Inverse phase transfer catalysis: kinetics of the pyridine-1-oxide-catalyzed two-phase reactions of methyl-, methoxy-, iodo-, and nitro-benzoyl chlorides and benzoate ions

Lu, Yen Liang; Jwo, Jing‐Jer

doi:10.1016/s1381-1169(01)00076-0

Cited by 12 publications

(1 citation statement)

References 29 publications

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“…A specific application of CDs, which is related to the topic of this work, is their increased usage as inverse phase transfer catalysts (IPTC). − In this case, a hydrophobic reagent is transferred from the organic phase to the aqueous phase across the water/organic liquid interface, and the reaction takes place either in bulk water or at the aqueous side of the interface. This is essentially the reverse process of using crown ethers as normal phase transfer catalysts, a process which has received more attention. , The use of CDs as IPTC at the liquid/water interface provides exciting new opportunities for “green” organic synthesis, while also raising fundamental questions in the areas of heterogeneous catalysis, host–guest chemistry, and reactions in confined geometries.…”

Section: Introductionmentioning

confidence: 99%

β-Cyclodextrin at the Water/1-Bromobutane Interface: Molecular Insight into Reverse Phase Transfer Catalysis

Elk

Benjamin

2015

Langmuir

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Molecular insight into the role of β-cyclodextrin (βCD) as a phase transfer catalyst at the liquid/liquid interface is obtained by molecular dynamics simulations of the structure and dynamics of βCD adsorbed at the interface between water and 1-bromobutane. In particular, we consider the structure and dynamics of the water and bromobutane molecules inside the βCD cavity and compare them with the behavior when βCD is dissolved in bulk water. βCD is preferentially oriented at the interface, with the cavity opening along the interface normal. While in bulk water the cavity includes 6-8 water molecules that are relatively mobile with short residence time, at the interface the cavity is mostly dehydrated and includes a single bromobutane molecule. This inclusion complex is stable in bulk water. The implication of this behavior for reverse phase transfer catalysis is discussed.

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