Recent advances in the coordination and supramolecular chemistry of monopodal and bipodal acylthiourea-based ligands

Nkabyo, Henry A.; Barnard, Ilse; Koch, Klaus; Luckay, Robert C.

doi:10.1016/j.ccr.2020.213588

Cited by 34 publications

(23 citation statements)

References 138 publications

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“…The structural determination indicates mononuclear square planar complexes with cis configuration, in which divalent metal ions are coordinated by two deprotonated ligands {L 1 } − or {L 2 } − through two ( S , O )‐chelates. Such bidentate cis ‐L( S , O ) coordination which is more thermodynamically favorable than trans ‐L( S , O ) fashion, has been observed in majority of reported benzoylthiourea complexes with divalent metal ions [8c,13] . The M−O and M−S bond lengths (M=Ni 2+ , Cu 2+ ) are in the same ranges as those found in the analogous complexes with other benzoylthiourea ligands [7b,c,h,14] .…”

Section: Resultssupporting

confidence: 54%

“…The complexes are mononuclear with Co(III) ions octahedrally coordinated by three deprotonated ( S , O )‐bidentate ligands {L 1 } − or {L 2 } − with a facial arrangement of donor atoms. Hitherto, this type of arrangement is the unique coordination geometry known for homoleptic tris ‐complexes of benzoylthioureas and trivalent metal ions [13] . The Co−O and Co−S bond lengths are in the range of 1.915(2)–1.936(4) Å and 2.2034(9)–2.2120(2) Å, respectively.…”

Section: Resultsmentioning

confidence: 90%

“…The resonance of protons in the aliphatic double bond in HL 2 appears as two doublets at 7.68 ppm and 6.68 ppm with the typical trans vicinal spin coupling constant of 15.5 Hz. The 13 1 show resonances in the range of 120-150 ppm, while those of HL 2 appear in the region between the two signals assignable to carbon atoms of the aliphatic double bond at 144.0 ppm and 127.7 ppm.…”

Section: Resultsmentioning

confidence: 99%

“…Hitherto, this type of arrangement is the unique coordination geometry known for homoleptic tris-complexes of benzoylthioureas and trivalent metal ions. [13] The CoÀ O and CoÀ S bond lengths are in the range of 1.915( 2)-1.936( 4) Å and 2.2034( 9)-2.2120(2) Å, respectively. This is in good agreement with the values observed in the Co(III) tris-complexes with other benzoylthioureato ligands.…”

Section: The Tris-complexes [Co(l) 3 ] (L = L 1 L 2 )mentioning

confidence: 98%

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Syntheses, Structures, and Bioactivity Evaluation of some Transition Metal Complexes with Aroylbis(N,N‐diethylthioureas) Derived from Natural Compounds

Pham

Nguyễn³

et al. 2021

Zeitschrift anorg allge chemie

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Two novel benzoylthioureas derived from gallic acid, (tri-Oacetyl)galloyl-N,N-diethylthiourea HL 1 , and cinnamic acid, cinnamoyl-N,N-diethylthiourea HL 2 have been successfully prepared and characterized by means of elemental analysis, IR, NMR, high-resolution MS, and X-ray crystallography. The organic ligands react with Ni(AcO) 2 and Cu(AcO) 2 in MeOH under formation of bis-complexes with the compositions of [M(L) 2 ] (M=Ni 2 + , Cu 2 + ; L=L 1 , L 2 ). Similar reactions with Co(AcO) 2 , however, result in Co(III) tris-complexes [Co(L) 3 ] (L=L 1 , L 2 ) with the metal ions oxidized presumably by atmospheric dioxygen. X-ray crystallography and spectroscopic characterization reveal a cis square-planar coordination in the bis-complexes and facial octahedral geometry in the tris-complexes. In all of metal complexes, the deprotonated organic compounds ({L 1 } À and {L 2 } À ) serve as (S,O)-bidentate ligands. The ligand HL 1 and its Ni(II) and Cu(II) complexes exhibit weak antiproliferative effects on the human MCF7 breast and HepG2 liver cancer cells with IC 50 values in the range of 60-115 μM. Surprisingly, the triscomplex [Co(L 1 ) 3 ] exhibits high cytotoxicity with IC 50 values of 22.23 � 1.58 μM for MCF7 and 28.30 � 3.09 μM for HepG2 cancer cells. The activity against MCF7 cells is even more than that of cisplatin under the same conditions.

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Section: Resultssupporting

confidence: 54%

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: The Tris-complexes [Co(l) 3 ] (L = L 1 L 2 )mentioning

confidence: 98%

See 2 more Smart Citations

Syntheses, Structures, and Bioactivity Evaluation of some Transition Metal Complexes with Aroylbis(N,N‐diethylthioureas) Derived from Natural Compounds

Pham

Nguyễn³

et al. 2021

Zeitschrift anorg allge chemie

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“…Among these, the Nbenzoyl thiourea derivatives are versatile ligands that coordinate to form stable compounds. These derivatives possess very strong donor groups (Carbonyl and thioamide) that allow the preparation of different transition metal complexes, either monoanionic bidentate form by deprotonation that forms neutral homoleptic or heteroleptic complexes with S,O coordination or in neutral form only through the S atom [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21]. Several benzoyl thiourea derivatives and their metal complexes are also associated with various types of biological activities such as insecticidal, herbicidal, antibacterial, antifungal, anti-tubercular, antithyroid, anthelmintic, rodenticidal, and plant growth regulator properties [22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide

2021

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N-(2-Chlorophenylcarbamothioyl)cyclohexanecarboxamide was characterized by a single crystal X-ray diffraction study. Crystal data for this compound, C14H17ClN2OS; Monoclinic, space group P21/n with Z = 4, a = 5.2385(10) Å, b = 17.902(4) Å, c = 15.021(3) Å, β = 90.86(3)°, V = 1408.5(5) Å3, T = 153(2) K, μ(MoKα) = 0.413 mm-1, Dcalc = 1.400 g/cm3, 9840 reflections measured (7.082° ≤ 2Θ ≤ 50.378°), 2519 unique (Rint = 0.0406, Rsigma = 0.0335) which were used in all calculations. The final R1 was 0.0397 (I > 2σ(I)) and wR2 was 0.0887 (all data). The puckering parameters (q2 = 0.019(3) Å, q3 = 0.578(3) Å, θ = 1.0(3)° and φ = 51(8)°) of the title compound show that the cyclohexane ring adopts a chair conformation. The molecular conformation of the title compound is stabilized by intramolecular hydrogen bonds (N2-H2⋅⋅⋅Cl1, N2-H2⋅⋅⋅O1, and C2-H2A⋅⋅⋅S1) and intermolecular hydrogen bonds (N1-H1⋅⋅⋅S1i and C9-HA⋅⋅⋅S1ii: 2-x, 2-y, 1-z). The intramolecular hydrogen bonds (N2-H2⋅⋅⋅O1 and C2-H2A⋅⋅⋅S1) are also form two pseudo-six-membered rings. Density functional theory optimized structure in the gaseous phase at B3LYP/6-311G(d,p) level of theory has been compared with the experimentally defined molecular structure. The molecular orbitals HOMO and LUMO with the energy gap for the title compound are calculated and the estimated energy gap (ΔE) between the HOMO and LUMO energies levels of the title compound is 3.5399 eV, which implies that the title molecule is very reactive. The Hirshfeld surface analysis reveals that the most important contributions to crystal packing are from H···H (49.0%), H···C/C···H (12.5%), H···Cl/Cl···H (10.9%), and H···S/S···H (10.0%) interactions. The energy-framework calculations are used to analyze and visualize the three-dimensional topology of the crystal packing. The intermolecular energy analysis confirmed a significant contribution of dispersion to the stabilization of molecular packings in the title compound.

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Synthesis, spectral characteristics and molecular structure of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives

Pokotylo

Zadorozhnii

Kiselev

et al. 2023

Journal of Heterocyclic Chem

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In this work, we report the synthesis of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives based on acylated thioureas. The method for the preparation of 1,3,5‐oxadiazine derivatives is based on the reaction of dehydrosulfurization of the starting acylated thioureas under the action of dicyclohexylcarbodiimide (DCC) followed by the [4 + 2] cycloaddition reaction of another DCC molecule to the resulting intermediate carbodiimide. The structure of the obtained derivatives of 1,3,5‐oxadiazine was confirmed by 1H, 13C NMR, IR spectroscopy, mass spectrometry, and x‐ray diffraction analysis.

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Recent advances in the coordination and supramolecular chemistry of monopodal and bipodal acylthiourea-based ligands

Cited by 34 publications

References 138 publications

Syntheses, Structures, and Bioactivity Evaluation of some Transition Metal Complexes with Aroylbis(N,N‐diethylthioureas) Derived from Natural Compounds

Syntheses, Structures, and Bioactivity Evaluation of some Transition Metal Complexes with Aroylbis(N,N‐diethylthioureas) Derived from Natural Compounds

Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide

Synthesis, spectral characteristics and molecular structure of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives

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