Публикации

Cyclic dipeptide peroxosolvates: first direct evidence for hydrogen bonding between hydrogen peroxide and a peptide backbone / A. V. Churakov, D. A. Grishanov, A. G. Medvedev et al. // CrystEngComm. — 2019. — Vol. 21, no. 33. — P. 4961–4968. Herein, peroxosolvates of the cyclic dipeptides disarcosine (C6H10N2O2·H2O2), dialanine (C6H10N2O2·2(H2O2)), diglycine (C4H6N2O2·2(H2O2) and C4H6N2O2·1.786(H2O2)·0.214(H2O)) were synthesized and studied by single crystal X-ray analysis and periodic DFT calculations. The hydrogen bonding networks of cyclic diglycine peroxosolvate and isomorphous hydrate were characterized using Bader analysis of periodic electron density and empirical correlations between enthalpy and metric and spectroscopic parameters of the H-bond. The obtained data for the peroxosolvate of cyclic dipeptides provided a molecular-level insight into the non-redox interaction of hydrogen peroxide with the peptide backbone in aqueous systems. In all structures, H2O2 acts as a proton donor in two hydrogen bonds. The carbonyl oxygen atom of the peptide (-CO-NH-) forms a relatively stronger hydrogen bond with the hydrogen peroxide molecule (32-34 kJ mol-1) as compared to that with water in the isomorphous hydrate of cyclic diglycine (26-28 kJ mol-1). The hydrogen atom of the peptide group (-CO-NH-) can form a moderate H-bond with hydrogen peroxide (25 kJ mol-1). The total hydrogen bonding energy of the peroxosolvate is higher than that of the corresponding hydrate (91 vs. 82 kJ mol-1). The stronger hydrogen bonding in peroxosolvates as compared to that in the hydrate and the fact that the intermolecular H-bonds C(O)NH⋯OCNH between cyclic dipeptides are not found in peroxosolvates, despite being prevalent in the structure of nonsolvated dipeptides, imply that hydrogen peroxide can interfere with the secondary structure of proteins via a mechanism that can lead to reversible inhibition or signaling in living systems. [ DOI ]

Effect of aluminum vacancies on the h 2 o 2 or h 2 o interaction with a gamma-alooh surface. a solid-state dft study / A. G. Medvedev, A. A. Mikhaylov, I. Y. Chernyshov et al. // International Journal of Quantum Chemistry. — 2019. — Vol. 119, no. 13. — P. e25920. The adsorption of a single H 2 O 2 or H 2 O molecule on a family of periodic slab models of γ-AlOOH is studied by solid-state DFT. The single H 2 O 2 or Н 2 О molecule interacts with the perfect (010) slab by intermolecular hydrogen bonds (H-bonds). In the models of γ-AlOOH with oxygen and aluminum vacancies, H 2 O 2 or Н 2 О also forms covalent O∙∙∙Al bonds. The energies of covalent O∙∙∙Al and H-bonds are estimated by a combined approach based on simultaneous consideration of the total binding energies with BSSE correction and empirical schemes of the Н-bond energy evaluation. The O∙∙∙Al bond energy ranges from ∼75 to ∼156 kJ mol −1 . The total energy of H-bond interactions in the case of H 2 O 2 exceeds that of Н 2 О by ∼30 kJ mol −1 for all considered slab models. In contrast to Н 2 О, a H 2 O 2 molecule always forms two H-bonds as the proton donor. The energy of these bonds noticeably increase on defect γ-AlOOH surfaces in comparison with the perfect slab due to formation of short (strong) H-bonds by adsorbed H 2 O 2 . [ DOI ]

Solving the enigma of weak fluorine contacts in the solid state: a periodic dft study of fluorinated organic crystals / E. O. Levina, I. Y. Chernyshov, A. P. Voronin et al. // RSC advances. — 2019. — Vol. 9, no. 22. — P. 12520–12537. The nature and strength of weak interactions with organic fluorine in the solid state are revealed by periodic density functional theory (periodic DFT) calculations coupled with experimental data on the structure and sublimation thermodynamics of crystalline organofluorine compounds. To minimize other intermolecular interactions, several sets of crystals of perfluorinated and partially fluorinated organic molecules are considered. This allows us to establish the theoretical levels providing an adequate description of the metric and electron-density parameters of the C–F⋯F–C interactions and the sublimation enthalpy of crystalline perfluorinated compounds. A detailed comparison of the C–F⋯F–C and C–H⋯F–C interactions is performed using the relaxed molecular geometry in the studied crystals. The change in the crystalline packing of aromatic compounds during their partial fluorination points to the structure-directing role of C–H⋯F–C interactions due to the dominant electrostatic contribution to these contacts. C–H⋯F–C and C–H⋯O interactions are found to be identical in nature and comparable in energy. The factors that determine the contribution of these interactions to the crystal packing are revealed. The reliability of the results is confirmed by considering the superposition of the electrostatic potential and electron density gradient fields in the area of the investigated intermolecular interactions. [ DOI ]

Azasydnone – novel "green" building block for designing high energetic compounds / I. L. Dalinger, O. V. Serushkina, N. V. Muravyev et al. // Journal of Materials Chemistry A. — 2018. — Vol. 6. — P. 18669–18676. [ DOI ]

Hydration of the carboxylate group in anti-inflammatory drugs: Atr-ir and computational studies of aqueous solution of sodium diclofenac / E. O. Levina, N. V. Penkov, N. N. Rodionova et al. // ACS Omega. — 2018. — Vol. 3, no. 1. — P. 302–313. Diclofenac (active ingredient of Voltaren) has a significant, multifaceted role in medicine, pharmacy, and biochemistry. Its physical properties and impact on biomolecular structures still attract essential scientific interest. However, its interaction with water has not been described yet at the molecular level. In the present study, we shed light on the interaction between the steric hindrance (the intramolecular N-H center dot center dot center dot O bond, etc.) carboxylate group (-CO2-) with water. Aqueous solution of sodium declofenac is investigated using attenuated total reflection-infrared (ATR-IR) and computational approaches, i.e., classical molecular dynamics (MD) simulations and density functional theory (DFT). Our coupled classical MD simulations, DFT calculations, and ATR-IR spectroscopy results indicated that the -CO2- group of the diclofenac anion undergoes strong specific interactions with the water molecules. The combined experimental and theoretical techniques provide significant insights into the spectroscopic manifestation of these interactions and the structure of the hydration shell of the -CO2- group. Moreover, the developed methodology for the theoretical analysis of the ATR-IR spectrum could serve as a template for the future IR/Raman studies of the strong interaction between the steric hindrance -CO2- group of bioactive molecules with the water molecules in dilute aqueous solutions. [ DOI ]

Hypercoordinated oligosilanes based on aminotrisphenols / M. M. Aghazadeh, K. V. Zaitsev, M. V. Vener et al. // ACS Omega. — 2018. — Vol. 3, no. 8. — P. 10317–10330. The hypercoordinated silicon chlorides ClSi[(o-OC6H4)3N] (3) and ClSi[(OC6H2Me2CH2)3N] (5) were used for the synthesis of catenated derivatives (Me3Si)3SiSi[(o-OC6H4)3N] (9), (Me3Si)3SiSiMe2SiMe2Si(SiMe3)2Si[(o-OC6H4)3N] (11), and (Me3Si)3SiSi[(OC6H2Me2CH2)3N] (13) in reactions with (Me3Si)3SiK·THF (7) or (Me3Si)3SiK·[18-crown-6] (8). It was found that the nature of the (Me3Si)3SiK solvate determines the product of interaction, resulting in the formation of (Me3Si)3Si(CH2)4OSi[(OC6H2Me2CH2)3N] (12) or 13. Compounds obtained were characterized using multinuclear NMR and UV-vis spectroscopy and mass spectrometry. The molecular structures of 3, 9, and 11-13 were investigated by single-crystal X-ray analysis, featuring hypercoordinated Si atoms in a trigonal-bipyramidal coordination environment with O atoms in the equatorial plane. The structure of the side product [N(CH2C6H2Me2O)3Si]2O (6) was also studied, indicating highly tetrahedrally distorted trigonal-bipyramidal environment at the Si atoms, which was confirmed by crystal density functional theory calculations indicating the very weak Si ← N interaction. The Si···N interatomic distances span a broad range (2.23-2.78 Å). The dependence of structural and NMR parameters for hypercoordinated catenated compounds from the type of the ligand was established. [ DOI ]

Relationship between electron-phonon interaction and low-frequency raman anisotropy in high-mobility organic semiconductors / Y. S. Andrey, M. Dmitry, I. Y. Chernyshov et al. // Physical Chemistry Chemical Physics. — 2018. Недавние теоретические исследования показывают, что перенос заряда в органических полупроводниках ограничен низкочастотными колебаниями вследствие сильного нелокального электрон-фононного взаимодействия. В настоящей работе мы исследовали два высокоэффективных органических полупроводника с аналогичными молекулярными структурами, но значительно отличающейся кристаллической упаковкой, TCNQ и F2-TCNQ, и выявили связь между экспериментальными низкочастотными спектрами комбинационного рассеяния и рассчитанными вкладами различных колебательных мод в электрон-фононное взаимодействие. Мы предполагаем, что комбинация комбинационной спектроскопии с квантово-химическими расчётами является мощным инструментом для изучения электрон-фононного взаимодействия и целенаправленного поиска органических полупроводников с высокой подвижностью зарядов. [ DOI ]

Structural and spectroscopic features of proton hydrates in the crystalline state. solid-state dft study on hcl and triflic acid hydrates / M. V. Vener, I. Y. Chernyshov, A. A. Rykounov, A. Filarowski // Molecular Physics. — 2018. — Vol. 116, no. 2. — P. 251–262. Crystalline HCl and CF3SO3H hydrates serve as excellent model systems for protonated water and perfluorosulphonic acidmembranes, respectively. They contain characteristic H3O+, H5О2+, H7О3+ and H3O+(H2O)3 (the Eigen cation) structures. The properties of these cations in the crystalline hydrates of strong monobasic acids are studied by solid-state density function theory (DFT). Simultaneous consideration of the HCl and CF3SO3H hydrates reveals the impact of the size of a counter ion and the crystalline environment on the structure and infrared active bands of the simplest proton hydrates. The H7O3+ structure is very sensitive to the size of the counter ion and symmetry of the local environment. This makes it virtually impossible to identify the specific features of H7O3+ in molecular crystals.The H3O+ ion can be treated as the Eigen-like cation in the crystalline state. Structural, infrared and electron-density features of H5О2+ and the Eigen cation are virtually insensitive to the size of the counter ion and the symmetry of the local crystalline environment. These cations can be considered as the simplest stable proton hydrates in the condensed phase. Finally, the influence of the Grimme correction on the structure and harmonic frequencies of the molecular crystals with short (strong) intermolecular O–H···O bonds is discussed. [ DOI ]

Inhibiting low-frequency vibrations explains exceptionally high electron mobility in 2,5-difluoro-7,7,8,8-tetracyanoquinodimethane (f2-tcnq) single crystals / I. Y. Chernyshov, M. V. Vener, E. V. Feldman et al. // Journal of Physical Chemistry Letters. — 2017. — Vol. 8, no. 13. — P. 2875–2880. [ DOI ]

Peroxosolvates: formation criteria, h2o2 hydrogen bonding, and isomorphism with the corresponding hydrates / I. Y. Chernyshov, M. V. Vener, P. V. Prikhodchenko et al. // Crystal Growth and Design. — 2017. — Vol. 1, no. 17. — P. 214–220.

The role of london dispersion interactions in strong and moderate intermolecular hydrogen bonds / S. A. Katsyuba, M. V. Vener, E. E. Zvereva, J. G. Brandenburg // Chemical Physics Letters. — 2017. — Vol. 672. — P. 124–127. Two variants of density functional theory computations have been applied to characterization of hydrogen bonds of the 1-(2-hydroxylethyl)-3-methylimidazolium acetate ([C2OHmim][OAc]), i.e. with and without inclusion of dispersion interactions. A comparison of the results demonstrates that London dispersion interactions have very little impact on the energetical, geometrical, infrared spectroscopic and electron density parameters of charge-assisted intermolecular hydrogen bonds functioning both in the crystal of the [C2OHmim][OAc] and in the isolated [C2OHmim]+ [OAc]
ion pairs. [ DOI ]

Weak interactions cause packing polymorphism in pharmaceutical two-component crystals. the case study of the salicylamide cocrystal / A. O. Surov, A. N. Manin, A. P. Voronin et al. // Crystal Growth and Design. — 2017. — Vol. 17. — P. 1425–1437. Two polymorphs of the salicylamide cocrystal with oxalic acid have been obtained and described. Form I of the cocrystal was prepared by three alternative methods in various solvents, while formation of form II was achieved only by a special crystallization procedure. Single-crystal X-ray analysis has revealed that polymorphs consist of conformationally identical salicylamide and oxalic acid molecules, which are assembled into supramolecular units connected via a network of very similar hydrogen bonds. The packing arrangements of the cocrystal polymorphs, however, were found to be different, suggesting a rare example of packing polymorphism. The stability relationship between the polymorphs has been rationalized by using a number of experimental methods, including thermochemical analysis, solubility, and solution calorimetry measurements. Similarities and differences in intermolecular contacts across two polymorphs have been visualized using the Hirshfeld surface analysis. The Bader analysis of the theoretical electron density has enabled us to quantify the pattern of noncovalent interactions in the considered cocrystals. Applicability of different theoretical schemes for evaluation of the lattice energy of the two-component organic crystals has been discussed. [ DOI ]

Voronin A. P., Perlovich G. L., Vener M. V. Effects of the crystal structure and thermodynamic stability on solubility of bioactive compounds: Dft study of isoniazid cocrystals // Computational & theoretical chemistry. — 2016. — Vol. 1092. — P. 1–11. Intrinsic solubility of the isoniazid-carboxylic acid cocrystals is explored using thermodynamic cycle of transferring from crystal to gas and then to solution. The enthalpy/Gibbs free energy of phase transitions is computed by solid-state DFT (crystal) and DFT methods with/without accounting for polar solvent (aqueous solution/gas). The dissolution process of the isoniazid-dicarboxylic acid 2:1 cocrystals is foundto be enthalpy-determined. The linear correlation between the theoretical sublimation enthalpies andexperimental Gibbs energy of solution is established. According to it, the increase of stability causes the decrease of the considered cocrystals solubility. We conclude that a soluble and relatively stable cocrystal of isoniazid should be characterized by the sublimation enthalpy varying from 185 to 200 kJ
mol-1. Bader analysis of theoretical periodic electron density enables us to quantify the noncovalent interactions and clarify their role in formation of the isoniazid cocrystals. The sublimation enthalpy of the cocrystals is defined by the structure of the coformer molecule. Its value is less 150 kJ
mol-1 in the case of aromatic acids and larger than 180 kJ
mol1 for the aliphatic dicarboxylic acids. The sublimation enthalpy increases with the increase of the dicarboxylic acid hydrocarbon chain. [ DOI ]

Peroxosolvates: Formation criteria, h2o2 hydrogen bonding, and isomorphism with the corresponding hydrates / I. Y. Chernyshov, M. V. Vener, P. V. Prikhodchenko et al. // Crystal Growth and Design. — 2016. — Vol. 17, no. 1. — P. 214–220. [ DOI ]

Spectral features of guanidinium-carboxylate salt bridges. the combined atr-ir and theoretical studies of aqueous solution of guanidinium acetate / E. O. Levina, B. V. Lokshin, B. D. Mai, M. V. Vener // Chemical Physics Letters. — 2016. — Vol. 659. — P. 117–120. The spectrum of guanidinium acetate in aqueous solution has been recorded by attenuated total reflectance infrared spectroscopy (ATR-IR). Assignments of the bands have been done using the polarizable continuum model (PCM). Three IR intensive bands at 1670, 1550, and 1410 cm-1 are associated with stretching and bending vibrations of the groups forming a ring of six heavy atoms of the bidentate configuration of guanidinium acetate. The relatively weak broad band near 2200 cm-1 is tentatively assigned to the stretching vibration of the N-H...O fragment of the hydrogen-bonded ion pairs. [ DOI ]

ОСОБЕННОСТИ КОНТАКТНОЙ ИОННОЙ ПАРЫ ГУАНИДИН-АЦЕТАТ В ВОДЕ. ИССЛЕДОВАНИЕ МЕТОДАМИ НПВО И ТЕОРИИ ФУНКЦИОНАЛА ПЛОТНОСТИ / М. В. Венер, В. Н. Попов, Б. З. Май, Б. В. Локшин // Вестник Воронежского государственного университета. Серия: Химия. Биология. Фармация. — 2016. — № 3. — С. 58–62.

Influence of secondary interactions on the structure, sublimation thermodynamics and solubility of salicylate:4-hydroxybenzamide cocrystals combined experimental and theoretical study / A. N. Manin, A. P. Voronin, A. V. Shishkina et al. // Journal of Physical Chemistry B. — 2015. — Vol. 119. — P. 10466–10477. Cocrystal screening of 4-hydroxybenzamide with a number of salicylates (salicylic acid, SA; 4-aminosalicylic acid, PASA; acetylsalicylic acid, ASA; and salicylsalicylic acid, SSA) was conducted to confirm the formation of two cocrystals, [SA+4-OHBZA] (1:1) and [PASA+4-OHBZA] (1:1). Their structures were determined using single-crystal X-ray diffraction, and the hydrogen-bond network topology was studied. Thermodynamic characteristics of salicylic acid cocrystal sublimation were obtained experimentally. It was proved that PASA cocrystallization with 4-OHBZA makes the drug more stable and prevents the irreversible process of decarboxylation of PASA resulting in formation of toxic 3-aminophenol. The pattern of non-covalent interactions in the cocrystals is described quantitatively using solid-state density functional theory followed by Bader analysis of the periodic electron density. It has been found that the total energy of secondary interactions between synthon atoms and the side hydroxyl group of the acid molecule in [SA+4-OHBZA] (1:1) and [PASA+4-OHBZA] (1:1) cocrystals is comparable to the energy of the primary acid−amide heterosynthon. The theoretical value of the sublimation enthalpy of [SA+4-OHBZA], 231 kJ/mol, agrees fairly well with the experimental one, 272 kJ/mol. The dissolution experiments with [SA+4-OHBZA] have proved that the relatively large cocrystal stability in relation to the stability of its components has a negative effect on the dissolution rate and equilibrium solubility. The [PASA+4-OHBZA] (1:1) cocrystal showed an enhancement of apparent solubility compared to that of the corresponding pure active pharmaceutical ingredient, while their intrinsic dissolution rates are comparable. [ DOI ]

Potassium cesium and ammonium peroxogermanates with inorganic hexanuclear peroxo bridged germanium anion isolated from aqueous solution / A. G. Medvedev, A. A. Mikhaylov, A. V. Churakov et al. // Inorganic Chemistry. — 2015. — Vol. 54. — P. 8058–8065. Potassium, cesium ammonium and potassium ammonium peroxogermanates were isolated from 3% hydrogen peroxide aqueous solutions of the corresponding hydroxogermanates and characterized by single crystal and powder X-ray diffraction studies and by Raman spectroscopy and thermal analysis. The crystal structure of all three compounds consists of cations of potassium and/or ammonium and cesium, water molecules, and centrosymmetric hexanuclear peroxogermanate anion with six μ-oxo- and six μ-peroxo groups. Peroxogermanates demonstrate relatively high thermal stability: the peroxide remains in the structure even after water release after heating to 100−120 oC. DFT calculations of the peroxogermanate anion confirm its higher thermodynamic stability compared to the hydroperoxo- and oxogermanate analogues. [ DOI ]

Quantification of conventional and non-conventional charge-assisted hydrogen bonds in the condensed and gas phases / S. A. Katsyuba, M. V. Vener, E. E. Zvereva et al. // Journal of Physical Chemistry Letters. — 2015. — Vol. 6. — P. 4431–4436. Charge-assisted hydrogen bonds (CAHBs) play critical roles in many systems from biology through to materials. In none of these areas has the role and function of CAHBs been explored satisfactorily because of the lack of data on the energy of CAHBs in the condensed phases. We have, for the first time, quantified three types of CAHBs in both the condensed and gas phases for 1-(2′-hydroxylethyl)-3-methylimidazolium acetate ([C2OHmim][OAc]). The energy of conventional OH···[OAc]− CAHBs is ∼10 kcal· mol−1, whereas nonconventional C(sp2)H···[OAc]− and C(sp3)H···[OAc]− CAHBs are weaker by ∼5−7 kcal·mol−1. In the gas phase, the strength of the nonconventional CAHBs is doubled, whereas the conventional CAHBs are strengthened by <20%. The influence of cooperativity effects on the ability of the [OAc]− anion to deprotonate the imidazolium cation is evaluated. The ability to quantify CAHBs in the condensed phase on the basis of easier accessible gas-phase estimates is highlighted. [ DOI ]

Specific features of the extra strong intermolecular hydrogen bonds in crystals: Insights from the theoretical charge density analysis / M. V. Vener, E. O. Levina, A. A. Astakhov, V. G. Tsirelson // Chemical Physics Letters. — 2015. — Vol. 638. — P. 233–236. [ DOI ]

The applicability of the dimeric heterosynthon concept to molecules with equivalent binding sites. a dft study of crystalline urea / A. G. Medvedev, A. V. Shishkina, O. Lev et al. // RSC advances. — 2015. — Vol. 5. — P. 29601–29608.

The structure and ir signatures of the arginine-glutamate salt bridge. insights from the classical md simulations / M. V. Vener, A. V. Odinokov, C. Wehmeyer, D. Sebastiani // Journal of Chemical Physics. — 2015. — Vol. 142. — P. 215106. Salt bridges and ionic interactions play an important role in protein stability, protein-protein interactions, and protein folding. Here, we provide the classical MD simulations of the structure and IR signatures of the arginine (Arg)–glutamate (Glu) salt bridge. The Arg-Glu model is based on the infinite polyalanine antiparallel two-stranded β-sheet structure. The 1 μs NPT simulations show that it preferably exists as a salt bridge (a contact ion pair). Bidentate (the end-on and side-on structures) and monodentate (the backside structure) configurations are localized [Donald et al., Proteins 79, 898–915 (2011)]. These structures are stabilized by the short +N–H· · ·O− bonds. Their relative stability depends on a force field used in the MD simulations. The side-on structure is the most stable in terms of the OPLS-AA force field. If AMBER ff99SB-ILDN is used, the backside structure is the most stable. Compared with experimental data, simulations using the OPLS all-atom (OPLS-AA) force field describe the stability of the salt bridge structures quite realistically. It decreases in the following order: side-on > end-on > backside. The most stable side-on structure lives several nanoseconds. The less stable backside structure exists a few tenth of a nanosecond. Several short-living species (solvent shared, completely separately solvated ionic groups ion pairs, etc.) are also localized. Their lifetime is a few tens of picoseconds or less. Conformational flexibility of amino acids forming the salt bridge is investigated. The spectral signature of the Arg-Glu salt bridge is the IR-intensive band around 2200 cm−1. It is caused by the asymmetric stretching vibrations of the +N–H· · ·O− fragment. Result of the present paper suggests that infrared spectroscopy in the 2000–2800 frequency region may be a rapid and quantitative method for the study of salt bridges in peptides and ionic interactions between proteins. This region is usually not considered in spectroscopic studies of peptides and proteins. [ DOI ]

Evaluation of the lattice energy of the two-component molecular crystals using solid-state density functional theory / M. V. Vener, E. O. Levina, O. A. Koloskov et al. // Crystal Growth and Design. — 2014. — Vol. 14, no. 10. — P. 4997–5003. [ DOI ]

Nitranilic acid hexahydrate, a novel benchmark system of the zundel cation in an intrinsically asymmetric environment: hydrogen bond dynamics characterised by experimental and theoretical methods / K. Molčanov, J. Stare, M. V. Vener et al. // Physical Chemistry Chemical Physics. — 2014. — Vol. 16. — P. 998–1007. Nitranilic acid (2,5-dihydroxy-3,6-dinitro-2,5-cyclohexadiene-1,4-dione) as a strong dibasic acid in acidic aqueous media creates the Zundel cation, H5O2+. The structural unit in a crystal comprises (H5O2)2+(2,5-dihydroxy-3,6-dinitro-1,4-benzoquinonate)2 dihydrate where the Zundel cation reveals no symmetry, being an ideal case for studying proton dynamics and its stability. The Zundel cation and proton transfer dynamics are studied by variable-temperature X-ray diffraction, IR and solid-state NMR spectroscopy, and various quantum chemical methods, including periodic DFT calculations, ab initio molecular dynamics simulation, and quantization of nuclear motion along three fully coupled internal coordinates. The Zundel cation features a short H-bond with the O  O distance of 2.433(2) Å with an asymmetric placement of hydrogen. The proton potential is of a single well type and, due to the non-symmetric surroundings, of asymmetric shape. The formation of the Zundel cation is facilitated by the electronegative NO2 groups. The employed spectroscopic techniques supported by calculations confirm the presence of a short H-bond with a complex proton dynamics. [ DOI ]

Salicylamide cocrystals: Screening, crystal structure, sublimation thermodynamics, dissolution and solid-state dft calculations / A. N. Manin, A. P. Voronin, N. G. Manin et al. // Journal of Physical Chemistry B. — 2014. — Vol. 118. — P. 6803–6814.

Vener M. V., Shenderovich I. G., Rykounov A. A. A qualitative study of the effect of a counterion and polar environment on the structure and spectroscopic signatures of a hydrated hydroxyl anion // Theoretical Chemistry Accounts. — 2013. — Vol. 132. — P. 1361. The results of the qualitative analysis of the effect of a counterion and polar environment on the structure and spectroscopic signatures of a hydrated hydroxyl anion based on DFT/M06-2X calculations in the polarizable cavity approximation reported in this work provide a tool to discriminate between the spectral signatures of the neutral, OH-(nH2O) B+, and anionic, OH-(nH2O), solvation clusters in aqueous solutions of alkali metal (B) hydroxides. These results demonstrate also that the precisions of the available experimental data and of the double harmonic approximation are insufficient to attribute the experimental spectral signatures to any specific cluster with the certain number of involved water molecules at least for 2 < n < 7. [ DOI ]

Cl center dot center dot center dot cl interactions in molecular crystals: Insights from the theoretical charge density analysis / M. V. Vener, A. V. Shishkina, A. A. Rykounov, V. G. Tsirelson // The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. — 2013. — Vol. 117, no. 35. — P. 8459–8467. [ DOI ]

Noncovalent interactions in crystalline picolinic acid n-oxide: Insights from experimental and theoretical charge density analysis / A. V. Shishkina, V. V. Zhurov, A. I. Stash et al. // Crystal Growth and Design. — 2013. — Vol. 13, no. 2. — P. 816–828.

Strong is hydrogen bonding in ionic liquids? combined x-ray crystallographic, infrared/raman spectroscopic, and density functional theory study / S. A. Katsyuba, M. V. Vener, E. E. Zvereva et al. // Journal of Physical Chemistry B. — 2013. — Vol. 117. — P. 9094–9105. Hydrogen bonding in ionic liquids based on the 1-(2′-hydroxylethyl)-3-methylimidazolium cation ([C2OHmim]+) and various anions ([A]−) of differing H-bond acceptor strength, viz. hexafluorophosphate [PF6]−, tetrafluoroborate [BF4]−, bis-(trifluoromethanesulfonimide) [Tf2N]−, trifluoromethylsulfonate [OTf]−, and trifluoroacetate [TFA]−, was studied by a range of spectroscopic and computational techniques and, in the case of [C2OHmim][PF6], by single crystal X-ray diffraction. T. [ DOI ]

Intermolecular hydrogen bond energies in crystals evaluated using electron density properties: Dft computations with periodic boundary conditions / M. V. Vener, A. N. Egorova, V. G. Tsirelson, A. V. Churakov // Journal of Computational Chemistry. — 2012. — Vol. 33. — P. 2303–2309.

Intermolecular hydrogen bond energies in crystals evaluated using electron density properties: Dft computations with periodic boundary conditions / M. V. Vener, A. N. Egorova, A. V. Churakov, V. G. Tsirelson // Journal of Computational Chemistry. — 2012. — Vol. 33, no. 29. — P. 2303–2309. [ DOI ]

Qtaimc study of the x-h/h center dot center dot center dot o bond order indices (x = o, n, c) in molecular systems / E. V. Bartashevich, D. K. Nikulov, M. V. Vener, V. G. Tsirelson // Computational and Theoretical Chemistry. — 2011. — Vol. 973, no. 1-3. — P. 33–39. [ DOI ]

Dft study of h-bonds in the peptide secondary structures: The backbone-side-chain and polar side-chains interactions / M. V. Vener, A. N. Egorova, D. P. Fomin, V. G. Tsirelson // Journal of Molecular Structure. — 2010. — Vol. 972, no. 1-3. — P. 11–15. [ DOI ]

Vener M. V., Egorova A. N., Tsirelson V. G. Hydrogen bonds and o center dot center dot center dot o interactions in proton-ordered ices. dft computations with periodic boundary conditions // Chemical Physics Letters. — 2010. — Vol. 500, no. 4-6. — P. 272–276. [ DOI ]

A quantum-topological analysis of noncovalent interactions in secondary polyalanine structures / M. V. Vener, A. N. Egorova, D. P. Fomin, V. G. Tsirel'Son // Russian Journal of Physical Chemistry B. — 2009. — Vol. 3. — P. 541–547.

Hierarchy of the non-covalent interactions in the alanine-based secondary structures. dft study of the frequency shifts and electron-density features / M. V. Vener, A. N. Egorova, D. P. Fomin, V. G. Tsirelson // Journal of Physical Organic Chemistry. — 2009. — Vol. 22, no. 3. — P. 177–185. [ DOI ]

КВАНТОВО-ТОПОЛОГИЧЕСКИЙ АНАЛИЗ НЕКОВАЛЕНТНЫХ ВЗАИМОДЕЙСТВИЙ ВО ВТОРИЧНЫХ СТРУКТУРАХ ПОЛИАЛАНИНА / М. В. Венер, А. Н. Егорова, Д. П. Фомин, В. Г. Цирельсон // Химическая физика. — 2009. — Т. 28. — С. 3–10.

Dft study of proton dynamics in the potassium hydrogen maleate crystal: the infrared versus the inelastic neutron scattering spectra / M. V. Vener, A. V. Manaev, D. Hadzi, V. G. Tsirelson // ZEITSCHRIFT FUR PHYSIKALISCHE CHEMIE-INTERNATIONAL JOURNAL OF RESEARCH IN PHYSICAL CHEMISTRY & CHEMICAL PHYSICS. — 2008. — Vol. 222, no. 8-9. — P. 1349–1358. [ DOI ]

Molecular structure, barriers to internal rotation, and the enthalpy of formation of cumene hydroperoxide phcme2ooh: a dft study / A. N. Egorova, M. V. Vener, I. S. Zhukov et al. // Russian Chemical Bulletin. — 2008. — Vol. 57, no. 6. — P. 1179–1186.

Vener M. V., Manaev A. V., Tsirelson V. G. Proton dynamics in strong (short) intramolecular h-bond. dft study of the kh maleate crystal // The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. — 2008. — Vol. 112, no. 51. — P. 13628–13632. [ DOI ]

КВАНТОВО-ТОПОЛОГИЧЕСКИЙ АНАЛИЗ КОРОТКИХ (СИЛЬНЫХ) ВОДОРОДНЫХ СВЯЗЕЙ В ТРЕХМЕРНЫХ ПЕРИОДИЧЕСКИХ КРИСТАЛЛАХ / М. В. Венер, А. В. Манаев, А. Н. Егорова, В. Г. Цирельсон // Химическая физика. — 2008. — Т. 27. — С. 19–32.

Структура, внутримолекулярные барьеры вращения и энтальпия образования гидропероксида кумола С6Н5С(СН3)2ООН по данным расчетов методами теории функционала плотности / А. Н. Егорова, М. В. Венер, И. С. Жуков и др. // Известия Академии наук. Серия химическая. — 2008. — С. 1157–1164.

Qtaim study of strong h-bonds with the o-h center dot center dot center dot a fragment (a = o, n) in three-dimensional periodical crystals / M. V. Vener, A. V. Manaev, A. N. Egorova, V. G. Tsirelson // The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. — 2007. — Vol. 111, no. 6. — P. 1155–1162. [ DOI ]

Qtaim study of the closed-shell interactions in peptide secondary structures: A cluster treatment of oligo- and polyalanines / M. V. Vener, A. N. Egorova, D. P. Fomin, V. G. Tsirelson // Chemical Physics Letters. — 2007. — Vol. 440, no. 4-6. — P. 279–285. [ DOI ]

КОЛИЧЕСТВЕННЫЙ АНАЛИЗ Н-СВЯЗЕЙ В b-ПЕТЛЯХ НА ОСНОВЕ АЛАНИНА. ЧАСТОТНЫЕ СДВИГИ И ЭЛЕКТРОННЫЕ ХАРАКТЕРИСТИКИ КРИТИЧЕСКИХ ТОЧЕК / М. В. Венер, Д. П. Фомин, А. Н. Егорова, В. Г. Цирельсон // Успехи в химии и химической технологии. — 2007. — Т. 21. — С. 50–54.

Quantum-topological study of short h-bonds with the o..h..o fragment. molecular crystals versus isolated species / M. V. Vener, A. V. Manaev, A. N. Egorova, V. G. Tsirelson // III International Conference on H-bonding and Molecular interactions. Kyiv, Ukraine. Book of abstracts. — 2006. — P. 160.

СТРУКТУРА И ВНУТРИМОЛЕКУЛЯРНЫЕ БАРЬЕРЫ ВРАЩЕНИЯ 1-МЕТИЛ-1-ФЕНИЛ-ЭТИЛ КУМОЛ ГИДРОПЕРОКСИДА С6Н5С(СН3)2ООН ПО ДАННЫМ НЕЭМПИРИЧЕСКИХ РАСЧЕТОВ / А. Н. Егорова, М. В. Венер, И. С. Жуков и др. // Успехи в химии и химической технологии. — 2006. — Т. 20, № 3. — С. 55–59.

Heterogeneous catalytic synthesis and structure of 5,5a,10a,11-tetrahydro-10h-indeno[1,2-b]quinoline / V. PLESHAKOV, K. AMBACHEU, M. RYASHENTSEVA et al. // Russian Chemical Bulletin. — 1994. — Vol. 43, no. 6. — P. 1037–1040. Hydrogenation of 10H-indeno[1,2-b]quinoline in benzene in the presence of R(2)S(7) (250 degrees C, pH(2) = 140 atm, 4 h) gave 5,5a,10a,11-tetrahydro-10H-indeno[1,2-b]quinoline, the structure of which was established by mass-, IR, UV, C-13, and H-1 NMR spectra. The cis fusion of the indan and tetrahydroquinoline fragments, the axial orientation of the proton at C(5a), and the equatorial orientation of the proton at C(10a) were confirmed by molecular mechanics calculations using the PC MODEL program. [ DOI ]

Theoretical-study of homogeneous electron self-exchange in polar aromatic-molecules - the role of the reactant structure / M. VENER, N. IOFFE, A. CHEPRAKOV, V. MAIRANOVSKY // Journal of Electroanalytical Chemistry. — 1994. — Vol. 370, no. 1-2. — P. 33–39.

Structures of lithium salts of substituted 1-phenylpropynes: 13c nmr and mndo study / P. I. Dem’yanov, I. M. Styrkov, D. P. Krut’ko et al. // Journal of Organometallic Chemistry. — 1992. — Vol. 438, no. 3. — P. 265–288. 13C NMR spectroscopy has been used to study the structure of ambident carbanions in contact (CIP) and solvent-separated (SSIP) ion pairs of lithium salts of substituted 1-phenylpropynes. It was shown that the structures of carbanions in SSIP are close to the propargylic type, whereas, with the decrease in delocalizing ability of substituents at the propargylic centre, their structure shifts to the allenylic type, in fair agreement with theoretical predictions by the MNDO semi-empirical method. In CIP, the structures of carbanions are progressively changed from near-to-propargylic to allenylic with decrease of delocalizing ability of the substituents. [ DOI ]

Строение литиевых солей замещ.1-фенилпропинов: C(13)ЯМР и mndo-изучение / П. И. Демьянов, В. С. Петросян, И. М. Штырков и др. // Journal of Organometallic Chemistry. — 1992. — Т. 438. — С. 265.

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