GEOMETRY VERSUS BASICITY OF BILATRIENES - STRETCHED AND HELICAL PROTONATED BILIVERDINS

被引：21

作者：

KROIS, D

机构：

[1] Institut für Organische Chemie, Universität Wien, Wien

来源：

MONATSHEFTE FUR CHEMIE | 1991年 / 122卷 / 6-7期

关键词：

PROTONATED BILIVERDINS; CONFORMATION DEPENDENT BASICITY; BRIDGED BILIVERDINS; PKA-VALUES; UV-VIS; NMR;

D O I：

10.1007/BF00809802

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The ease of protonation of bilatrienes at the pyrrolenine nitrogen critically depends on their conformation. The biliverdin 2 being constrained to a helical (Z, Z, Z, syn, syn, syn) geometry by its four link chain is ca. three orders of magnitude less basic than flexible open-chain bilatrienes like biliverdin-IX-alpha dimethyl ester (1), which is shown to adopt a stretched conformation in its monoprotonated form. These results are obtained by a comparative investigation of the titrations of 1 and 2 with sulfuric acid in methanol and methanol-water by means of UV-VIS and NMR spectroscopy.

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页码：495 / 506

页数：12

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