60172-94-3

Upstream product

• 952-92-1 1-Benzyl-1,4-dihydronicotinamide 
• 17750-30-0 <4-(2)H>-1-benzyl-1,4-dihydronicotinamide 
• 13089-53-7 C₁₃H₁₂⁽²⁾HN₂O⁽¹⁺⁾*Cl^(1-) 
• 5096-13-9 1-benzylnicotinamide chloride 

Downstream Products

• 670-54-2 tetracyanoethylene anion 
• 16183-83-8 1-benzyl-3-carbamoylpyridinium ion 
• 99354-51-5 9-Deuterio-10-methyl-9-phenylacridan 
• 13089-53-7 C₁₃H₁₂⁽²⁾HN₂O⁽¹⁺⁾*Cl^(1-) 
• 63761-95-5 1-(4-cyanobenzyl)nicotinamide bromide 
• 91360-23-5 1-benzyl-3-carbamoylpyridinium-4-d anion 
• 56133-27-8 1-(4-cyanobenzyl)-1,4-dihydronicotinamide 

Relevant academic research and scientific papers

Effects of Base on Oxidation of an NADH Model Compound by Iron(III) Complexes and Tetracyanoethylene

Effects of base on both an electron-transfer reaction from an NADH model compound, 1-benzyl-1,4-dihydronicotinamide (BNAH) to (3+) (N-N = 2,2'-bipyridine and 1,10-phenanthroline) and a hydride transfer from BNAH to tetracyanoethylene (TCNE) in acetonitrile have been examined.The stoicheiometry of the electron transfer from BNAH to (3+) in the absence of a base indicates that BNAH is a one-electron donor.In the presence of a base, however, BNAH acts as an apparent two-electron donor, when the two-electron transfer proceeds via a multistep process; a fast one-electron transfer from BNAH to (3+) occurred, followed by the rate-determining deprotonation of BNAH+. by base and the subsequent fast electron transfer from BNA. to (3+).The rate constants for the proton transfer from BNAH+. to a series of pyridine derivatives have been determined.In the reduction of TCNE by BNAH, BNAH appears to be a two-electron donor in both the absence and presence of a base.Rates of the reduction of TCNE by BNAH increased with inceasing base concentration, suggesting the involvement of BNAH+. as an intermediate in the hydride transfer from BNAH to TCNE.The kinetic analyses have led to the evaluation of the proton transfer rate constants for the deprotonation of BNAH+. with various bases, which accord with those obtained from the electron-transfer reactions of BNAH with (3+) in the presence of bases.Based on the Broensted plot of the proton transfer rate constants as well as the variation of the primary kinetic isotope effects kH/kD with the pKa of the base, the pKa value for BNAH+. has been evaluated as 3.6 +/-0.4.

Donor-Acceptor Distance Sampling Enhances the Performance of "better than Nature" Nicotinamide Coenzyme Biomimetics

Understanding the mechanisms of enzymatic hydride transfer with nicotinamide coenzyme biomimetics (NCBs) is critical to enhancing the performance of nicotinamide coenzyme-dependent biocatalysts. Here the temperature dependence of kinetic isotope effects (

Electron- and hydride-transfer reactivity of an isolable manganese(V)-Oxo complex

The electron-transfer and hydride-transfer properties of an isolated manganese(V)-oxo complex, (TBP8Cz)MnV(O) (1) (TBP 8Cz = octa-tert-butylphenylcorrolazinato) were determined by spectroscopic and kinetic methods. The manganese(V)-oxo complex 1 reacts rapidly with a series of ferrocene derivatives ([Fe(C5H4Me) 2], [Fe(C5HMe4)2], and ([Fe(C 5Me5)2] = Fc*) to give the direct formation of [(TBP8Cz)MnIII(OH)]- ([2-OH] -), a two-electron-reduced product. The stoichiometry of these electron-transfer reactions was found to be (Fc derivative)/1 = 2:1 by spectral titration. The rate constants of electron transfer from ferrocene derivatives to 1 at room temperature in benzonitrile were obtained, and the successful application of Marcus theory allowed for the determination of the reorganization energies (λ) of electron transfer. The λ values of electron transfer from the ferrocene derivatives to 1 are lower than those reported for a manganese(IV)-oxo porphyrin. The presumed one-electron-reduced intermediate, a MnIV complex, was not observed during the reduction of 1. However, a MnIV complex was successfully generated via one-electron oxidation of the MnIII precursor complex 2 to give [(TBP8Cz)Mn IV]+ (3). Complex 3 exhibits a characteristic absorption band at λmax = 722 nm and an EPR spectrum at 15 K with gmax′ = 4.68, gmid′ = 3.28, and gmin ′ = 1.94, with well-resolved 55Mn hyperfine coupling, indicative of a d3 MnIVS = 3/ 2 ground state. Although electron transfer from [Fe(C 5H4Me)2] to 1 is endergonic (uphill), two-electron reduction of 1 is made possible in the presence of proton donors (e.g., CH3CO2H, CF3CH2OH, and CH3OH). In the case of CH3CO2H, saturation behavior for the rate constants of electron transfer (ket) versus acid concentration was observed, providing insight into the critical involvement of H+ in the mechanism of electron transfer. Complex 1 was also shown to be competent to oxidize a series of dihydronicotinamide adenine dinucleotide (NADH) analogues via formal hydride transfer to produce the corresponding NAD+ analogues and [2-OH]-. The logarithms of the observed second-order rate constants of hydride transfer (kH) from NADH analogues to 1 are linearly correlated with those of hydride transfer from the same series of NADH analogues to p-chloranil.

High-valent manganese(v)-oxo porphyrin complexes in hydride transfer reactions

Hydride transfer from dihydronicotinamide adenine dinucleotide (NADH) analogues to trans-dioxomanganese(v) porphyrin complexes proceeds via proton-coupled electron transfer, followed by rapid electron transfer. The Royal Society of Chemistry 2009.

Coenzyme Models. Part 43. New Metal-stabilized Radicals of a Flavin with a Fused Pyridine Moiety Which Serves also as a Metal Chelation Site in the Oxidised State.

A new flavin, 2,4,7-trimethyl-10-benzylquinopteridine-9,11(7H,10H)-dione (PyFl) has been synthesised which has within the molecule a flavin as a catalytic site and a fused pyridine as an additional metal-chelation site.Unlike conventional oxidised flavins lacking affinity with most metal ions, PyFl could associate with a variety of metal ions in acetonitrile.PyFl forms 1:1 complexes with ZnII, CdII, and CoII ions, the association constants being (1.4 - 4.4) x 105 M-1.These are the largest association constants reported for oxidised flavin-d-metal complexes.The oxidation of 1-benzyl-1,4-dihydronicotinamide (BNAH) by PyFl in acetonitrile, which did not take place in the absence of metal ion, was efficiently catalysed by several metal ions: II, ZnII, CdII, and SbIII>.Furthermore, the reaction with BNAH in the presence of MgII, ZnII, and CdII resulted in the formation of the flavosemiquinone which could be detected by absorption and e. s. r. spectroscopy.The e. s. r. spectral pattern is identical to that prepared by mixing equimolar amounts of oxidised and reduced PyFl.These results suggest that PyFl becomes even more electron-deficient than flavin owing to a PyFl metal charge transfer while the semiquinone is stabilised through the interaction with these metal ions.These flavin-metal interactions serve as a model system possibly relevant to the action of metalloflavoenzymes.Such reactions cannot be provided by using conventional flavins.

NAD(P)+-NAD(P)H Model.47. Mechanism of the Formation of 1,4-Dihydronicotinamide in the Reaction of Pyridinium Salt and Amine

An amine reduces 1-benzyl-3-carbamoylpyridinium ion (BNA)+ into 1-benzyl-1,4-dihydronicotinamide (BNAH) in aqueous solution.The mechanism of reduction has been elucidated.The covalently bound adduct of the amine and BNA+ at the 6-pos