Abstract: It has previously been reported that during the transimination reaction between N,N’-di-tert-butyl-1,2-ethanediimine and hydroxylamine, the tert-butyl group can be substituted in a stepwise manner to furnish intermediate N-hydroxy-N’-tert-butyl-1,2- ethanediimine. Therefore, this study aimed at investigating the reaction of hydroxylamine with other alkyldiimines, particularly with N,N’diethyl-1,2-ethanediimine, N,N’-dipropyl-1,2-ethanediimine, N,N’-dibutyl-1,2-ethanediimine, N,N’-dihexadecyl-1,2- ethanediimine. Hydroxylamine was consequently been found to react with the ethylamine- and propylamine-based diimines to yield N-hydroxy-N’propyl-1,2-ethanediimine and N-hydroxy-N’-ethyl-1,2-ethanediimine, and with the butylamine- and hexadecylamine-based diimines to deliver the glyoxime. Because hydroxyleamine was utilized in this study, the reaction was carried out in an aqueous medium with added sodium alkali, followed by the isolation of the target product and the formed salt (sodium chloride). The reaction time was 3 h. The reaction of substitution of hydroxylamine for the amine group under the said conditions did not take place with N,N’-diisobutyl1,2-ethanediimine and N,N’-diisopropyl-1,2- ethanediimine. The structures of the resultant glyoxime derivatives were proved by NMR and IR spectroscopies. The wavelengths at 1570 сm-1 and 1598 сm-1 are typical of the C=N double bond. NMR spectroscopy showed a signal at 11.6-11.8 ppm representative of the OH group proton shift. Also, the diimines had two signals at 7.7-8.0 ppm inherent in the CH= protons that are present on the N atoms with different surroundings. The PASS software for biological activity prediction demonstrated that the synthesized diimines could be used to treat phobic disorders, and as an antiseborrheic agent.
Index terms: glyoxime, hydroxylamine, diimine, transimination reaction.