Direct Detection of Radical Cations of NADH Analogues
- 14 November 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (49) , 14538-14539
- https://doi.org/10.1021/ja0272538
Abstract
The radical cation of an NADH analogue (BNAH: 1-benzyl-1,4-dihydronicotinamide) has been successfully detected as the transient absorption and ESR spectra in the thermal electron transfer from BNAH to Fe(bpy)33+ (bpy = 2,2‘-bipyridine). The ESR spectra of the radical cations of BNAH and the dideuterated compound (BNAH-4,4‘-d2) indicate that the observed radical cation is the keto form rather than the enol form in the tautomerization. The deprotonation rate and the kinetic isotope effects of the keto form of BNAH•+ were determined from the kinetic analysis of the electron-transfer reactions.Keywords
This publication has 25 references indexed in Scilit:
- Hydrogen-Transferred Radical Cations of NADH Model Compounds. 1. Spontaneous TautomerizationJournal of the American Chemical Society, 2000
- Electron-Transfer Kinetics for Generation of Organoiron(IV) Porphyrins and the Iron(IV) Porphyrin π Radical CationsJournal of the American Chemical Society, 1999
- Kinetics and Mechanism of the Oxidation of 10-Methyl-9,10-dihydroacridine by Chromium(VI,V,IV): Electron vs Hydrogen Atom vs Hydride TransferJournal of the American Chemical Society, 1998
- The Role of Homolytic Bond Dissociation Energy in the Deprotonation of Cation Radicals. Examples in the NADH Analogues SeriesJournal of the American Chemical Society, 1998
- NAD(P)+-NAD(P)H Models. 88. Stereoselection without Steric Effect but Controlled by Electronic Effect of a Carbonyl Group: Syn/Anti Reactivity Ratio, Kinetic Isotope Effect, and an Electron-Transfer Complex as a Reaction IntermediateJournal of the American Chemical Society, 1998
- Spontaneous Hydrogen Atom Transfer on Ionization: Characterization of Enol Radical Cations in Cryogenic MatricesAccounts of Chemical Research, 1997
- Mechanism of Electron Transfer Oxidation of 4-Substituted 1-Benzyl-1,4-dihydronicotinamidesChemistry Letters, 1996
- Formal hydride transfer from NADH analogs. 1-Benzyl-4-tert-butyl-1,4-dihydronicotinamide as a mechanistic probeJournal of the American Chemical Society, 1993
- An experimentally based family of potential energy surfaces for hydride transfer between NAD+ analogsJournal of the American Chemical Society, 1991
- Effects of base on oxidation of an NADH model compound by iron(III) complexes and tetracyanoethyleneJournal of the Chemical Society, Perkin Transactions 2, 1984