Dipole moments of nitro derivatives of indazole

The dipole moments of indazole and a number of its nitro derivatives in dioxane solution were measured. The directions of the vectors of the dipole moments of indazole in the tautomeric 1-H and 2-H forms were determined to solve the problems associated with the tautomerism and the position of the substituents in the molecules. The experimental values of the dipole moments, of the investigated compounds were compared with the values calculated via a vector additive scheme. As a result it was shown that the mononitro and dinitro derivatives of indazole exist primarily in the 1-H tautomeric form, whereas the trinitro and tetranitroindazoles exist in the 2-H tautomeric form. The ratios of the isomers were calculated for compounds that have dipole moments intermediate between the 1-H and 2-H forms. A deviation between the experimental and calculated dipole moments of compounds containing two nitro groups in the ortho position was established; this may be explained by disruption of the coplanarity of the molecules or by deviation from additivity because of the introduction of strong electron-acceptor substituents.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1669–1671, December, 1977.