Synthesis, characterization and biological activities of organotin(IV) diallyldithiocarbamate complexes

Adeyemi, Jerry O.; Onwudiwe, Damian C.; Ekennia, Anthony C.; Anokwuru, Chinedu P.; Nundkumar, Nirasha; Singh, Moganavelli; Hosten, Eric C.

doi:10.1016/j.ica.2018.09.085

Cited by 38 publications

(23 citation statements)

References 60 publications

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“…A comparison of theoretical and experimental 13 C NMR spectral data (Table ), has shown an upfield shift in C=O signal ascribed to decrease in electron density at carbon upon coordination through carbonyl oxygen to the tin atom. The methyl and n ‐butyl carbons attached to tin in (I) appeared at 12.83 ppm and in (II) at 13.72, 25.53, 27.65 ppm …”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Choudhary

Bhatt

Dash

et al. 2020

Applied Organom Chemis

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The new diorganotin (IV) complexes of composition [Me2SnCl(3,5‐(NO2)2C6H2(OH)CONHO)] (I) and [n‐Bu2SnCl(3,5‐(NO2)2C6H2(OH)CONHO)] (II) have been synthesized by the reactions of Me2SnCl2 and n‐Bu2SnCl2 with potassium 3,5‐dinitrosalicylhydroxamate [3,5‐(NO2)2C6H2(OH)CONHOK]‐ a ligand of biological significance bearing –NO2 and –OH substituents presumed to yield complexes with efficient bioactivity. The complexes have been characterized by elemental analyses, IR, 1H, 13C and 119Sn NMR and mass spectrometry in order to study the ligational behavior and probale geometry around tin as the ligand might show different bonding modes and geometry in complexes. The geometries of (I) and (II) have been computed using B3LYP/6–31 + G(d,p) set by DFT method and the vibrational frequencies, 1H and 13C NMR spectra compared with the experimental data. A comparison of computed bond lengths (C=O, C‐N, and N‐O) of (I) and (II) with that of free ligand, the Sn‐O bond lengths, bond angles coupled with 119Sn NMR and IR spectral data have suggested coordination through carbonyl and hydroxamic oxygens (O, O coordination) displaying five‐coordinate distorted trigonal‐bipyramidal geometry around tin. The thermal behavior of (I) and (II) has been studied by thermogravimetric techniques (TGA, DTG, DTA) and various kinetic parameters have been calculated. The electrochemical behavior of ligand, (I) and (II) studied by cyclic voltammetric technique has shown ligand centered redection. The HOMO‐LUMO energies and orbitals, global reactivity descriptors, various thermodynamic parameters and dipole moment (μ) have been computed to determin the molecular properties of complexes. The in vitro antimicrobial activity assay against bacteria and fungi by MIC method has indicated higher potency of (I) than (II). The in vitro cytotoxicity on human muscle rhabdomyosarcoma (RD) by MTT method and the antioxidant potential by DPPH free radical scavenging showed higher inhibitory effect of complexes than ligand.

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Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Choudhary

Bhatt

Dash

et al. 2020

Applied Organom Chemis

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“…In the past few years, there has been a resurgence of interest in the anti-cancer activity of organotin dithiocarbamates (Khan et al, 2015;Mohamad, Awang, Kamaludin et al, 2016) and very recently, a report on the in vitro cytotoxicity trial of several tin diallyldithiocarbamate compounds was described as well as a preliminary assessment of anti-microbial activity (Adeyemi et al, 2019); some phosphane-gold(I) and phosphane-silver(I) dithiocarbamates are known to be bactericidal based on pharmacokinetic studies (Sim et al, 2014;. The aforementioned report on tin diallyldithiocarbamate compounds (Adeyemi et al, 2019) also presented the first crystal-structure determinations for tin compounds of diallyldithiocarbamate.…”

Section: Chemical Contextmentioning

confidence: 99%

(N,N-Diallyldithiocarbamato-κ² S,S′)triphenyltin(IV) and bis(N,N-diallyldithiocarbamato-κ² S,S′)diphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Haezam¹,

Awang²,

Kamaludin³

et al. 2020

Acta Cryst E

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The crystal and molecular structures of the title organotin dithiocarbamate compounds, [Sn(C6H5)3(C7H10NS2)] (I) and [Sn(C6H5)2(C7H10NS2)2] (II), present very distinct tin atom coordination geometries. In (I), the dithiocarbamate ligand is asymmetrically coordinating with the resulting C3S2 donor set defining a coordination geometry intermediate between square-pyramidal and trigonal–bipyramidal. In (II), two independent molecules comprise the asymmetric unit, which differ in the conformations of the allyl substituents and in the relative orientations of the tin-bound phenyl rings. The dithiocarbamate ligands in (II) coordinate in an asymmetric mode but the Sn—S bonds are more symmetric than observed in (I). The resulting C2S4 donor set approximates an octahedral coordination geometry with a cis-disposition of the ipso-carbon atoms and with the more tightly bound sulfur atoms approximately trans. The only directional intermolecular contacts in the crystals of (I) and (II) are of the type phenyl-C—H...π(phenyl) and vinylidene-C—H...π(phenyl), respectively, with each leading to a supramolecular chain propagating along the a-axis direction. The calculated Hirshfeld surfaces emphasize the importance of H...H contacts in the crystal of (I), i.e. contributing 62.2% to the overall surface. The only other two significant contacts also involve hydrogen, i.e. C...H/H...C (28.4%) and S...H/H...S (8.6%). Similar observations pertain to the individual molecules of (II), which are clearly distinguishable in their surface contacts, with H...H being clearly dominant (59.9 and 64.9%, respectively) along with C...H/H...C (24.3 and 20.1%) and S...H/H...S (14.4 and 13.6%) contacts. The calculations of energies of interaction suggest dispersive forces make a significant contribution to the stabilization of the crystals. The exception is for the C—H...π contacts in (II) where, in addition to the dispersive contribution, significant contributions are made by the electrostatic forces.

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“…It is now well established that tin (IV) is capable of forming various coordination numbers due to the electron‐acceptor (Lewis acidity) of the tin center. The design and development of new structures of organotin (IV) compounds has been attributed to the Lewis acidity nature of tin (IV) center which can coordinate to a variety of O‐, N‐, Cl‐, or S‐donor ligands . Tin atom can exist as tetra‐, penta‐, hexa‐ and hepta‐coordinated or form fluxional stereochemical complexes, however, the penta‐ and hexa‐coordinated organotin (IV) adducts are more common among them.…”

Section: Introductionmentioning

confidence: 99%

Exploiting the versatility of pyridyl ligands for the preparation of diorganotin (IV) adducts: spectral, crystallographic and Hirshfeld surface analysis studies

Momeni

Fathi

Abbasi

et al. 2019

Applied Organom Chemis

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Diorganotin (IV) complexes SnR 2 X 2 (R = Me, Ph; X = Cl, NCS) form a series of versatile complexes when react with bidentate substituted pyridyl ligands. The reaction of dimethyltin dichloride with 5,5′-dimethyl-2,2′-bipyridine (5,5′-Me 2 bpy) resulted in the formation of [SnMe 2 Cl 2 (5,5′-Me 2 bpy)] (1). Moreover, the reaction of SnMe 2 (NSC) 2 with 4,4′-di-tert-butyl-2,2′-bipyridine (bu 2 bpy), 1,10-phenanthroline (phen) and 4,7-diphenyl-1,10-phenanthroline (bphen) affords the hexa-coordinated complexes [SnMe 2 (NCS) 2 (bu 2 bpy)] (2), [SnMe 2 (NCS) 2 (phen)] (3) and [SnMe 2 (NCS) 2 (bphen)] (4), respectively. The resulting complexes have been characterized using elemental analysis, IR, multinuclear NMR ( 1 H, 13 C, 119 Sn) and DEPT-135°NMR spectroscopy. On the other hand, the reaction of diphenyltin dichloride with 2,2′-biquinoline (biq) and 4,7-phenantroline (4,7-phen) led to the formation of polymeric complexes of [SnPh 2 Cl 2 (4,7-phen)] n (5) and [SnPh 2 Cl 2 (biq)] n (6). The NMR spectra, however, reveal the ligand lability in solution and suggest a coordination number of 5. The X-ray crystal structures of complexes [SnMe 2 Cl 2 (5,5′-Me 2 bpy)] (1), [SnMe 2 (NCS) 2 (bu 2 bpy)] (2) and [SnMe 2 (NCS) 2 (bphen)] (4) have been determined which reveal that the geometry around the tin atom is distorted octahedral with trans-[SnMe 2 ] configuration. Interestingly, the crystal structure of (H 2 biq) 2 [SnPh 2 Cl 4 ]•2CHCl 3 (7) was characterized by X-ray crystallography from a chloroform solution of [SnPh 2 Cl 2 (biq)] n (6) indicating the formation of doubly protonated [H 2 biq] + and [Ph 2 SnCl 4 ] 2− which are stabilized by a network of hydrogen bonds with a feature of trans-[SnPh 2 ]. The 3D Hirshfeld surface analysis and 2D fingerprint maps were used for quantitative mapping out of the intermolecular interactions for 1, 2, 4 and 7 which show the presence of π-π and hydrogen bonding interactions which are associated between donor and acceptor atoms (N, S, Cl) in the solid state.

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Synthesis, characterization and biological activities of organotin(IV) diallyldithiocarbamate complexes

Cited by 38 publications

References 60 publications

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

(N,N-Diallyldithiocarbamato-κ² S,S′)triphenyltin(IV) and bis(N,N-diallyldithiocarbamato-κ² S,S′)diphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Exploiting the versatility of pyridyl ligands for the preparation of diorganotin (IV) adducts: spectral, crystallographic and Hirshfeld surface analysis studies

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Synthesis, characterization and biological activities of organotin(IV) diallyldithiocarbamate complexes

Cited by 38 publications

References 60 publications

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

Synthesis, characterization, thermal, computational and biological activity studies of new potential bioactive diorganotin (IV) nitrosubstitutedhydroxamates‐A comparative study

(N,N-Diallyldithiocarbamato-κ2 S,S′)triphenyltin(IV) and bis(N,N-diallyldithiocarbamato-κ2 S,S′)diphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study

Exploiting the versatility of pyridyl ligands for the preparation of diorganotin (IV) adducts: spectral, crystallographic and Hirshfeld surface analysis studies

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Product

Resources

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(N,N-Diallyldithiocarbamato-κ² S,S′)triphenyltin(IV) and bis(N,N-diallyldithiocarbamato-κ² S,S′)diphenyltin(IV): crystal structure, Hirshfeld surface analysis and computational study