Micelle Catalyzed Hydrolysis of Carboxylic Acid Esters in Water–β‐Cyclodextrin–Cetyltrimethylammonium Bromide Systems

Xie, Juan; Zhang, Yi; Du, Juan; Zhang, Xiancheng; Liu, Yingjin; Yamamoto, Shunzo; Sueishi, Yoshimi

doi:10.1081/dis-120017948

Cited by 6 publications

(3 citation statements)

References 15 publications

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“…b-Cyclodextrin forms a complex with CTAB, but the micellar hydrolysis of esters is only influenced at high cyclodextrin concentrations. [106] Dorrego et al [107] found during investigations into the stoichiometry of various b-cyclodextrin-surfactant complexes that micelle formation in water also does not begin after complete complexation of the cyclodextrin, but rather that normal micelle formation competes with complexation.…”

Section: Solvolyses and Metalloenzyme Modelsmentioning

confidence: 97%

Reactions in Micellar Systems

2005

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The notion of "green chemistry" has encouraged even synthetic organic chemists to include water as a solvent. Incredible selectivities and activities can be achieved through the addition of amphiphiles with a defined structure. The morphology of supramolecular assemblies or associates formed by surfactants vary according to the temperature and concentration. As a rule, reactions are typically conducted using simple spherical aggregates, that is, micelles in the nanometer range. The strong polarity gradient present between the hydrophilic surface and the hydrophobic core of the micelle means that both nonpolar and polar reagents can be solubilized. This solubilization results in reactants becoming more concentrated within the micelle than in the surrounding water phase and leads to an acceleration of the reaction and causes selective effects. The kinetic treatment of reactions in micellar systems can be accomplished by considering them as microheterogeneous two-phase systems.

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Section: Solvolyses and Metalloenzyme Modelsmentioning

confidence: 97%

Reactions in Micellar Systems

2005

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“…Vor kurzem wurden Arbeiten publiziert, bei denen auf der Grundlage von micellar beschleunigten Esterhydrolysen der Einfluss von β‐Cyclodextrinen auf Micellsysteme geprüft wurde. β‐Cyclodextrin bildet mit CTAB einen Komplex, aber die micellare Hydrolyse von Estern wird erst bei hohen Cyclodextrin‐Konzentrationen beeinflusst 106. Dorrego et al107 fanden bei Untersuchungen der Stöchiometrie unterschiedlicher β‐Cyclodextrin‐Tensid‐Komplexe, dass die Micellbildung in Wasser nicht erst nach der vollständigen Komplexierung der Cyclodextrine beginnt, sondern dass die reguläre Micellbildung mit der Komplexierung konkurriert.…”

Section: Reaktionen In Micellenunclassified

Reaktionen in micellaren Systemen

2005

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Die Vorstellung einer “grünen Chemie” hat selbst den präparativ arbeitenden Organiker ermutigt, Wasser als Lösungsmittel in Betracht zu ziehen. Durch Zusätze von Amphiphilen bestimmter Struktur kann man erstaunliche Aktivitäten und Selektivitäten erzielen. Die von den Tensiden gebildeten Assoziate variieren in ihrer Morphologie je nach Temperatur und Konzentration. In der Regel arbeitet man im Bereich einfacher sphärischer Aggregate, der nanometergroßen Micellen. Da in Micellen ein starker Polaritätsgradient von der hydrophilen Oberfläche zum hydrophoben Kern vorliegt, können sowohl unpolare als auch polare Reaktanten solubilisiert werden. Dadurch kommt es oft im Vergleich zur umgebenden Wasserphase zu einer Konzentrierung der Reaktionspartner und damit zu einer Beschleunigung der Reaktion. Darüber hinaus treten selektive Effekte auf. Micellare Systeme können kinetisch als mikroheterogene Zweiphasensysteme behandelt werden.

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“…Investigations of the catalytic activity of enzyme mimics by both chemists and biologists, have helped to understand the functions of the metal ions and ligands in natural enzymes. 2,3 Previous studies [4][5][6][7][8][9][10][11][12] on the catalytic hydrolysis of phosphate esters to mimic hydrolytic metalloenzymes involved a large number of complexes of such metal ions as Co 3+ , Ir 3+ , Cu 2+ , Zn 2+ , Co 2+ , Ni 2+ , Pd 2+ , Pt 2+ and La 3+ etc., and ligands with such electron donating atoms as N and O. The studies of Schneider et al 13 and Roigk et al 14 showed that complexes with transition metal ions laying in a crown ring are catalytically effective for phosphatic diester hydrolysis.…”

mentioning

confidence: 99%

Hydrolysis of phosphate diester catalysed by transition metal complexes of a salicylaldimine Schiff base bearing dibenzo-18-crown-6

Zhang

Xie

Tang

et al. 2005

Journal of Chemical Research

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A new crowned Schiff base ligand and its cobalt(II) and manganese(III) complexes were synthesised and characterised. These complexes were used to catalyse the hydrolysis of bis(4-nitrophenyl) phosphate (BNPP) in order to mimic the action of hydrolytic metalloenzymes. The kinetics and the mechanism of the titled reactions were investigated. The change of the characteristic ultraviolet spectra of the reaction systems was also analysed. A kinetic mathematical model of BNPP cleavage catalysed by the complexes is proposed. The function of the crown ether ring and the effects of the reaction conditions on the catalytic hydrolysis of BNPP are discussed.

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Micelle Catalyzed Hydrolysis of Carboxylic Acid Esters in Water–β‐Cyclodextrin–Cetyltrimethylammonium Bromide Systems

Cited by 6 publications

References 15 publications

Reactions in Micellar Systems

Reactions in Micellar Systems

Reaktionen in micellaren Systemen

Hydrolysis of phosphate diester catalysed by transition metal complexes of a salicylaldimine Schiff base bearing dibenzo-18-crown-6

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