Dielectric properties of cyclic nitramines and related compounds. Part I. Dipole moments and conformations of nitramines, nitrosamines, and 1,3,5-trinitrocyclohexane
Abstract
Dipole moments of 1,3,5-trinitrocyclohexane and various nitramines and nitrosamines have been determined in benzene and dioxan, and the resulting values are compared with values calculated from group moments and corresponding to possible conformations of the molecules. The experimental dipole moments (µ/D) are: 1,3-dinitro-imidazolidine (I), 3·4 ± 0·2; 1,3-dinitroperhydropyrimidine (II), 5·6–5·75; 1,3-dinitroperhydro-1,3-diazepine (III), 5·15–5·25; 1,3,5,7-tetranitroperhydro-1,3,5,7-tetra-azocine (IV), 4·65 ± 0·05; bis-(3,5-dinitroperhydro-1,3,5-triazin-1-yl)methane (V), 7·15 ± 0·05; 1,3,5-tritrosoperhydro-1,3,5-triazine (VI), ca. 3·8–4·5; 1,3-dinitro-5-nitrosoperhydro-1,3,5-triazine (VII), 5·5 ± 0·05; 3,7-dinitroso-1,3,5,7-tetra-azabicyclo[3.3.1]nonane (VIII), 6·8 ± 0·4; 3,7-dinitro-1,3,5,7-tetra-azabicyclo[3.3.1]nonane (IX), 6·9 ± 0·3; 1,7-diacetoxy-2,4,6-trinitro-2,4,6-trizaheptane (X), 2·20–2·25; 1,3,5-trinitrocyclohexane (XI), 3·0 ± 0·2; and N-nitrosopiperidine (XII), 4·4 ± 0·05.