Polychlorinated biphenyls are a class of persistent environmental contaminants, and micellar solubilization can be applied to remediate them. The intermolecular aggregates of biphenyl (BP) analogs and cetyltrimethyl ammonium bromide (CTAB) were studied by chemical shift perturbation, nuclear magnetic resonance (NMR) diffusometry, quantitative proton NMR, and nuclear Overhauser effect (NOE) spectroscopy to understand the structural determinants of their solubilization. The micelles of CTAB solubilized BPs readily, but its capacity depended strongly on the nature of the functional group (BPCH 2 OH > > BPCHO > BPCOOH ≈ BPCl ≈ BP). Upon internalization, the BPs diffused much slower, introduced significant low-frequency 1 H chemical shift changes for CTAB, and displayed strong intermolecular NOEs. The semiquantitative analysis of NOEs revealed further that the BPs are located in the palisade layer closer to the N + (CH 3 ) 3 head group, away from the hydrophobic core. 1 H NMR offers a simple high-throughput screening assay for evaluating and quantitating the solubilization of organics in micelles. The intermolecular NOEs and site-specific perturbation of chemical shifts add further insights on the location of solubilizates in micelles, which may be important for designing surfactants specific for environmental pollutants.

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