Russian Journal of General Chemistry最新文献

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Next-Generation Nonwoven Materials 新一代非织造材料
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-07 DOI: 10.1134/S1070363226160115
E. A. Kolomeitseva, N. S. Dymnikova, E. V. Erokhina
{"title":"Next-Generation Nonwoven Materials","authors":"E. A. Kolomeitseva,&nbsp;N. S. Dymnikova,&nbsp;E. V. Erokhina","doi":"10.1134/S1070363226160115","DOIUrl":"10.1134/S1070363226160115","url":null,"abstract":"<p>This article is devoted to the development and study of new-generation domestic nonwoven materials with multifunctional protective properties. The relevance of this work is determined by the need for effective import substitution and the creation of environmentally safe technical fabrics with fire-, heat-, and bioprotective characteristics. Innovative halogen-free flame retardants of the Tezagran and Termotex series based on nitrogen-containing phosphonic acid derivatives are presented. Their action is based on the phosphorus–nitrogen synergistic effect, which ensures the formation of a strong carbonized layer and a significant reduction in the release of toxic products (CO and HCN) during pyrolysis compared with foreign analogues. The results of a comparative analysis of the fire-safety and biological-resistance parameters of materials based on natural (flax and hemp) and synthetic (preox and aramid) fibers are presented. It was experimentally demonstrated that the developed formulations provide high oxygen index values (above 35%) and resistance to burn-through at 800°C, which meets or exceeds existing standards. Particular attention is paid to the development of environmentally safe bulky insulation materials for the construction industry and transport engineering that can operate effectively under the extreme conditions of the Arctic. The practical significance of the study was confirmed by successful testing of pilot-scale batches at Russian Railways and by obtaining Russian patents. The developed multifunctional materials are nontoxic and cost-effective and offer broad prospects for ensuring comprehensive safety in leading industries.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927160","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}
引用次数: 0
From a Forgotten Synthesis to a New Veterinary Drug 从被遗忘的合成到一种新的兽药
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-07 DOI: 10.1134/S1070363226160085
D. E. Rozhin, N. A. Kuznetsov, Yu. V. Suvorova
{"title":"From a Forgotten Synthesis to a New Veterinary Drug","authors":"D. E. Rozhin,&nbsp;N. A. Kuznetsov,&nbsp;Yu. V. Suvorova","doi":"10.1134/S1070363226160085","DOIUrl":"10.1134/S1070363226160085","url":null,"abstract":"<p>An improved laboratory method for synthesizing the active pharmaceutical ingredient (API) 3,5-diamino-1,2,4-thiadiazole (Amtizol) was scaled up, the necessary process equipment was selected, and a process flow chart was developed. The proposed technology for producing 3,5-diamino-1,2,4-thiadiazole will reduce its adverse environmental impact by decreasing gaseous emissions during production and will provide a higher yield of the target product. Russian Government Resolution No. 395 of March 27, 2025, provides for the development of veterinary drug production in 2025–2030, making the development of a new veterinary drug particularly relevant. Hypoxia is common in animals and accompanies virtually all diseases. Therefore, an antihypoxic drug was developed. A dispersible tablet was selected as the dosage form because it is convenient for animals and their owners. A competitive analysis revealed that no similar dosage form is available among antihypoxic agents. Excipients were selected to ensure tablet disintegration in the animal’s mouth, mechanical strength, and compressibility, and a dispersible tablet formulation was developed. Tablet samples were prepared in the laboratory, and the identity, dispersibility, and strength of the drug were evaluated. The cost of the finished product was calculated to confirm the economic feasibility of the project, demonstrating that the drug under development will be competitive. Therefore, the proposed formulation can be scaled up by Russian pharmaceutical manufacturers.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927024","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}
引用次数: 0
Use of Phytoncides for Indoor Air Disinfection 植物杀菌剂在室内空气消毒中的应用
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-07 DOI: 10.1134/S1070363226160140
E. A. Vlasova, E. V. Naidenko
{"title":"Use of Phytoncides for Indoor Air Disinfection","authors":"E. A. Vlasova,&nbsp;E. V. Naidenko","doi":"10.1134/S1070363226160140","DOIUrl":"10.1134/S1070363226160140","url":null,"abstract":"<p>The effects of phytoncides contained in the juices and essential oils of various plants (garlic, ginger, onion, lemon, and pine needles) on the growth and development of pathogenic microorganisms present in classroom air during the autumn–winter period were studied. For this purpose, the growth inhibition zones and the numbers of microbial colonies grown on meat–peptone agar, a nutrient medium, were recorded over 1–7 days. After one day, the microbial growth inhibition zones in the presence of lemon juice (essential oil) and the juices (essential oils) of the other plants were 1.05 (1.25) and 1.75 (2.25) times larger, respectively, than those observed in the absence of the substances studied. Throughout the experiment, the phytoncidal activity of the plant essential oils, assessed from the microbial growth inhibition zones, was slightly higher than that of the juices of the same plants. This was apparently because essential oils evaporate much more slowly than juices owing to a combination of their chemical properties, localization in plants, and higher molecular weights. Pine needles exhibited the highest phytoncidal activity throughout the experiment and sharply slowed the increase in the number of microbial colonies. By the end of the experiment, the number of pathogen colonies formed in the presence of pine needles was 2.5 times lower than that in the blank experiment without phytoncides. The results may find practical applications in medicine in the development of air purification methods for preventing infections, particularly in operating rooms and hospital wards; in the food industry; in water disinfection; and in pharmaceutical manufacturing to ensure product safety and prevent spoilage.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927032","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}
引用次数: 0
Emissions of Atmospheric Pollutants from Stationary Sources in the Siberian Federal District 西伯利亚联邦区固定污染源大气污染物排放
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-07 DOI: 10.1134/S1070363226160152
A. L. Kuletsan, N. A. Marchuk, K. A. Nikitin, I. A. Samoilov, M. A. Rumyantsev, L. T. Manukian
{"title":"Emissions of Atmospheric Pollutants from Stationary Sources in the Siberian Federal District","authors":"A. L. Kuletsan,&nbsp;N. A. Marchuk,&nbsp;K. A. Nikitin,&nbsp;I. A. Samoilov,&nbsp;M. A. Rumyantsev,&nbsp;L. T. Manukian","doi":"10.1134/S1070363226160152","DOIUrl":"10.1134/S1070363226160152","url":null,"abstract":"<p>This article analyzes emissions of atmospheric pollutants from stationary sources in the Siberian Federal District. The results showed that SO<sub>2</sub>, CO, C and volatile organic compounds, particulate matter, and NO are the priority air pollutants in most cities of the Siberian Federal District. The data indicate sharp increases in emissions of carbon monoxide, hydrocarbons, including volatile organic compounds, and nitrogen monoxide. From 2004 to 2024, these emissions increased by 24, 90, and 32%, respectively. In addition, the results indicate a sharp increase in disease incidence among residents of the Siberian Federal District. These diseases include endocrine and metabolic disorders, nervous system diseases, and respiratory diseases. Their incidence increased by 76.53, 3.85, and 43.29%, respectively.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927159","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}
引用次数: 0
Reaction of Unsaturated Meldrum’s Acid Derivatives with Azide Ions 不饱和梅尔德鲁姆酸衍生物与叠氮离子的反应
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-07 DOI: 10.1134/S1070363226160073
S. A. Sokov, G. Z. Raskildina, A. A. Golovanov
{"title":"Reaction of Unsaturated Meldrum’s Acid Derivatives with Azide Ions","authors":"S. A. Sokov,&nbsp;G. Z. Raskildina,&nbsp;A. A. Golovanov","doi":"10.1134/S1070363226160073","DOIUrl":"10.1134/S1070363226160073","url":null,"abstract":"<p>The reactions of unsaturated Meldrum’s acid derivatives with azide ions were studied. The selectivity and reaction pathways were determined for two types of substrates, namely enyne and spirocyclopropane derivatives. The enyne derivative undergoes regioselective Huisgen 1,3-dipolar cycloaddition to form a 1,2,3-triazole, while the trimethylsilyl group remains intact, providing opportunities for subsequent modification of the molecule. In contrast, the spirocyclopropane derivative does not undergo cycloaddition but reacts through nucleophilic opening of the strained three-membered ring to form an organic azide. The structures of all the compounds obtained were confirmed using a combination of spectroscopic methods, including NMR spectroscopy, and elemental analysis. The thermal stability of the synthesized azide was assessed using simultaneous thermogravimetric and differential thermal analysis. The low enthalpy of decomposition indicates that this azide is not an explosive compound. The cytotoxicity of the compounds obtained toward human stromal, lung carcinoma, and melanoma cell lines was evaluated using the MTT assay. The cells remained completely viable at a concentration of 50 μM, indicating the absence of toxic effects under these conditions. A fundamental difference was found between the reactivities of activated unsaturated moieties in Meldrum’s acid derivatives. The developed approaches can be used to obtain new triazole and azide structures of interest as synthons for medicinal chemistry and materials science. The results contribute to the development of methods for selective transformations of highly reactive carbocyclic systems and expand the range of tools available for designing biologically active molecules and functional materials.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927158","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}
引用次数: 0
Elastomer Nanocomposites with Carbon Nanotubes Modified by Laser Ablation 激光烧蚀改性碳纳米管弹性体纳米复合材料
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-07 DOI: 10.1134/S1070363226160139
Alexandr V. Shchegolkov, Aleksey V. Shchegolkov
{"title":"Elastomer Nanocomposites with Carbon Nanotubes Modified by Laser Ablation","authors":"Alexandr V. Shchegolkov,&nbsp;Aleksey V. Shchegolkov","doi":"10.1134/S1070363226160139","DOIUrl":"10.1134/S1070363226160139","url":null,"abstract":"<p>The effect of laser treatment on the structure and functional properties of multiwalled carbon nanotubes (MWCNTs) synthesized by a microwave method using ferrocene and graphite as precursors, as well as on the electrical and thermophysical characteristics of elastomer nanocomposites based on them, was studied. The MWCNTs were modified by laser ablation using a pulsed Nd:YAG laser with a treatment duration of up to 5 min and a source power of up to 1 kW. The nanocomposites were prepared using the two-component Silagerm 8030 silicone elastomer with a modified MWCNT content of 4 wt %. Scanning electron microscopy and Raman spectroscopy showed that laser irradiation causes significant morphological and structural changes, including a decrease in the nanotube diameter from 40–80 to 20–30 nm due to ablation of the outer graphene layers, the formation of a developed network architecture, the complete removal of catalytic iron particles from the surface, and modification of the defect structure, as confirmed by a shift of the D band from 1345.2 to 1341 cm<sup>−1</sup> and an increase in the <i>I</i><sub>D</sub>/<i>I</i><sub>G</sub> ratio from 1.172 to 1.175, while the position of the G band remains unchanged. The composite containing modified MWCNTs was shown to exhibit improved functional characteristics compared with its unmodified counterparts: the thermal conductivity increased from 0.31 to 0.34 W/(m K), the thermal diffusivity from 1.7 × 10<sup>−7</sup> to 1.72 × 10<sup>−7</sup> m<sup>2</sup>/s, and the electrical conductivity from 0.1 to 0.12 S/m. The results indicate that laser treatment is promising for the targeted modification of the morphology and structure of carbon nanotubes to produce electrically conductive polymer composites with improved electrical and thermophysical properties.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927030","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}
引用次数: 0
Acyl Derivatives of 2,3,6,7,8,9-Hexahydro-1,5-diazonines: Synthesis, Structure and Tautomeric Transformations 2,3,6,7,8,9-六氢-1,5-重氮嘧啶酰基衍生物:合成、结构和互变异构转化
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-07 DOI: 10.1134/S1070363226601225
Nadezhda A. Anisimova, Valeriy V. Mikhailov
{"title":"Acyl Derivatives of 2,3,6,7,8,9-Hexahydro-1,5-diazonines: Synthesis, Structure and Tautomeric Transformations","authors":"Nadezhda A. Anisimova,&nbsp;Valeriy V. Mikhailov","doi":"10.1134/S1070363226601225","DOIUrl":"10.1134/S1070363226601225","url":null,"abstract":"<p>The reaction of 2,2,4,11,11,13-hexamethyl-1,5,10,14-tetraazacyclooctadeca-4,13-diene with carboxylic acid chlorides afforded <i>N</i>- and <i>C</i>-acyl substituted 2,3,6,7,8,9-hexahydro-1<i>H</i>-1,5-diazonines, which in solutions of deuterated solvents (CDCl<sub>3</sub>, CD<sub>3</sub>OD, DMSO-<i>d</i><sub>6</sub>) exhibit an increased tendency to prototropic rearrangements. It was shown that <i>N</i>- and <i>C</i>-acyldiazonines exist in different tautomeric forms: <i>N</i>-acyldiazonines as the keto-imine form, while <i>C</i>-acyl isomers exist as the enol-enamine form. The structure of the obtained <i>N</i>- and <i>C</i>-acyldiazonines and their tautomeric transformations were studied by <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy using two-dimensional <sup>1</sup>H–<sup>13</sup>C HMQC, HMBC, and <sup>1</sup>H–<sup>1</sup>H COSY experiments.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148927033","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}
引用次数: 0
Recent Trends in the Chemical Modification of Flax Fiber for Polymer Composite Materials: A Critical Review 高分子复合材料用亚麻纤维化学改性研究进展综述
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-05 DOI: 10.1134/S1070363226160012
S. V. Aleeva, S. E. Shipova, E. N. Nikiforova, S. A. Koksharov
{"title":"Recent Trends in the Chemical Modification of Flax Fiber for Polymer Composite Materials: A Critical Review","authors":"S. V. Aleeva,&nbsp;S. E. Shipova,&nbsp;E. N. Nikiforova,&nbsp;S. A. Koksharov","doi":"10.1134/S1070363226160012","DOIUrl":"10.1134/S1070363226160012","url":null,"abstract":"<p>The dynamics of the polymer composite materials market demonstrate a remarkable rate of adoption of organic fiber-reinforced plastics in major industrial sectors, medicine, sports and household equipment, and household goods. Natural fibers, particularly flax fibers, are of practical interest because of their low cost, environmental friendliness, biodegradability, acceptable mechanical properties, and availability. The expanding use of flax in composite materials imposes new requirements on the quality of flax fiber products. This progress highlights the need for broader studies and deeper knowledge of the possibilities for modifying the physical and mechanical properties of reinforced polymers through fiber pretreatment and selection of treatment conditions with consideration of the required characteristics and operating conditions of composite products. The objective is to analyze recent literature, published mainly over the past three years, addressing the principal issues that hinder the widespread use of flax fiber in the composite industry. Preservation and rational utilization of the natural potential of technical flax fiber in long-fiber forms of reinforcing fillers eliminates the adverse effect of anisotropy in the geometric and mechanical properties of elementary flax fibers. We analyze experience in the use of chemical treatments to overcome the natural porosity and hydrophilicity of flax materials, identify unresolved problems, and search for effective biomimetic approaches to overcoming these difficulties. Information on the structure and functions of the object of biomimicry, the xylem of the flax stem, provides the key to developing moisture-resistant composite materials based on advanced two-stage molding methods using different types of binders.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148926709","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}
引用次数: 0
Promising Methods for Imparting Flame-Retardant Properties to Textile Materials 赋予纺织材料阻燃性能的有前途的方法
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-05 DOI: 10.1134/S1070363226160024
A. V. Abakumov, A. S. Fedorinov, O. I. Odintsova, A. A. Malygina, S. V. Smirnova
{"title":"Promising Methods for Imparting Flame-Retardant Properties to Textile Materials","authors":"A. V. Abakumov,&nbsp;A. S. Fedorinov,&nbsp;O. I. Odintsova,&nbsp;A. A. Malygina,&nbsp;S. V. Smirnova","doi":"10.1134/S1070363226160024","DOIUrl":"10.1134/S1070363226160024","url":null,"abstract":"<p>A wide range of textile auxiliaries are used as flame retardants. They are required to minimize the risk of ignition in the event of contact with a small heat source, such as a cigarette, candle, or faulty electrical equipment. If the material ignites, the flame retardant slows combustion and prevents the fire from spreading to other objects. Flame-retardant finishing is one of the most important types of textile finishing and can significantly improve the safety of fabrics used for domestic, commercial, public, and industrial purposes. A wide range of chemical formulations are used for flame-retardant finishing. Traditional flame retardants are based on halogens, phosphorus, and nitrogen; however, they have several significant disadvantages: formaldehyde release, generation of hazardous wastewater, reduction in textile strength, changes in fabric shade, and release of toxic gases. Innovative technologies for imparting flame resistance to textile materials are based on plasma, nano-, and layer-by-layer technologies. Flame-retardant coatings based on natural resources are currently of particular interest. This article considers advanced methods for producing flame-retardant coatings: microencapsulation, sol–gel technology, UV curing, and spraying. The combustion mechanism and general classification of flame retardants, as well as the use of boron- and inorganic phosphorus-based flame-retardant formulations, are considered. Particular attention is paid to the use of nanoparticles and natural environmentally friendly resources of animal origin in the flame-retardant finishing of fabrics. The current trend toward the development of environmentally friendly production methods has led to the investigation of harmless, biodegradable substances that are wastes from other industries as flame retardants and have considerable potential for imparting flame-retardant properties to textile materials.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148926836","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}
引用次数: 0
Effect of the Nitro Group Position on Conformational Diversity and Intramolecular Hydrogen Bonding in Nitro-Hydroxy-Methylazobenzene Molecules 硝基位置对硝基-羟基-甲基偶氮苯分子构象多样性和分子内氢键的影响
IF 1 4区 化学
Russian Journal of General Chemistry Pub Date : 2026-09-05 DOI: 10.1134/S1070363226160036
A. A. Fedorova, O. V. Lefedova
{"title":"Effect of the Nitro Group Position on Conformational Diversity and Intramolecular Hydrogen Bonding in Nitro-Hydroxy-Methylazobenzene Molecules","authors":"A. A. Fedorova,&nbsp;O. V. Lefedova","doi":"10.1134/S1070363226160036","DOIUrl":"10.1134/S1070363226160036","url":null,"abstract":"<p>The predominant conformation or tautomeric form of a compound can affect the selectivity and yield of the target product in a catalytic process. Nitro-hydroxy-methylazobenzenes are used as reactants in the catalytic synthesis of benzotriazoles and contain two reactive groups that readily interact with hydrogen under hydrogenation conditions. Depending on the position of the nitro group and the orientation of the rings relative to the –N=N– bond, several conformers may be formed, as previously demonstrated for 2-nitro-2′-hydroxy-5′-methylazobenzene. In this study, the structure of 4-nitro-2′-hydroxy-5′-methylazobenzene in the gas phase, in hexane, water, toluene, dimethylformamide, and 2-propanol was investigated using density functional theory (CAM-B3LYP/6-311++G(d, p)) and a continuum solvation model. Experimental and calculated UV and IR spectra were obtained. Only two structures were found both in the gas phase and in the solvents. The lowest-energy conformer is characterized by greater coplanarity and a medium-strength intramolecular hydrogen bond (IMHB) between the β-nitrogen atom of the azo group and the hydrogen atom of the hydroxy group. Intramolecular proton transfer does not occur, and the prototropic equilibrium is shifted toward the azo form. A comparison of the calculation results for 2-nitro- and 4-nitro-2′-hydroxy-5′-methylazobenzene showed that, regardless of the position of the nitro group and the nature of the solvent, ortho-hydroxy-nitroazobenzenes most likely exist exclusively as cis isomers featuring a medium-strength IMHB between the β-nitrogen atom of the –N=N– group and the hydrogen atom of the OH group. At the same time, the calculated IMHB characteristics indicate that the position of the NO<sub>2</sub> group affects all hydrogen-bond parameters: its energy, length, and O–H···N angle. An increase in the dielectric constant of the solvent lowers the energies of the conformers and weakens the IMHB.</p>","PeriodicalId":761,"journal":{"name":"Russian Journal of General Chemistry","volume":"96 9","pages":""},"PeriodicalIF":1.0,"publicationDate":"2026-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148926759","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}
引用次数: 0
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