to an increase of the solvent parameter [E-T(30)]. Clear correlation was observed in the plots of the synlanti ratio of 2 against sigma(m) (Hammett's meta-substituent constant of X) and the ratios are also controllable by the solvent polarity (mu).

引用

页码：1233 / 1239

页数：7

共 38 条

[1]

VAN DER WAALS VOLUMES + RADII [J].