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  • 1
    In: Butlerov Communications, Innovation Publishing House Butlerov Heritage Ltd, Vol. 57, No. 3 ( 2019-03-31), p. 83-88
    Abstract: The production of new 3-azabicyclononane derivatives is an important trend in the synthesis of organic compounds. It is known that 3-azabicyclononane is a key pharmacophore of a number of plant alkaloids that are widely used in medicine (aconitin, quinidine, tropane, cocaine, garnet, etc.). Among synthetic heterocycles containing a 3-azabicyclo[3.3.1]nonane fragment, compounds with various types of biological activity were found: analgesic and anti-inflammatory, antimicrobial and fungicidal, anti-cancer, antioxidant, etc. We synthesized a number of new derivatives of 3-azabicyclo[3.3. 1] nonane by Mannich condensation of hydride σ-adduct 2-chloro-N-(2-hydroxy-3,5-dinitrophenyl)acetamide with formaldehyde and primary amines or amino acids. The synthesis was carried out in two stages. In the first stage, under the action of sodium tetrahydride borate on a solution of 2-chloro-N-(2-hydroxy-3,5-dinitrophenyl)acetamide, the C=C bonds of the aromatic ring were reduced to form a 3-charge hydride adduct. The resulting diaduct was isolated from the solution and, while cooling with ice, was introduced into Mannich condensation with formaldehyde and a solution of the primary amine or amino acid. When the reaction mixture was acidified with dilute orthophosphoric acid to pH 4-5, precipitates of the target products precipitated. After recrystallization from ethanol, the yield of the target products, depending on the substituent at the nitrogen atom, was 75-90%. This method is distinguished by relative simplicity, availability of reagents and allows under mild conditions to transfer from the aromatic system activated by nitro groups to 3-azabicyclo[3.3.1]nonane derivatives, containing promising from the point of view of further functionalization nitro, carbonyl, amino groups, and also halogen atom . The structure of the compounds obtained was proved by IR, 1H-, 13C-, two-dimensional correlation NMR spectroscopy, as well as high-resolution mass spectrometry data (HRMS).
    Type of Medium: Online Resource
    ISSN: 2074-0212 , 2074-0948
    Uniform Title: Синтез и строение новых производных 2-хлор-N-(3-R-1,5-динитро-8-оксо-3-азабицикло[3.3.1]нон-6-ен-7-ил)ацетамидов
    Language: Unknown
    Publisher: Innovation Publishing House Butlerov Heritage Ltd
    Publication Date: 2019
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  • 2
    In: Butlerov Communications, Innovation Publishing House Butlerov Heritage Ltd, Vol. 57, No. 3 ( 2019-03-31), p. 133-138
    Abstract: The present work is devoted to the study of the biological activity of benzoxazole, 5-nitrobenzoxazole and 5,7-dinitrobenzoxazole in relation to tomato plants. The ability of these substances to stimulate growth processes in tomato seeds, to influence the synthesis of mono- and polysaccharides, to regulate the content of ascorbic acid and the total acidity in the fruits of tomatoes has been studied. The ability of plants to accumulate nitrogen in the nitrate form under the action of benzoxazole and its nitro derivatives has also been analyzed. Thus, the possibility of improving the sowing properties and chemical characteristics of tomato plants by treating them with compounds of the benzoxazole group was studied. In addition, an assessment of the toxicity of the studied drugs was carried out using the computer program GUSAR on-line. Predictions of bioaccumulation factor (BCF) and endotoxicity class for rats were obtained for four forms of drug administration in animals. Earlier, the authors of the article carried out studies of the fungistatism of the considered compounds in vitro on six pathogenic fungi of various taxonomic classes. The germination of tomato seeds treated with the tested drugs was determined in the laboratory on the 12th day of the experiment by counting the germinated seeds. The germination values are expressed as a percentage of the total number of seeds sown. Growing tomato plants and harvesting was carried out in open ground conditions. Plants were treated with benzoxazole and its nitro derivatives by watering with solutions with a concentration of 0.05 mol / l. Control plants were watered. Chemical analysis of tomato fruits was performed under laboratory conditions in accordance with GOST. The analysis of the obtained data showed that the introduction of nitro groups into the basic structure of benzoxazole is accompanied by a significant increase in the biological activity of the synthesized compounds, which has different patterns of manifestation depending on the stage of plant development. Thus, 5,7-dinitrobenzoxazole has the greatest stimulating effect on the growth processes in tomato seeds. While the most pronounced positive effect on the synthesis in the fruits of tomato sugars and ascorbic acid was 5-nitrobenzoxazole. For unsubstituted benzoxazole, no pronounced positive trends in the manifestation of biological activity have been identified. Evaluation forecast using the computer program GUSAR on-line allowed to establish a low level of toxicity of the studied substances. This work is part of the study of the biological activity of various classes of organic compounds. The effect of the test substance on the growth rate and development of agricultural plants, their chemical composition is analyzed. In addition, the fungicidal activity of these compounds is determined. Thus, the purpose of the research is the selection of substances capable of comprehensively solving the problem of obtaining and preserving the yield of crop production.
    Type of Medium: Online Resource
    ISSN: 2074-0212 , 2074-0948
    Uniform Title: Влияние бензоксазола и его нитропроизводных на показатели роста и химический состав плодов томатов
    Language: Unknown
    Publisher: Innovation Publishing House Butlerov Heritage Ltd
    Publication Date: 2019
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  • 3
    Online Resource
    Online Resource
    Science and Innovation Center ; 2021
    In:  Siberian Journal of Life Sciences and Agriculture Vol. 13, No. 5 ( 2021-10-29), p. 307-320
    In: Siberian Journal of Life Sciences and Agriculture, Science and Innovation Center, Vol. 13, No. 5 ( 2021-10-29), p. 307-320
    Abstract: ackground. The problem of finding new effective fungicides for agriculture remains an urgent task of modern agrochemistry. The problem is exacerbated by the fact that, on the one hand, over the years, there has been an ever wider spread of fungi-phytopathogens, due to the intensification of agricultural production, and, on the other hand, there is an increase in the resistance of pathogens of fungal diseases to the available fungicides. This study is devoted to the study of the fungicidal activity of new derivatives of 3,7-diazabicyclo[3.3.1]nonane – 7-R-1,5-dinitro-3,7-diazabicyclo[3.3.1] nonan-2-ones. It is known that 3,7-diazabicyclononane derivatives have versatile biological activity, including showing antibacterial and fungicidal action. Previously obtained 7-R-1,5-dinitro-3,7-diazabicyclo[3.3.1]nonan-2-ones were studied for the manifestation of fungicidal activity in vitro in relation to phytopathogenic fungi of various taxonomic classes, which are the main cause diseases of agricultural crops. Purpose. To investigate the fungicidal activity of new derivatives of 7-R-1,5-dinitro-3,7-diazabicyclo[3.3.1]nonan-2-ones on various phytopathogenic fungi, causative agents of the main fungal diseases of agricultural plants. Materials and methods. The synthesized compounds were tested in vitro for fungicidal activity against seven fungi-phytopathogens of various taxonomic classes: V. inaequalis is the causative agent of apple scab, F. moniliforme is the main cause of fusarium diseases of cereal crops, R. solani is the causative agent of rhizoctonia, F. oxysporum, B sorokiniana - cause root rot, S. sclerotiorum is the causative agent of white rot, and P. ostreatus is the causative agent of tree stem rot. To determine the radial growth of mycelium, the fungal cultures were inoculated in agar nutrient medium with the addition of the test substance. The effective concentration of the drug in the sample was 30 mg/l. The suppression of fungal mycelium growth was calculated as a percentage using the Abbott`s formula. Measurements were carried out on the 3rd day. Commercial fungicides were selected as a comparison standard from the list of drugs presented in the State Catalog of Pesticides and Agrochemicals permitted for use on the territory of the Russian Federation. Results. Most of the studied substances exhibit fungicidal activity. Some compounds have a pronounced fungicidal activity comparable to Russian commercial fungicides. Conclusion. Thus, when studying the fungicidal activity of new 3,7-diazabicyclo[3.3.1]nonanes (bispidines) – 7-R-1,5-dinitro-3,7-diazabicyclo[3.3.1] nonan-2-ones on various fungi-phytopathogens, it was shown that some of the obtained compounds have pronounced fungicidal activity and are promising for further testing.
    Type of Medium: Online Resource
    ISSN: 2658-6657 , 2658-6649
    Language: Unknown
    Publisher: Science and Innovation Center
    Publication Date: 2021
    detail.hit.zdb_id: 3063887-2
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  • 4
    Online Resource
    Online Resource
    Science and Innovation Center ; 2022
    In:  Siberian Journal of Life Sciences and Agriculture Vol. 14, No. 6 ( 2022-12-25), p. 388-403
    In: Siberian Journal of Life Sciences and Agriculture, Science and Innovation Center, Vol. 14, No. 6 ( 2022-12-25), p. 388-403
    Abstract: Background. Anthropogenic impact on agricultural areas leads to pollution of environmental objects, as well as to an increase in the resistance of pathogens to modern means of protection. One of the ways to solve these problems is the development of new drugs based on colloidal solutions of metals synthesized by the “green synthesis” method using aqueous extracts of medicinal plants from central Russia. The biological activity of metal nanoparticles obtained using plant extracts is currently being actively studied in relation to various biological objects. It is advisable to study the effect of iron colloids obtained with the help of an aqueous extract of the common mantle on the growth and development of wheat plants, as well as on phytopathogen fungi, the causative agents of the main diseases of agricultural plants. Purpose. To study the biological activity of iron colloids synthesized on the basis of aqueous extracts of the common cuff. To establish the effect of iron nanoparticles on the growth and development of wheat plants, and to study the fungicidal effect of colloids on pathogenic fungi. Materials and methods. Iron colloids were obtained from plant extracts of various dilutions and iron salt solution. The content of sugars, tannins and dyes, photosynthetic pigments, vegetable protein, flavonoids and ascorbic acid was determined in the composition of the common cuff. The influence of iron colloids on the growth and development of agricultural plants was studied by analyzing the seed germination energy and biometric parameters of wheat germs treated with initial extracts and synthesized colloids. The fungicidal activity of common mantle extracts and iron colloids synthesized on their basis was studied in vitro on the following fungi – phytopathogens: F. moniliforme and F. oxysporum, V. inaequalis, R. solani, B. sorokiniana, P. ostreatus and A. alternata. Results. Growth-stimulating activity is exhibited by aqueous extracts of the common cuff of an average degree of dilution and iron colloids synthesized on their basis. Only extracts of the common cuff have fungistatic properties in relation to the fungus B. sorokiniana. Conclusion. Biological activity is shown by extracts of medium dilution and colloids synthesized on their basis. In further research on this topic, it is advisable to study the effect of various variations in salt and extract concentrations on the manifestation of fungicidal and growth-stimulating activity.
    Type of Medium: Online Resource
    ISSN: 2658-6657 , 2658-6649
    Language: Unknown
    Publisher: Science and Innovation Center
    Publication Date: 2022
    detail.hit.zdb_id: 3063887-2
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  • 5
    Online Resource
    Online Resource
    Science and Innovation Center ; 2021
    In:  Siberian Journal of Life Sciences and Agriculture Vol. 13, No. 6 ( 2021-12-30), p. 201-216
    In: Siberian Journal of Life Sciences and Agriculture, Science and Innovation Center, Vol. 13, No. 6 ( 2021-12-30), p. 201-216
    Abstract: Background. The problem of the synthesis of new effective biologically active compounds remains an urgent task of modern chemical science. It is known that oxazole derivatives have a broad spectrum of physiological activity. In this regard, expanding the range of these derivatives seems to be an urgent task. One of the promising methods for the functionalization of nitro derivatives of heterocycles is reductive activation, which proceeds through the formation of relatively labile, highly reactive hydride σ-adducts, which can then be used to synthesize new biologically active compounds. This work is devoted to the study of the formation reaction of anionic σ-complexes of 2-R-5,7-dinitrobenzoxazoles under the action of sodium tetrahydroborate. Purpose. To study the reaction of formation of anionic σ-complexes of 2-R-5,7-dinitrobenzoxazoles by spectral methods. Materials and methods. The reaction mechanism for the formation of anionic σ-adducts 2-R-5,7-dinitrobenzoxazoles under the action of sodium tetrahydroborate was proposed on the basis of the data of UV spectra obtained by carrying out the studied reaction in the cuvette of an SF 103 spectrophotometer. The structure of the obtained compounds was also proved using 1H-, 13C - and 2D-correlation NMR spectroscopy. Results. Double-charged hydride σ-adducts based on 2-R-5,7-dinitrobenzoxazoles were synthesized under the action of sodium tetrahydroborate. The structure of the formed adducts was proved by the methods of electronic and NMR spectroscopy, and a probable mechanism of the reaction was proposed. Conclusion. The reaction of mild reduction of dinitro derivatives of benzo[d]oxazole under the action of sodium tetrahydroborate was studied. As a result, the corresponding hydride σ-complexes, which are sodium salts of bis-nitroic acids of benzo[d] oxazole, were isolated and identified by spectral methods. The mechanism of the reaction of their formation has been suggested.
    Type of Medium: Online Resource
    ISSN: 2658-6657 , 2658-6649
    Language: Unknown
    Publisher: Science and Innovation Center
    Publication Date: 2021
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  • 6
    Online Resource
    Online Resource
    Science and Innovation Center ; 2023
    In:  Siberian Journal of Life Sciences and Agriculture Vol. 15, No. 1 ( 2023-02-28), p. 378-401
    In: Siberian Journal of Life Sciences and Agriculture, Science and Innovation Center, Vol. 15, No. 1 ( 2023-02-28), p. 378-401
    Abstract: Background. Pyridines are one of the most common heterocycles, the derivatives of which are widely used in pharmaceuticals, agrochemistry, and also in the production of new materials. Therefore, a comprehensive study of the chemical behavior of various pyridine derivatives will continue to be an urgent task of organic chemistry. This literature review is devoted to the systematization and analysis of the chemical properties of pyridine nitro derivatives, starting from the first half of the 20th century and up to the present. The paper considers both reactions proceeding through the nitro group (reduction under the action of various chemical agents, substitution, condensation) and reactions through the pyridine cycle. The main areas of application of nitropyridines are also shown. Purpose. Generalize and systematize the main types of reactions characteristic of nitropyridines, show the features of their chemical properties associated with the transformation of the nitro group, its effect on the mobility of substituents in the pyridine ring, as well as on the activity of the heterocycle as a whole. Materials and methods. To achieve the goal of the study, a review of the scientific literature was made on the main types of chemical reactions characteristic of pyridine nitro derivatives and the most significant areas of their application. Results. This paper summarizes the results of experimental studies on the chemical properties and application of nitropyridines from the beginning of the last century to the present. Conclusion. Thus, as a result of the analysis of sources devoted to the chemical properties and application of nitropyridines, a brief literature review was compiled, including the main types of reactions characteristic of the compounds under study, and their main areas of application were identified.
    Type of Medium: Online Resource
    ISSN: 2658-6657 , 2658-6649
    Language: Unknown
    Publisher: Science and Innovation Center
    Publication Date: 2023
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  • 7
    In: Butlerov Communications, Innovation Publishing House Butlerov Heritage Ltd, Vol. 58, No. 5 ( 2019-05-31), p. 32-38
    Abstract: In this paper, we studied the effect of anionic adducts of 5,7-dinitrobenz[d]oxazole on the sowing properties of wheat seeds (germination energy and germination), the growth rate of wheat shoots, amylase activity in the roots and shoots of wheat. The evaluation of the toxicity of the tested compounds was carried out using the GUSAR on-line computer program. A prediction was made of bioaccumulation factor (BCF), the average lethal concentration for daphnia and minnow (LD50), the concentration of half-maximal growth inhibition (IGC50) and the acute toxicity indicators (LD50) for rats with different routes of administration. For the study were selected: 2-methoxy-5,7-dinitro-2 (piperidin-1-yl)-2,3-dihydrobenzo[d] oxazole, 2-methoxy-5,7-dinitro-1,2-dihydrobenzo[d]sodium oxazolide, 2-methyl-2-methoxy-5,7-dinitro-1,2-dihydro-benzo[d] cesium oxazolide, 2-phenyl-2-methoxy-5,7-dinitro-1,2-dihydrobenzo[d]sodium oxazolide and 2-methyl-2-ethoxy-5,7-dinitro-1,2-dihydrobenzo[d] oxazolid cesium. Biological activity was analyzed on wheat seeds of the winter variety Moskovskaya 39. Aqueous solutions of the studied substances were used with concentrations: 1·10-4 mol/l, 1·10-6 mol / l, 1·10-8 mol/l, 1·10-10 mol/l, 1·10-12 mol/l and 1·10-14 mol/l. The germination energy of wheat seeds was determined on day 3, and germination on the 9th day after sowing by counting germinated seeds. Values are expressed as a percentage of the total number of seeds sown. Biometric indicators (height of shoots) were determined on the 9th day after sowing. Amylase activity was measured in the roots and shoots of wheat plants by the amount of undecomposed starch using spectrophotometry. The data obtained allow us to conclude that different substituents in the anionic adducts of 5,7-dinitrobenz[d]oxazole in varying degrees contribute to the manifestation of biological activity at different stages of wheat plant growth. During the first three days, 2-methyl-2-ethoxy-5,7-dinitro-1,2-dihydrobenzo [d] oxazolid cesium affects the growth processes in wheat seeds most actively. The growth of wheat shoots is stimulated to a greater extent by solutions of 2-methoxy-5,7-dinitro-1,2-dihydrobenzo[d]oxazolid sodium with concentrations of 1·10–4 and 1·10–6 mol/l and solution 2-phenyl-2-methoxy-5,7-dinitro-1,2-dihydroben-zo[d] oxazolid sodium with a concentration of 1·10-8 mol/l. Amylase activity in wheat roots is increased by solutions of 2-methyl-2-methoxy-5,7-dinitro-1,2-dihydrobenzo[d]cesium oxazolid in the whole range of concentrations used, and in the shoots – solutions of 2-methoxy-5,7-dinitro-1,2-dihydrobenzo[d] oxazolid sodium in the range of all tested concentrations. In general, anionic adducts of 5,7-dinitrobenz[d]oxazole exhibit high biological activity in relation to wheat plants in the early stages of development.
    Type of Medium: Online Resource
    ISSN: 2074-0212 , 2074-0948
    Uniform Title: Изучение биологической активности анионных аддуктов 5,7-динитробенз[d]оксазола
    Language: Unknown
    Publisher: Innovation Publishing House Butlerov Heritage Ltd
    Publication Date: 2019
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  • 8
    In: Butlerov Communications, Innovation Publishing House Butlerov Heritage Ltd, Vol. 57, No. 2 ( 2019-02-28), p. 85-89
    Abstract: Growing crops is one of the priority state programs. For agriculture, this is due to the difficulties associated with unstable climatic conditions, low levels of anthropogenic pollution of the environment. Therefore, to increase the yield and improve the quality of crops, substances with regulatory properties are used. It is extremely difficult to obtain yields on an industrial scale, without using growth regulators that promote growth, enhance the immune system of plants and increase their resistance to stress. This study is part of a great work on the study of the biological activity of various classes of compounds. The effect of the tested substances on the growth rate and development of agricultural plants, their chemical composition is analyzed. In addition, the fungicidal activity of these compounds is determined. Thus, the task is to solve the problem of obtaining and preserving the crop yield of crop production. For the study of biological activity were selected compounds: 2-methyl-5-nitrobenzoxazole, 2-methyl-5,7-dinitrobenzoxazole, 2-phenyl-5,7-dinitrobenzoxazole. The analytes were tested for biological activity against wheat seeds and plants. The effect of substances on the universe and the seed germination energy, plant growth rate, and cell and carotene synthesis were studied. In addition, it was determined the effect of processing compounds in a given mass of wheat plants. Experienced seeds and wheat plants were treated with solutions of 2-methyl-5-nitrobenzoxazole, 2-methyl-5,7-dinitrobenzoxazole, 2-phenyl-5,7-dinitrobenzoxazole, the control plants were watered with water. The research results show that 2-methyl-5,7-dinitrobenzoxazole has the greatest influence on the growth rate and synthesis of substances in the mass of wheat plants. This leads to an increase in the number of all kinds of seeds by 42.2%, biometric growth rates by 17.15%, root mass by 30.8%, carotene content by 74.45%, compared to control plants.
    Type of Medium: Online Resource
    ISSN: 2074-0212 , 2074-0948
    Uniform Title: Исследование биологической активности 2-метил-5-нитробензоксазола и его динитропроизводных
    Language: Unknown
    Publisher: Innovation Publishing House Butlerov Heritage Ltd
    Publication Date: 2019
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  • 9
    In: Siberian Journal of Life Sciences and Agriculture, Science and Innovation Center, Vol. 14, No. 6 ( 2022-12-25), p. 372-387
    Abstract: Background. The problem of finding new effective plant protection products remains an urgent task of modern agrochemistry. It is known that tetrahydropyridine derivatives exhibit a broad spectrum of biological activity, including fungicidal activity. However, compounds with potential biological activity can also be highly toxic to humans, cultivated crops, and the environment as a whole, so it is necessary to study their environmental safety. The content of photosynthetic pigments and ascorbic acid are one of the most important biochemical indicators of plant response to environmental stress factors, therefore, determining their amount helps to assessthe physiological state of plants and analyze the toxicity of the synthesized compounds. Purpose. To study the effect of new 6-R-3,5-dinitro-1,2,3,4-tetrahydropyridines on the content of photosynthetic pigments and ascorbic acid in plant tissues in order to assess the safety of their use as potential plant protection products. Materials and methods. The test compounds were obtained by the previously developed method for the selective reduction of 2-R-3,5-dinitropyridines. Winter wheat seeds of the Moskovskaya 39 variety were germinated in Petri dishes using solutions of the synthesized substances. Seeds germinated in water were used as controls. On the ninth day, the content of various groups of photosynthetic pigments (chlorophylls a, b, carotenoids), as well as ascorbic acid in plant tissues was determined. All experiments were carried out in triplicate. In addition, the analytes were tested for toxicity using the GUSAR Environmental Toxicity software. Results. The effect of new derivatives of tetrahydropyridine on the accumulation of photosynthetic pigments and ascorbic acid in plant tissues of winter wheat was studied. It was shown that the studied compounds do not have a significant toxic effect on plants. Conclusion. As a result of studying the effect of new 6-R-3,5-dinitro-1,2,3,4-tetrahydropyridines on the content of photosynthetic pigments and ascorbic acid, as well as in silico computer prediction in GUSAR Environmental Toxicity, it was found that, in general, the studied compounds are relatively safe and, therefore, promising for further testing as biologically active plant protection products.
    Type of Medium: Online Resource
    ISSN: 2658-6657 , 2658-6649
    Language: Unknown
    Publisher: Science and Innovation Center
    Publication Date: 2022
    detail.hit.zdb_id: 3063887-2
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  • 10
    In: Butlerov Communications, Innovation Publishing House Butlerov Heritage Ltd, Vol. 59, No. 8 ( 2019-08-31), p. 40-46
    Abstract: The aim of the work was quantum chemical modeling by the theory of the functional density functional of the interaction of 2-methyl-5,7-dinitrobenzo[d]oxazole with tetrahydride borate ion. For this, geometric optimization and calculation of the total energies of the 2-methyl-5,7-dinitrobenzo[d] oxazole molecule in the gas phase and water were carried out using the DFT/B3LYP/aug-cc-pVDZ method. To determine the likely reaction centers for a nucleophile attack, atomic charges according to Mulliken and NBO charges in the molecule of the initial substrate were established. The largest positive charges according to Mulliken in the studied molecule, both in the gas phase and in water, are concentrated on the carbon atoms C4 and C6, whereas in the case of NBO analysis, such is the carbon atom C2. Analysis of nucleophilic atomic frontal electron densities on the atoms of the substrate showed that from the point of view of orbital control, the attachment of a nucleophile is most likely to the carbon atom in the 4 position. The data obtained are consistent with previous experimental studies in which a rigid base – methoxide ion is attached to a carbon atom C2, which is a rigid acid reaction center, and a reaction with a soft base – tetrahydride borate ion proceeds along softer acid centers – carbon atoms C4 and C6 of the benzene ring. The calculation of the total energies of the proposed -adducts allowed us to establish that the most thermodynamically stable structure when one hydride ion is attached to the 2-methyl-5,7-dinitrobenzo[d]oxazole molecule is the product of nucleophile addition to the C4 carbon atom, and in the case of two hydride ions – at positions 4 and 6 of the annelated benzene ring activated by nitro groups. Thus, the calculation of the Mulliken charges, as well as the values of the nucleophilic atomic frontal electron densities at the atoms of the substrate, best reflects the course of the reaction under conditions of orbital control with a tetrahydroborate ion, and NBO charges are better suited to describe the course of the reaction under conditions of charge control.
    Type of Medium: Online Resource
    ISSN: 2074-0212 , 2074-0948
    Uniform Title: Квантово-химическое моделирование взаимодействия 2-метил-5,7-динитробензо[d]оксазола с тетрагидридоборат-ионом методом DFT
    Language: Unknown
    Publisher: Innovation Publishing House Butlerov Heritage Ltd
    Publication Date: 2019
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