Xixuan Zhao , Hao Wang , Shuting Yin , Shuai Peng , Fengjiao Li , Qian Zhang , Yongguo Liu , Baoguo Sun , Hongyu Tian , Sen Liang
{"title":"Methanesulfenylation of mercaptans and β-dicarbonyls with DMSO","authors":"Xixuan Zhao , Hao Wang , Shuting Yin , Shuai Peng , Fengjiao Li , Qian Zhang , Yongguo Liu , Baoguo Sun , Hongyu Tian , Sen Liang","doi":"10.1080/17415993.2023.2290269","DOIUrl":"10.1080/17415993.2023.2290269","url":null,"abstract":"<div><p>The methanesulfenylation of various mercaptans and β-dicarbonyls has been investigated using in-situ generated methyl methanethiosulfonate (MMTS) from DMSO, facilitated by a catalytic amount of (COCl)<sub>2</sub>. Employing the MMTS solution alongside Et<sub>3</sub>N led to the synthesis of a range of unsymmetrical disulfides with good yields. Furthermore, the introduction of [<sup>2</sup>H<sub>6</sub>]-DMSO enabled the successful preparation of various [<sup>2</sup>H<sub>3</sub>]-disulfides. In the case of most β-dicarbonyls, successful methanesulfenylation was accomplished using Et<sub>3</sub>N and DBU, resulting in favorable yields.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 3","pages":"Pages 330-345"},"PeriodicalIF":2.2,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138561903","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ruslan Khoma , Vyacheslav Baumer , Magdalina Tsapko , Nadiia Fed’ko , Sergey Vodzinskii , Yuriy Ishkov , Vladimir Gelmboldt
{"title":"Sulfite esters as products of the interaction in sulfur dioxide – alkanol – tris(hydroxymethyl)aminomethane systems","authors":"Ruslan Khoma , Vyacheslav Baumer , Magdalina Tsapko , Nadiia Fed’ko , Sergey Vodzinskii , Yuriy Ishkov , Vladimir Gelmboldt","doi":"10.1080/17415993.2024.2322126","DOIUrl":"10.1080/17415993.2024.2322126","url":null,"abstract":"<div><p>The reaction products formed in the SO<sub>2</sub> – ROH – (HOCH<sub>2</sub>)<sub>3</sub>CNH<sub>2</sub> (where R – CH<sub>3</sub>, C<sub>2</sub>H<sub>5</sub>, <em>n</em>-C<sub>3</sub>H<sub>7</sub>, <em>i</em>-C<sub>3</sub>H<sub>7</sub>, <em>n</em>-C<sub>4</sub>H<sub>9</sub> and <em>n</em>-C<sub>5</sub>H<sub>11</sub>) systems were isolated and identified as: binary salt – ammonium <em>O</em>-methylsulfite [(HOCH<sub>2</sub>)<sub>3</sub>CNH<sub>3</sub>]<sup>+</sup> [CH<sub>3</sub>OSO<sub>2</sub>]<sup>−</sup> (<strong>1</strong>); 1/1 charge transfer complex between diethyl sulfite (<strong>2</strong>) and tris(hydroxymethyl)aminomethane by S-N binding; polymorhps of zwitterionic internal salt – <em>O</em>-sulfite tris(hydroxymethyl)methylammonium (at R – <em>n</em>-C<sub>4</sub>H<sub>9</sub> and <em>n</em>-C<sub>5</sub>H<sub>11</sub>); and its solvates with <em>n</em>-propanol 1/1 (<strong>3</strong>) and isopropanol 2/1. The structures of all synthesized products were confirmed by FT-IR, Raman, <sup>1</sup>H NMR and <sup>13</sup>C NMR spectrometry, and the structure of <strong>1</strong> and <strong>3</strong> was characterized by crystal X-ray diffraction studies as well.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 3","pages":"Pages 395-407"},"PeriodicalIF":2.2,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140006745","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Konstantin F. Suzdalev , Alina V. Krachkovskaya , Ekaterina A. Lysenko , Oleg P. Demidov
{"title":"Modeling stages of domino reaction of thiopyrano[4,3-b]indole-3(5H)-thiones and dimethyl acetylenedicarboxylate: a new synthetic route to γ-carbolines with thione group","authors":"Konstantin F. Suzdalev , Alina V. Krachkovskaya , Ekaterina A. Lysenko , Oleg P. Demidov","doi":"10.1080/17415993.2023.2282667","DOIUrl":"10.1080/17415993.2023.2282667","url":null,"abstract":"<div><p>Modeling stages of the cascade reaction of thiopyrano[4,3-<em>b</em>]indole-3(5<em>H</em>)-thiones and dimethyl acetylenedicarboxylate were studied. Alkylation of thiones with alkyl halides or dimethyl sulfate affording to thiopyrano[4,3-<em>b</em>]indole-2-ium salts models the first stage of the process. The attack at the 3-position of the obtained salts by secondary amines can serve as a model for the second stage of the cascade transformation; it gives 3-benzoylindoles with thioamide-group. Reactions of thiopyrano[4,3-<em>b</em>]indole-2-ium salts with primary amines lead to a series of γ-carbolines with thione group. The action of ammonia on these salts causes dealkylation and gives thiopyrano[4,3-<em>b</em>]indole-3(5<em>H</em>)-thiones.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 3","pages":"Pages 364-377"},"PeriodicalIF":2.2,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134902303","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Nurul Fatimah Abdul Basir , Mahta Ghafarikhaligh , Mohd Rafie Johan , Nader Ghaffari Khaligh
{"title":"Mono-cyclopentyl substituted [1,3,4]thiadiazole thione tautomer: study of the spectroscopic, geometric, thermal, and biological properties","authors":"Nurul Fatimah Abdul Basir , Mahta Ghafarikhaligh , Mohd Rafie Johan , Nader Ghaffari Khaligh","doi":"10.1080/17415993.2024.2302032","DOIUrl":"10.1080/17415993.2024.2302032","url":null,"abstract":"<div><p>Regarding the importance of thiol-thione tautomer structure and the existence of hydrogen bonding in thione tautomer structure and its effect on geometric, physicochemical, and biological properties, mono-cyclopentyl-substituted bismuthiol was synthesized <em>via</em> a telescopic process in a green medium. The pure product was characterized by physical and spectroscopic techniques. The suitable crystals for single crystal study were obtained after trying different solvents and mixed solvents, and long clear needle-like crystals could be isolated from a mixture of <em>n</em>-hexane and ethyl acetate (volume ratio of 8:2). The FTIR spectra of bismuthiol, 2,5-bis-cyclopentylsulfanyl-[1,3,4]thiadiazole, and 5-cyclopentylsulfanyl-3H-[1,3,4]thiadiazole-2-thione were studied to define the characteristic wavenumbers of thiol and thione structures. A possible hyper-conjugative interaction between the S–H and π bond of C=N, the existence of C=S and C–N–H. and stability of thione structure was demonstrated for the new product, which supports our prediction of thione or thiol structure using the study of IR spectra. Furthermore, the influence of change in 1,3,4-thiadiazol ring and the presence N–H functional group of thione structure on the transition phases and thermal stability of bismuthiol, bis-cyclopentyl-substituted, and mono-cyclopentyl-substituted bismuthiol were investigated using TGA/DTA and DSC profile analysis. The SwissADME tool was employed to predict the biocheminformatic information of bismuthiol, bis- and mono-cyclopentyl-substituted bismuthiols, which displayed high potential of all 1,3,4-thiadizole derivatives in pharmaceutical and medicine areas. Finally, an <em>in vit</em>ro antibacterial activity of the mono- and bis-cyclopentyl substituted bismuthiol against the gram-negative (<em>Escherichia coli</em> ATCC 25922) and gram-positive (<em>Staphylococcus aureus</em> ATCC 25923) bacterial species was conducted by the disk diffusion method with cefazolin as a blank antibiotic. The results showed superior antibacterial efficiency of both derivatives.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 3","pages":"Pages 378-394"},"PeriodicalIF":2.2,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139421292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Sulfonic acid-supported vanillin/bis indolylmethane-functionalized Fe3O4@SiO2-propyl NPs as green, effective, and magnetically recoverable catalysts for the synthesis of imidazoquinazolines and thiazoquinazolines","authors":"Leila Zare Fekri , Zahra Mohammadi , Atefeh Alijani","doi":"10.1080/17415993.2023.2253345","DOIUrl":"10.1080/17415993.2023.2253345","url":null,"abstract":"<div><p>Sulfonic acid-supported vanillin/bis indolylmethane-functionalized Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>-Propyl NPs were prepared and characterized by FT-IR, XRD, FE-SEM, TEM, VSM, EDX, DLS, and TGA-DTG. The catalytic efficiency of the prepared nanoparticles was subsequently investigated for the effective synthesis of imidazoquinazolines via the one-pot condensation of 2-aminobenzimidazole, aryl aldehydes, and cyclohexanone or dimedone under solvent-free condition. Some thiazoquinazolines also were prepared via the multicomponent reaction of aldehydes, dimedone, and 2-aminobenzothiazol under solvent-free condition,. This avenue is really suitable because it makes a high yield of product, doesn’t take too long, doesn’t need harmful materials and solvents, its work-up is easy and the catalyst is reusable.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 2","pages":"Pages 198-216"},"PeriodicalIF":2.2,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43098268","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Photocatalytic oxidative-extractive desulfurization of dibenzothiophene under simulated solar light with MoS2-CeO2/Al2O3-SiO2 nano photocatalyst: effect of CeO2 content","authors":"Sakineh Mohammadzadeh Yengejeh , Somaiyeh Allahyari , Nader Rahemi , Sara Manuchehri , Minoo Tasbihi","doi":"10.1080/17415993.2023.2300796","DOIUrl":"10.1080/17415993.2023.2300796","url":null,"abstract":"<div><p>In this paper, a visible light-driven nanophotocatalyst of MoS<sub>2</sub> with different amounts of CeO<sub>2</sub> (0%, 8%, 16%, 24%, and 32% wt.) was impregnated on SiO<sub>2</sub>-Al2O<sub>3</sub>. The physicochemical properties of synthesized photocatalysts were investigated by XRD, FESEM, TEM, UV-Vis DRS, PL, BET-BJH, ICP-OES, EDX, and FTIR analyses. While the size of particles in all samples was in the nanoscale range, the sample with 8% wt. of CeO<sub>2</sub> indicated the narrowest particle size distribution. UV-Vis DRS and PL analyses confirmed that adding CeO<sub>2</sub> to the MoS<sub>2</sub>/SiO<sub>2</sub>-Al<sub>2</sub>O<sub>3</sub> photocatalyst increased the amount of light absorption and decreased the recombination rate of charge carriers. Among CeO<sub>2</sub>-containing samples, the sample with 8% wt. of CeO<sub>2</sub> illustrated the lowest recombination rate and the narrowest bandgap energy of 2.9 eV. The MoS<sub>2</sub>-CeO<sub>2</sub>/SiO<sub>2</sub>-Al<sub>2</sub>O<sub>3</sub> photocatalyst with 8% wt. of CeO<sub>2</sub> had the highest adsorption of DBT in dark conditions (29.93%), the highest photodegradation (96.9%) after 3 h of visible light irradiation and good stability after five consecutive runs. Meanwhile, total sulfur measurement indicated that using this sample and the extraction afterward, the model fuel has lost 96% of its sulfur content which confirms the excellent ability of acetonitrile-assisted extraction in gathering desulfurization products from the fuel.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 2","pages":"Pages 250-271"},"PeriodicalIF":2.2,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139374779","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Noha M. Hassanin , Tarik E. Ali , Somaia M. Abdel-Kariem
{"title":"Synthesis, cytotoxic evaluation, molecular docking studies and drug-likeness analysis of some novel 2-[(9-ethyl-9H-carbazol-3-yl)imino]thiazoles/thiazolidinones","authors":"Noha M. Hassanin , Tarik E. Ali , Somaia M. Abdel-Kariem","doi":"10.1080/17415993.2024.2302013","DOIUrl":"10.1080/17415993.2024.2302013","url":null,"abstract":"<div><p>A novel series of some 2-[(9-ethyl-9<em>H</em>-carbazol-3-yl)imino]thiazoles/thiazolidinones was synthesized and established by spectroscopic tools and elemental analysis. The synthetic strategy depended on cyclization of 1-(9-ethyl-9<em>H</em>-carbazol-3-yl)-3-phenylthiourea (<strong>2</strong>) with different α-halocarbonyl compounds and some carbon electrophiles under mild reaction conditions. All products were screened for their in <em>vitro</em> cytotoxic activities toward three human cancer cell lines (MCF-7, HepG-2 and HCT-116). Interestingly, the particular carbazolyl derivatives 7, 13, 14 and 16 exhibited promising cytotoxicity results against all the evaluated cell lines. Also, molecular docking studies for the highly bioactive compounds were achieved to investigate the binding mode toward (VEGFR-2-KDR) receptor. Moreover, anticancer results were validated computationally by applying SwissADME server.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 2","pages":"Pages 272-292"},"PeriodicalIF":2.2,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139459381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Taj Muhammad , Waqas Ahmad , Imtiaz Ahmad , Muhammad Yaseen
{"title":"Integrated oxidative-adsorptive desulfurization of model and real fuel oils over a Zn-impregnated hydroxyapatite-activated carbon (Zn/HA-AC) composite","authors":"Taj Muhammad , Waqas Ahmad , Imtiaz Ahmad , Muhammad Yaseen","doi":"10.1080/17415993.2023.2264439","DOIUrl":"10.1080/17415993.2023.2264439","url":null,"abstract":"<div><p>Herein, a Zn-impregnated hydroxyapatite-activated carbon (Zn/HA-AC) composite catalyst was fabricated and was, in turn, applied for the desulfurization of a model and real oil samples via the integrated adsorptive-oxidative desulfurization strategy. Activity results revealed that Zn/HA and AC (25:75) realized 76.7% dibenzothiophene (DBT) adsorptive desulfurization at 50 °C in 60 min reaction time at an adsorbent dose of 0.14 g/20 mL of feed. Zn/HA-AC(25:75) composite catalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, energy-dispersive X-ray analysis, and scanning electron microscopy analysis. In the oxidative desulfurization (ODS) combined with adsorptive desulfurization experiments, under the optimum conditions of 45 <sup>o</sup>C temperature for 60 min and a catalyst dose of 0.1 g/20 mL of feed using H<sub>2</sub>O<sub>2</sub> and HCOOH, Zn/HA-AC (25:75) achieved 93% DBT conversion. Under these optimized experimental parameters, the adsorptive desulfurization and catalytic ODS performance (% DBT conversion) of Zn/HA-AC (25:75) for real gasoline, kerosene, and diesel oil reached 18, 31 and 15%, and 31.66, 55.31 and 11.19%, respectively. Contrary to this, under the integrated catalytic-oxidative-adsorptive experiments, the desulfurization performance of Zn/HA-AC (25:75) for gasoline, kerosene, and diesel oil reached 61, 41, and 34%, respectively.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 2","pages":"Pages 217-238"},"PeriodicalIF":2.2,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135197889","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hu Yawei , Fang Tong , Ruan Miao , Zhang Yan , Zhao Ning
{"title":"Preparation and enhanced photocatalytic properties of Cu31S16/Cu9S5 heterojunction composite","authors":"Hu Yawei , Fang Tong , Ruan Miao , Zhang Yan , Zhao Ning","doi":"10.1080/17415993.2024.2316593","DOIUrl":"10.1080/17415993.2024.2316593","url":null,"abstract":"<div><p>A heterojunction photocatalytic material Cu<sub>31</sub>S<sub>16</sub>/Cu<sub>9</sub>S<sub>5</sub> was successfully synthesized through a facile solvothermal method by controlling the reaction temperature. The phase composition, morphology, absorbance and surface area were investigated by X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), UV-vis diffusion reflection and Brunauer–Emmett–Teller (BET). Transient photocurrent response and electrochemical impedance spectroscopy (EIS) were measured to support the generation and transfer of the photoinduced charge carriers. The heterojunction Cu<sub>31</sub>S<sub>16</sub>/Cu<sub>9</sub>S<sub>5</sub> showed superior separation efficiency of the photoinduced charge carriers. The photocatalytic performance of the Cu<sub>31</sub>S<sub>16</sub>/Cu<sub>9</sub>S<sub>5</sub> was evaluated through degrading high-concentration methyl orange (MO) solution under visible light. The degradation rate of MO solution increased to 94.8% in 60 min, showing the most remarkable photocatalytic ability. Moreover, a probable photocatalytic mechanism of the Cu<sub>31</sub>S<sub>16</sub>/Cu<sub>9</sub>S<sub>5</sub> was discussed.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 2","pages":"Pages 239-249"},"PeriodicalIF":2.2,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139754350","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Sulfenamide formation – chemical and biochemical reactions and their applications in cell biology","authors":"Tayebeh Amanpour , Rui Wang","doi":"10.1080/17415993.2023.2276704","DOIUrl":"10.1080/17415993.2023.2276704","url":null,"abstract":"<div><p>Sulfenamides are organosulfur compounds that contain a single bond between nitrogen and sulfur in their structures. Sulfur can react with nucleophiles to yield new compounds. The compounds having nitrogen–sulfur bonds are used in polymers for a variety of purposes, including medicines, agrochemicals, veterinary medications, and environmental studies. This review will examine several chemical reactions that lead to sulfenamide production as well as how they are used in cell biology and biochemical applications.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"45 2","pages":"Pages 293-312"},"PeriodicalIF":2.2,"publicationDate":"2024-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135271262","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}