Effect of functionalization of N-bound organic moiety in zinc(II) dithiocarbamate complexes on structure, biological properties and morphology of zinc sulfide nanoparticles

doi:10.1016/J.POLY.2017.03.010

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Effect of functionalization of N-bound organic moiety in zinc(II) dithiocarbamate complexes on structure, biological properties and morphology of zinc sulfide nanoparticles

Journal Article•DOI•

Effect of functionalization of N-bound organic moiety in zinc(II) dithiocarbamate complexes on structure, biological properties and morphology of zinc sulfide nanoparticles

Ethiraj Sathiyaraj¹, Sundaramoorthy Tamilvanan², Subbiah Thirumaran², Samuele Ciattini•Institutions (2)

Kalasalingam University¹, Annamalai University²

28 May 2017-Polyhedron (Pergamon)-Vol. 128, pp 133-144

TL;DR: In this paper, a single crystal X-ray crystallography was used to determine the structure of ZnS5, which is a coordination polyhedron that is intermediate between tetragonal pyramid and trigonal bipyramid.

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About: This article is published in Polyhedron.The article was published on 2017-05-28. It has received 10 citations till now. The article focuses on the topics: Coordination geometry & Zinc.

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Journal Article•DOI•

Exploring the Topological Landscape Exhibited by Binary Zinc-triad 1,1-dithiolates

[...]

Edward R. T. Tiekink

14 Jul 2018

TL;DR: The crystal chemistry of the zinc-triad binary 1, 1,1-dithiolates, that is, compounds of xanthate [−S2COR], dithiophosphate [ −S2P(OR)2], and dithIocarbamate [−CNR2] ligands, is reviewed in this article.

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Abstract: The crystal chemistry of the zinc-triad binary 1,1-dithiolates, that is, compounds of xanthate [−S2COR], dithiophosphate [−S2P(OR)2], and dithiocarbamate [−S2CNR2] ligands, is reviewed. Owing to a wide range of coordination modes that can be adopted by 1,1-dithiolate anions, such as monodentate, chelating, μ2-bridging, μ3-bridging, etc., there exists a rich diversity in supramolecular assemblies for these compounds, including examples of zero-, one-, and two-dimensional architectures. While there are similarities in structural motifs across the series of 1,1-dithiolate ligands, specific architectures are sometimes found, depending on the metal centre and/or on the 1,1-dithiolate ligand. Further, an influence of steric bulk upon supramolecular aggregation is apparent. Thus, bulky R groups generally preclude the close approach of molecules in order to reduce steric hindrance and therefore, lead to lower dimensional aggregation patterns. The ligating ability of the 1,1-dithiolate ligands also proves crucial in determining the extent of supramolecular aggregation, in particular for dithiocarbamate species where the relatively greater chelating ability of this ligand reduces the Lewis acidity of the zinc-triad element, which thereby reduces its ability to significantly expand its coordination number. Often, the functionalisation of the organic substituents in the 1,1-dithiolate ligands, for example, by incorporating pyridyl groups, can lead to different supramolecular association patterns. Herein, the diverse assemblies of supramolecular architectures are classified and compared. In all, 27 structurally distinct motifs have been identified.

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40 citations

Additional excerpts

...81 Et/n-Bu S4 + 1 O dimer [100] 82 Et/Cy S4 + 1 O dimer [25] 83 3 Et/Ph S4 + 1 O dimer [101] 84 5 Et/Ph S4 + 1 O dimer [102] 85 Et/CH2CH2OH S4 + 1 O dimer [83] 86 n-Pr/i-Pr S4 + 1 O dimer [103] 87 10 i-Pr/CH2CH2OH S4 + 1 O dimer [96] 88 c-Pr/CH2C6H4-4-OMe S4 + 1 O dimer [104] 89 n-Bu/Ph S4 + 1 O dimer [105] 90 Benzyl/(CH2)13Me S4 + 1 O dimer [106] 91 9 Benzyl/R2 9 S4 + 1 O dimer [74] 92 CH2(2-furyl)/CH2C6H4-4-Cl S4 + 1 O dimer [75] 93 CH2(2-furyl)/R(2) 9 S4 + 1 O dimer [74] 94 CH2C6H4-4-OMe/(CH2)2N(CH2CH2)2O S4 + 1 O dimer [74] 95 i-Bu/i-Bu S4 M monomer [107] S4 + 1 O 96 R + R’ = (CH2)4NMe NS4 P polymer [108] 97 11 Benzyl/CH2(3-py) NS4 Q dimer [72] 98 CH2(ferrocenyl)/CH2(3-py) NS4 Q dimer [109] 99 12 Et/CH2(4-py) NS4 P polymer [110] 100 13 CH2(ferrocenyl)/CH2(4-py) N2S4 R layer [109] 1 R1 is 2,3-dihydro-1,4-benzodioxin-6-yl)CH2; 2 C2/c polymorph; 3 P21/c polymorph; 4 Pbcn polymorph; 5 P ̄1 polymorph; 6 tetra-acetonitrile solvate; 7 di-hydrate; 8 methanol solvate; 9 R2 is 1,3-benzodioxol-5-CH2; 10 hydrate; 11 ethanol solvate; 12 di-4-methylpyridine solvate; 13 dimethylformamide solvate....
[...]
...36 CH2CH2OMe/CH2CH2OMe S4 M monomer [64] 37 Cy/Cy S4 M monomer [25] 38 Benzyl/Benzyl S4 M monomer [65] 39 Me/Cy S4 M monomer [66] 40 n-Pr/CH(Me)Et S4 M monomer [67] 41 NRR’ = 3,4-dihydroquinoline S4 M monomer [68] 42 n-Bu/5-t-Bu-3-Me-2-OH-benzyl S4 M monomer [69] 43 CH2CH2OH/CH2(ferrocenyl) S4 M monomer [70] 44 (CH2)3OEt/3,5-di-t-Bu-4-OH-benzyl S4 M monomer [71] 45 Benzyl/CH2(1-Me-pyrrol-2-yl) S4 M monomer [72] 46 Benzyl/4-OMe-benzyl S4 M monomer [73] 47 Benzyl/R1 1 S4 M monomer [74] 48 CH2(4-OMe-phenyl)/CH2(2-furyl) S4 M monomer [75] 49 Me/Me S4 + 1 N dimer [76] 50 2 n-Bu/n-Bu S4 + 1 N dimer [77] 51 3 n-Bu/n-Bu S4 + 1 N dimer [78] 52 Me/CH2(ferrocenyl) S4 + 1 N dimer [74] 53 Et/Et S4 + 1 O dimer [79] 54 n-Pr/n-Pr S4 + 1 O dimer [80] 55 i-Pr/i-Pr S4 + 1 O dimer [81] 56 CH2C(H)=CH2/CH2C(H)=CH2 S4 + 1 O dimer [82] 57 4 CH2CH2OH/CH2CH2OH S4 + 1 O dimer [83] 58 2 CH2CH2OH/CH2CH2OH S4 + 1 O dimer [84] 59 5 CH2CH2OH/CH2CH2OH S4 + 1 O dimer [85] 60 R + R’ = (CH2)4 S4 + 1 O dimer [86] 61 R + R’ = (CH2)5 S4 + 1 O dimer [87] 62 R + R’ = (CH2)6 S4 + 1 O dimer [88] 63 R + R’ = (CH2)5-4-Me S4 + 1 O dimer [89] 64 R + R’ = (CH2)5-4-C(=O)OEt S4 + 1 O dimer [72] 65 6 R + R’ = (CH2)5-4-C(=O)ON[C(=O)CH2]2 S4 + 1 O dimer [90] 66 R + R’ = (CH2CH2)2NEt S4 + 1 O dimer [91] 67 R + R’ = (CH2CH2)2NPh S4 + 1 O dimer [92] 68 R + R’ = (CH2CH2)2NC6H4-3-OMe S4 + 1 O dimer [93] 69 R + R’ = (CH2CH2)2NC6H4-4-OMe S4 + 1 O dimer [93] 70 Me/Et S4 + 1 O dimer [94] 71 Me/n-Pr S4 + 1 O dimer [94] 72 Me/i-Pr S4 + 1 O dimer [94] 73 Me/n-Bu S4 + 1 O dimer [94] 74 Me/Ph S4 + 1 O dimer [95] 75 7 Me/CH2CH2OH S4 + 1 O dimer [96] 76 8 Me/CH2CH2OH S4 + 1 O dimer [83] 77 Me/CH2C(=O)OMe S4 + 1 O dimer [97] 78 Me/CH2C(H)(OMe)2 S4 + 1 O dimer [98] 79 9 Me/R2 9 S4 + 1 O dimer [74] 80 Et/i-Pr S4 + 1 O dimer [99]...
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Journal Article•DOI•

Synthesis, characterization and anticancer studies of bis-(N-methyl-1-phenyldithiocarbamato) Cu(II), Zn(II), and Pt(II) complexes: single crystal X-ray structure of the copper complex

[...]

Fartisincha P. Andrew¹, Peter A. Ajibade¹•Institutions (1)

University of KwaZulu-Natal¹

08 Nov 2018-Journal of Coordination Chemistry

TL;DR: In this paper, N-methyl-1-phenyldithiocarbamate complexes were synthesized and characterized by FTIR, NMR, UV-visible spectroscopy and elemental analysis.

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Abstract: Cu(II), Pt(II), and Zn(II) complexes of N-methyl-1-phenyldithiocarbamate were synthesized and characterized by FTIR, NMR, UV-visible spectroscopy and elemental analysis. The complexes were ...

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24 citations

Journal Article•DOI•

Insights into the Antimicrobial Potential of Dithiocarbamate Anions and Metal-Based Species

[...]

Chien Ing Yeo, Edward R. T. Tiekink, Jactty Chew

14 Jun 2021

TL;DR: This bibliographic review of the literature points to the exciting potential of dithiocarbamate-based therapeutics in the crucial battle against bacteria.

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Abstract: Bacterial infection remains a worldwide problem that requires urgent addressing. Overuse and poor disposal of antibacterial agents abet the emergence of bacterial resistance mechanisms. There is a clear need for new approaches for the development of antibacterial therapeutics. Herein, the antibacterial potential of molecules based on dithiocarbamate anions, of general formula R(R’)NCS2(−), and metal salts of transition metals and main group elements, is summarized. Preclinical studies show a broad range of antibacterial potential, and these investigations are supported by appraisals of possible biological targets and mechanisms of action to guide chemical syntheses. This bibliographic review of the literature points to the exciting potential of dithiocarbamate-based therapeutics in the crucial battle against bacteria. Additionally, included in this overview, for the sake of completeness, is mention of the far fewer studies on the antifungal potential of dithiocarbamates and even less work conducted on antiparasitic behavior.

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14 citations

Journal Article•DOI•

Structural variations in zinc(II) complexes with N,N-di(4-fluorobenzyl)dithiocarbamate and imines: New precursor for zinc sulfide nanoparticles

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Pandurangan Selvaganapathi¹, Subbiah Thirumaran¹, Samuele Ciattini•Institutions (1)

Annamalai University¹

15 Jul 2018-Polyhedron

TL;DR: In this paper, Zinc sulfide nanoparticles were prepared and characterized by elemental analysis, spectroscopy (IR, 1H and 13C NMR) and their structures were elucidated by X-ray crystallography.

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12 citations

Journal Article•DOI•

Functionalized zinc(II) dithiocarbamate complexes: Synthesis, spectral and molecular structures of bis(N-cyclopropyl-N-4-methoxybenzyldithiocarbamato-S,S′)zinc(II) and (2,2′-bipyridine)bis(N-cyclopropyl-N-4-methoxybenzyldithiocarbamato-S,S′)zinc(II)

[...]

Ethiraj Sathiyaraj¹, Marimuthu Venkatesh Perumal, Erumaippatty Rajagounder Nagarajan¹, Chennan Ramalingan¹•Institutions (1)

Kalasalingam University¹

01 Sep 2017-Journal of Saudi Chemical Society

TL;DR: In this paper, two new zinc and dithiocarbamate integrated metal complexes such as bis(N-cyclopropyl-N-4methoxybenzyldithIocarbamato-S,S′)zinc(II) (1 ) and (2,2′-bipyridine) have been synthesized and their spectral investigations have been accomplished.

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7 citations

References

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Journal Article•DOI•

Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays

[...]

Tim R. Mosmann

16 Dec 1983-Journal of Immunological Methods

TL;DR: A tetrazolium salt has been used to develop a quantitative colorimetric assay for mammalian cell survival and proliferation and is used to measure proliferative lymphokines, mitogen stimulations and complement-mediated lysis.

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50,114 citations

Journal Article•DOI•

Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen–sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane]copper(II) perchlorate

[...]

Anthony W. Addison, T. Nageswara Rao, Jan Reedijk, Jacobus Van Rijn, G. C. Verschoor - Show less +1 more

01 Jan 1984-Journal of The Chemical Society-dalton Transactions

TL;DR: In this article, the linear quadridentate N2S2 donor ligand 1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane (bmdhp) forms mono-and di-hydrate 1 : 1 copper(II) complexes which are significantly more stable toward autoreduction than those of the non-methylated analogue.

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Abstract: The linear quadridentate N2S2 donor ligand 1,7-bis(N-methylbenzimidazol-2′-yl)-2,6-dithiaheptane (bmdhp) forms mono- and di-hydrate 1 : 1 copper(II) complexes which are significantly more stable toward autoreduction than those of the non-methylated analogue. The deep green monohydrate of the perchlorate salt crystallises as the mononuclear aqua-complex, [Cu(bmdhp)(OH2)][ClO4]2, in the monoclinic space group P21/n, with Z= 4, a= 18.459(3), b= 10.362(2), c= 16.365(3)A, and β= 117.14(1)°. The structure was solved and refined by standard Patterson, Fourier, and least-squares techniques to R= 0.047 and R′= 0.075 for 3 343 independent reflections with l > 2σ(l). The compound consists of [Cu(bmdhp)(OH2)]2+ ions and ClO4– counter ions. The co-ordination around copper is intermediate between trigonal bipyramidal and square pyramidal, with Cu–N distances of 1.950(4) and 1.997(4)A, Cu–O(water) 2.225(4)A, and Cu–S 2.328(1) and 2.337(1)A. In the solid state, the perchlorate dihydrate's co-ordination sphere may be a topoisomer of the monohydrate's. A new angular structural parameter, τ, is defined and proposed as an index of trigonality, as a general descriptor of five-co-ordinate centric molecules. By this criterion, the irregular co-ordination geometry of [Cu(bmdhp)(OH2)]2+ in the solid state is described as being 48% along the pathway of distortion from square pyramidal toward trigonal bipyramidal. In the electronic spectrum of the complex, assignment is made of the S(thioether)→ Cu charge-transfer bands by comparison with those of the colourless complex Zn(bmdhp)(OH)(ClO4). E.s.r. and ligand-field spectra show that the copper(II) compounds adopt a tetragonal structure in donor solvents.

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7,886 citations

Journal Article•DOI•

Hirshfeld surface analysis

[...]

Mark A. Spackman¹, Dylan Jayatilaka¹•Institutions (1)

University of Western Australia¹

07 Jan 2009-CrystEngComm

TL;DR: In the last few years, the analysis of molecular crystal structures using tools based on Hirshfeld surfaces has rapidly gained in popularity as mentioned in this paper, which represents an attempt to venture beyond the current paradigm of nuclear distances and angles, crystal packing diagrams with molecules represented via various models, and to view molecules as organic wholes.

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Abstract: In the last few years the analysis of molecular crystal structures using tools based on Hirshfeld surfaces has rapidly gained in popularity. This approach represents an attempt to venture beyond the current paradigm—internuclear distances and angles, crystal packing diagrams with molecules represented via various models, and the identification of close contacts deemed to be important—and to view molecules as “organic wholes”, thereby fundamentally altering the discussion of intermolecular interactions through an unbiased identification of all close contacts.

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4,930 citations

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Small-particle research: physicochemical properties of extremely small colloidal metal and semiconductor particles

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Arnim Henglein

01 Dec 1989-Chemical Reviews

2,741 citations

Book Chapter•DOI•

Electronic Molecular Structure, Reactivity and Intermolecular Forces: An Euristic Interpretation by Means of Electrostatic Molecular Potentials

[...]

Eolo Scrocco, Jacopo Tomasi

01 Jan 1978-Advances in Quantum Chemistry

TL;DR: In this paper, a model that relies on the knowledge of the molecular electrostatic potential, which is derived from a molecular wave function by using the usual methods for calculating the mean expectation value of an operator, is discussed.

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Abstract: Publisher Summary This chapter discusses a model that relies on the knowledge of the molecular electrostatic potential, which is derived from a molecular wavefunction by using the usual methods for calculating the mean expectation value of an operator. In its basic premises the model employs quantum mechanics, with only the approximations necessary in molecular quantal calculations. The model is also discussed regarding its relationships with the Hellmann–Feynman theorem. The electrostatic potential V itself is examined in order to show how the electrostatic potential reflects the characteristics of the electronic distribution of a molecule and then the reliability of V is discussed as a reactivity index. The shape of the electrostatic potential and its relationship to the electronic molecular structure is discussed with the aid of various examples. One of them includes the glycine tautomers and the corresponding anion example. The chapter also discusses the electrostatic molecular potential in terms of local group contributions.

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1,116 citations