Cyclobutene-1,2-diones. A theoretical and spectroscopic study

被引：25

作者：

Cerioni, G

Janoschek, R

Rappoport, Z

Tidwell, TT

机构：

[1] GRAZ UNIV, INST THEORET CHEM, A-8010 GRAZ, AUSTRIA

[2] HEBREW UNIV JERUSALEM, DEPT ORGAN CHEM, IL-91904 JERUSALEM, ISRAEL

[3] UNIV TORONTO, DEPT CHEM, TORONTO, ON M5S 3H6, CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 18期

关键词：

D O I：

10.1021/jo960484a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The properties of substituted cyclobutene-1,2-diones 1 are examined by the use of O-17 NMR spectroscopy and theoretical calculations and compared to those of cyclopropenones 2 and other models. Cyclobutene-1,2-diones have less negative charge per oxygen compared to cyclopropenones, and electron donation by substituents enhances the negative charge on oxygen. Calculated O-17 chemical shifts reproduce the measured trends. The dianions of squaric and deltic acids are highly stabilized by negative charge delocalization to the oxygens.

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页码：6212 / 6217

页数：6

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