NOVEL PROTON SPONGE COMPOUNDS .10. 1,4,5,8-TETRAKIS(DIMETHYLAMINO)NAPHTHALENE - SYNTHESIS, STRUCTURE, PROTON SPONGE AND ELECTRON-DONOR PROPERTIES

被引：47

作者：

BARTH, T ^{[1
]}

KRIEGER, C ^{[1
]}

NEUGEBAUER, FA ^{[1
]}

STAAB, HA ^{[1
]}

机构：

[1] MAX PLANCK INST MED RES,ORGAN CHEM ABT,JAHNSTR 29,W-6900 HEIDELBERG 1,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 08期

关键词：

D O I：

10.1002/anie.199110281

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ''double proton sponge'' 1 undergoes diprotonation by strong acids (pK(a)(1) = 9.8, pK(a)(2) = 4.9; dimethyl sulfoxide scale) and is a strong electron donor (E(ox) = -0.501 V; Fc/Fe+ = 0.0 V). X-ray structure analyses show that the pronounced twisting of 1 around the central C(4a)-C(8a) bond (18.8-degrees) is suppressed by the diprotonation and the accompanying formation of two strong N ... H ... N hydrogen bonds.

引用

页码：1028 / 1030

页数：3

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