The mapping Φ n (A, B) = AB − BA, where the matrices A, B ∈ C 2n×2n are skew-Hamiltonian with respect to transposition, is studied. Let C n be the range of Φ n : we give an implicit characterization of C n , obtaining results that find an application in algebraic geometry. Namely, they are used in [R. Abuaf and A. Boralevi, Orthogonal bundles and skew-Hamiltonian matrices, In Preparation] to study orthogonal vector bundles. We also give alternative and more explicit characterizations of C n for n ≤ 3. Moreover, we prove that for n ≥ 4 the complement of C n is nowhere dense in the set of 2n-dimensional Hamiltonian matrices, denoted by H n , implying that almost all matrices in H n are in C n for n ≥ 4. Finally, we show that Φ n is never surjective as a mapping from W n × W n to H n , where W n is the set of 2n-dimensional skew-Hamiltonian matrices. Along the way, we discuss the connections of this problem with several existing results in matrix theory.