Carbon Disulfide Research Articles

Computational Studies and Antimicrobial Activity of 1-(benzo[d]oxazol-2- yl)-3,5-diphenylformazan Derivatives.

Due to the biological importance of the benzoxazole derivatives, some 1- (benzo[d]oxazol-2-yl)-3,5-diphenyl-formazans 4a-f were synthesized and screened for in-silico studies and in-vitro antibacterial activity. The benzo[d]oxazole-2-thiol (1) was prepared by reacting with 2-aminophenol and carbon disulfide in the presence of alcoholic potassium hydroxide. Then 2-hydrazinylbenzo[d] oxazole (2) was synthesized from the reaction of compound 1 with hydrazine hydrate in the presence of alcohol. Compound 2 was reacted with aromatic aldehydes to give Schiff base, 2-(2- benzylidene-hydrazinyl)benzo[d]oxazole derivatives 3a-f. The title compounds, formazan derivatives 4a-f, were prepared by a reaction of benzene diazonium chloride. All compounds were confirmed by their physical data, FTIR, 1H-NMR, and 13CNMR spectral data. All the prepared title compounds were screened for in-silico studies and in-vitro antibacterial activity on various microbial strains. Molecular docking against the 4URO receptor demonstrated that molecule 4c showed a maximum dock score of (-) 8.0 kcal/mol. MD simulation data reflected the stable ligand-receptor interaction. As per MM/PBSA analysis, the maximum free binding energy of (-) 58.831 kJ/mol was exhibited by 4c. DFT calculation data confirmed that most of the molecules were soft molecules with electrophilic nature. The synthesized molecules were validated using molecular docking, MD simulation, MMPBSA analysis, and DFT calculation. Among all the molecules, 4c showed maximum activity. The activity profile of the synthesized molecules against tested micro-organisms was found to be 4c>4b>4a>4e>4f>4d.

Synthesis and antitumor evaluation of glycyrrhetinic acid-dithiocarbamate hybrids.

Glycyrrhetinic acid (GA) is a naturally occurring triterpene compound. The aim of this study was to employ the pharmacophore hybrid strategy to merge GA with various dithiocarbamates and obtain novel compounds with better antitumor activities. We present a two-step synthetic protocol wherein the GA derivative underwent reaction with carbon disulfide and various secondary amines in a one-pot manner under mild conditions, facilitating the preparation of a series of structurally novel GA-dithiocarbamate derivatives. Bioassay screening revealed that the representative compound 3c demonstrated the capacity to reduce the mitochondrial membrane potential in Hep3B and Huh-7 cells, induce nuclear apoptosis, inhibit invasion and migration, and prompt both early and late apoptosis. Furthermore, our research findings indicated that this apoptotic phenomenon may be associated with the expression of Bcl-2, Bax, Bak, PARP, and cleaved-PARP proteins. Utilizing network pharmacology for predicting core targets and signaling pathways of compound 3c for hepatocellular carcinoma (HCC) treatment involved employing molecular docking models to demonstrate high affinity between compound and target protein. In conjunction with Western blot analysis, compound 3c may impact HCC through the PI3K-AKT-mTOR pathway.

Design, Synthesis, Antibacterial, and Antifungal Evaluation of a New Series of Quinazoline - Thiazole and/or Quinazoline - Triazole Hybrids as Bioactive Heterocycles.

Herein, a one-pot reaction between cyclohexanone, thiourea, and 2,5-dimethoxybenzaldehyde allowed to prepare hexahydroquinazoline-2(1H)-thione4 firstly, which followed by reacting with hydrazine hydrate to produce the corresponding 2-hydrazinylhexahydroquinazoline 6. Interesting analogs of thiazolo[3,2-a]quinazoline 713 where obtained when hexahydroquinazoline-2(1H)-thione 4 reacted with 1,2-dibromoethane, chloroacetyl chloride, bromoacetic acid, bromoacetic acid/4-chlorobenzaldehyde, 2-bromopropionic acid, ethyl bromo cyanoacetate, and/or bromomalononitrile; respectively. While triazolo[4,3-a] quinazoline 14-16 were created when 2-hydrazinylhexahydroquinazoline 6 reacted with triethyl orthoformate, acetic anhydride, and carbon disulfide respectively. Numerous spectroscopy tests, including FT-IR, NMR (1H &13 C), and MS spectrum, proved all the newly produced analogs. Additionally, the new analogs were examined for their antibacterial and antifungal properties against Escherichia coli, Staphylococcus aureus, and Candida albicans. It was discovered that triazolo[4,3-a] quinazoline analogs 14-16 have superior bacterial and fungal activity when compared to the corresponding conventional doses of Streptomycin andGriseofulvin. Towards Candida albicans; compounds 14, 15, and 16 increase activity with 1.14 %, 1.15 %, and 1.21 %, respectively more than griseofulvin.While, for Staphylococcus aureus; compounds 14, 15, and 16 increase activity with 1.5 %, 1.5 %, and 1.7 %, respectively more than streptomycin. Morever, for Escherichia coli; compounds 14, 15, and 16 increase activity with 1.19 %, 1.21 %, and 1.22 %, respectively more than streptomycin. Finally, structure activity relationships show that quinazoline derivatives exhibit higher activity when fused to pyrazole ring 14-16 as compared when fused thiophene ring 7-13.

Comprehensive Assessment of Carbon Disulfide Exposure in Laboratories—Air and Biological Monitoring Approaches

Carbon disulfide (CS2) is a highly toxic and flammable solvent extensively used in chemical processes and laboratory analyses. This review examines both air and biological monitoring methods for assessing the exposure of laboratory workers to CS2. Emphasis is placed on the measurement of airborne CS2 concentrations and the monitoring of 2-thiothiazolidine-4-carboxylic acid (TTCA) in urine, a key biomarker of exposure. By analysing case studies and practical applications, the paper outlines the effectiveness and limitations of current monitoring techniques. Additionally, the review addresses key challenges such as CS2 volatility, dietary influence on biomarker levels, and the sufficiency of protective measures, including nitrile gloves. It also proposes best practices to mitigate exposure, such as improved ventilation, the use of polyvinyl alcohol gloves, and the substitution of CS2 with less hazardous solvents. This comprehensive review underscores the need for continuous vigilance in managing chemical exposure and offers insights into how laboratories can better protect their workers by integrating air and biological monitoring strategies.

Synthesis of 1,3-thiazolidine-2-thiones using CS2 and epoxy amines

An efficient method for the synthesis of 5-(hydoxymethyl)-1,3-thiazolidine-2-thiones is developed via the reaction of carbon disulfide with N-alkyl(aryl) epoxy amines. The reaction proceeds via intramolecular epoxide ring opening with in situ prepared dithiocarbamic acid. The products were obtained in good to high yields.

Diamidocarbene-derived palladium and nickel-sulfur clusters.

Novel palladium and nickel-sulfur clusters were synthesized using a diamidocarbene-derived carbon disulfide ligand. Structural characterization revealed a tetranuclear metal-sulfur cluster geometry with each metal center exhibiting square-planar coordination. The ligand was redox-active, accommodating oxidation states ranging from 0 to -2.

Synthesis of new triazole derivatives and their potential applications for removal of heavy metals from aqueous solution and antibacterial activities.

In this paper, triazole derivatives were prepared by a three-step mild reaction using carbon disulfide as starting material. In face of microbial threats, we found that compound 3-cyclopropyl-[1,2,4]triazolo [3,4-b][1,3,4]thiadiazole-6-thiol (C2) has good antibacterial activity, inhibition and clearance ability against biofilms, low hemolytic activity and toxicity, good anti-inflammatory activity. At the same time, we found that B and C series compounds have good metal ion scavenging ability, with removal rates of C series ranging from 47% to 67% and B series ranging from 67% to 87%.

Effect of eucalyptus globulus pulp properties on fock reactivity

AbstractDissolving-grade pulps serve as the primary material for producing regenerated cellulose fibers, and their utilization is steadily increasing. Despite extensive research efforts, it remains necessary to deepen our understanding of the inherent factors that impact pulp reactivity apart from the well-known degree of polymerization. The Fock reactivity test is commonly used to quantify the reactivity of cellulose pulp by measuring the percentage of cellulose that reacts with carbon disulfide. Dissolving pulps typically require a reactivity of over 90%. Hemicellulose content, intrinsic viscosity, cell wall porosity, crystallinity, and accessible area of four different pulps were characterized and distinct treatments were employed to try to separate the effect of different pulp properties and assess their effect on Fock reactivity. Hemicelluloses removal by xylanase and cold caustic treatments (86% removal) increased the Fock reactivity by 30%, from 55.7% to 71.3%. Assuming the hemicelluloses are fully accessible by the CS2, cellulose reactivity increased from 35.6% to 69.5%,but at the expense of an intrinsic viscosity decrease from 990 cm3/g to 689 cm3/g. This unexpected intrinsic viscosity decrease can be due to the cellulose de-shielding effect provoked by hemicellulose removal and some cellulose degradation during cold caustic extraction. Vibrational impact ball-milling applied on a pulp with 5% hemicellulose content notably boosted Fock reactivity by 56%, from 54% to 84.5%, but two pulp properties, intrinsic viscosity, and crystallinity, decreased concurrently due to the high-energy treatment. This phenomenon complicates identifying a direct correlation between heightened reactivity and a single parameter. To address this, endoglucanase treatment was used to separate intrinsic viscosity from crystallinity, clarifying their contributions to changes in Fock reactivity. Unfortunately, the effect of a given physical or bio/chemical pulp treatment affects more than one pulp property, always including the cellulose degree of polymerization, which has made it difficult to isolate the pulp properties that affect Fock reactivity. Several processes have been tested to obtain pulp with dissolving potential.

Exploring the Reactivity of Electrophilic Organic Carbonates and Thiocarbonates as Vehicles to Convert Hydrosulfide into COS and CS2.

Hydrogen sulfide (H2S) and other reactive sulfur species are important small molecules with biological significance. In addition to common reactive sulfur species like H2S, polysulfides, and persulfides, both carbonyl sulfide (COS) and carbon disulfide (CS2) have been postulated to be potential sources of reduced sulfur. To better understand this possible connection, we demonstrate that H2S can be converted to COS and CS2 by reaction with simple organic carbonate and thiocarbonate electrophiles, respectively.

Extensive investigation of seasonal and spatial fluctuations of BTEX in an industrial city with a health risk assessment

There are many pollutants in the air that can be harmful to human health. Their impact varies based on factors such as the kind of pollutant, duration of exposure, and concentration levels. Volatile organic compounds are particularly significant carcinogens among the various pollutants present in the air. Consequently, people who are exposed to these harmful airborne pollutants suffer permanent consequences. This study examines the properties of BTEX compounds—benzene, toluene, ethylbenzene, and xylene—as well as their sources and risk assessments throughout a one-year period from March 21, 2019, to March 20, 2020, in Karaj, Iran’s largest industrialized city. First, utilizing a geographical information system that covered the entire city, 17 locations within Karaj were chosen for this purpose. Then, samplings were carried out in the spring, summer, autumn, and winter months with the NIOSH 1501 method. During the research period, 68 samples of BTEX compounds were collected. The adsorption of these contaminants on the activated carbon adsorbents was performed using an environmental sampling pump with a flow rate of 0.2 L/min for 1 h. The samples were subsequently prepared using a carbon disulfide solution and injected into a GC-FID for analysis. In this research, the average annual concentration of BTEX compounds in the air of Karaj city was obtained at 33.01 µg/m3. Autumn and spring had the highest and lowest average concentrations of BTEX compounds, respectively. In addition, sites 5 and 8 had the highest average annual concentrations of these pollutants. The sourcing conducted in this study showed that transportation and fuel consumption, as well as industries, were the primary sources of pollution in the city. In addition, the excess lifetime cancer risk was higher than the guideline value in some sites and lower in others. Furthermore, the Hazard Quotients were lower than 1, but in general, the citizens of Karaj were at serious risk from exposure to this group of pollutants.

Synthesis of New Heterocyclic Derivatives from 4-(3, 5-Dimethyl-1-phenyl-1H-pyrazol-4-ylazo)- benzoic acid

In this work pyrazolin derivatives were prepared from the diazonium chloride salt of 4-aminobenzoic acid. Azo compounds were prepared from the reaction of an ethanolic solution of sodium acetate and calculated amount of active methylene compound namely, acetyl acetone to obtain the corresponding hydrazono derivative (1). Cyclocondensation reaction of compounds (1) with hydrazine hydrate and phenyl hydrazine in boiling ethanol affording the corresponding pyrazoline-5-one derivatives of 4-aminobenzoic acid (2,3). Then compound (3) was reacted with thionyl chloride to give the corresponding acid chloride derivative(4), followed by conversion into the corresponding acid hydrazide derivative (5) carboxylic acid thiosemicarbazide (11), esters (14,15), thioesters (16,17) and amides (18,19), when treated hydrazine hydrate, thiosemicarbazide, alcohols, alkylthiol and secondary amines in dry refluxing benzene; respectively. Schiff's bases (6-8) were prepared by refluxing of compound (5) with different aldehydes and ketons, then two compounds from the Schiff's bases were cyclized with ?-mercapto acetic acid to give (9 and 10). Furthermore, 1,2,4-triazole derivative (12) have been also prepared by refluxing thiosemicarbazide derivative with sodium hydroxide solution (4%) followed acidification of the result using (10%)hydrolic acid. Moreover, a thiadiazole derivative (13) has been prepared by treatment of thiosemicarbazide derivative with concentrated sulfuric acid as cyclyzing agent. Finally, oxadiazole derivative (20) has prepared by condensation of its acid hydrazide derivative with carbon disulfide in basic medium.

A green and efficient synthesis of alkyl 2-((5-hydroxy-1H-pyrazole-4-carbonothioyl)thio)acetates via a one-pot, solvent-free reaction

A green and efficient synthesis of alkyl 2-((5-hydroxy-1H-pyrazole-4-carbonothioyl)thio)acetates is described. The method involves a one-pot, solvent-free reaction of pyrazolone derivatives, carbon disulfide, and alkyl bromoacetates in the presence of triethylamine. The crude products were readily purified by simple water washing followed by recrystallization from diethyl ether. The structures of the synthesized pyrazole-4-carbonothioyl-thio-acetate derivatives were confirmed by IR, 1H NMR, 13C NMR, and mass spectrometry.

Cascade Synthesis in Water: Michael Addition/Hemiketalization/Retro-Claisen Fragmentation Catalyzed by CatAnionic Vesicular Nanoreactor from Dithiocarbamate.

N,N-didodecylammonium N,N-didodecyldithiocarbamate (AmDTC-C12C12) underwent self-assembly to form a CatAnionic vesicular nanoreactor in water. AmDTC-C12C12 can be readily prepared by condensation between N,N-didodecylamine and carbon disulfide. Previously, the cascade Michael addition/hemiketalization/retro-Claisen fragmentation was reported, but it required petroleum-based organic solvents as reaction media. Herein, the application of AmDTC-C12C12 in aqueous cascade synthesis is investigated. Initially, we explored the catalytic activity of AmDTC-C12C12 (10 mol%) in the synthesis of 4H-chromene through a double-cascade Michael addition/hemiketalization. The reaction occurred in water at room temperature using 2-hydroxy-trans-b-nitrostyrene as Michael acceptor and acetylacetone as Michael donor yielding 2-chromanol intermediates. Subsequent acidic dehydration of 2-chromanols produced 4H-chromenes with moderate yields (34-60%) and phenyl acetates of g-nitro ketone as co-products (13-27%), deriving from retro-Claisen fragmentation. Surprisingly, using Michael donors with aromatic moieties on the 1,3-dicarbonyls resulted in spontaneous triple-cascade Michael addition/hemiketalization/retro-Claisen fragmentation in water, without the need for acidic dehydration. The g-nitro ketones were obtained as sole products, with no detection of 4H-chromenes, in moderate to high yields (31-84%) for symmetrical 1,3-dicarbonyl containing two aromatic groups. Unsymmetrical 1,3-dicarbonyl bearing aromatic/aliphatic or aromatic/aromatic groups afforded g-nitro ketones in favorable yields (73-97%).

Synthesis of Dithiocarbamate‐Functionalized Aliphatic Sulfonyl Fluoride via a One‐Pot Three‐Component Reaction

AbstractAn eco‐friendly and efficient method was developed for synthesizing a novel class of aliphatic sulfonyl fluorides in a catalyst‐free one‐pot reaction. The new approach offers a streamlined synthesis for N‐(Substituted)‐2‐(fluorosulfonyl) ethyl carbamodithioates by combining amines, carbon disulfide, with ethenesulfonyl fluoride. The synthesized compounds were obtained in good yields under mild conditions, making this reaction a valuable tool for exploring new chemical transformations.

Reactivity of (3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone Toward Some Nucleophiles for Preparing Promising Agents with Antimicrobial and Antioxidant Activities

Abstract(3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone 2 was prepared from the reaction of 3‐(4‐fluorophenyl)‐1‐(naphthalen‐2‐yl)prop‐2‐en‐1‐one (1) with hydrogen peroxide and reacted with different nucleophiles such as hydrazine hydrate, phenyl hydrazine, thiosemicarbazide to give 4‐hydroxy‐1H‐pyrazole derivatives 3a,b‐4. Also, compound 2 was treated with hydroxylamine hydrochloride to give the substituted 2,3‐dihydroisoxazole 5. Similarly, compound 2 was treated with carbon disulfide, phenyl isothiocyanate, and phenyl isocyanate to give the corresponding compounds 6–8. Various spectroscopic techniques and elemental analysis were used to determine the molecular structures of the new derivatives. All the new analogs were screened against five human pathogenic microbial strains: Escherichia coli and Pseudomonas aeruginosa as Gram‐negative bacteria, Bacillus subtilis and Staphylococcus aureus as Gram‐positive bacteria and the yeast Candida albicans using agar diffusion method. Compound 4 exhibited moderate antimicrobial activity against all the tested microorganisms compared to positive control ciprofloxacin and fluconazole. On the other hand, the free radical scavenging activity of the new compounds using DPPH assay protocol revealed that most of the compounds have a weak reducing activity. Moreover, compounds 4 and 8 were docked against 1KZN protein (DNA gyrase), 3FYV and 5V5Z showing the ability to interact with key amino acid residues and the potential to act as inhibitors.

Composition of Gases in the Interporous Space of Technogenic Bodies

Abstract —We present results of studies of inclusions in secondary sulfates (antlerite and a mixture of copiapite and coquimbite) and arsenates (erythrite and picropharmacolite) formed on the surface of technogenic bodies, such as stored waste from the enrichment of sulfide (Belovo and Ursk waste heaps) and arsenide (disposal maps of the Tuvakobalt plant) ores. A wide range of components were identified in the gas–liquid inclusions, the main ones being water and carbon dioxide. Hydrocarbons, oxygen-containing organic compounds, and nitrogen- and sulfur-containing gases were found in smaller but measurable amounts. Arsine H3As was also detected in inclusions in picropharmacolite (calcium and magnesium arsenate–arsenite). The gas–liquid inclusions in secondary minerals reflect the composition of the interporous space in the waste body, filled with particular atmospheric gases entering the body in free form and with seasonal precipitation. The combination of in situ generated and penetrating gases determines the diversity of inorganic and biotic interactions in technogenic bodies. The presence of hydrocarbons and oxygen-containing organic compounds is, most likely, associated with bacterial transformations of organic matter (residual vegetation, wood, microalgae, and fungi). At the same time, carbon disulfide and sulfur dioxide are indicators of active inorganic reactions of decomposition of the sulfide matrix.

N-Heterocyclic Carbene-Derived Carbon Disulfide Radical Ligands for Palladium Diradicals.

N-heterocyclic carbenes (NHCs) are recognized for their ability to stabilize various main group radicals; however, NHC-derived, sulfur-based radicals remain rare. In this study, we successfully synthesized and characterized a series of palladium diradical complexes that featured new sulfur-based radical ligands from NHC-carbon disulfide adducts. Spectroscopic and computational characterizations of the palladium complexes confirmed the open-shell singlet ground state, which resulted from the antiferromagnetic coupling of two unpaired electrons on each ligand. Proton nuclear magnetic resonance relaxometry was used to experimentally confirm the presence of these unpaired electrons. Moreover, the redox behavior of the complexes was localized on the ligand center, confirming the redox activity of the ligands. The discovery of this sulfur-based, redox-active radical ligand underscores the versatility and significance of NHC-derived radicals, thereby expanding the repertoire of radical ligands and opening new avenues for advanced material and catalytic systems.

Synthesis of sodium 1,3-propanebis(dithiocarbamate) and study of its flotation properties

Development and selection of a suitable reagent for efficient flotation is of great importance for ore beneficiation processes. Dithiocarbamates represent a class of organic compounds that are widely used as reagent-collectors in ore flotation. In this work, we conducted an analytical review of the methods currently used for obtaining this class of compounds and established the main method for obtaining dithiocarbamate salts to be the interaction of primary or secondary amines with carbon disulfide (CS2) in the presence of potassium or sodium hydroxide. The aim of the reviewed work was to synthesize sodium 1,3-propanebis(dithiocarbamate), as well as to study its flotation properties in the beneficiation of gold-bearing sulfide ores. A simple and effective method for sodium 1,3-propanebis(dithiocarbamate) synthesizing was proposed. Its structure was confirmed using physicochemical methods (infrared spectroscopy, 1H, 13C nuclear magnetic resonance spectroscopy). A set of studies found that the combined use of potassium butyl xanthate and sodium dialkyl dithiophosphate (BTF-1552) with sodium 1,3-propanebis(dithiocarbamate) led an increase in the efficiency of extraction of the target component of up to 81.63%, as well as an increase in its content in the concentrate of up to 7 g/t. In addition, the combination of sodium 1,3-propanebis(dithiocarbamate) with potassium butyl xanthate was shown to enable an extraction efficiency of 80.51%, as well as a valuable component content in the concentrate of up to 6.5 g/t with a low gold content in flotation tailings of 0.07 g/t. The proposed synthesis method and the results of flotation tests of gold-bearing ores are of interest for further research in the field of organic synthesis and practical application.

Abiotic Production of Dimethyl Sulfide, Carbonyl Sulfide, and Other Organosulfur Gases via Photochemistry: Implications for Biosignatures and Metabolic Potential

Among the atmospheric gases that have been proposed as possible biosignatures in exoplanetary atmospheres, organosulfur gases are currently considered one of the more robust indicators of extant life. These gases include dimethyl sulfide (DMS; CH3SCH3), carbonyl sulfide (OCS), and carbon disulfide (CS2), which are predominantly secondary metabolic products of living organisms on Earth. Here we present results that challenge this interpretation and provide constraints on the robustness of organosulfur gases as biosignatures. Through laboratory photochemical experiments, we show the abiotic production of organosulfur gases, including DMS, OCS, methane thiol (CH3SH), ethane thiol (C2H5SH), CS2, and ethyl methyl sulfide (CH3CH2SCH3) via photochemistry in analog atmospheres. Gas-phase products of H2S/CH4/N2 haze photochemistry, with or without CO2, were collected and analyzed using gas chromatography equipped with sulfur chemiluminescence detection. Depending on the starting conditions, we estimate that DMS, OCS, CH3SH, CH3CH2SH, CS2, and CH3CH2SCH3 are produced in mixing ratios >10−1 ppmv. We further demonstrate that as the mixing ratio of CO2 increases, so does the relative importance of OCS compared to DMS. Although our results constrain the robustness of common organosulfur gases as biosignatures, the presence of these compounds may serve as an indicator of metabolic potential on exoplanets.

Molecular dynamics-based targeted adsorption of hazardous substances from rubberized asphalt VOCs by UiO-67

The interplay among UiO-67 and rubberized-asphalt components has been examined according to its molecular scale. The adhesion kinetics of UiO-67 to VOCs molecules in asphalt was modeled. The binding energy, radial distribution function (RDF), solubility parameters (SP), mean square displacement (MSD) and other parameters among UiO-67 to rubberized-asphalt components were evaluated in depth. The Sorption module was simulated the adsorption behavior of UiO-67 on 12 malodorous gases and 5 primary carcinogens. In combination with GC-MS results, the conjugative bonds and target attachment mechanisms for UiO-67 with VOCs were clarified. It was indicated that the binding energy among UiO-67 to the components were all negative. The radial distribution of asphalt was characterized as proximally ordered and remotely disordered. The ΔSP was less than 1.6, which was indicated that UiO-67 could be compatible with asphalt. The overall inhibition effect of UiO-67 on a group of carcinogens was exceeded 70 %. The presence of conjugation effect was allowed the adsorption sites of vinyl chloride and 1,3 butadiene to occur at high densities within the benzenoid. The concentration reduction of UiO-67 for hydrogen sulfide, carbon disulfide, and dimethyl sulfide was more than 80 %. The higher polarity was predisposed substances such as hydrogen sulfide and isobutanol to interact with the non-benzene ring region of UiO-67.