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Rates of solvolyses of 4-nitrophenyl phenyl thiophosphorochloridate (4-NO2PhOP(S)(Cl)OPh, 1) in ethanol, methanol, and aqueous binary mixtures incorporating ethanol, methanol, acetone, and 2,2,2-trifluroethanol (TFE) are reported. Thermodynamic parameters were determined at several temperatures in three representative solvents. The extended Grunwald-Winstein equation was applied to 29 solvents and the correlation coefficient (R) showed 0.959. The sensitivities (l = 1.37 and m = 0.62) are similar to those obtained for diphenyl thiophosphorochloridate ((PhO)2PSCl, 2), diphenyl phosphorochloridate ((PhO)2POCl, 3), diphenyl phosphinic chloride (Ph2POCl, 4), and diphenyl thiophosphinic chloride (Ph2PSCl, 5). The solvolytic reaction mechanism of 4-nitrophenyl phenyl thiophosphorochloridate (1) is suggested to be proceeded a SN2 process as previously reported result. The activation enthalpies are shown as slightly low as ∆H ≠ = 9.62 to 11.9 kcal·mol -1 and the activation entropies are shown as slightly high negative value as ∆S ≠ = ‒34.1 to ‒44.9 cal·mol -1 ·K -1 compared to the expected SN2 reaction mechanism. Kinetic solvent isotope effects are accord with a typical SN2 mechanism as shown in the range of 2.41 in MeOH/ MeOD and 2.57 in H2O/D2O solvent mixtures.

Kinetic Studies of the Solvolyses of 4-Nitrophenyl Phenyl Thiophosphorochloridate