TY - JOUR
T1 - Acid-catalysed reduction of p-benzoquinone derivatives by an NADH analogue, 9,10-dihydro-10-methylacridine. The energetic comparison of one-electron vs. two-electron pathways
AU - Fukuzumi, Shunichi
AU - Ishikawa, Masashi
AU - Tanaka, Toshio
PY - 1989
Y1 - 1989
N2 - The energetic comparison of one-electron vs. two-electron pathways has been made for the acid-catalysed reduction of a series of p-benzoquinone derivatives (Q) by an NADH analogue, 9,10-dihydro-10-methylacridine (AcrH2), in aqueous solutions (H2O-EtOH; 5:1 v/v) at 298 K. The pH dependences of the second-order rate constants (log kobs) as well as the primary kinetic isotope effects (kH/kD) for tne acid-catalysed reduction of Q by AcrH2 have been correlated well with the pH dependences of the one-electron reduction potentials of p-benzoquinone derivatives. On the other hand, no direct correlation of log kobs or kH/kD with the corresponding two-electron reduction potentials has been observed. Mechanisms of the acid-catalysed hydride transfer reactions from AcrH2 to Q have been discussed based on the energetic comparison of one-electron vs. two-electron pathways.
AB - The energetic comparison of one-electron vs. two-electron pathways has been made for the acid-catalysed reduction of a series of p-benzoquinone derivatives (Q) by an NADH analogue, 9,10-dihydro-10-methylacridine (AcrH2), in aqueous solutions (H2O-EtOH; 5:1 v/v) at 298 K. The pH dependences of the second-order rate constants (log kobs) as well as the primary kinetic isotope effects (kH/kD) for tne acid-catalysed reduction of Q by AcrH2 have been correlated well with the pH dependences of the one-electron reduction potentials of p-benzoquinone derivatives. On the other hand, no direct correlation of log kobs or kH/kD with the corresponding two-electron reduction potentials has been observed. Mechanisms of the acid-catalysed hydride transfer reactions from AcrH2 to Q have been discussed based on the energetic comparison of one-electron vs. two-electron pathways.
UR - http://www.scopus.com/inward/record.url?scp=37049073463&partnerID=8YFLogxK
U2 - 10.1039/p29890001811
DO - 10.1039/p29890001811
M3 - Article
AN - SCOPUS:37049073463
SN - 1472-779X
SP - 1811
EP - 1816
JO - Journal of the Chemical Society. Perkin Transactions 2
JF - Journal of the Chemical Society. Perkin Transactions 2
IS - 11
ER -