16183-83-8Relevant articles and documents
Interaction of Sulfur Dioxide with 1-Benzyl-1,4-dihydronicotinamide
Jarvis, William F.,Dittmer, Donald C.
, p. 2784 - 2786 (1983)
Anhydrous sulfur dioxide reacts rapidly with 1-benzyl-1,4-dihydronicotinamide to give a reduced species of sulfur dioxide, possibly HSO2(1-),which can be trapped by reaction with Michael acceptors to give sulfones.
Long-Lived C60Radical Anion Stabilized Inside an Electron-Deficient Coordination Cage
Baksi, Ananya,Clever, Guido H.,Hasegawa, Shota,Holstein, Julian J.,Kasanmascheff, Müge,Meichsner, Shari L.
, p. 9718 - 9723 (2021)
Fullerene C60 and its derivatives are widely used in molecular electronics, photovoltaics, and battery materials, because of their exceptional suitability as electron acceptors. In this context, single-electron transfer on C60 generates the C60???- radical anion. However, the short lifetime of free C60???- hampers its investigation and application. In this work, we dramatically stabilize the usually short-lived C60???- species within a self-assembled M2L4 coordination cage consisting of a triptycene-based ligand and Pd(II) cations. The electron-deficient cage strongly binds C60 by providing a curved inner ?-surface complementary to the fullerene's globular shape. Cyclic voltammetry revealed a positive potential shift for the first reduction of encapsulated C60, which is indicative of a strong interaction between confined C60???- and the cationic cage. Photochemical one-electron reduction with 1-benzyl-1,4-dihydronicotinamide allows selective and quantitative conversion of the confined C60 molecule in millimolar acetonitrile solution at room temperature. Radical generation was confirmed by nuclear magnetic resonance, electron paramagnetic resonance, ultraviolet-visible-near-infrared spectroscopy and electrospray ionization mass spectrometry. The lifetime of C60???- within the cage was determined to be so large that it could still be detected after one month under an inert atmosphere.
Ohkubo, Katsutoshi,Yamashita, Kohichi,Sakaki, Shigeyoshi
, p. 165 - 168 (1983)
Metal ion-catalyzed cycloaddition vs hydride transfer reactions of NADH analogues with p-benzoquinones
Fukuzumi,Fujii,Suenobu
, p. 10191 - 10199 (2001)
1-Benzyl-4-tert-butyl-1,4-dihydronicotinamide (t-BuBNAH) reacts efficiently with p-benzoquinone (Q) to yield a [2+3] cycloadduct (1) in the presence of Sc(OTf)3 (OTf = OSO2CF3) in deaerated acetonitrile (MeCN) at room temperature, while no reaction occurs in the absence of Sc3+. The crystal structure of 1 has been determined by the X-ray crystal analysis. When t-BuBNAH is replaced by 1-benzyl-1,4-dihydronicotinamide (BNAH), the Sc3+-catalyzed cycloaddition reaction of BNAH with Q also occurs to yield the [2+3] cycloadduct. Sc3+ forms 1:4 complexes with t-BuBNAH and BNAH in MeCN, whereas there is no interaction between Sc3+ and Q. The observed second-order rate constant (kobs) shows a first-order dependence on [Sc3+] at low concentrations and a second-order dependence at higher concentrations. The first-order and the second-order dependence of the rate constant (ket) on [Sc3+] was also observed for the Sc3+-promoted electron transfer from CoTPP (TPP = tetraphenylporphyrin dianion) to Q. Such dependence of ket on [Sc3+] is ascribed to formation of 1:1 and 1:2 complexes between Q?- and Sc3+ at the low and high concentrations of Sc3+, respectively, which results in acceleration of the rate of electron transfer. The formation constants for the 1:2 complex (K2) between the radical anions of a series of p-benzoquinone derivatives (X - Q?-) and Sc3+ are determined from the dependence of ket on [Sc3+]. The K2 values agree well with those determined from the dependence of kobs on [Sc3+] for the Sc3+-catalyzed addition reaction of t-BuBNAH and BNAH with X - Q. Such an agreement together with the absence of the deuterium kinetic isotope effects indicates that the addition proceeds via the Sc3+-promoted electron transfer from t-BuBNAH and BNAH to Q. When Sc(OTf)3 is replaced by weaker Lewis acids such as Lu(OTf)3, Y(OTf)3, and Mg(ClO4)2, the hydride transfer reaction from BNAH to Q also occurs besides the cycloaddition reaction and the kobs value decreases with decreasing the Lewis acidity of the metal ion. Such a change in the type of reaction from a cycloaddition to a hydride transfer depending on the Lewis acidity of metal ions employed as a catalyst is well accommodated by the common reaction mechanism featuring the metal-ion promoted electron transfer from BNAH to Q.
Coenzyme Models. Part 24. Micellar Catalysis of Flavin-mediated Reactions. Influence of the Flavin Structure on the Reactivity
Shinkai, Seiji,Kusano, Yumiko,Manabe, Osamu,Yoneda, Fumio
, p. 1111 - 1115 (1980)
The catalytic effect of a cationic (CTAB) micelle on the flavin-mediated oxidation of 1-benzyl-1,4-dihydronicotinamide (6), nitroethane carbanion (7), and thiophenol (8) is reported.The oxidation of (6) was subject to a small extent to micellar catalysis, whereas the oxidation of (7) and (8) which does not proceed in a simple aqueous solution was efficiently catalysed by the CTAB micelle.The rate of oxidation of (7) was profoundly dependent upon the structure of the flavin: flavins which have either a long alkyl group or a carboxy-group gave rate constants greater by 103-104 fold than unmodified flavin, and the rate constant for flavin (5) which has both groups was further enhanced (>106 fold).On the other hand, the oxidation of (8) was less affected by the change in the flavin structure.The reactivity order for the oxidation of (7) was (1) (unmodified neutral flavin) (2) (neutral flavin with a hexadecyl group) (4) (anionic flavin with a carboxy-group) (5) (anionic flavin with carboxy- and tetradecanoyl groups), whereas that for the oxidation of (8) was (1) (4) (2).The results indicate that the reactivity of flavins is variable, depending not only on the type of reaction but also on the environment.The results provide useful information on the versatile reactivity of flavin coenzymes bound to apoenzymes.
Bis-1,4-dihydronicotinamides. Intramolecular Electronic Interaction and Its Consequence in the Reduction of a Carbonyl Substrate in Aprotic Solvents
Murakami, Yukito,Aoyama, Yasuhiro,Kikuchi, Jun-ichi
, p. 444 - 446 (1981)
The reduction of hexachloroacetone in CH2Cl2 or CHCl3 was much enhanced in the presence of 1,6-bis(1-benzyl-1,4-dihydronicotinamido)hexane owing to an intramolecular electronic interaction of charge transfer character.
Micellar Effects on Photoinduced Electron Transfer from 1,4-Dihydronicotinamide Derivatives to Tris(acetylacetonato)cobalt(III)
Yamashita, Kohichi,Ishida, Hitoshi,Ohkubo, Katsutoshi
, p. 5204 - 5210 (1991)
The photoreduction of tris(acetylacetonato)cobalt(III) () by 1-benzyl-1,4-dihydronicotinamide (BNAH) and 1-dodecyl-1,4-dihydronicotinamide (DNAH) was performed with or without the surfactants anionic sodium dodecyl sulfate (SDS), anionic sodium
NON-STERIC STEREOCHEMISTRY SOLELY CONTROLLED BY ORIENTATION OF DIPOLAR FUNCTION
Ohno, Atsuyoshi
, p. 567 - 576 (1995)
The mechanism of biologically important (net) hydride transfer from NADH or NADPH to a substrate has been discussed from the viewpoint of physical organic chemistry.It is emphasized that the (net) hydride transfer involves an electron-transfer complex as
Micellar-accelerated Photoreduction of Tris(acetylacetonato)cobalt(III) by 1,4-Dihydronicotinamide Derivatives
Ohkubo, Katsutoshi,Yamashita, Kohichi,Sakaki, Shigeyoshi
, p. 787 - 788 (1984)
The photo-accelerated reduction of tris(acetylacetonato)cobalt(III) by 1,4-dihydronicotinamide derivatives (BNAH and DNAH) was considerably promoted by anionic micelles of sodium dodecylsulphate through the condensation (or incorporation) of the reductant
Generation and Reactivity of a One-Electron-Oxidized Manganese(V) Imido Complex with a Tetraamido Macrocyclic Ligand
Shi, Huatian,Xie, Jianhui,Lam, William W. Y.,Man, Wai-Lun,Mak, Chi-Keung,Yiu, Shek-Man,Lee, Hung Kay,Lau, Tai-Chu
supporting information, p. 12895 - 12899 (2019/09/13)
The synthesis and X-ray structure of a new manganese(V) mesitylimido complex with a tetraamido macrocyclic ligand (TAML), [MnV(TAML)(N-Mes)]? (1), are reported. Compound 1 is oxidized by [(p-BrC6H4)3N]+.[SbCl6]? and the resulting MnVI species readily undergoes H-atom transfer and nitrene transfer reactions.
