Virág Kiss , Ádám Kecskeméti , Bence Marcell Hülvely , Péter Tarczali Sarudi , Luca Judit Csépes-Ruzicska , Fruzsina Mercs , Ágnes Tóth , István Fábián , Katalin Ősz
{"title":"Reductive dehalogenation and formation of sulfonated quinones in the aqueous reactions between various chloro-1,4-benzoquinones and sulfur(IV)","authors":"Virág Kiss , Ádám Kecskeméti , Bence Marcell Hülvely , Péter Tarczali Sarudi , Luca Judit Csépes-Ruzicska , Fruzsina Mercs , Ágnes Tóth , István Fábián , Katalin Ősz","doi":"10.1080/17415993.2023.2214267","DOIUrl":"10.1080/17415993.2023.2214267","url":null,"abstract":"<div><div>In this paper, the kinetic study of the reaction between substituted 1,4-benzoquinones (RBQs) and Na<sub>2</sub>SO<sub>3</sub> (S(IV)) is presented in aqueous solutions at different pH values and reagent concentrations. The stoichiometry of the reaction is 1:2 RBQs:S(IV) and one equivalent of chloride ion was also detected as a product when using mono- (2-CBQ) or dichloro-benzoquinones (2,5-DCBQ; 2,6-DCBQ) as reactants. This shows that reductive dehalogenation occurs instead of simple reduction to the corresponding substituted 1,4-hydroquinones (RBQHs) and quinone bisulfites are formed, analogously to the addition of bisulfite ion to carbonyl compounds. Various sulfonated quinones have been identified as products by electrospray mass spectrometry. Kinetic traces at different wavelengths were obtained by the stopped-flow technique with spectrophotometric detection, a kinetic fitting program (ZiTa) was used to fit a multi-step model to the data. A detailed mathematical evaluation of the reaction scheme was carried out under non-pseudo-first order conditions showing that our model can be fitted with a double exponential function even when none of the reagents are in large excess.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 6","pages":"Pages 646-665"},"PeriodicalIF":2.1,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49657067","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Deep eutectic solvents with ultrasonic energy as an environmentally benign and green approach for the synthesis of bisthioglycolic acid derivatives","authors":"Gobind Kumar , Parvesh Singh , Gaurav Bhargava , Baljinder Singh Gill , Jaspreet Kaur Rajput , Rupesh Kumar","doi":"10.1080/17415993.2023.2242994","DOIUrl":"10.1080/17415993.2023.2242994","url":null,"abstract":"<div><div>The present methodology explored the effectiveness and versatility of deep eutectic solvent with ultrasonic energy as an eco-friendly protocol for the synthesis of bisthioglycolic acid derivatives. Bisthioglycolic moiety holds its role as a potent scaffold in sulfur-containing drugs. The presented strategy offers significant advantages such as green catalyst as well as solvent, excellent yield, short reaction time, and simple reaction workup. This methodology shows a wide range of substrate scope that contain both electron-donating as well as electron-withdrawing groups.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 6","pages":"Pages 751-761"},"PeriodicalIF":2.1,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47088647","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":"Iodine-mediated oxidative N–S bond formation: a facile one-pot synthetic approach to 1,2,4-benzothiadiazine 1,1-dioxides under transition metal-free conditions","authors":"Sümeyye Buran Uğur , Şengül Dilem Doğan","doi":"10.1080/17415993.2022.2164693","DOIUrl":"10.1080/17415993.2022.2164693","url":null,"abstract":"<div><p>Benzothiadiazine 1,1-dioxide derivatives are widely used because of their diverse biological activities and medicinal prospects. In this study, iodine-oxone mediated oxidative N–S bond formation reaction was described. This new and transition-metal-free approach allows for the convenient synthesis of a variety of 1,2,4-benzothiadiazine 1,1-dioxides from readily available urea derivatives under very mild conditions without using expensive reagents and catalysts. Further, this protocol allows for the development of a library of key building blocks with potential medical applications.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 354-360"},"PeriodicalIF":2.2,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47262665","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}
Sodeeq Aderotimi Salami , Vincent J. Smith , Rui W.M. Krause
{"title":"Aqueous microwave assisted novel synthesis of isothiocyanates by amine catalyzed thionation of isocyanides with Lawesson's reagent","authors":"Sodeeq Aderotimi Salami , Vincent J. Smith , Rui W.M. Krause","doi":"10.1080/17415993.2022.2164196","DOIUrl":"10.1080/17415993.2022.2164196","url":null,"abstract":"<div><p>A green and sustainable chemistry approach for organic synthesis is described here, which involves microwave exposure of reactants in the presence of water. A general, practical, and highly efficient protocol for the preparation of a broad range of functionalized isothiocyanates has been developed from their corresponding isocyanides using Lawesson's reagent and catalytic amount of amine bases, particularly triethylamine under microwave irradiation conditions. As opposed to established approaches that employ toxic or volatile electrophilic liquids (thiophosgene, its derivatives, or CS<sub>2</sub>). In addition, these compounds were synthesized also by conventional heating procedures for comparison. Comparison between conventional and microwave-assisted synthesis was carried out by comparing total reaction time and percentage yield. The results suggest that microwave-assisted syntheses lead to higher yields within very short reaction times.</p><p>From isocyanides to isothiocyanates using Lawesson’s reagent in the presence of triethylamine under conventional and microwave heating conditions.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 269-281"},"PeriodicalIF":2.2,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49037679","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":"Property and reactivity of polyselenides and polysulfides: a quantum chemistry study","authors":"Hui-Chu Pi , Ching-Han Hu","doi":"10.1080/17415993.2022.2152284","DOIUrl":"10.1080/17415993.2022.2152284","url":null,"abstract":"<div><p>High-level ab initio and density functional theory were applied to investigate property and reactivity of polyselenides and polysulfides. With CH<sub>3</sub>X<sub>n</sub>H (X = S or Se) we found that the deprotonation energy (and p<em>K<sub>a</sub></em>) of CH<sub>3</sub>Se<sub>n</sub>H, ionization potential (IP) of, and CH<sub>3</sub>Se<sub>n</sub>−H bond dissociation energy (BDE) are lower than those of their sulfur counterparts. For <em>n</em> = 2, IPs and X−H BDEs are exceptionally small. The relative nucleophilicity of <span><math><mrow><mtext>C</mtext></mrow><mrow><msub><mrow><mtext>H</mtext></mrow><mn>3</mn></msub></mrow><msubsup><mrow><mtext>X</mtext></mrow><mi>n</mi><mo>−</mo></msubsup></math></span> vary with substrates. However, CH<sub>3</sub>Se<sub>n</sub>H are more nucleophilic than CH<sub>3</sub>S<sub>n</sub>H due to their due to their lower deprotonation energy. The nucleophilicity of selenolates versus thiolates are related to the chemical nature. Selenium is more electrophilic than sulfur.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 304-319"},"PeriodicalIF":2.2,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44388986","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}
Ashraf A. Aly , Elham M. Abdallah , Salwa A. Ahmed , Mohamed K. Awad , Mai M. Rabee , Sara M. Mostafa , Stefan Bräse
{"title":"Metal complexes of new thiocarbohydrazones of Cu(I), Co(II), and Ni(II); identification by NMR, IR, mass, UV spectra, and DFT calculations","authors":"Ashraf A. Aly , Elham M. Abdallah , Salwa A. Ahmed , Mohamed K. Awad , Mai M. Rabee , Sara M. Mostafa , Stefan Bräse","doi":"10.1080/17415993.2022.2145846","DOIUrl":"10.1080/17415993.2022.2145846","url":null,"abstract":"<div><p>Substituted thiocarbohydrazones were synthesized to study their complexation capability towards Cu(I), Co(II), and Ni(II) salts. The Cu(I) complexes showed ligation of one mole of Cu(I)Br to one of the synthesized ligands to form a cationic–anionic metal complex. Co(II) and Ni(II) complexes were determined due to the chelating of equal equivalents of both ligands and metal salts to form monodentate metal dihalogenated complexes. Metal complexes were characterized by mass spectrometry, IR, NMR, UV spectra, and elemental analyses. Theoretical calculations were performed using density functional theory (DFT) at the B3LYP level with 6–31 + G(d) and LANL2DZ basis sets to access reliable results to the experimental values. The calculations were performed to obtain the optimized molecular geometry, charge density distribution, extent of distortion from regular geometry, the HOMO (highest occupied molecular orbital), the LUMO (lowest unoccupied molecular orbital), the molecular electrostatic potential (MEP), reactivity index (ΔE), dipole moment (D), global hardness (η), softness (σ), electrophilicity index (ω), and chemical potential. The calculations confirmed that the investigated complexes have a reliable geometry, agreeing with the experimental observation.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 282-303"},"PeriodicalIF":2.2,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48303097","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}
Micheal K. Farh , Ikrame Louzi , Hassan Abul-Futouh , Helmar Görls , Norman Häfner , Ingo B. Runnebaum , Wolfgang Weigand
{"title":"Platinum(II) and palladium(II) complexes mediated by β-hydroxy-dithioesters ferrocenyl derivatives: synthesis, characterization and antiproliferative activity","authors":"Micheal K. Farh , Ikrame Louzi , Hassan Abul-Futouh , Helmar Görls , Norman Häfner , Ingo B. Runnebaum , Wolfgang Weigand","doi":"10.1080/17415993.2022.2152285","DOIUrl":"10.1080/17415993.2022.2152285","url":null,"abstract":"<div><p>Ferrocene and its derivatives compounds have shown a significant role in medicinal organometallic chemistry as an antiparasitic or antibacterial. Therefore, we herein report on the utilization of dithioesters ferrocenyl derivatives as proligands for the synthesis of heteroleptic platinum(II) and homoleptic palladium(II) complexes bearing a conserved <em>O,S</em> binding moiety. The resulting complexes [Pt(L1)(DMSO)Cl] (<strong>1</strong>), [Pt(L2)(DMSO)Cl] (<strong>2</strong>), [Pt(L3)(DMSO)Cl] (<strong>3</strong>), [Pd(L1)<sub>2</sub>] (<strong>4</strong>), [Pd(L2)<sub>2</sub>] (<strong>5</strong>), and [Pd(L3)<sub>2</sub>] (<strong>6</strong>), in which HL1 = methyl 3-hydroxy-3-ferroceneprop-2-enedithioate, HL2 = ethyl 3-hydroxy-3-ferroceneprop-2-enedithioate and HL3 = propyl 3-hydroxy-3-ferroceneprop-2-enedithioate, were fully characterized employing a variety of analytical techniques (NMR spectroscopy, elemental analysis, and mass spectrometry and X-ray structure determination of complexes <strong>2</strong> and <strong>6</strong>). Cytotoxicity assays of the synthesized ligands as well as the Pt/Pd metal complexes showed low toxicity towards ovarian cancer cells, but the compounds are not affected by cisplatin resistance mechanisms. Pt(II) complexes exhibited the highest activity, and the alkyl substituent strongly influenced the activity of these complexes and the free ligands. The cytotoxic activity increases with the length of the alkyl chain with <strong>3</strong> exhibiting a mean IC<sub>50</sub> of 56 µM.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 320-335"},"PeriodicalIF":2.2,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48808203","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":"Synthesis of novel adamantane-containing dihydropyrimidines utilizing Biginelli condensation reaction","authors":"Mina Abkar Aras , Adeleh Moshtaghi Zonouz","doi":"10.1080/17415993.2023.2166348","DOIUrl":"10.1080/17415993.2023.2166348","url":null,"abstract":"<div><p>Novel dihydropyrimidines incorporating an adamantane motif have been synthesized using a three-component Biginelli reaction of adamantane-containing β-keto amide N-1-adamantyl acetoacetamide as active methylene compound, thiourea, and aromatic aldehydes in more convenient condition and high yields. The structures of the synthesized compounds were confirmed by spectral data.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 361-376"},"PeriodicalIF":2.2,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43099745","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}
Mustafa M. Kadhim , Evan Abdulkareem Mahmood , Mohammad Reza Poor Heravi , Somayeh Soleimani-Amiri , Abdol Ghaffar Ebadi , Esmail Vessally
{"title":"The synthesis of biologically active 1-sulfonyl-1, 2, 3-triazoles from sulfonyl azides and alkynes: a focus review","authors":"Mustafa M. Kadhim , Evan Abdulkareem Mahmood , Mohammad Reza Poor Heravi , Somayeh Soleimani-Amiri , Abdol Ghaffar Ebadi , Esmail Vessally","doi":"10.1080/17415993.2022.2149266","DOIUrl":"10.1080/17415993.2022.2149266","url":null,"abstract":"<div><p>In this review, we spotlight the methods for the direct synthesis of synthetically and biologically important 1-sulfonyl-1, 2, 3-triazoles <em>via</em> [3+2] cycloaddition between easily available terminal alkynes and sulfonyl azides. The review is divided into two major sections. The first section focuses exclusively on the synthesis of 1-(<em>N</em>-sulfonyl)-4-substituted 1,2,3-triazoles, while the second section will discuss preparation of 1-(<em>N</em>-sulfonyl)-5-substituted 1,2,3-triazole derivatives.</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 377-391"},"PeriodicalIF":2.2,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43612376","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":"Synthesis, spectroscopic characterization, biological activity, and conducting properties of functionalized Ni(II) dithiocarbamate complexes with solvent extraction studies of the ligands","authors":"Vinay Kumar Maurya , Lal Bahadur Prasad , Anupam Singh , Kunal Shiv , Akhilesh Prasad","doi":"10.1080/17415993.2022.2157680","DOIUrl":"10.1080/17415993.2022.2157680","url":null,"abstract":"<div><p>A series of new nickel(II) dithiocarbamate complexes of general formula [M L<sub>2</sub>], (<em>where L=</em>benzyl(4-fluorobenzyl)carbamodithioate (L1), benzyl(4-cyanobenzyl)carbamodithioate (L2), ethyl(4-methylbenzyl)carbamodithioate (L3), (4-methoxybenzyl) (naphthalen-1-ylmethyl)carbamodithioate (L4) and ethyl(4-methoxybenzyl)carbamodithioate (L5)) have been synthesized, and characterized <em>via</em> elemental analysis, FT-IR, electronic spectra, <sup>1</sup>H NMR, <sup>13</sup>C NMR, Mass spectrometry and Thermogravimetric analysis (TGA). The continuous variation method (Job's method) was used to determine the stoichiometry of the complexes. TGA was used to analyze the thermal decomposition behavior of metal complexes in nitrogen atmosphere. As a result of the thermal decomposition process, all of the complexes produced NiS as the final product. X-ray Diffraction (XRD), Energy dispersive X-ray analysis (EDAX), and Transmission electron microscopy (TEM) studies confirm the formation of NiS nanomaterial. Crystalline size of NiS was obtained between 19.97 to 21.35nm range by applying the Scherrer equation using XRD. Solid-state electrical conductivities reveal that all the complexes behave as a semiconductor at room temperature. All the synthesized dithiocarbamate ligands and complexes were screened against five human bacterial pathogens (<em>Escherichia coli</em>, <em>Staphylococcus aureus</em>, <em>Salmonella typhi</em>, <em>Aeromonas hydrophila</em>, and <em>Shigella boydii</em>) by disc diffusion method. Solvent extraction studies show that the ligand has strong extractability towards metal ions in a basic medium (pH=10).</p></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"44 3","pages":"Pages 336-353"},"PeriodicalIF":2.2,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48565938","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}