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Keto-enol tautomerism in new silatranes Schiff bases tailed with different substituted salicylic aldehyde
Arabian Journal of Chemistry ( IF 5.3 ) Pub Date : 2020-01-01 , DOI: 10.1016/j.arabjc.2018.09.001
Alexandra Bargan , Mirela Fernanda Zaltariov , Angelica Vlad , Ana-Maria-Corina Dumitriu , Alina Soroceanu , Ana-Maria Macsim , Mihaela Dascalu , Cristian Dragos Varganici , Maria Cazacu , Sergiu Shova

Abstract New Schiff base-type products starting from 1-(3-aminopropyl)silatrane and three derivatives of salicylaldehyde having as substituents 3,5-dichloro- (1), 3-methoxy- (2) and 3,5-di-tert-butyl- (3), respectively were obtained and isolated with high yields (78–87%) in pure, crystalline forms and their structures were established by different methods. The molecular electronic transitions of the compounds in solvents with various polarities were investigated by UV–Vis spectral analysis. Their thermal behavior was studied by thermogravimetric analysis and differential scanning calorimetry, results of the latter highlighting thermocromism of the compounds, proved by the appearance of IR absorption bands specific for enolic form at the temperature corresponding to each sample. The moisture sorption capacity and stability of the compounds in wet environment were investigated by vapor sorption analysis in dynamic regime and IR spectroscopy. The biological activity was assessed by specific tests. All results were discussed in correlation with the nature of substituents and structures formed. The chemical handling of the silatrane tail, by using different substituents on the silicon atom would allow fine tuning of the compounds properties.

中文翻译:

以不同取代水杨醛为尾的新型硅丙烷席夫碱中的酮-烯醇互变异构现象

摘要 以 1-(3-氨基丙基) 硅酮和具有取代基 3,5-二氯-(1)、3-甲氧基-(2) 和 3,5-二叔基的水杨醛的三种衍生物为​​原料的新型席夫碱型产品分别以高产率 (78–87%) 获得和分离出纯晶体形式的 -丁基 - (3) 并通过不同方法建立了它们的结构。通过紫外-可见光谱分析研究了化合物在各种极性溶剂中的分子电子跃迁。通过热重分析和差示扫描量热法研究了它们的热行为,后者的结果突出了化合物的热致变色现象,通过在对应于每个样品的温度下对烯醇形式特异的 IR 吸收带的出现来证明。通过动态状态下的蒸汽吸附分析和红外光谱研究了化合物在潮湿环境中的吸湿能力和稳定性。通过特定测试评估生物活性。所有结果都与取代基的性质和形成的结构相关地进行了讨论。通过在硅原子上使用不同的取代基对硅酮尾进行化学处理,可以对化合物的性质进行微调。
更新日期:2020-01-01
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