Synthesis, Structural Characterization, and Biological Application of p-[N,N-bis(2-chloroethyl) Aminobenzaldehyde Thiosemicarbazone and Its Nickel (II) Complex

Abstract

New complex of Ni(II) with p-[N,N-bis(2-chloroethyl)]aminobenzaldehyde thiosemicarbazone (CEABTSC) have been synthesized and characterized by elemental analysis, IR, electronic, and 1 H NMR spectroscopy. The crystal structure of the free ligand has been determined by single-crystal X-ray diffraction technique. The compound crystallizes in the Triclinic crystal system with space group P-1, Z D 2, Calculated density D 1.392 mg/m 3 , V D 761.64 (18) A 3 with unit cell parameters a D 8.2847(11) A , a D 99.074 , b D 8.7432(12) A , b D 94.035(7) , c D 11.2423(15) A , g D 107.337 (6) ; final R 1 and wR 2 are 0.0796 and 0.3021, respectively. The crystal structure reveals that the compound exists in the thione form and C12 and C11 are at E configuration to each other with respect to N2-N3 bond. The packing of the molecules in the crystal lattice is stabilized by intramolecular N(3)-H(3). . .S(1) and N(4)-H(4D). . . S(1) hydrogen bonds resulting in the formation of edge fused R 2 2 (8) ring motif. In the complex, thiosemicarbazone ligand is coordinated to nickel through (1:2 complex) SNNS mode. The complex has been tested for their antibacterial activity against various pathogenic bacteria.

Synthesis, characterization, antifungal and antibacterial activities evaluation of copper (II), zinc (II) and cadmium (II) chloride and bromide complexes with new (E)‐1‐(3,4‐dimethoxybenzylidene)‐4‐methylthiosemicarbazone ligand

“…Thiosemicarbazones exist in two tautomeric forms, thione and thiol. The thione functions as bidentate neutral ligand and the thiol can deprotonate and act as an anionic ligand [ 19 ] owing to the presence of C=N. Thiosemicarbazones exist as E and Z stereoisomers.…”

“…The E isomer predominates in the mixture considering the thermodynamic stability. [ 19 ] The crystal structure revealed that the MTSVT ( L ) exists in the thione form and C3 and C2 are at E configuration to each other concerning the N1–N2 bond. The thione form in the solid state was confirmed by the observed bond lengths C2–S1 [1.6899(17) Å] and C2–N2 [1,348(2) Å].…”

“…The proposed assignments are based on previous results [ 17,34 ] and pertinent references. [ 15,19 ]…”

“…Owing to the effectiveness of these compounds against human pathogens, they may be considered as effective antiseptic agents to disinfect areas prone to contamination by microorganisms, such as doctors’ offices and hospital settings. [ 19 ]…”

“…A research study on Schiff bases of N (4)‐thiosemicarbazones showed that the biological performance of this class of ligands depends on the nature of the carbonyl compound, [ 17 ] the presence of an alkyl group at the terminal N4 nitrogen atom and the existence of functionality as a further binding site. [ 18 ] In addition, the substituted benzaldehydes display considerable differences in stereo‐electronic properties [ 19 ] and biological activities compared with the unsubstituted benzaldehydes. [ 20 ] The metal complexes resulting from thiosemicarbazone‐substituted benzaldehyde displayed important biological activity as they can act as xanthine oxidase inhibitors.…”