Kinetics and mechanism of the oxidation of acrylic acid and methyl methacrylate

Pozdeeva, N. N.; Денисов, Е. Т.

doi:10.1134/s0023158410020072

Cited by 5 publications

(1 citation statement)

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“…The intramolecular hydrogen bond of the phenol group is very strong. For instance, in phenolic crown ether the enthalpy of formation of this bond is -21 kJ mol -1 , and the concentration of free O-H groups is only 0.1% at 323 K 28. According to the theoretical cal culation performed by the DFT method,29 the difference ΔΔG ≠ 298K for two transition state for H atom abstraction by the methoxy radical from the O-H bond of ubiquinol bound by the hydrogen bond and the free one is 7.5 kJ mol -1 .…”

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Dissociation energies of O-H bonds in natural antioxidants

Denisova

Денисов

2008

Russ Chem Bull

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The dissociation energies of O-H bonds in natural antioxidants were estimated from the kinetic data (rate constants of reactions of the antioxidants with the peroxy radicals). The calculations were performed using the method of intersecting parabolas. α Tocopherol was used as a reference phenol with D O-H = 330 kJ mol -1 . The following groups of antioxidants were chosen for the estimation: tocopherols, their sulfur and selenium containing analogs, flavones, flavanones, and gallates. The discrepancy in the D O-H values for the same phenol by measure ments of k(RO 2 • + ArOH) of different authors does not exceed 2 kJ mol -1 . The D O-H values were calculated for 64 phenols.

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Dissociation energies of O-H bonds in natural antioxidants

Denisova

Денисов

2008

Russ Chem Bull

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Antioxidants in Chemistry and Biology

Valgimigli

Pratt

2012

Encyclopedia of Radicals in Chemistry, Biology and Materials

109

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Antioxidants are omnipresent in nature and industry; they are used to slow down the autoxidative degradation of both organic tissues and petroleum‐derived products. Various mechanisms by which antioxidants can act are known, the most common of which are introduced here. Since autoxidation is a radical chain reaction, radical‐trapping antioxidants play a particularly important role; therefore, we will discuss these compounds in most detail. To introduce and develop central concepts relating to this topic, we present kinetic and thermodynamic data obtained for the reactions of phenols, the archetypical radical‐trapping antioxidants, with chain‐carrying peroxyl radicals, and describe the means to obtain these data. We then extend our discussion to other important classes of radical‐trapping antioxidants, beginning with the closely related polyphenols and newly developed pyridinol and pyrimidinol antioxidants, and then further to aromatic amines, organosulfur compounds, and their derivatives. We go on to touch upon the synergistic behavior in antioxidant combinations, and the effects of the medium on these interactions, and finally round things up with a few more important biological examples: ascorbate and β‐carotene. A few comments on the state of the field and areas requiring further research and development are included.

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Catalytic and inhibition functions of iron ions in the chain oxidation of acrylic acid

Pozdeeva

Денисов

2011

Kinet Catal

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Kinetics and mechanism of the oxidation of acrylic acid and methyl methacrylate

Cited by 5 publications

References 3 publications

Dissociation energies of O-H bonds in natural antioxidants

Dissociation energies of O-H bonds in natural antioxidants

Antioxidants in Chemistry and Biology

Catalytic and inhibition functions of iron ions in the chain oxidation of acrylic acid

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