CC BY
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УДК 665.635
https://doi.org/10.24412/2310-8266-2022-4-19-24
QUANTUM CHEMICAL CALCULATIONS AS A METHOD TO PREDICT THE DEPENDENCE OF PROPERTIES ON STRUCTURE
Aleksanyan Karina G.1, Shamsutdinova Larisa P.2, Cheban Edeuard G.1, Aleksanyan David R.3, Agadzhanian Sona A.4
1 Gubkin Russian State University of Oil and Gas (National Research University), 119991, Moscow, Russia ORCID: https://orcid.org/0000-0001-9846-4572, Email: alkarine@mail.ru
ORCID: https://orcid.org/0000-0002-49475-5874, Email: eduard.cheban1001@mail.ru
2 Kazan National Research Technological University, 420015, Kazan, Russia ORCID: https://orcid.org/0000-0003-4701-1869, Email: larisasham@mail.ru
3 Skolkovo Innovation Center, 121205, Moscow, Russia
ORCID: https://orcid.org/0000-0002-4776-6228, Email: david_alex92@mail.ru
4 Lomonosov Moscow State University, 119991, Moscow, Russia ORCID: https://orcid.org/0000-0002-9475-5847, Email: sona_1990@mail.ru
Abstract: One of the most important properties of fuels and lubricants is their resistance to oxidation during long-term storage and operation at high temperatures. The quality of the oil deteriorates most severely when it is decomposed by oxygen, high temperatures and metal surfaces containing non-ferrous metals that act as oxidation catalysts. The article presents the proposed mechanism of action of additives in fuel. Today there is a tendency to produce engines that operate at higher temperatures and it should be expected that the content of antioxidant additives will increase, and those that can withstand high temperatures will be used. An analysis of the world literature over the past 30 years has shown that in the process of creating effective additives for fuels and oils, the possibility of using numerous organic compounds for this purpose has been investigated. It is no exaggeration to say that practically all classes of organic compounds containing various functional groups have been studied as additives. Phenolic additives and alkylphenol isomers are used as an effective antioxidant additive to fuels and oils. A structurally similar series of microwave frequencies was synthesized, their antioxidant activity was studied, and then quantum chemical calculations of the structures were carried out to identify the dependence of their activity on certain parameters. The possibility of software packages for quantum chemical calculations of sterically hindered phenols (HHF) is investigated and the dependence of antioxidant activity on various parameters of the phenol structure is determined. Methods of their modification in a substance of the class of spatially hindered phenols (PPF) were found, arylamines and Schiff bases were obtained on their basis. The resulting compounds exhibit high antioxidant activity. Keywords: spatially hindered phenols, antioxidant additives, quantum chemical calculations, correlation, forecasting. For citation: Aleksanyan K.G., Shamsutdinova L.P., Cheban E.G., Aleksanyan D.R., Agadzhanian S.A. QUANTUM CHEMICAL CALCULATIONS AS A METHOD TO PREDICT THE DEPENDENCE OF PROPERTIES ON STRUCTURE. Oil & Gas Chemistry. 2022, no. 4, pp. 19-24. DOI:10.24412/2310-8266-2022-4-19-24
КВАНТОВО-ХИМИЧЕСКИЕ РАСЧЕТЫ КАК МЕТОД ПРЕДСКАЗАНИЯ ЗАВИСИМОСТИ СВОЙСТВ ОТ СТРУКТУРЫ
Алексанян К.Г.1, Шамсутдинова Л.П.2, Чебан Е.Г.1, Алексанян Д.Р.3, Агаджанян С.А.4
1 Российский государственный университет нефти и газа (НИУ) им. И.М. Губкина, 119991, Москва, Россия ORCID: https://orcid.org/0000-0001-9846-4572, Email: alkarine@mail.ru
ORCID: https://orcid.org/0000-0002-49475-5874, Email: eduard.cheban1001@mail.ru
2 Казанский национальный исследовательский технологический университет, 420015, Казань, Россия ORCID: https://orcid.org/0000-0003-4701-1869, Email: larisasham@mail.ru
3 Инновационный центр «Сколково», 121205, Москва, Россия
ORCID: https://orcid.org/0000-0002-4776-6228, Email: david_alex92@mail.ru
4 Московский государственный университет имени М.В. Ломоносова, 119991, Москва, Россия ORCID: https://orcid.org/0000-0002-9475-5847, Email: sona_1990@mail.ru
Резюме: В статье приведен предполагаемый механизм действия присадок в топливе. Был синтезирован структурно подобный ряд алкилфенолов, изучена их антиоксидантная активность, а затем проведены квантово-химические расчеты структур для выявления зависимости их активности от определенных параметров. Исследована возможность программных пакетов для квантово-химических расчетов стерически затрудненных фенолов (HHF) и определена зависимость антиоксидантной активности от различных параметров структуры фенола. Найдены способы их модификации в веществе класса пространственно-затрудненных фенолов (ПЗФ), на их основе получены ариламины и основания Шиффа. Определено, что полученые соединения проявляют высокую антиокислительную активность.
Ключевые слова: пространственно затрудненные фенолы, антиокислительные присадки, квантово-химические расчеты, корреляция, прогнозирование.
Для цитирования: Алексанян К.Г., Шамсутдинова Л.П., Чебан Е.Г., Алексанян Д.Р., Агаджанян С.А. Квантово-химические расчеты как метод предсказания зависимости свойств от структуры // НефтеГазоХимия. 2022. № 4. С. 19-24. DOI:10.24412/2310-8266-2022-4-19-24
НефтеГазоХимия 19
1. Introduction
The composition of mineral oils can be very diverse, depending on the raw material from which the oil was produced. All mineral oils contain paraffinic, naphthenic and aromatic hydrocarbons, as well as heteroatomic derivatives. All types of oils undergo profound chemical transformations during the operation of the unit, such as: oxidation, alkylation, decomposition, polymerization, etc. The products of these transformations settle on the parts of the device, hindering its normal work. At the same time, it accelerates the wear and tear of its parts andthe reduction of power. Moreover, the parts are corroded by the lubricant.
Presently, there is a tendency to toughen the operating mode of engines: the temperature and pressure in the combustion chamber increase, therefore, the average temperature of the engine oil in the engine also grows. Thus, the synthesis of new additives capable of operating at higher temperatures, above 90-100 °C, is a topical issue [1].
Until recently, predicting the properties of an organic substance using some theoretical calculations seemed impossible. The development of science and technology, including information technology, is progressing rapidly [2]. So, the rapid development of computers in the 90th was followed by the emergence of various computational methods of calculation in quantum chemistry [3-4], which significantly expanded researchers' ability to assess various properties of chemical compounds. It helps to make the investigation less time-consuming and challenging. As evidence of the efficiency and convenience of using quantum chemical calculations, one can mention the discovery and synthesis of fullerenes, which was preceded by quantum chemical calculations, thanks to which the possibility of their synthesis and specific properties were predicted [5-7].
So far, quantum chemical methods have become one of the most important tools in chemical research. It is also important to emphasize that the role of these methods in various studies is growing from year to year. The development of computer technologies and quantum-chemical research has achieved such high results ¡g^^ that they can rank with experimental research. At the same time, they can provide a wider range of information.
W. Heisenberg, who 1925-1927 developed the matrix version of quantum mechanics in 1925-1927 [8], said that these were delightful times when everyone thought that the key to all the secrets of the universe had been found, and it was necessary to put it to use carefully and gradually.
However, the nature turned out to be much more complicated than a person might have thought. It soon became clear that the precise solution of the molecular Schrodinger equation causes significant difficulties associated with the computational capabilities of the equipment, even for the simplest system of the H2+ ion [2].
In 1931, E. Huckel succeeded in developing a method for calculating p-electron systems, which was only the first serious step on a long path in the evolution of quantum-chemical calculation methods [8]. This method was extremely simple, therefore, it was
used (slightly modified) until the mid-70s, since no one could come up with anything more advanced. In 1963, R. Hoffman proposed a version of Huckel with an extended basis, which has been used from then on [8-10].
The aim of this work is to search for relationships in the structure-property system with the use of quantum-chemical calculations, with proofs based on fine organic synthesis and testing as antioxidant additives.
The objects of research are a series of synthesized sterically hindered phenols with various radicals in the vapor position.
2. Results and discussion
A number of sterically hindered phenols (SHF) have been obtained in order to plot dependency curves of antioxidant activity on quantum-chemical parameters of these phenols.
Initial phosphorylated 4-methylene-2,6-di-tert-butylcyclo-hexadiene-2,5-ones (phosphorylated methylenquinones) (fig. 1) were synthesized by oxidation of the corresponding phosphorylated sterically hindered phenols by potassium ferricyanide in alkaline environment [9].
The synthesis of 1,3-bis-(4-hydroxy-3,5-di-tert-butylphenyl)-3-dimethoxy-phosphoryl-2-tiapropan-1-diphenylphosphinoxide (fig. 2) has been carried out by addition of O, O-dimethyl-[(4-hydroxy-3,5-di-tert butylphenyl) mercaptomethyl] phosphonate to the phosphorylated methylenquinone [10, 11]
We have also carried out an acetonylation reaction of phosphorylated methylenquinones in the presence of dimethylamine as the base. The interaction occurs when solutions of phosphorylated methylenquinone and acetone are boiled with 33% aqueous solution of dimethylamine, which leads to the formation of 4-hydroxy-3,5-di-tert-butylphenyl) (2-oxopropyl)metandyethylphosphinoxide (fig. 3) with 90% yield [12].
Diphosforylated [(4-hydroxy-3,5-di-tert-butylphenyl)
(dietoxyphosphoryl)methane] (fig. 4) diphenylphosphinoxide (4) has been obtained by interaction of (4-hydroxy-3,5-
The synthesis of 4-methylene-2,6-di-tert-butylcyclohexadi-ene-2,5-ones (phosphory lated methyl enquinones)
The synthesis of 1,3-bis-(4-hydroxy-3,5-di-tert-butylphenyl)-3-dimeth-oxy-phosphoryl-2-tiapropan-1-diphenylphosphinoxide
Fig. 3
The synthesis of 4-hydroxy-3,5-di-tert-butylphenyl) (2-oxopropyl)metandyethylphosphinoxide
Fig. 4
The synthesis of Diphosforylated [(4-hydroxy-3,5-di-tert-butylphe-nyl)(dietoxyphosphoryl)-methane] diphenylphosphinoxide
Fig. 5
The synthesis of Diethyl(3,5-di-tert-butyl-4-hydroxy-phenyl)(methoxymethyl)phosphonate
Fig. 6
The synthesis of 2.6-di-tert-butyl-4-dimethylamine-methylphenol
di-tert-butylphenyl acetonylation)
chlorometandiphenyl-phosphinoxide and triethylphosphite [13].
Diethyl(3,5-di-tert-butyl-4-hydroxyphenyl)(methoxymethyl) phosphonate (fig. 5) has been obtained by interaction of phosphorylated methylenquinone with methanol in the presence of catalytic amounts of hydrochloric acid.
For comparison, we have synthesized 2.6-di-tert-butyl-4-dimethylamine-methylphenol (fig. 6), industrial antioxidant Agidol-3 [14-17].
A quantum-chemical calculation of the studied compounds has been performed to predict the dependence of antioxidant properties on the structure of the compound. Results are presented in table 1.
Calculations were performed in Gaussian and MOPAC mathematical packages by PM7 method.Further on, we have carried out a quantum-chemical calculation of the structure of each compound andstablished relationships between the calculated parameters and the actual compound's activity. The antioxidant activity of the above compounds (additive's concentration in oil was 0.1% by mass) has been tested by determining acid number (AN) of the oxidized I-20 oil with the use of Petrotest device at 150 Celsius for 8 hours with continuous air flow in accordance with GOST 5985-79. Results of AN determination of the tested samples are given in table 2.
Table 2 shows acid numbers of oils containing the tested compounds after the oxidation has been completed. The acid number value of oil after the test shows its resistance to oxidation. Obviously, the effects that the studied compounds render on oil resistance to oxidation are different.
According to data of Tables 1 and 2 we have further on plotted the dependencies revealing the correlation between the antioxidant activity of the studied SHF and the calculated parameters of the investigated structures.
The dependence of acid numbers of oxidized oils with additives determined according to GOST 5985-79 on some pre-calculated quantum-chemical parameters are shown below (fig. 7-11).
By constructing dependencies between acid numbers of oxidized samples with compounds dissolved therein and calculated parameters, we have carried out the research to reveal the dependencies in the explicit form. The corresponding dependencies are presented below (fig. 7-18).
НефтеГазоХимия 21
Results of calculations of the studied compounds
п\п Bond length of O-H, A Valenceangle С-О-Н,0 Ionization potential, eV Total energy, eV HOMO energy, eV LUMO energy, eV Combination heat, kcal/mole Dipole moment Entalphy (Т=298К), kcal/mole Formation entropy, kcal/ mole *К (Т=298К) Gibbs energy (Т=298К)
1 1,001 112,209 8,143 -5696,685 -8,143 -0,189 -66,172 5,951 20026,302 188,590 -36173,399
2 1,002 112,233 8,133 -8517,033 -8,133 -0,257 -297,205 1,784 29975,014 258,288 -46994,929
3 1,002 112,187 8,568 -4265,873 -8,568 0,054 -204,549 6,121 16887,721 169,854 -33728,831
4 1,002 112,195 8,314 -5613,900 -8,314 -0,175 -164,658 8,414 20857,770 196,309 -37642,193
5 1,003 112,250 8,344 -4584,400 -8,344 0,360 -304,140 2,989 15272,000 98,094 -13960,101
6 1,001 112,120 8,499 -2962,000 -8,499 0,462 -69,920 0,892 10027,000 60,170 -7903,660
Table 1
After the analysis and the relevant processing of the obtained data by exclusion from plots of the most extreme values, we arrived to curves illustrating the dependence of antioxidant activity of the tested compound on the corresponding parameter.
First of all, it should be emphasized that the first two samples have the highest acid numbers, which means that compounds dissolved in them have the lowest antioxidant activity. In most of the graphs, it was noticed that these very samples stand out the most in the entire dependence curve, and it was decided to exclude them from the plot. We assumed that these samples have a lower antioxidizing activity due to a high content of aromatic rings and the large size of the molecule itself, which slows down the movement of the molecule into the volume and, consequently, reduces its activity.
It has been also noticed that industrial compounds (Agidol-1, Agidol-3) have the lowest volume of substituents in para positions. Hence, it can be concluded that the volume of substituent has a significant effect on the antioxidant's activity.
3. Conclusion
It has been proved experimentally and clearly demonstrated that there is some correlation between the SHF activity and the calculated quantum-chemical parameters. This is evidenced by the high values of the correlation coefficients (R = 0.7-0.9).
The presence of these relationships opens up new horizons in the approach to the development of new antioxidants based on SHF. This will significantly optimize and enhance the search and development of new antioxidant compounds.
4. Experimental section
1H NMR spectra were recorded on Tesla BS-567A instruments with 100 MHz operating frequency, Bruker WP 250 with 250 MHz operating frequency, and Bruker MSL 400 with 400 MHz operating frequency, using deuterated solvent residual proton signals (CDCl3).
All solvents used were cleaned and absolutized using standard methods.
(4-Hydroxy-3,5-di-tert-butylphenyl)(2-aminophenyl) thiometandi-phenylphosphinoxide (1)
Table 2
Results of AN determination of the tested samples
Compound number Acid number
1 0,252495
2 0,218829
3 0,11222
4 0,187969
5 0,16833
6 0,05611
The solution of 0.21 g (0.0005 mole) of phosphorylated methylenquinone and 0.31 g (0.0025 mole) of 2-aminothiophenol in 10 ml of toluene was boiled for 1 hour. After cooling and filtration, 0.16 g of colorless product of (59%), was obtained, with melting point 168-170°C (isoctane toluene). Found (%): P 5.65. C33H38N02PS. Calculated (%): P 5.70.
1,3-Bis-(4-hydroxy-3,5-di-tert-butylphenyl)-3-dimethoxyphoryl-2-tiapropan-1-diphenylphosphinoxide (2)
To a solution of 0.42 g (0.001 mol) of methylenquinone phosphorylated in 5 ml of dioxane we added a solution of 0.36 g (0.001 mole) of 4-hydroxy-3.5-di-tert-butylphenyl) mercaptomethan-O,O-dimethyl-phosphonate in 5 ml of dioxane. The mixture was kept at room temperature for 24 hours. After dioxane distillation in vacuum the residue was recrystallized from isooctane-toluene (1:1) mixture. We obtained 0.38 g (48.7%) of colorless crystals, with melting point 192-195°C (isooctane toluene).
1HNMRspectrum (CDCl3), 8, ppm: 1.46 (s, 18H, CMe3), 1.59 (s, 18H, CMe3), 3.65 (d, 3H, MeO, 3JPH11.0 Hz), 3.85 (d, 3H, MeO, 3JPH11.0 Hz), 4.55 (d, 2H, PCH, PJPH12.0 Hz), 5.25 (br.s., 2H, OH), 7.06 (d, 2H, C6H2, 4JHH 2.0 Hz), 7.22 (d, 2H, C6H2, 4JHH 2.0 Hz). Found, %: C 68.02, 67.45; H 8.03, 7.96; P 7.68, 7.84. C44H60O6P2S.Calculated, %: C 67.87; H 7.71; P 7.97.
(4-Hydroxy-3,5-di-tert-butylphenyl)(2-oxopropyl) methandiethyl-phosphinoxide (3)
Thesolution of 0.96 g (0.003 mole) of phosphorylated methylenquinone, 2 ml of 33% aqueous solution of dimethylamine
Dependence of AN on О-Н bond length
Dependence of AN on С-О-Н valenceangle
Dependence of AN on IP
Dependence of AN on molecule total energy
Dependence of AN on LUMO energy
Dependence of AN on molecule combination heat
Dependence of AN on dipole moment Dependence of AN on enthalpy
Dependence of AN on entropy
AN (S)
0.30 0.25 0.20 0.15 0.10 0.05 0.00
•
•
*
*
100 150 200 250
Dependence of AN on Gibbs Energy
Dependence of AN on О-Н bond polarity
AN (O-H bond polarity)
0.30
0.25
0.20
•
0.15
0.10 / •
0.05 •
0.00
0.36 0.37 0.38 0.39 0.4 0.41 0.42 0.43 0.44
Dependence of AN energy gap (HOMO-LUMOdifference)
AN (HOMO-LUMO)
-9.2 -9 -8.8 -8.6 -8.4 -8.2 -8 -7.8 -7.6 -7.4 -7.2
neqj i ei азолимия
23
Fig. 7
Fig. 8
Fig. 9
Fig. 14
Fig. 15
Fig. 16
Fig. 17
Fig. 18
and 20 ml of acetone were kept at room temperature for 24 hours. After removal of volatile products in vacuum, the residue was treated with water. The yield of the product amounted to 1.03 g (90.4%), with melting point 123-125°C (isooctane).
1HNMRspectrum(CDCl3, 8, ppm): 0.91-2.1 (m, 10H, Et2P), 1.57 (s, 18H, 2t-Bu), 2.48 s (2H, CH2CO), 2.42 (s, 3H, MeCO), 3.41(d, 1H, CHP, 2J=10Hz), 5.41 (s, 1H,OH), 7.34 (s, 2H, C6H2). Found (%): P 8.40. C22H37O3P. Calculated (%): P 8.15.
[(4-Hydroxy-3,5-di-tert-butylphenyl)(dietoxyphosphoryl) methane]-diphenylphosphinoxide (4)
A mixture of 0.91 g (0.002 mole) of (4-hydroxy-3.5-di-tert-butylphenyl)-chlorometandiphenylphosphinoxide and 0.37 g (0.0022 mole) of triethylphosphite was kept at 120-130°C for 40 min until the active release of ethyl chloride ceased. Processing of the crystallized reaction mass with hexane resulted in 1.10 g (98%) of colorless product, with melting point 162-163°C (toluene). 1HNMRspectrum (CCl4+ CDCl3).
1HNMRspectrum(CCl4+ CDCl3), 8, ppm: 1.12 (t, 3H, CH3, 3JHH 6 Hz), 1.20 (t, 3H, CCH3, 3JHH6 Hz), 1.42 (s, 18H, C(CH3)3), 3.85-4.25 (m, 5H, OCH2, PCHP), 5.18 (s, 1H, OH), 7.10 (br.s., 2H, C6H2), 7.20-8.20 (m, 10H, C6H5). 31P NMR spectrum 8P
19.32 ppm (P-phosphine-oxide), 26.12 ppm (P-phosphonate). Found, %: P 10.50, 10.55. C31H42O5P2. Calculated, %: P 11.13.
(4-Hydroxy-3,5-di-tert-butylphenyl)(methoxy) methyldiethylphosphonate (5)
A mixture of 0.89 g (0.0025 mole) of phosphorylated methylenquinone and 7.9 g (0.25 mole) of methanol with catalytic hydrochloric acid (3 drops) was kept at room temperature for 24 hours. After distillation of volatiles, 0.80 g of colorless product (83%) were obtained, with melting point 122-123°C (hexane). Found, %: P 8.05, 7.95. C20H35O5P2. Calculated, %: P 8.01. 2.6-Di-tert-butyl-4-dimethylamine-ethylphenol (6) 2.74 g of 33% aqueous dimethylamine in 5 ml of ethanol and 1.7 g of formalin (36%) were added to the solution of 4.12 g (0.02 mole) of 2.6-di-tert-butyl phenol in 15 ml of ethanol. The reaction heat was removed with external cooling. The reaction mixture was then boiled for 3 hours. After ethanol distillation in vacuum, the residue was poured on 10 ml of water. The light yellow sediment was filtered out, washed with water and dried at room temperature for 3 days. After recrystallization, 0.5 g (95%) of colorless prismatic crystals of the product were obtained from hexane, with melting point 92-94°C [18, 19].
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ИНФОРМАЦИЯ ОБ АВТОРЕ / INFORMATION ABOUT THE AUTHOR
Aleksanyan Karina G., Cand. Sci. (Chem.), Assoc. Prof. of the Department of Organic and Petroleum Chemistry, Gubkin Russian State University of Oil and Gas (National Research University).
Shamsutdinova Larisa P., Cand. Sci. (Chem.), Assoc. Prof. of the Department of Organic Chemistry. Kazan Research Technological University. Cheban Eduard G., Student of the Department of Organic and Petroleum Chemistry, Gubkin I.M. Russian State University of Oil and Gas (National Research University. Aleksanyan David R., Cand. Sci. (Chem.), Head of the research laboratory, Skolkovo Innovation center.
Aghajanyan Sona A., Cand. Sci. (Phil.), Lecturer of the Department of English for Natural Sciences of the Faculty of Foreign Languages and Regional Studies, Lomonosov Moscow State University.
Алексанян Карина Григорьевна, к.х.н., доцент кафедры органической химии и химии нефти, РГУ нефти и газа (национальный исследовательский университет) имени И.М. Губкина.
Шамсутдинова Лариса Петровна, к.х.н., доцент кафедры органической химии, Казанский научно-исследовательский технологический университет. Чебан Эдуард Геннадиевич, студент кафедры органической химии и химии нефти, РГУ нефти и газа (национальный исследовательский университет) имени И.М. Губкина.
Алексанян Давид Робертович, к.х.н., руководитель исследовательской лаборатории, Инновационный центр «Сколково».
Агаджанян Сона Арамовна, к.фил.н., преподаватель кафедры английского языка для естественных факультетов факультета иностранных языков и реги-оноведения, МГУ имени М.В. Ломоносова.
