N-乙酰-L-酪氨酸甲酯偶氮衍生物的合成及紫外可见光谱学性质

Synthesis and UV-Vis Spectrum of N-Acetyl-L-tyrosine Methyl Ester Azo Derivatives

以N-乙酰-L-酪氨酸甲酯为原料,合成了6个新型的偶氮衍生物,通过IR、~1HNMR、^(13)CNMR、EI-MS和元素分析进行了表征。考察了所合成化合物的偶氮式-腙式互变异构以及溶剂和pH对紫外可见光谱的影响。结果表明,溶质-溶剂相互作用会影响化合物在不同溶剂中的λ_(max)发生微小的变化,分子内和分子间氢键的作用影响较大。溶液pH会直接影响偶氮式和腙式的平衡构成,随着pH的增加,偶氮式在偶氮式-腙式互变异构平衡中的比例逐渐降低。这些偶氮化合物有望成为一类潜在的pH指示剂。

Six new azo compounds were synthesized,N-acetyl-L-tyrosine methyl ester as raw material. The structures of the new azo compounds were confirmed by IR,1HNMR,13CNMR,EI-MS and elemental analysis. The effects of various solvent and pH values upon the absorption spectra of the azo compounds were tested to investigate the azo-hydrazonetautomerizm phenomena. The results showed that the solute-solvent interactions in different solvents can affect minor changes of λmax in the compounds,the role of in- tramolecular and intermolecular hydrogen bonds plays an important role. The proportion of azo tautomer in azo-hydrazonetaotomer- izm equilibrium is decreased with the increasing of pH. These new azo compounds could potentially be used as pH indicators.