Abstract
The reaction of p-acetylaniline with chlorodiphenylphosphine afforded the new ligand (p-CH3CO)C6H4N(H) PPh2 (1) in good yield. Monooxidized thioxo (p-CH3CO)C6H4N(H)P(S)Ph-2 (2) and selenoxo (p-CH3CO)C6H4N (H)P(Se)Ph-2 (3) were synthesized by the reaction of 1 with elemental sulfur or grey selenium. Compounds 1-3 were identified and characterized by multinuclear NMR spectroscopy (H-1, C-13, P-31, Se-77 NMR) and elemental analysis. Compounds 2 and 3 were structurally characterized by single crystal X-ray diffraction which showed that the p-acetyl substituent on the aniline aromatic ring has a profound influence on the elongation of the P-N bond distance compared to several structurally characterized analogues found in literature. As such, subsequent reactions involving the P-N bond (i.e. insertion reactions) may be influenced in a favorable manner and proceed with ease.