Kinetics and mechanism of naringenin reaction with Ce(IV) in different aqueous solutions of dimethylsulfoxide

Jabbari, Morteza; Gharib, Farrokh

doi:10.1002/kin.20585

Cited by 6 publications

(1 citation statement)

References 42 publications

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“…Ceric sulfate has been widely employed as an oxidant in the mechanistic studies in aqueous sulfuric acid medium [1][2][3][4][5][6][7][8] because of its stability and its availabil-ity. Cerium(IV) is less stable in aqueous nitric and perchloric acid solutions [9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Silver(I) and Copper(II) Catalysis for Oxidation of Histidine by Cerium(IV) in Acid Medium: A Comparative Kinetic Study

Fawzy

Althagafi

Altass

2017

Int. J. Chem. Kinet.

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The catalytic effect of silver(I) and copper(II) ions on the oxidation of histidine by cerium(IV) in aqueous sulfuric acid solutions was studied spectrophotometrically at a constant ionic strength of 3.0 mol dm−3 and at 25°C. In both uncatalyzed and metal ions‐catalyzed paths, the reactions exhibited first‐order kinetics with respect to [Ce(IV)] and [catalyst], and fractional first‐order dependences with respect to [His] and [H+]. The oxidation rates increased as the ionic strength and dielectric constant of the reactions media increased. The catalytic efficiency of Ag(I) was higher than that of Cu(II). Plausible mechanistic schemes for both uncatalyzed and catalyzed reactions were proposed, and the rate laws associated with the suggested mechanisms were derived. In both cases, the final oxidation products of histidine were identified as 2‐imidazole acetaldehyde, ammonium ion, and carbon dioxide. The activation parameters associated with the second‐order rate constants were evaluated.

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Section: Introductionmentioning

confidence: 99%

Silver(I) and Copper(II) Catalysis for Oxidation of Histidine by Cerium(IV) in Acid Medium: A Comparative Kinetic Study

Fawzy

Althagafi

Altass

2017

Int. J. Chem. Kinet.

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Electronic and solvent effects on kinetics of SNAr substitution reactions of substituted anilines with 2,6-bis(trifluoromethanesulfonyl)-4-nitroanisole in MeOH–Me2SO mixtures of varying composition: one reaction with two mechanistic pathways

2013

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The kinetics and mechanism of the aromatic nucleophilic substitution reactions of 2,6-bis(trifluoromethanesulfonyl)-4-nitroanisole with para-X-substituted anilines (X = OH, OMe, Me, H, F, I, Cl) were studied in MeOH–Me2SO mixtures and pure Me2SO at 25.0 °C. The second-order rate coefficients depend on the substitutent in aniline and give good Hammett and Brønsted correlations; a polar SNAr reaction is proposed for the reaction in different MeOH–Me2SO mixtures. The measured rate coefficients of the reaction demonstrated dramatic variations for aniline donor with the increasing dimethyl sulfoxide composition in MeOH–Me2SO mixtures. In this case, the Hammett and Brønsted plots are biphasic and concave upwards with a break point at 4-methylaniline. These results indicate a change in mechanism from the polar (SNAr) for less basic nucleophiles (X = 4-Cl, 4-I, 4-F, and H) to the single electron transfer (SET) for more basic nucleophiles (X = 4-OH, 4-OMe and 4-Me). The changes of the structure of the transitions states with substituents and solvent are in accordance with the results of kinetics studies. The solvation model described is well supported by the solvatochromism exhibited by aniline in the solvent mixture under investigation. These results provide an ideal framework for understanding the paramount importance of the specific molecular structure of solvent molecules in determining chemical reactivity versus solvent effects.Graphical abstractElectronic supplementary materialThe online version of this article (doi:10.1007/s00706-013-1030-7) contains supplementary material, which is available to authorized users.

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Combination of the most efficient promoter and micellar catalyst for rate enhancement of chromic acid oxidation on 2-butanol to 2-butanone conversion in aqueous media at room temperature

2015

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Kinetics and mechanism of naringenin reaction with Ce(IV) in different aqueous solutions of dimethylsulfoxide

Cited by 6 publications

References 42 publications

Silver(I) and Copper(II) Catalysis for Oxidation of Histidine by Cerium(IV) in Acid Medium: A Comparative Kinetic Study

Silver(I) and Copper(II) Catalysis for Oxidation of Histidine by Cerium(IV) in Acid Medium: A Comparative Kinetic Study

Electronic and solvent effects on kinetics of SNAr substitution reactions of substituted anilines with 2,6-bis(trifluoromethanesulfonyl)-4-nitroanisole in MeOH–Me2SO mixtures of varying composition: one reaction with two mechanistic pathways

Combination of the most efficient promoter and micellar catalyst for rate enhancement of chromic acid oxidation on 2-butanol to 2-butanone conversion in aqueous media at room temperature

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