Oxidation reactions, coordination chemistry and antibacterial activities with ligand 2-{(diphenylphosphino)methyl}-N,N-dimethylaniline

N,N-dimethyl-o-toluidine was treated with n-butyllithium-tmeda in diethylether/hexane solution to give (2-(dimethylamino)benzyl)lithium which reacts with chlorodiphenylphosphine to form the corresponding hemilabile N,P-ligand 2- PPh2CH2-1-NMe2C6H4 (1). Oxidation of 1 with elemental sulfur or gray selenium gave the corresponding sulfide and selenide 2-(E)PPh2CH2-1-NMe2C6H4 (E = S (2), Se (3)), respectively. The reaction of 1 with M(CO)(6) (M = Mo, W) afforded cis-[Mo(CO)(4){2-PPh2CH2-1-NMe2C6H4}(2)](4) and trans-[W(CO)(4){2-PPh2CH2-1-NMe2C6H4}(2)](5), respectively. The treatment of 1 with copper(I) iodide in 1:1 mol ratio produced [CuI{2-PPh2CH2-1-NMe2C6H4}](2) (6). The complexes 4-6 have been screened for antibacterial activity and the results were compared with the activity of the free ligand 1 against four bacterial strains. Complexes 4 and 6 had the highest antibacterial activity and can be considered as promising antimicrobial agents. Compounds 1-6 were characterized by multinuclear NMR spectroscopy (H-1, C-13, P-31, Se-77 NMR), IR and elemental analysis. Crystal structure determinations of 1, 2, 4, and 6 were carried out. (C) 2019 Published by Elsevier B.V.