Intramolecular versus intermolecular induction of helical handedness in pyridinedicarboxamide oligomers

被引：65

作者：

Maurizot, V ^{[1
]}

Dolain, C ^{[1
]}

Huc, I ^{[1
]}

机构：

[1] Inst Europeen Chim & Biol, F-33607 Pessac, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 07期

关键词：

chirality; conformation analysis; hydrogen bonds; helical structures; supramolecular chemistry;

D O I：

10.1002/ejoc.200400641

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new convergent synthetic scheme has been developed to prepare oligoamides of 2,6-diaminopyridine and 4-decyloxy2,6-pyridinedicarboxylic, acid. These compounds adopt stable single helical conformations in solution. NMR and circular dichroism studies show that intramolecular and intermolecular chiral induction of handedness in these helices is possible. Intramolecular induction is effected by attaching a single chiral group to the end of an oligomer. Intermolecular induction results from various noncovalent interactions between chiral carboxylic or sulfonic acids and the terminal residues of the oligoamides. Intramolecular induction appears to be more efficient than intermolecular induction. When both effects compete, intramolecular induction prevails. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

引用

页码：1293 / 1301

页数：9

共 42 条

[1] PHOTORESPONSIVE PROPERTIES OF OPTICALLY-ACTIVE (METH)ACRYLIC HOMOPOLYMERS WITH PENDENT L-LACTIC ACID OR L-ALANINE RESIDUES CONNECTED TO 4-AMINOAZOBENZENE [J].