N-H activation in N-nitropropionamide: coordination chemistry of a primary nitroamide.

N-nitropropionamide, EtC(O)NHNO(2), oxidatively adds to Ir(Cl)(N(2))(PPh(3))(2) to give a η(2)-(N,O)-N-nitropropionamide anion bound to an Ir hydride complex. Single-crystal X-ray diffraction of the product indicates that it forms an unusual O-bound chelate through the nitro group. Density functional calculations for a model nickel complex, [Ni(MeC(O)NNO(2))(CN)(2)](-), are used to help distinguish the observed IR bands for the four possible conformations and binding geometries of this ligand.