87413-05-6Relevant articles and documents
Thermodynamics and kinetics of the hydride-transfer cycles for 1-aryl-1,4-dihydronicotinamide and its 1,2-dihydroisomer
Zhu, Xiao-Qing,Cao, Lei,Liu, Yang,Yang, Yuan,Lu, Jin-Yong,Wang, Jian-Shuang,Cheng, Jin-Pei
, p. 3937 - 3945 (2007/10/03)
Five 1-(p-substituted phenyl)-1,4-dihydronicotinamides (GPNAH-1,4-H 2) and five 1-(p-substituted phenyl)-1,2-dihydronicotinamides (GPNAH-1,2-H2) were synthesized, which were used to mimic NAD(P)H coenzyme and its 1,2-dihydroisomer re
An old but simple and efficient method to elucidate the oxidation mechanism of NAD(P)H model 1-aryl-1,4-dihydronicotinamides by cations 2-methyl-5-nitroisoquinolium, tropylium, and xanthylium in aqueous solution
Zhu,Liu,Zhao,Cheng
, p. 370 - 375 (2007/10/03)
Cations 2-methyl-5-mitroisoquinplinium (IQ+), tropylium (T+), and xanthylium (Xn+) were treated by an NAD(P)H model 1-(p-substituted phenyl)-1.4-dihydronicotinamide series (1) in buffered aqueous solution to give the corresponding reduced products by accepting hydride. Effects of the 4-substituents of 1 on the reaction rates were investigated. Hammett's linear free energy relationship analysis on the three reactions of 1 provides the reaction constants of -0.48, -2.2, and -1.4 with IQ+, T+, and Xn+ as the hydride acceptors, respectively. Comparison of the present reactions with the reaction examples whose mechanisms are well-known, such as the reaction of 1 with a one-electron oxidant Fe(CN)6-3, shows that the active site of 1 in the oxidation with IQ+ is at the 4-position on the dihydropyridine ring but that the active site of 1 in the oxidations with T+ and Xn+ is at the 1-position, which is in agreement with the results from the Bronsted-type linear analysis and the relation studies of the logarithm of the second-order rate constants with the oxidation potentials of the hydride donors. According to the dependence of the reaction mechanism on the active site of 1, a conclusion can be made that the reaction of 1 with IQ+ proceeds by direct one-step hydride transfer mechanism, but the reactions of 1 with T+ and Xn+ would take place via multistep hydride transfer mechanism initiated by one-electron transfer.
Reactivity of biologically important reduced pyridines. 4. Effect of substitution on ferricyanide-mediated oxidation rates of various 1,4-dihydropyridines
Brewster,Simay,Czako,Winwood,Farag,Bodor
, p. 3721 - 3726 (2007/10/02)
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