Basic hydrolysis of crystal violet in beta-cyclodextrin/surfactant mixed systems.
The basic hydrolysis of crystal violet (CV) in mixed systems consisting of beta-cyclodextrin (beta-CD) and a micelle-forming surfactant, cetyltrimethylammonium chloride (CTACl), has been studied. beta-CD was found to catalyze the basic hydrolysis of CV through the interaction of its hydroxyl group, in its deprotonated form, with the carbocation in the complexed substrate. The addition of small amounts of CTACl, with [CTACl] below the critical micelle concentration, to beta-CD solutions does not have an effect upon the observed rate constant for the basic hydrolysis of CV. This behavior is different from that observed for the alkaline hydrolysis of N-methyl-N-nitroso-p-toluenesulfonamide and nitrophenyl acetates in mixed beta-CD/cationic surfactant systems. The proposed mechanism allows us to explain the experimental results on the basis of the high percentage of uncomplexed beta-CD in equilibrium with the micellar system, the low CV concentration, and the high value for the binding constant of CV by beta-CD.
García-Río
L
L
Departamento de Química Física, Facultad de Químicia, Universidad de Santiago de Compostela, Santiago de Compostela, Spain.
Leis
J R
JR
Mejuto
J C
JC
Navarro-Vázquez
A
A
Pérez-Juste
J
J
Rodriguez-Dafonte
P
P
D001665:Binding Sites; D000077286:Cetrimonium; D002593:Cetrimonium Compounds; D005840:Gentian Violet / Q000737:chemistry*; D006868:Hydrolysis; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008823:Micelles; D009574:Nitro Compounds / Q000737:chemistry; D009603:Nitroso Compounds / Q000737:chemistry; D010648:Phenylacetates / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry*; D047392:beta-Cyclodextrins / Q000737:chemistry*
D002593:Cetrimonium Compounds; D008823:Micelles; D009574:Nitro Compounds; D009603:Nitroso Compounds; D010648:Phenylacetates; D013449:Sulfonamides; D013501:Surface-Active Agents; D047392:beta-Cyclodextrins; D005840:Gentian Violet; D000077286:Cetrimonium