Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, Akad. Arbuzov str. 8, 420088 Kazan, Russia.
State Research Institute of Chemical Products Federal State Enterprise, Svetlaya str. 1, 420033 Kazan, Russia.
Int J Mol Sci. 2022 Jan 27;23(3):1471. doi: 10.3390/ijms23031471.
New derivatives of benzofuroxan containing triazidoisobutyl fragments, opening the way for the creation of highly effective compositions with an increased value of energy characteristics, were synthesized for the first time. Such compounds are also an excellent platform for further modification and for the preparation of new biologically-active compounds containing tetrazole and triazole fragments. Calculations of heats of formation performed with the DFT (density functional theory) method showed that the studied compounds are high-energetic density ones, the enthalpies of formation of which are comparable to the enthalpies of formation of similar benzofuroxan derivatives and exceeds experimental enthalpy of formation of CL-14 (5,7-diamino-4,6-dinitrobenzofuroxan). The analysis of DSC indicates a sufficiently high thermal stability of the synthesized azidobenzofuroxans, which are acceptable for their use as components in the creation of highly efficient compositions with an increased value of energy characteristics.
首次合成了含三氮杂异丁基片段的苯并呋咱新衍生物，为开发具有更高能量特性值的高效组合物开辟了道路。这些化合物也是进一步修饰和制备含有四唑和三唑片段的新型生物活性化合物的绝佳平台。使用密度泛函理论 (DFT) 方法进行的生成热计算表明，所研究的化合物是高能密度化合物，其生成焓与类似苯并呋咱衍生物的生成焓相当，并且超过了 CL-14（5,7-二氨基-4,6-二硝基苯并呋咱）的实验生成焓。DSC 分析表明，所合成的叠氮苯并呋咱具有足够高的热稳定性，可接受其作为在具有更高能量特性值的高效组合物的创造中使用的组分。
