A new pentacoordinate ligand based on TPA (tris-(2-pyridylmethyl)amine), namely, N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-pyridine-2-carboxamide (PaPy3H), has been synthesized. The iron(III) complexes of this ligand, namely, [Fe(PaPy3)(CH3CN)] (ClO4)(2) (1), [Fe(PaPy3)(Cl)]ClO4 (2), [Fe(PaPy3)(CN)]ClO4 (3). and [Fe(PaPy3)(N3)]ClO4 (4), have been isolated and complexes 1-3 have been structurally characterized. These complexes are the first examples of monomeric iron(III) complexes with one carboxamido nitrogen in the first coordination sphere. All four complexes are low spin and exhibit rhombic EPR signals around g = 2. The solvent bound species [Fe(PaPy3)(CH3CN)](ClO4)(2) reacts with H2O2 in acetonitrile at low temperature to afford [Fe(PaPy3)(OOH)](+) (g = 2.24, 2.14, 1.96). When cyclohexene is allowed to react with H2O2 at room temperature, a significant amount oi cyclohexene oxide is produced along with the allylic oxidation products. Analysis of the oxidation products indicates that the allylic oxidation product, arise from a radical-driven autoxidation process while the epoxidation is carried out by a distinctly different oxidant. No epoxidation of cyclohexene is observed with 1/TBHP.