ДОСЛІДЖЕННЯ РЕАКЦІЙНОЇ ЗДАТНОСТІ НОВОЇ ТРИЦИКЛІЧНОЇ СИСТЕМИ [1,3]ТІАЗОЛО[2′,3′:3,4][1,2,4]ТРИАЗОЛО[1,5‐a]ПІРИМІДИНУ

Abstract

The theoretical DFT investigation of the reactive ability of [1,3]thiazolo[2′,3′:3,4][1,2,4]triazolo[1,5-a]pyrimidinium bromide 1 through the analysis of molecular orbitals, Fukui function and electrostatic potential has shown the higher activity of bromomethyl group in thiazole ring in reactions with hard nucleophiles. Whereas the reactions with soft nucleophiles can be proceeded upon both reactive centers, with a slight predominance of the same bromomethyl group. Furthermore, the structure of cation in substance 1 indicates the delocalization of positive charges over the all guanidinium fragment. The elimination of one molecule of hydrogen bromide will lead to the uncharged system with clear formation of a double bond in pyrimidinium cycle with simultaneous vanishing of delocalization. This study was partly supported by the International Visegrad Fund (ID 51700627).