The Journal of organic chemistry

Kinetics and mechanism of the oxygenation of potassium flavonolate. Evidence for an electron transfer mechanism

L Barhács, J Kaizer, G Speier

Index: Barhacs, Laszlo; Kaizer, Jozsef; Speier, Gabor Journal of Organic Chemistry, 2000 , vol. 65, # 11 p. 3449 - 3452

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Citation Number: 24

Abstract

The oxygenation of the potassium salt of flavonol (flaH) in absolute DMF leads to potassium O-benzoylsalicylate and carbon monoxide in 95% yield at 40° C. Kinetic measurements resulted in the rate law-d [flaK]/dt= k 2 [flaK][O2]. The rate constant, activation enthalpy, and entropy at 313.16 K are as follows: k 2/M-1 s-1=(3.28±0.10)× 10-1, Δ H⧧/kJ mol-1= 29±2, Δ S⧧/J mol-1 K-1=-161±6. The reaction fits a Hammett linear free energy relationship for 4'- ...