Abstract: Heterocyclic compounds are of great interest to researchers as potential compounds in the creation of biologically active substances or substances with high energy. 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane (THAP) consists of three condensed rings connected by a single C1-C5 bond, is a new, poorly studied substance synthesized in the second decade of the 21st century. Theoretical calculations of the energies of nitro-derivatives of propellanes with five or six nitrogen atoms have shown that they are promising for use as high-energy substances. The aim of the work was to carry out quantum-chemical calculations of the heats of formation and combustion, as well as the length of the propellane bond of nitro- and acetyl derivatives of 3,7,10-trioxo-2,4,6,8,9,11- hexaaza[3.3.3]propellane, as well as its reduced analogue 2,4,6,8,9,11-hexaaza[3.3.3]propellane (HAP) with a different number of substitutes. As a result of the research work, the following regularity was revealed: the successive introduction of nitro groups into the structure under study increases the heats of formation of the resulting derivatives, while the trend is opposite for acetyl groups. It turned out that the hexanitro derivative of THAP is comparable in thermodynamic stability to hexanitrobenzene, and the reduced propellane (HAP) with six nitro groups is comparable to CL-20. Behavior of the C1-C5 propellane bond length upon successive substitution of THAP compound with nitro- and acetyl groups. The accumulation of acetyl groups causes a monotonic shortening of this bond, up to the usual length of C(sp3)-C(sp3). In the case of nitro groups, the trend is more complex: first, shortening and then significant lengthening, up to 1.67 Å for six nitro groups in 3,7,10-trioxo-2,4,6,8,9,11-hexanitro-2,4,6, 8,9,11- hexaaza[3.3.3]propellane. Hexaazapropellane (HAP), despite its non-rigid structure, has 22 stable conformers, whereas THAP has two, and shorter bonds, which is likely to make it possible to synthesize its hexanitro derivative in the future.
Index terms: propellane, azapropellane, quantum chemical calculations.


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