CONFORMATIONAL-ANALYSIS OF CALIX[N]ARENES WITH CHIRAL SUBSTITUENTS BY USING CIRCULAR-DICHROISM

被引：38

作者：

IKEDA, A ^{[1
]}

NAGASAKI, T ^{[1
]}

SHINKAI, S ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC ENGN,DEPT ORGAN SYNTH,FUKUOKA 812,JAPAN

来源：

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY | 1992年 / 5卷 / 10期

关键词：

D O I：

10.1002/poc.610051012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Calix [n] arenes (n = 4 and 6) bearing chiral substituents (R*) on the lower rim (1n) or on the upper rim (4n) were synthesized. The isomers derived from 1(4) were conformationally immobile and showed different circular dichroism (CD) spectra. In the H-1 NMR spectra the proton signals in R* shifted to higher magnetic field when the lower rim is sterically crowded and in the CD spectra a strong CD band appeared. Therefore, the change in the CD spectra is rationalized in terms of R* ... pi interactions. In contrast, compound 4(4) was not conformationally immobilized and the CD spectra changed in response to the metal binding to the methoxy oxygens arranged on the lower rim. The specific metal interaction enabled the metal binding event to be detected by the CD technique.

引用

页码：699 / 710

页数：12