Conductometric and Potentiometric Studies of the Association of α-Cyclodextrin with Ionic Surfactants and Their Homologs

Satake, Iwao; Ikenoue, Tadashi; Takeshita, Tokuro; Hayakawa, Kou; Maeda, Tamaki

doi:10.1246/bcsj.58.2746

Cited by 112 publications

(57 citation statements)

References 14 publications

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“…Clearly, the order of binding with SPFO is P-CD > y-CD > a-CD with the last showing very little association at all. The intersection of the linear portions of the curves for the three cyclodextrins gives the stoichiometry of the main complex formed as 1: 1 in agreement with findings from other surfactant systems (3)(4)(5)(6)(7)(8). All pre-micellar SPFO solutions displayed the same behavior.…”

Section: Resultssupporting

confidence: 86%

“…Recent work has shown that fluorocarbon surfactants bind very strongly with P-CD (2, 3) with little tendency to form inclusates with a-CD (2). However, surfactant hydrocarbon chains of diameter 4.5 A apparently are readily accommodated within the a-CD cavity because stable complexes are formed with both a-CD and P-CD (3)(4)(5)(6)(7)(8). A complicating feature in the hydrocarbon chain situa-.…”

Section: Introductionmentioning

confidence: 99%

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Solution inclusion complexes of cyclodextrins with sodium perfluorooctanoate

Palepu¹,

Reinsborough²

1989

Can. J. Chem.

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RAMAMURTHY PALEPU and VINCENT C. REINSBOROUGH. Can. J. Chem. 67,1550Chem. 67, (1989. Pre-micellar and micellar sodium perfluorooctanoate solutions (SPFO) were examined conductometrically with added a-cyclodextrin (a-CD), P-cyclodextrin (P-CD), and y-cyclodextrin (y-CD). The order of stability of the 1: 1 inclusion complex was P-CD > y-CD > a-CD determined largely by the goodness of fit of the fluorocarbon chain in the CD cavity. Sodium ion electrode studies revealed that some ~a + ion is associated with the P-CD/SPFO complex. As shown by fluorine-19 nmr, P-CD girds the SPFO molecule snugly amidship with the terminal CF3 group still in solution. On the other hand, SPFO manages only a weak penetration of the fluorocarbon chain into the smaller a-CD cavity.

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Section: Resultssupporting

confidence: 86%

Section: Introductionmentioning

confidence: 99%

Solution inclusion complexes of cyclodextrins with sodium perfluorooctanoate

Palepu¹,

Reinsborough²

1989

Can. J. Chem.

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“…The association constants for the formation of a 1: 1 complex can be calculated with the equation given by Satake et al (4,5): …”

Section: Resultsmentioning

confidence: 99%

Surfactant–cyclodextrin interactions by conductance measurements

Palepu¹,

Reinsborough²

1988

Can. J. Chem.

141

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PALEPU and VINCENT C . REINSBOROUGH. Can. J. Chem. 66, 325 (1988). Conductance measurements were used to identify and to obtain association constants for the complexes formed between cyclodextrins (CD) with emphasis on P-cyclodextrin (PCD), and surfactants such as sodium dodecylsulfate (SDS) and tetradecyltrimethyl ammonium bromide. With both anionic and cationic surfactants, a C D forms predominantly a 2:l CD/surfactant complex while with both PCD and y C D the main species is I: 1. y C D binds much less strongly with surfactants than both a C D and PCD. Cyclodextrins destroy micelles by complexing the surfactant monomers more strongly than they are bound in self-association.RAMAMURTHY PALEPU et VINCENT C. REINSBOROUGH. Can. J. Chem. 66, 325 (1988) On a utilisk des mesures de conductance pour identifier et pour obtenir les constantes d'association des complexes qui se forment entre des cyclodextrines (CD) et des agents de surface, principalement entre la P-CD et le dodCcylsulfate de sodium (DSS), tant au-dessous qu'au-dessus de la concentration micellaire critique. Tant avec les agents de surface anioniques que cationiques, la a-CD forme principalement un complexe 2:l de CD:agent de surface; par ailleurs, les P-et y-CD forment principalement des complexes 1:l. La -y-CD se lie moins fortement que les a-et P-CD avec les agents de surface. Par comparaison avec leurs propres auto-associations, les cyclodextrines complexent avec les agents de surface monomkres plus fortement que les monomkres se complexent avec lui-m&mes et elles dCtruisent ainsi les micelles.[Traduit par la revue]

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“…It is observed that when CDs are added to an aqueous ionic surfactant solution, at constant surfactant concentration, an increase in CD concentration could result in a decrease in the experimental specific conductivity. This decrease can be ascribed to the formation of CD:Surfactant, CDS, inclusion complexes, which have considerably smaller ionic equivalent conductivity than those of surfactant monomers [27]. For this reason, conductivity measurements can be used in order to get information about ionic surfactants/CD interactions.…”

Section: Stoichiometrymentioning

confidence: 99%

Host-guest interactions between cyclodextrins and surfactants with functional groups at the end of the hydrophobic tail

Martı́n

Ostos

Angulo

et al. 2017

Journal of Colloid and Interface Science

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Graphical abstractIn this work the influence of the incorporation of aromatic substituents at the end of the hydrophobic tail on the binding of cationic surfactants to cyclodextrins was studied. 2 HOST-GUEST INTERACTIONS BETWEEN CYCLODEXTRINS AND SURFACTANTS WITH FUNCTIONAL GROUPS AT THE END AbstractThe aim of this work was to investigate the influence of the incorporation of substituents at the end of the hydrophobic tail on the binding of cationic surfactants to α-, β-, and -cyclodextrins. The equilibrium binding constants of the 1:1 inclusion complexes formed follow the trend K 1 (α-CD)>K 1 (β-CD)>>K 1 (-CD), which can be explained by considering the influence of the CD cavity volume on the host-guest interactions. From the comparison of the K 1 values obtained for dodecyltriethylammonium bromide, DTEAB, to those estimated for the surfactants with the substituents, it was found that the incorporation of a phenoxy group at the end of the hydrocarbon tail does not affect K 1 , and the inclusion of a naphthoxy group has some influence on the association process, slightly diminishing K 1 . This makes evident the importance of the contribution of hydrophobic interactions to the binding, the length of the hydrophobic chain being the key factor determining K 1 . However, the presence of the aromatic rings does influence the location of the host and the guest in the inclusion complexes. The observed NOE interactions between the aromatic protons and the CD protons indicate that the aromatic rings are partially inserted within the host cavity, with the cyclodextrin remaining close to the aromatic rings, which could be partially intercalated in the host cavity. To the authors´ knowledge this is the first study on the association of cyclodextrins with monomeric surfactants incorporating substituents at the end of the hydrophobic tail.

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Conductometric and Potentiometric Studies of the Association of α-Cyclodextrin with Ionic Surfactants and Their Homologs

Cited by 112 publications

References 14 publications

Solution inclusion complexes of cyclodextrins with sodium perfluorooctanoate

Solution inclusion complexes of cyclodextrins with sodium perfluorooctanoate

Surfactant–cyclodextrin interactions by conductance measurements

Host-guest interactions between cyclodextrins and surfactants with functional groups at the end of the hydrophobic tail

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