Solubilization Site of Organic Perfume Molecules in Sodium Dodecyl Sulfate Micelles: New Insights from Proton NMR Studies.
The site of incorporation of solubilizates in sodium dodecyl sulfate (SDS) micellar systems has been investigated by proton NMR spectroscopy. The solubilizate molecules chosen for the present study are phenol, 4-methylphenol, 4-allyl-2-methoxyphenol, anisole, 4-methylanisole, 4-propenylanisole, 1,8-cineole, and limonene. These molecules possess a wide variety of functional groups with different degrees of hydrophilic/hydrophobic character and are thereby solubilized at different micellar locations. Aromatic compounds, especially those having a phenolic-OH group, showed a large upfield shift of SDS methylene protons that are closely linked to the terminal sulfate groups. Additionally, in the case of phenolic compounds, the unresolved signals of the nine straight-chain bulk methylene protons of SDS are split into a broad doublet with uneven intensity. This splitting of methylene protons was found to be dependent on the concentration of the substrate. Based on these observations, probable solubilization sites and orientation of the substrate molecule within the micelles are discussed. Phenolic compounds, being the most hydrophilic among the present set, reside at the hydrophilic/hydrophobic boundary of micelle-water interface and thus influence the resonances of SDS protons the most. Aromatic methoxy and aliphatic compounds, being relatively more hydrophobic in nature, reside inside the micellar core and thereby result in smaller shifts. Copyright 2000 Academic Press.
Suratkar
V
Unilever Research India, I.C.T. Link Road, Andheri (East), Mumbai, 400 099, India
Mahapatra
S