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• 693-03-8 n-butyl magnesium bromide 
• 124337-36-6 1-((1H-benzo[d]1,2,3-triazol-1-yl)methyl)-1H-benzo[d]imidazole 
• 51-17-2 benzoimidazole 
• 110-53-2 1-Bromopentane 
• 14273-90-6 methyl 6-bromohexanoate 
• 1426221-93-3 6-(1H-benzimidazol-1-yl)hexanoic acid 
• 1426222-10-7 methyl 6-(1H-benzimidazol-1-yl)hexanoate 
• 1073-32-1 sodium benzimidazolate 
• 14699-83-3 n-pentyl-2,1,3-benzothiadiazolium 2,4-dinitrobenzenesulphonate 
• 64-18-6 formic acid 
• 91215-77-9 N-n-pentyl-o-phenylenediamine 

Relevant academic research and scientific papers

Benzimidazole-based silver(I)-N-heterocyclic carbene complexes as anti-bacterials: Synthesis, crystal structures and nucleic acids interaction studies

A series of new benzimidazolium salts as N-heterocyclic carbene (NHC) precursors has been synthesized. Reactions of these salts with Ag2O with varying metal-to-salt ratio facilitate the formation of a series of new binuclear and mononuclear Ag(I)-NHC complexes. All compounds were characterized using physicochemical and spectroscopic techniques. Single-crystal X-ray diffraction study reveals a binuclear structure for one of the complexes and a mononuclear one for two others. These complexes exist as cationic Ag(I)-NHC complexes with the chelation of carbene carbons to the silver centre in an almost linear manner. The compounds were screened for their anti-bacterial activities against Staphylococcus aureus (ATCC 12600) as a Gram-positive bacterium and Escherichia coli (ATCC 25922) as a Gram-negative bacterium. The results show that both bacteria appear markedly inhibited. Furthermore, the results suggest the possibility of steric variation as a modulation of the anti-bacterial activities. The nuclease activities of the compounds were assessed using gel electrophoresis and the results indicate that these complexes can cleave or degrade DNA and RNA via a non-oxidative mechanism.

Effect of lipophilicity of wingtip groups on the anticancer potential of mono N-heterocyclic carbene silver(I) complexes: Synthesis, crystal structures and in vitro anticancer study

A series of symmetrically n-alkyl-substituted mono benzimidazolium salts with steady increase in n-alkyl chain length have been prepared by stepwise N-alkylation resulting in salts (1–8). The mono N-heterocyclic carbene (NHC)–Ag(I) complexes (9–16) derived from the respective salts were readily accessible by in situ deprotonation using Ag2O. All the salts and the complexes were characterized using Fourier transform infrared, 1H NMR, 13C NMR and elemental analyses. Furthermore, the structures of salts 3 and 7 and complex 16 were elucidated using X-ray crystallography, which established that this mono NHC–Ag(I) complex has a linear bis-carbene arrangement (C2–Ag). The proligands and the respective Ag(I) complexes were studied for their in vitro anticancer potential against human colon cancer cell line (HCT-116) using 5-fluorouracil as a standard. From the IC50 values of all the tested compounds, it can be postulated that there is an influential relationship between the increase in chain length of the wingtip n-alkyl groups and the anticancer potential. The proligands 4–8 and their respective complexes 12–16 with long n-alkyl chain lengths (n?=?6–10) showed better IC50 values (0.3–3.9 μM) than the standard drug with the complexes displaying markedly better antiproliferation activity against HCT-116 cell line than the respective proligands and the standard drug (IC50?=?10.2 μM).

Nitrile functionalized silver(I) N-heterocyclic carbene complexes: DFT calculations and antitumor studies

A series of aliphatic nitrile functionalized benzimidazolium salts and their respective mononuclear N-heterocyclic carbene Ag(I)-NHC complexes are reported. The benzimidazolium salts were synthesized by N-alkylation of 1H-benzimidazole with an appropriate alkyl bromide, followed by reaction with either 5-bromovaleronitrile or 6-bromohexanenitrile. The respective mononuclear Ag(I)-NHC complexes were prepared by the reaction of the benzimidazolium salts with Ag2O. All the synthesized compounds were characterized by physico-chemical and spectroscopic techniques. The molecular structures of the two complexes were elucidated through single-crystal X-ray diffraction analyses. Density functional theory was used to model the structures of the other complexes. The benzimidazolium salts and their complexes were screened for cytotoxicity against a breast cancer cell line (MCF-7), using the MTT assay. All the Ag(I)-NHC complexes gave IC50 values ranging from 7.0?±?1.06 to 12.9?±?1.55?μM which are comparable to the standard drug, tamoxifen (IC50?=?11.2?±?1.84?μM), while all of the benzimidazolium salts proved to be inactive.

Synthesis, characterization and anti-proliferative activity of propylene linked bis-benzimidazolium salts and their respective dinuclear Silver(I)-N-heterocyclic carbene complexes

A new series of propylene linked bis-benzimidazolium salts, 1–4 were reacted with Ag2O to facilitate the formation of their respective dinuclear Ag(I)-N-heterocyclic carbene (NHC) complexes, 5–8 respectively. All compounds were fully characterized by elemental analyses, 1H NMR, 13C NMR and FTIR spectroscopy techniques. The molecular structures of compounds 1 and 6 were elucidated through single crystal X-ray diffraction analyses. Both salts and complexes were tested for anti-cancer potential against breast cancer (MCF-7) cell line. The IC50 values are in the range of 7?±?1–18?±?3?μM show that the complexes 5–8 possess moderate antiproliferative effect while their respective salts 1–4 are found to be inactive against MCF-7?cell line.

Properties of alkylbenzimidazoles for CO2 and SO2 capture and comparisons to ionic liquids

To date, few reports have been concerned with the physical properties of the liquid phases of imidazoles and benzimidazolespotential starting materials for a great number of ionic liquids. Prior research has indicated that alkylimidazole solvents exhibit different, and potentially advantageous physical properties, when compared to corresponding imidazolium-based ionic liquids. Given that even the most fundamental physical properties of alkylimidazole solvents have only recently been reported, there is still a lack of data for other relevant imidazole derivatives, including benzimidazoles. In this work, we have synthesized a series of eight 1-n-alkylbenzimidazoles, with chain lengths ranging from ethyl to dodecyl, all of which exist as neat liquids at ambient temperature. Their densities and viscosities have been determined as functions of both temperature and molecular weight. Alkylbenzimidazoles have been found to exhibit viscosities that are more similar to imidazolium-based ILs than alkylimidazoles, owed to a large contribution to viscosity from the presence of a fused ring system. Solubilities of CO2 and SO2, two species of concern in the emission of coal-fired power generation, were determined for selected alkylbenzimidazoles to understand what effects a fused ring system might have on gas solubility. For both gases, alkylbenzimidazoles were determined to experience physical, non-chemically reactive, interactions. The solubility of CO2 in alkylbenzimidazoles is 10%-30% less than observed for corresponding ILs and alkylimidazoles. 1-butylbenzimidazole was found to readily absorb at least 0.333 gram SO2 per gram at low pressure and ambient temperature, which could be readily desorbed under an N2 flush, a behavior more similar to imidazolium-based ILs than alkylimidazoles. Thus, we find that as solvents for gas separations, benzimidazoles share characteristics with both ILs and alkylimidazoles. Science China Press and Springer-Verlag Berlin Heidelberg 2012.

Synthesis, crystal structure, in vitro anticancer and in vivo acute oral toxicity studies of tetramethylene linked bis-benzimidazolium salts and their respective dinuclear Ag(I)–NHC complexes

The proligands of the series tetramethylenebis(N-n-alkylbenzimidazolium bromide) (where n?=?3–10) (1–8) as N-heterocyclic carbene (NHC) precursors have been prepared by reacting the initially synthesized N-n-alkyl benzimidazole with 1,4-dibromobutane in 2?:?1 M ratio. A reaction of Ag2O with 1–8 resulted in the formation of Ag(I) complexes tetramethylenebis{(N-n-alkylylbenzimidazol-2-ylidene)silver(I)hexafluorophosphate} (9–16), respectively. All the synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR, atomic absorption and elemental analysis. Single-crystal X-ray diffraction study on tetramethylenebis{(N-n-octylbenzimidazol-2-ylidene)silver(I)hexafluorophosphate} (14) has revealed that the complex exists as a dinuclear compound. All compounds were assessed for their antiproliferation test on human colorectal cancer cell line (HCT 116). Interestingly, increasing the n-alkyl chain length from n?=?3 to 10 of the proligands and their respective complexes showed trends in increased cytotoxicity against human colon cancer cell line. Cytotoxicity data showed that tetramethylene linked bis-benzimidazolium salts and their respective dinuclear Ag(I)–NHC complexes can be useful therapeutic agents against colon cancer.

Synthesis and characterization of ortho-xylyl linked bis-benzimidazolium salts (Part-II)

A number of N-alkylbenzimidazoles were synthesized by reactions of benzimidazole with alkyl halides (PentBr, HexBr, OctBr, DecBr). The subsequent treatment of the resulting N-alkylbenzimidazoles with 1,2-bis(bromomethylene) benzene afforded corresponding bisbenzimidazolium salts. All the compounds were characterized by spectroscopic techniques (NMR and FT-IR) and microanalysis. Molecular structures of selected compounds were established through single crystal X-ray diffraction studies.

Synthesis, structural investigation and antibacterial studies of non–symmetrically p–nitrobenzyl substituted benzimidazole N–heterocyclic carbene–silver(I) complexes

Several new non–symmetrically p–nitrobenzyl substituted benzimidazole–based mono–N–heterocyclic carbene (NHC)–silver(I) acetate (7a–e) and bis–NHC–silver(I) hexafluorophosphate complexes (8a–e) were synthesized by combination of 1–ethyl/1–propyl/1–butyl/1–pentyl/1–hexyl–3–(4–nitrobenzyl)benzimidazolium hexafluorophosphate salts (6a–e) with silver(I) acetate and silver(I) oxide in methanol and acetonitrile, respectively, in good yields. All the benzimidazolium hexafluorophosphate salts (6a–e) and their corresponding NHC–silver(I) complexes (7a–e and 8a–e) were structurally characterized by 1H, 13C NMR, ATR–IR spectrometry and elemental analysis. The solid–state structures of bis–NHC–silver(I) hexafluorophosphate complexes (8c) and (8e) were determined by single crystal X–ray diffraction method. Preliminary in vitro antibacterial potential of all the compounds (6a–e, 7a–e and 8a–e) were studied against six standard bacterial strains; two Gram–positive (Staphylococcus aureus and Bacillus subtilis) and four Gram–negative bacterial species (Escherichia coli, Pseudomonas aeruginosa, Shigella sonnei, and Salmonella typhi) by Kirby–Bauer's disc diffusion method and their Minimum Inhibitory Concentration (MIC) was determined by broth macrodilution method. All the NHC–silver(I) complexes (7a–e and 8a–e) exhibited moderate to high antibacterial activities with MIC ranging between 16.0 and 128.0?μg/mL, whereas benzimidazolium hexafluorophosphate salts (6a–e) demonstrated poor antibacterial potentials.

A new type of triptycene-based stationary phases with alkylated benzimidazolium cations for gas chromatographic separations

Favorable physicochemical properties and unique molecular recognition capability endow triptycene-based materials with good potential as stationary phases for gas chromatography (GC). This work reports a new type of triptycene-based materials functionalized by three benzimidazolium cations with different peripheral alkyl lengths (denoted as TP-3Bim-5C and TP-3Bim-12C) and their GC separation performance. As a result, they shared high resolving performance for the naphthalene isomers but differed for the benzene derivatives with varying polarity. Moreover, their capillary columns exhibited good repeatability and thermal stability. This work presents a facile strategy for tailoring the selectivity of the TP-based stationary phases and demonstrates their promising future for chromatographic analysis.

Synthesis, Characterization, Crystal Structures, and Catalytic C-C Coupling and Hydrosilylation Reactions of Palladium(II) Complexes Derived from CNC Pincer-Type N-Heterocyclic Carbenes

A series of pyridine linker containing bis(benz)imidazolium salts serving as precursors to CNC pincer-type N-heterocyclic carbene (NHC) ligands were prepared by successive N-alkylation of the azole core. Binuclear NHC complexes of silver(I) were synthesized by in situ deprotonation of the corresponding (benz)imidazolium salt with silver(I) oxide in acetonitrile at elevated temperature in the dark. Subsequently, pincer-type palladium(II)-NHC complexes were prepared by transmetalation using silver(I)-NHC complexes in acetonitrile at elevated temperatures. All compounds were fully characterized by elemental analysis, FTIR spectroscopy, and 1H and 13C NMR spectroscopy. X-ray diffraction studies on single crystals of three compounds confirmed the distorted square-planar geometry around the palladium(II) center. All complexes are monomeric in nature, and the bis-NHC ligand chelates in the CNC mode. The effective catalytic potentials of the palladium complexes were demonstrated by their high activities in aqueous-phase Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions of phenylboronic acid and n-butyl acrylate with a range of functionalized bromobenzene derivatives. The former coupling reaction afforded biphenyls in yields of 71-99%, whereas the latter reaction evidenced low yields of the n-butyl cinnamates. Further, all the palladium complexes were studied for their potential in a catalytic hydrosilylation reaction.