ortho-Phenyl dialkylphosphonium sulfonate compounds: two rotamers in equilibrium

Two known and two new ortho-phenyl phosphonium-sulfonate compounds have been synthesized and analyzed in solution and in the solid state. When the phosphonium moiety bears alkyl substituents, two rotamers are in equilibrium in solution. These two rotamers have been entirely characterized and are shown to differ by the spatial arrangement of the phosphonium proton relative to the sulfonate moiety. The phosphonium proton chemical shift and the (1)J(PH) coupling constant are characteristic values for each rotamer. The kinetic and thermodynamic constants have been determined by means of NMR and DFT studies.