Electronic properties, structure and reactivity of the azine group C=N-N=C and mechanism of biologically important azines degradation.

Abstract:
The project is based on the (sono)electrochemical and spectroscopic research of structure and reactivity of series of cyclic and acyclic azines bearing the >C=N-N=C group in order to interpret the absence of delocalization observed by us recently in this seemingly conjugated system. The redox potentials, NMR-chemical shift, kinetic and spectroscopic data etc. jointly with the identification of intermediates and products make possible to formulate conditions under which the neighbouring groups and the structure of the whole molecule affect the character of the N-N bond. The results will be correlated with x-ray crystallographic data and compared to quantum chemical computation. This grouping of two azomethine bonds occurs also in some pesticides. Sincethese bonds are reducible on the one hand and undergo hydrolysis on the other hand, a detailed investigation of the sequence, course and kinetics of these reactions enables to formulate the detailed degradation mechanism.