Article
Chemistry, Multidisciplinary
Miklos H. Bosits, Almos Orosz, Zsofia Szalay, Hajnalka Pataki, Botond Szilagyi, Adam Demeter
Summary: Diastereomeric salt crystallization is a classical technique used to separate enantiomers. In this study, a resolution method for racemic pregabalin with L-tartaric acid was developed to obtain pure (S)-pregabalin L-tartrate monohydrate crystals. The crystallization kinetics were estimated using population balance modeling with different cooling rates and temperature end points.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Multidisciplinary
Laura Bereczki, Amit Zodge, Marton Korosi, Tamas Holczbauer, Sourav De, Edit Szekely, Petra Bombicz
Summary: This study successfully elucidated the structures of two constitutional isomer double salts and their related diastereomeric salt pairs, providing deeper insights into chiral recognition and synthon engineering mastery. The crystal structures and thermal properties of all diastereomers and double salts were determined and analyzed comparatively, revealing a detailed landscape of the effect of stereochemistry on the solid-state structure of the salts.
Article
Chemistry, Multidisciplinary
Miklos H. Bosits, Laura Bereczki, Petra Bombicz, Zsofia Szalay, Hajnalka Pataki, Adam Demeter
Summary: Diastereomeric salt crystallization was used to resolve chiral drug substances, specifically the racemate-forming compound pregabalin, in a quaternary system with l-tartaric acid and water. Solubilities and solid-liquid equilibria were measured and a thermodynamic model based on solubility product constants was created to simulate the resolution process. Optimal temperature pairs were identified and a proof of concept resolution experiment was conducted, resulting in a diastereomerically pure product.
Article
Engineering, Chemical
Laureline Marc, Sabrina Guillemer, Jean-Marie Schneider, Gerard Coquerel
Summary: S-Ibuprofen has been found to be more efficient than racemic Ibuprofen, and there is a strong interest in implementing chiral resolution of racemic Ibuprofen in the continuous mode. Chiral resolution using diastereomeric salt formation has been successfully achieved in a Couette-Taylor crystallizer. Through a rationalized study, the factors of temperature gradient, rotation speed, residence time, and target temperature in the crystallizer were identified as having the strongest influence on productivity, yield, and diastereomeric excess. By utilizing continuous mode, the global productivity and diastereomeric productivity were significantly increased compared to batch mode.
CHEMICAL ENGINEERING RESEARCH & DESIGN
(2022)
Article
Engineering, Chemical
Hung Lin Lee, Ying Lun Hung, Ahmed Amin, Dhanang Edy Pratama, Tu Lee
Summary: As diastereomeric salt formation is the most popular method for the industrial preparation of single enantiomers, this study investigates the chiral resolution of ibuprofen (IBU) through this method. The study optimizes each step of the chiral resolution process and scales it up to a 0.5 L scale. Practical guidelines for future development of chiral resolution processes by diastereomeric salt formation are also suggested.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2023)
Article
Thermodynamics
Johnathon C. Ard, Juliano Schorne-Pinto, Mina Aziziha, Jacob A. Yingling, Amir M. Mofrad, Kaitlin E. Johnson, Clara M. Dixon, Theodore M. Besmann
Summary: In this study, the thermodynamic assessment and reassessment of 30 systems, including 5 newly assessed systems and 25 systems reassessed from published models, are detailed. Different modeling methods were used for liquid solutions and solid solutions, and the calculated results were compared with experimental data to ensure accuracy.
JOURNAL OF CHEMICAL THERMODYNAMICS
(2023)
Review
Chemistry, Physical
Gabriel Rubio-Perez, Natalia Munoz-Rujas, Fernando Aguilar, Rebecca Ravotti, Lukas Muller, Eduardo Montero
Summary: Interest in phase change materials is rising as a promising complement for renewable energies, with mixtures expanding the range of suitable PCM available. Precise knowledge of mixtures' phase behavior is required, and further studies are needed to enhance the currently available information in this open scientific field.
Article
Chemistry, Physical
Nasibeh Haghighi, James A. Lott
Summary: The research team aims to develop low-cost, reliable, compact lasers capable of transmitting high-speed infrared beams in free space for 5G and future 6G optical wireless communication and sensing systems. They have successfully designed, grown, fabricated, and tested 980 nm top-emitting triple VCSEL arrays with excellent performance, ideal for short-distance optical communication and sensing applications.
Article
Energy & Fuels
Alberto Giaconia, Irena Balog, Giampaolo Caputo
Summary: Hybridization of CSP plants with alternative energy sources can improve flexibility of operation and utilization factor of the plant. Experimental results show that heat transfer correlations based on the Dittus-Boelter equation can predict experimental results effectively.
Article
Materials Science, Multidisciplinary
D. Mary Deena, S. Arockia Anushya, A. Dhanusha, T. C. Sabari Girisun, A. Philominal
Summary: A single-beam Z-Scan experiment was conducted to investigate the nonlinear optical absorption and optical limiting properties of Bi2O3, rGO/Bi2O3, Bi2O3/WO3, and rGO/Bi2O3/WO3 nanostructures. The results showed that the synthesized nanostructures exhibited varying levels of nonlinear absorption, with bismuth-based nanostructures showing the lowest optical limiting threshold and a higher two-photon absorption coefficient. The presence of rGO contributed to the extended conjugation for charge transfer, while the strong UV-Visible absorption of Bi2O3 and WO3 led to a unique nonlinear optical response.
DIAMOND AND RELATED MATERIALS
(2024)
Review
Chemistry, Physical
Gyoergy Safran, Peter Petrik, Noemi Szasz, Daniel Olasz, Nguyen Quang Chinh, Miklos Serenyi
Summary: By scaling up the substrate size and utilizing the micro-combinatorial technique, the properties of multicomponent thin films as a function of their composition were comprehensively studied. Various characterization techniques were employed to analyze the films, enabling greater detail and efficiency in their characterization.
Article
Chemistry, Physical
Kaiyu Wang, Qing Yao, Jie Zhang, Lin Jing, Xiaohua Cheng, Chenyu Shang, Changqian Li, Feitong Chen, Tianliang Zhou, Huiling Zhu, Tingxi Li, Huiping Li, Zhongwei Wang, Jianxu Ding
Summary: This study investigates the performance of FA(1-x-y)MA(x)Cs(y)PbI(3-z)Br(z) perovskites in solar cells. The results show that bromine plays a critical role in lattice stability, while the content of methylammonium and cesium also affects the lattice.
CHEMISTRY OF MATERIALS
(2022)
Article
Chemistry, Organic
Srinivas Chandrasekaran, Takuji Hirose, Koichi Kodama
Summary: The optical resolution of chlorine-substituted tropic acids (TAs) by diastereomeric salt formation has been demonstrated. Efficient solvent-induced chirality switching was observed in the case of racemic 2-chlorotropic acid, while no chirality switching was achieved for racemic 3-chlorotropic acid and 4-chlorotropic acid. The position of the chlorine substituent plays an important role in the solvent-induced chirality switching effect.
Article
Chemistry, Physical
M. Schraml, H. Bataller, C. Bauer, M. M. Bou-Ali, F. Croccolo, E. Lapeira, A. Mialdun, P. Moeckel, A. T. Ndjaka, V Shevtsova, W. Koehler
Summary: Thermodiffusion in ternary mixtures, especially in highly polar and hydrogen bonding systems, shows characteristic sign changes and temperature-dependent migration of minority components. The Soret coefficients of the binaries have temperature-independent fixed points, and the decay with concentration can be related to negative excess volumes of mixing. Sign changes of the Soret coefficients in binaries can provide insights into the behavior of ternary mixtures.
EUROPEAN PHYSICAL JOURNAL E
(2021)
Article
Energy & Fuels
Lan Dong, Suying Ding, Zihua Wu, Huaqing Xie, Jiawei Wang, Tingting Wang, Yuanyuan Wang, Yueming Huang
Summary: In this study, oil-based ZnO/MWCNTs binary nanofluids and ZnO/MWCNTs/Au ternary hybrid nanofluids are proposed. The effects of nanoparticles concentration and the ratio of ZnO and MWCNTs on the optical properties and photothermal conversion performance are experimentally analyzed. The results show that ZnO/MWCNTs nanofluids exhibit slightly higher optical absorption performance than MWCNTs, and adding gold nanoparticles (Au NPs) to form ZnO/MWCNTs/Au nanofluids further enhances their absorption performance in the visible region. Moreover, the photothermal conversion efficiency of ZnO/MWCNTs nanofluids reaches the maximum value (91.2%), and the photothermal conversion efficiencies of MWCNTs and ZnO/MWCNTs/Au nanofluids are increased by 35.6% and 42.8%, respectively.
Article
Chemistry, Inorganic & Nuclear
Petra R. Varga, Alexandra Belovics, Gerhard Haegele, Gyoergy Keglevich
Summary: New phosphoryl alpha-hydroxyphosphonates, their acylated derivatives, and alpha-aminophosphonates were synthesized as potentially biologically active substrates. The reversible formation of alpha-hydroxyphosphonates led to the observation of interesting side-reactions.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
(2022)
Article
Biochemistry & Molecular Biology
Petra R. Varga, Alexandra Belovics, Peter Bagi, Szilard Toth, Gergely Szakacs, Szilvia Bosze, Rita Szabo, Laszlo Drahos, Gyorgy Keglevich
Summary: An efficient method utilizing acyl chlorides as reagents was developed for the acylation of hindered hydroxy groups in dialkyl alpha-hydroxybenzylphosphonates. The reaction did not require a catalyst and exhibited good optical purity. Furthermore, benzoylation of the alpha-hydroxy group was identified as a moiety that increased anticancer cytotoxicity and showed potential in multidrug resistant cancer cell lines.
Article
Biochemistry & Molecular Biology
Peter Abranyi-Balogh, Nikoletta Harsagi, Laszlo Drahos, Gyorgy Keglevich
Summary: The MW-assisted direct esterification of certain P-acids is a green method. Quantum chemical calculations revealed the activation enthalpies for the conversion of monoalkylphosphate to dialkylphosphate and dialkylphosphate to trialkylphosphate. The direct monoesterification can be performed with MW irradiation in the presence of a suitable ionic liquid additive, while the less favorable energetics of the second step requires another method for conversion to triesters.
Article
Chemistry, Multidisciplinary
Gyorgy Keglevich, Nikoletta Harsagi, Laszlo Drahos, Nora Zsuzsa Kiss
Summary: Monoalkyl phosphonic derivatives were synthesized by the microwave- and ionic liquid-promoted direct esterification of alkylphosphonic acids. These derivatives were then converted to dialkyl alkylphosphonates using alkyl halides in the presence of triethylamine under solvent-free microwave-assisted conditions. The study also identified a minor disproportionation side reaction and synthesized derivatives with different alkoxy groups.
Article
Chemistry, Physical
Bianka Huszar, Petra Regina Varga, Nora A. Szucs, Andras Simon, Laszlo Drahos, Gyorgy Keglevich
Summary: A literature survey and experimental evaluation revealed that practical syntheses for phosphonoyl- and phosphinoyl-bromoarenes, including some with two P-functions, could be developed under P-ligand-free microwave-assisted conditions.
Editorial Material
Chemistry, Organic
Gyoergy Keglevich
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Editorial Material
Biochemistry & Molecular Biology
Gyoergy Keglevich
Article
Chemistry, Organic
Petra Regina Varga, Konstantin Karaghiosoff, Eva Viktoria Sari, Andras Simon, Laszlo Hegedus, Laszlo Drahos, Gyorgy Keglevich
Summary: Diethyl alpha-benzylamino- and alpha-amino-benzylphosphonates obtained by the Kabachnik-Fields reaction were useful intermediates in the synthesis of other derivatives. Acylation of alpha-aminophosphonates with acyl chlorides led to the corresponding N-acyl species existing under a dynamic equilibrium of two conformers. NMR measurements at different temperatures revealed hindered rotation in some derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Istvan Timari, Peter Bagi, Gyorgy Keglevich, Katalin E. Kover
Summary: The original homonuclear decoupled experiments are suitable for compounds with low natural isotopic abundance of NMR-active heteronuclei, while molecules with highly abundant heteronuclei result in more complex spectra with overlapping signals, which may hinder the accurate assignment of resonances. New heteronuclear decoupled experiments, such as HD PSYCHE 1H and TOCSY, provide simplified spectra with significantly increased resolution and allow reliable assessment of individual resonances. These methods have been successfully applied to the structure elucidation of a challenging stereoisomeric mixture, and they have potential applications in medicinal chemistry and metabolomics for other important compounds containing 31P or 19F.
Article
Biochemistry & Molecular Biology
Bence Varga, Levente Buna, Daniella Vincze, Tamas Holczbauer, Bela Matravolgyi, Elemer Fogassy, Gyorgy Keglevich, Peter Bagi
Summary: A library of 1-adamantyl arylthiophosphonates was synthesized, and a chiral separation method using (S)-1-phenylethylamine as the resolving agent was developed. Three out of five arylthiophosphonates were obtained in enantiopure form (ee > 99%). The subsequent desulfurization reaction retained the enantiomeric purity of the optically active arylthiophosphonates (ee = 95-98%), providing an alternative method for the preparation of 1-adamantyl aryl-H-phopshinates. The absolute configuration of (S)-1-adamantyl phenylphosphonothioic acid was determined using single-crystal XRD, and the organocatalytic applicability of (S)-1-adamantyl phenylphosphonothioic acid as a P-stereogenic Bronsted acid was evaluated.
Article
Chemistry, Multidisciplinary
Bianka Huszar, Renata Szolga, Szilvia Bosze, Rita Olahne Szabo, Andras Simon, Konstantin Karaghiosoff, Matyas Czugler, Laszlo Drahos, Gyoergy Keglevich
Summary: P-functionalized derivatives of 9-phenyl-9H-carbazole and dihydroindoline were synthesized using microwave irradiation. The products showed significant cytotoxic activity, outperforming the traditional method.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Bianka Huszar, Zoltan Mucsi, Gyorgy Keglevich
Summary: This study investigated a less-studied variation of the Hirao reaction, which involves the coupling of arylboronic acids with >P(O)H reagents. The reaction was catalyzed by Pd(OAc)2 and the ligand was supplied via its trivalent tautomeric form. The optimal conditions for the synthesis of various phosphine oxide and phosphonate derivatives were explored. The self-assembling ligands around the Pd(2+) center played a crucial role in the mechanism and efficiency of the catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Editorial Material
Multidisciplinary Sciences
Gyorgy Keglevich
Article
Chemistry, Multidisciplinary
Gyorgy Keglevich, Nikoletta Harsagi, Sarolta Szilagyi
Summary: A chlorine-free and simple method was developed for the preparation of alkylamino-3-phospholene oxides, and their diastereoselective synthesis was achieved. The interconversion between cyclic phosphinic amides and phosphinates holds significant value.