SUBSTITUENT EFFECTS OF PHOSPHORUS-CONTAINING GROUPS. THE ELECTRONIC EFFECTS IN ANILIDES AND PHENYL ESTERS |
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| Authors: | Tomasz A Modro |
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| Institution: | Department of Chemistry , University of Toronto , Toronto , Ontario , Canada , M5S 1A1 |
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| Abstract: | Abstract 13C NMR shielding parameters have been determined for the N-phosphorylated aniline and O-phosphorylated phenol derivatives, Ph–Y–P(O)Z2 (Y=NH, O), and for their complexes with titanium tetrachloride. Inductive and resonance substituent constants were calculated using the dsp approach for the neutral and charged substituents. The results are compared with those for the corresponding neutral and charged acetyl derivatives. Shielding effects and substituent constants are discussed in terms of the interactions of the lone pair at Y with the aromatic ring and with the acyl center. It is concluded that no significant p π-d π back-donation from Y to the phosphorus atom operates in the systems studied. |
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