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EN
The HOMA (Harmonic Oscillator Model of Aromaticity) index is one of the most useful and popular calculation methods in the p-electron delocalization studies. Its idea is simple and calculations are very fast. Nevertheless, the HOMA method has not been applied so far to the compounds containing the carbon-selenium bond(s). In this work the HOMA parameters for such compounds are presented and several model selenium compounds are investigated. In order to obtain the deeper insight, calculations have been executed for oxygen and thio analogs of studied selenium compounds. HOMA values have been compared with the data provided by other aromaticity indices like IA, NICS(0) and NICS(1).
EN
Synthesis of bis(2-aminophenyl) diselenide 1 derivatives, having amino acids and dipeptides moieties, has been reported. This process has been realized by acylation of both amine groups in 1 us ing N-Boc blocked amino acids 8 in the presence of DCC and HOBT, followed by deprotection to hydrochlorides 9. The free amines 2 have been obtained by removing the protective groups. In the similar way dipeptides 3, 10 and 11 have been prepared. Selected compounds have been tested as potential antiviral, antibacterial and antifungial agents.
EN
The reactions of cyclic selenenamides: benzisoselenazol-3(2H)-ones and 1,3,2-benzodiselenazoles 3 with living cell nucleophiles such as water and thiols were investigated. Both of them caused Se–N bond cleavage. The thiolysis of 1 led to selenosulphides 6, 9 or to products of their disproportionation the equimolar mixtures of diselenides 7 and disulphides 8. The hydrolysis of 1 and 3 as well as thiolysis of 3 resulted in formation of corresponding diaryl diselenides 7 or 10.
EN
The reactions of two o-substituted bromoselenobenzenes: 2-(bromoseleno)benzene sulfonyl chloride and 1,2-di(bromoseleno)benzene with bisnucleophiles having amino, thiol and active methylene group have been studied. In most cases five membered rings, containing selenium as well as nitrogen and sulfur atoms, such as 1,3,2-benzothiaselenazole, 1,2,3-dithiaselenazole, benzo-1,3(2H)-thiaselenole, 1,3,2-benzodiselenazole and benzo-1,3(2H)-diselenole, were formed. The elaborated procedures have synthetic value.
EN
The reaction of title compound 6 with primary aliphatic or aromatic amines was investigated. The products were 2,2_-diselenobis(benzenesulfonamides) (4) accompanied in some cases by 1,3,2-benzothiaselenazole 1,1-dioxides (3). Exceptionally, when aniline was a reagent, 2-(sulfamoylphenyl)phenylselenenylanilide was produced. These results are interpreted in the light of the proposed mechanisms. The compounds 3 and 4 exhibited catalytic activity in hydroperoxide oxidation of cyclohexanone (12) and 1-naphthaldehyde N,N-dimethylhydrazone (17). Although they were inactive against patogenic bacteria and fungi an appreciable antiviral activity against HSV-1 and EMCV of the compounds 3b, 3c and 4b was observed.
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