%0 Journal Article
%T The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities
%A MARIO ZLATOVIC
%A DUSAN SLADIC
%A MIROSLAV J. GASIC
%J Journal of the Serbian Chemical Society
%D 1999
%I Serbian Chemical Society
%X Several NADH model compounds, N-alkyl-1,4-dihydronicotinamides, some of them possessing amphiphilic properties, have been synthesized, and the kinetics of their reaction with a biologically active liphophilic quinone, avarone, has been studied in a protic solvent both in the presence and absence of cationic, anionic or non-ionic surfactants. In the absence of micellar agents, the medium- and long-chain N-dodecyl (3) and N-heptadecyl (4) derivatives show a significant increase in the reaction rates compared to other model compounds, due to the stabilization of the semiquinone intermediate. Anionic surfactants retard the reaction, non-ionic surfactants slightly accelerate the reaction with the short-chain derivatives, and retard the reaction with the medium- and long-chain derivatives, and the cationic surfactants increase the reaction rate with all derivatives except the long-chain 4. The results support the e-p-e mechanism of the reduction of lipophilic quinones by NADH models in protic medium.
%K avarone
%K quinone
%K NADH models
%K surfactants
%K kinetics
%U http://www.shd.org.yu/HtDocs/SHD/Vol64/No11-Pdf/V64-no11-01.zip