Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

被引：26
|
作者：
Edeson, Steven J. [1 ]
Jiang, Julong [1 ]
Swanson, Stephen [2 ]
Procopiou, Panayiotis A. [2 ]
Adams, Harry [1 ]
Meijer, Anthony J. H. M. [1 ]
Harrity, Joseph P. A. [1 ]
机构：
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
[2] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 20期
基金：
英国工程与自然科学研究理事会;
关键词：
ELUCIDATION; COMPLEXES; ACID; DFT;
D O I：
10.1039/c4ob00496e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.
引用
收藏
页码：3201 / 3210
页数：10
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