Article
Chemistry, Multidisciplinary
Andrew M. L. West, Nicholas Dominelli-Whiteley, Ivan V. V. Smolyar, Gary S. S. Nichol, Scott L. L. Cockroft
Summary: Crystallographic and computational studies suggest favourable interactions between polarizable arenes and halogen atoms. However, quantification of these interactions in solution has been hindered by the steric demands of the halogens. This study synthesized molecular balances and used H-1 NMR spectroscopy to quantify halogen-arene contacts in various solvents, revealing that the interaction trend is aligned with increasing exchange repulsion rather than dispersion.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ga Young Lee, Elizabeth Hu, Arnold L. Rheingold, K. N. Houk, Ellen M. Sletten
Summary: A systematic study of arene-perfluoroarene interactions in solution reveals that factors such as fluorination, extension of pi systems, and enhancement of solvent polarity significantly influence the stability of stacking energy. Experimental results in aqueous solution show that electrostatic and dispersion interactions, as well as the hydrophobic effect, play key roles in the impressive binding energy observed.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sergey Baykov, Daniil M. Ivanov, Svetlana O. Kasatkina, Bartomeu Galmes, Antonio Frontera, Giuseppe Resnati, Vadim Y. Kukushkin
Summary: The co-crystallization of tetracyanobenzene with haloarenes was studied, and it was found that the stacking interactions and lone pair-pi-hole bonds between the molecules promote the strength of halogen bonding. The stacking interactions increase the ability of haloarenes to act as halogen bonding donors.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Yunying Xu, Aiyou Hao, Pengyao Xing
Summary: This study reports a weak halogen bond type that induces the formation of supramolecular helical structures in both solid and solution states. Experiments with p-conjugated phenylalanine derivatives show that hydrogen bonds and halogen bonds respectively drive 21 helical packings, with small bond energies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Alica C. Keuper, Kevin Fengler, Florian Ostler, Tobias Danelzik, Dariusz G. Piekarski, Olga Garcia Mancheno
Summary: A new approach to achieve highly enantioselective halogen-bonding catalysis has been developed by designing fine-tuned halogen-halogen interactions. This strategy utilizes both the electron cloud and sigma-hole site of the substrate's halogen substituent to form a tight chiral complex, enabling controlled induction of high levels of chirality transfer. Remarkable enantioselectivities of up to 95:5 e.r. (90% ee) have been achieved in a model dearomatization reaction using tetrakis-iodotriazole multidentate anion-binding catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Chaowei Yin, Hanwei Lu, Hebo Ye, Zelin Feng, Hanxun Zou, Meilan Zhang, Lei You
Summary: This study presents double n -> nr* interactions between one common electron donor of the carbonyl oxygen and two individual acceptor aldehyde/imine units. The orientation and energetic dependence of orbital interactions were regulated by the size of cyclic urea scaffolds, the bulkiness of aldehydes/imines, and the flexibility of imine macrocycles, as revealed by experimental and computational evidence.
Article
Chemistry, Multidisciplinary
Michio Yamada, Yukiyo Kurihara, Masaaki Koizumi, Kasumi Tsuji, Yutaka Maeda, Mitsuaki Suzuki
Summary: In this study, a fullerene-based torsion balance was used as a model system to quantify noncovalent interactions between arenes and the fullerene surface. The folding equilibrium was analyzed to measure the contributions of different factors to the interactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Steven van Terwingen, Ruimin Wang, Ulli Englert
Summary: The ditopic molecule HacacMePz combines two different Lewis basic sites and forms a crystalline adduct with TFDIB, showing additional short contacts.
Article
Chemistry, Multidisciplinary
Jiyu Sun, Daniel A. Decato, Vyacheslav S. Bryantsev, Eric A. John, Orion B. Berryman
Summary: This study systematically investigates the substituent effects in the HBeXB. NMR analysis and gas-phase density functional theory studies reveal the influence of HBing on the halogen atom and the effect of different substituents on the XB donor ring. The findings suggest that modifying distal substituents can enhance an electron-rich XB donor.
Article
Chemistry, Multidisciplinary
Tanmoy Basak, Antonio Frontera, Shouvik Chattopadhyay
Summary: The hydrogen bonding interactions and halogen bonding interactions in two mononuclear iron(III) complexes have been studied and analyzed using DFT and QTAIM calculations.
Article
Chemistry, Multidisciplinary
Felix Otte, Johannes Kleinheider, Wolf Hiller, Ruimin Wang, Ulli Englert, Carsten Strohmann
Summary: The halogen bonded adduct between quinuclidine and iodobenzene exhibits the longest N·I molecular halogen bond with a distance of 2.9301(4) angstrom. Topological analysis identified XB as a directional but weak 6-hole interaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Sibali Debnath, Krishnan Raghavachari
Summary: This study investigates the noncovalent forces involved in the self-assembly of tricarb macrocycles and reveals the major contributing interactions through computational analysis. The results obtained shed light on the stability and construction of 3D structures in tricarb and related compounds.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Chemistry, Multidisciplinary
Rakesh Puttreddy, J. Mikko Rautiainen, Shilin Yu, Kari Rissanen
Summary: The N-X...O--N+ halogen-bonded systems formed by pyridine N-oxides (PyNOs) as halogen-bond acceptors and N-halosuccinimides, N-halophthalimides, and N-halosaccharins as donors are studied. A simple electrostatic model for predicting XB energies using only the properties of halogen donors and oxygen acceptors is developed. Data from in silico bond energies and single-crystal X-ray structures correlate, but data from solution do not.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Inorganic & Nuclear
Pounraj Thanasekaran, Cing-Huei Su, Yen-Hsiang Liu, Kuang-Lieh Lu
Summary: The article highlights the importance of weak interactions in metal-organic frameworks (MOFs) and recent advancements in inducing high conductivity through through-bond and through-space strategies. By utilizing strong orbital overlap bonding and integrating metal-organic linkers within MOFs, conductivity can be induced in typically poor conductive MOFs. Additionally, weak interactions such as p-p stacking, donor-acceptor interactions, hydrogen bonding, and redox pathways play a crucial role in altering the conductivity of MOFs.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Engineering, Environmental
Chaoke Liu, Yannan Zhou, Tengyue Li, Huayi Zhou, Mingliang Xie, Lizhi Chu, Qikun Sun, Shi-Tong Zhang, Wenjun Yang, Shanfeng Xue
Summary: Developing high-performance nondoped deep-blue luminescent materials for OLEDs is important yet challenging. In this study, two highly efficient pure-blue and deep-blue materials, PIPMePBO and PIPDMePBO, were designed and synthesized. The double-methyl-substituted PIPDMePBO showed nondoped deep-blue electroluminescence with high external quantum efficiency (8.0%) and minimal efficiency roll-off (approximately 12%).
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Mikhail A. A. Kinzhalov, Daniil M. M. Ivanov, Anastasia V. V. Shishkina, Anna A. A. Melekhova, Vitalii V. V. Suslonov, Antonio Frontera, Vadim Yu. Kukushkin, Nadezhda A. A. Bokach
Summary: Crystallization of [CuI(CNXyl)(3)] (1) with I-2 resulted in the formation of a series of (XylNC)Cu-I crystal polyiodides, along with the accumulation of iodine. The compounds [Cu(I-3)(CNXyl)(3)] (2(I) and 2(II)), [Cu(I-3)(CNXyl)(3)]center dot 1/2I(2) (2 center dot 1/2I(2)), and [Cu(CNXyl)(3)](I-5) (3) were studied by X-ray diffractometry. The presence of an I-2?I-3(-) halogen bonded linkage in the structure of 2 center dot 1/2I(2) provides insight into the mechanism for the generation of I-5(-) and I-8(2-) ligands from I-2 and metal-coordinated I-3(-).
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Anton V. V. Rozhkov, Eugene A. A. Katlenok, Margarita V. V. Zhmykhova, Maxim L. L. Kuznetsov, Victor N. N. Khrustalev, Kirill I. I. Tugashov, Nadezhda A. A. Bokach, Vadim Yu. Kukushkin
Summary: This study investigates the properties of platinum(II) complexes and anticrown cocrystals with stacked heteroplanar architectures. The results demonstrate that the spodium bonds between Hg···Pt and Hg···C play a crucial role in controlling the stacking orientation. Heteroplanar stacking enhances the phosphorescence lifetimes and solid-state quantum yield.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biochemistry & Molecular Biology
Kira V. V. Derkach, Maxim A. A. Gureev, Anastasia A. A. Babushkina, Vladimir N. N. Mikhaylov, Irina O. O. Zakharova, Andrey A. A. Bakhtyukov, Viktor N. N. Sorokoumov, Alexander S. S. Novikov, Mikhail Krasavin, Alexander O. O. Shpakov, Irina A. A. Balova
Summary: This article describes the identification of dual inhibitors of protein phosphotyrosine phosphatase 1B (PTP1B)/T-cell protein phosphotyrosine phosphatase (TC-PTP) based on the 3-(hydroxymethyl)-4-oxo-1,4-dihydrocinnoline scaffold. The compounds were evaluated for their effects on obesity-related parameters and gene expressions. The results indicate the potential of these compounds as dual inhibitors for the treatment of metabolic disorders.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Dmitry S. S. Suslov, Mikhail V. V. Bykov, Marina V. V. Pakhomova, Timur S. S. Orlov, Zorikto D. D. Abramov, Anastasia V. V. Suchkova, Igor A. A. Ushakov, Pavel A. A. Abramov, Alexander S. S. Novikov
Summary: The Pd(II) complexes [Pd(Cp)(L)(n)](m)[BF4](m) were synthesized by reacting cationic acetylacetonate complexes with cyclopentadiene in the presence of BF3 center dot OEt2. X-ray diffraction analysis confirmed the structures of complexes 1-3 and revealed non-covalent C-H center dot center dot center dot pi interactions. DFT calculations and QTAIM analysis supported the existence of these interactions. The cationic Pd catalyst precursors with monophosphines showed high catalytic activity for the telomerization of 1,3-butadiene with methanol, and complex [Pd(Cp)(TOMPP)(2)]BF4 exhibited efficient catalytic activity for the polymerization of phenylacetylene.
Article
Pharmacology & Pharmacy
Yulia S. Bortnevskaya, Nikita A. Shiryaev, Nikita S. Zakharov, Oleg O. Kitoroage, Margarita A. Gradova, Natalia Yu. Karpechenko, Alexander S. Novikov, Elena D. Nikolskaya, Mariia R. Mollaeva, Nikita G. Yabbarov, Natal'ya A. Bragina, Kseniya A. Zhdanova
Summary: Photodynamic therapy (PDT) in oncology is a minimally invasive treatment option for cancer with minimal side effects and tissue scarring. This study focuses on the development and characterization of a new conjugate based on meso-arylporphyrin and a low-molecular-weight tyrosine kinase inhibitor, Erlotinib. A nano-formulation based on Pluronic F127 micelles was successfully prepared. The conjugate nanomicelles showed significantly enhanced activity and toxicity towards EGFR-overexpressing cancer cells compared to normal cells after irradiation.
Article
Biochemistry & Molecular Biology
Nikolai F. Romashev, Ivan V. Bakaev, Veronika I. Komlyagina, Pavel A. Abramov, Irina V. Mirzaeva, Vladimir A. Nadolinny, Alexander N. Lavrov, Nikolai B. Kompan'kov, Artem A. Mikhailov, Iakov S. Fomenko, Alexander S. Novikov, Maxim N. Sokolov, Artem L. Gushchin
Summary: A series of iridium complexes with dpp-bian ligands were synthesized and characterized. The structures of the complexes exhibit a square planar backbone consisting of cod, dpp-bian, and a chloride ion (for 1) or a NO group (for 2). Complex 2 is unstable in solution and decomposes to form complex 4. Magnetic measurements of complex 2 show an increase in magnetic moment with temperature. DFT calculations support the experimental observations.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Anatoly A. Peshkov, Diana Gapanenok, Aleksandra Puzyk, Niyaz Amire, Alexander S. Novikov, Sofia D. Martynova, Stanislav Kalinin, Dmitry Dar'in, Vsevolod A. Peshkov, Mikhail Krasavin
Summary: A chemoselective strategy for the synthesis of various fused heterocycles was developed using a three-component condensation reaction of heterocyclic ketene aminals (HKAs) or corresponding thioaminals with aryl glyoxals and cyclic 1,3-dicarbonyl compounds. Depending on the combination of substrates, this strategy allows the straightforward access to imidazo[1,2-a]quinoline, pyrrolo[1,2-a]imidazole, and pyrrolo[2,1-b]thiazole frameworks.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Ekaterina A. Lystsova, Alexander S. Novikov, Maksim V. Dmitriev, Andrey N. Maslivets, Ekaterina E. Khramtsova
Summary: Acyl(imidoyl)ketenes can be used to synthesize diverse drug-like heterocycles. By utilizing the [4+2]-cyclodimerization of acyl(1,3-benzothiazol-2-yl)ketenes, a new synthetic approach to pharmaceutically interesting pyrido[2,1-b][1,3]benzothiazol-1-ones has been developed. Thermal analysis and computational studies revealed the suitability of 3-aroylpyrrolo[2,1-c][1,4]benzothiazine-1,2,4-triones as a source of acyl(1,3-benzothiazol-2-yl)ketenes, and a novel mode of thermal transformation of [e]-fused 1H-pyrrole-2,3-diones was discovered. The synthesized pyrido[2,1-b][1,3]benzothiazol-1-ones are of interest due to their potential antiviral activity.
Editorial Material
Multidisciplinary Sciences
Alexander S. Novikov
Article
Chemistry, Physical
Valentine G. Nenajdenko, Anna A. Kazakova, Alexander S. Novikov, Namig G. Shikhaliyev, Abel M. Maharramov, Ayten M. Qajar, Gulnar T. Atakishiyeva, Aytan A. Niyazova, Victor N. Khrustalev, Alexey V. Shastin, Alexander G. Tskhovrebov
Summary: The copper catalyzed reaction of N-monosubstituted hydrazones with carbon tetrabromide leads to the formation of expected dibromodiazadienes and unexpected dibromostyrenes. The key role of N-centered radicals in the reaction was revealed through experimental and theoretical studies, where they can eliminate aryl radicals to form dibromostyrenes. Alternatively, the oxidation of intermediate N-centered radicals by Cu(II) results in the formation of diazadienes. These two reaction pathways are competitive directions of the reaction, making it useful for the synthesis of both dibromostyrenes and rare dibromodiazadienes.
Article
Crystallography
Ivan V. Moskalenko, Vladimir V. Shilovskikh, Pavel V. Nesterov, Alexander S. Novikov, Malika Omarova, Roman V. Sadovnichii, Vladislav V. Gurzhiy, Nikita D. Orekhov, Ekaterina V. Skorb
Summary: This work explores the formation of supramolecular assemblies of melamine-thiobarbiturate and melamine-barbiturate-thiobarbiturate. Various experimental techniques were used to study the resulting crystals, and theoretical simulations were performed to analyze these systems. The study reveals that hydrogen from thiobarbituric acid migrates to the melamine molecule during the crystallization process, and different crystals exhibit different fluorescence behaviors.
Article
Chemistry, Multidisciplinary
Ivan V. Moskalenko, Leonid I. Borodin, Alexander S. Novikov
Summary: This article discusses the oxidation of methyl linoleate in micelles initiated by lipid-soluble initiator AMVN. It was found that the initiation rate constant (k(i)) of AMVN in micelles is significantly lower than in true solutions. This can be explained by the reduced probability of AMVN radicals leaving the cage and an increase in the rate of chain termination under low oxygen conditions. Quantum chemical calculations confirm this conclusion. Surprisingly, the initiation rate constant of AMVN for the consumption of nitroxyl radicals (>NO center dot) depends on the >NO center dot concentration, due to the probability of nitroxyl radicals and initiator radicals meeting in micelles being dependent on their concentration. No hydroperoxyl radicals are expelled upon AMVN initiation.
Article
Chemistry, Organic
Amirbek D. Radzhabov, Natalia S. Soldatova, Daniil M. Ivanov, Mekhman S. Yusubov, Vadim Yu. Kukushkin, Pavel S. Postnikov
Summary: We have developed an efficient strategy for the synthesis of diarylselenides using iodonium salts as reactants. This method allows the conversion of trimethoxyphenyl-substituted iodonium salts to diarylselenides in a two-step one-pot reaction sequence. The reaction involves the participation of both iodonium aryl groups for diarylation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Eugene A. Katlenok, Maxim L. Kuznetsov, Anton V. Cherkasov, Dmitry M. Kryukov, Nadezhda A. Bokach, Vadim Yu. Kukushkin
Summary: By using X-ray crystallography, the cocrystals 1 center dot C6F6, 2 center dot C6F6, and 1 center dot(OFA)(2) were obtained by crystallizing the half-lantern Pt-2(II) complexes with electron-deficient arenes. The structural data revealed the occurrence of π-π stacking between the arenes and metal square-planes. Density functional theory calculations and orbital interaction analysis confirmed the contribution of noncovalent bonding and charge-transfer interaction in the overall stacking forces.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Eugene A. Katlenok, Maxim L. Kuznetsov, Anton V. Cherkasov, Dmitry M. Kryukov, Nadezhda A. Bokach, Vadim Yu. Kukushkin
Summary: In this study, it was observed by X-ray crystallography that the Pt-2(II) complexes form crystals with electron-deficient arenes, and it was verified that there is a π-π stacking interaction between the arenes and the metal square-planes. Density functional theory calculations confirmed the contribution of the noncovalent bond between the arenes and Pt(II) in the overall stacking forces. Orbital interaction analysis demonstrated the significance of the charge-transfer interaction between d(z)(2)(Pt) and pi*(C), attributing the C.Pt contact to a metal-involved tetrel bonding. Many-body interaction analysis showed a positive cooperative effect between the fragments of the half-lantern complex and the perfluoroarenes favoring the occurrence of supramolecular chains.
INORGANIC CHEMISTRY FRONTIERS
(2023)