Search Results (192)

Nitrile-containing compounds are integral to pharmaceuticals, agrochemicals and polymer industries, yet their environmental persistence and toxicity pose major challenges. Biocatalytic approaches using nitrile-converting enzymes—particularly nitrilases and nitrile hydratases—offer sustainable alternatives to conventional hydrolysis, enabling the selective transformation of nitriles into amides and acids under mild conditions. This review presents an industrial perspective on nitrile-converting enzymes, summarising their catalytic potential, current limitations, and emerging strategies for stability, activity and performance enhancement. Advances in protein engineering, metagenomic discovery and biocatalytic optimisation have already expanded their wider applicability, while synthetic biology and protein design tools are accelerating the development of tailored biocatalysts. The integration of these enzymes into cascades and chemoenzymatic processes supports scalable and innovative solutions to green manufacturing. Collectively, these emerging strategies position nitrile-converting enzymes as versatile tools for sustainable catalysis, with growing relevance in fine chemical synthesis, waste remediation, and bio-based synthetic platforms. Full article

Donor–acceptor (D–A) cyclopropanes are important precursors in the synthesis of complex molecules due to their bidentate character and high reactivity. Among them, cyclopropane-1,1-dicarbonitriles are less commonly reported in modern literature, primarily because of the high reactivity of the nitrile groups and their limited compatibility with metal-catalyzed processes, which is caused by the geometrical constraints imposed by the linear cyano substituents. While the cyano groups can be seen as a limitation, they also offer synthetic versatility by serving as handles for further functionalization. In this work, we performed a cycloaddition reaction with mercaptoacetaldehyde, leading to a new class of DA cyclopropanes bearing a thiazole moiety. This one-pot, two-step transformation requires only a single purification step. The resulting thiazolyl-substituted cyclopropanes were subjected to ring strain-release reactions, showing reactivity comparable to the parent cyclopropane-1,1-dicarbonitriles. Full article

To impart high flame resistance, enhanced thermal stability, and low dielectric properties to epoxy resin while maintaining good mechanical behaviors for high-end applications, a monomer (BZPN) containing the characteristic structure of benzoxazine, phthalonitrile, and trifluoromethyl was prepared and added into the Bisphenol A-type epoxy resin (DGEBA)/Dapsone (DDS) combination. The glass transition temperature (T_g) and carbon yield under a nitrogen atmosphere at 800 °C were found to significantly increase from 155 °C, 17.2% to 236 °C, 50.3%, respectively, for the neat EP/DDS and the BZPN-containing material. The UL-94 flammability rating achieved V-0 level when the BZPN content was 19.2 wt.% (EP-BZ-1). The thermal decomposition and flame retardancy mechanism were explored by TGA-FTIR, Raman, and XPS analysis. The fluorine-containing products were found in both the gas phase and the char residue, implying that the •CF₃ radicals played an important role in promoting the flame-retardant behaviors through a radical trapping mechanism. The dielectric constant and dielectric loss of the materials decreased as anticipated. In addition, mechanical testing of carbon fiber-reinforced composites showed that the BZPN-containing resin presented equivalent mechanical behaviors to the neat EP/DDS resin. The synthesized BZPN was proved to be an effective and promising additive for the epoxy-based composite. Full article

Element doping and functional group modification engineering serve as efficient approaches that contribute to the improvement of the functional efficiency in graphitic carbon nitride (CN) materials. A CN photocatalyst co-modified with sulfur (S) and cyano moieties was prepared through thermal condensation polymerization. The introduced S species modulated the band structure, increased charge carrier mobility, and significantly promoted charge separation and transport. Additionally, the introduction of cyano groups extended light absorption range and improved the material’s selective adsorption of reactant molecules. The as-prepared sulfur-modified CN photocatalyst obtained after a 6 h thermal treatment, which was capable of degrading organic pollutants and producing hydrogen (H₂) efficiently and stably, exhibited excellent catalytic performance. The photocatalyst’s photocatalyst exhibited a significantly enhanced photocatalytic activity, with a Rhodamine B (RhB) removal efficiency reaching 97.3%. Meanwhile, the H₂ production level reached 1221.47 μmol h⁻¹g⁻¹. Based on four-cycle experiments, the photocatalyst exhibited excellent recyclability and stability in both H₂ production processes and photocatalytic organic pollutant degradation. In addition, mechanistic studies confirmed the dominant role of ·OH and ·O₂⁻ as active species responsible for the reaction system’s performance. This study highlights that the co-decoration of heteroatoms and functional groups can markedly enhance the photocatalytic performance of CN-based materials, offering considerable potential for future applications in energy conversion and environmental remediation. Full article

Nitrile rubber (NBR) exhibits excellent oil resistance, wear resistance, gas barrier properties, and mechanical properties. On the other hand, lignin, a by-product of the pulp and paper industry, can serve as an ideal substitute for carbon black as a reinforcing agent for rubber. However, when NBR is directly compounded with lignin, direct compounding fails to achieve the desired reinforcing effect due to poor dispersion of lignin in the NBR matrix and poor compatibility with the NBR phase. In this paper, carboxyl groups were introduced via cyano group hydrolysis. By controlling the hydrolysis time, we successfully prepared two types of carboxylated NBR with different carboxyl contents. Subsequently, the carboxylated NBR was processed into lignin/NBR composites via dry blending. The results indicated that the introduction of carboxyl groups endowed NBR with higher polarity and reactivity, significantly enhancing the interfacial compatibility between lignin and the rubber matrix. The mechanical properties of the composite were greatly improved, with the mechanical strength increasing from 4.5 MPa without carboxyl groups to 13.8 MPa with high carboxyl content. The good dispersion of lignin also significantly improved the thermal stability of the composite. The carboxylation modification strategy of NBR provides a new approach for preparing high-performance NBR/biomass composites. Full article

Six new alkaloid compounds, including two rare aromatic nitrile compounds talaronitriles A–B (1–2), a novel oxime-functionalized azadiphilone analogue talarooxime A (3), a new phenylhydrazone alkaloid talarohydrazone E (4), and two new dipeptide compounds talarodipeptides A–B (5–6), were isolated from the deep-sea cold-seep-derived fungus Talaromyces amestolkiae HDN21-0307 via OSMAC approach. Compound 1 is the first natural naphthalene compound with cyano groups. Compound 3 represents the first natural product containing an oxime-functionalized azadiphilone scaffold. Their structures and absolute configurations were elucidated through spectroscopic data analysis and quantum chemical calculations. Notably, compound 3 demonstrated moderate DPPH free-radical-scavenging activity, with an IC₅₀ value of 29.41 μM. Full article

The radical-mediated intramolecular translocation of cyano groups has been recognized as a useful tool for the site-selective functionalization of organic molecules. The process is believed to proceed through the addition of an in situ-generated carbon-centered radical to the nitrile triple bond, followed by the β-scission of the resulting cyclic iminyl radical intermediate to relocate the cyano group and produce a more stable carbon radical for further elaboration. Beginning in the early 1960s and continuing for the next forty years, the research in this particular area has seen a surge of growth during the past two decades with advancements in radical chemistry and photocatalysis. The present article attempts to conduct a comprehensive review of existing studies on this topic by covering the literature from 1961 to 2025. The procedures developed for the purpose are grouped and discussed in four sections according to the strategies used to generate the initial carbon radicals, which include (i) hydrogen-atom transfer (HAT), (ii) radical addition to the π system, (iii) halogen-atom transfer (XAT), and (iv) the homolytic fission of a C-C single bond. In each section, a specific emphasis will be placed on reaction conditions, substrate scopes, and mechanisms. Full article

Over the past two decades, the copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition (CuAAC), commonly known as click chemistry, and C–H bond activation have gained significant attention and have emerged as key synthetic methodologies. In our efforts to synthesize fused nitrogen-containing heterocycles, we developed a palladium-catalyzed protocol for the synthesis of functionalized 7,10-dihydropyrrolo[3,2,1-ij][1,2,3]triazolo[4,5-c]quinolines and 5,8-dihydrobenzo[3,4][1,2,3]triazolo[4′,5′:5,6]azepino[1,2-a]indoles from suitable bromo-substituted N-propargyl-indoles. The reaction conditions demonstrate broad functional group compatibility including halogen, alkoxyl, cyano, ketone, and ester, affording the target compounds in good to high yields. Full article

Due to its unique molecular fingerprinting capability and multiplex detection advantages, surface-enhanced Raman scattering (SERS) has shown great application potential in the field of biological analysis. However, the weak signal intensity and large background interference significantly limited the application of SERS in biosensing and bioimaging. Loading a large amount of Raman molecules with signal in the silent region on the hotspots of the electromagnetic field of the SERS substrate can effectively avoid severe background noise signals and significantly improve the signal intensity, making the sensitivity and specificity of SERS detection remarkably improved. To achieve this goal, a new SERS signal-amplification strategy is herein reported for background-free detection of Cu²⁺ by using Raman-silent probes loaded on cabbage-like gold microparticles (AuMPs) with high enhancement capabilities and single-particle detection feasibility. In this work, carboxyl-modified AuMPs were used to enable Cu²⁺ adsorption via electrostatic interactions, followed by ferricyanide coordination with Cu²⁺ to introduce cyano groups, therefore generating a stable SERS signal with nearly zero background signals owing to the Raman-silent fingerprint of cyano at 2137 cm⁻¹. Based on the signal intensity of cyano groups correlated with Cu²⁺ concentration resulting from the specific coordination between Cu²⁺ and cyanide, a novel SERS method for Cu²⁺ detection with high sensitivity and selectivity is proposed. It is noted that benefiting from per ferricyanide possessing six cyano groups, the established method with the advantage of signal amplification can significantly enhance the sensing sensitivity beyond conventional approaches. Experimental results demonstrated this SERS sensor possesses significant merits towards the determination of Cu²⁺ in terms of high selectivity, broad linear range from 1 nM to 1 mM, and low limit of detection (0.1 nM) superior to other reported colorimetric, fluorescence, and electrochemical methods. Moreover, algorithm data processing for optimization of SERS original data was further used to improve the SERS signal reliability. As the proof-of-concept demonstrations, this work paves the way for improving SERS sensing capability through the silent-range fingerprint and signal amplification strategy, and reveals SERS as an effective tool for trace detection in complex biological and environmental matrices. Full article

Three diaryliodonium dicyanoargentates(I), [MesIAr][Ag(CN)₂] (Ar = Ph 1, Mes 2, 4-MeC₆H₄ 3; Mes = 2,4,6-Me₃C₆H₂), were prepared by anion metathesis. The X-ray structural analyses for these crystals revealed C–I^III∙∙∙N≡C halogen bonds (abbreviated as XB) between I atoms of diaryliodonium cations and N atoms of cyano groups, which provide different supramolecular organization. The noncovalent nature of these interactions was studied by density functional theory (DFT) calculations and topological analysis of the electron density distribution in the framework of the quantum theory of atoms in molecules (QTAIM) at the PBE-D3/jorge-DZP-DKH level of theory both in gas phase and crystal models. The philicities of partners in these contacts were confirmed by electron localization function (ELF) projections, electron density/electrostatic potential (ED/ESP) profiles, and Hirshfeld surfaces analysis. An analysis of the available crystallographic data from the literature allows us to find other examples of σ-hole interactions including the dicyanoargentate(I) anion, and the C–X∙∙∙N≡C (X = Br, I, Te) bonding were also confirmed theoretically. Full article

3-Chalcogenylindoles serve as crucial building blocks in organic synthesis and pharmaceutical chemistry. Herein, we describe a simple and general synthesis of 3-chalcogenylindoles through the direct C–H chalcogenation of indoles using N-selenophthalimide and N-sulfenylsuccinimide as chalcogenation reagents in the presence of CuBr₂ as the catalyst. The reactions were carried out in CH₂Cl₂ at room temperature under an air atmosphere with a low loading of catalyst, and a wide range of 3-selenylindoles and 3-thioindoles were obtained in good yields. Various functionalities, namely, methyl, methoxy, halo, ester, cyano, trifluoromethyl, and formyl groups on indoles, have shown amenability to the developed reaction. A mechanism involving the activation of the chalcogenation agent through CuBr₂ coordination with the amide carbonyl group is proposed. Full article

A novel method for the efficient and straightforward synthesis of tetrasubstituted furans is presented, employing a base-catalyzed reaction of α-hydroxy ketones and cyano compounds. The reaction proceeds under relatively mild conditions, utilizes readily available starting materials, and exhibits good functional group tolerance and high yields. Notably, this reaction obviates the need for expensive metal catalysts and introduces crucial functional groups such as amino and cyano moieties. Furthermore, it avoids the prerequisite functionalization of substrates, thereby enhancing atomic economy. Full article

The rapid and effective removal of pharmaceuticals and personal care products (PPCPs) from groundwater is challenging. In this paper, porous cyano group-rich g-C₃N₄ catalysts were prepared by urea (U) and a KOH-assisted thermal polymerization strategy. The thickness, active sites, and pores of g-C₃N₄ were successfully modulated by urea and KOH-assisted thermal polymerization. In addition, the charge separation efficiency of g-C₃N₄ was effectively improved by the above methods. We combine the g-C₃N₄ photocatalyst with peroxymonosulfate (PMS) to achieve the efficient degradation performance of ibuprofen. Meanwhile, we also explored the reaction mechanism of g-C₃N₄ in the photocatalytically coupled persulfate system, which illustrated the active roles of singlet oxygen and holes in the system in degrading pollutants. Our work demonstrates that the photocatalytically coupled persulfate system is an advanced technology necessary for the deep treatment of PPCPs in groundwater and suggests a feasible strategy for catalyst modulation. Full article

The potential migration of chemical compounds from plastic food packaging poses significant health risks, necessitating continuous monitoring and enhanced safety protocols. This study aimed to investigate the migration of nine chemical groups, including alanine, acetic acid, cyano derivatives, urea, amines, amides, benzene derivatives, nitrites, and non-specified compounds, across different food categories. A total of 195 packaged food samples from eleven food categories were analyzed using Headspace Gas Chromatography-Mass Spectrometry (GC-MS) to identify and quantify chemical migrants. Statistical analysis revealed significant differences in migration levels among food categories (p < 0.05). Cheese, candies, and chips exhibited the highest concentrations of alanine (65.95 ± 0.6384 mg/kg), acetic acid (57.80 ± 0.6383 mg/kg), and benzene derivatives (59.96 ± 1.844 mg/kg), respectively, while frozen raw meat and seafood showed the lowest levels for most compounds. High benzene and nitrite concentrations in certain samples raised particular concern due to their carcinogenic and toxicological effects. Regression analysis confirmed that food matrix type is a strong predictor of migration levels for several compounds. The findings emphasize the urgent need for stricter regulation, improved analytical techniques, and the development of safer packaging materials to reduce chemical migration risks and protect public health. Full article

Cyanobacterial harmful algal blooms (cyanoHABs) are a natural phenomenon produced mainly by the interaction between natural and anthropogenic events. CyanoHABs are characterized by the production of cyanotoxins that can have harmful effects on different species within the food web and even affect human health. Among the most prevalent toxin groups worldwide are microcystins (MCs), anatoxins (ATXs), cylindrospermopsins (CYNs) and nodularins (NODs), which are characterized as toxins with hepatotoxic, neurotoxic, and cytotoxic effects. This review summarizes and analyzes research on the influence of cyanoHABs, the main toxin-producing cyanobacteria and the most prevalent cyanotoxins in freshwater and marine bodies, highlighting their global occurrence, toxicology, and bioaccumulation dynamics in vectors of the food web, and the main cases of acute and chronic intoxications in humans. This review is useful for understanding the dynamics of cyanoHABs’ interaction with the ecosystem and their impact on human health, and how the implementation of a surveillance and management framework for cyanobacteria and cyanotoxins could generate vital information for stakeholders to establish health guidelines on the risks and hazards of cyanoHABs for the ecosystem and humans. Full article