Catalysis of nucleophilic substitutions by micelles of dicationic detergents

Bunton, Clifford A.; Robinson, Lawrence Baylor; Schaak, Jens; Stam, M. F.

doi:10.1021/jo00815a033

Cited by 231 publications

(149 citation statements)

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“…However these kind of surfactants were first studied by Bunton et al investigating their catalytic effects on nucleophilic substitutions [2]. Recently gemini surfactants have been subject of a extensive investigation because of their unique properties such as higher surface activity, improvements in the antibacterial activity and others potential applications which have been recently reviewed by Svenson [3], Zana [4] and Menger [5].…”

Section: Introductionmentioning

confidence: 99%

A fluorescence probe study of gemini surfactants in aqueous solution: a comparison between n-2-n and n-6-n series of the alkanediyl-a,w-bis (dimethylalkylammonium bromides)

B.S.

Tiera

2007

Eclet. Quím.

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Abstract:Two series of alkanediyl-a,w-bis (dimethylalkylammonium bromide (n-2-n and n-6-n; n=8, 10,12, and 16) have been synthesized and their micelles properties studied in aqueous solution using pyrene, pyrenecarboxaldehyde (PCA) and 1,8 anilinonaphtalene sulfonic acid sodium salt (ANS) as fluorescent probes. The micelles from these surfactants have been characterized on the basis of the information provided by micelle-solubilized fluorescent probes. The obtained results indicated that the surfactant concentration at which a marked decrease in l max parameter of pyrenecarboxaldehyde (PCA) occurs corresponds to the CMC determined by conductimetric measurements. Changes in the emission spectra of ANS and PCA observed in the submicellar range for both surfactants series (n-2-n and n-6-n) were interpreted as formation of pre-aggregates. It was found that the dimeric surfactants with long spacer (s= 6) form more hydrated aggregates when compared with those formed by the n-2-n and C n TAB surfactants series. This was attributed to a more difficult packing of n-6-n surfactant molecules to form micelles.

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Section: Introductionmentioning

confidence: 99%

A fluorescence probe study of gemini surfactants in aqueous solution: a comparison between n-2-n and n-6-n series of the alkanediyl-a,w-bis (dimethylalkylammonium bromides)

B.S.

Tiera

2007

Eclet. Quím.

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“…Changes in the molecular structure and type to improve upon their properties have attracted the attention of chemists (3)(4). This has led to the preparation of new generation surfactants such as geminis.…”

Section: Introductionmentioning

confidence: 99%

Anionic Gemini Surfactants: A Distinct Class of Surfactants

Shukla

Tyagi

2006

J. Oleo Sci.

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Anionic gemini surfactants are a new class of surfactants that comprise of two anionic head groups and two hydrophobic tails separated by a spacer group. Anionic gemini surfactants have low cmc values and show extraordinary surface activity. These surfactants have good water solubility and their ability to form micelles and lowering surface tension characteristics are fairly good as compared to conventional anionic surfactants. These surfactants have excellent lime soap dispersing ability (LSDA) too. Because of their higher surface activity these surfactants are used as promising surfactants in industrial detergency and emulsification. These surfactants are cost effective in area such as laundry detergent compositions, soil clean up, enhanced oil recovery and hydrotropic agents. This review deals with structure, synthesis, critical micelle concentration, surface active properties, performance properties, uses and biodegradability of anionic geminis.

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“…36 Gemini amphiphile (Figure 3a) molecules consist of two conventional surfactants connected by a flexible. 37 or rigid 38 spacer, which can be hydrophilic or hydrophobic.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of D- and L- isomers of Chiral Drugs for Improving their Bioavailability: Some Techniques Including Micellization with Gemini Surfactants

Singh¹,

Sharma²

2018

IJPER

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The enantiopure drugs are essential for disease treatment as the human body is amazingly chiral selective. Nearly 50% of drugs are chiral but the pharmacological activity resides with only one isomer, termed as eutomer, whereas the other isomer which is inactive or less potent metabolizes by a different way in the body. This toxic isomer in a racemic drug causes side-effects, genetic disorder or may cause even death if taken in high dosage. Therefore, role of stereochemistry in drug action getting more and more attention of medical practice and one should be good knowledge to make decisions regarding while using single enantiomer of any drug. Most of the drugs used in psychiatric practice are currently available in mixture of enantiomers. For some therapeutics, one particular isomer of chiral drug give better pharmacological results with respect to the target organ, bioavailability in body plasma, low toxicity etc., as compared to racemic mixture of that drug. This article explains the chirality of drugs, the stereochemistry of isomers of chiral drugs, emphasizes the difference in the potential biological and pharmacologic differences between the two enantiomers of a drug, and highlights the novel technique to increase the in-vivo solubility of particularly one isomer of drug, so that the bioavailability of eutomer can be enhanced. This can be done by used of surfactants, which encapsulate the enantiomers of drugs at different extend by micellization.

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Catalysis of nucleophilic substitutions by micelles of dicationic detergents

Cited by 231 publications

References 0 publications

A fluorescence probe study of gemini surfactants in aqueous solution: a comparison between n-2-n and n-6-n series of the alkanediyl-a,w-bis (dimethylalkylammonium bromides)

A fluorescence probe study of gemini surfactants in aqueous solution: a comparison between n-2-n and n-6-n series of the alkanediyl-a,w-bis (dimethylalkylammonium bromides)

Anionic Gemini Surfactants: A Distinct Class of Surfactants

Enantioseparation of D- and L- isomers of Chiral Drugs for Improving their Bioavailability: Some Techniques Including Micellization with Gemini Surfactants

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