Aggregation Behavior and Thiol-Thioester Exchange for Cationic Surfactants with Propylthioacetate Side Chain

Journal of Oleo Science
Tsuyoshi AsakawaHitoshi Asakawa

Abstract

A series of cationic surfactants containing the thioacetate group, [CnH2n+1N(CH3)2(CH2)3SCOCH3] Cl (Cn3SAc, n = 12, 14, 16), were prepared and their properties in aqueous solution were investigated by conductivity, fluorescence, and dynamic light scattering measurements. The critical micelle concentrations (CMCs) of Cn3SAc decreased to about half the value of the corresponding alkyltrimethylammonium chloride. Thioacetate was eliminated with the addition of dithiothreitol (DTT) as well as NaOH. HPLC (high performance liquid chromatography) analysis and NMR (nuclear magnetic resonance) spectroscopy showed that thiol surfactants, [CnH2n+1N(CH3)2(CH2)3SH]Cl (Cn3SH), were generated upon the addition of DTT in aqueous solution via thiol-thioester exchange, whereas gemini surfactants, [CnH2n+1N(CH3)2(CH2)3SS(CH2)3N(CH3)2CnH2n+1]2Cl (2Cn3SS), were generated upon incubation in alkaline solution via hydrolysis and air oxidation.

References

Apr 12, 2000·Biochemistry·W J WedemeyerH A Scheraga
Sep 10, 2004·Journal of the American Chemical Society·Matthew G Woll, Samuel H Gellman
Apr 19, 2005·Chemical Communications : Chem Comm·Julien LeclaireJeremy K M Sanders
Jun 28, 2006·Langmuir : the ACS Journal of Surfaces and Colloids·Tsuyoshi AsakawaShigeyoshi Miyagishi
Mar 12, 2008·Journal of Oleo Science·Tsuyoshi AsakawaShigeyoshi Miyagishi
Mar 25, 2010·Organic Letters·Soumyadip GhoshMarcey L Waters
Oct 8, 2011·The Journal of Physical Chemistry. a·Chein-Wei Fu, Thy-Hou Lin

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Citations

May 17, 2019·Journal of Oleo Science·Tsuyoshi AsakawaHitoshi Asakawa

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