Reduction electrochimique de composes organiques en presence de tensio-actifs—III. Etude polarographique de l'acetophenone en milieux aqueux micellaires anionique, cationique et neutre

Honnorat, André; Martinet, Pierre

doi:10.1016/0013-4686(83)87002-9

Cited by 28 publications

(6 citation statements)

References 27 publications

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“…1 and in Scheme 1). In the case of acetophenone, this second wave lies in the potential range where the discharging of protons occurs in acidic medium (1). With TFMA, at a potential corresponding to wave A2, the reduction and the dimerization reactions are in competition and the same percentage of pinacols and carbinol is obtained (Table 3).…”

Section: Discussionmentioning

confidence: 94%

“…It is generally accepted that aromatic ketones are reduced according to the pH of the solution, with the formation of carbinol or pinacols in various amounts (1,20,21). The presence of a CF3 group in the TFMA causes a shift of half-wave reduction potentials to less negative values (AEl12 = 25 mV) (4), making the study in aqueous solution easier.…”

Section: Discussionmentioning

confidence: 99%

“…Previous papers from this laboratory have reported on the mechanism of electrochemical reduction of aromatic ketones derived from acetophenone in aqueous or in micellar medium (1,2) and in the presence of cyclodextrins (3). In particular, the dimerization reaction leading to diastereomeric pinacols has been investigated in these media.…”

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confidence: 99%

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Electrochemical and spectroscopic behavior of trifluoromethylacetophenone in aqueous and micellar medium

Liotier¹,

Mousset²,

Mousty³

1995

Can. J. Chem.

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The electrochemical behavior of 4-trifluoromethylacetophenone (TFMA) has been studied in aqueous (2 ≤ pH ≤ 10), micellar, and ethanolic solutions using polarographic techniques. A slow hydration process of the carbonyl group has been observed by means of polarography and UV–visible spectrophotometry. Besides the well-known pH dependence of the electroreduction of aromatic ketones, C—F bond cleavages concomitant to the ketone reduction occur under electrolysis conditions in alkaline medium (pH = 10) at a very negative potential (−1.7 V), leading to the formation of 4-methylacetophenone, which is reduced at this potential with formation of the carbinol and of symmetrical and dissymmetrical pinacols. Finally, the reduction of TFMA has been performed in the presence of chiral surfactants in order to test their ability to induce an asymmetric induction. Keywords: 4-trifluoromethylacetophenone, 4-methylacetophenone, electroreduction, micellar medium, chiral surfactants, hydration, C—F bond fission.

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Section: Discussionmentioning

confidence: 94%

Section: Discussionmentioning

confidence: 99%

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Electrochemical and spectroscopic behavior of trifluoromethylacetophenone in aqueous and micellar medium

Liotier¹,

Mousset²,

Mousty³

1995

Can. J. Chem.

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“…But it was still inside the scope of the data reported in the literatures by different methods such as conductometry and polargraphy, etc. 6,7,13,[29][30][31][32] It was a common phenomenon that different methods gave rise to different CMC values for the same surfactant. 33 These behaviors can be explained as follows: TPE is a lipophilic AIE compound, which is poorly soluble in water but highly soluble in organic solvents.…”

Section: Determination Of the Critical Micelle Concentrationmentioning

confidence: 99%

Aggregation-induced emission of tetraphenylethene derivative as a fluorescence method for probing the assembling/disassembling of amphiphilic molecules

Zhu

Pang

et al. 2011

Analyst

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The aggregation-induced emission (AIE) of a 1,2-diphenyl-1,2-di(p-tolyl)ethene (TPE) was explored as a novel fluorescence method for probing the assembling/disassembling of amphiphilic molecules. The fluorescence intensity was able to monitor the formation of micelles and determine the critical micelle concentration (CMC) of surfactants. The temperature-dependent micellization of the pharmaceutically important PEO-PPO-PEO copolymer, Pluronic F127, was further studied by using the TPE fluorescence spectrum intensity. Our results showed good agreement with those reported in the literature by using other methods. The special advantage of the AIE probe method was further explored to determine the assembling/disassembling process of the colored amphiphilic molecule, 1-[4-(3-phenylazophenoxy)butyl]triethylamine bromide (AzoC4), whose CMC value has not previously been described. Since the TPE fluorescence signal mainly comes from the aqueous phase, not from the inside of hydrophobic core, it provides a possible platform to study the CMC of those colored surfactants. Based on the novel fluorescence properties of TPE in the aggregated and dispersed states, one can conclude that the TPE method is a promising method for the determination of the CMC and critical micellization temperature (CMT), particularly having a special advantage to determine the assembling/disassembling process of colored amphiphilic molecules.

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“…Many researchers have studied the electroreduction of carbonyl compounds to monomeric and dimeric products using acetophenone and furfural as model molecules. The selectivity of electroreduction of acetophenone to the monomeric product 1-phenylethanol and the dimeric product 2,3-diphenyl-2,3-butanediol in aqueous media have been much studied [1][2][3][4][5][6][7] with interesting results. Likewise, in the presence of cyclodextrins, the dimeric product of electroreduction of acetophenone has also been obtained selectively [8][9][10].…”

Section: Introductionmentioning

confidence: 98%

Electrosynthesis of 2,3-dimethyltartaric acid from pyruvic acid in acid medium

et al. 2006

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This study reports the electrohydrodimerization of pyruvic acid to 2,3-dimethyltartaric acid in sulphuric acid medium (0.5 M H 2 SO 4 ) on a lead cathode. The main products detected were lactic acid and 2,3-dimethyltartaric acid. The selectivity towards the formation of 2,3-dimethyltartaric acid was studied vs. pyruvic acid concentration in sulphuric acid solution, at )1.1 V vs. MSE. The best selectivity of 2,3-dimethyltartaric acid reached 69% for an initial concentration of 1.7 M pyruvic acid. The yield of pyruvic acid was 84%.

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Reduction electrochimique de composes organiques en presence de tensio-actifs—III. Etude polarographique de l'acetophenone en milieux aqueux micellaires anionique, cationique et neutre

Cited by 28 publications

References 27 publications

Electrochemical and spectroscopic behavior of trifluoromethylacetophenone in aqueous and micellar medium

Electrochemical and spectroscopic behavior of trifluoromethylacetophenone in aqueous and micellar medium

Aggregation-induced emission of tetraphenylethene derivative as a fluorescence method for probing the assembling/disassembling of amphiphilic molecules

Electrosynthesis of 2,3-dimethyltartaric acid from pyruvic acid in acid medium

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