Synthesis and Structure of α-Aminophosphate and Its Interaction with DNA/BSA

The reaction of terephthalaldehyde, p-chloroaniline, and diethyl phosphite in ethyl alcohol solution yields a new crystal (1), CCDC:1405044. This compound is characterized by X-ray single-crystal diffraction, IR, elemental analysis, ESI-MS, and ¹H and ¹³C NMR. Compound 1 crystallizes in the triclinic system, space group P-1 with a = 11.0444(4) Å, b = 12.6468(4) Å, c = 12.7657(4) Å, V = 1627.46(9) ų, Z = 2, C₂₈H₃₆Cl₂N₂O₆P₂, M_r = 629.43, D_c = 1.284 g/cm³, μ = 0.339 mm^–1, F(000) = 660, GOOF = 1.101, final R = 0.0875 and wR = 0.1082 for 7381 observed reflections (I > 2σ(I)). The X-ray analysis reveals that the planes of p-chloroaniline and terephthalaldehyde form a dihedral angle of 87.54(0.28)^o. In the crystal of compound 1, P atoms have tetrahedral geometries, made up by a double-bond O atom, one C_α atom, and two O-ethyl groups. Besides, C_α atoms are responsible for the existence of the optical activity. Five intramolecular hydrogen bonds helping to stabilize the crystal structure are observed. The interaction between compound 1 and DNA/BSA is also studied.