Phosphorus, Sulfur, and Silicon and the Related Elements最新文献

{"title":"Tris(hydroxymethyl)phosphine oxide – synthesis, chemistry, and applications","authors":"","doi":"10.1080/10426507.2024.2350580","DOIUrl":"10.1080/10426507.2024.2350580","url":null,"abstract":"<div><p>Tris(hydroxymethyl)phosphine oxide, (HOCH₂)₃PO (THPO), is recognized as an efficient flame-retardant polyol and a derivative of PH₃ – an environment-friendly, halogen-free source for phosphorus compounds and polymers. Synthesis and industrial production of THPO are based on straightforward oxidation of tris(hydroxymethyl)phosphine, (HOCH₂)₃P (THP), or neutralized tetrakis(hydroxymethyl)phosphonium chloride (THPC), or sulfate (THPS), by air/O₂ or H₂O₂. In alkaline aqueous media, THP is oxidized by water with liberation of H₂. As an alcohol, THPO readily reacts with isocyanates, epoxides, aziridines, and carboxylic acid derivatives, and is widely used as crosslinker or chain-extender to produce flame-retardant polyurethanes, polyethers, polyesters, and composite materials. Similarly, with compounds containing E–Cl bonds (E = P, Si, and S), THPO forms a variety of flame-retardant P/E-compounds or polymers. Condensation of THPO with phenols proceeds <em>via</em> cleavage of a P–C bond of THPO and liberation of CH₂O that leads to flame-retardant THPO-phenol resins. With functionalized alkyl halides, THPO forms tris(alkoxymethyl)phosphine oxide monomers containing, for example, pendant allyl, propargyl, or silane groups. Halogenation of THPO leads to tris(chloromethyl)phosphine oxide, (ClCH₂)₃PO, or tris(bromomethyl)phosphine oxide, (BrCH₂)₃PO, useful for syntheses of multifunctional organophosphorus compounds, for example, tris(aminomethyl)phosphine oxide, (NH₂CH₂)₃PO, and phosphorus-containing podands. Similar to THPO, tris(hydroxymethyl)phosphine sulfide, (HOCH₂)₃PS, is used in preparation of flame-retardant components for polymers, and, in synthesis of asymmetric phosphorus compounds.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 5","pages":"Pages 337-376"},"PeriodicalIF":1.4,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141118583","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis, structural characterization of phenoxo-bridged zinc(II) complexes and their binding interaction with the spike protein of SARS-CoV-2","authors":"","doi":"10.1080/10426507.2024.2354748","DOIUrl":"10.1080/10426507.2024.2354748","url":null,"abstract":"<div><p>The research article reports the synthesis and structural study of the optimized geometry of selenium (Se) bearing 24- and 28- membered macrocyclic Schiff bases, <strong>L a H 2</strong>, <strong>L b H 2</strong> and their reactions with zinc metal ion. The reactions of the macrocyclic Schiff bases with ZnCl₂ in 1:2 molar ratios result in the formation of bimetallic Zn(II) complexes having molecular composition [Se{(CH₂)₂N = CPh(4-CH₃-C₆H₂O) PhC = O}₂ · Zn₂Cl₂], (<strong>1</strong>) and [Se{(CH₂)₃N = CPh(4-CH₃-C₆H₂O)PhC = O}₂ · Zn₂Cl₂], (<strong>2</strong>). Moreover, as confirmed by various physico-chemical techniques such as elemental analysis, UV–Vis, FTIR,¹H NMR, and mass spectrometry, the proligands underwent partial hydrolytic cleavage at one of the C = N positions and behave like hexadentate (N₂O₄) ligands binding to two Zn(II) ions <em>via</em> bridging through the O_phenolic atoms, which results in a square pyramidal geometry around Zn(II) with the chlorine atom occupying axial positions. Further, following density functional study, the stable optimized configuration of the Schiff bases <strong>L a H 2</strong> and <strong>L b H 2</strong> is found to adopt bowl shape geometry. Conversely, in molecular docking studies, the synthesized complex <strong>1</strong> exhibits a significantly stronger binding affinity (−8.7 kcal/mol) to the spike protein of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) as compared to the common coronavirus disease 2019 (COVID-19) treatment drugs such as chloroquine, hydroxychloroquine, and remdesivir with activity percentage showing more than 20% overall effectiveness than remdesivir and thus indicating its potential for COVID-19 therapeutics.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 5","pages":"Pages 406-419"},"PeriodicalIF":1.4,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141508277","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis and characterization of a high-temperature polycyanophosphate resin","authors":"","doi":"10.1080/10426507.2024.2360469","DOIUrl":"10.1080/10426507.2024.2360469","url":null,"abstract":"<div><p>A phosphorus-containing polymer with very high thermo-oxidative stability was synthesized for the first time by addition of silver nitrate to tricyanophosphine (P(CN)₃). By optimizing the reaction time and silver nitrate concentration to a 1:1 molar ratio, a new polycyanophosphate [p(CP)] was formed as the primary phosphorus-containing product over the competing species, P(CN)₃. The reactions and products were monitored by FT-IR, ICP-OES, NMR, and XPS spectroscopic techniques, which indicated a complicated oxidation reaction that converted the P(III) precursor species to P(V) polyphosphate species with pendant cyano- and isocyano- moieties. The p(CP) resin was found to contain a high (17.6 at.%) amount of phosphorus by ICP-OES, which contributed to its excellent thermo-oxidative resistance with a high char yield of over 60 wt.% at 1000 °C (1273 K) in air, indicating that the material could be particularly useful for high-temperature applications.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 5","pages":"Pages 429-438"},"PeriodicalIF":1.4,"publicationDate":"2024-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141508301","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Electron-withdrawing effect and CH-acidity of carboranes: effect of nature and position of substituents","authors":"Igor B. Sivaev ,&nbsp;Sergey A. Anufriev ,&nbsp;Akim V. Shmal’ko","doi":"10.1080/10426507.2024.2335982","DOIUrl":"10.1080/10426507.2024.2335982","url":null,"abstract":"<div><p>The effect of substituents of various natures at boron atoms in different positions of the carborane cage on the CH-acidity of carborane derivatives and the electron-withdrawing effect of C-carboranyl groups is considered using ¹H NMR spectroscopy data.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 4","pages":"Pages 299-302"},"PeriodicalIF":1.3,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140567915","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of bis-(benzhydryloxy) substituted axially silicon(IV) phthalocyanine: investigation of photophysical, photochemical, and computational electronic properties","authors":"Derya Güngördü Solğun ,&nbsp;Umit Yildiko ,&nbsp;Mehmet Salih Ağırtaş","doi":"10.1080/10426507.2024.2341147","DOIUrl":"10.1080/10426507.2024.2341147","url":null,"abstract":"<div><p>Synthesis of axially disubstituted silicon(IV) phthalocyanine bearing benzhydryloxy groups obtained by reaction of SiPcCl₂ with diphenylmethanol is reported. Characterization of the compound was performed by ¹H and ¹³C NMR, UV–Vis, mass spectrometry, and FT-IR spectroscopy. Photophysical and photochemical properties were investigated. Fluorescence spectra measurements were performed in DMSO as solvent. A preferred chemical method was used to determine the amount of singlet oxygen production. Optimizations were calculated for the single-molecule Si-Pc with the 6–311 G (d, p) basis set at the B3LYP and B3PW91 levels of density functional theory (DFT). The charge transfer (or) charge delocalization between intramolecular donor–acceptor groups was determined by NBO analysis. Furthermore, molecular electrostatic potential, Fukui functions, electrophilic and nucleophilic character maps were calculated. The electronic structure and energy parameters of the investigated compound were determined to be Δ<em>E</em>_calc = 2.19 eV by DFT calculation and Δ<em>E</em>_opt = 1.84 by experimental UV spectrum.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 4","pages":"Pages 324-336"},"PeriodicalIF":1.3,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140567918","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of new 4-aminobenzoic acid (PABA) hydrazide-hydrazone/sulfonate hybrids and antimicrobial evaluation with ascorbic acid/salicylic acid/N-acetyl cysteine combinations","authors":"M. İhsan Han ,&nbsp;Ufuk İnce ,&nbsp;G. Pelin Coşkun ,&nbsp;Kaan Birgül ,&nbsp;Şengül Dilem Doğan ,&nbsp;Amir Ashoorzadeh ,&nbsp;Ş. Güniz Küçükgüzel","doi":"10.1080/10426507.2024.2341145","DOIUrl":"10.1080/10426507.2024.2341145","url":null,"abstract":"<div><p>One of the most serious threats to human health is the increasing prevalence of drug-resistant pathogens. The development of new antibiotics capable of combating drug resistance is critical. In various bacteria and plant species, 4-aminobenzoic acid (PABA) is produced and used as a substrate for folate generation. In this study, a new series of PABA analogs were synthesized and evaluated for their antimicrobial activity. Thirteen novel compounds were prepared by linking PABA hydrazide to sulfonate esters <em>via</em> a hydrazone bridge (<strong>4a</strong>–<strong>m</strong>). The structures of these compounds were characterized by ¹H and ¹³C NMR and FT-IR spectroscopy as well as by LC-MS. Following structural characterization, all compounds were tested for their antimicrobial activity against <em>Staphylococcus aureus</em> (ATCC 29213), <em>Enterococcus faecium</em> (ATCC 19434), <em>Escherichia coli</em> (ATCC 25922), <em>Pseudomonas aeruginosa</em> (ATCC 27853), and <em>Candida albicans</em> (ATCC 10231) strains. Four compounds were found to have moderate antimicrobial activity against the <em>P. aeruginosa</em> strain. These compounds, including <strong>4e, 4f, 4g</strong>, and <strong>4m</strong>, containing a hydrazide-hydrazone sulfonate functionality, showed the best MIC value of 64 μg/mL. In addition, synergistic effects of ascorbic acid, salicylic acid, and <em>N</em>-acetyl cysteine (NAC) with synthesized compounds were also investigated. It was observed that the combination of compounds <strong>4f</strong> and <strong>4g</strong> with NAC showed antipseudomonal activity with MIC values of 32 μg/mL and 16 μg/mL, respectively, against the <em>P. aeuriginosa</em> strain. The antimicrobial activity of <strong>4f</strong> and <strong>4g</strong> was enhanced by two folds in combination with NAC. Our findings in this study can be crucial for the development of new potent antimicrobial agents.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 4","pages":"Pages 316-323"},"PeriodicalIF":1.3,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140666913","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis, characterization and anticancer screening of novel phenylbenzylidene thiosemicarbazone derivatives","authors":"S. Anisree ,&nbsp;P. Shanmugavelan ,&nbsp;P. Vijayalakshmi ,&nbsp;Ram Kishore ,&nbsp;Nitin Srivastava","doi":"10.1080/10426507.2024.2330935","DOIUrl":"10.1080/10426507.2024.2330935","url":null,"abstract":"<div><p>Ten derivatives of phenylbenzylidene thiosemicarbazones (<strong>1</strong>–<strong>10</strong>) were synthesized by multicomponent reaction between hydrazine hydrate, isothiocyanate and substituted aldehydes in the presence of the phase transfer reagent Triton-B and subsequently heating the mixture. The synthesized compounds <strong>1</strong>, <strong>2</strong>, <strong>5</strong>, <strong>8</strong> demonstrated to act as highly potent anticancer agents. They showed anticancer activity by mobilizing cellular ⁵⁹Fe, inhibiting cellular uptake of ⁵⁹Fe from ⁵⁹Fe₂-Tf, and mediating the ascorbate oxidation. Further, the structure activity relationship revealed that the donor atom and its stabilization resulted in better anticancer activity. The softness of the chelating donor atoms N and S yielded redox active iron complexes, which easily mediated ascorbate oxidation. This study identified the selective and potential chelators, which may act as anticancer agents and require further <em>in vivo</em> screening in future.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 4","pages":"Pages 267-276"},"PeriodicalIF":1.3,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140299826","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A facile ultrasonic synthesis approach to 3-H-quinazolinethione derivatives and their urease inhibition studies","authors":"Nedime Çalışkan ,&nbsp;Gülay Akyüz ,&nbsp;Emre Menteşe","doi":"10.1080/10426507.2024.2333471","DOIUrl":"10.1080/10426507.2024.2333471","url":null,"abstract":"<div><p>In this study, a new series of 3<em>H-</em>quinazoline-4-thione derivatives were synthesized under ultrasonic irradiation conditions with high yield in a short time. The new compounds were characterized by FT-IR,¹H, and ¹³C NMR spectral data. The antiurease activities of all new compounds were tested according to the method by Weatherburn. The inhibition results with the 3<em>H-</em>quinazoline-4-thione ring compounds were compared with those of some previously synthesized 3<em>H-</em>quinazolin-4-ones. More effective results were found for most quinazolinethione compounds. All new synthesized compounds have effective urease inhibition activity. Especially, the compound 2-(4-nitrobenzyl)quinazoline-4(3<em>H</em>)-thione (<strong>2i</strong>) has the best inhibition results with IC₅₀ = 1.6 ± 0.049 μg/mL.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 4","pages":"Pages 293-298"},"PeriodicalIF":1.3,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140370942","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Green conversion of CO2 by N-heterocyclic carbene-CO2 adducts grafted hierarchical porous silica microspheres","authors":"Xueting Liu ,&nbsp;Kuayue Li ,&nbsp;Wenkui Liu ,&nbsp;Peng Cui ,&nbsp;Fengyu Wei","doi":"10.1080/10426507.2024.2332891","DOIUrl":"10.1080/10426507.2024.2332891","url":null,"abstract":"<div><p>The multiphase catalysts DMSNs-Cb-X containing NHC-CO₂ adducts were synthesized by soft template method that is, first preparing dendritic multi-model pore silica nanoparticles (DMSNs) with central-radial structure, and then grafting imidazoline functional groups, and finally allowing to react with dimethyl carbonate to graft NHC-CO₂ adducts. The investigations had the scope to improve the performance and to elucidate the effect of NHC-CO₂ adducts on the CO₂ cycloaddition reaction. The optimum catalyst DMSNs-Cb-1 and the optimum reaction conditions (200 mg, 100 °C, 10 h) were obtained <em>via</em> thermogravimetric analysis. CO₂ cycloaddition reaction with epoxide DMSNs-Cb-1 can convert CO₂ and epoxide to cyclic carbonate at ambient pressure without solvent and co-catalysts (1 bar, 100 °C). The reaction proceeds with high yield and high conversion frequency (TOF = 27.4 h⁻¹). The prepared catalyst is easily recovered and still has high activity after five cycles of experiments. The excellent catalytic performance of the obtained catalyst can be attributed to the synergy of hierarchical porous structure and NHC-CO₂ adducts acting as CO₂ adsorption sites as well as zwitterionic catalytic sites. This work demonstrates an efficient strategy for green conversion of CO₂ into cyclic carbonates.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 4","pages":"Pages 283-292"},"PeriodicalIF":1.3,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140372102","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Investigation of the effect of halide counterions on the potential corrosion inhibitor in imidazolium-based ionic liquids","authors":"Abdelmajeed Adam Lagum ,&nbsp;Saroj Sharma ,&nbsp;Anupam Yadav ,&nbsp;Parminder Singh ,&nbsp;Shakir Mahmood Saeed ,&nbsp;Russul R. Abbass ,&nbsp;Ali H. Hameed ,&nbsp;Mustafa M. Kadhim","doi":"10.1080/10426507.2024.2340006","DOIUrl":"10.1080/10426507.2024.2340006","url":null,"abstract":"<div><p>Imidazolium (IMZ)-based ionic liquids (ILs) with various counter ions were investigated as potential corrosion inhibitors. Furthermore, parameters such as bond lengths, bond angles, and dihedral bonds were investigated to demonstrate the adsorption sites of molecules. Moreover, in order to compare the efficiency of the inhibitors, other parameters such as energy gap, hardness, the LUMO, and the HOMO were investigated. The HOMO and LUMO values increased from −4.370 and −0.106 eV to −4.959 and −0.156 eV, respectively, by changing F⁻ to I⁻. Moreover, the softness of the IMZ base changed from 0.469 to 0.417 eV by increasing the radius of the halide ion. The trend of the band gap value in going from F⁻ to I⁻ changes from 4.264 to 4.797 eV. The total electron density was computed to show the adsorption sites based on the electron density. According to the molecular reactivity results, the inhibitory efficiency of the inhibitors was in the following order: BMI-F &gt; BMI-Cl &gt; BMI-Br &gt; BMI-I. Investigating the IMZ-based ILs with various counterions to evaluate the inhibition profile of molecules provides useful insights into computational protocols for the study of corrosion inhibitors.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":"199 4","pages":"Pages 308-315"},"PeriodicalIF":1.3,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140972124","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}