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DOI: 10.1039/A702474F (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1997, 2507-2512

Spin-trapping of free radicals by PBN-type β-phosphorylated nitrones in the presence of SDS micelles[hair space]†

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Cécile Rizzi, Robert Lauricella, Béatrice Tuccio, Jean-Claude Bouteiller, Viviane Cerri and Paul Tordo

Abstract

Three PBN-type β-phosphorylated nitrones, PPN 1, 4-PyOPN 2, and 4-ClPPN 3, have been used to trap two carbon centred free radicals, CH3˙ and CO2˙–, in a water–SDS biphasic system. The location of the traps and their adducts has been found by EPR spectroscopy. 4-PyOPN is found to remain in water, while 4-ClPPN is preferentially sequestered into the micellar structure, and PPN partitioned between the two phases. With the three nitrones, the CO2˙– spin adduct always remains in the bulk aqueous phase. In contrast, the three CH3˙ spin adducts seem to be present in both phases. However, 4-PyOPN-CH3 is essentially located in water, and 4-ClPPN–CH3 in the micelles, while PPN–CH3 is clearly shown to partition between the aqueous environment and the micellar interior. For all these spin adducts, the phosporus hyperfine splitting constant, aP, is found to be a good indicator of aminoxyl behaviour in the presence of micelles. For the various sodium dodecyl sulfate concentrations, the PPN–CH3 affinity for the micellar phase was evaluated from the average aP value.

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