Abstract
A large number of triarylphosphines exhibiting different steric hindrance has been prepared. The pyramidalization angle α of these compounds was calculated with use of the MM2 force field and was shown to depend almost exclusively on the number of ortho substituents on the phenyl rings. In a series of isoteric (same α) phosphines, the oxidation potential correlates with the sum of the σ + Hammett parameters of the phenyl substituents. In the absence of oxygen, anodic oxidation of all the triarylphosphines bearing two o-methyl substituents on each phenyl ring is reversible and yields very persistent phosphoniumyl radicals. These radicals are easily detected by ESR in liquid solution and were shown to retain a pyramidal geometry that is significantly flattened compared to that of the parent phosphine
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