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Intramolecular Hydrogen Bond Reverting the Solvent Effect on Phosphorus Hyperfine Coupling Constants of
Gérard Audran1, Lionel Bosco1, Paul Brémond1
1Aix Marseille Univ, CNRS, ICR, UMR 7273 case 541, Avenue Escadrille Normandie-Niemen, 13397, Marseille Cedex 20, France.
Abstract:
Recently, we reported a dramatic solvent effect on the phosphorus hyperfine coupling constant aP of β-phosphorylated six-membered ring nitroxides, that is, approximately 25 G of difference in aP from n-hexane to water (Org. Biomol. Chem. 2016, 14, -1228-1292). In this article, we report on the effect of intramolecular hydrogen bonding (IHB) in three nitroxides exhibiting IHB between the hydroxyl and diethylphosphoryl groups and one exhibiting IHB between the hydroxyl group and the nitroxyl moiety. It is observed that for the first three nitroxides, aP increases with increasing polarity/polarizability and hydrogen bond donor (HBD) properties of the solvent (π* and α, respectively)-in sharp contrast to the data reported in the literature-and for the last nitroxide, aP decreases with π* and α. In fact, the occurrence of IHB induces a large strain, its suppression by hydrogen bond acceptor (HBA) solvents affords an increase in aP .
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