Cyclodextrin-surfactant binding constant as driven force for uncomplexed cyclodextrin in equilibrium with micellar systems

Cepeda, Marjorie; Daviña, Rocío; García‐Río, Luis; Parajó, M.

doi:10.1016/j.cplett.2010.09.017

Cited by 17 publications

(15 citation statements)

References 15 publications

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“…In this context, we envisaged the use of cyclodextrins (CDs) to avoid the emulsion problem. It has already been shown that, depending on the nature of both the CD and the surfactant, CDs could interact with amphiphilic compounds 37–47. In fact, three different behaviors could be identified for CD/surfactant couples.…”

Section: Introductionmentioning

confidence: 99%

“…In that case, CDs adsorbed on the micelle surface because of hydrogen bonding between the carboxylate groups of the micelle components and the CD hydroxyle functions. García‐Río et al., for their part, showed that above the cmc, native or sulfobutyl ether β‐CD and sodium dodecyl sulfate co‐existed in water without interacting 46,47. Given the considerable haziness regarding the CD/surfactant interactions,48 we were interested in evaluating the effects of neutral and ionic β‐CDs in micellar organometallic catalysis.…”

Section: Introductionmentioning

confidence: 99%

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Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis

et al. 2012

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When mixed with a water-soluble phosphane capable of self-assembling into micelles, native or modified b-cyclodextrins (b-CDs) show very contrasting behavior depending on their neutral or ionic nature. In the post-micellar region, neutral b-CDs led to a micelle destructuring. Conversely, micelles remained stable over a well-defined range of ionic b-CD concentrations. In that case, the micelle destruction was only observed when using a large excess of ionic b-CDs. The catalytic performances of these micellar systems have been evaluated in a rhodium-catalyzed hydroformylation reaction of 1-decene. We showed that, using ionic b-CDs, the catalytic activity could be improved without a detrimental impact upon the regioselectivity. A linear/branched aldehyde ratio as high as 8.6 could be achieved. The best results were obtained with stoichiometric quantities of ionic randomly methylated b-CDs with respect to the phosphane with a beneficial effect on the decantation at the end of the reaction.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis

et al. 2012

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“…Garcia-Rio and coworkers have developed models that allow the computation of stability constants for CD-S host-guest association by measuring the rate constants of solvolysis of chemical probes, such as, crystal violet [28], 4-methoxybenzenesulfonil chloride [192], benzoyl chlorides [193], Nnitrososulfonamide [194] and m-nitrophenyl acetate [195].…”

Section: Accepted Manuscriptmentioning

confidence: 99%

The formation of host–guest complexes between surfactants and cyclodextrins

Valente

Söderman

2014

Advances in Colloid and Interface Science

183

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Cyclodextrins are able to act as host molecules in supramolecular chemistry with applications ranging from pharmaceutics to detergency. Among guest molecules surfactants play an important role with both fundamental and practical applications. The formation of cyclodextrin/surfactant host-guest compounds leads to an increase in the critical micelle concentration and in the solubility of surfactants. The possibility of changing the balance between several intermolecular forces, and thus allowing the study of, e.g., dehydration and steric hindrance effects upon association, makes surfactants ideal guest molecules for fundamental studies. Therefore, these systems allow for obtaining a deep insight into the host-guest association mechanism. In this paper, we review the influence on the thermodynamic properties of CD-surfactant association by highlighting the effect of different surfactant architectures (single tail, double-tailed, gemini and bolaform), with special emphasis on cationic surfactants. This is complemented with an assessment of the most common analytical techniques used to follow the association process. The applied methods for computation of the association stoichiometry and stability constants are also reviewed and discussed; this is an important point since there are significant discrepancies and scattered data for similar systems in the literature.In general, the surfactant-cyclodextrin association is treated without reference to the kinetics of the process. However, there are several examples where the kinetics of the process can be investigated, in particular those where volumes of the CD cavity and surfactant (either the tail or in special cases the head group) are similar in magnitude.This will also be critically reviewed.

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“…It should be noted that the signal broadening observed for phosphane protons suggested the presence of aggregates in the medium. Thus, though a 1/1 CD/phosphane mixture was used, phosphane-based aggregates and native β-CD/phosphane complexes coexisted in water in this concentration range [ 9 ]. In fact, the mixture of CD/phosphane complexes and aggregates was a consequence of the competitive equilibria of CD/phosphane complexation and phosphane self-assembly to form micelles.…”

Section: Resultsmentioning

confidence: 99%

Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis

Bricout¹,

Léonard²,

Len³

et al. 2012

Beilstein J. Org. Chem.

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SummaryIn this study, we showed that the addition of randomly modified β-cyclodextrin (RAME-β-CD) in aqueous medium could have a beneficial impact on the catalytic performances of phosphane-based aggregates in the Pd-catalyzed cleavage of allyl carbonates (Tsuji–Trost reaction). The RAME-β-CD/phosphane supramolecular interactions helped explain the catalytic results. The presence of RAME-β-CD in the aqueous compartment improved the phosphane-based aggregate dynamics. The exchanges between the hydrophobic substrate-containing aggregate core and the catalyst-containing aqueous phase were then greatly favored, resulting in an increase in the catalytic performances.

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Cyclodextrin-surfactant binding constant as driven force for uncomplexed cyclodextrin in equilibrium with micellar systems

Cited by 17 publications

References 15 publications

Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis

Cyclodextrin/Amphiphilic Phosphane Mixed Systems and their Applications in Aqueous Organometallic Catalysis

The formation of host–guest complexes between surfactants and cyclodextrins

Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis

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