Solubilization of n-alkylbenzenes into decanoyl-N-methylglucamide (Mega-10) solution.
Solubilization of benzene, toluene, ethylbenzene, n-propylbenzene, n-butylbenzene, n-pentylbenzene, and n-hexylbenzene into micelles of decanoyl-N-methylglucamide (Mega-10) was studied, where equilibrium concentrations of the above solubilizates were determined spectrophotometrically at 303.2 K. The concentration of the above solubilizates remained constant below the critical micelle concentration (cmc) and increased linearly with an increase in Mega-10 concentration above the cmc. The Gibbs free energy change of the solubilizates from the aqueous bulk to the liquid solubilizate phase was evaluated from the dependence of their aqueous solubility on the alkyl chain length of the solubilizates, which leads to -3.46 kJ mol-1 for DeltaG(0)(CH), the energy change per CH2 group of the alkyl chain. The first stepwise solubilization constant (K(overline)1 ) was evaluated from the slope of the change of solubilizate concentration versus Mega-10 concentration. The Gibbs free energy change (DeltaG(0,s)) for the solubilization decreased linearly with the carbon number of the alkyl chain of the solubilizates, from which DeltaG(0,s)(CH2) as evaluated to be -2.71 kJ mol-1. The similar values above clearly indicate that the location of the alkyl chain is a hydrophobic micellar core, which is also supported by the absorption spectrum of the solubilized molecules.
Nakamura
Shohei
S
Daiichi College of Pharmaceutical Sciences, 22-1 Tamagawamachi, Minami-ku, Fukuoka, Japan. snakamura@daiichi-cps.ac.jp
Kobayashi
Lisa
L
Tanaka
Ryo
R
Isoda-Yamashita
Teruyo
T
Motomura
Konomi
K
Moroi
Yoshikiyo
Y
D000473:Alkanes / Q000737:chemistry*; D000478:Alkylation; D001555:Benzene Derivatives / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D008823:Micelles; D012995:Solubility; D012996:Solutions / Q000737:chemistry; D013501:Surface-Active Agents / Q000737:chemistry*; D013816:Thermodynamics
D000473:Alkanes; D001555:Benzene Derivatives; D005227:Fatty Acids; D008823:Micelles; D012996:Solutions; D013501:Surface-Active Agents; C042221:decanoyl-N-methylglucamide; D005944:Glucosamine