含氮杂环生物活性化合物的热化学研究
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摘要
含氮杂环化合物不仅在农药而且在医药上都具有广泛的应用,因而是一类非常重要的有机化合物。近几十年来,科学家们不断地探索其新的合成工艺,并对其结构和性能进行了很多研究,然而有关这类化合物的基础热力学以及化合物结构与其热力学性质之间的关系还研究得很少。本论文采用精密绝热量热法、燃烧量热法和近代热分析技术对新合成的嘧啶胺类、三唑类和苯并噻唑类含氮杂环化合物的热容、相变、燃烧热、标准摩尔生成焓和热稳定性等基础热力学性质进行了系统的研究,取得如下结果:
利用含氮有机碱和酸成鎓盐的反应,以嘧霉胺和具有生物活性的酸为原料,合成了9种新型嘧啶胺类化合物,用IR、~1HNMR和元素分析方法确认了其结构,并测试了其生物活性。
利用改进的精密自动绝热量热仪测量了嘧啶胺类、三唑类和苯并噻唑类共11个含氮杂环化合物在80-380K温区的热容。利用熔化温区热容数据,计算出化合物的熔化温度、熔化焓和熔化熵。由非相变温区热容数据建立了热容随温度变化的拟合方程,根据焓、熵与热容的热力学函数关系,求出了每种化合物相对于298.15K的标准热力学函数值,[ H_(T)-H_(298.15K)]和[S_(T)-S_(298.15K)]。
通过燃烧量热法测定了部分嘧啶胺类化合物的燃烧热并计算出其标准摩尔生成焓和嘧霉胺与有机酸成盐反应的反应焓,由此推测了化合物结构的稳定性。
根据量热法和热分析的实验数据,从结构和能量的角度讨论了结构相似化合物热力学性质的变化规律。
Nitrogen-containing heterocyclic compounds are important organic compounds, which has a good activity not only in pesticide but also in medicine. Since several decades of years, great progression has been made for synthesis and characterization of structure and properties about the nitrogen-containing heterocyclic compounds in order to make them more suitable for the industrial production. However, the thermodynamics in the synthesis process and the research on the relationship between the structure and the thermodynamic properties of the compounds are quite few. In the present thesis low-temperature heat capacity, heats of combustion and standard molar enthalpies of formation for pyrimidinamine, triazole and benzothiazole compounds have been investigated by a fully automated precision adiabatic calorimeter, a high precision oxygen bomb calorimeter and TG-DSC, respectively. Major measurements and research results are summarized as follows:
Nine pyrimidinamine compounds were synthesized with pyrimethanil and biological acid as raw materials and their structures have been confirmed through IR, ~1HNMR and elemental analysis. Their preliminary biological activities have been tested by asp-agar-diluted method. The results of tests showed that most of them exhibited excellent fungicidal activities. The relationship between the structures and the biological activities of the pyrimethanil salts was discussed.
Low-temperature heat capacities of the compounds were measured in the temperature range from 80K to 380K by the fully automated adiabatic calorimeter. The thermodynamic data, such as temperatures, enthalpies and entropies of the fusions, have been calculated according to the experimental heat capacities. Valid and virtual section of the heat-capacity curve of the compound was fitted and a
利用含氮有机碱和酸成鎓盐的反应,以嘧霉胺和具有生物活性的酸为原料,合成了9种新型嘧啶胺类化合物,用IR、~1HNMR和元素分析方法确认了其结构,并测试了其生物活性。
利用改进的精密自动绝热量热仪测量了嘧啶胺类、三唑类和苯并噻唑类共11个含氮杂环化合物在80-380K温区的热容。利用熔化温区热容数据,计算出化合物的熔化温度、熔化焓和熔化熵。由非相变温区热容数据建立了热容随温度变化的拟合方程,根据焓、熵与热容的热力学函数关系,求出了每种化合物相对于298.15K的标准热力学函数值,[ H_(T)-H_(298.15K)]和[S_(T)-S_(298.15K)]。
通过燃烧量热法测定了部分嘧啶胺类化合物的燃烧热并计算出其标准摩尔生成焓和嘧霉胺与有机酸成盐反应的反应焓,由此推测了化合物结构的稳定性。
根据量热法和热分析的实验数据,从结构和能量的角度讨论了结构相似化合物热力学性质的变化规律。
Nitrogen-containing heterocyclic compounds are important organic compounds, which has a good activity not only in pesticide but also in medicine. Since several decades of years, great progression has been made for synthesis and characterization of structure and properties about the nitrogen-containing heterocyclic compounds in order to make them more suitable for the industrial production. However, the thermodynamics in the synthesis process and the research on the relationship between the structure and the thermodynamic properties of the compounds are quite few. In the present thesis low-temperature heat capacity, heats of combustion and standard molar enthalpies of formation for pyrimidinamine, triazole and benzothiazole compounds have been investigated by a fully automated precision adiabatic calorimeter, a high precision oxygen bomb calorimeter and TG-DSC, respectively. Major measurements and research results are summarized as follows:
Nine pyrimidinamine compounds were synthesized with pyrimethanil and biological acid as raw materials and their structures have been confirmed through IR, ~1HNMR and elemental analysis. Their preliminary biological activities have been tested by asp-agar-diluted method. The results of tests showed that most of them exhibited excellent fungicidal activities. The relationship between the structures and the biological activities of the pyrimethanil salts was discussed.
Low-temperature heat capacities of the compounds were measured in the temperature range from 80K to 380K by the fully automated adiabatic calorimeter. The thermodynamic data, such as temperatures, enthalpies and entropies of the fusions, have been calculated according to the experimental heat capacities. Valid and virtual section of the heat-capacity curve of the compound was fitted and a
引文
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