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Project titleTheoretical studies of non-covalent interactions in chemical systems promising for catalysis, materials science, and medicine

AffiliationFederal State Budgetary Educational Institution of Higher Education "Saint-Petersburg State University",

Research area 03 - CHEMISTRY AND MATERIAL SCIENCES, 03-203 - Chemistry of coordination compounds

Keywordscoordination chemistry, organometallic chemistry, inorganic chemistry, organic chemistry, quantum chemical calculations, computer modeling, non-covalent interactions, hydrogen bonds, halogen bonds, chalcogen bonds, metallophilic interactions, stacking, supramolecular systems, catalysis, reactivity

Annotation
Non-covalent interactions determine the existence of solids and properties of molecular systems in gas and liquid phases as well as control elementary steps of chemical reactions. Non-covalent interactions are necessary for the formation and folding of three-dimensional structure of proteins and nucleic acids. These intermolecular and intramolecular interactions have a significant effect on the dissolving powers of liquids and their boiling points, on the properties of membranes, gels and polymers. Non-covalent interactions play an important role in catalysis, medical and pharmaceutical chemistry, and materials science. Examples of such weak interactions are hydrogen, halogen, chalcogen, pnictogen, tetrel and semi-coordination bonds; agosic and anagosic interactions; stacking, anion- / cation-π interactions; metallophilic interactions. Information about intermolecular and intramolecular interactions usually obtained on the basis of X-ray analysis data, from experiments on measuring the thermophysical properties of gases, liquids and solids, on phonon spectra and on elastic characteristics of crystals, on scattering of atomic and molecular beams, by measuring the sublimation energies, spin times and spin-lattice relaxation, vibrational-rotational spectra. Unfortunately, all these experimental methods provide only indirect information and do not allow us to establish the nature of non-covalent interactions, which is the task of quantum and computational chemistry. In particular, most promising theoretical methods in this regard are: topological analysis of the electron density distribution within the framework of Bader’s theory (QTAIM); investigation of different effects of crystal packing using Hirshfeld surface analysis; analysis of natural bond orbitals and charges within the framework of Weinhold theory (NBO); analysis of charge and energy decomposition in the framework of formalisms proposed by Frenking and Morokuma (CDA and EDA, respectively). Thus, the most productive approach to the study of non-covalent interactions is a combination of experiments with recent advances in such areas of theoretical chemical science as quantum and computational chemistry. In this project, we plan to conduct a comprehensive theoretical study of non-covalent interactions (qualitative and quantitative description of this phenomenon) in various inorganic, organic, organometallic and coordination compounds and their supramolecular associates obtained in the Institute of Chemistry, St. Petersburg State University and in the laboratories of our Russian and foreign colleagues (for example, scientific groups of Prof. V. P. Fedin (A. V. Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia), Prof. Armando J.L. Pombeiro (Centro de Quimica Estrutural, Instituto Superior Tecnico, Universidade de Lisboa, Lisbon, Portugal), Prof. A. N. Kornev, (G. A. Razuvaev Institute of Organometallic Chemistry, RAS, Nizhny Novgorod, Russia), Prof. Matti Haukka (Department of Chemistry, University of Jyväskylä, Jyväskylä, Finland), Prof. Andreas Roodt (Department of Chemistry, University of the Free State, Bloomfontein, South Africa) and others) as part of collaborations supported by Russian Science Foundation, Russian Foundation for Basic Research, and other scientific foundations grants. This project is very relevant for the development of such a field of modern science as supramolecular chemistry, since our research will help to classify non-covalent interactions by type and energy characteristics. The close collaboration between the above-mentioned laboratories, which already have decades of productive work, will be further expanded, thereby stimulating the development of scientific contacts between our groups and, ultimately, an increase in publication activity. During this project, we have planned: (1) to study new types of non-covalent interactions (hydrogen, halogen, chalcogen, pnictogen, tetrel and semi-coordination bonds; agosic and anagosic interactions; stacking, anion- / cation-π interactions; metallophilic interactions and others) in various inorganic, organic, organometallic and coordination compounds and their supramolecular associates, to identify the main factors and general patterns responsible for their appearance; (2) to understand the nature of these intermolecular and intramolecular contacts, quantify their energy, find correlations between theoretically calculated parameters of non-covalent interactions and actually experimentally observed properties of the chemical systems under study; (3) to use the knowledge gained to search for new original paths of the directional supramolecular design - the creation of clusters, chains, networks and frame structures in the liquid and solid phases.

Expected results
This project involves conducting a comprehensive and systematic theoretical study of the nature and energy characteristics of non-covalent interactions (for example, hydrogen, halogen, chalcogen, pnictogen, tetrel and semi-coordination bonds; agosic and anagosic interactions; stacking, anion- / cation-π interactions; metallophilic interactions and others) in model systems built on the basis of experimental data by means of modern high-level quantum chemical calculations (ab initio and/or density functional theory) and application of some special techniques: topological analysis of the electron density distribution within the formalism of Bader's theory (QTAIM); investigation of the effects of crystal packing on the structure of isolated molecular clusters stabilized by weak interactions using the Hirshfeld surface analysis; analysis of natural bond orbitals and charges within the framework of the Weinhold theory (NBO); analysis of charge and energy decomposition in the framework of the formalisms of Frenking and Morokuma theories (CDA and EDA, respectively), if necessary, it is possible to quantify the relative contributions of sigma-donation from ligand to metal and reverse pi-donation from metal to ligand; calculations of molecular electrostatic potentials and identification of areas most susceptible to nucleophilic / electrophilic / radical attacks; calculation of Fukui functions; calculation of the adiabatic and vertical dissociation energies of supramolecular ensembles and the subsequent correction of these energies taking into account the basis set superposition error according to the Boys-Bernardi technique (BSSE correction); calculation of thermochemical parameters, in particular, the enthalpy of formation, using the method of isodesmic reactions; application of theoretical model of the principle of hard and soft acids and bases (HSAB principle theoretical model) to search of various correlations between theoretically calculated (chemical potential; hardness and softness; global indices of electrophilicity and nucleophilicity; the maximum amount of electron charge that an electrophilic system can accept; static charge transfer "nucleophile → electrophile") and experimentally observed (contact lengths; spectral characteristics; conductivity; magnetic and photo-physical properties) parameters. In addition, it is planned to study theoretically the relative stability of various inorganic, organic, organometallic and coordination compounds, which can act as building blocks for creation of supramolecular systems; their structural features; vibrational frequencies; conformational transitions and rotation barriers of functional groups; orbital and charge factors. In the case of studying model systems with an open electron shell, the degree of purity of the spin state can be checked and a quantitative determination of the spin impurity fraction can be carried out. If it is necessary to take into account the effects of the solvent on the geometric features of supramolecular associates, it is proposed to use modern solvation models (for example, PCM, CPCM, IPCM, SMD) and / or explicit consideration of solvent molecules in the system being modeled. Within the framework of this project, it is also possible to study the mechanisms of various chemical reactions and their driving forces, kinetic and thermodynamic factors. It is planned to carry out a full geometry optimization of the structures of the starting compounds, intermediates and reaction products, as well as transition states, in order to study the energy and activation barriers of the corresponding transformations. The proofs of the localization of the correct minimum or saddle point on the potential energy surface will be performed by analyzing the Hessian matrix. The study of the nature of the transition states will be performed by analyzing the vectors conjugated with the imaginary frequency in the calculated vibrational spectrum, and / or by calculating the internal reaction coordinate according to the González-Schlegel method. If necessary, the synchronicity of reactions will be also studied. The results obtained during the realization of this project will contribute to understanding the nature of compounds with a wide range of applications in biology and medicine (for example, in neutron-capture therapy of oncological diseases; in the creation of drugs with antibacterial, antiviral, anti-inflammatory and antiallergic activity), in catalysis of important technological processes (for example, Suzuki, Heck and Sonogashira cross-coupling reactions; various hydrocarbons oxidation processes and their conversion to alcohols, epoxides, ethers, aldehydes, ketones and carboxylic acids - this topic is highly relevant for the oil and gas industry), as well as in creation of functional materials with valuable properties (for example, mechanical, redox, magnetic and optical), what makes them promising for the manufacture of high-tech battery and fuel cells, LEDs and photovoltaic solar power plants. The planned studies are interdisciplinary in nature and lie at the junction of computer modeling with such natural science disciplines as chemistry, physics, crystallography, biology and medicine, and also have a direct bearing on the materials science and nanotechnology. The proposed methods and approaches for theoretical studies are fully consistent with the top-level world standarts, which is indirectly confirmed by the fact that the applicant's previous works were consistently published in reputable international scientific journals with high impact factors (for example, J. Am. Chem. Soc., Angew. Chem. Int. Ed., Chem. Commun., Chem. Eur. J., ACS Catal., RSC Catal. Sci. Tech., Inorg. Chem., J. Org. Chem., Organometallics, Phys. Chem. Chem. Phys., Dalton Trans., Cryst. Growth Des., CrystEngComm and others).

Annotation of the results obtained in 2020
During the second year of the implementation of the RSF project No. 19-73-00001 "Theoretical studies of non-covalent interactions in chemical systems promising for catalysis, materials science, and medicine", the largest amount of work was focused on the main goal of the project - theoretical studies of non-covalent interactions (studying their nature and energies, qualitative and quantitative description of this phenomenon) in chemical systems that are promising for the needs of catalysis, materials science and medicine (in various inorganic, organic, organometallic and coordination compounds and their supramolecular associates). The main scientific results obtained: 1) The theoretical study of the nature of [(2-MeO-5-BrPh)3SbI]+ cation as a promising building block for supramolecular design of materials based on the halogen bonds as well as a potential organic catalyst operating through non-covalent interactions. 2) The phenomenon of halogen bonds with the participation of halogenated benzenes and the lone electron pair of the carbon atom in the isocyanide molecule was theoretically studied. These non-covalent interactions significantly reduce the unpleasant odor of isocyanides, which can potentially facilitate handling of these reagents in the laboratory. 3) Various non-covalent interactions halogen...halogen in crystals of a series of halogenated aromatic dichlorodiazadienes (a fairly rare class of azo-dyes) were theoretically studied. It was shown that due to such non-covalent interactions it is possible to control the peculiarities of crystal packing and supramolecular organization in the solid phase. 4) The stabilization of the {Br10}2− decabromide anion in the structure of the bromide complex Sb(V) (4-MePyC3)2{[SbBr6]2{Br10}} (4-MePyC3 = 1,10 (propane-1,3-diyl)- bis(4-methylpyridin)-1-ium dication) (a potentially promising compound for creating innovative functional materials for the needs of electronics and photovoltaics)was theoretically studied. The nature and energy characteristics of non-covalent interactions Br...Br in this compound, which are responsible for the supramolecular organization, were studied theoretically using high-level quantum-chemical calculations within the framework of the density functional theory. 5) A fundamental theoretical study was carried out for idealized simplest model systems capable of participating in the formation of halogen bonds. It was shown that in many cases the general electrostatic interaction between interacting particles can be destabilizing, and the delocalization of the electron density and the effects of charge transfer can be very significant for the stabilization of such supramolecular systems. 6) A study of supramolecular dimers in the crystal structure of (Z)-1-(((4-fluoropyridine-2yl)amino)methylene)naphthalen-2(1H)-one (a substance with potentially valuable photochromic / thermochromic, antibacterial and antitumor properties) connected due to C(sp2)—H...F hydrogen bonds was carried out. The nature of these non-covalent interactions was studied theoretically using high-level quantum-chemical calculations in the framework of the density functional theory, as well as the analysis of Hirschfeld surfaces based on the results of X-ray structural studies. 7) A study of supramolecular 1D polymers based on gold(III) coordination compounds (trans-dibromogold(III)t-Bu-Xantphos complex) was carried out. The nature and energetics of noncovalent interactions Au–Br...Br–Au, due to which 1D chains are formed in the crystalline phase, were studied theoretically using high-level quantum-chemical calculations within the framework of the density functional theory. The achieved scientific results were presented at the following international scientific events: 1) December 10–11, 2020 - First Russian-German Virtual Conference on Interdisciplinary Natural Sciences: An Interactive Online G-RISC Event (oral presentation: "Computer modeling of non-covalent interactions in chemical systems promising for materials science, catalysis and medicine") [https://www.g-risc.org/conferences_workshops/Digital-and-Online-Events/Virtual-Conference-2020.html] 2) April 26–27, 2021 - Online Symposium on Computational Chemistry in Memory of A.A. Granovsky (oral presentation: "Computer modeling in organometallic and coordination chemistry: reactivity and non-covalent interactions") [https://chemport.ru/webconference2021/] Thus, the planned work on the reporting period within the RSF project No. 19-73-00001 "Theoretical studies of non-covalent interactions in chemical systems promising for catalysis, materials science, and medicine" has been successfully done, and there is a significant over fulfillment of the plan. All project tasks on the reporting period have been successfully solved. As a result of the project implementation within the reporting period, 7 articles were published in leading specialized international scientific journals (Nat. Commun., J. Comput. Chem., Molecules, New J. Chem., J. Coord. Chem., Z. Kristallogr. Cryst. Mater., J. Struct. Chem.). The results of the research were reported and discussed at various international scientific events as oral presentations.

Publications

1. Bondarenko M.A., Novikov A.S., Fedin V.P., Sokolov M.N., Adonin S.A. The stabilization of decabromide {Br10}2− anion in the structure of Sb(V) bromide complex JOURNAL OF COORDINATION CHEMISTRY, J. Coord. Chem. 2020, V. 73. P. 3038. (year - 2020) https://doi.org/10.1080/00958972.2020.1837785

2. Jiménez-Grávalos F., Gallegos M., Pendás Á.M., Novikov A.S. Challenging the electrostatic σ‐hole picture of halogen bonding using minimal models and the interacting quantum atoms approach Journal of Computational Chemistry, J. Comput. Chem. 2021, V. 42. P. 676. (year - 2021) https://doi.org/10.1002/jcc.26488

3. Mikherdov A.S., Novikov A.S., Boyarskiy V.P., Kukushkin V.Yu. The halogen bond with isocyano carbon reduces isocyanide odor Nature Communications, Nat. Commun. 2020, V. 11. P. 2921. (year - 2020) https://doi.org/10.1038/s41467-020-16748-x

4. Nenajdenko V.G., Shikhaliyev N.G., Maharramov A.M., Bagirova K.N., Suleymanova G.T., Novikov A.S., Khrustalev V.N., Tskhovrebov A.G. Halogenated diazabutadiene dyes: synthesis, structures, supramolecular features, and theoretical studies Molecules, Molecules 2020, V. 25. P. 5013. (year - 2020) https://doi.org/10.3390/molecules25215013

5. Sharutin V.V., Sharutina O.K., Novikov A.S., Adonin S.A. Substituent-dependent reactivity of triarylantimony(III) toward I2: isolation of [Ar3SbI]+ salt New Journal of Chemistry, New J. Chem. 2020, V. 44. P. 14339. (year - 2020) https://doi.org/10.1039/D0NJ02774J

6. Tskhovrebov A.G., Novikov A.S., Khrustalev V.N. Identification of supramolecular dimers in the crystal structure of (Z)-1-(((5-fluoropyridin-2-yl)amino)methylene)naphthalen-2(1H)-one via C(sp2)—H⋯F hydrogen bonding: A combined experimental and theoretical study Журнал структурной химии, ЖСХ, 2021, Т. 62. С. 490. (year - 2021) https://doi.org/10.26902/JSC_id69922

7. Tskhovrebov A.G., Novikov A.S., Kritchenkov A.S., Khrustalev V.N., Haukka M. Attractive halogen···halogen interactions in crystal structure of trans-dibromogold(III) complex Zeitschrift für Kristallographie – Crystalline Materials, Z. Kristallogr. Cryst. Mater. 2020, V. 235. P. 477. (year - 2020) https://doi.org/10.1515/zkri-2020-0045

8. - Новый тип связи с атомом углерода смог устранить отвратительный запах изоцианидов Интернет-портал Indicator.ru, - (year - )

9. - Открытый химиками СПбГУ новый тип связи с атомом углерода смог устранить отвратительный запах изоцианидов Сайт Института химии СПбГУ, - (year - )

Annotation of the results obtained in 2019
During the first year of the implementation of the RSF project No. 19-73-00001 "Theoretical studies of non-covalent interactions in chemical systems promising for catalysis, materials science, and medicine", the largest amount of work was focused on the main goal of the project - theoretical studies of non-covalent interactions (studying their nature and energies, qualitative and quantitative description of this phenomenon) in chemical systems that are promising for the needs of catalysis, materials science and medicine (in various inorganic, organic, organometallic and coordination compounds and their supramolecular associates). The main scientific results obtained: 1) The nature and energy characteristics of non-covalent interactions Br•••Br responsible for the supramolecular organization of new coordination compounds of Sb(V): Cat[SbBr6] (Cat = 1,3,4-MePy+, 1,4-MePy+) and Cat2{[SbBr6](Br3)} (Cat = 1,2-MePy+, 1-Et-2-MePy+, 1-Et-4-MePy+) were theoretically studied. These compounds are potentially promising for the creation of innovative functional materials for the needs of electronics and photovoltaics. 2) The phenomenon of the presence of halogen bonds X•••O (X = Cl, Br, I) (the nature and energy characteristics of these non-covalent interactions) responsible for the supramolecular organization of isostructural coordination compounds [(Bu4N)2[{Ag(L)(DMF)}2Mo8O26] (L = 3-chloro-, 3-bromo-, 3-iodopyridine) in the solid phase was theoretically studied. These compounds are promising for the needs of materials science. 3) A theoretical study of the nature and energy characteristics of the rare type of intermolecular hydrogen bonds C(sp2)–H•••Hal and weak intermolecular non-covalent interactions N–H•••Ph responsible for the formation of 1D supramolecular polymer chains in crystals of dichloroosazone complexes of palladium(II) was carried out. 4) The nature and energy of coordination and semicoordination bonds and stacking interactions in crystal of silver(I) coordination compound with 8-phenylquinoline ligand were studied by using high level quantum chemical calculations. Such coordination compounds are promising as catalysts for different processes of Csp3–H functionalization and various chemical reactions involving substrates with C=С and С≡С bonds. Intermolecular interactions in the solid phase were also additionally investigated by Hirschfeld surface analysis for the asymmetric unit in the crystal. 5) The nature and energy of coordination and semicoordination bonds Ni•••I, halogen bonds and lp•••π interactions in the adducts of square-planar nickel(II) dioximate complexes [Ni(bqoxH)2] (bqoxH2 = o-benzoquinonedioxime) with iodine and polyiodide anions (redox active systems, promising for creating innovative materials with conductive or semiconductor properties) were studied theoretically using high level quantum chemical calculations and specialized CrystalExplorer software package based on the result in X-ray diffraction studies. 6) The nature and energy of non-covalent interactions I•••I in crystals of salts of pyridine derivatives with triiodide anions CatI3 (Сat =1,2-MePy and 1,2,6-MePy) were theoretically studied, which gives an understanding of the driving forces of supramolecular organization of these systems and opens up opportunities for crystal engineering design based on these building blocks. 7) It was theoretically proved that the intramolecular hydrogen bonds N–H•••Cl stabilize the trans-configuration of the palladium(II) carbene complex, which can be a catalyst for the most important organic cross-coupling reactions — the Suzuki, Heck, Sonogashira, and others. Various intermolecular non-covalent interactions in the solid phase were also additionally investigated by Hirschfeld surface analysis for the obtained crystal structure of this palladium(II) carbene complex. 8) It was theoretically proved that the quasi-cyclic conformation of N-acylureas (organic compounds that are widely used in materials science [gels, nanotubes, nanosheets, polymers with nonlinear optical properties], catalysis of nucleophilic ring opening reactions in epoxides and the pharmacological industry [precursors for antidiabetic, antitumor and anti-inflammatory drugs]) is determined by intramolecular hydrogen bonds stabilized by electronic delocalization (resonance-assisted hydrogen bonding), while their dimerization in solid phase occurs due to the formation of intermolecular hydrogen bonds N–H•••O and C–H•••O. The nature and energy characteristics of these non-covalent interactions were studied using high level quantum chemical calculations. Various intermolecular non-covalent interactions in the solid phase were also additionally investigated by Hirschfeld surface analysis for the obtained crystal structures of N-acylureas. 9) The specific non-covalent interactions I•••I and Br•••I were found in the crystal structure of heteroleptic binuclear iodoacetate complexes of copper(II) with 3-bromopyridine [Cu2(IOAc)4(3-BrPy)2]. These non-covalent interactions lead to the formation of supramolecular polymers. The nature and energy characteristics of these non-covalent interactions were studied theoretically using high level quantum chemical calculations. 10) The nature and energy of non-covalent interactions Br•••Br in the supramolecular structure of polybromide-bromoantimonate (2,6-BrPy)3[SbBr6]{(Br2)Br}•2H2O were studied theoretically using high level quantum chemical calculations. A growing interest in such halide complexes of p-elements in significant degrees associated with the possibility of their usage as components of solar cells of the so-called perovskite type. 11) The mechanism and driving forces, kinetic and thermodynamic factors of the regio- and stereoselective cycloaddition reactions of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones were studied. The reactivity of these compounds was analyzed using the frontier molecular orbitals theory, global electrophilicity and nucleophilicity indices, and Fukui functions. These reactions lead to the formation of isoxazolidine heterocycles promising for creation of pharmaceuticals having inhibitory activity against the H1N1 influenza virus. The achieved scientific results were presented at the following international scientific events: 1) September 2-6, 2019 (Lisbon, Portugal) - 1st International Conference on Noncovalent Interactions (ICNI 2019) (poster presentation: "Theoretical studies of noncovalent interactions in chemical systems promising for catalysis, materials science, and medicine") [https://icni2019.eventos.chemistry.pt/] 2) September 9–13, 2019 (St. Petersburg, Russia) - Mendeleev 2019, the XI International Conference on Chemistry for Young Scientists (plenary lecture: "Theoretical studies in organometallic and coordination chemistry: reactivity, catalysis, and non-covalent interactions") [http://mendeleev.spbu.ru/] 3) October 20-23, 2019 (Liverpool, Great Britain) - Workshop "Dynamic self-assembly and quorum effects in chemistry and biology predicted by non-linear modelling algorithms" (oral presentation: "Computer modeling in organometallic chemistry: reactivity, catalysis, and noncovalent interactions") [http://dysa.itmo.ru/] Thus, the planned work on the reporting period within the RSF project No. 19-73-00001 "Theoretical studies of non-covalent interactions in chemical systems promising for catalysis, materials science, and medicine" has been successfully done, and there is a significant over fulfillment of the plan. All project tasks on the reporting period have been successfully solved. As a result of the project implementation within the reporting period, 11 articles were published in leading specialized international scientific journals (Inorg. Chem.; Dalton Trans.; New J. Chem.; Tetrahedron; Inorg. Chim. Acta; J. Organomet. Chem.; J. Mol. Struct.; Russ. J. Coord. Chem.). The results of the research were reported and discussed at various international scientific events as plenary, oral and poster presentations.

Publications

1. Adonin S.A., Bondarenko M.A., Novikov A.S., Plyusnin P.E., Korolkov I.V., Sokolov M.N., Fedin V.P. Five new Sb(V) bromide complexes and their polybromide derivatives with pyridinium-type cations: Structures, thermal stability and features of halogen⋯halogen contacts in solid state Inorganica Chimica Acta, Inorganica Chimica Acta 502 (2020) 119278 (year - 2020) https://doi.org/10.1016/j.ica.2019.119278

2. Adonin S.A., Novikov A.S., Fedin V.P. Гетеролептические биядерные иодоацетатные комплексы меди(II) с 3-бромпиридином и 4-этилпиридином: кристаллические структуры и особенности контактов галоген•••галоген Координационная химия, Координационная химия, 2020, том 46, № 2, с. 112–116 (year - 2020) https://doi.org/10.31857/S0132344X20020012

3. Anastasia V. Chupina, Vladimir Shayapov, Alexander S. Novikov, Victoria V. Volchek, Enrico Benassi, Pavel A. Abramov, Maxim N. Sokolov [{AgL}2Mo8O26]n– complexes: a combined experimental and theoretical study Dalton Transactions, Dalton Trans.,2020, 49,1522–1530 (year - 2020) https://doi.org/10.1039/C9DT04043A

4. Andrey N. Usoltsev, Alexander S. Novikov, Boris A. Kolesov, Katerina V. Chernova, Pavel E. Plyusnin, Vladimir P. Fedin, Maxim N. Sokolov, Sergey A. Adonin Halogen•••halogen contacts in triiodide salts of pyridinium-derived cations: Theoretical and spectroscopic studies Journal of Molecular Structure, Journal of Molecular Structure 1209 (2020) 127949 (year - 2020) https://doi.org/10.1016/j.molstruc.2020.127949

5. Bondarenko M.A., Adonin S.A., Novikov A.S., Sokolov M.N., Fedin V.P. Супрамолекулярный полибромид-бромоанимонат(V) (2,6-BrPyH)3[SbBr6]{(Br2)Br}•2H2O: особенности контактов галоген•••галоген в кристаллической структуре Координационная химия, Координационная химия, 2020, том 46, № 5, с. 264–269 (year - 2020) https://doi.org/10.31857/S0132344X20040015

6. Dmitrii S. Bolotin, Natalia S. Soldatova, Marina Ya. Demakova, Alexander S. Novikov, Daniil M. Ivanov, Irina S. Aliyarova, Alexander Sapegin, Mikhail Krasavin Pentacoordinated silver(I) complex featuring 8-phenylquinoline ligands: Interplay of coordination bonds, semicoordination, and stacking interactions Inorganica Chimica Acta, Inorganica Chimica Acta 504 (2020) 119453 (year - 2020) https://doi.org/10.1016/j.ica.2020.119453

7. Mariia M. Efremova, Alexander P. Molchanov, Alexander S. Novikov, Galina L. Starova, Anna A. Muryleva, Alexander V. Slita, Vladimir V. Zarubaev 1,3-Dipolar cycloaddition of N-allyl substituted polycyclic derivatives of isoindole-1,3-dione with nitrones and nitrile oxides: An experimental and theoretical investigation Tetrahedron, Tetrahedron 76 (2020) 131104 (year - 2020) https://doi.org/10.1016/j.tet.2020.131104

8. Mikhail V. Il’in, Liana A. Lesnikova, Dmitrii S. Bolotin, Alexander S. Novikov, Vitalii V. Suslonov, Vadim Yu. Kukushkin A one-pot route to N-acyl ureas: a formal four-component hydrolytic reaction involving aminonitrones and isocyanide dibromides New Journal of Chemistry, New J. Chem., 2020, 44, 1253 (year - 2020) https://doi.org/10.1039/c9nj05445f

9. Olga V. Repina, Alexander S. Novikov, Olesya V. Khoroshilova, Andreii S. Kritchenkov, Alexander A. Vasin, Alexander G. Tskhovrebov Lasagna-like supramolecular polymers derived from the PdII osazone complexes via C(sp2)–H⋯Hal hydrogen bonding Inorganica Chimica Acta, Inorganica Chimica Acta 502 (2020) 119378 (year - 2020) https://doi.org/10.1016/j.ica.2019.119378

10. Vladimir N. Mikhaylov, Viktor N. Sorokoumov, Alexander S. Novikov, Maria V. Melnik, Alexander G. Tskhovrebov, Irina A. Balova Intramolecular hydrogen bonding stabilizes trans-configuration in a mixed carbene/isocyanide PdII complexes Journal of Organometallic Chemistry, Journal of Organometallic Chemistry 912 (2020) 121174 (year - 2020) https://doi.org/10.1016/j.jorganchem.2020.121174

11. Zarina M. Efimenko, Alexander S. Novikov, Daniil M. Ivanov, Alexandr V. Piskunov, Anatoly A. Vereshchagin, Oleg V. Levin, Nadezhda A. Bokach, Vadim Yu. Kukushkin The (Dioximate)NiII/I2 System: Ligand Oxidation and Binding Modes of Triiodide Species Inorganic Chemistry, Inorg. Chem. 2020, 59, 2316−2327 (year - 2020) https://doi.org/10.1021/acs.inorgchem.9b03132