The mechanism of electrohydrodimerization of chalcone on mercury from aqueous solutions

Moncelli, Maria Rosa; Nucci, Lamberto; Mariani, Palma; Guidelli, Rolando

doi:10.1016/0368-1874(85)85497-6

Cited by 25 publications

(7 citation statements)

References 11 publications

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“…Macroscale electrolysis was carried out in a conventional cell described in ref. (5). Cyclohex-2-en-1-one EHD was carried out both in a pH 9 borate buffer (0.16 mol dmp3 Na,B,O, + 0.68 mol dmd3 NaCl) at -1.6 V, where the coupling reaction takes place homogeneously, and in a pH 5 acetic buffer (1 mol dm-3 CH,CO,H+ 1 mol dm-3 CH,CO,Na) at -1.4 V, where the coupling reaction takes place mainly in the adsorbed state.…”

Section: Macroscale Electrolysismentioning

confidence: 99%

Mechanism of electrohydrodimerization of cyclohex-2-en-1-one on mercury from aqueous solutions. Part 1.—Results obtained in the absence of surfactants

Duarte¹,

Malanga²,

Nucci³

et al. 1988

J. Chem. Soc., Faraday Trans. 1

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The diffusion-controlled one-electron wave (wave I) due to cyclohex-2-en-1one (R) electroreduction on mercury from aqueous solutions in the range 2.5 < pH < 4 is shown to be consistent with the following mechanism : R + HA+ RH+ +A-where HA is a proton donor and the rate-determining coupling step (1 c), denoted by rds, proceeds in the adsorbed state. Double-potential-step chronocoulometric measurements indicate that R adsorption lies below the limits of sensitivity of the method, whereas R2H2 adsorption is appreciable at all potentials positive to -1.4 V us. SCE. The limiting current of wave I in the range 4 < pH < 6 is controlled by the protonation step (1 b), which is shown to proceed both heterogeneously and homogeneously. The contribution of the various proton donors, including adsorbed water, is pointed out. The diffusion-controlled one-electron wave (wave 11), which develops 4-2

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Section: Macroscale Electrolysismentioning

confidence: 99%

Mechanism of electrohydrodimerization of cyclohex-2-en-1-one on mercury from aqueous solutions. Part 1.—Results obtained in the absence of surfactants

Duarte¹,

Malanga²,

Nucci³

et al. 1988

J. Chem. Soc., Faraday Trans. 1

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“…It is a pleasure to emphasize here the importance of the contribution of Prof. Rolando Guidelli and his coworkers to the understanding of the mechanism of activated olefin electrodimerization under the very conditions where the Baizer-Monsanto reaction is carried out. We indeed learned much from their systematic study of the role of surfactants when the reaction is carried out in aqueous conditions, as it is on the industrial scale [25][26][27][28][29][30][31][32][33]. The first mechanistic investigations of the electrodimerization of activated olefins in non-aqueous media, where interfacial effects are minimized, pointed to the occurrence of the same radical-radical coupling mechanism as with the carbonyl compounds.…”

Section: Introductionmentioning

confidence: 98%

Dimerization of electrochemically generated ion radicals: mechanisms and reactivity factors

Costentin

Savéant

2004

Journal of Electroanalytical Chemistry

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“…When water was employed at the optimal concentration (5.5 M), two surprising products, including D1 and D2 , were formed. Electrochemistry of enones has been the subject of several publications. − Enones exhibit two cathodic peaks roughly around −0.90 and −1.70 V vs SHE in the absence of proton donors (a sample electrochemical behavior of these molecules that bear the enon moiety is shown in Figure S27). It was shown that the first cathodic event is due to the reduction of the activated double bond that affords a radical anion (one electron process).…”

Section: Resultsmentioning

confidence: 99%

Electrosynthesis of a Biaurone by Controlled Dimerization of Flavone: Mechanistic Insight and Large-Scale Application

et al. 2020

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The electrochemistry of flavone (1) has been carefully investigated at glassy carbon cathodes in dimethylformamide containing 0.10 M tetra-n-butylammonium tetrafluoroborate as supporting electrolyte. In this medium, a cyclic voltammogram for a reduction of 1 exhibits a reversible cathodic process (E pc = −1.58 V and E pa = −1.47 V vs SHE) that is followed by an irreversible cathodic peak (E pc = −2.17 V vs SHE). When water (5.0 M) is introduced into the medium, the first peak for 1 becomes irreversible (E pc = −1.56 V vs SHE), and the second (irreversible) peak shifts to −2.07 V vs SHE. Bulk electrolyses of 1 at −1.60 V vs SHE afford flavanone, 2′-hydroxychalcone, 2′-hydroxy-3-phenylpropionate, and two new compounds, namely (Z)-1,6-bis(2-hydroxyphenyl)-3,4-diphenylhex-3-ene-1,6-dione (D1) and (Z)-2,2′-(1,2-diphenylethene-1,2-bis(benzofuran-3(2H))-one) (D2), obtained in significant amounts, that were characterized by means of 1H and 13C NMR spectrometry as well as single-crystal X-ray diffraction. Along with the above findings, we have proposed a mechanism for the electroreduction of 1, which has been further corroborated by our quantum mechanical study.

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The mechanism of electrohydrodimerization of chalcone on mercury from aqueous solutions

Cited by 25 publications

References 11 publications

Mechanism of electrohydrodimerization of cyclohex-2-en-1-one on mercury from aqueous solutions. Part 1.—Results obtained in the absence of surfactants

Mechanism of electrohydrodimerization of cyclohex-2-en-1-one on mercury from aqueous solutions. Part 1.—Results obtained in the absence of surfactants

Dimerization of electrochemically generated ion radicals: mechanisms and reactivity factors

Electrosynthesis of a Biaurone by Controlled Dimerization of Flavone: Mechanistic Insight and Large-Scale Application

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