Thermodynamics and Kinetics Superiorities of 1,4-Dihydronicotinamide as the Activation Center of NADH

Chem. J. Chinese Universities

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Thermodynamics and Kinetics Superiorities of 1,4-Dihydronicotinamide as the Activation Center of NADH

JIAO Xiao-Yun, TAN Yue, ZHU Xiao-Qing*, CHENG Jin-Pei

State Key Laboratory of Elemento-organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071, China

Received:2007-10-22 Revised:1900-01-01 Online:2008-07-10 Published:2008-07-10
Contact: ZHU Xiao-Qing

Abstract

Abstract: Two series of substituted phenyl-1,4-dihydronicotinamide and their 1,2-dihydroisomers as NADH models were synthesized. The reaction heats and activation parameters of the hydride transfer from the NADH models to N-methylacridinium cation were determined. The results show that the thermodynamic driving force of the hydride transfer from the 1,2-dihydro-NADH models is larger than that of the hydride transfer from the corresponding 1,4-dihydro-NADH models, but the former has quite large positive activation entropy change, which makes the activation free energy change of the former reactions become higher than that of the latter reactions. When the thermodynamics and kinetics on the hydride reverse transfers were examined, the results show that neither thermodynamics nor kinetics are favorable for the hydride transfer to the 2-position of the PNA+, the main reason is that the hydrogen atom has larger steric hindrance at 2-position than that at the 4-position.

Key words: 1,4-Dihydro NADH models, 1,2-Dihydro NADH models, N-Methylacridinium cation, Hydride transfer reaction, Thermodynamics, Kinetics

CLC Number:

O621

TrendMD:

JIAO Xiao-Yun, TAN Yue, ZHU Xiao-Qing*, CHENG Jin-Pei. Thermodynamics and Kinetics Superiorities of 1,4-Dihydronicotinamide as the Activation Center of NADH[J]. Chem. J. Chinese Universities, doi: .

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Thermodynamics and Kinetics Superiorities of 1,4-Dihydronicotinamide as the Activation Center of NADH

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