Another silver complex of 1,3-dibenzylimidazol-2-ylidene: Solution and solid-state structures

Berding, Joris; Kooijman, Huub; Spek, Anthony L.; Bouwman, Elisabeth

doi:10.1016/j.jorganchem.2009.02.030

Cited by 18 publications

(18 citation statements)

References 26 publications

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“…Triethylsilane and 3-hexyne were degassed and stored under argon on activated molecular sieves. N-Isopropylimidazole, [20] N-phenylimidazole, [46] N-isopropylbenzimidazole, [20] N-phenylbenzimidazole, [47] 1a, [48] 1b, [49] 1f, [23] 2e, [24] 3c, [19] 3d, [19] 4a, [18] and 4f [21] were synthesized according to literature procedures. 1 H and 13 C NMR spectra were recorded on a Bruker DPX300.…”

Section: Methodsmentioning

confidence: 99%

“…The silver(I) complex was prepared in situ from ligand precursor 1f and Ag 2 O in dichloromethane. [23] The 1 H NMR spectra of all nickel complexes lacked the characteristic imidazolium NCHN resonance at around 10 ppm, indicating successful carbene generation. The other peaks present in the NMR spectra of the starting imidazolium salts could successfully be identified, albeit shifted slightly from their original position.…”

Section: Synthesis Of Nickel(ii) Complexes Bearing Two Monodentate Nhmentioning

confidence: 97%

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[NiX₂(NHC)₂] Complexes in the Hydrosilylation of Internal Alkynes

et al. 2011

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A number of nickel(II) dihalide complexes with small monodentate N-heterocyclic carbene ligands was synthesized and tested for their catalytic activity in the hydrosilylation of internal alkynes. The nickel(0) active species was obtained from the starting nickel(II) complex by reduction with diethylzinc. In all cases the catalytic reaction yielded the syn product selectively. The fastest catalysts reached full conversion

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of Nickel(ii) Complexes Bearing Two Monodentate Nhmentioning

confidence: 97%

[NiX₂(NHC)₂] Complexes in the Hydrosilylation of Internal Alkynes

et al. 2011

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“…1,3-Dibenzyl-1H-imidazol-3-ium bromide (1a), 3-(4-cyanobenzyl)-1-methyl-1H-imidazol-3-ium bromide (1b), and 3-(4-cyanobenzyl)-1-methyl-1H-benzimidazol-3-ium bromide (1c) were synthesized according to literature [28] [30], whereas the synthesis of bromo(1,3-dibenzyl-2,3-dihydro-1H-imidazol-2-yl)silver (2a) was carried out according to our new procedure instead of the procedure reported in [45].…”

Section: Experimental Partmentioning

confidence: 99%

Novel Benzyl‐ or 4‐Cyanobenzyl‐Substituted N‐Heterocyclic (Bromo)(carbene)silver(I) and (Carbene)(chloro)gold(I) Complexes: Synthesis and Preliminary Cytotoxicity Studies

Patil

Deally

Hackenberg

et al. 2011

Helvetica Chimica Acta

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N-Heterocyclic carbene (NHC) complexes bromo(1,3-dibenzyl-1,3-dihydro-2H-imidazol-2-ylidene)silver(I) (2a), bromo[1-(4-cyanobenzyl)-3-methyl-1,3-dihydro-2H-imidazol-2-ylidene]silver(I) (2b), and bromo[1-(4-cyanobenzyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-ylidene]silver(I) (2c) were prepared by the reaction of 1,3-dibenzyl-1H-imidazol-3-ium bromide (1a), 3-(4-cyanobenzyl)-1-methyl-1H-imidazol-3-ium bromide (1b), and 3-(4-cyanobenzyl)-1-methyl-1H-benzimidazol-3-ium bromide (1c), respectively, with silver(I) oxide. NHC Complexes chloro(1,3-dibenzyl-1,3-dihydro-2H-imidazol-2-ylidene)gold(I) (3a), chloro[1-(4-cyanobenzyl)-3-methyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(I) (3b), and chloro[1-(4-cyanobenzyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-ylidene]gold(I) (3c) were prepared via transmetallation of corresponding (bromo)(NHC)silver(I) complexes with chloro(dimethylsulfido)gold(I). The complex 3a was characterized in two polymorphic forms by single-crystal X-ray diffraction showing two rotamers in the solid state. The cytotoxicities of all three bromo(NHC)silver(I) complexes and three (chloro)(NHC)gold(I) complexes were investigated through 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bormide (MTT)-based preliminary in vitro testing on the Caki-1 cell line in order to determine their IC 50 values. (Bromo)(NHC)silver(I) complexes 2a -2c and (chloro)(NHC)gold(I) complexes 3a -3c were found to have IC 50 values of 27 AE 2, 28 AE 2, 34 AE 6, 10 AE 1, 12 AE 5, and 12 AE 3 mm, respectively, on the Caki-1 cell line.

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“…We did not follow the synthetic procedure of 1,3-dibenzylimidazolium bromide (6a), and 1,3-dibenzylbenzimidazolium bromide (6c), published in literature [10][11][12] instead we synthesised according to our new and milder procedure. On the other hand, the synthesis of 1,3-dibenzyl-4,5-dichloroimidazolium bromide (6b) was carried out according to a published literature procedure.…”

Section: Synthesesmentioning

confidence: 99%

“…[10][11][12] 1,3-Bis(4-methoxybenzyl)imidazolium Bromide (3a): 1H-Imidazole (0.79 g, 11.68 mmol) and K 2 CO 3 (2.42 g, 17.52 mmol) were stirred for 15 min in 60 mL of dry acetonitrile. p-Methoxybenzyl bromide (3.40 mL, 23.36 mmol) was added in one portion and stirring was continued at room temperature for further 2 d. After the solvent was removed under reduced pressure 140 mL of water were added.…”

Section: Synthesesmentioning

confidence: 99%

Synthesis, Cytotoxicity and Antibacterial Studies of p‐Methoxybenzyl‐Substituted and Benzyl‐Substituted N‐Heterocyclic Carbene–Silver Complexes

et al. 2010

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p‐Methoxybenzyl‐substituted and benzyl‐substituted N‐heterocyclic carbene (NHC) [(3a–c) and (6a–c)] precursors were synthesised from the reaction of 1H‐imidazole (1a), 4,5‐dichloro‐1H‐imidazole (1b), and 1H‐benzimidazole (1c) with p‐methoxybenzyl bromide (2) and benzyl bromide (5). These NHC precursors were then treated with silver(I) acetate to yield the NHC–silver complexes [1,3‐bis(4‐methoxybenzyl)imidazol‐2‐ylidene]silver(I) acetate (4a), [4,5‐dichloro‐1,3‐bis(4‐methoxybenzyl)imidazol‐2‐ylidene]silver(I) acetate (4b), [1,3‐bis(4‐methoxybenzyl)benzimidazol‐2‐ylidene]silver(I) acetate (4c), (1,3‐dibenzylimidazol‐2‐ylidene)silver(I) acetate (7a), (1,3‐dibenzyl‐4,5‐dichloroimidazol‐2‐ylidene)silver(I) acetate (7b), and (1,3‐dibenzylbenzimidazol‐2‐ylidene)silver(I) acetate (7c), respectively. The NHC precursor 3c, four NHC–silver complexes 4c and 7a–c were characterised by single‐crystal X‐ray diffraction method. The preliminary antibacterial activity of all the compounds was studied against Gram‐negative bacteria Escherichia coli, and Gram‐positive bacteria Staphylococcus aureus using the Kirby–Bauer disk‐diffusion method. Almost all the NHC–silver complexes have shown high antibacterial activity compared to the NHC precursors. In addition, the NHC–silver complexes had their cytotoxicity investigated through MTT‐based preliminary in vitro testing on the Caki‐1 cell lines in order to determine their IC50 values. NHC–silver complexes 4a–c and 7a–c were found to have IC50 values of 7.3 (+/–6), 12.7(+/–3), 25.2 (+/–5), 2.5 (+/–3), 10.8 (+/–4) and 12.5 (+/–4) μM respectively on the Caki‐1 cell line.

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Another silver complex of 1,3-dibenzylimidazol-2-ylidene: Solution and solid-state structures

Cited by 18 publications

References 26 publications

[NiX₂(NHC)₂] Complexes in the Hydrosilylation of Internal Alkynes

[NiX₂(NHC)₂] Complexes in the Hydrosilylation of Internal Alkynes

Novel Benzyl‐ or 4‐Cyanobenzyl‐Substituted N‐Heterocyclic (Bromo)(carbene)silver(I) and (Carbene)(chloro)gold(I) Complexes: Synthesis and Preliminary Cytotoxicity Studies

Synthesis, Cytotoxicity and Antibacterial Studies of p‐Methoxybenzyl‐Substituted and Benzyl‐Substituted N‐Heterocyclic Carbene–Silver Complexes

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Another silver complex of 1,3-dibenzylimidazol-2-ylidene: Solution and solid-state structures

Cited by 18 publications

References 26 publications

[NiX2(NHC)2] Complexes in the Hydrosilylation of Internal Alkynes

[NiX2(NHC)2] Complexes in the Hydrosilylation of Internal Alkynes

Novel Benzyl‐ or 4‐Cyanobenzyl‐Substituted N‐Heterocyclic (Bromo)(carbene)silver(I) and (Carbene)(chloro)gold(I) Complexes: Synthesis and Preliminary Cytotoxicity Studies

Synthesis, Cytotoxicity and Antibacterial Studies of p‐Methoxybenzyl‐Substituted and Benzyl‐Substituted N‐Heterocyclic Carbene–Silver Complexes

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[NiX₂(NHC)₂] Complexes in the Hydrosilylation of Internal Alkynes

[NiX₂(NHC)₂] Complexes in the Hydrosilylation of Internal Alkynes