Syntheses, crystal structure, spectroscopic characterization and antifungal activity of new N-R-sulfonyldithiocarbimate metal complexes

Abstract

Five new compounds with the general formula of (Bu(4)N)(2)[M(RSO(2)NCS(2))(2)], where Bu(4)N=tetrabutylammonium cation, (M=Ni, R=4-FC(6)H(4)) (1), (M=Zn, R=4-FC(6)H(4), 4-ClC(6)H(4), 4-BrC(6)H(4), 4-IC(6)H(4)), (2), (3), (4) and (5), respectively, were obtained by the reaction of the appropriate potassium N-R-sulfonyldithiocarbimate (RSO(2)N=CS(2)K(2)) with nickel(II) chloride hexahydrate or zinc(II) acetate dihydrate in metanol:water 1:1. The elemental analyses and the IR data are consistent with the formation of the expected bis(dithiocarbimato)metal(II) complexes. The (1)H and (13)C NMR spectra showed the signals for the tetrabutylammonium cation and the dithiocarbimate moieties. The compounds 1, 2 and 5 were also characterized by X-ray diffraction techniques. The nickel(II) is coordinated by two N-4-fluorophenylsulphonyldithiocarbimato(2-) ligands forming a planar coordination. The zinc(II) exhibits distorted tetrahedral configuration in compounds 2 and 5 due to the chelation effect of two sulfur atoms of the N-R-sulfonyldithiocarbimate ligands. The antifungal activities of the compounds were tested in vitro against Colletotrichum gloeosporioides, an important fungus that causes the plant disease known as anthracnose in fruit trees. All the complexes were active.

Synthesis, X-ray crystal structures and properties of complex salts and sterically crowded heteroleptic complexes of group 10 metal ions with aromatic sulfonyl dithiocarbimates and triphenylphosphine ligand

“…The M-S, M-P, C-S and C@N bond lengths in 1, 2, 4a and 5 are well in agreement with the previously reported dimensions for the related dithio complexes [22][23][24][25][26][27][28]. …”

“…Thus aromatic sulfonyl dithiocarbimates can be used as important scaffolds for the synthesis of complex salts and heteroleptic complexes. Despite this synthetic versatility [22,23] and the fact that various important properties have been established for the metal complexes that can be formed, scant attention has been paid to this ligand system and only recently the coordination chemistry and some of their applications have been exploited [24][25][26][27][28].…”

Crystal Structures and Antifungal Activities of Fluorine-Containing Thioureido Complexes with Nickel(II)

“…The crystal structures of the three ligands (HL2, HL3, HL6) and the corresponding complexes were determined by X-ray diffraction. In consideration of the knwon good biological effects of nickel ion and its complexes [30,31], we were interested in exploring the effect of fluorine substitution and the coordination with Ni (II) on the antifungal activities.…”

Syntheses, crystal structures and properties of sterically congested heteroleptic complexes of group 10 metal ions with p-tolylsulfonyl dithiocarbimate and 1,2-bis (diphenylphosphino) ethane

“…Complexes of the ligand aromaticsulfonyl dithiocarbimate and their possible applications have however been exploited recently [20][21][22]. This ligand has two important features (i) it may exhibit greater electron delocalization through C-S, C-N and N-SO 2 -Ar bonds and (ii) upon S, S coordination to a metal center it forms a more strained four-membered chelate ring in comparison with the five-membered ring formed with the mnt 2− complexes which in turn can influence intra and inter ligand S⋯S and M⋯S dimensions.…”

“…In the IR spectra all the three complexes display absorptions near 1435, 1216-1292, 1120 and 900 cm −1 characteristic of υ(C=N), υ asym (SO 2 ), υ sym (SO 2 ) and υ asym (CS 2 ) vibrations respectively indicating S, S coordination of the ligand dithiocarbimate with increasing importance of the canonical form I (Scheme S1 in the ESI) [20][21][22].…”