新型联苯胺替代偶氮化合物的合成及互变异构性质研究

Synthesis and Tautomerism of a Novel Benzidine Replacementable Azo Compound

以4,4’-二氨基苯甲酰替苯胺为重氮组分,以N-乙酰-L-酪氨酸为偶合组分,发生重氮化偶合反应,合成了一个新型的偶氮化合物,结构通过UV、1H NMR进行了表征。探讨了所合成化合物的偶氮式-醌腙式互变异构和顺反互变异构性质。结果表明,酸碱效应对偶氮-醌腙互变异构有着显著的影响。化合物在弱酸性条件下主要为醌腙体,中性条件下主要为偶氮体。在甲醇-水体系中,存在着一个pH依赖性的偶氮体-醌腙体分子离子平衡。偶氮化合物365 nm紫外光照射发生了反式-顺式光异构化过程,化合物可由稳定的反式结构变为顺式结构。

A new benzidine replacementable azo compounds were synthesized by diazo-coupling reaction with N-acetyl-L-tyrosine as the coupling component and 4,4'-diaminobenzanilide as the diazo component.The structure of the new azo compound was confirmed by UV and 1H NMR.The azo-hydrazone tautomerizm and trans-cis tautomerizm properties of the compound were discussed.The results showed that the acid-base effect had a significant effect on the tautomerism of azo-hydrazone.The compounds are mainly hydrazone in weak acid condition,and azo form in neutral condition.In methanol-water system,there exists a pH-dependent azo-hydrazone molecular ion equilibrium.The trans-cis isomerization of the azo compound was induced by UV irradiation at 365 nm,and the compound could be converted from trans-structure to cis-structure.