Abstract
New phosphoramidates with the formula RC(O)N(H)P(O)X(2), R = 2-NO(2)-C(6)H(4), 3-NO(2)-C(6)H(4) and 4-NO(2)-C(6)H(4), X = N(CH(2)CH(3)) (1)-(3), NC(4)H(8) (4)-(6), and NC(4)H(8)O (7)-(9) were synthesized and characterized by (1)H, (13)C, (31)P NMR and IR spectroscopy, and elemental analysis. The reaction of (9) with hydrated lanthanide(III) nitrate leads to ten- or nine-coordinated complexes, (10)-(13). The crystal structure has been determined for (3), (5), (9), (10) and (13). In contrast to all of the previously reported similar phosphoramidate compounds, the -C(O)-N(H)-P(O) skeleton in the free ligand (9) shows a cisoid conformation, with the C=O and P=O double bonds adopting a nearly syn conformation. Quantum chemical calculations were applied for clarifying this exceptional conformational behavior. The monodentate neutral ligand (9) is coordinated to the metal ions via the phosphoryl O atom, adopting the usual anti conformation between the C=O and P=O groups.
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