The molecular design of coordination polymers (CPs) and metal-organic frameworks (MOFs) has attracted increasing attention in the areas of inorganic chemistry and functional materials. In this study, a new series of 2D CPs and 3D MOFs was hydrothermally assembled from metal(II) chlorides and 2,2'-((4-carboxy-1,2-phenylene)bis(oxy))diacetic acid (H3cpbda) as a flexible and little-explored tricarboxylate linker. Additionally, several types of aromatic N,N-donor auxiliary ligands were used to promote crystallization, namely, 1,10-phenanthroline (phen), 4,4'-bipyridine (bipy), bis(4-pyridyl)amine (bpa), 1,2-di(4-pyridly)ethylene (dpey), or 1,2-di(4-pyridly)ethane (dpea). The obtained products were fully characterized and identified as [M3(μ6-cpbda)2(phen)2]n·4nH2O (M = Zn (1), Cd (2)), [Co3(μ5-cpbda)2(μ-bipy)2]n·2nH2O (3), [Zn3(μ5-cpbda)2(μ-bipy)2]n (4), [Zn(μ3-cpbda)(Hbpa)]n·4nH2O (5), [Zn4(μ3-cpbda)2(μ-OH)2(μ-dpey)3(H2O)2]n·2nH2O (6), [Co3(μ4-cpbda)2(μ-dpey)3]n·2nH2O (7), and [Ni3(μ4-cpbda)2(μ-dpea)3]n·2nH2O (8). Their structural and topological features were also explored, allowing us to identify a diversity of 2D and 3D coordination networks. Remarkably, Zn-based coordination polymers 5 and 6 revealed a high catalytic activity and reusability in the condensation reaction between benzaldehyde and malononitrile (or ethyl cyanoacetate), leading to almost quantitative product yields (99%) under optimized conditions. The present work contributes to widening the family of CPs/MOFs assembled from flexible polycarboxylate linkers and highlights a promising application of these compounds in heterogeneous catalysis.

The cycloaddition reaction is one of the most common reactions in organic chemistry. It has been applied in various fields. Herein, we focus on the application of cycloaddition reactions in investigating biological molecules and materials using magnetic resonance techniques. To facilitate magnetic resonance studies such as electron paramagnetic resonance (EPR) spectroscopy and paramagnetic nuclear magnetic resonance (NMR) spectroscopy, there is often a requirement to attach spin labels and paramagnetic tags to the system of interest. The cycloaddition reaction is one of the ways to tether these spin labels and paramagnetic tags. In this review, we highlight the applications of various cycloaddition reactions such as the Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction, the strain-promoted azide–alkyne cycloaddition (SPAAC) reaction and the Diels–Alder reaction in the interdisciplinary field of magnetic resonance studies of biomolecules, including proteins, nucleic acids, carbohydrates, lipids and glycans, as well as materials.

In the age of rising antibiotic resistance among various pathogens, the search for alternative antimicrobial strategies has become a pressing scientific challenge. Metal ions are indispensable to life, participating in a vast range of structural and catalytic roles across all forms of biology. The Biological Inorganic Chemistry Group explores the fundamental chemistry of metal ions in biological systems, focusing on their role in host-pathogen interactions. In this article we aim to focus on four aspects, representing the main scientific interests of our group. Metal homeostasis and assimilation chapter explores the coordination chemistry of biologically essential Mn(II) and Fe(II) ions using model peptides and fragments of metal transport proteins. By varying the number and position of His, Asp, and Glu residues, the study revealed how sequence composition governs metal-binding strength and selectivity. Studies on bacterial Fe(II) transporters, such as FeoB, identified potential metal-binding regions and mechanisms of ion transfer, deepening our understanding of metal recognition and transport in biological systems. To better understand iron uptake in pathogens, we explored synthetic siderophore analogs as tools for studying this process. Ferrichrome mimics effectively chelated Fe(III) and were taken up by Pseudomonas putida and Escherichia coli. Fluorescent labeling allowed visualization of these complexes in cells. Ferrioxamine E analogs showed promise as 68Ga-labeled imaging agents. The ability of various siderophores to bind metal ions such as Cu(II), Zn(II), Ni(II), Bi(III), and Zr(IV) has also been studied. One of the chapters focuses on chaperonins and metalloproteinases as bacterial virulence factors. GroEL1, a chaperonin present e.g.in Mycobacterium, binds metal ions like Cu(II) via its unstructured His-rich C-terminal tail, helping bacteria survive under toxic metal conditions. Peptide studies showed that specific His residues position affects metal complex stability, and various metals create distinctly different complex geometries. Bacterial metalloproteinases need Zn(II) for activity. Research on peptide models revealed how Cu(II) and Ni(II) can inhibit these enzymes by displacing Zn(II). Studies on human MMP-14 enabled the identification and detailed characterization of the metal-binding site, as well as the elucidation of the interactions between peptide-based inhibitors, the catalytic metal ion, and the enzyme active site. Detailed knowledge of virulence proteins may enable their use as a potential target for novel drugs. Membrane proteins are vital for transport, signaling, and maintaining membrane integrity. However, their studies are challenging due to poor solubility and detergent sensitivity. Lipoprotein nanodiscs (NDs) has revolutionized research on these proteins, by providing a soluble, stable, and physiologically relevant environment for membrane protein reconstitution. Their defined size, high stability, and compatibility 34 W. WOŹNIAK-LASZCZYŃSKA, K. GŁADYSZ, P. POTOK, M. ZAWADA, B. ORZEŁ, K.SZCZERBA… with structural and functional studies make NDs a powerful tool for investigating membrane transporters, ion channels, and receptors. This article highlights the key aspects of metal interactions with siderophores, transport and chaperone protein fragments, and metalloproteinases, and demonstrates how nanodiscs can advance the study of membrane proteins.

The article consists of two parts, introducing the field of mechanical bond chemistry, followed by the research activities of the Supramolecular Organic Chemistry Group at the University of Wrocław. The first, literature-based section introduces the concept of the mechanical bond, outlining its structural and chemical consequences. The main classes of mechanically interlocked molecules, i.e., rotaxanes, catenanes, and molecular knots, are briefly characterized, with particular attention given to how mechanical bonding influences their stereochemistry, reactivity, and dynamic behavior. The second part presents an overview of the Supramolecular Organic Chemistry Group, established in 2021 at the Faculty of Chemistry, University of Wrocław. It summarizes the group’s history, growth, and major research interests, which focus on the design, synthesis, and investigation of novel mechanically interlocked molecules. Special emphasis is placed on ongoing projects concerning functional rotaxanes, catenanes, and dynamic systems that form the basis for exploring new types of molecular machines. The article aims to highlight both the broader significance of mechanical bond chemistry and its specific role in the current research directions developed within the Wrocław group.

This study examined preservice science teachers’ perceptions of learning difficulties in Organic Chemistry and their relationship with achievement in General Chemistry. A quantitative descriptive–correlational design was employed. The participants were 103 undergraduate students enrolled in the Science Education program who were taking an Organic Chemistry course, selected through total sampling. Data were collected using a four-point Likert-scale questionnaire measuring perceived learning difficulties and analyzed using SPSS 23. The results indicated that students’ perceptions of learning difficulties were distributed across high and low levels. Among the assessed indicators, problem-solving and analytical skills were perceived as the most challenging. No significant differences were found in perceptions based on gender. Meanwhile, a significant positive correlation was identified between General Chemistry achievement and perceived learning difficulties in Organic Chemistry (R² = 0.91), indicating a strong association within the study sample. However, this association should be interpreted cautiously due to the correlational design of the study. These findings suggest that students’ understanding of foundational chemistry concepts plays a crucial role in shaping their learning experiences in Organic Chemistry and should be strengthened to support more effective instruction.

The development of new synthetic strategies that exploit visible light as a sustainable energy source represents a significant advancement in organic synthesis. Benzylthioethers and benzylsulfones are pivotal structural motifs, widely utilized as synthetic intermediates and functional groups in both organic and medicinal chemistry. In this study, we report a novel photoredox-catalyzed intermolecular approach for the formation of benzylic C-S bonds via direct functionalization of benzylic C(sp3)-H bonds. This methodology facilitates the efficient synthesis of secondary thioether and sulfonylation derivatives through the reaction of secondary benzylic substrates with readily available sodium benzenethiolate and sodium sulfinates under visible-light irradiation. This protocol offers a practical and atom-economical route to accessing diverse sulfur-containing compounds under mild conditions.

Enamines serve as pivotal compounds in synthetic organic chemistry. Herein, a homologative enamination of aromatic aldehydes was achieved through three steps: [3 + 2] cycloaddition with nonstabilized azomethine ylide, quaternization with various alkyl halides, and eliminative ring-cleavage of oxazolidine core with sodium hydride in dimethyl sulfoxide. The obtained dialkylstyrylamines were employed as useful intermediates, furnishing a number of phenethylamines via reduction with sodium borohydride in good yields or were acylated with trifluoroacetic anhydride. We also demonstrated that the titled enamination could be performed in two step manner applying thermal ring-cleavage of 5-aryloxazolidine with trifluoroacetic anhydride, providing N-acylaminostyrenes in moderate yields. The proposed methodology for the homologative enamination features with gram-scale approach, readily available inexpensive materials, and simple laboratory techniques.

Aromaticity is a central concept in organic chemistry, traditionally evaluated through structural, magnetic, and electronic criteria. In this study, density functional theory (DFT) calculations were performed to systematically investigate the impact of various substituents (-H, -Me, -CH₂-CH₂-, -F, -Cl, -SiH₃, -GeH3, -NH2, -OH, -BH2, -CN) on the aromaticity of CH isomers of diazoles across four positional isomers (A-D). Aromaticity was quantified using the HOMED, BI, NICS(1), and NICSzz(1) indices, while Natural Bond Orbital (NBO) analysis provided insights into charge distribution and second-order stabilization energies (E(2)). The results demonstrate that silyl and germyl substituents significantly enhance Schleyer-type hyperconjugative aromaticity, reflected by higher HOMED/BI values, more negative NICS indices, and stronger σ→π/π* delocalization energies in the NBO framework. In contrast, halogen substituents, particularly fluorine, diminish aromaticity, in some cases leading to near-zero or even positive NICSzz values. The π-donating substituents -NH₂ and -OH exert only modest effects on aromaticity, whereas the π-accepting -CN group generally suppresses aromatic stabilization. In contrast, the -BH₂ substituent behaves as an efficient σ-donor, significantly enhancing aromaticity, comparable to those observed for -SiH3 and -GeH3 derivatives. Strong correlations were observed between NICS and NICSzz, as well as between NICS and E(2), confirming the direct relationship between ring currents and hyperconjugative stabilization. This comprehensive multicriteria approach highlights the crucial role of substituents and positional isomers in governing hyperconjugative aromaticity in CH tautomer of diazole scaffolds and provides new insights into the electronic origin of this phenomenon.

Plant protoberberine alkaloids: structural diversity, biosynthesis, synthesis, biological activity, structure-activity relationships and clinical applications of berberine.

Unravelling the speciation of gold(I) fluorinated benzenethiolates using hyphenated HPLC/ICP-AES and HPLC/ESI-MS techniques.

Critical review of organic radical chemistry in peracetic acid-based advanced oxidation processes for water decontamination

Fundamental inorganic chemistry and cancer and inflammatory mechanism of NO. kinetic approach to revealing insights into Cancer and other diseases

Transesterification reactions are fundamental transformations in organic chemistry, yet performing them in aqueous media is challenging because of the competing hydrolysis reaction. In this study, we describe a mutant of alcohol oxidase from Phanerochaete chrysosporium (PcAOx-VPN) that also exhibits transesterification activity. Moreover, PcAOx-VPN displays no detectable hydrolytic activity, owing to its hydrophobic active site, which effectively excludes water. These characteristics make PcAOx-VPN a promising catalyst for transesterification reactions in aqueous media, a context that is typically compromised by competing hydrolysis.

Abstract Macrocyclic compounds, exhibiting unique properties arising from their large-ring frameworks, have captivated the attention of organic chemists over the last few decades. These molecules serve specific functions across disciplines, including synthetic chemistry, materials science, and biology. Representative molecules in this category, including crown ethers, calix[n]arenes, and porphyrinoids composed of ether/phenol/pyrrole subunits, exhibit unparalleled structural and functional diversity. In contrast, macrocycles exploiting quinoline/quinazoline as key building blocks to construct specific macrocyclic architectures have received limited attention and are much less explored. In this Highlight Review, we summarize our recent advances in oligo-quinoline/quinazoline macrocycles. Emphasis is focused on synthetic strategies, structural features, and emerging applications in organometallic, supramolecular, and photophysical chemistry. We anticipate that these collective results will guide new molecular designs within the broader family of heterocycle-based macrocycles.

Precise three-dimensional arrangements of atoms and functional groups govern molecular reactivity and biological function, making stereocontrol a central goal in modern organic and medicinal chemistry. Yet reconciling broad substrate generality with high enantioselectivity remains a core limitation of enantioselective catalysis, motivating the pursuit of privileged chiral catalysts. Here we design a new-to-nature photoenzyme that unlocks enzymatic deracemization of structurally diverse allenes, an entropically disfavored process inaccessible to natural biocatalysts. Structure-guided design created substrate-specific interaction networks, delivering high enantioenrichment for axially chiral allenic carboxylic acids, esters, and amides via triplet energy transfer under aerobic conditions. X-ray crystal structures of enzyme-substrate complexes reveal tailored chiral pockets that accommodate distinct substrates and direct enantiocontrol, rationalizing the breadth and selectivity observed. This work reconciles generality with high selectivity on an enzymatic platform, establishes deracemization as an evolvable route to axially chiral molecules, and broadens activation strategies for stereochemical editing.

The uneven detection of prebiotic organic compounds in meteorites-where amino acids and nucleobases are commonly identified but sugars remain rare and poorly characterized-limits our understanding of extraterrestrial organic chemistry. This discrepancy is striking given that laboratory simulations of interstellar ice chemistry readily produce complex sugars. Here we report the simultaneous analysis of sugar and amino acid enantiomers in a meteorite sample. Multiple aldoses were detected in the Orgueil meteorite, including ribose, arabinose, xylose, lyxose, and the ketopentose ribulose, several of which display near-racemic distributions consistent with an extraterrestrial origin. Recovery experiments demonstrate that sugar abundances are severely underestimated. Despite this limitation, pentose abundances are comparable to those of some C4-C5 amino acid enantiomers, implying higher true concentrations. These results indicate efficient abiotic sugar formation in space and suggest that meteorites may have delivered a broader range of prebiotically relevant sugars to early Earth than previously recognized.

The synthesis of carboxylic esters represents a pivotal transformation in organic chemistry owing to their widespread utility in pharmaceuticals, natural products, materials science, and fine chemicals. Traditionally, esterification by redox dehydration required a PIII/PV process using PIII as the oxygen acceptor. Here we report a novel method of redox dehydration employing thiourea as an [O] acceptor through desulfurization. Using this rapid and operationally simple protocol, a variety of esters and lactones can be easily synthesized from readily available substrates in good to excellent yields.

Abstract:: Over the past few decades, the Barton-Kellogg olefination reaction has emerged as a crucial C–C connective technique utilized in synthesizing overcrowded alkenes. The reaction has good stereoselectivity and has an enduring relevance due to the scope of its integration into complex molecule synthesis and material science applications. This review examines the developments in Barton- Kellogg olefination between 2021 and 2025, highlighting significant advances in mechanistic understanding, reaction conditions, substrate scope, and methodology. Recent developments, including the creation of asymmetric versions, gentler reaction protocols, and innovative catalyst systems, have enhanced the synthetic value of this reaction. Additionally, this review summarizes recent research on computational studies related to the mechanism and kinetics of the response, in relation to the present challenges and possible future paths for synthetic organic chemistry researchers.

Abstract:: 2-Aminobenzothiazole represents a versatile class of heterocyclic compounds that is composed of a fused benzene ring and a thiazole ring. In recent years, benzothiazole derivatives have garnered considerable attention for research and development due to their broad spectrum of pharmacological properties. Owing to their strong pharmacological activity and wide range of applications, synthetically accessible and adaptable 2- aminobenzothiazole scaffolds are very intriguing in the fields of biology and synthetic organic chemistry. Benzothiazole moiety-containing analogs possess significant antimicrobial, antiviral, anti-inflammatory, antidiabetic, anticancer, antimalarial, antitubercular, anticonvulsant, antiasthmatic, diuretic, analgesic, and anthelmintic activities. Research on the pharmaceutical properties of benzothiazole derivatives remains a fascinating area with potential for discovering novel drugs or treatments. The promising medicinal properties of benzothiazoles and their derivatives have prompted medicinal chemists to develop numerous new therapeutic agents, thereby driving the development of efficient and innovative synthetic approaches. This review focuses on the numerous methods of synthesis and reactions of 2-aminobenzothiazoles and their derivatives that have been utilized over the period 2010-2025, to encourage further research and innovation in the development of novel compounds with a range of applications in drug discovery and other fields.

Organic synthetic chemistry has undergone a paradigm shift driven by breakthroughs in artificial intelligence (AI). Data-driven methods help accelerate hypothesis evaluation and reduce experimental trial-and-error efforts. However, its practical utility is constrained by the out-of-distribution (OOD) issue, where predictions usually fail when extrapolating to unseen reactions with new catalysts, substrates, or conditions. Here, we introduce SynAD (synthetic applicability domain), a machine learning framework for assessing the predictive capability of AI models trained with existing data. SynAD combines descriptors with model-adaptive distance metrics to automatically demarcate reliable and unreliable reactions. Validated on the Ullmann Ligand Dataset (ULD, >5000 reactions), SynAD a priori distinguishes predictable chemical space, resulting in a prediction accuracy of R2=0.90 (at 12.3% coverage) from a baseline of R2 = -0.21. This capacity to target reliable chemical space is consistently observed across 6 additional datasets. We also enable a SynAD score to quantify reaction class predictability, guiding experimental focus on OOD spaces. By defining model limits, SynAD provides a critical guardrail for chemists to trust AI, allocate resources strategically, and accelerate de novo discovery.