Article
Chemistry, Applied
Khadija Waqar, Kasper Engholm-Keller, Marcel S. Joehnke, Dereck E. W. Chatterton, Mahesha M. Poojary, Marianne N. Lund
Summary: Protein-polyphenol adducts are formed through covalent bonding between oxidized polyphenols and proteins. The study identified significant thiol and amine loss in beta-LQ compared to beta-LG, along with site-specific 4MBQ-induced modifications on various amino acids. However, no significant differences in digestibility were observed between beta-LG and beta-LQ in in vitro studies.
Article
Chemistry, Organic
Qingyuan Feng, Yamin Wang, Binnan Zheng, Shenlin Huang
Summary: A sustainable method for converting terminal alkynes into carboxylic acids is developed using synthetic electrolysis in an undivided cell at room temperature. This protocol, which eliminates the need for transition metal catalysis and stoichiometric chemical oxidants, is compatible with various aryl, heteroaryl, and alkyl alkynes. Mechanistic studies suggest that sodium nitrite plays a triple role as an electrolyte, nitryl radical precursor, and nitrosating reagent.
Article
Electrochemistry
Yangli Wang, Xiao-Jing Zhao, Xi Wu, Lizhu Zhang, Ganpeng Li, Yonghui He
Summary: An electrochemical oxidation reaction was developed for the synthesis of trisubstituted oxazoles and imines without the use of external oxidants and transition-metal catalysts. The reaction yielded various compounds in moderate to excellent yields, and mechanistic studies suggested a radical process.
Review
Chemistry, Medicinal
Gonzalo de Gonzalo, Andres R. Alcantara
Summary: The beta-dicarbonyl structure is a key component in many biologically and pharmaceutically active compounds, with potential therapeutic effects on various pathological disorders, making it a popular topic of interest among organic chemists. Various methods have been developed for the preparation of 1,3-diketones, as well as for the synthesis of branched beta-dicarbonyl compounds through alpha-functionalization of non-substituted 1,3-diketones.
Article
Biochemistry & Molecular Biology
Emad F. Newair, Abdulaziz Al-Anazi, Francois Garcia
Summary: This study investigates the antioxidant role of glutathione (GSH) in the oxidation process of wine polyphenols. Electrochemical methods and UPLC-MS techniques were used to determine the oxidation products and reaction pathways of polyphenols. The results show that in the presence of GSH, polyphenols undergo electrochemical oxidation and form GSH conjugates. These findings contribute to understanding and predicting the oxidative degradation pathway of polyphenols in wine, providing guidance for winemakers to control and optimize the sensory characteristics of their wines.
Article
Chemistry, Applied
Dehua Wu, Xinyi Fang, Jintong Song, Lang Qu, Xiangge Zhou, Haifeng Xiang, Jun Wang, Jin Liu
Summary: The designed simple, smart, and chiral binaphthalene-substituted 4-ene-beta-diketones exhibit high emissive properties and unique chemical reactions, making them suitable for sensing, recognition, and staining cytoplasm in living cells. They provide a new platform for the design of multi-stimuli-responsive, smart, and chiral materials.
Article
Chemistry, Organic
Katarina L. Keel, Jetze J. Tepe
Summary: The study presents the first total synthesis of Nortopsentin D, involving a pivotal condensation and subsequent cyclization of amidine and dione via a pinacol-like rearrangement. This unique synthetic strategy is significant for the formation of 5,5-disubstituted (4H)-imidazol-4-one containing natural products.
Article
Chemistry, Organic
Yi Yu, Yi-Min Jiang, Xiao-Bin Zhu, Yong-Ying Lin, Yaofeng Yuan, Ke-Yin Ye
Summary: A new electrochemical method for the synthesis of beta-sulfoxides has been uncovered, which is simple, easy to operate, and shows great potential for various applications.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Inorganic & Nuclear
Pieter J. Swarts, Elizabeth Erasmus, Eleanor Fourie
Summary: Three classes of ferrocenyl-containing beta-keto compounds were synthesized, showing different tautomeric forms in various solvents which can be distinguished by FTIR and H-1 NMR measurements. Computational studies confirmed the predominance of the keto conformation in beta-ketoester and beta-ketoamide compounds.
Article
Chemistry, Organic
Samira Poorsadeghi, Katsuki Endo, Satoru Arimitsu
Summary: A new enantioselective fluorination method using beta, beta-diaryl serines as a primary amine organocatalyst has been reported, yielding fluorinated products with high yields and excellent enantioselectivity. The presence of the CO2H group in the beta, beta-diaryl serines is found to be crucial for inducing the high enantioselectivity in the reaction.
Article
Chemistry, Physical
Jingjing Qiu, Daniel Boskin, Dallas Oleson, Weiming Wu, Marc Anderson
Summary: Plasmon-mediated electrocatalysis, based on plasmonic gold nanoparticles (Au NPs), provides a promising approach to enhance electrochemical reactions by introducing light for plasmonic excitation. Among the metals investigated in alkaline electrolytes, gold (Au) exhibits the lowest onset potential for catalyzing the electrooxidation of 4-(hydroxymethyl)benzoic acid (4-HMBA), while platinum (Pt) fails to catalyze the electrooxidation of 4-HMBA under alkaline conditions. High-performance liquid chromatography analysis confirms the presence of 4-carboxybenzaldehyde and terephthalic acid as products of the electrochemical oxidation of 4-HMBA on the Au working electrode.
JOURNAL OF CHEMICAL PHYSICS
(2022)
Article
Materials Science, Ceramics
Xuekun Tian, Deze Ouyang, Kai Su, Fei Zhao, Jinxing Gao, Xinhong Liu
Summary: This study investigates the effect of Y2O3 on the oxidation behavior of beta-SiAlON powders. The results show that Y2O3 contributes to the generation of beta-SiAlON and increases the oxidation rate and decreases the activation energy during the initial oxidation period. However, in the final oxidation period, the incorporation of Y2O3 leads to the formation of a denser glass film which reduces the oxidation rate.
CERAMICS INTERNATIONAL
(2022)
Article
Chemistry, Multidisciplinary
Tian Feng, Zile Zhu, Dongmei Zhang, Siyi Wang, Ruopu Li, Zhaolin Zhu, Xinxing Zhang, Youai Qiu
Summary: A straightforward and efficient method for constructing dual alpha,beta-C(sp(3))-H functionalized cyclic N-aryl amines using electrocatalysis and iron catalysis is disclosed. The method achieves high chemo- and site-selectivity through multiple single electron oxidations, setting the stage for challenging multiple site selective C-H functionalization. The mechanism is supported by various experimental probes and theoretical investigations.
Article
Chemistry, Analytical
Emad F. Newair, Ibrahim M. A. Mohamed, Francois Garcia, Abdulaziz Al-Anazi
Summary: New antioxidant materials in biomedical applications are being studied using chromatographic techniques, mass spectroscopy, and electrochemical analyses to understand their reaction mechanism and products with nucleophiles. The oxidation products of CFT and its reaction pathways in the presence and absence of GSH were identified using UPLC-MS analysis.
MICROCHEMICAL JOURNAL
(2023)
Article
Electrochemistry
Maryam Mehrdadian, Sadegh Khazalpour, Ameneh Amani, Mahdi Jamshidi
Summary: The study found that the oxidation product of 4-ethynylaniline is unstable in acidic and alkaline solutions and can be hydrolyzed under strong acidic and alkaline conditions. A new compound was synthesized by electrochemical oxidation, showing inhibitory effects on receptors. The diffusion coefficient of 4-ethynylaniline in acetonitrile was also determined in the experiment.
ELECTROCHIMICA ACTA
(2021)
Article
Chemistry, Analytical
Mahmood Masoudi Khoram, Niloofar Mohamadighader, Davood Nematollahi, Sadegh Khazalpour, Hossein Masoumi, Hojjat Alizadeh
Summary: A green electrochemical method was developed for the synthesis of new spiro and dispiro pyrimidine derivatives. The reactivity of the nucleophile (barbituric acids) was found to be crucial in determining the type of product. The synthesized compounds showed good antibacterial performance against gram-positive bacteria.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Zahra Souri, Mahmood Masoudi Khoram, Davood Nematollahi, Mohammad Mazloum-Ardakani, Hojjat Alizadeh
Summary: Electrochemical oxidation of imipramine in aqueous solutions was studied, showing a complex behavior at different pH values. The oxidation of imipramine at a pH of about 5 led to the formation of a unique dimer, which was fully characterized. A possible reaction mechanism for the oxidation process was proposed. The synthesized dimer exhibited fluorescence activity and good antibacterial performance.
SCIENTIFIC REPORTS
(2022)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Davood Nematollahi
Summary: A new derivative of desloratadine (DQ-TBC complex) was synthesized for the first time using a green electrochemical method. The electrooxidation of 4-tert-butylcatechol (TBC) in the presence of desloratadine (DES) was investigated to optimize the synthesis conditions of DQ-TBC complex. The results suggest that the electrooxidation of TBC in the presence of DES leads to DQ through an ECE mechanism. The synthesized compound showed promising antibacterial activity against Bacillus cereus and Staphylococcus aureus.
ELECTROCHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Shannon L. Goes, Jordan E. Nutting, Nicholas J. Hill, Shannon S. Stahl, Mohammad Rafiee
Summary: This article describes the development of an undergraduate laboratory experience that introduces synthetic and analytical electrochemistry concepts to advanced organic chemistry students. The experiments provide an authentic experience in organic electrochemistry and strengthen fundamental organic chemistry skills.
JOURNAL OF CHEMICAL EDUCATION
(2022)
Article
Electrochemistry
Heydar Hameed Salman Arkwazee, Niloofar Mohamadighader, Davood Nematollahi, Arash Rabiee, Hojjat Alizadeh
Summary: This article describes a method for synthesizing new sulfonamide derivatives using electrochemical methods without toxic reagents, and finds that these products have good antibacterial performance against bacteria.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2022)
Article
Electrochemistry
Niloofar Mohamadighader, Davood Nematollahi, Mahnaz Saraei
Summary: Electrochemical oxidation of phenothiazine in an acetonitrile/water mixture was investigated, revealing that the oxidation pathway varies with respect to pH. The results led to the synthesis of two new types of PTZ dimer and provided insights into the oxidation mechanism of PTZ.
ELECTROCHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Buwanila T. Punchihewa, Vidit Minda, William G. Gutheil, Mohammad Rafiee
Summary: Electrochemistry plays a crucial role in chemical reactions and has wide applications in electroanalysis and electrosynthesis. By designing an electrochemical cell with a thin layer electrode, the limitations of traditional electrolysis cells can be bypassed, allowing for minute-scale electrolysis reactions and real-time probing of redox-active components.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Electrochemistry
Mohammad Reza Talebi, Davood Nematollahi, Ahmad Reza Massah
Summary: The electrochemical oxidation of N-(4-aminophenyl) and N-(4-hydroxyphenyl)benzenesulfonamide derivatives was investigated at different pH values and concentrations. The oxidation potential and mechanism of these compounds were found to be pH dependent. The oxidation products were found to undergo hydroxylation and/or dimerization reactions. The adsorption behavior and oxidation products under conditions similar to the human body were also studied.
ELECTROCHIMICA ACTA
(2023)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Fereshteh Javanmardi, Davood Nematollahi
Summary: The electrochemical behavior of rifampicin, an anti-tuberculosis drug, was studied in a water/ethanol mixture. The drug was found to undergo two-step oxidation, with the first step being a reversible oxidation of the hydroquinone moiety and the second step being an irreversible oxidation of the phenolic ring. The adsorption activity and diffusion coefficient of rifampicin were also determined, indicating that the first oxidation step is diffusion-controlled and the second step is a diffusion/adsorption control process. The oxidation of rifampicin was found to be complex and highly pH-dependent, with different rates of reaction observed for different drugs used in combination therapy.
ELECTROCHIMICA ACTA
(2023)
Article
Chemistry, Multidisciplinary
Lida Khalafi, Nastaran Nikzad, Asayiel Alhajeri, Brandon Bacon, Karla Alvarado, Mohammad Rafiee
Summary: In this article, a demonstration and activity are presented to help students understand electrochemical phenomena by visualizing and analyzing the expansion of a micrometer-sized diffusion layer. The activity utilizes a kids' optical microscope with a digital eyepiece camera to observe and record the formation and expansion of the diffusion layer. By analyzing the time-dependent changes in the colorful diffusion layer, students can derive the diffusion coefficient of electrochemically generated hydroxide ion.
JOURNAL OF CHEMICAL EDUCATION
(2023)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Davood Nematollahi
Summary: This study investigates the toxic metabolites formed from the oxidation of rifampicin and acetaminophen in the body. It provides strong evidence of a catalytic reaction between vitamin C and the oxidized form of rifampicin. Additionally, contrary to previous reports, this study discovers another catalytic reaction between oxidized acetaminophen and rifampicin.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2023)
Article
Electrochemistry
Zahra Godini, Davood Nematollahi, Faezeh Zivari-Moshfegh
Summary: In this study, the electrochemical complexation of five azole antifungal drugs with silver, copper and zinc cations was conducted in an undivided electrolytic cell. Twenty complexes were synthesized using a simple method in water/ethanol mixtures with high yield and purity. The applied current and acid concentration were found to have no significant effects on the yield and purity of the complexes, but they did affect the cell voltage and energy consumption.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Pouria Patoghi, Ali Sadatnabi, Davood Nematollahi
Summary: In this study, a new convergent paired electro-organic synthesis method for sulfonamide derivatives was introduced, which follows the principles of green chemistry and does not require catalysts, oxidants, halogens, or amines. Instead of using toxic amine compounds, an innovative mechanism based on the reduction of nitro compounds and in-situ production of amine compounds was used. The mechanism involves cathodic reduction of nitro compounds to hydroxylamine compounds and anodic oxidation of hydroxylamine compounds to nitroso compounds.
SCIENTIFIC REPORTS
(2023)
Review
Chemistry, Multidisciplinary
Mohammad Rafiee, Dylan J. Abrams, Luana Cardinale, Zachary Goss, Antonio Romero-Arenas, Shannon S. Stahl
Summary: Electrochemical methods provide control over chemical synthesis by tuning the potential or current, and measuring the current or potential can offer mechanistic insights. This tutorial review explains the use of cyclic voltammetry and chronoamperometry to study reaction mechanisms, optimize electrochemical reactions, or design new reactions. These techniques allow analysis of concentrations of redox active species in solution and offer a versatile strategy for kinetic analysis.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Analytical
Mikayla N. Mayer, Mohammad Rafiee
Summary: In this study, insights from mechanistic studies on aminoxyl catalyzed oxidation of alcohols and aldehydes were utilized for the fabrication of a gas phase sensor for ethanol and acetaldehyde. This electrochemical sensor, composed of an aminoxyl radical and graphene oxide, can have its response and selectivity altered by tuning the basicity of the graphene oxide.