STUDY OF THE NITRATION REACTION OF 1-OCTENE AND DFT CALCULATIONS

In the presented study, a simple method for the nitration of 1-octene was proposed. The reaction was carried out in the presence of NaNO2 using HNO3. The composition and structure of the obtained reaction product were studied by 1 H and 13 C NMR spectroscopy methods. It was determined that three products were obtained from the reaction (1a, 1b and 1c). The total yield of products was 73%. It was determined by NMR method that compound 1a is 38%, compound 1b is 17%, and compound 1c is 45%. Theoretical calculations of the three substances (1a, 1b, 1c) assumed as reaction products were carried out by DFT method using ORCA-4.2.1 computational package. 6-31G(d,p) basis sets and the B3LYP level of theory were used in the geometric optimization. Bond lengths and angle degrees were calculated in the optimized structures, important quantum-chemical parameters such as E HOMO , ELUMO, chemical hardness, chemical softness, electronegativity, chemical potential, electrophilicity index, ionization potential and electron affinity were studied. It was found that HOMO and LUMO orbitals in all three compounds are mainly delocalized on ONO, OH and NO2 fragments. Among the studied substances, compound 1c was more stable (triangle E=6.141 eV), and compound 1a showed more reactive ((triangle E=5.299 eV) property. According to theoretical calculations, all three compounds have high biological activity (electrophilicity index-1a-4.610 eV,-1b-3.560 eV,-1c-4.930 eV). In the article, compound 1c is taken as the main product due to the yield and stability of the reaction products.