Article
Chemistry, Organic
Michel Chiarucci, Andrea Mazzanti, Paolo Righi, Giorgio Bencivenni, Michele Mancinelli
Summary: A series of 1,8-bis(1-naphthyl)-naphthalenes with different substituents have been synthesized to investigate noncovalent interactions between stacked arenes. DFT calculations, NMR, and ECD experiments were used to determine the best geometries and understand the role of dispersive and electrostatic contributions. The study revealed that electrostatic contributions greatly influence the interaction energy of the two naphthyl rings, while dispersive forces play a minor role in determining the parallel displaced geometry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Crystallography
R. Alan Aitken, Alexander J. B. Nelson, Alexandra M. Z. Slawin, Dheirya K. Sonecha
Summary: Thirteen new crystal structures of cyclic NH carboximides have been determined and compared based on their intermolecular hydrogen bonding patterns. The structures include a new cyclobutane-fused succinimide, seven new simple bi- and tricyclic succinimides derived from Diels-Alder reactions, three methylated glutarimides, a morpholinedione and adipimide, and the first seven-membered ring NH carboximide to be characterized. The compounds were found to adopt ribbon structures, centrosymmetric dimers, and bonding between NH and a remote bridging ether oxygen. Halogen bonding was also observed in one case.
Review
Chemistry, Physical
Cuc Kim Trinh, Nabiha Abdo
Summary: Research on small molecules-based optoelectronic devices has shown that improving device performance can be achieved by increasing the conjugation length in organic semiconductors, extending molecular ordering and intermolecular interactions through hydrogen bonding. However, solubility remains a challenge for the application of these materials, and cleavable protecting groups are used to address this issue.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Physical
Akhilesh Kumar, Ranjeet Kumar, Rashmi Dubey, Manisha Nidhar, Indresh Verma, Praveen Singh, Ashish Kumar Tewari
Summary: The synthesis and characterization of pyridazine and triazine derivatives containing amide functional group were carried out to study the formation of amide-amide hydrogen-bonded synthons. Supramolecular synthons formations in solid state were investigated using x-ray crystallography and Hirshfeld surface analysis. The crystal structure and Hirshfeld surface analysis revealed that the synthons formation occurred through N-HMIDLINE HORIZONTAL ELLIPSISO interactions and other interactions that stabilized the molecules. In addition, insilico studies were conducted for COX-2 selective inhibitor.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Alessandro Triolo, Annalisa Paolone, Angelo Sarra, Francesco Trequattrini, Oriele Palumbo, Giovanni BattistaAppetecchi, Fabrizio Lo Celso, Philip Chater, Olga Russina
Summary: The chemical and physical properties as well as the structural features of a Protic Ionic Liquid (PIL) formed by neutralization of a super-strong base with a super-strong acid have been investigated in this study. The role of hydrogen bonding (HB) in affecting the morphology of the PIL has been highlighted, and a comparison between HB features in this PIL and related PILs has been presented. Differences in HB interaction have been observed and explained based on the geometrical properties of the main conformers contributing to the experimental spectra.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Chemistry, Organic
Andrey V. Marchenko, Valery A. Ozeryanskii, Oleg P. Demidov, Alexander S. Antonov, Elena Yu. Tupikina, Alexander F. Pozharskii
Summary: The lithiation reaction of 2,7-disubstituted derivatives of 1,8-bis(dimethylamino)naphthalene (DMAN) bearing OMe, NMe2, and SMe groups was studied. It was found that OMe groups facilitate the selective dual beta-lithiation of the naphthalene moiety, while NMe2 groups allow only monolithiation due to decreased acidity and conformational immobilization. SMe groups do not undergo ring lithiation but undergo deprotonation. The synthesis of previously unknown 2,3,6,7-tetrasubstituted DMANs was achieved, providing the first opportunity to study the double buttressing effect (BE) version.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Caixin Zhao, Kai Chen, Weiwei Yang, Zhiyun Zhang, Da-Hui Qu
Summary: This study reports on the reversible mechanochromic luminescence property of (dibenzo[a,c]phenazine-9,14-diylbis (4,1-phenylene))dimethanol (DPAC-OH). The photoluminescent color changes from blue to blue-green upon grinding and can be restored upon slow solvent evaporation. The role of hydrogen bonding in DPAC-OH is further demonstrated using the control sample 9,14-bis(4-(methoxymethyl)phenyl)9,14-dihydrodibenzo[a,c]phenazine (DPAC-OCH3). The mechanochromic phenomenon is attributed to the vibration-induced emission (VIE) mechanism and the presence of hydrogen bonding interactions.
Article
Chemistry, Organic
Ekaterina A. Filatova, Eugeny A. Ermolenko, Alexander F. Pozharskii, Valery A. Ozeryanskii, Oleg P. Demidov, Anatoly V. Chernyshev, Anatoly V. Metelitsa, Anna V. Gulevskaya
Summary: 4-Bromo- and 4,5-dibromo-1,8-bis(dimethylamino)naphthalenes were arylated under Suzuki reaction conditions to provide 4-aryl- and 4,5-diaryl-1,8-bis(dimethylamino)naphthalenes, respectively. Unexpected heterocyclization occurred during the interaction of 4,5-dibromo-1,8-bis(dimethylamino)naphthalene with pyridin-3-ylboronic acid, resulting in the formation of N-3,N-3,N-4,N-4-tetramethylacenaphtho[1,2-b]pyridine-3,4-diamine. The rotational isomerization of 4,5-diaryl-1,8-bis(dimethylamino)naphthalenes was studied, and it was found that the introduction of peri-aryl substituents affected the basic properties and structural deformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Nanoscience & Nanotechnology
David H. Wang, Kyung Min Lee, Deborah H. Lee, Matthew Baczkowski, Jae Gyeong Lee, Jeong Jae Wie, Loon-Seng Tan
Summary: In this research, a series of azobenzene-functionalized amide-imide block copolymers were studied for their photomechanical properties, revealing complex composition dependencies. As the content of amide blocks increases, certain properties exhibit a trend of decreasing first and then increasing, which is correlated with the formation and dissociation of hydrogen bonds.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Organic
Takuya Murai, Yongning Xing, Mayu Kurokawa, Toshifumi Kuribayashi, Masanori Nikaido, Elghareeb E. Elboray, Shohei Hamada, Yusuke Kobayashi, Takahiro Sasamori, Takeo Kawabata, Takumi Furuta
Summary: A one-pot transformation method has been developed to convert biaryl dicarboxylic acids to (NH)-phenanthridinone derivatives using Curtius rearrangement and subsequent basic hydrolysis. This method is also applicable for preparing optically active amide-functionalized [7]helicene-like molecules. In addition, aza[5]helicene derivatives with a phosphate moiety were obtained as products of the Curtius rearrangement step when chalcogen atoms were present in the substrates. X-ray diffraction analysis revealed that chalcogen-bonding and pnictogen-bonding interactions may contribute to the stabilization of these compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Alexander F. Pozharskii, Olga Dyablo, Valery A. Ozeryanskii, Olga G. Pogosova
Summary: The review summarizes the progress made in understanding NH center dot center dot center dot pi interactions, which play a significant role in the structuring of proteins, molecular recognition, and drug development. The study of these interactions contributes to a better understanding of complex biochemical processes and the development of targeted drug delivery methods. The review discusses various models and provides examples of reactions and practical applications.
RUSSIAN CHEMICAL REVIEWS
(2022)
Article
Chemistry, Physical
Xiaoyang Liu, C. Turner
Summary: This study uses quantum chemical calculations to delineate different fundamental interactions in water-solvent systems, with a particular focus on the role of electrostatic potential characteristics. This has important implications for improving solvent design to enhance solvent extraction desalination technology.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Chemistry, Physical
Anu Jain, Ritutama Ghosh, Nand Kishore
Summary: Quantitative study of drug-drug interaction is essential for understanding the effectiveness and safety of drugs. In this research, the interaction of naproxen with various drugs was studied using ultrasensitive isothermal titration calorimetry and uv-absorbance spectroscopy. The results show that most drugs have weak interactions with naproxen, while L-ascorbic acid shows the strongest interaction. The correlation between thermodynamic parameters and the number of hydrogen bonding groups in the drugs indicates that an increase in hydrogen bonding groups leads to a decrease in drug-drug interaction strength.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Medicine, Research & Experimental
Chailu Que, Alexandru Deac, Dmitry Y. Zemlyanov, QingQing Qi, Anura S. Indulkar, Yi Gao, Geoff G. Z. Zhang, Lynne S. Taylor
Summary: This study investigated the relationship between drug chemical structure and the limit of congruency (LoC) in PVPVA-based ASDs. Different types of drug-polymer interactions were found to impact the dissolution performance of ASDs, providing insights into the role of drug and polymer chemical structures on LoC and ASD performance in general.
MOLECULAR PHARMACEUTICS
(2021)
Article
Chemistry, Multidisciplinary
Eleonora Veronese, Claudia Pigliacelli, Greta Bergamaschi, Giancarlo Terraneo, Valentina Dichiarante, Pierangelo Metrangolo
Summary: By selecting Fmoc-pentafluorophenylalanine as a model efficient gelator and studying its self-assembly in the presence of benzamide, a 1:1 co-crystal was obtained, which can form transparent gels in aqueous media. This crystal engineering-based approach can be used for modulating the properties of amino acid-based hydrogels and for the time-delayed release of suitable bioactive molecules.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Jesse B. Gordon, Therese Albert, Sudha Yadav, Jithin Thomas, Maxime A. Siegler, Pierre Moenne-Loccoz, David P. Goldberg
Summary: A five-coordinate cobalt(II) complex with disiloxide ligands was synthesized and its structural and spectroscopic properties were analyzed. The complex was found to reversibly bind and release oxygen at low temperatures. The reactivity of the complex towards hydrogen atom abstraction was studied and compared to its sulfur-ligated analogue.
INORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Run-Duo Gao, Michelle Taylor, Tamara McInnis, Zhenglan Chen, Sadakatali S. Gori, Heather M. LaPorte, Maxime A. Siegler, Janet L. Neisewander, Robert H. Mach, Meharvan Singh, Barbara S. Slusher, Rana Rais, Robert R. Luedtke, Takashi Tsukamoto
Summary: Reduced haloperidol (1) acts as a potent S1R ligand with lower affinity to D2R and facilitates BDNF secretion. However, its therapeutic utility is limited due to oxidation back to haloperidol, which has adverse effects. A difluorinated analogue (2) was synthesized to minimize oxidation and was found to exhibit high affinity to S1R and promote BDNF release. Compound 2 distributed to the brain, reversed learning deficits, and shows promise for the treatment of cognitive impairments.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Muhammad Kazim, Zhitao Feng, Srini Vemulapalli, Maxime A. Siegler, Anant Chopra, Phuong Minh Nguyen, Maxwell Gargiulo Holl, Liangyu Guan, Travis Dudding, Dean J. Tantillo, Thomas Lectka
Summary: We conducted a detailed analysis of through-space arene activation with halogens, tetrazoles, and achiral esters and amides, both experimentally and theoretically. Contrary to previous assumptions, our findings indicate that these reactions proceed through a relay mechanism, with lone pair-containing activators forming exothermic π-complexes with electrophilic nitronium ions before transferring them to the probe ring through low barrier transition states. The involvement of noncovalent interactions and directing group participation throughout the mechanism is supported by NCI plots and QTAIM analyses. Overall, this study opens up possibilities for an alternate platform of electrophilic aromatic substitution reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Inorganic & Nuclear
Daan den Boer, Andrey I. Konovalov, Maxime A. Siegler, Dennis G. H. Hetterscheid
Summary: To enhance Cu-based water oxidation catalysts, a comprehensive understanding of their mechanistic pathways is necessary. Unlike other metals, Cu-catalyzed WO does not involve high-oxidation-state metal-oxo species due to the challenging pi donation from the oxo ligand to Cu-II and Cu-III. Instead, an alternative WO mechanism occurs in these systems.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Matthijs L. A. Hakkennes, Michael S. Meijer, Jan Paul Menzel, Anne-Charlotte Goetz, Roy Van Duijn, Maxime A. Siegler, Francesco Buda, Sylvestre Bonnet
Summary: The selectivity of photosubstitution reactions of sterically strained ruthenium(II) polypyridyl complexes, carrying diimine chelates, in water and acetonitrile was investigated experimentally and computationally. The rigidity of the chelates played a crucial role in determining the selectivity, and the solvent also influenced the ratio of different photoproducts. Three reaction pathways leading to photodissociation were identified on the triplet surface, and the temperature variation of the photosubstitution quantum yield was used to compare theory with experiments.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Correction
Chemistry, Multidisciplinary
Jesse B. Gordon, Therese Albert, Aniruddha Dey, Sinan Sabuncu, Maxime A. Siegler, Eckhard Bill, Pierre Moenne-Loccoz, David P. Goldberg
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Bohee Kim, Magdalene T. T. Brueggemeyer, Wesley J. J. Transue, Younwoo Park, Jaeheung Cho, Maxime A. A. Siegler, Edward I. I. Solomon, Kenneth D. D. Karlin
Summary: Lytic polysaccharide monooxygenases are important in converting biomass to biofuel, and recent studies show that their peroxygenase activity using H2O2 as an oxidant is more important than their monooxygenase functionality. New insights into this activity have been described, including ligand-substrate hydroxylation and Fenton-type chemistry reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Herbert Wakefield, Ilia Kevlishvili, Kelsie E. Wentz, Yunxin Yao, Tatiana B. Kouznetsova, Sophia J. Melvin, Em G. Ambrosius, Abraham Herzog-Arbeitman, Maxime A. Siegler, Jeremiah A. Johnson, Stephen L. Craig, Heather J. Kulik, Rebekka S. Klausen
Summary: The cis- and trans-isomers of a silacycloheptene were selectively synthesized using a silyl dianion, providing a novel method for studying strained cycloalkenes. Quantum chemical calculations and crystallographic signatures confirmed that the trans-isomer is more strained than the cis isomer. The trans-isomer also exhibited unique reactivity in ring-opening metathesis polymerization (ROMP) and showed increased molecular compliance compared to carbon-based analogues.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Muhammad Kazim, Muyuan Wang, Srini Vemulapalli, Phuong Minh Nguyen, Yuang Wang, Maxime A. Siegler, Travis Dudding, Thomas Lectka
Summary: We have found that face-to-face pi-stacked aromatic rings activate each other towards electrophilic aromatic substitution through direct influence of the adjacent stacked ring. This activation occurs even when one of the rings is deactivated through nitration. The resulting dinitrated products crystallize in an extended parallel offset stacked form, contrasting the substrate.
Article
Materials Science, Multidisciplinary
Huiyuan Man, Alireza Ghasemi, Moein Adnani, Maxime A. Siegler, Elaf A. Anber, Yufan Li, Chia-Ling Chien, Mitra L. Taheri, Ching-Wu Chu, Collin L. Broholm, Seyed M. Koohpayeh
Summary: Little is known about the magnetism of A(2)B(2)O(7) monoclinic layered perovskites. The study investigates the chemical phase stability, structure, and magnetic properties of Pr2Ti2O7. It is found that Pr2Ti2O7 forms a singlet ground state quantum paramagnet that does not undergo any magnetic phase transitions.
PHYSICAL REVIEW MATERIALS
(2023)
Review
Chemistry, Multidisciplinary
Muhammad Kazim, Euna Yoo
Summary: In the past two decades, there has been a significant revolution in tumor immunology, with clinical progress in various immunotherapy strategies. These advancements have highlighted the potential of harnessing the immune system to fight against cancer. However, the complex and heterogeneous nature of tumors and immune responses result in varying patient responses, emphasizing the need for reliable biomarkers and therapeutic strategies to maximize the benefits of immunotherapy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Crystallography
Lucas A. Pressley, Hector K. Vivanco, Tanya Berry, Maxime A. Siegler, Tyrel M. McQueen
Summary: The use of configurational entropy has facilitated the customization of oxides for various technological applications. High entropy oxides (HEO) are being explored for magnetocaloric refrigeration due to their tunable spin glass phase. Single crystals of perovskite SmCo1/4Cr1/4Fe1/4Mn1/4O3 were grown using the laser diode floating zone technique to gain a deeper understanding of the magnetic interactions. The material exhibited unique magnetic behaviors and spin canting of transition metal ions, and heat capacity measurements were used to study the low temperature superexchange interactions.
JOURNAL OF CRYSTAL GROWTH
(2023)
Article
Chemistry, Physical
Lucas A. Pressley, Mekhola Sinha, Maxime A. Siegler, Noah Edmiston, Shannon Bernier, Austin M. Ferrenti, Sujit Das, Ramamoorthy Ramesh, Satya Kushwaha, Tyrel M. Mcqueen
Summary: In this study, single crystals of Bi2WO6 with tunable W5+ centers were successfully grown using the floating zone technique, showing potential applications in photocatalysis and quantum information.
JOURNAL OF PHYSICAL CHEMISTRY C
(2023)
Article
Chemistry, Inorganic & Nuclear
Michiel Langerman, Phebe H. van Langevelde, Johannes J. van de Vijver, Maxime A. Siegler, Dennis G. H. Hetterscheid
Summary: Changes in the electronic structure of copper complexes have a significant impact on the catalytic rates, selectivity, and overpotential of electrocatalytic reactions. The half-wave potential (E-1/2) of the Cu-II/Cu-I redox couples is found to be linearly related to the maximum rate constant of oxygen and hydrogen peroxide reduction. The computed binding constants of O-2 to Cu-I also correlate with E-1/2. Catalysts with more negative E-1/2 values exhibit higher catalytic rates, while complexes with more positive E-1/2 values show lower overpotentials. The E-1/2 is an important descriptor in copper-mediated O-2 reduction and affects the selectivity of the catalytic reactions.
INORGANIC CHEMISTRY
(2023)