Reagent distribution and micellar catalysis of carbocation reactions

Bunton, Clifford A.; Carrasco, Nelson; Huang, Sung K.; Paik, Chang H.; Romsted, Laurence S.

doi:10.1021/ja00485a028

Cited by 120 publications

(43 citation statements)

References 17 publications

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“…The values for dissociations constants indicate a strong association, with the ion strongly incorporated into the kinetic micelle, which explains the catalytic effect of these surfactants. The difference between the catalytic activity of CBDAC and HTAB can be accounted for qualitatively, adopting the Bunton model [22]. The reaction rate increases as HO -ions bind stronger with the surfactant and displace the bromine ions from the double charged layer.…”

Section: Resultsmentioning

confidence: 99%

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Influence of surfactants on the fading of malachite green

et al. 2008

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Abstract:The kinetics of the reaction between malachite green (MG) and sodium hydroxide (MG fading) was studied using a spectrophotometric method in the presence of two cationic surfactants, cetyl-benzyl-dimethyl-ammonium chloride (CBDAC) and hexadecyl-trimethylammonium bromide (HTAB) and one anionic surfactant, sodium dodecyl sulphate (SDS) at concentrations below and above critical micellar concentrations. The cationic surfactants have a catalytic effect, while the anionic surfactant has an inhibitory effect on the reaction. A kinetic model describing the influence of surfactant on reaction rate was developed. The results are discussed on the basis of electrostatic and hydrophobic interactions between the kinetic micelles and malachite green.© Versita Warsaw and Springer-Verlag Berlin Heidelberg.

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Section: Resultsmentioning

confidence: 99%

“…The malachite green is very well incorporated into the anionic micelles and less in the cationic micelles [22]. In the presence of SDS, the malachite green loses its carbocationic character due to the incorporation into the anionic micelle; the total charge of the micelle is negative, so the approaching of HO -ion is restrained (4) …”

Section: Resultsmentioning

confidence: 99%

Influence of surfactants on the fading of malachite green

et al. 2008

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“…The value of for 3 V ϭ 0.14 dm m CTAB micelles (i.e., the volume of the Stern layer) as found by Bunton and coworkers [20]. However, the value of V m for non-ionic TX-100 was estimated by using an oblate ellipsoid [21,22] instead of a spherical micellar model [20].…”

Section: Generalmentioning

confidence: 90%

Kinetics of interaction of Histidine and Histidine Methyl Ester with Ninhydrin in micellar media

Kabir-ud-Din

Rafiquee

Akram

et al. 1999

Int. J. Chem. Kinet.

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Kinetics of the interaction of histidine and histidine methyl ester with ninhydrin under varying concentrations of reactants, anionic (sodium dodecyl sulphate, SDS), cationic (cetyltrimethylammonium bromide, CTAB) and non-ionic (Triton X-100, TX-100) micelles have been carried out. Rate of the reaction was found to be independent of the initial concentration of histidine (and histidine methyl ester) but was dependent on [Ninhydrin]. The SDS micelles had no effect on the rate of the reaction. In the presence of the CTAB micelles a small enhancement in the rate was observed. The profile showed that the increase in rate Ϫ [CTAB] [CTAB] increased the rate up to a maximum value and a further increase had a decreasing effect on the rate. The rate was enhanced by TX-100 also but, unlike CTAB micelles, TX-100 possessed a curve without peak for the profile. The following rate equation rate Ϫ [TX-100] was obeyed by the reaction in CTAB and TX-100 micelles:Values of k w , k m , and K S were evaluated and are reported herein.

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“…Substrate, S , is distributed between water and micelles, and can react in either medium (Scheme 2). In Scheme 2 sub- where [OH,-] is a molarity in terms of total solution volume and the second-order rate constant, kM, is written in terms of the mole ratio of micellar-bound OH-to micellar head groups [18]: …”

Section: Reactions In the Presence Of Surfactantsmentioning

confidence: 99%

Micellar effects upon the basic hydrolysis of 2,7‐bis(diethylamino)phenazoxonium chloride

Cuenca

1990

Int J of Chemical Kinetics

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The effect of cationic and anionic surfactants on the reaction of Basic Blue 3 (2,7-bis(diethylamino)phenazoxonium chloride, 1) with hydroxide ion has been studied. Cetyltrimethylammonium bromide (CTAB), cetyl and tetradecyltrimethylammonium chloride (CTAC and MTAC) enhance the rate of basic hydrolysis whereas sodium dodecyl sulfate (SDS) has an inhibitory effect. The extent of micellar catalysis is reduced by the addition of organic solvents. The results have been analyzed on the basis of the pseudophase ion-exchange model [l-31.

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Reagent distribution and micellar catalysis of carbocation reactions

Cited by 120 publications

References 17 publications

Influence of surfactants on the fading of malachite green

Influence of surfactants on the fading of malachite green

Kinetics of interaction of Histidine and Histidine Methyl Ester with Ninhydrin in micellar media

Micellar effects upon the basic hydrolysis of 2,7‐bis(diethylamino)phenazoxonium chloride

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