Synthesis, Crystal Structure and Antibacterial Activity of N,N′-Bis(4-methoxy-benzylidene)-1,4-bis(3-aminopropyl)piperazine

Abstract

A new Schiff base, N,N′-bis(4-methoxy-benzylidene)-1,4-bis(3-aminopropyl)piperazine (BMBA), has been synthesized by the reaction of 1,4-bis(3-aminopropyl)piperazine and 4-methoxy-benzaldehyde in methanol solution. The title compound was characterized by elemental analysis, IR spectrum, 1H NMR, 13C NMR and X-ray single crystal diffraction analyses. The compound crystallizes in the monoclinic system with space group C2/c and a = 24.071(5), b = 9.4035(19), c = 11.263(2) A, β = 96.787(2)°, V = 2531.6(9) A3, D c = 1.193 g/cm3, M r = 454.60, Z = 4, F (000) = 984, μ = 0.079 mm−1, R 1 = 0.0693, and ωR 2 = 0.2269. In the crystal structure, molecules of BMBA and water of crystallization are linked through intermolecular O2W–H2′···N2 hydrogen bond, forming a 1D hydrogen bonding network that generates planar “ribbons” running parallel to the c-axis. Furthermore, the antibacterial activity of title compound was investigated preliminary by agar diffusion method, and it exhibited certain inhibited effect against Escherichia coli, Staphylococcus aureus and Bacillus subtilis. A new Schiff base, N,N′-bis(4-methoxy-benzylidene)-1,4-bis(3-aminopropyl)piperazine, has been synthesized by the reaction of 1,4-bis(3-aminopropyl)piperazine and 4-methoxy-benzaldehyde in methanol solution, and characterized by elemental analysis, IR spectrum, 1H NMR, 13C NMR and X-ray single crystal diffraction analyses. Furthermore, the antibacterial activity was investigated by agar diffusion method, and the results indicated that the Schiff base was active relatively against Escherichia coli, Staphylococcus aureus and Bacillus subtilis.