Imidazole Research Articles

Zn(II)-Coordination Polymers Constructed from Isomeric Bis(Imidazole) Derivative Ligands and Tetracarboxylic Acid for the Detection of Iron Ions

AbstractThree Zn(II)-coordination polymers, namely, {[Zn2(µ4-L)(µ-obix)2]·4DMF}n (1), {[Zn2(µ4-L)(µ-mbix)2]·6H2O}n (2) and {[Zn2(µ4-L)(µ-pbix)2]·5H2O}n (3), (L4−: 5,5’-(terephthaloylbis(azanediyl))diisophthalate and obix (y = 2), mbix (y = 3), pbix (y = 4): 1,y-bis((1H-imidazol-1-yl)methyl)benzene) were prepared with a tetracarboxylic acid and flexible isomeric bis(imidazole) linkers and characterized. The compounds displayed structural diversity depending on the rotation of imidazole rings around the –CH2- groups on bis(imidazole) ligands. Compounds 1–3 showed 2-fold interpenetrated 3D framework, 2D structure and 3D framework, respectively. The compounds showed high emissions in solid-state and solutions. Luminescence experiments showed that compounds 1–3 displayed sensitive detection towards Fe3+ ions with detection limits of 2.31 ppm, 5.17 ppm and 2.61 ppm, respectively. Moreover, the compounds could selectively detect Fe3+ ions over the other interfering metal ions via luminescence quenching. The detection mechanism could be ascribed to the competitive light absorption between Fe3+ ions and the compounds.

Thermo-thickening/amphoteric polymer nanocomposite incorporating vinyl-functionalized nano-silica as a viscosifier for high-salt and ultra-high temperature water-based drilling fluids

In the relentless extraction of oil and gas from deeper reservoirs, the harsh geological conditions pose significant rheological challenges for conventional polymer viscosifiers. Hence, the spotlight has turned to the unique potential of thermo-thickening polymers to enhance drilling fluid performance. In this study, a novel polymer nanocomposite (VMS-ATA) was designed to associate thermo-thickening responses, amphoteric characteristics, and vinyl-functionalized nano-silica (VMS) as nanofillers for the formation of a thermally stable polymer nanocomposite-bentonite hybrid system. VMS-ATA was prepared via in-situ polymerization under optimal synthetic conditions, and the unique chemical structure was analyzed using various techniques such as Fourier transform spectroscopy, proton nuclear magnetic resonance, elemental analysis, thermogravimetric analysis, X-ray spectroscopy, transmission electron microscopy, and scanning electron microscopy. The study systematically investigated the enhancement of in-situ covalent bonding characteristics of VMS on the thermo-thickening behavior of VMS-ATA, while comparing it with amine-nano-silica (AMS) incorporated in a polymer composite (AMS-CGBA). TGA analysis revealed that VMS-ATA exhibits excellent thermal stability compared to AMS-CGBA, attributed to the thermally stable VMS (370 °C) compared to AMS (355 °C). Interestingly, VMS-ATA displayed relatively stable and prolonged thermo-thickening responses (100–200 °C) owed to high thermal-induced activation responses above the lower critical solution temperature (LCST) in both salt-free and saturated salt contamination. The rheological results of VMS-ATA viscosity retention at 220 °C and 20 wt% NaCl, exceeded 60 %, which is twice that of AMS-CGBA-containing fluids. As demonstrated, VMS-ATA and AMS-CGBA exhibited similar macro-interactions with rigid imidazole and caprolactam rings, but significantly differed in their micro-interactions owed to in-situ covalent binding induced by VMS compared to hydrogen bonding in AMS. This breakthrough exhibited the potential of VMS nanofillers to effectively maintain thickening response by facilitating efficient heat distribution to minimize rapid viscosity decay and revolutionize the landscape of high-salt and high-temperature (HSHT) drilling applications.

Copper/cobalt metal-organic framework composites for advanced anode material of lithium-ion battery

In this paper, two new types of metal-organic frameworks (MOFs) materials, namely Cu-IM and Co-MOF, have been successfully applied to the anode of lithium-ion batteries with LiPF6 (EC: DMC = 1:1, volume) electrolyte additive. Cu-IM and Co-MOF employed imidazole (IM) and 2-methylimidazole (2-MeIM) as organic ligands, respectively. The results revealed the synthesized MOFs exhibited high initial discharge specific capacities (Cu-IM: 1964.5 mAh g−1, Co-MOF: 1423.3 mAh g−1) as well as low internal resistances (Cu-IM: 146 Ω; Co-MOF: 236 Ω). To alleviate the issue of capacity decay in single MOFs, we attempted the dual-MOFs materials through the rational design of interfacial/surface properties and microstructure. Compared to Cu-IM, the prepared Cu-IM/Co-MOF composites have a higher specific surface area and pore volume. Furthermore, the charge transfer resistance of Cu-IM/Co-MOF composites (141 Ω) was lower than that of Cu-IM and Co-MOF respectively. After a heat treatment to Cu-IM/Co-MOF composites, the electrochemical performance of obtained Cu-IM/Co-MOF 250 dual-MOFs composites have been significantly improved. The Cu-IM/Co-MOF 250 dual-MOFs composites demonstrated excellent cycling stability and high discharge specific capacities at various current densities. The composites displayed stable discharge specific capacity retention of 834 mAh g−1 (50 mA g−1, 75 cycles), 710.5 mAh g−1 (200 mA g−1, 50 cycles), and 392.5 mAh g−1 (500 mA g−1, 50 cycles), highlighting their promising performance for energy storage applications. The synthesized Cu-IM/Co-MOF 250 dual-MOFs composites demonstrates exceptional cycling performance and rate capability, implying that it has the promising prospects as anode material for lithium-ion batteries.

Synthesis and Medicinal Applications of N-Heterocyclic Carbene Complexes based on Caffeine and other Xanthines.

Xanthines are purine derivatives predominantly found in plants. These include compounds such as caffeine, theophylline, and theobromine and exhibit a variety of pharmacological properties, demonstrating efficacy in treating neurodegenerative disorders, respiratory dysfunctions, and also in cancer. The versatile attributes of these materials render them privileged scaffolds for the development of compounds for various biological applications. Xanthines are N-heterocyclic carbene precursors that combine a pyrimidine and an imidazole ring. Owing to their biological relevance, xanthines have been employed as N-heterocyclic carbenes in the development of metallodrugs for anticancer and antimicrobial purposes. In this conceptual review, we examine key examples of N-heterocyclic carbene complexes derived from caffeine and other xanthines, elucidating their synthetic methods and describing their pertinent medicinal applications.

(SC,RS)-Bromido-(N-{4-methyl-1-[(4-methyl-phenyl)sul-fan-yl]-pentan-2-yl}-N'-(pyridin-2-yl)imidazol-2-yl-idene)palladium(II) bromide.

The mol-ecule of the title NCNHCS pincer N-heterocyclic carbene palladium(II) complex, [PdBr(C21H25N3S)]Br, exhibits a slightly distorted square-planar coordination at the palladium(II) atom, with the five-membered chelate ring nearly planar. The six-membered chelate ring adopts an envelope conformation. Upon chelation, the sulfur atom becomes a stereogenic centre with an RS configuration induced by the chiral carbon of the precursor imidazolium salt. There are intra-molecular C-H⋯Br-Pd hydrogen bonds in the structure. The two inter-stitial Br atoms, as the counter-anion of the structure, are both located on crystallographic twofold axes and are connected to the complex cations via C-H⋯·Br hydrogen bonds.

Study on the Antifungal Activity of Gallic Acid and Its Azole Derivatives against Fusarium graminearum.

The wheat scab caused by Fusarium graminearum (F. graminearum) has seriously affected the yield and quality of wheat in China. In this study, gallic acid (GA), a natural polyphenol, was used to synthesize three azole-modified gallic acid derivatives (AGAs1-3). The antifungal activity of GA and its derivatives against F. graminearum was studied through mycelial growth rate experiments and field efficacy experiments. The results of the mycelial growth rate test showed that the EC50 of AGAs-2 was 0.49 mg/mL, and that of AGAs-3 was 0.42 mg/mL. The biological activity of AGAs-3 on F. graminearum is significantly better than that of GA. The results of field efficacy tests showed that AGAs-2 and AGAs-3 significantly reduced the incidence rate and disease index of wheat scab, and the control effect reached 68.86% and 72.11%, respectively. In addition, preliminary investigation was performed on the possible interaction between AGAs-3 and F. graminearum using density functional theory (DFT). These results indicate that compound AGAs-3, because of its characteristic of imidazolium salts, has potential for use as a green and environmentally friendly plant-derived antifungal agent for plant pathogenic fungi.

Surface-active ionic liquids as drug carriers: A physico-chemical study

This work evaluates the potential of two surface active ionic liquids (SAILs) 1-dodecyl-3-methylimidazolium bromide and 1-tetradecyl-3-methylimidazolium bromide as drug carrier for ciprofloxacin (CPF) and compares them with their conventional counterparts dodecyltrimethylammonium bromide and tetradecyltrimethylammonium bromide using spectroscopic and electrochemical techniques. Different physico-chemical parameters including critical micelle concentration (CMC), binding constants, partition coefficients and their corresponding free energy changes, thermodynamic parameters of micellization and redox behavior of micelle-drug systems were investigated. Both the SAILs demonstrated higher solubilization powers and binding constants owing to the less polar nature of imidazolium ring. Lower CMCs indicated relatively stronger hydrophobic forces existing in all SAILs-CPF systems tested. The cyclic voltammetry displayed shifting of oxidation peaks towards higher positive potential in the micellar region indicating the protection of CPF against oxidation. This work demonstrates the benefits of using SAILs as drug carriers due to their lower CMCs, improved binding and partition coefficients, and favorable electrochemical results.

A sulfonated polyimide containing imidazole ring with a low vanadium ion permeable for vanadium redox flow battery

A new type of sulfonated polyimide membrane (6f-abSPI) containing benzimidazole group and trifluoromethyl group (-CF3) is synthesized by one-step copolymerization. The 6f-abSPI-60 membrane with the highest ion selectivity is selected and applied to all vanadium redox flow battery (VRFB). Compared with Nafion 212 (N212) membrane and 6f-SPI-60 membrane, the vanadium ion permeability of 6f-abSPI-60 membrane (1.78 × 10−7 cm2 min−1) is 1/13 lower than that of N212 membrane (2.33 × 10−6 cm2 min−1) and 1/2 lower than 6f-SPI-60 membrane (3.60 × 10−7 cm2 min−1). At the same time, the 6f-abSPI-60 membrane (2.69 × 105 S min cm−3) has significant selectivity, which is 5.6 times higher than N212 membrane (0.48 × 105 S min cm−3). In VRFB tests, the coulombic efficiency (CE) of 6f-abSPI-60 membrane (98.88 %) is significantly higher than that of N212 membrane (92.99 %) and 6f-SPI-60 membrane (97.65 %) at 100 mA cm−2, and the energy efficiency (EE) also reaches a higher value (77.29 %). Additionally, the VRFB equipped with the 6f-abSPI-60 membrane exhibits consistent and reliable performance throughout the 100 cycles of charging and discharging at the current densities of 100 mA cm−2. The good stability of 6f-abSPI membranes is explained by calculating C atoms’ natural bond orbital (NBO) charges on different polyimide (PI) rings.

Ionic liquids adsorption and interfacial tension reduction for synthetic resinous and asphaltenic oils: salinity and pH effects

The effects of sulfate salts under low and high salinity conditions and pH of 3.5–11 on interfacial tension (IFT) reduction and IL adsorption using resinous (RSO) and asphaltenic (8 wt/wt%) synthetic oils are investigated. The measurements showed the increasing effect of pH on the IFT of RSO/DW from 23.5 to 27.3 mN/m (pH = 3.5 → 7) in the first place and a reducing effect (0.4 mN/m) if pH = 7 → 11. Using a high concentration of 50,000 ppm for MgSO4, and Na2SO4 revealed an extensive IFT reduction for a pH value of 11 with the value of 0.20 mN/m for Na2SO4. The measured IFT values showed the significant impact of IL (500 ppm) on the IFT (minimum value of 0.01 mN/m for RSO/50,000 Na2SO4 + 500 ppm 1-decyl-3-methyl imidazolium triflate ([C10mim][TfO])) for pH = 11. The IL adsorption measurements showed the role of in-situ surfactant production (saponification process) on the 1-decyl-3-methyl imidazolium chloride ([C10mim][Cl]) and [C10mim][TfO] adsorption reduction from 3.67 to 2.33 and 4.21 to 3.34 mg IL/g rock, respectively. The performed core flooding experiments using the optimum chemical formulation showed the possibility of tertiary oil recovery with maximum oil recovery of 28.8% based on original oil in place in the presence of 500 ppm.

Engineering pineapple peel cellulose nanofibrils with oxidase-mimic functionalities for antibacterial and fruit preservation

In this study, an antibacterial material (CNF@CoMn-NS) with oxidase-like activity was created using ultrathin cobalt‑manganese nanosheets (CoMn-NS) with a larger specific surface area grown onto pineapple peel cellulose nanofibrils (CNF). The results showed that the CoMn-NS grew well on the CNF, and the obtained CNF@CoMn-NS exhibited good oxidase-like activity. The imidazole salt framework of the CNF@CoMn-NS contained cobalt and manganese in multiple oxidation states, enabling an active redox cycle and generating active oxygen species (ROS) such as singlet molecular oxygen atoms (1O2) and superoxide radical (·O2−), resulting in the significant inactivation of Staphylococcus aureus (74.14%) and Escherichia coli (54.87%). Importantly, the CNF@CoMn-NS did not exhibit cytotoxicity. The CNF@CoMn-NS further self-assembled into a CNF@CoMn-NS paper with flexibility, stability, and antibacterial properties, which can effectively protect the wound of two varieties of pears from decay caused by microorganisms. This study demonstrated the potential of using renewable and degradable CNF as substrate combined with artificial enzymes as a promising approach to creating antibacterial materials for food preservation and even extending to textiles and biomedical applications.

Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl‐protected glucosyl imidazolium iodides as NHC‐precursors and 15 complexes have been synthesized. The structure‐activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki‐Miyaura between bromobenzene and 4‐tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.

Polymerizable deep eutectic solvents: Convenient reactive dispersion media for the preparation of novel multi-walled carbon nanotubes-based functional materials

A new straightforward and green approach for the covalent functionalization of multi-walled carbon nanotubes (MWCNTs) was developed. This carbon nanostructure was efficiently derivatized by polymerizing proper deep eutectic monomers (DEM), a subclass of deep eutectic solvents (DES), based on a series of mono- and bis-vinyl imidazolium salts endowed with different functional groups (–OH, –NH2, –NH3+Br–) in the side chain or in the spacer. Herein, DEM systems played a triple role as convenient dispersion media for MWCNTs, efficient reactive systems, and also as structure-directing agents for the radical-initiated polymerization process onto the surface of MWCNTs. In addition, the new methodology allowed obtaining highly functionalized hybrid materials, as shown by thermogravimetric analyses, in short reaction times (<1h). Transmission electron microscopy (TEM) revealed that the polymeric network orderly develops along the surface of the nanotubes, which act as templating agent for both mono- and bis-vinyl imidazolium salts, despite the random nature of the polymerization process for the latter species. This new functionalization strategy of MWCNTs stands out for its environmentally friendly and time-saving nature leading to the formation of materials with significant potential for applications in a plethora of research fields. As a proof of their possible application, we tested these new hybrid materials as recoverable and recyclable catalysts for the conversion of CO2 into cyclic carbonates under solvent-free conditions, showing good catalytic performances, even in the absence of additional co-catalysts.

Antimicrobial Activity Classification of Imidazolium Derivatives Predicted by Artificial Neural Networks

PurposeThis study assesses the Multilayer Perceptron (MLP) neural network, complemented by other Machine Learning techniques (CART, PCA), in predicting the antimicrobial activity of 140 newly designed imidazolium chlorides against Klebsiella pneumoniae before synthesis. Emphasis is on leveraging molecular properties for predictive analysis.MethodsClassification and regression decision trees (CART) identified the top 200 predictive molecular descriptors. Principal Component Analysis (PCA) reduced these descriptors to 5 components, retaining 99.57% of raw data information. Antimicrobial activity, categorized as high or low, was based on experimentally proven minimal inhibitory concentration (MIC), with a cut-point at MIC = 0.856 mol/L. A 12-fold cross-validation trained the MLP (architecture 5-12-2 with 5 Principal Components).ResultsThe MLP exhibited commendable performance, achieving almost 90% correct classifications across learning, validation, and test sets, outperforming models without PCA dimension reduction. Key metrics, including accuracy (0.907), sensitivity (0.905), specificity (0.909), and precision (0.891), were notably high. These results highlight the MLP model's efficacy with PCA as a high-quality classifier for determining antimicrobial activity.ConclusionsThe study concludes that the MLP neural network, along with CART and PCA, is a robust tool for predicting the antimicrobial activity class of imidazolium chlorides against Klebsiella pneumoniae. CART and PCA, used in this study, allowed input variable reduction without significant information loss. High classification accuracy and associated metrics affirm the method’s potential utility in pre-synthesis assessments, offering valuable insights for antimicrobial compound design.

Ruthenium(II)-Catalyzed Sequential C-H/N-H Alkene Annulation Cascade of Phenanthroimidazoles: Synthesis and Photophysical Studies.

We report ruthenium(II)-catalyzed sequential C-H/N-H alkenylation cascade of phenanthroimidazole and alkenes to form novel phenanthroimidazoisoindol acrylates via dual C-H activation and aza-Michael reaction. The two nitrogen atoms of the imidazole ring act as directing groups for regioselective dual sequential ortho C-H activation. These polycyclic N-heterocycles were evaluated for their photophysical properties.

Dual-Channel Imine-Amine Photoisomerization in a Benzoimidazole and Benzothiazole Coupled System: Photophysics and Applications.

A molecule, namely 2-(1H-benzo[d]imidazol-2-yl)-6-(benzo[d]thiazol-2-yl)-4-bromophenol (BIBTB), having a two-way proton transfer unit of thiazole and imidazole moieties was synthesized and characterized by NMR, electrospray ionization mass spectrometry (ESI-MS), and single-crystal diffraction studies. Steady state and time-resolved spectral studies of BIBTB support excited state intramolecular proton transfer (ESIPT), causing imine-amine tautomerization through a two-way 6-membered H-bonded ring, where the N atoms of benzothiazole and the benzoimidazole unit are involved as proton acceptor sites. Interestingly, in a nonpolar and moderately polar solvent, photoisomerization in BIBTB is found to be favored toward the thiazole ring, whereas in a highly polar solvent, it is favored toward the imidazole ring. A spectral comparison of BIBTB with judicially designed molecules 2-(benzo[d]thiazol-2-yl)-4-bromophenol (HBT) and 2-(1H-benzo[d]imidazol-2-yl)-4-bromophenol (BIB) supports these inferences. Theoretical calculation using the Density Functional Theory (DFT) at CAM-B3LYP/6-311+G(d,p) level supports the existence of two low-energy 6-membered hydrogen-bonded planar conformers in the ground state in the gas phase and in solvents of different dielectrics. The potential energy curves (PECs) calculated along the proton transfer (PT) coordinate are found to have a high energy barrier in the ground state and to be barrierless or have a low energy barrier in the excited state for both the forms. The calculated vertical excitation and the emission energy from the relaxed excited and PT states show good correlation with the experimental spectral data. Aggregation of BIBTB in water with red shifted emission was established from X-ray single-crystal structure analysis, solid state emission, and Dynamic Light Scattering (DLS) measurement. The molecule BIBTB also acts as a fluorescence probe for sensing the explosive picric acid in the subnano scale and can be used to determine the proportion of water in dimethyl sulfoxide (DMSO) solvent.

The Coiling Effect in Ether Ionic Liquids: Exploiting Acetate as a Probe for Transport Properties and Microenvironment Analysis.

The inherently high viscosity of ionic liquids (ILs) can limit their potential applications. One approach to address this drawback is to modify the cation side chain with ether groups. Herein, we assessed the structure-property relationship by focusing on acetate (OAc), a strongly coordinating anion, with 1,3-dialkylimidazolium cations with different side chains, including alkyl, ether, and hydroxyl functionalized, as well as their combinations. We evaluated their viscosity, thermal stabilities, and microstructure using Raman and infrared (IR) spectroscopies, allied to density functional theory (DFT) and ab initio molecular dynamics (AIMD) simulations. The viscosity data showed that the ether insertion significantly enhances the fluidity of the ILs, consistent with the coiling effect of the cation chain. Through a combined experimental and theoretical approach, we analyzed how the OAc anion interacts with ether ILs, revealing a characteristic bidentate coordination, particularly in hydroxyl functionalized ILs due to specific hydrogen bonding with the OH group. IR spectroscopy showed subtle shifts in the acidic hydrogens of imidazolium ring C(2)-H and C(4,5)-H, suggesting weaker interactions between OAc and the imidazolium ring in ether-functionalized ILs. Additionally, spatial distribution functions (SDF) and dihedral angle distribution obtained via AIMD confirmed the intramolecular hydrogen bonding due to the coiling effect of the ether side chain.

Experimental and theoretical investigation of 1-Hexyl-3-methylimidazolium iodide as a corrosion inhibitor for mild steel in HCl environment

This study employed 1-Hexyl-3-methylimidazolium iodide to mitigate the corrosion of Q235 steel in a hydrochloric acid environment. The evaluation of corrosion inhibition effectiveness was comprehensively characterized by combining electrochemical experiments with surface morphology observation. The experimental results demonstrated the capability of the ionic liquid in establishing a film layer on the surface of Q235 steel, which effectively hindered the charge transfer process. Notably, the corrosion inhibition efficiency attained a value of 92.3% at a concentration of 1 mM corrosion inhibitor. Moreover, the process of the corrosion inhibitor adhering to the steel surface aligns with the Langmuir isotherm, demonstrating physicochemical adsorption behavior. The density functional theory (DFT) and molecular dynamics (MD) simulation were utilized for further exploration of the corrosion inhibition mechanism, and the results indicate the ionic liquid can be adsorbed onto the (110) surface of Fe in parallel through N atoms on the imidazole ring.

Formation of hollow spheres structures Co/CoO/ZnO@NC from metal-organic frameworks as a anode for lithium-ion batteries

Transition metal oxides have become a potential anode material for LIBs due to their large theoretical capacity, low cost, abundant resources. However, significant volume changes and severe particle aggregation occur during charge/discharge process. In this work, it is found that the composite of dual component active TMO and single metal, and coating by doped carbon are the effective methods to improve the electrochemical performance and adapt to volume changes in storing lithium. The specific process is based on the co-precipitation of Zn and Co ions in the presence of 2-methylimidazolium salts to produce imidazolium salt frameworks (ZIFs) of bimetallic zeolites, which are then thermally decomposed to form hollow spheres structures Co/CoO/ZnO@NC. The hollow sphere uses Co as the core and CoO/ZnO@NC particles coated with nitrogen doped carbon layer as the shell. These spherical structures exhibit excellent electrochemical performance, high reversible capacity, excellent cycling stability (702 mAh/g at 100 mAg−1 after 100 cycles), and good rate capability (735 mAh/g and 515 mAh/g at 100 mA g−1 and 2000 mA g−1 respectively).

Investigation of the effect of halide counterions on the potential corrosion inhibitor in imidazolium-based ionic liquids

Imidazolium (IMZ)-based ionic liquids (ILs) with various counter ions were investigated as potential corrosion inhibitors. Furthermore, parameters such as bond lengths, bond angles, and dihedral bonds were investigated to demonstrate the adsorption sites of molecules. Moreover, in order to compare the efficiency of the inhibitors, other parameters such as energy gap, hardness, the LUMO, and the HOMO were investigated. The HOMO and LUMO values increased from −4.370 and −0.106 eV to −4.959 and −0.156 eV, respectively, by changing F− to I−. Moreover, the softness of the IMZ base changed from 0.469 to 0.417 eV by increasing the radius of the halide ion. The trend of the band gap value in going from F− to I− changes from 4.264 to 4.797 eV. The total electron density was computed to show the adsorption sites based on the electron density. According to the molecular reactivity results, the inhibitory efficiency of the inhibitors was in the following order: BMI-F > BMI-Cl > BMI-Br > BMI-I. Investigating the IMZ-based ILs with various counterions to evaluate the inhibition profile of molecules provides useful insights into computational protocols for the study of corrosion inhibitors.

Novel Imidazole‐based Hydrazonoyl Cyanides and Amidrazones Containing N(N,O)‐Heterocycles: Selective Synthesis, Reaction Mechanisms and Preliminary Anticancer Evaluation

Two series of novel hybrid heterocyclic compounds that combine the imidazole ring with bioactive piperidine, morpholine or piperazine heterosystems, through a hydrazone unit, were easily obtained by two competitive pathways. Starting from 5‐amino‐4‐cyanoformimidoyl imidazoles and 1‐aminopiperidine, 4‐aminomorpholine or 1‐amino‐4‐methylpiperazine under mild acidic media led to the selective synthesis of 5‐aminoimidazole 4‐carboxamidrazones, whereas the corresponding 4‐hydrazonoyl cyanide derivatives were obtained under stronger acidic conditions. These highly functionalized imidazoles provide convenient synthetic precursors to a vast array of heterocycles with potential pharmaceutical applications. The reaction mechanisms were elucidated on the basis of experimental assays and in silico calculations. The compounds were screened against colorectal cancer HCT116‐p53 wt cell line, and significant IC50 values of 3.69 µM and 4.83 µM were obtained.