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By Jean Hladik, Michel Chrysos
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Note: The oxygen and sulfur atoms of phosphites and thiophosphites can engage in π-donor interactions causing upfield chemical shifts. If we substitute a carbon substituent of a tertiary phosphane by an amino group, we would expect a downfield shift simply because nitrogen is more electronegative than carbon. In Fig. 6 ppm downfield of most tertiary phosphanes. We note that all three phosphino amines depicted in Fig. 2 still have an NH functionality. We suspect that deprotonation will result in a further upfield shift.
0 NEt2 dibenzophosphole 37 Et O Et O P Et s c [ppm] O P O P O O Ph O O O Ph Ph P O Me P O O O P Ph O Ph O Ph O Me O O Me P Ph S Me Me P Ph S Ph P S S S Me Et P S S S Ph P S 150 Fig. 1 140 130 120 S S Et S S Et Ph Ph S S 110 δP[ppm] 31 P chemical shifts of a series of phosphites and thiophosphites than P), and in phosphites it operates on the oxygen atom (+I effect, since C is less electronegative than O). An increased electron density on oxygen results in a reduced electron withdrawing effect on phosphorus.
As the geometries of phosphaalkenes and phosphaalkynes are analogous to alkenes and alkynes, respectively, we can assume that the explanation given for the appearance of the carbon resonance in alkynes upfield from that for alkenes in 13C-NMR spectra is also applicable for the respective unsaturated phosphorus compounds. The resonance of the phosphorus signal in the 31P-NMR spectrum can be shifted downfield or upfield by changing the substituent on the carbon atom of the carbon phosphorus triple bond.