Efficient modulation of hydrogen-bonding interactions by remote substituents

被引：50

作者：

Chang, SY ^{[1
]}

Kim, HS

Chang, KJ

Jeong, KS

机构：

[1] Yonsei Univ, Ctr Bioact Mol Hybrids, Seoul 120749, South Korea

[2] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 02期

关键词：

D O I：

10.1021/ol035954j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A series of tetralactam macrocycles having different substituents were prepared, and their binding affinities for an adipamide guest were investigated in CDCl(3) by (1)H NMR titrations. The association constants strongly depend on the substituents, varying up to DeltaDeltaG = 3.4 kcal/mol; electron-donating substituents (OMe, NMe(2)) decrease the binding affinity, while electron-withdrawing groups (Cl, NO(2)) increase it. These large substituent effects have been rationalized by secondary repulsions and partial perturbations of intramolecular hydrogen bonds.

引用

页码：181 / 184

页数：4

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