1-(NITROSOAMINO)BENZIMIDAZOLES CONTAINING ELECTRON-ACCEPTOR SUBSTITUENTS AT THE AMINE NITROGEN. THEORETICAL AND EXPERIMENTAL INVESTIGATION OF CONFORMATIONAL MOBILITY
Keywords:
1-(nitrosoamino)benzimidazoles, nitrosohydrazines, dynamic 1 H NMR, E-Z isomerization, quantum-chemical calculationsAbstract
The previously unknown 1-(N-nitrosoallylamino)- and 1-(N-nitrosopropargylamino)benzimidazoles have been synthesized and they exist in solution as a mixture of the E- and Z-conformers due to hindered rotation around the N–N(O) bond. The activation energies for the E-Z transition in these compounds and for the model N-benzyl analog have been determined by a dynamic 1H NMR method. With a view to studying the effect of a substituent at the amino nitrogen on the E-Z isomerization we have carried out 3-21G and 6-31G** type ab initio calculations of the stable conformers of a series of N-nitrosohydrazines.
How to Cite
Dyablo, O. V.; Kletskii, M. E.; Pozharskii, A. F. ; Yakovleva, E. V. Chem. Heterocycl. Compd. 2002, 38,954. [Khim. Geterotsikl. Soedin. 2002, 1095.]
For this article in the English edition, see DOI https://doi.org/10.1023/A:1020973514280
