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Polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6: Synthesis, crystal structures, and catalytic activity

  • Aiyi Xin , Tingting Yang , Fang Peng and Zhiguo Wang EMAIL logo
Published/Copyright: October 11, 2023
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Open Chemistry
From the journal Open Chemistry Volume 21 Issue 1

Abstract

One-pot synthesis of polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6 Compound 1 was carried out by the reaction of methylimidazole, 1,2-dibromoethane, and Ag2O in tetrahydrofuran at 60°C for 2 h. Compound 1 was characterized by elemental analysis, 1 H nuclear magnetic resonance, and single crystal X-ray diffraction. The crystal cell parameters of Compound 1 are as follows: a = 8.916(4) Å, b = 17.655(9) Å, c = 9.024(4) Å, α = 90°, β = 103.621(7)°, γ = 90°, V = 1380.6(12) Å3, and Z = 4. The silver atoms in Compound 1 are pentacoordinated with three bromine atoms, one silver atom, and one nitrogen atom of methyl imidazole, and polymeric methyl imidazole silver bromide was formed based on this structure. The catalytic effects under optimized conditions were investigated in this study, and the results showed that Compound 1 possesses a strong catalytic effect on the oxidation of 2-methylnaphthalene with a conversion rate of 77.15% by using hydrogen peroxide as the oxidant at 80°C for 3 h. The catalytic mechanism was explored simultaneously.

Keywords: polymerized silver bromide; imidazole; C–H bonds; 2-methylnaphthalene

1 Introduction

Ag(I) complexes are of great interest due to their important structure and extensive applications as transfer reagents [1,2,3], drug intermediates [4], and potential catalysts [5,6]. The structures of complexes vary among ligands, solvents, and reaction conditions. Coordinating anions, especially in complexes with halide anions, have led to diverse bonding motifs in the solid-state [7,8]. The properties of Ag(I) complexes change greatly with different coordination environments, which affects the application of these complexes for practical use [9,10]. Hitherto, various organic transformations catalyzed by Ag(I) complexes have been achieved, including diboration reactions with various terminal and internal alkenes [11], ring-opening polymerization of lactide [12], coupling of unactivated aldehydes [13], formation of propargylamines by coupling reactions [14], coupling between N-tosylhydrazone and phenylacetylene [15], Heck couplings of heteroaryl halides [16], and enantioselective and diastereoselective construction of complex heterocyclic molecules [17].

Among the processes listed above, C–H bond functionalization processes, which have been supposed to be the most effective synthetic strategies for the assembly of complex molecules, have been particularly studied. However, the activation of C–H bonds has been an enormous challenge because of their high bond dissociation energies and low carbon–hydrogen bond polarity. Some studies have demonstrated that Ag(I) complexes have high catalytic activity in C–H bond functionalization processes. Yang et al. reported an effective strategy that employs well-defined vinyl-N-triftosylhydrazones as a versatile alkylating reagent to enable direct assembly of C–H bonds from low-cost alkane feed stocks [18]. Pérez and his team found that it is possible to exert regioselection in the silver-catalyzed functionalization of linear alkanes from diazo compounds [19]. These findings provide new and more selective catalytic systems for the challenging functionalization of C–H bonds in a selective manner.

β-Menadione is widely used in medicine, pesticides, and additive fields as an important chemical raw material, and it is generally obtained by oxidation of 2-methylnaphthalene [20,21]. The oxidation methods of 2-methylnaphthalene are generally divided into three categories according to the type of oxidant. Chromium trioxide is used as an oxidant in most industrial synthesis processes [22,23,24]. However, this method only has a target product yield of 40–50% with poor selectivity and causes severe environmental pollution accompanied by the generation of a large amount of chromium-containing water [25]. To solve this problem, researchers mixed trivalent and tetravalent cerium salts in a ratio of 1:2 as oxidants to obtain β-menadione, but the regeneration of salts needs to be electrolyzed, which requires enormous energy consumption [26]. The air oxidation method combines air and organic matter through the gas or liquid phase and achieves catalytic oxidation in the presence of a catalyst. However, the reaction requires a high temperature, and the yield of the target product is generally low [27]. As a green oxidant, hydrogen peroxide has received extensive attention and is often used to oxidize 2-methylnaphthalene. It has been reported that 60% hydrogen peroxide (H2O2) was used as the oxidant in an acetic acid system with palladium acetate or palladium sulfate as a catalyst to obtain β-menadione, and the yield of the target product reached 50–64% [28]. However, the high concentration of H2O2 is prone to explosion, which limits the application of this method in industry. It has also been shown that 30% H2O2 was chosen to oxidize 2-methylnaphthalene with acetone as the reaction solvent [29]. The conversion rate of the raw material reached 45%, but the industrialization of this process is difficult to achieve due to the low boiling point of the solvent. Hence, it is particularly significant to find stable catalysts that can catalyze the oxidation of 2-methylnaphthalene with high yield using a suitable solvent. Based on the above research results, since insertion reactions by activating C–H bonds can react using silver complexes as catalysts, it is possible to activate C−H bonds by Ag(I) complexes to further oxidize 2-methylnaphthalene.

To verify this issue, polymerized methyl imidazole silver bromide was obtained, and the structure of the complex was characterized by elemental analysis, 1H nuclear magnetic resonance (NMR), and single-crystal X-ray diffraction. The catalytic activity of the Ag(I)-complex in the oxidation of 2-methylnaphthalene was investigated, and the catalytic mechanism is explored in this study. To the best of our knowledge, this is the first report on the synthesis, characterization, and catalytic activities of this complex.

2 Experimental method

2.1 Materials and reagents

Chromatographic-grade acetonitrile was purchased from Mreda Technology Inc. (USA); methylimidazole and 1,2-dibromoethane were purchased from Macklin Biochemical Technology Co., Ltd (Shanghai, China). Silver oxide was purchased from Aladdin Biochemical Technology Co., Ltd. (Shanghai, China). Other reagents used were purchased from Kelong Chemical Reagent Co. Ltd (Sichuan, China); distilled water and deionized water were obtained from a Spring-R10 water purification system (Research Scientific Instrument, Xiamen, China).

A Sartorius BSA224S-CW electronic balance (Germany) was employed to weigh the standard compounds. An SPM-20A LC system (Shimadzu Corporation, Japan), equipped with an LC-6AD binary pump, an SPD-M20A diode array detector with a wavelength range of 190–950 nm, a CTO-10AVP column oven, and Shimadzu CLASS-VP software (version 6), was used for the HPLC-DAD method. The separation of analytes was carried out on a C18-WR (255 × 4.6 mm, 5 μm) column, which was purchased from Shimadzu Corporation (Japan). A Bruker AVANCE Ⅲ HD 400 MHz NMR spectrometer with a superconducting magnet (Germany) was used to determine the NMR spectra. A Bruker Smart APEX Ⅱ single crystal X-ray diffractometer (Germany) was employed to characterize the steric structure of the complex.

2.2 Synthesis

Compound 1: Polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6 (1) was synthesized by the reaction of methylimidazole and 1,2-dibromoethane with Ag2O in THF at 60°C for 2 h. After refluxing, THF was removed under vacuum, and CH2Cl2 was added to recrystallize a white crystalline solid (Table 1).

Table 1

Crystallographic data and structure refinement parameters for Compound 1

Chemical formula C8H12Ag2Br2N4 Z 4
Formula weight 539.78 Radiation type MoKα (λ = 0.71073)
Crystal system Monoclinic µ (mm−1) 8.604
Space group P21/n Crystal size (mm) 0.18 × 0.16 × 0.14
Temperature (K) 296(2) F(000) 1008.0
a (Å) 8.916(4) Crystal density (g/m3) 2.597
b (Å) 17.655(9) Reflections collected 6,764
c (Å) 9.024(4) Independent reflections 3,118 [R int = 0.0453, R sigma = 0.0656]
α (°) 90 θ range for data collection (°) 4.614–55.112
β (°) 103.621(7) Data/restraints/parameters 3118/0/147
γ (°) 90 Goodness-of-fit on F 2 0.968
Volume (Å3) 1380.6(12) Final R indexes [I >= 2σ (I)] R1 = 0.0533, wR2 = 0.1387

2.3 Characterization

1H NMR spectra (400 MHz) were recorded and chemical shifts (δ) are reported in ppm.

Suitable crystals were selected for X-ray single crystal diffraction data for Compound 1 and were collected using a Bruker Smart APEX Ⅱ diffractometer (Germany). The crystal was kept at 296(2) K during data collection. Data reduction and analytical absorption correction were performed by the CrysAlisPro program. Intensity data were collected on a detector equipped with graphite-monochromatized MoKα radiation. The diffracted intensities were corrected for Lorentz-polarization effects and empirical absorption corrections. The structure was solved by direct methods. Non-hydrogen atoms were determined with successive difference Fourier syntheses. The hydrogen atoms were located at the calculated positions. The anisotropic thermal parameters for the non-hydrogen atoms were refined by full-matrix least-squares techniques on F 2. The crystal data, experimental details, and refinement results for Compound 1 are given in Table 2.

Table 2

Selected bond lengths (Å) of Compound 1

Bond Dist. Bond Dist.
Ag(1)−N(2) 2.262(7) Ag(2)−N(4) 2.261(6)
Ag(1)−Br(2) 2.7059(14) Ag(2)−Br(2) 2.6629(14)
Ag(1)−Br(1) 2.7267(14) Ag(2)−Br(1)2 2.7418(16)
Ag(1)−Br(1)1 2.7859(14) Ag(2)−Br(2)2 2.8943(16)
Ag(1)−Ag(2)2 3.0882(15) N(1)−C(3) 1.331(9)

2.4 Catalytic activities

2.4.1 Determination of the analysis methodt

Based on the external standard method by HPLC-DAD analysis, the content of 2-methylnaphthalene was determined, and the catalytic performance was evaluated by its conversion rate. To obtain a high resolution of 2-methylnaphthalene and β-menadione, the mobile phase was selected as 70% acetonitrile (A) and 30% water (B). The flow rate was 0.85 mL/min with an injection volume of 10 μL at a detection wavelength of 236 nm. The standard solutions were analyzed under the above conditions, and the peak area of each standard sample was determined. The regression equations were established using five concentration levels, and the standard curve was subsequently obtained using the concentration as the abscissa and the peak area as the ordinate.

2.4.2 Optimization of catalytic conditions

In an acetonitrile system, Compound 1 was used for the catalytic oxidation of 2-methylnaphthalene with hydrogen peroxide. The effects of catalyst dosage, oxidation dosage, reaction temperature, and reaction time on the catalysis of the oxidation of 2-methylnaphthalene were optimized by a single-factor test (Table 3).

Table 3

Selected bond angles (°) of Compound 1

Angle (o) Angle (o)
N(2)−Ag(1)−Br(2) 115.92(16) Br(1)2−Ag(2)−Br(2)2 107.94(4)
N(2)−Ag(1)−Br(1) 111.63(15) N(4)−Ag(2)−Ag(1)2 122.33(16)
Br(2)−Ag(1)−Br(1) 114.10(4) Br(2)−Ag(2)−Ag(1)2 116.08(5)
N(2)−Ag(1)−Br(1)1 108.73(16) Br(1)2−Ag(2)−Ag(1)2 55.39(3)
Br(2)−Ag(1)−Br(1)1 105.45(5) Br(2)2−Ag(2)−Ag(1)2 53.66(3)
Br(1)−Ag(1)−Br(1)1 99.31(4) Ag(1)−Br(1)−Ag(2)2 68.76(3)
N(2)−Ag(1)−Ag(2)2 127.16(16) Ag(1)−Br(1)−Ag(1)1 80.69(4)
Br(2)−Ag(1)−Ag(2)2 59.50(4) Ag(2)2−Br(1)−Ag(1)1 117.46(5)
Br(1)−Ag(1)−Ag(2)2 55.85(3) Ag(2)−Br(2)−Ag(1) 103.21(5)
Br(1)1−Ag(1)−Ag(2)2 123.51(4) Ag(2)−Br(2)−Ag(2)2 75.20(4)
N(4)−Ag(2)−Br(2) 120.60(16) Ag(1)−Br(2)−Ag(2)2 66.83(3)
N(4)−Ag(2)−Br(1)2 105.80(15) C(3)−N(2)−Ag(1) 129.1(5)
Br(2)−Ag(2)−Br(1)2 115.31(5) C(1)−N(2)−Ag(1) 125.6(5)
N(4)−Ag(2)−Br(2)2 100.84(16) C(7)−N(4)−Ag(2) 129.2(5)
Br(2)−Ag(2)−Br(2)2 104.80(4) C(5)−N(4)−Ag(2) 126.3(5)

Under the optimal catalytic conditions, the effects of the catalyst were investigated in this study.

3 Results and discussion

3.1 Synthesis

New polymerized methyl imidazole silver bromide was synthesized successfully by a one-pot process. The yield of Compound 1 was 73%. The structure of Compound 1 was characterized by 1H NMR, which was in accordance with previous studies [30,31,32].

Compound 1: C8H12Ag2Br2N4.

1H NMR (400 MHz, DMSO-d 6) δ 6.38 (2H), 6.16 (2H), 2.78 (2H), 1.59 (6H).

After complexation with Ag(I) metal, the chemical shift values of methyl imidazole decreased due to the electron absorption effects of the empty orbitals of silver atoms.

The elemental analysis of Compound 1 was as follows: the content of carbon was 32.67%, nitrogen was 8.49%, hydrogen was 1.83%, bromine was 24.22%, and silver was 32.69%, which verified the successful synthesis of Compound 1.

3.2 Description of the crystal structure of Compound 1

The definitive structure of Compound 1 was determined by X-ray diffraction. The crystal structure analysis showed that complex 1 is a mono-NHC of silver with bridging halides, and the geometry around the silver atom is pentacoordinated with silver and three bromine and nitrogen atoms of methyl imidazole. Two silver atoms are bridged by two bromine atoms to form a spatial quadrilateral, the Ag–Ag bond divides it into two triangles, and polymeric methyl imidazole silver bromide is formed based on this structure. The central silver atom possesses a distorted trigonal bipyramid, and the spatial structure of Ag2−X2 is a spatial quadrilateral because the sum of the bond angles of Br(2)−Ag(2)−Br(2)2, Br(1)2−Ag(2)−Br(2)2, Br(2)−Ag(2)−Ag(1)2, and Br(2)2−Ag(2)−Ag(1)2 deviate from 360°. Ag2−X2 allows for a strong interaction of Ag. Ag (3.0882 Å) is close to the Ag−Ag distance in silver metal (2.89 Å) [33]. Presumably, this is due to the low steric bulk of the N-functionalized methyl groups allowing the two imidazole rings to be bent toward one another [34]. The imidazole ring is a deformed pentagonal structure because the twist angles deviate from the ideal 0°. Because the bond angle of C(7)−N(4)−Ag(2) is not equal to 180°, the imidazole ring and the spatial quadrilateral are not coplanar. The bond angle of N(2)−Ag(1)−Br(2) is 115.92(16)°, which is smaller than the angle reported in the literature (162.5°) [35], which may be caused by the greater electron donating ability of nitrogen atoms. The bond lengths of Ag(1)−N(2) and Ag(2)−N(4) are 2.262(7) Å and 2.261(6) Å, which are longer than those of the reported complexes (2.111, 2.128, 2.144, and 2.148 Å) [36,37,38], which may be due to the diversity of coordination environments. The bond lengths of Ag(1)−Br(2) and Ag(1)−Br(1) are 2.7059(14) and 2.7267(14) Å, respectively, which are shorter than the bond lengths in reported complexes (3.189 and 2.762 Å) [39,40], suggesting that the coordination ability of silver atoms is stronger than that of cobalt and copper atoms.

3.3 Catalytic activities study

3.3.1 Validation of the HPLC-DAD method

The calibration curves of 2-methylnaphthalene had good linear regressions, and the correlated factor was 0.9990. The regression curve is as follows: Y = 19371x + 88940. The linear range was 16.45–205.60 μg/mL. This result showed that the HPLC-DAD method had good accuracy for the quantification of substrate (Figures 1 and 2).

Figure 1 The molecular structure of complex 1 (CCDC number: 2264839) (30% probability level).
Figure 1

The molecular structure of complex 1 (CCDC number: 2264839) (30% probability level).

Figure 2 The packing diagram of complex 1 (CCDC number: 2264839) (30% probability level).
Figure 2

The packing diagram of complex 1 (CCDC number: 2264839) (30% probability level).

3.3.2 Optimization of catalytic conditions

The effects of catalyst dose, oxidant dose, reaction temperature, and reaction time on the conversion of 2-methylnaphthalene were investigated by using a single-factor trial. By comparing the conversion of 2-methylnaphthalene, the optimal reaction conditions for the catalytic oxidation by complex 1 were determined. As shown in Figure 3, when the amount of catalyst is 5 and 10% of the substrate (w/w), the conversion rates of 2-methylnaphthalene are 28.83 and 37.31%, respectively. Fortunately, the conversion rate was much improved to 53.30% by using a catalyst amount of 15%. Therefore, the amount of catalyst was chosen as 15% of the substrate (w/w). The amount of hydrogen peroxide significantly affected the conversion rates of 2-methylnaphthalene. It could not effectively oxidize 2-methylnaphthalene if the amount was too low; however, this may cause changes in catalyst stability if the concentration of H2O2 is too high. Therefore, 2 mL was chosen as the final amount of H2O2 (when the mass of the substrate was 0.2 g). The reaction temperature was also a very important factor affecting the catalytic performance of Compound 1, and it affected the conversion rate of the substrate. As shown in Figure 3, we selected three different temperatures (60, 80, and 100℃) to optimize the conversion of 2-methylnaphthalene. The results showed that the conversion rate of 2-methylnaphthalene is the largest when the reaction temperature is 80°C. Time was also optimized for the reaction. If the reaction time is too short, it will lead to a low conversion rate. However, the economic cost will be reduced when the reaction time is too long. After comprehensive consideration, the reaction time was set at 3 h. The optimal conditions for the reaction were as follows: the amount of substrate was 0.2 g, the amount of catalyst was 0.03 g, the amount of oxidant was 2.0 mL, the reaction temperature was 80°C, and the reaction time was 3 h.

Figure 3 Optimization of reaction conditions.
Figure 3

Optimization of reaction conditions.

3.3.3 Catalytic effect of Compound 1

It is particularly significant to find stable catalysts that can catalyze the oxidation of 2-methylnaphthalene with a low concentration of H2O2 in a suitable solvent. In this study, the catalytic effects of complex 1 were evaluated when using 30% H2O2 as the oxidant and acetonitrile with a high boiling point as the solvent. Under the optimal conditions, the conversion rate of 2-methylnaphthalene without catalyst was 32.74%, and the conversion rate reached 77.15% when using complex 1 as the catalyst, with the yield of the target product reaching 63.48%. The results showed that the Ag(I) complex promoted the conversion of 2-methylnaphthalene with an excellent catalytic effect (Scheme 1).

Scheme 1 The structure and synthesis of Compound 1.
Scheme 1

The structure and synthesis of Compound 1.

3.4 Catalysis mechanism of Compound 1 in the oxidation of 2-methylnaphthalene

The catalysis mechanism is shown in Scheme 2. There are lone pair electrons on the oxygen atom in hydrogen peroxide, which could coordinate with the central Ag atom in Compound 1, increasing the electrophilicity of the oxygen atom and forming intermediate A. The electrophilicity of the Ag center has been increased simultaneously when translated into the metal complex intermediate A. Moreover, with the presence of imidazole rings, the coordination becomes more stable. The hydrogen atom on Compound B (2-methylnaphthalene) was attacked by the oxygen atom in intermediate A. Subsequently, the O–Ag bonds and –O–O bonds ruptured, 1,3 proton migration occurred, resulting in the formation of Compound C, and intermediate A reverted back to Compound 1. H+ has been released to generate Compound D. The oxygen atom in intermediate A, which displays partial positivity, could attack C of Compound D to generate Compound E. Eventually, target product F (β-naphthoquinone) is generated through a Bayer oxidation rearrangement. Intermediate A is highly electronegative, and it is not surprising that complex 1 has excellent catalytic activity for the oxidation of 2-methylnaphthalene.

Scheme 2 The catalysis mechanism of the oxidization of 2-methylnaphthalene.
Scheme 2

The catalysis mechanism of the oxidization of 2-methylnaphthalene.

4 Conclusion

A one-pot synthesis of a polymerized complex of silver(I) from methylimidazole and 1,2-dibromoethane with Ag2O is reported with a single crystal structure and catalytic application. In the complex, halogen serves as a bridging atom, and the silver atom possesses a distorted trigonal bipyramid that is coordinated with three bromine atoms, one silver atom, and one nitrogen atom on a methyl imidazole. The oxidation ability of H2O2 was enhanced by the properties of Compound 1, and 2-methylnaphthalene was oxidized efficiently with a conversion rate of 77.15%, and the yield of β-naphthoquinone reached 63.48%. These findings provide new catalytic systems for oxidation reactions by activating C–H bonds when using Ag(I) complexes as catalysts.

  1. Funding information: This research was funded by Dr. Scientific Research Fund from the Mianyang Normal University, Grant number QD2021A12.

  2. Author contributions: Conceptualization: A.X. and Z.W.; methodology: A.X.; investigation: A.X., F.P., and T.Y.; validation: F.P., and T.Y.; writing – original draft preparation: A.X.; writing-review and editing: Z.W.; project administration: Z.W.; funding acquisition: A.X. All authors have read and agreed to the published version of the manuscript.

  3. Conflict of interest: The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript; or in the decision to publish the results.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: All data generated or analyzed during this study are included in this published article and its supplementary information files.

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Received: 2023-07-04
Revised: 2023-08-29
Accepted: 2023-08-30
Published Online: 2023-10-11

© 2023 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/chem-2023-0122
Keywords for this article
polymerized silver bromide; imidazole; C–H bonds; 2-methylnaphthalene
Creative Commons
BY 4.0

Articles in the same Issue

  1. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  2. Regular Articles
  3. A network-based correlation research between element electronegativity and node importance
  4. Pomegranate attenuates kidney injury in cyclosporine-induced nephrotoxicity in rats by suppressing oxidative stress
  5. Ab initio study of fundamental properties of XInO3 (X = K, Rb, Cs) perovskites
  6. Responses of feldspathic sandstone and sand-reconstituted soil C and N to freeze–thaw cycles
  7. Robust fractional control based on high gain observers design (RNFC) for a Spirulina maxima culture interfaced with an advanced oxidation process
  8. Study on arsenic speciation and redistribution mechanism in Lonicera japonica plants via synchrotron techniques
  9. Optimization of machining Nilo 36 superalloy parameters in turning operation
  10. Vacuum impregnation pre-treatment: A novel method for incorporating mono- and divalent cations into potato strips to reduce the acrylamide formation in French fries
  11. Characterization of effective constituents in Acanthopanax senticosus fruit for blood deficiency syndrome based on the chinmedomics strategy
  12. Comparative analysis of the metabolites in Pinellia ternata from two producing regions using ultra-high-performance liquid chromatography–electrospray ionization–tandem mass spectrometry
  13. The assessment of environmental parameter along the desalination plants in the Kingdom of Saudi Arabia
  14. Effects of harpin and carbendazim on antioxidant accumulation in young jujube leaves
  15. The effects of in ovo injected with sodium borate on hatching performance and small intestine morphology in broiler chicks
  16. Optimization of cutting forces and surface roughness via ANOVA and grey relational analysis in machining of In718
  17. Essential oils of Origanum compactum Benth: Chemical characterization, in vitro, in silico, antioxidant, and antibacterial activities
  18. Translocation of tungsten(vi) oxide/gadolinium(iii) fluoride in tellurite glasses towards improvement of gamma-ray attenuation features in high-density glass shields
  19. Mechanical properties, elastic moduli, and gamma ray attenuation competencies of some TeO2–WO3–GdF3 glasses: Tailoring WO3–GdF3 substitution toward optimum behavioral state range
  20. Comparison between the CIDR or sponge with hormone injection to induce estrus synchronization for twining and sex preselection in Naimi sheep
  21. Exergetic performance analyses of three different cogeneration plants
  22. Psoralea corylifolia (babchi) seeds enhance proliferation of normal human cultured melanocytes: GC–MS profiling and biological investigation
  23. A novel electrochemical micro-titration method for quantitative evaluation of the DPPH free radical scavenging capacity of caffeic acid
  24. Comparative study between supported bimetallic catalysts for nitrate remediation in water
  25. Persicaline, an alkaloid from Salvadora persica, inhibits proliferation and induces apoptosis and cell-cycle arrest in MCF-7 cells
  26. Determination of nicotine content in locally produced smokeless tobacco (Shammah) samples from Jazan region of Saudi Arabia using a convenient HPLC-MS/MS method
  27. Changes in oxidative stress markers in pediatric burn injury over a 1-week period
  28. Integrated geophysical techniques applied for petroleum basins structural characterization in the central part of the Western Desert, Egypt
  29. The impact of chemical modifications on gamma-ray attenuation properties of some WO3-reinforced tellurite glasses
  30. Microwave and Cs+-assisted chemo selective reaction protocol for synthesizing 2-styryl quinoline biorelevant molecules
  31. Structural, physical, and radiation absorption properties of a significant nuclear power plant component: A comparison between REX-734 and 316L SS austenitic stainless steels
  32. Effect of Moringa oleifera on serum YKL-40 level: In vivo rat periodontitis model
  33. Investigating the impact of CO2 emissions on the COVID-19 pandemic by generalized linear mixed model approach with inverse Gaussian and gamma distributions
  34. Influence of WO3 content on gamma rays attenuation characteristics of phosphate glasses at low energy range
  35. Study on CO2 absorption performance of ternary DES formed based on DEA as promoting factor
  36. Performance analyses of detonation engine cogeneration cycles
  37. Sterols from Centaurea pumilio L. with cell proliferative activity: In vitro and in silico studies
  38. Untargeted metabolomics revealing changes in aroma substances in flue-cured tobacco
  39. Effect of pumpkin enriched with calcium lactate on iron status in an animal model of postmenopausal osteoporosis
  40. Energy consumption, mechanical and metallographic properties of cryogenically treated tool steels
  41. Optimization of ultra-high pressure-assisted extraction of total phenols from Eucommia ulmoides leaves by response surface methodology
  42. Harpin enhances antioxidant nutrient accumulation and decreases enzymatic browning in stored soybean sprouts
  43. Physicochemical and biological properties of carvacrol
  44. Radix puerariae in the treatment of diabetic nephropathy: A network pharmacology analysis and experimental validation
  45. Anti-Alzheimer, antioxidants, glucose-6-phosphate dehydrogenase effects of Taverniera glabra mediated ZnO and Fe2O3 nanoparticles in alloxan-induced diabetic rats
  46. Experimental study on photocatalytic CO2 reduction performance of ZnS/CdS-TiO2 nanotube array thin films
  47. Epoxy-reinforced heavy metal oxides for gamma ray shielding purposes
  48. Black mulberry (Morus nigra L.) fruits: As a medicinal plant rich in human health-promoting compounds
  49. Promising antioxidant and antimicrobial effects of essential oils extracted from fruits of Juniperus thurifera: In vitro and in silico investigations
  50. Chloramine-T-induced oxidation of Rizatriptan Benzoate: An integral chemical and spectroscopic study of products, mechanisms and kinetics
  51. Study on antioxidant and antimicrobial potential of chemically profiled essential oils extracted from Juniperus phoenicea (L.) by use of in vitro and in silico approaches
  52. Screening and characterization of fungal taxol-producing endophytic fungi for evaluation of antimicrobial and anticancer activities
  53. Mineral composition, principal polyphenolic components, and evaluation of the anti-inflammatory, analgesic, and antioxidant properties of Cytisus villosus Pourr leaf extracts
  54. In vitro antiproliferative efficacy of Annona muricata seed and fruit extracts on several cancer cell lines
  55. An experimental study for chemical characterization of artificial anterior cruciate ligament with coated chitosan as biomaterial
  56. Prevalence of residual risks of the transfusion-transmitted infections in Riyadh hospitals: A two-year retrospective study
  57. Computational and experimental investigation of antibacterial and antifungal properties of Nicotiana tabacum extracts
  58. Reinforcement of cementitious mortars with hemp fibers and shives
  59. X-ray shielding properties of bismuth-borate glass doped with rare earth ions
  60. Green supported silver nanoparticles over modified reduced graphene oxide: Investigation of its antioxidant and anti-ovarian cancer effects
  61. Orthogonal synthesis of a versatile building block for dual functionalization of targeting vectors
  62. Thymbra spicata leaf extract driven biogenic synthesis of Au/Fe3O4 nanocomposite and its bio-application in the treatment of different types of leukemia
  63. The role of Ag2O incorporation in nuclear radiation shielding behaviors of the Li2O–Pb3O4–SiO2 glass system: A multi-step characterization study
  64. A stimuli-responsive in situ spray hydrogel co-loaded with naringenin and gentamicin for chronic wounds
  65. Assessment of the impact of γ-irradiation on the piperine content and microbial quality of black pepper
  66. Antioxidant, sensory, and functional properties of low-alcoholic IPA beer with Pinus sylvestris L. shoots addition fermented using unconventional yeast
  67. Screening and optimization of extracellular pectinase produced by Bacillus thuringiensis SH7
  68. Determination of polyphenols in Chinese jujube using ultra-performance liquid chromatography–mass spectrometry
  69. Synergistic effects of harpin and NaCl in determining soybean sprout quality under non-sterile conditions
  70. Field evaluation of different eco-friendly alternative control methods against Panonychus citri [Acari: Tetranychidae] spider mite and its predators in citrus orchards
  71. Exploring the antimicrobial potential of biologically synthesized zero valent iron nanoparticles
  72. NaCl regulates goldfish growth and survival at three food supply levels under hypoxia
  73. An exploration of the physical, optical, mechanical, and radiation shielding properties of PbO–MgO–ZnO–B2O3 glasses
  74. A novel statistical modeling of air pollution and the COVID-19 pandemic mortality data by Poisson, geometric, and negative binomial regression models with fixed and random effects
  75. Treatment activity of the injectable hydrogels loaded with dexamethasone In(iii) complex on glioma by inhibiting the VEGF signaling pathway
  76. An alternative approach for the excess lifetime cancer risk and prediction of radiological parameters
  77. Panax ginseng leaf aqueous extract mediated green synthesis of AgNPs under ultrasound condition and investigation of its anti-lung adenocarcinoma effects
  78. Study of hydrolysis and production of instant ginger (Zingiber officinale) tea
  79. Novel green synthesis of zinc oxide nanoparticles using Salvia rosmarinus extract for treatment of human lung cancer
  80. Evaluation of second trimester plasma lipoxin A4, VEGFR-1, IL-6, and TNF-α levels in pregnant women with gestational diabetes mellitus
  81. Antidiabetic, antioxidant and cytotoxicity activities of ortho- and para-substituted Schiff bases derived from metformin hydrochloride: Validation by molecular docking and in silico ADME studies
  82. Antioxidant, antidiabetic, antiglaucoma, and anticholinergic effects of Tayfi grape (Vitis vinifera): A phytochemical screening by LC-MS/MS analysis
  83. Identification of genetic polymorphisms in the stearoyl CoA desaturase gene and its association with milk quality traits in Najdi sheep
  84. Cold-acclimation effect on cadmium absorption and biosynthesis of polyphenolics, and free proline and photosynthetic pigments in Spirogyra aequinoctialis
  85. Analysis of secondary metabolites in Xinjiang Morus nigra leaves using different extraction methods with UPLC-Q/TOF-MS/MS technology
  86. Nanoarchitectonics and performance evaluation of a Fe3O4-stabilized Pickering emulsion-type differential pressure plugging agent
  87. Investigating pyrolysis characteristics of Shengdong coal through Py-GC/MS
  88. Extraction, phytochemical characterization, and antifungal activity of Salvia rosmarinus extract
  89. Introducing a novel and natural antibiotic for the treatment of oral pathogens: Abelmoschus esculentus green-formulated silver nanoparticles
  90. Optimization of gallic acid-enriched ultrasonic-assisted extraction from mango peels
  91. Effect of gamma rays irradiation in the structure, optical, and electrical properties of samarium doped bismuth titanate ceramics
  92. Combinatory in silico investigation for potential inhibitors from Curcuma sahuynhensis Škorničk. & N.S. Lý volatile phytoconstituents against influenza A hemagglutinin, SARS-CoV-2 main protease, and Omicron-variant spike protein
  93. Physical, mechanical, and gamma ray shielding properties of the Bi2O3–BaO–B2O3–ZnO–As2O3–MgO–Na2O glass system
  94. Twofold interpenetrated 3D Cd(ii) complex: Crystal structure and luminescent property
  95. Study on the microstructure and soil quality variation of composite soil with soft rock and sand
  96. Ancient spring waters still emerging and accessible in the Roman Forum area: Chemical–physical and microbiological characterization
  97. Extraction and characterization of type I collagen from scales of Mexican Biajaiba fish
  98. Finding small molecular compounds to decrease trimethylamine oxide levels in atherosclerosis by virtual screening
  99. Prefatory in silico studies and in vitro insecticidal effect of Nigella sativa (L.) essential oil and its active compound (carvacrol) against the Callosobruchus maculatus adults (Fab), a major pest of chickpea
  100. Polymerized methyl imidazole silver bromide (CH3C6H5AgBr)6: Synthesis, crystal structures, and catalytic activity
  101. Using calcined waste fish bones as a green solid catalyst for biodiesel production from date seed oil
  102. Influence of the addition of WO3 on TeO2–Na2O glass systems in view of the feature of mechanical, optical, and photon attenuation
  103. Naringin ameliorates 5-fluorouracil elicited neurotoxicity by curtailing oxidative stress and iNOS/NF-ĸB/caspase-3 pathway
  104. GC-MS profile of extracts of an endophytic fungus Alternaria and evaluation of its anticancer and antibacterial potentialities
  105. Green synthesis, chemical characterization, and antioxidant and anti-colorectal cancer effects of vanadium nanoparticles
  106. Determination of caffeine content in coffee drinks prepared in some coffee shops in the local market in Jeddah City, Saudi Arabia
  107. A new 3D supramolecular Cu(ii) framework: Crystal structure and photocatalytic characteristics
  108. Bordeaux mixture accelerates ripening, delays senescence, and promotes metabolite accumulation in jujube fruit
  109. Important application value of injectable hydrogels loaded with omeprazole Schiff base complex in the treatment of pancreatitis
  110. Color tunable benzothiadiazole-based small molecules for lightening applications
  111. Investigation of structural, dielectric, impedance, and mechanical properties of hydroxyapatite-modified barium titanate composites for biomedical applications
  112. Metal gel particles loaded with epidermal cell growth factor promote skin wound repair mechanism by regulating miRNA
  113. In vitro exploration of Hypsizygus ulmarius (Bull.) mushroom fruiting bodies: Potential antidiabetic and anti-inflammatory agent
  114. Alteration in the molecular structure of the adenine base exposed to gamma irradiation: An ESR study
  115. Comprehensive study of optical, thermal, and gamma-ray shielding properties of Bi2O3–ZnO–PbO–B2O3 glasses
  116. Lewis acids as co-catalysts in Pd-based catalyzed systems of the octene-1 hydroethoxycarbonylation reaction
  117. Synthesis, Hirshfeld surface analysis, thermal, and selective α-glucosidase inhibitory studies of Schiff base transition metal complexes
  118. Protective properties of AgNPs green-synthesized by Abelmoschus esculentus on retinal damage on the virtue of its anti-inflammatory and antioxidant effects in diabetic rat
  119. Effects of green decorated AgNPs on lignin-modified magnetic nanoparticles mediated by Cydonia on cecal ligation and puncture-induced sepsis
  120. Treatment of gastric cancer by green mediated silver nanoparticles using Pistacia atlantica bark aqueous extract
  121. Preparation of newly developed porcelain ceramics containing WO3 nanoparticles for radiation shielding applications
  122. Utilization of computational methods for the identification of new natural inhibitors of human neutrophil elastase in inflammation therapy
  123. Some anticancer agents as effective glutathione S-transferase (GST) inhibitors
  124. Clay-based bricks’ rich illite mineral for gamma-ray shielding applications: An experimental evaluation of the effect of pressure rates on gamma-ray attenuation parameters
  125. Stability kinetics of orevactaene pigments produced by Epicoccum nigrum in solid-state fermentation
  126. Treatment of denture stomatitis using iron nanoparticles green-synthesized by Silybum marianum extract
  127. Characterization and antioxidant potential of white mustard (Brassica hirta) leaf extract and stabilization of sunflower oil
  128. Characteristics of Langmuir monomolecular monolayers formed by the novel oil blends
  129. Strategies for optimizing the single GdSrFeO4 phase synthesis
  130. Oleic acid and linoleic acid nanosomes boost immunity and provoke cell death via the upregulation of beta-defensin-4 at genetic and epigenetic levels
  131. Unraveling the therapeutic potential of Bombax ceiba roots: A comprehensive study of chemical composition, heavy metal content, antibacterial activity, and in silico analysis
  132. Green synthesis of AgNPs using plant extract and investigation of its anti-human colorectal cancer application
  133. The adsorption of naproxen on adsorbents obtained from pepper stalk extract by green synthesis
  134. Treatment of gastric cancer by silver nanoparticles encapsulated by chitosan polymers mediated by Pistacia atlantica extract under ultrasound condition
  135. In vitro protective and anti-inflammatory effects of Capparis spinosa and its flavonoids profile
  136. Wear and corrosion behavior of TiC and WC coatings deposited on high-speed steels by electro-spark deposition
  137. Therapeutic effects of green-formulated gold nanoparticles by Origanum majorana on spinal cord injury in rats
  138. Melanin antibacterial activity of two new strains, SN1 and SN2, of Exophiala phaeomuriformis against five human pathogens
  139. Evaluation of the analgesic and anesthetic properties of silver nanoparticles supported over biodegradable acacia gum-modified magnetic nanoparticles
  140. Review Articles
  141. Role and mechanism of fruit waste polyphenols in diabetes management
  142. A comprehensive review of non-alkaloidal metabolites from the subfamily Amaryllidoideae (Amaryllidaceae)
  143. Discovery of the chemical constituents, structural characteristics, and pharmacological functions of Chinese caterpillar fungus
  144. Eco-friendly green approach of nickel oxide nanoparticles for biomedical applications
  145. Advances in the pharmaceutical research of curcumin for oral administration
  146. Rapid Communication
  147. Determination of the contents of bioactive compounds in St. John’s wort (Hypericum perforatum): Comparison of commercial and wild samples
  148. Retraction
  149. Retraction of “Two mixed-ligand coordination polymers based on 2,5-thiophenedicarboxylic acid and flexible N-donor ligands: The protective effect on periodontitis via reducing the release of IL-1β and TNF-α”
  150. Topical Issue on Phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  151. Anti-plasmodial potential of selected medicinal plants and a compound Atropine isolated from Eucalyptus obliqua
  152. Anthocyanin extract from black rice attenuates chronic inflammation in DSS-induced colitis mouse model by modulating the gut microbiota
  153. Evaluation of antibiofilm and cytotoxicity effect of Rumex vesicarius methanol extract
  154. Chemical compositions of Litsea umbellata and inhibition activities
  155. Green synthesis, characterization of silver nanoparticles using Rhynchosia capitata leaf extract and their biological activities
  156. GC-MS analysis and antibacterial activities of some plants belonging to the genus Euphorbia on selected bacterial isolates
  157. The abrogative effect of propolis on acrylamide-induced toxicity in male albino rats: Histological study
  158. A phytoconstituent 6-aminoflavone ameliorates lipopolysaccharide-induced oxidative stress mediated synapse and memory dysfunction via p-Akt/NF-kB pathway in albino mice
  159. Anti-diabetic potentials of Sorbaria tomentosa Lindl. Rehder: Phytochemistry (GC-MS analysis), α-amylase, α-glucosidase inhibitory, in vivo hypoglycemic, and biochemical analysis
  160. Assessment of cytotoxic and apoptotic activities of the Cassia angustifolia aqueous extract against SW480 colon cancer
  161. Biochemical analysis, antioxidant, and antibacterial efficacy of the bee propolis extract (Hymenoptera: Apis mellifera) against Staphylococcus aureus-induced infection in BALB/c mice: In vitro and in vivo study
  162. Assessment of essential elements and heavy metals in Saudi Arabian rice samples underwent various processing methods
  163. Two new compounds from leaves of Capparis dongvanensis (Sy, B. H. Quang & D. V. Hai) and inhibition activities
  164. Hydroxyquinoline sulfanilamide ameliorates STZ-induced hyperglycemia-mediated amyleoid beta burden and memory impairment in adult mice
  165. An automated reading of semi-quantitative hemagglutination results in microplates: Micro-assay for plant lectins
  166. Inductively coupled plasma mass spectrometry assessment of essential and toxic trace elements in traditional spices consumed by the population of the Middle Eastern region in their recipes
  167. Phytochemical analysis and anticancer activity of the Pithecellobium dulce seed extract in colorectal cancer cells
  168. Impact of climatic disturbances on the chemical compositions and metabolites of Salvia officinalis
  169. Physicochemical characterization, antioxidant and antifungal activities of essential oils of Urginea maritima and Allium sativum
  170. Phytochemical analysis and antifungal efficiency of Origanum majorana extracts against some phytopathogenic fungi causing tomato damping-off diseases
  171. Special Issue on 4th IC3PE
  172. Graphene quantum dots: A comprehensive overview
  173. Studies on the intercalation of calcium–aluminium layered double hydroxide-MCPA and its controlled release mechanism as a potential green herbicide
  174. Synergetic effect of adsorption and photocatalysis by zinc ferrite-anchored graphitic carbon nitride nanosheet for the removal of ciprofloxacin under visible light irradiation
  175. Exploring anticancer activity of the Indonesian guava leaf (Psidium guajava L.) fraction on various human cancer cell lines in an in vitro cell-based approach
  176. The comparison of gold extraction methods from the rock using thiourea and thiosulfate
  177. Special Issue on Marine environmental sciences and significance of the multidisciplinary approaches
  178. Sorption of alkylphenols and estrogens on microplastics in marine conditions
  179. Cytotoxic ketosteroids from the Red Sea soft coral Dendronephthya sp.
  180. Antibacterial and biofilm prevention metabolites from Acanthophora spicifera
  181. Characteristics, source, and health risk assessment of aerosol polyaromatic hydrocarbons in the rural and urban regions of western Saudi Arabia
  182. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part II
  183. Green synthesis, characterization, and evaluation of antibacterial activities of cobalt nanoparticles produced by marine fungal species Periconia prolifica
  184. Combustion-mediated sol–gel preparation of cobalt-doped ZnO nanohybrids for the degradation of acid red and antibacterial performance
  185. Perinatal supplementation with selenium nanoparticles modified with ascorbic acid improves hepatotoxicity in rat gestational diabetes
  186. Evaluation and chemical characterization of bioactive secondary metabolites from endophytic fungi associated with the ethnomedicinal plant Bergenia ciliata
  187. Enhancing photovoltaic efficiency with SQI-Br and SQI-I sensitizers: A comparative analysis
  188. Nanostructured p-PbS/p-CuO sulfide/oxide bilayer heterojunction as a promising photoelectrode for hydrogen gas generation
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