Sulfide Derivatives Research Articles

A Green Route to Benzyl Phenyl Sulfide from Thioanisole and Benzyl Alcohol over Dual Functional Ionic Liquids.

Benzyl phenyl sulfide is a kind of important chemicals with wide usage, which is mainly prepared through a nucleophilic reaction of thiophenol with benzyl chlorides or benzyl alcohols, suffering from inherent drawbacks, such as low efficiency, requirements for equivalent acid or base catalysts and formation of harmful byproducts and waste. Herein, we report a green route to access various benzyl phenyl sulfide derivatives in good to excellent yields under mild conditions via the reaction of thioanisoles with benzyl alcohols over ionic liquid 1-propylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO3 HPrMIm][OTf]). Mechanism investigation indicates that the synergic effect of cation and anion of [SO3 HPrMIm][OTf] activates thioanisoles and benzyl alcohols via hydrogen bonding, thus catalyzes the dehydration of benzyl alcohol to dibenzyl ether and the subsequent metathesis reaction between dibenzyl ether and benzyl phenyl sulfide, finally generating benzyl phenyl sulfide derivatives. This is a simple, highly efficient, and green approach to produce benzyl phenyl sulfide derivatives, which has promising application potentials.

Utilisation of bis-chloroacetamide derivative in the synthesis of new biologically active sulfide compounds

4-Aminobenzohydrazide (1) undergoes chloroacetylation twice, at the primary amine and hydrazide-NH2 functional groups. The conforming bis-chloroacetamide derivative 3 was reacted with different sulfur reagents (namely, 2-mercaptobenzothiazole, 6-amino-2-mercaptopyrimidin-4-ol, and 2-mercapto-4,6-dimethyl-nicotinonitrile) to give new bis-sulfide compounds 5, 7 and 9, respectively. The newly synthesised bis-chloroacetamide and corresponding sulfides were screened for anti-microbial and antioxidant potential. The sulfide derivative 7 exhibited the most potent activity against Staphylococcus aureus and Pseudomonas aeruginosa. It shows inhibition activities of 83.4% and 78.8%, respectively. Moreover, the sulfide derivative 7 showed the highest antioxidant activity with an inhibition ratio of 85.9%, which is close to L-ascorbic acid.

A new copper-supported zinc ferrite as a heterogeneous magnetic nanocatalyst for the synthesis of bis(pyrazolyl)methanes and oxidation of sulfides

In this paper, we report the synthesis of ZnFe2O4@SiO2@APTES@DHBS-Cu as a novel magnetic nanocatalyst, in a mild and green environment. The structure of the described magnetic compound was characterized by different physicochemical techniques including XRD, EDS, AAS, SEM, FT-IR, X-ray elemental mapping, TGA, and VSM analyses. The prepared magnetic nanoparticles exhibit excellent catalytic activity in synthesizing bis (pyrazolyl)methanes and oxidation of sulfide derivatives under green conditions. The heterogeneous nature of the catalyst was confirmed via the hot filtration experiment. Further, ZnFe2O4@SiO2@APTES@DHBS-Cu showed high efficiency and reusability that could be reused for at least five consecutive runs.

Efficient heavy metal recycling and water reuse from industrial wastewater using new reusable and inexpensive polyphenylene sulfide derivatives

Heavy metal (HM) pollution is a serious environment problem. Recovering HM from industrial wastewater by efficient adsorbents is a sustainable method due to recycling HM and acquiring reusable water. However, popular efficient adsorbents are usually expensive or non-reusable. In this paper, methods of efficient HM recycling and water reuse from industrial wastewater were developed using efficient adsorbents, new polyphenylene sulfide derivatives, which are recyclable and stable in an acidic, alkaline or oxidative aqueous solution. Moreover, they can efficiently and quickly adsorb HM ions. The maximum adsorption capacities of these adsorbents for HM ions are at the range from 51.3–184.2 mg·g−1. The adsorption equilibrium times of them for HM ions are at the range from 10 to 80 min. Therefore, this paper suggests sustainable methods of HM recovery and water reuse from industrial wastewater.

Design and Synthesis of Phenyl Sulfide-Based Cationic Amphiphiles as Membrane-Targeting Antimicrobial Agents against Gram-Positive Pathogens.

Due to the emergence of antimicrobial resistance and the lack of new antibacterial agents, it has become urgent to discover and develop new antibacterial agents against multidrug-resistant pathogens. Antimicrobial peptides (AMPs) serve as the first line of defense for the host. In this work, we have designed, synthesized, and biologically evaluated a series of phenyl sulfide derivatives by biomimicking the structural features and biological functions of AMPs. Among these derivatives, the most promising compound 17 exhibited potent antibacterial activity against Gram-positive bacteria (minimum inhibitory concentrations = 0.39-1.56 μg/mL), low hemolytic activity (HC50 > 200 μg/mL), and high membrane selectivity. In addition, 17 can rapidly kill Gram-positive bacteria within 0.5 h through membrane-targeting action and avoid antibiotic resistance. More importantly, 17 showed high in vivo efficacy against Staphylococcus aureus in a murine corneal infection model. Therefore, 17 has great potential as a lead compound for the treatment of Gram-positive bacterial infections.

Transcending the Trade-off in Refractive Index and Abbe Number for Highly Refractive Polymers: Synergistic Effect of Polarizable Skeletons and Robust Hydrogen Bonds.

High-refractive-index polymers (HRIPs) are attractive materials for the development of optical devices with high performances. However, because practical components and structures for HRIPs are limited from the viewpoint of synthetic techniques, it has proved difficult using traditional strategies to enhance the refractive index (RI) of HRIPs to more than a certain degree (over 1.8) while maintaining their visible transparency. Here, we found that poly(phenylene sulfide) (PPS) derivatives featuring both methylthio and hydroxy groups can simultaneously exhibit balanced properties of an ultrahigh RI of n D = 1.85 and Abbe number of νD = 20 owing to the synergistic effect of high molar refraction and dense intermolecular hydrogen bonds (H-bonds). This brand new strategy is anticipated to contribute to the development of HRIPs displaying ultrahigh RI with adequate Abbe numbers beyond the empirical n D-νD threshold, which has not been achieved to date.

Cadmium sulfide in-situ derived heterostructure hybrids with tunable component ratio for highly sensitive and selective detection of ppb-level H2S

Herein, we reported cadmium sulfide derivatives pine needles-like CdS/CdO heterostructure hybrids synthesized by hydrothermal treatment and subsequent self-template oxidation approach. The component ratio of the CdS/CdO hybrids can be controlled specifically via tuning the annealing treatment protocol, and thereby giving rise to the optimization of morphology, electrical characteristics, and gas sensing properties of derived hybrids. As proof of concept, the pine needles-like CdS/CdO, which obtained after different annealing temperatures and durations, as sensitive material was employed to manufacture H2S gas sensors. The sensor based on CdS/CdO hybrids (400 °C & 1 h) exhibited high sensitivity (73.5 to 5 ppm), ppb-level limit of detection (10 ppb), and excellent selectivity regardless of the interference of other gases at optimal working temperature of 200 °C. Due to the abnormal resistance variation of n-type cadmium sulfide derived hybrids while contacting with H2S, the sensing mechanism mainly depends on the surface chemical conversion from oxide to sulfide. The pine needles-like hierarchical morphology provided an excellent scaffold for the carriers transportation and the growth of the CdO, which played a key role in resistance modulation both in air and target gas, resulting in the enhanced H2S sensing performance ultimately.

Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives.

A short synthetic route to stereoselective access to C-glycosyl-aminoethyl sulfide derivatives has been developed through the reaction of tributhyltin derivatives of glycals with aziridinecarboaldehyde and the regioselective ring opening of a chiral aziridine with thiophenol. The absolute configurations of the resulting diastereoisomers were determined by 1H NMR spectroscopy.

Construction of advanced zeolitic imidazolate framework derived cobalt sulfide/MXene composites as high-performance electrodes for supercapacitors

The Ti3C2Tx with excellent conductivity is used in a novel cobalt-based ZIF-67/Ti3C2Tx composites, sulfide derivative (Co3S4/Ti3C2Tx) of which is then applied as an active supercapacitor material. The specific capacitance of ZIF-67/Ti3C2Tx is significantly higher than that of unmodified ZIF-67. The sulfide-containing derivatives of these compounds demonstrated pseudocapacitance. The specific capacitance of an electrode containing Co3S4/Ti3C2Tx as an active material is very high and equal to 602F/g at 1 A/g, which is 2.6 times higher than of a ZIF-67/Ti3C2Tx-containing electrode. The supercapacitor based on Co3S4/Ti3C2Tx maintained 81.6% of its original capacitance even at 10 A/g current density. Thus, the introduction of Ti3C2Tx into the ZIF-67 improves not only the electrical conductivity of the hybrid material but also its structural stability, which allows to act as support. An asymmetric Co3S4/Ti3C2Tx//AC supercapacitor (ASC) containing activated carbon (AC) as an anode showed a high energy density equal to 44.9 Wh/kg at 800.3 W/kg power density. This ASC also demonstrated high rate-performance (equal to 79.2%) and excellent cycling stability (with 88.3% capacitance retention and 99.23% Coulombic efficiency after 5000 cycles). The excellent electrochemical performance of our novel composite and conductivity, as well as the stability of its three-dimensional (3D) structure, make it a very promising material for energy storage applications.

Synthesis of colorless and high-refractive-index sulfoxide-containing polymers by the oxidation of poly(phenylene sulfide) derivatives

A series of poly(phenylene sulfide) (PPS) derivatives can be bleached while maintaining high refractive indices, by partially incorporating sulfoxide bonds through their mCPBA oxidation, owing to the loss of lone pairs around the sulfide atoms.

Synthesis and Characterization of 1,4-Benzodioxane-6-Carboxylic Acid Amide Analogs

A library of new 1,4-benzodioxane-6-carboxylic acid amide analogs was designed and synthesized. These analogs were obtained in six steps from gallic acid. Firstly, esterification of the commercially available gallic acid in methanol in the presence of sulfuric acid afforded methyl 3,4,5-trihydroxybenzoate (9) in satisfactory yield. The ester 9 was then reacted with an excess of 1,2-dibromoethane in the presence of K2CO3 in acetone to furnish the 6,8-disubstituted-1,4-benzodioxane (10) in 45% yield. The reaction of 10 with various mercaptans gave the sulfide derivative 11, 12, and 13 in moderate yield. Subsequent hydrolysis of the methyl ester in 13 followed by conversion to the acid chloride and reaction of the acid chloride intermediate with different commercially available primary and secondary amines gave the amide analogs 18 - 32 with an average yield of 43%. Conversion of the sulfide group in Compound 23 to Sulfoxide 33 or Sulfone 34 was accomplished by reaction with either 30% H2O2/TeO2 or 30% H2O2, respectively. The structures of the synthesized compounds were characterized using FTIR, 1H-NMR, 13C-NMR, and high-resolution ESI-MS.

Efficient Heavy Metal Recycling and Water Reuse from Industrial Wastewater Using New Reusable and Inexpensive Polyphenylene Sulfide Derivatives as Adsorbents

Efficient Heavy Metal Recycling and Water Reuse from Industrial Wastewater Using New Reusable and Inexpensive Polyphenylene Sulfide Derivatives as Adsorbents

Synthesis, reactivity and transition metal complexes of 1,1′-bis(diethynylphosphino)ferrocene

The synthesis, oxidation reactions and transition metal complexes of a new ferrocenyl-bisphosphine, [Fe{C5H4P(C≡CH)2}2] (1), are described. The reaction of bis(dichlorophosphino)ferrocene with four equivalents of ethynylmagnesium bromide resulted in the formation of 1 in 76% yield. The reaction between 1, aqueous H2O2 or elemental sulphur produced bis(oxide) and bis(sulfide) derivatives, [Fe{C5H4P(E)(C≡CH)2}2] (2 E = O, 3 E = S). Reaction of 1 with [Ru(η 6-p-cymene)Cl2]2 yielded a diruthenium complex [Fe{C5H4P(C≡CH)2}2{RuCl2(η 6-p-cymene)}2] (4). Treatment of 1 with [M(COD)Cl2] (M = Pd, Pt) resulted in [Fe{C5H4P(C≡CH)2}2{MCl2}] (5 M = Pd, 6 M = Pt). Equimolar reactions between 1 and CuX produced binuclear complexes, [Fe{C5H4P(C≡CH)2}2{CuX}2] (7 X = Cl, 8 X = Br, 9 X = I).

Diaryl Sulfide Derivatives as Potential Iron Corrosion Inhibitors: A Computational Study.

The present work aimed to assess six diaryl sulfide derivatives as potential corrosion inhibitors. These derivatives were compared with dapsone (4,4′-diaminodiphenyl sulfone), a common leprosy antibiotic that has been shown to resist the corrosion of mild steel in acidic media with a corrosion efficiency exceeding 90%. Since all the studied compounds possess a common molecular backbone (diphenyl sulfide), dapsone was taken as the reference compound to evaluate the efficiency of the remainder. In this respect, two structural factors were examined, namely, (i) the effect of replacement of the S-atom of diaryl sulfide by SO or SO2 group, (ii) the effect of the introduction of an electron-withdrawing or an electron-donating group in the aryl moiety. Two computational chemical approaches were used to achieve the objectives: the density functional theory (DFT) and the Monto Carlo (MC) simulation. First, B3LYP/6-311+G(d,p) model chemistry was employed to calculate quantum chemical descriptors of the studied molecules and their geometric and electronic structures. Additionally, the mode of adsorption of the tested molecules was investigated using MC simulation. In general, the adsorption process was favorable for molecules with a lower dipole moment. Based on the adsorption energy results, five diaryl sulfide derivatives are expected to act as better corrosion inhibitors than dapsone.

One Functionalized Polyoxovanadates Hybrid Material Based on Arsonic Acid with Highly Effective Catalytic Property of Sulfides

In this work, a novel 4-aminophenylarsonic acid functionalized polyoxovanadates (POVs) hybrid material, namely, (Me2NH2)4 ·[(L)8(H12V16O32)] (H2L = 4-NH2C6H4AsO3H2) POVs 1 was solvothermally synthesized and fully characterized. The results revealed POVs 1 consists of four similar tetranuclear vanadium clusters bridged by eight organic 4-aminophenylarsonic acid ligands. Remarkably, functionalized hybrid POVs 1 was further investigated as a heterogeneous stable catalyst in oxidation of sulfide derivatives, and exhibited high catalytic activities (yields up to 96.7%). Additionally, the functionalized hybrid polyoxovanadates catalyst can be reused without losing activities after three runs cycle.

Indium‐Catalyzed Deoxygenation of Sulfoxides with Hydrosilanes

AbstractDescribed herein is that a novel InBr3/PhSiH3 reducing system in a 1,4‐dioxane solution smoothly and effectively undertook deoxygenation of a variety of sulfoxides leading to the facile preparation of sulfide derivatives. Also, it was demonstrated that the reducing system shows a higher reactivity towards sulfoxides than that towards commonly reducible functional groups, such as carboxylic acids, esters, amides, and sulfones.

Genomic and Physiological Investigation of Heavy Metal Resistance from Plant Endophytic Methylobacterium radiotolerans MAMP 4754, Isolated from Combretum erythrophyllum.

Combretum erythrophyllum is an indigenous southern African tree species, a metal hyperaccumulator that has been used as a phytoextraction option for tailing dams in Johannesburg, South Africa. In hyperaccumulators, metal detoxification has also been linked or attributed to the activities of endophytes, and, in this regard, metal detoxification can be considered a form of endophytic behavior. Therefore, we report herein on the identification of proteins that confer heavy metal resistance, the in vitro characterization of heavy metal resistance, and the production of plant growth-promoting (PGP) volatiles by Methylobacterium radiotolerans MAMP 4754. Multigenome comparative analyses of M. radiotolerans MAMP 4754 against eight other endophytic strains led to the identification of zinc, copper, and nickel resistance proteins in the genome of this endophyte. The maximum tolerance concentration (MTC) of this strain towards these metals was also investigated. The metal-exposed cells were analyzed by transmission electron microscopy (TEM). The ethyl acetate and chloroform extracts (1:1 v/v) of heavy metal untreated M. radiotolerans MAMP 4754 were also screened for the production of PGP compounds by Gas Chromatography–Mass Spectroscopy (GC/MS). The MTC was recorded at 15 mM, 4 mM, and 12 mM for zinc, copper, and nickel, respectively. The TEM analysis showed the accumulation of metals in the intracellular environment of M. radiotolerans MAMP 4754, while the GC/MS analysis revealed several plant growth-promoting compounds, including alcohols, phthalate esters, alkenes, ketones, sulfide derivatives, phenols, and thiazoles. Our findings suggest that the genetic makeup of M. radiotolerans MAMP 4754 encodes heavy metal resistant proteins that indicate hyperaccumulator-specific endophytic behavior and the potential for application in bioremediation. The production of plant growth-promoting volatiles in pure culture by M. raditotolerans MAMP 4754 is a characteristic feature for plant growth-promoting bacteria.

THERAPEUTIC ACTION OF HINGU IN RESPIRATORY SYSTEM: A LITERARY REVIEW

Man has been struggling to get remedies for various life-threatening disorders which are common in the day to day life of the busy world. Many lifestyle disorders such as diabetes mellitus, hypertension, dyslipidemia, thyroid dysfunction, respiratory disorders, skin diseases, etc. arise due to incompatible diet, polluted atmosphere, sedentary life style, lack of exercise, lack of proper sleep, etc. Ayurveda, the science of life, advices to follow Dinacharya, Ritucharya, Sadvritta etc for the benefit of the common man to enhance longevity. Ayurveda utilizes the wide range of herbal drugs either as single drug or in combination for the purpose of health care remedies. The phyto constituents present in these drugs play the major role in treating the diseases. Ferula foetida, known as Hingu in Ayurveda has promising therapeutic value due to the presence of chemical constituents like sulphide derivatives, volatile oil etc. Many studies revealed the various pharmacological actions of Hingu such as carminative, antispasmodic, antimicrobial, antioxidant, etc. This review highlights the available information on the drug Hingu by due consideration to the action of Hingu on the respiratory system and the formulations with Hingu as an ingredient as available in the Ayurvedic texts in treating respiratory disorders. Some other aspects are also discussed in the review.

A novel magnetic functionalized m-carboxyphenyl azo calix[4]arene symmetric sulfide derivative: synthesis and application as a selective adsorbent for removal of U (VI)

A novel adsorbent magnetic functionalized m-carboxyphenyl azo calix[4]arene symmetrical sulfide derivative (Fe3O4/M-CCSSD) was fabricated by a series of simple reactions and characterized by FT-IR and SEM. The effects on U (VI) adsorption process were investigated at several conditions. The calculated data disclose that the adsorption process of U (VI) by Fe3O4/M-CCSSD is an endothermic spontaneous process, which well fits with the pseudo-second-order kinetic and Freundlich isotherm model. In the most favorable conditions, accounting for approximately 89% of U (VI) was removed. In addition, Fe3O4/M-CCSSD showed high selectivity for U (VI) and exceptional reusability.

Study of the in vivo antiviral activity against TMV treated with novel 1-(t-butyl)-5-amino-4-pyrazole derivatives containing a 1,3,4-oxadiazole sulfide moiety

A series of new 1-tert-butyl-5-amino-4-pyrazole bioxadiazole sulfide derivatives containing a 1,3,4-oxadiazole moiety were designed and synthesized. The bioactivity results showed that some title compounds exhibited excellent protective activity against TMV and certain insecticidal activity. Among the tested compounds, the EC50 values of 5d, 5j, 5k and 5l were 165.8, 163.2, 159.7 and 193.1 mg/L, respectively, which are better than the EC50 value of ningnanmycin (271.3 mg/L). The chlorophyll contents and the defense enzyme activities of the tobacco leaves after treatment with 5j were significantly increased, which indicated that this series of title compounds may induce the systemic acquired resistance of host to defend against diseases. Further in vivo protective activity research on 5j using TMV with a GFP gene tag found that it can effectively inhibit the spread of TMV in inoculated tobacco. A morphological study with TEM revealed that title compound 5h can cause a distinct break of the rod-shaped TMV. Moreover, the insecticidal activity revealed that the fatality rates of 5a, 5b and 5m against aphidoidea were 85%, 83% and 87%, respectively, which indicated that the title compounds can effectively block the common carrier of plant viruses, thereby effectively reducing the TMV infection risk of tobacco. This series of synergistic effects provide key information for the research and development of antiviral agents.