13309-33-6Relevant academic research and scientific papers
Steric and Electronic Effects of Methyl Substitutents at the 2- and 6-Positions on N-Benzyl-1,4-dihydronicotinamide
Takeda, Jun,Ohta, Shigeru,Hirobe, Masaaki
, p. 2661 - 2667 (2007/10/02)
N-Benzyl-1,4-dihydronicotinamides having 2-methyl, 6-methyl and 2,6-dimethyl substituents were prepared and their reactivities toward an activated carbonyl compound (hexachloroacetone) were investigated.The reaction rates were especially enhanced for the
Coenzyme Models. Part 35. Charge Separation on the Micelle Surface as a Strategy to Prove the Multi-step Reaction Mechanism in NADH Model Reductions
Shinkai, Seiji,Tsuno, Takaharu,Asatani, Yukiko,Manabe, Osamu
, p. 1533 - 1540 (2007/10/02)
We have found that (i) the reaction of NADH model compounds with potassium persulphate (PPS) in anionic and non-ionic micelles initiates radical polymerisation of acrylamide and (ii) that reductive desulphonation of 2,4,6-trinitrobenzenesulphonate and 4-carboxy-2,6-dinitrobenzenesulphonate by NADH model compounds in deuterium oxide in the presence of the micelles gives 1,3,5-trinitrobenzene and 3,5-dinitrobenzoic acid, respectively, which contain 3-16percent deuterium.The results indicate that the reactions proceed through multi-step hydrogen transfer via radical ion-pair intermediates and the micelle is capable of dissociating the radical ion-pairs.
REDUCTION BY A MODEL OF NAD(P)H. 44. TRANSITION METAL CATALYZED REDUCTION OF ALLYLIC ACETATE
Nakamura, Kaoru,Ohno, Atsuyoshi,Oka, Shinzaburo
, p. 3335 - 3336 (2007/10/02)
Allylic acetates were reduced regioselectively to alkenes by a model of NAD(P)H via catalytic activation with transition metal complexes.
Kinetics of the Reduction of Isoquinolinium Cations by 1,4-Dihydronicotinamides
Bunting, John W.,Chew, Vivian S. F.,Chu, Gary
, p. 2303 - 2307 (2007/10/02)
The kinetics of the reduction of a series of 2-methyl-4-X-isoquinolinium cations and 2-methyl-5-X-phthalazinium cations by 1-benzyl-1,4-dihydronicotinamide (5) have been measured in 20percent CH3CN-80percent H2O (v/v) at pH 7, 25 deg C, and an ionic strength of 1.0.Pseudo-first-order rate constants (kobsd) show kinetic saturation at high concentrations of 4 (X = H and Br), and association constants of 2.1 and 1.5 M-1, respectively, have been evaluated for 1:1 complex formation.Interpretation of these data and earlier data for the reduction of the 2-methyl-5-nitroisoquinolinium cation (3) in terms of nonproductive complex formation leads to a linear free-energy relationship between the second-order rate constant (k2) for reduction and pKR+ for pseudobase formation by these cations: log k2 = -0.50pKR+ + 4.9.Substituent effects upon k2 for the reduction of 3 and 4 (X = CONH2, CN) by 1-benzyl-3-W-1,4-dihydropyridines (W = CN, CONH2, CONHCH3, CON(CH3)2) are similar to the substituent effects for cyanide ion dissociation from the corresponding 1-benzyl-4-cyano-3-W-1,4-dihydropyridines.The current study indicates that the relatively strong 1:1 complexes observed in the reduction of 5-nitroisoquinolinium cations by 1,4-dihydronicotinamides are nonproductive and also provides further evidence in support of a one-step hydride-transfer mechanism for these reactions.
