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• A series of 2-mercapto-1,3,4-oxadiazole has been successfully synthesized. • All compounds underwent characterization using IR, NMR and Mass spectrometry. • These compounds were evaluated as urease inhibitors. • DFT used to predict the electronic, structural and spectroscopic properties. • The docking study contributed to the analysis of urease protein binding. In the present work seven derivatives (5a-5d and 6a-6c) of 2-mercapto-1,3,4-oxadiazole were synthesized by multistep reactions. After characterization through IR, EI-MS, 1H-, and 13C NMR spectroscopy, the synthesized compounds were screened in vitro against urease enzyme. Among the series, five derivatives 6c (IC 50 = 9.90 ± 1.92 µM), 6a (IC 50 = 10.65 ± 1.80 µM), 6b (IC 50 = 12.30 ± 0.99 µM), 5c (IC 50 = 12.57 ± 0.41 µM), and 5d (IC 50 = 16.96 ± 0.64 µM) attributed excellent inhibition effect excellent than the standard thiourea (IC 50 = 22.80 ± 2.20 µM). In addition, the remaining four compounds 5a, 5b, 4 , and 3 were found good inhibitors against the urease enzyme with IC 50 values of 23.23 ± 0.17, 25.20 ± 0.90, 31.40 ± 1.18, and 36.77 ± 1.03 µM respectively. The cytotoxicity assay revealed that the synthetic derivatives did not show any cytotoxic effect. DFT used to calculate frontier molecular orbital including; HOMO and LUMO to indicate the charge transfer from molecule to biological media, and MEP map to indicate the chemically reactive zone suitable for drug action. The results of docking and MD simulation indicate that most active mercapto-1,3,4-oxadiazoles have high binding efficiency to urease. The In silico ADMET indicated that 5a-d and 6a-c compounds did not exhibit carcinogenicity, mutagenicity or tumorigenicity. [Display omitted] [ABSTRACT FROM AUTHOR]

• N, N -carbonyldiimidazole was used to successfully obtain a choline betainate ester. • The formed N -Acylimidazolide intermediate reacts quickly to the choline betainate ester. • Choline betainate is cytotoxic for L929 mouse fibroblasts. • Antimicrobial activity against P. Aeruginosa and S. Aureus is significantly lower. In this work, choline chloride and betaine hydrochloride were condensed into a - to our knowledge - unreported choline betainate (N,N,N -trimethyl-2-oxo-2-(2-(trimethylammonio)ethoxy)ethanaminium chloride) using 1,1′-carbonyldiimidazole (CDI) activation of betaine hydrochloride in dimethylsulfoxide. The product and reaction intermediates were isolated, purified by preparative HPLC and analyzed in detail by infrared and nuclear magnetic resonance spectroscopy. The final product has a high cytotoxicity for L929 mouse fibroblasts, and low antibacterial activity against P. Aeruginosa and S. Aureus at concentrations of up to 20 mg/ml. It could potentially further be investigated for similar uses as suxamethonium chloride, a muscle relaxant drug. [ABSTRACT FROM AUTHOR]

• Synthesis of natural, cationic and zwitter ionic silicon phthalocyanines. • Generation of singlet oxygen species. • Exploration of photodegradation characteristics. • Investigation of sono-photodynamic properties. This study focuses on investigating the sono-photophysicochemical properties of recently synthesized and characterized di-axially substituted silicon phthalocyanine complexes, incorporating schiff-base groups and zwitter ions, imparting novel features and potential therapeutic applications. Specifically, our research focused on evaluating the suitability of these complexes for photodynamic therapy (PDT), sonodynamic therapy (SDT), and the emerging field of sono-photodynamic therapy (SPDT). The characterization process involved the application of various analytical techniques, including UV–Vis spectroscopy, infrared (FT-IR) spectroscopy, and proton nuclear magnetic resonance (1H NMR) spectroscopy. Experimental results displayed highly promising outcomes, revealing that the synthesized sensitizers exhibited exceptional efficiency in generating reactive oxygen species, a critical attribute necessary for effective therapeutic interventions. This finding significantly contributes to the development of novel therapeutic agents with enhanced photodynamic and sonodynamic properties. Harnessing the power of light and sound simultaneously through sonophotodynamic therapy offers a unique and synergistic approach, potentially amplifying the therapeutic efficacy of these complexes. The combination of sonochemical and photochemical applications produced better results, for the studied compounds, the quaternized complexes (cationic compounds) showed the higher result. Overall, the results suggest that SPDT is a promising combination therapy for cancer treatment. [Display omitted] [ABSTRACT FROM AUTHOR]

• A series of new hydrazones were synthesized with good yield. • Synthesized compounds were evaluated for antibacterial, anti-inflammatory, and anti-oxidant activities. • Upon comparing the synthesized molecules with the commonly prescribed medication Diclofenac sodium, we observed a significant enhancement in anti-inflammatory efficacy. • The synthesized compounds demonstrated a notable inclination for DPPH scavenging in the antioxidant assessment, further highlighting their potential in combating oxidative stress. • In silico molecular docking and dynamic investigations were performed to better understand the binding mechanism of the synthesized hydrazones with the target. Hydrazones, which are azomethine-containing active chemicals with a N(H)N CH group, are extensively researched due to their versatility in pharmacology and ease of synthesis. The synthesized hydrazone compounds were examined by FTIR, UV–visible, EI-MS, 1H NMR, and 13C NMR spectroscopy, and they possessed azomethine linkages. Using the disc diffusion process and minimum inhibitory concentration (MIC) techniques, the compounds were tested for their antibacterial activity. By using the denaturation of bovine serum albumin technique to the synthesized compounds, their anti-inflammatory properties were further examined. Comparing the synthesized molecules to the common medication diclofenac sodium, considerable anti-inflammatory efficacy was observed. Synthesized compounds' antioxidant results revealed a remarkable tendency for DPPH scavenging. Further in silico molecular docking and dynamic studies were evaluated to understand the binding mechanism of the synthesized hydrazones with the target. [Display omitted] [ABSTRACT FROM AUTHOR]

• Compilation of important results of investigations of the complexation chemistry, characterization, stability and photophysical properties of complexes of small ring benzo-oxa-crown ethers namely benzo15-crown-5, dibenzo-15-crown-5 and benzo-12-crown-4 with alkali metal ions in the solution state. • Results from techniques like UV, far-IR, Raman, 1H, 13C and multinuclei NMR that have been employed to confirm the formation of the complexes and designate their conformers in solution state are included in the review. • The solvent systems and binary and ternary mixtures of solvents employed to study these complexes have been reported in this review. • The complexation thermodynamics and results of experiments based on conductance properties, fluorescence responses and energy transfer mechanisms are also discussed in this paper. This review paper focuses on the past and recent investigations carried out in solution state to determine the complexation chemistry, characterization, stability and photophysical properties of complexes of small ring benzo oxa-crown ethers namely benzo - 15-crown-5, dibenzo-15-crown-5 and benzo-12-crown-4 with alkali metal ions. These crown ethers form stable complexes with physiologically important ions like Li+, Na+ and K +and mimic natural ionophores in this property. The experimental observations from UV–visible spectroscopy, IR spectroscopy, NMR spectroscopy, conductometry and calorimetry are useful in confirming the formation of these complexes. In addition to monitoring the complexation process, techniques like IR and NMR spectroscopy have helped to designate the conformers of the complexes in solution. These crown ethers have been used in developing functional materials such as ion sensors, fluorescent logic gates, oil/water emulsion separating agents and extractors of toxic ions like cesium from nuclear waste. The benzene moiety in these macrocycles enables them to act as fluorescent sensors for alkali metal ions. They make ideal candidates to anchor on nanoparticles for sensing alkali metal ions. The ring current in the benzene ring of benzo-crown ethers makes the carbon and protons nonequivalent and hence easily distinguishable by methods like 1H and 13C NMR spectroscopy as compared to 12-crown-4 and 15-crown-5. The solvent systems including binary and ternary mixtures of solvents employed in the study of these complexes have been reported in this review. Important aspects of complexation thermodynamics, fluorescence intensity altering processes and energy transfer mechanisms are also discussed in this paper. The dielectrics and donicity of the medium form an additional aspect of the review. These crown ethers form supramolecular assemblies with alkali metal halides and can therefore serve as good models to study and explore suitability of characterization methods for noncovalent interactions. [Display omitted] [ABSTRACT FROM AUTHOR]

• New isoxazolines were synthesized from nitriloxides and (E)-α-atlantone, a compound from Cedrus atlantica oil. • The reaction was both chemo- and periselective, yielding two distinct cycloadducts whose structures were determined using various analytical techniques. • The synthesized compounds exhibited significant antimicrobial activity against Staphylococcus aureus, Proteus mirabilis, and Candida albicans. • In silico investigations, including molecular docking, molecular dynamics and ADMET studies, were conducted to further understand the compounds' bioactivity at the molecular level. In the present work, new isoxazolines were semisynthesized by 1,3-dipolar cycloaddition reactions of nitriloxides on (E)-α-atlantone, a sesquiterpene compound isolated from Cedrus atlantica essential oil. The reaction proceeds in a chemo- and periselective manner to lead to two cycloadducts 3 and 3′. The structures of the obtained cycloadducts were determined using infrared, nuclear magnetic resonance spectroscopy, high resolution mass spectrometry, and elemental analysis. In addition, the semisynthesized cycloadducts were screened for their antimicrobial antibacterial and antifungal activities which they show significant diameter of inhibition zones ranging from 9 to 41.5 mm against Staphylococcus aureus, Proteus mirabilis , and Candida albicans. Furthermore, in silico investigations were conducted employing molecular docking, molecular dynamics, and (absorption, distribution, metabolism, excretion, toxicity) tests as well as drug-likeness evaluation, to complement the experimental findings and enhance our understanding of the potential bioactivity of the compounds at the molecular level. [ABSTRACT FROM AUTHOR]

• The molecular inclusion technology is used to convert the unstable liquid Perillaldehyde (PA) at room temperature into stable solid cyclodextrin inclusion complexes CDs-PA ICs. • 1H and 2D NMR studies reveal that PA molecule can enter the inner cavity from the wide rim of CD, mainly through hydrophobic interactions and size-matching effects. • The water solubility of α-CD-PA and β-CD-PA are increased (8 folds / 5 folds, respectively) with improved slow-release performances, especially favorable for applications as drugs. The compound Perillaldehyde (PA) is a bioactive constituent found in natural Perilla oil, exhibiting remarkable antibacterial and antioxidant activity. However, the instability of this compound caused by the easy oxidation of its aldehyde and olefin groups imposes limitations on its extensive applications. Therefore, it is crucial to develop effective strategies for enhancing the stability of PA. This study focuses on utilizing a series of natural cyclodextrins (CDs) to synthesize inclusion complexes (ICs) with PA, aiming to improve water solubility and achieve exceptional stability at room temperature, which is essential for their potential applications in biomedicine or food industries. The hydrophobic cavity of CDs can accommodate the hexatomic ring and hydrophobic chains of PA based on the well-known size-matching effect and hydrophobic interaction, thereby forming stable ICs. Additionally, the hydrophilic outer wall of CDs imparts excellent water solubility to ICs. Phase solubility investigations demonstrate successful construction of α-CD-PA IC and β-CD-PA IC with an inclusion ratio of 1:1. Their respective stability constant (K C) are determined as 342 L/mol and 180 L/mol, indicating superior stability for α-CD-PA IC compared to β-CD-PA IC. Conversely, γ-CD with a larger cavity fails to form a stable inclusion complex with PA due to inadequate size matching. Nuclear Magnetic Resonance Hydrogen Spectroscopy (1H and 2D NMR) studies reveal that PA enters the CDs cavity (α-CD or β-CD) from its wide rim with almost the entire molecule being obliquely embedded within it. Thermogravimetry Analysis (TGA) confirm that after inclusion with CDs, PA exhibits expected stability at 25 ℃. Furthermore, CDs-PA ICs demonstrate significantly improved water solubility compared to pure PA along with enhanced antioxidant activity and slow-release performance, rendering them highly favorable for various applications. [ABSTRACT FROM AUTHOR]

• Quantitative evolution of functional groups in coal molecular structure. • The crystallinity of coal shows two stages of change (critical point R o, max =2.00%). • Three-dimensional molecular structures of four types of coal were established. While extensive research has been conducted on the evolution of coal's molecular structure during coalification, the heterogeneity and complexity of coal continue to impede the accurate and precise quantitative characterization of its structural evolution mechanism. In this study, the organic matter source, coal quality, carbon skeleton structure, and functional group occurrence of coal at different coalification stages have been determined using maceral identification, vitrinite reflectance, industrial quality, elemental analysis, and spectral analysis. Four molecular models have been created through computer-aided molecular design. The results indicate that the hydrogen atoms in the benzene ring structure reduce as coalification increases. The content of aliphatic compounds gradually decreases, while the length of aliphatic side chains first decreases (R o,max <1.81%) and then increases (R o,max >1.81%). Moreover, the chemical structure of coal tends to mature and stabilize, as the degree of coal crystallization increases, and the oxygen-containing groups gradually decrease. Therefore, aromatization increases with the condensation reaction dominating in the late stage of coalification. After intensive attempts to determine the chemical bond mode between aromatic carbon, aliphatic side chain, and oxygen functional group, the final molecular structure models are presented as C 188 H 165 O 13 N 3 (F-1), C 182 H 161 O 9 N 5 (J-1), C 195 H 153 O 10 N 3 (T-1), and C 193 H 129 O 7 N 3 (W-1). Furthermore, the mechanism of coalification is discussed based on the variation of the side chains and chemical bonds. According to the adsorption heat of functional groups, the methane adsorption capacity increases as the degree of coalification increases. The inflection point of methane adsorption capacity is at R o,max >1.80%. This study provides a theoretical framework to understand the molecular structure evolution of coals at varying degrees of metamorphism. Additionally, it proposes a reliable method for characterizing coal molecular structures with high accuracy. [ABSTRACT FROM AUTHOR]

• Initial model pores with width < 1 nm. • Analyzing coal adsorption characteristics requires developing characteristic models. • Nitrogen adsorption isotherm of the 4 nm fracture pore model matches actual results. The present study aims to develop a tailored microscopic molecular model for analyzing the adsorption properties of Hongqingliang (HQL) coal. The chemical structure of the coal was thoroughly analyzed through the utilization of various techniques, including elemental analysis, Carbon-13 Nuclear Magnetic Resonance spectroscopy (13C NMR), X-ray Photoelectron Spectroscopy (XPS), and Fourier Transform Infrared Spectroscopy (FTIR). Subsequently, a three-dimensional periodic microscopic molecular model for HQL coal was constructed, followed by the development of a 4 nm fracture pore model. To validate the modeling approach, a comprehensive comparative analysis was conducted utilizing nitrogen adsorption isotherms at 77.35 K. The results indicate that the amorphous cell model constructed in Material Studio solely comprises micropores narrower than 1 nm, making it unsuitable for simulating coal's pore characteristics. Conversely, the nitrogen adsorption isotherm of the 4 nm fracture pore model matches actual results. Therefore, to analyze the pore adsorption characteristics of coal, it is necessary to utilize the amorphous cell model to construct a characteristic pore model for coal. [Display omitted] [ABSTRACT FROM AUTHOR]

• Raman, ATR-IR, LC-MS and 13C DEPT NMR spectra of HCTZ drug have been recorded. • DFT computations up to 6-311++G(d,p) basis set favors the gauche conformer. • Observed IR and Raman bands were assigned to their corresponding fundamentals. • Calculated structural parameters found in good agreement to X-ray values. • Unscaled force constants in internal coordinates were also determined. The Raman (4000-50 cm−1), attenuated total reflectance (ATR) infrared (4000-400 cm−1) spectra of Hydrochlorothiazide (C 7 H 8 ClN 3 O 4 S 2 ; HCTZ) have been recorded in the solid state in addition to LCMS in the dimer and trimer ranges. The 1H, 13C and 15N NMR spectra were also recorded in addition to DEPT (45, 90 and 135) of HCTZ sample dissolved DMSO‑d6. Initially, three conformers resulting from the rotation of -SO 2 NH 2 moiety around C 9 -S 11 were proposed, namely gauche, trans and cis conformers. And then Density Functional Theory (DFT) calculations for an isolated molecule were carried out employing both B3LYP and P3PW91 methods at 6-31G(d), 6-311+ G (d), 6–311++ G (d,p) basis set. The cis isomer is a transition state owing to the prediction of an imaginary wavenumber, while the gauche being more stable than trans by ∼438–538 cm−1 (∼1.25–1.54 kcal) employing the afore-mentioned computations. Moreover, we carried out a potential surface scan for the gauche to determine SO 2 NH 2 barriers to internal rotations and to ensure the optimal gauche is the most stable conformer. Aided by normal coordinate analysis (NCA) in addition to the atomic displacements in Cartesian coordinates (ADCC), confident vibrational assignment of the observed infrared and Raman bands are proposed for all fundamentals of the gauche rotamer. Nevertheless, force constants (FCs) in internal coordinates were also estimated using the above-mentioned methods and basis sets as well. The 1H, 13C and 15N chemical shifts were also correlated to their corresponding atoms. The results are reported herein and compared with HCTZ and its cocrystals whenever appropriate. [Display omitted] [ABSTRACT FROM AUTHOR]

• Biochar prepared from food waste at three typical pyrolysis temperatures, 350 °C, 450 °C and 500 °C, with 450 °C having superior adsorption properties. • Successfully constructed a molecular structure model consistent with the chemical properties of food waste biochar. • Provided a method of model construction for other biomass biochars. • The adsorption sites of pollutants are nitrogen- and oxygen-containing functional groups. • Alcohol hydroxyl and amino groups can bind better to Cu2+. Increasing urbanization has made it a serious challenge to deal with food waste (FW) from people and wastewater with pollutants from industry. Biochar from FW pyrolysis(FWB) can be used as an adsorbent to adsorb pollutants from wastewater, but its molecular structure is still unknown, limiting the understanding of its adsorption mechanism and its application in industry. In this paper, a series of combined methods of experimental characterization and quantum chemical calculations, such as solid-state 13C nuclear magnetic resonance spectroscopy (13C NMR), Fourier transform infrared spectroscopy (FTIR), and X-ray photoelectron spectroscopy (XPS) were used to investigate and successfully construct a model of the molecular structural features of FWB under the optimal contaminant adsorption preparation conditions. Based on the electrostatic potential distribution and adsorption experiments, the adsorption sites of the pollutants were elucidated. The results showed that the FWB prepared at different temperatures, 450 °C had a variety of oxygen-containing functional groups and polarity favorable for adsorption. In the molecular structure of FWB with the molecular formula C 60 H 49 N 7 O 8 , oxygen is present in the form of carboxyl, carbonyl, ether, alcohol hydroxyl, and phenol hydroxyl groups with numbers 1, 1, 1, 1, 2, 1, 2. Nitrogen is present in the form of pyridinyl nitrogen, pyrrolidinyl nitrogen, and primary amines with numbers 1, 1, and 5, respectively. In addition, nitrogen-containing and oxygen-containing functional groups are possible adsorption sites for pollutants on FWB, and alcohol hydroxyl and amino groups can bind better to Cu2+, which provides scientific guidance for improving the adsorption performance of biochar. This provides a solid foundation for the study of the microscopic adsorption mechanism of FWB and a method for the modeling of biochar from other biomasses. [Display omitted] [ABSTRACT FROM AUTHOR]

• Synthesis of N,N '-Carbonyl bis(carbamates), -(S -thiocarbamates) and N,N '-biscarbamoyl ureas. • Crystal structures have been elucidated together with enhanced hydrogen bonding network descriptions. • Hirshfeld surface analysis for short atom-atom interaction determination allows insight into molecular packing. • Vibrational spectroscopy agrees with X-ray crystal structure analysis and corroborates different hydrogen bonding modes. The three structural related compound classes of N,N '-biscarbamoyl ureas, N,N '-carbonyl bis(carbamates) and N,N '-carbonyl bis(S -thiocarbamates) have been intensively studied. 13C NMR spectroscopy shows a specific chemical shift for each compound class. In the solid state the molecules undergo intramolecular ring formation and additionally intermolecular dimer or strand building both via hydrogen bonds. The influence of the organic groups is showcased by Hirshfeld surface analysis and the study is rounded off by findings from IR spectroscopy. [Display omitted] [ABSTRACT FROM AUTHOR]

• BISHDZHI, an isoniazid derivative was synthetized. • Structural, spectroscopic, and pharmacokinetic analysis was carried. • BISHDZHI presents maximum absorption at the wavelength of 346 nm. • BISHDZHI + Fluconazole possesses antifungal action against Candida tropicalis. • BISHDZHI has excellent oral bioavailability and metabolic stability. In this work, the isoniazid derivative N',N'''-((1 E ,1′ E)-1,4-phenylenebis(methaneylylidene))di(isonicotinohydrazide) (BISHDZHI) was synthesized and characterized by Nuclear Magnetic Resonance (NMR), Attenuated Total Reflectance Fourier Transform Infrared spectroscopy (ATR-FTIR), Fourier Transform Raman (FT-Raman), and Ultraviolet-Visible (UV–Vis) spectroscopy, and its potential against fungal strains of Candida ssp. was evaluated by in vitro assays. The NMR spectrum confirmed the molecular structure of BISHDZHI. Quantum chemistry computational calculations allowed to obtain the potential energy surface, optimized molecular structure, and to identify all the bands of the Raman, infrared and UV spectra. The data calculated for isoniazid derivative BISHDZHI using the Functional Density Theory (DFT) are in accordance with the experimental values. Our in vitro studies showed that the BISHDZHI compound in association with Fluconazole possesses antifungal action against Candida tropicalis strain, with a reduction of the IC 50 24 times to the host. In silico study of ADMET suggested that BISHDZHI has excellent oral bioavailability and metabolic stability, which allows therapeutic action without severe risk to the host. In addition, the molecular docking showed a high interaction potential between the Candida Albicans target. While the molecular dynamics simulations suggested that the BISHDZHI ligand occasioned a minor change in the structure target, indicating more excellent stability than the drug fluconazole. [Display omitted] [ABSTRACT FROM AUTHOR]

• Tautomeric equilibrium in solution of kynurenic acid derivatives. • Use of NMR to study the behavior of kynurenic acid derivatives. • Correlation between experimental and computationally calculated NMR d values. The 4-quinolinone derivatives present a keto-enol tautomerism, which can be studied using different analytical techniques, including NMR. In this work, the spectroscopic study in solution of numerous derivatives with different substitution patterns in positions 1–4 of the quinolone rings, and their correlation with simulated spectra by density functional theory-gauge independent atomic orbitals method (DFT-GIAO) approximation is presented. Polyfunctionalized derivatives where the tautomeric equilibrium is blocked by N - or O -substitution allow us to observe the different behavior in chemical shifts by NMR. The study of some derivatives in the solid state by ss-NMR and X-ray Crystallography is also included. [Display omitted] [ABSTRACT FROM AUTHOR]

• The synthesis of TCKs is very simple and inexpensive method. • The antidiabetic activity of TCKs is superior to acarbose. • The TCK1 showed 5 hydrogen bonding interaction with α-amylase enzyme. • The binding energy of TCK2 with cyclooxygenase-2 is −10.02 kcal/mol. • All TCKs obey the lipinski rule and physiochemical pharmacokinetics parameters. Thiophenecarboxamide - α,β-unsaturated ketone (TCKs) hybrids were synthesized and scrupulously characterized by nuclear magnetic resonance spectroscopy (NMR) by the theoretical and experimental methods, Electrospray ionization mass (ESI-MS), Fourier transform infrared (FT-IR) and ultraviolet-visible spectroscopic techniques by experimental and theoretical methods. The anti-inflammatory and antidiabetic activities were tested for TCKs using protein anti-denaturation and the α-amylase inhibitory methods respectively. The molecular docking studies for TCKs were inspected and data were supported by their molecular parameters that were determined using density functional theory calculations (DFT). The obtained results of TCKs showed a lower band gap and higher electrophilicity index values. Molecular docking studies were investigated against the α-amylase and cyclooxygenase enzymes to compare the tentative results. The TCKs showed very good hydrogen bonding interactions with amino acid residues of the enzymes. In addition, ADMET study, Protox-II toxicity predictions were performed to check the pharmacological properties of TCKs. [Display omitted] [ABSTRACT FROM AUTHOR]

• Synthesis of 2-imino-thiazolidin-4-one derivatives via multi-step process. • Three key stages: preparation of starting material, chloroacetamido synthesis, and cyclization. • Structural determination through IR, 1H-NMR, and 13C-NMR spectroscopy. • Comprehensive analysis of intermolecular interactions, quantum parameters, and thermodynamics. • Highlighting robust hydrogen bonds, van der waals forces, and significant hydrogen bonding capabilities. In this study, outline the synthesis and spectroscopic characterization of novel 2-imino-thiazolidin-4-one derivatives. The synthesis process is divided into three main parts. Firstly, we prepared the starting material, 2-amino-4-(substitutedphenyl)-1,3-thiazole, by reacting thiourea with substituted acetophenone in the presence of iodine. The second part involved the synthesis of 2-chloroacetamido-4-(substitutedphenyl)-1,3-thiazole through the reaction of heterocyclic amine with chloroacetyl chloride in benzene. The third part focused on the cyclization reaction of synthesized intermediate compounds, leading to the formation of a new series of desired products, namely, 2-imino-3-[4-(substitutedphenyl)-1,3-thiazol-2-yl] thiazolidin-4-ones. The structures of the synthesized compounds were determined based on spectral data, including IR, 1HNMR, and 13CNMR. Various analytical methods were employed to explore intermolecular interactions, nonlinear optical properties, HOMO-LUMO energy gap, potential energy maps, Natural Bond Orbital (NBO) analysis, and thermodynamic parameters of diverse compounds. The assessment of weak intermolecular interactions using Noncovalent interactions (NCI) and reduced density gradient (RDG) methods revealed the presence of robust hydrogen bonds, van der Waals forces, and steric effects within the compounds. Topological parameters highlighted significant hydrogen bonding capabilities among the studied compounds. Additionally, the analysis of the HOMO-LUMO energy gap and other quantum chemical parameters unveiled the influence of protonation on polarization, chemical reactivity, and corrosion resistance. Molecular Electrostatic Potential (MEP) analysis indicated changes in electrophilicity and nucleophilicity upon the addition of protons, altering chemical reactivity. Stabilization energies of donor-acceptor interactions, assessed through Natural Bond Orbital (NBO) analysis, provided insights into charge transfer and conjugative interactions, particularly emphasizing electron delocalization within the compounds' phenyl rings. [ABSTRACT FROM AUTHOR]

• Three Pb(II) complexes with 3-(2-pyridyl)−5-(4-chlorophenyl)−1,2,4-triazine ligand. • Spectroscopic and structural studies of compounds. • DFT descriptors such as NBO, QTAIM, NCI, and IGM on the synthesized crystals. • Compare the DFT results of IR and 1H NMR spectra with the experimental data. Three new Pb(II) complexes of the ligand 3-(2-pyridyl)-5-(4-chlorophenyl)-1,2,4-triazine (pcpt) and different anionic co-ligands (1 : bromide, 2 : iodide and 3 : isothiocyanate) were synthesized and characterized by elemental (CHN) analysis, FT-IR and 1H NMR spectroscopy and single crystal X-ray diffraction (SC-XRD). Considering only strong primary coordination bonds, the Pb(II) centres in complexes 1 and 2 are holodirectionally and in 3 hemidirectionally coordinated by the organic pcpt ligands due to stereochemical inactivity (1, 2) and activity (3) of the lone electron pair. The primary coordination sphere in 3 is sterically suitable for establishing interactions at longer distances, where the Pb centre acts as Lewis acid. Thus, all the Pb centers participate in Pb⋅⋅⋅Cl tetrel interactions, which together with secondary interactions of the ligands extend the structures into 1D supramolecular assemblies. A Hirshfeld surface inspection, along with the natural bond analysis (NBO), quantum theory of atoms in molecules (ATAIM), molecular electrostatistic potential (MEP) surface, and theoretical vibrational analysis at B3LYP/Def2-TZVP level of theory were conducted for the sake of further investigation of the non-covalent interactions in complexes 1 – 3. An enrichment ratio is also calculated for the chemical species to determine the tendency of their interactions in the crystal packing. The theoretical values obtained from the DFT at B3LYP/Def2-TZVP level of theory ensure that the expected consequences match the experimental findings. The QTAIM calculations allow the estimation of the strength of the primary and secondary/tetrel interactions and to propose the theoretical criteria based on the |V BCP |/G BCP , H BCP / ρ BCP , and DI parameters for distinguishing the interactions. The MEP calculations confirmed the presence of a σ-hole in the proximity of the PbII centers. [Display omitted] [ABSTRACT FROM AUTHOR]

• MAOS approach was applied in the cross-coupling reactions leading to porphyrazines. • MAOS approach was used in the Paal-Knorr reaction towards diaminomaleonitriles. • Optical and electrochemical properties of porphyrazines were assessed. Cross-coupling Suzuki-Miyaura reaction using Microwave Assisted Organic Synthesis (MAOS) approach of phenylboronic acid and magnesium(II) porphyrazines with peripheral dimethylamino and 3,4-dibromo-2,5-diphenylpyrrol-1-yl or 3-bromo-2,4,5-triphenylpyrrol-1-yl groups led to magnesium(II) porphyrazines with dimethylamino and 2,3,4,5-tetraphenylpyrrol-1-yl groups. MAOS approach was also used in the Paal-Knorr reaction to synthesise the modified diaminomaleonitrile intermediates. All intermediates and macrocycles were characterized using UV-Vis, 1H and 13C NMR spectroscopy, as well as ES or MALDI MS spectrometry. The optical and electrochemical properties of obtained porphyrazine macrocycles were assessed. It was found that the susceptibility of new macrocycles to oxidation/reduction processes analyzed by cyclic and differential pulse voltammetry depended on the presence of bromide and the number of phenyl substituents in the macrocyclic periphery. [ABSTRACT FROM AUTHOR]

• Synthesis of salicylaldehyde-diclofenac hydrazone and its metal complexes. • Characterization of compounds using NMR, FTIR, and UV–Vis, XRD. • Evaluation of anti-inflammatory and antitumor activities. • Docking studies with COX-1, COX-2, HepG-2, and MCF-7 receptors. • Assessment of physicochemical properties, pharmacokinetics, and drug-likeness using computational methods. A novel hydrazone ligand was synthesized by condensing diclofenac hydrazide with salicylaldehyde. This ligand was then used to create complexes with cobalt(II), nickel(II), copper(II), gadolinium(III), lanthanum(III), and silver(I). Structural characterization of these compounds was achieved through various techniques, including nuclear magnetic resonance spectroscopy, infrared spectroscopy, ultraviolet-visible spectroscopy, mass spectrometry, elemental analysis, thermal analysis, magnetic susceptibility measurements, electron spin resonance spectroscopy, X-ray diffraction, and conductivity measurements. The inhibitory effects of the synthesized compounds on cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes, critical targets for anti-inflammatory drugs, were assessed. Notably, the cobalt(II) and silver(I) complexes exhibited high selectivity for inhibiting COX-2, with selectivity indices of 118.75 and 105.00, respectively. The antitumor potential of the compounds was evaluated against MCF-7 (breast cancer) and HepG-2 (liver cancer) cell lines. The copper(II) and gadolinium(III) complexes demonstrated the highest efficacy, significantly inhibiting the growth of both cancer cell lines with half-maximal inhibitory concentration (IC50) values as low as 0.37 µM and 0.58 µM (MCF-7) and 0.35 µM and 0.67 µM (HepG-2), respectively. These complexes outperformed the original ligand in inhibiting cancer cell growth. In silico studies, using the SwissADME web tool and AutoDocke Vina, corroborated the experimental findings and provided insights into the compounds' physicochemical properties, pharmacokinetics, drug-likeness, and potential binding interactions with COX-1, COX-2, and the target proteins in the cancer cell lines. [Display omitted] [ABSTRACT FROM AUTHOR]

• Synthesis of mixed ligand-metal complexes of Fe (II), Co (II), Cu (II), and Zn (II) with thiosemicarbazones is reported. • Antimicrobial activity and cytotoxicity of the synthesized ligands and complexes were tested. • The complexes were characterized by EDX, AAS, elemental analysis, FT-IR, molar conductivity, UVVis, 1H, and 2D- NMR. • Computational drug-likeness, molecular docking and DFT studies were also performed. This paper reports the synthesis and structural characterization of novel mixed ligand-metal complexes derived from 4-((2-(phenylcarbamothioyl)hydrazinylidene)methyl)benzoic acid (L 1) and 4-((2-carbamothioylhydrazineylidene)methyl)benzoic acid (L 2). The ligands, and their complexes with Fe(II), Co(II), Cu(II), and Zn(II) salts, were characterized using elemental analysis, FT-IR (Fourier-transform infrared spectroscopy), UV (Ultra-violet), 1H and 13C NMR (Nuclear Magnetic Resonance), EDX (Energy-dispersive X-ray spectroscopy), AAS (Atomic absorption spectroscopy) and molar conductivity measurements. Elemental analysis and conductance data confirmed the formation of non-electrolytic complexes in a 1:1:1 molar (L 1 :M:L 2) ratio. The ligands bound to the metal ions in a bidentate manner as shown by the IR spectral data. The complexes exhibited an octahedral geometry. DFT (Density functional theory) calculations at B3LYP/6-311++G(d,p) level supported the experimental findings. Molecular docking studies were performed with four antimicrobial protein targets mainly enoyl-acyl carrier protein reductases (PDB ID: 1D70 , 2WYW , 1P9G and 4XRE) to comprehend their binding with the chosen targets. Both the ligands were shown to be non-toxic as depicted by the cytotoxicity test performed using MTT assay. Antimicrobial activity evaluation revealed that the metal complexes exhibited enhanced activity as compared to the free ligands, with the Co(II) complex showing the highest inhibition zones. These findings suggest that the mixed ligand-metal complexes could also be explored for diverse applications. [Display omitted] [ABSTRACT FROM AUTHOR]

• A series of novel silver- N -heterocyclic carbene complexes are synthesized and characterized. • Very low catalyst loading (1 mol%) is required for the coupling of aldehydes, amines, and alkynes. • Catalysts are highly robust demonstrating excellent conversions. • The novel catalyst is highly active amongst the reported silver catalysts for A3 couplings. A mild catalytic protocol for aldehyde, amine, and alkyne coupling (A3-coupling) allows for the selective synthesis of propargyl amines using 5,6-dimethylbenzimidazole-derived N-heterocyclic carbene (BNHC) silver(I) catalysts. A series of BNHC Ag(Ⅰ) halide complexes were synthesized and their structures have been elucidated through the use of multinuclear NMR and FT-IR spectroscopy. Furthermore, the pseudo-linear geometry of two different compounds was substantiated by single-crystal X-ray diffraction. Silver-based A3-coupling was achieved for both acyclic and cyclic secondary amines using a diverse set of alkynes to afford propargyl amines with yields of up to 95 %. The present approach is environmentally benign and water is generated as the sole byproduct. [Display omitted] [ABSTRACT FROM AUTHOR]

• Novel spiropyranocoumarin and benzofuranyl coumarin scaffolds are synthesized. • Ninhydrin core is employed as the pivotal framework for assembling various phenols. • Spiro pyranocoumarin self-assembled to form sheet-like arrangement. • Benzofuranyl coumarin exhibited helix-like architecture in the crystalline state. • SEM images of spiropyranocoumarin and benzofuranyl coumarin showed flat fibrillar and vesicular morphology. Pyrano and furanocoumarins are oxygen-containing heterocycles frequently found in natural products and biologically active molecules. In the present work, ninhydrin core is employed for the first time as the pivotal framework to construct benzopyrano/furano coumarin skeleton. It has been found that substrates like phenol, p -/ m -cresol, m -methoxyphenol, p -chlorophenol etc. reacted with ninhydrin-4-hydroxycoumarin adduct 3 in AcOH/H 2 SO 4 to furnish a new class of spiropyranocoumarins 5a-f via condensation/cyclization sequence. Under similar conditions, reaction of adduct 3 with 3,5-dihydroxybenzoic acid delivered benzofuranyl coumarin 6 through ring closing/ring opening mechanism. Structures of the synthesized compounds were characterized by IR, 1H and 13C NMR spectroscopy. Single crystal X-ray diffraction study revealed that spiropyranocoumarin 5b self-assembled to form sheet-like arrangement. However, benzofuranyl coumarin 6 was found to display helix-like architecture in the crystalline state. Scanning electron microscopy (SEM) images of compound 5b exhibited flat fibrillar morphology, whereas compound 6 revealed formation of vesicular structure. These types of small heterocyclic molecules are decent candidates for producing promising soft materials. [Display omitted] [ABSTRACT FROM AUTHOR]

• This work examines some BODIPY-based calix[4]arene derivatives' effects on DNA. • Compounds 3, 7 and 9 binds to DNA with good binding constants. • The compounds showed a strong cleavage effect by breaking down the DNA. • Molecular docking for DNA interaction were also performed to have a good insight. This work includes the synthesis of some BODIPY-derived heterocyclic Calix[4]arene compounds and the investigation of their effects on DNA. Among the calixarene-BODIPY-based target compounds, compounds 3 and 9 were newly synthesized, and compound 7 was synthesized as given in the literature. The structures of all synthesized compounds were determined by elemental analysis and spectroscopic techniques (13C NMR, 1H NMR, FT-IR). The effects of the synthesized Calixarene/BODIPY compounds (3, 7, and 9) against ct-DNA were examined via UV–Vis spectrometric and fluorimetric methods. The obtained results indicated that compounds 3, 7, and 9 bind to DNA, and the calculated binding constants (K b) were found 1.62 × 103 M −1, 1.54 × 103 M −1, and 1.14 × 102 M −1 respectively. Also, the DNA cleavage activity was examined against pBR322 plasmid DNA. The results showed that all compounds (3, 7, and 9) had a quite high effect on pBR322 plasmid DNA. Molecular docking studies were also performed to gain insight into the binding affinities and key interactions of DNA-synthesized compounds. The strong binding of compounds to the DNA can be attributed to high negative values of binding free energy between -20.2 and -17.4 kcal mol−1. These results gave the idea that these molecules are candidate molecules, especially for anti-bacterial and anticancer studies. [Display omitted] [ABSTRACT FROM AUTHOR]

• The 2,4,5-triaryl imidazole derivative 3aa-3bg was synthesized by NCS as a catalyst. • Fe3+ ions could be quickly detected using probe 3bd with high selectivity and immunity to interference. • Fe3+ ions in HepG-2 live cells could be imaged by probe 3bd with low toxicity to cells. In this study, an efficient synthesis of 2,4,5-trisubstituted imidazoles was developed via cyclocondensation starting from o -dione, substituted aromatic aldehyde and ammonium acetate using catalyst NCS, and was characterized by HR-MS, FT-IR, 1H and 13C NMR spectroscopy. A novel fluorescence sensor 4-(1 H -phenanthro[9,10- d ]imidazol-2-yl)- N, N -diphenylaniline (3bd) was discovered for the detection of Fe3+ ions. The probe 3bd exhibited strong blue radiation in solution. In the presence of Fe3+ ions, a significant fluorescence change of blue light to green light was observed in the EtOH/H 2 O (4/1, v/v) solution of 3bd (Ag+, Al3+, Ba2+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, Hg2+, Mg2+, Mn2+, Pb2+, Sr2+, Zn2+). The limits of detection of probe 3bd for Fe3+ ions was calculated to be as low as 0.70 μ M, and it had excellent anti-interference ability. The probe 3bd complexed with Fe3+ ions at 1:1, and the complexation constant was 3.93 × 104 M−1. The probe 3bd realized the detection of Fe2+ oxidation to Fe3+, and the pH showed fine stability in the environment between 4.0–7.0, which ensured its potential application prospects. It also showed good reversibility upon addition of EDTA. Furthermore, the viability of 3bd to Fe3+ had practical application in live cell imaging. [Display omitted] [ABSTRACT FROM AUTHOR]

• A series of new symmetrical liquid crystal compounds with Schiff base linking unit attached to different terminal alkyl chains were synthesized and characterized. • The Schiff base compounds were found to exhibit mesomorphic properties of smectic C and nematic phases. • A long alkyl chain allows the compounds to adopt a lamellar arrangement, which promotes the formation of a smectic phase. • Incorporating the Schiff base into the molecules maintains an appropriate permanent dipole moment, allowing the homologs to align in a parallel orientational order and thus exhibit nematogenic properties. A series of new symmetrical liquid crystal compounds with Schiff base as a linking unit attached to different terminal alkyl chains were synthesized and characterized. The intermediates of 4-(decyloxy)benzaldehyde, 4-(dodecyloxy)benzaldehyde, and 4-(tetradecyloxy)benzaldehyde were synthesized through alkylation reaction between 4-hydroxybenzaldehyde with three series of bromoalkanes. Next, it further reacted with 1,4-phenylenediamine through condensation reaction to produce symmetrical Schiff base linkage with different terminal group chain which indicated as N -(substitutedbenxylidene)benzene-1,4-diamine. The compounds were characterized using Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance spectroscopy (NMR) and CHN elemental analysis. The Schiff base linkages are detectable in the FTIR spectra within the range of 1601–1604 cm⁻¹ and in the NMR spectra at δ 8.47–8.48 ppm. The mesophase transition phase of this compounds were determined using polarized optical microscope (POM) and further confirmed using differential scanning calorimetry (DSC). The Schiff base compounds were found to be mesogenic with smectic C and nematic transitions phases. These compounds attached to decyl, dodecyl, and tetradecyl terminal chains were found to exhibit smectic C phase at 142.47, 135.60, and 131.90 °C and nematic phase at 199.62, 197.11, and 188.76 °C, respectively. The incorporation of a Schiff base linking unit with a symmetrical alkyl chain induces the mesogenic effect in the molecules. A long alkyl chain allows the compounds to adopt a lamellar packing, facilitating the formation of a smectic phase. Incorporating the Schiff base into the molecules maintains an appropriate permanent dipole moment, which enables the homologs to arrange in a parallel orientational order, thereby adopting a nematogenic character. [ABSTRACT FROM AUTHOR]

• 2-Phenoxy-1-tetralones 5 have been synthesized as rigid analogs of 2-phenoxyacetophenones. • An oxime derivative 6 was selectively prepared and characterized as (Z)-isomer. • The conformational aspects of 5 and 6 were investigated by 1H NMR and DFT studies. • The more stable conformer of 5 showed an equatorial orientation of phenoxy moiety. • (Z)-oxime formation on the 1-position results in a conformational inversion of tetralin ring. A series of 2-phenoxy-1-tetralones have been synthesized as conformationally constrained analogs of bioactive compounds 2-phenoxyacetophenones. A representative oxime derivative of 2-(3-methoxyphenoxy)-1-tetralone was selectively prepared and its (Z)-geometry was characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy. Also, the conformational aspects of designed compounds were investigated by 1H NMR spectroscopy and density functional theory (DFT) calculations. The computational results showed that the more stable conformation in 5c is a conformer with equatorial orientation for 2-aryloxy group but the axial orientation in the related oxime 6 is predominated. Accordingly, it was demonstrated that the formation of (Z)-oxime on 1-position results in a remarkable conformational inversion on tetralin ring. [Display omitted] [ABSTRACT FROM AUTHOR]

• Five new pyrazole and pyrazolone derivative heterocyclic disperse disazo dyes, derived from the 4-position, were synthesised. • These dyes were characterised by elemental analysis, FT-IR, 1H NMR, and 13C NMR spectroscopy. • The effects of different solvents on absorption of the dyes were examined. • The effects of acid and base on absorption of the dyes were investigated. • Acute toxicity of each synthesised azo dye was assessed using Gammarus roeseli. In the present work, five novel heterocyclic disazo dyes (AA3a−AA3e) were synthesised. The characteristic properties of these synthesised dyes were examined, and their elemental analysis values were calculated. The dyes were characterised by the FT-IR, 1H NMR, and 13C NMR spectroscopy. The impacts of several solvents on the absorption abilities of the synthesised compounds were analysed by a UV–vis spectrophotometer. Also, the absorption properties and tautomeric changes of the dyestuffs in the existence of inorganic acids and bases were investigated. Apart from these analyses and examinations, given the possibility of their release into the environment especially during their potential subsequent applications, the acute toxicity of each synthesised dyes to Gammarus roeseli (Crustacea: Amphipoda) was tested in the study. The current study is of great importance in the sense that it gives precious information on the acute toxicity levels of the dyestuffs AA3a−AA3e as well as their synthesis and spectral properties. [Display omitted] [ABSTRACT FROM AUTHOR]

• Chiral tetradentate vanadium(V) Schiff base complexes have been synthesized. • The complexes were characterized by IR, CD, UV–vis and NMR spectroscopy. • Catalytic potential have been studied in the oxidation of alkenes and monoterpenes. • Biological properties in relation to their cytoprotective activity have also been determined. New mononuclear oxidovanadium(V) complexes, [(−)VOL1–10] and [(+)VOL1–4] , with chiral tetradentate Schiff bases have been obtained by monocondensation of salicylaldehyde derivatives and optically active amino alcohols, i.e. 1R,2R -(−)-2-amino-1-phenyl-1,3-propanediol or 1S,2S -(+)-2-amino-1-phenyl-1,3-propanediol. All complexes have been characterized by elemental analysis, circular dichroism, UV–vis, IR, 1D (1H, 51V) and 2D (COSY, NOESY) NMR spectroscopy. The catalytic activity studies have also been performed for all complexes in the epoxidation of styrene, cyclohexene and two monoterpenes, i.e. S (−)-limonene and (−)-α-pinene, using aqueous 30 % H 2 O 2 or tert -butyl hydroperoxide (TBHP) as the terminal oxidant. In addition, biological properties of these chiral oxidovanadium(V) compounds, as well as cis -dioxidomolybdenum(VI) complexes with the same chiral Schiff bases, were studied in relation to their cytoprotective activity against the oxidative damage generated exogenously by 30 % hydrogen peroxide in the HT-22 hippocampal neuronal cells. The latter compounds have revealed distinct cytoprotective properties causing the highest increase in the viability of HT-22 cells. Concentration dependent effect in the range of 10-100 μM concentration of the investigated compounds has also been observed. [ABSTRACT FROM AUTHOR]

• Mn(II), Co(II), Ni(II), Cu(II) and Zn(II) complexes of 1,2-benzothiazine based ligand. • Hirshfeld surface analysis for the copper complex. • DFT studies of 1,2-benzothiazine derived Cu(II) complex. • Antibacterial studies of metal complexes was carried out. The 2-benzyl-4‑hydroxy-1,1-dioxo-1,2-benzothiazine-3-carboxylic acid methyl ester i.e., ligand 1 was utilized to synthesize Mn(II) 2 , Co(II) 3 , Ni(II) 4 , Cu(II) 5 and Zn(II) 6 derived metal complexes in mild basic conditions. The structural investigation was carried out by UV–vis, FT-IR, NMR spectroscopy, CHN analysis, conductivity measurement, ESI-MS analysis and magnetic susceptibility techniques. The X-ray diffraction analysis confirmed the octahedral and distorted square pyramidal geometries of the cobalt and copper complexes. The ligand 1 coordinated with metal centres through enolic oxygen atoms of the thiazine ring and ester group while methanol coordinated with metal center via oxygen atom. The Hirshfeld surface analysis (HSA) was utilized to determine the intermolecular interactions. In support of the experimental data, DFT studies were also performed for the cobalt and copper complexes. The NBO analysis resulted in the large stabilization values 11.91 and 12.35 kcal/mol for the cobalt and copper complexes. The global reactivity indicated the higher values of hardness and the large values of FMO analysis which support the higher stability of the metal complexes. The synthesized compounds were also evaluated against six bacterial strains to check their antibacterial potential. It was observed from results that highest activity was depicted by copper complex 5 against B. subtilis and the zone of inhibition is 23.4 ± 0.6 mm which is comparable to ampicillin (standard drug). [ABSTRACT FROM AUTHOR]

• Experimentally as well as theoretically in-depth, complexes are thoroughly characterized. • Various thermodynamic parameters were assessed through the application of spectroscopic methods. • Theoretical study via DFT predicts inclusion phenomena. This investigation involved the inclusion of the antidepressant drug amoxapine (AXP) and gamma-cyclodextrin host molecules using a co-precipitation technique to produce a supramolecular complex. The objective was to acquire a more profound comprehension of the construction and long-lasting nature of the inclusion complex (IC) on a physical scale. The resultant hybrid underwent thorough characterization employing various methods including 1H nuclear magnetic resonance (1H NMR), electrospray ionization mass spectrometry (ESI-MS), and UV-VIS spectroscopy. A stoichiometric ratio of 1:1 was determined through Job's plot, and binding constant values were obtained using UV-VIS spectroscopic titrations with the assistance of the Benesi-Hildebrand technique. The experimental observations were supported by the ESI-MS data. The inclusion complexation was validated through a meticulous analysis of the results from molecular modeling. The preliminary computational screening via DFT revealed the stability of the amoxapine- γ cyclodextrin IC based on adsorption energy calculation. Furthermore, the inclusion complexation phenomenon was confirmed by the outcomes of 1H NMR and ESI-MS studies. The computational findings aligned consistently with the experimental data, providing substantiation for the encapsulation of amoxapine within γ -cyclodextrin. [Display omitted] [ABSTRACT FROM AUTHOR]

• In this work, a symmetrically di-butylatedlower rim and di-formylatedupper rim p - t -butyl-calix[4]arene was synthesized from p - t -butyl-calix[4]arene in the presence of butylbromide and potassium carbonate followed by duff reaction. • All compounds were characterized using various techniques, including FT-IR, 1H NMR, 13C NMR and mass spectroscopies along with X-ray crystallography (only for final product). • In the crystal network of final compound, in addition to the hydrogen bonds, there are π – π stacking interactions between formylated phenol rings. • The ability of calix[4]arene derivatives to interact with ten biomacromolecules was investigated by docking calculations. In this work, a symmetrically di-butylated (lower rim) and di-formylated (upper rim) p - t -butyl-calix[4]arene was synthesized using the following methods. Firstly, p - t -butyl-calix[4]arene (1) was synthesized, and then its two eclipsed hydroxyl groups at the lower rim were butylated by butylbromide to form di-butyl- p - t -butyl-calix[4]arene (2). The formyl group was then inserted into the upper rim of 2 using the Duff reaction with hexamethylene tetramine and finally di-butylated, di-formylated p - t -butyl-calix[4]arene (3) was formed. Compounds 2 and 3 were characterized using FT-IR, 1H NMR, 13C NMR and Mass spectroscopies along with X-ray crystallography (only for 3). In the crystal network of 3 , in addition to the hydrogen bonds, there are π – π stacking interactions between formylated phenol rings. For evaluating the ability of the compounds 1 − 3 to interact with ten biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR, TS, Top II and B-DNA), docking calculations were run and compared with that of the anticancer drug, doxorubicin. [ABSTRACT FROM AUTHOR]

• Synthesis of o-cresolphthalein based 1,2,3-triazole appended derivative (CT). • Characterization of the synthesized compound via spectroscopic techniques. • Ion sensing analysis of CT via UV–visible spectroscopy. • In silico analysis to explore pharmacokinetics of CT. • Molecular docking analysis of CT with aromatase. The present study demonstrates the synthesis, characterization, and multifaceted applications of a 1,2,3-triazole derivative synthesized via Copper(I)-Catalyzed Azide-Alkyne Cycloaddition (CuAAC). The design of the probe was carried out using o-cresolphthalein moiety, owing to its substantial absorption and emission behaviour, which was connected to a benzyl group (which acted as the transducer group) via a 1,2,3-triazole bridge. This bridge, in addition to serving as the spacer unit, also had the potential to provide the receptor sites for the metal ions due to the presence of N atoms having lone pairs of electrons. The compound's structural integrity was confirmed through Infrared (IR) Spectroscopy, Nuclear Magnetic Resonance (NMR) Spectroscopy, and Mass Spectrometry analyses. Its selective responsiveness to Pb(II) ions, established by UV–vis spectroscopy, revealed its potential as a robust Pb(II) ion sensor with a limit of detection of 11.2 µM and binding constant (K a) value of 3.2 × 104 M−1, thereby facilitating applications in environmental monitoring and analytical chemistry. Additionally, the compound's versatility extends to the realm of biology, as indicated by the in silico pharmacological studies and molecular docking simulations. These investigations underscored its significant potency as aromatase inhibitor, suggesting opportunities for therapeutic interventions and drug development, as the compound's molecular architecture and distinctive binding interactions offer promise in addressing intricate biological processes. [Display omitted] [ABSTRACT FROM AUTHOR]

• New 1,2-di(oxo/amino)-1,2-diborolan derivatives were synthesized and characterized. • Diboranes showed high activity against some clinically important Gram positive and negative bacteria and Candida species. • They showed strong activity against drug-resistant S. aureus ATCC 43300 and E. faecalis ATCC 51575 bacteria. A good yield of 1,2-diborolanderivatives 2-8 was obtained from the reaction of 1,2-dichloro-1,2-diborolane 1 and R 2 NLi/ArNHLi/PhOLi/H 2 O. The structures of these new derivatives were characterized by nuclear magnetic resonance spectroscopy. The molecular structures of 4 and 7a were also determined using single-crystal X-ray diffraction. The antimicrobial activities of synthesized compounds were tested against clinically important Gram-positive, Gram-negative bacteria, and Candida species. The most effective substances were found to be compounds 2, 3, 4, 6 and 8 among the tested compounds. Therefore, the activity of these substances were investigated against Staphylococcus aureus ATCC 43300 and Enterococcus faecalis ATCC 51575, which form biofilms and have antibiotic resistance. Compound 2, 6 and 8 appears to be a promising candidate for potential antibacterial agents against these bacterial strains, especially given its potent activity against biofilm-forming and antibiotic resistant strains. The results indicate that these new materials will be evaluated as potential drugs against infectious diseases in the future. New 1,2-di(oxo/amino)-1,2-diborolan derivatives were synthesized and characterized. Compounds 2,3,4,6, and 8 were signified forceful action against clinically important some Gram positive, Gram negative bacteria and Candida species. Their very high effects were remarkable against Staphylococcus aureus ATCC 43300 that cause skin enfection and Enterococcus faecalis ATCC 51575 causing endocarditis. [Display omitted] [ABSTRACT FROM AUTHOR]

Graphene nanoribbons (GNRs) have recently garnered significant attention due to their potential applications in transistors, photovoltaics, and quantum electronic devices. Cove-edged graphene nanoribbons (CGNRs) are particularly intriguing due to their unique electromagnetic properties. These nanoribbons, characterized by asymmetric edges composed of alternating hexagons, exhibit exceptional electronic properties. In this study, we employed a variety of degree and degree-sum-based topological descriptors (TDs) to calculate the topological entropy measures of CGNRs. The explicit mathematical formulae of the TDs for the CGNRs were derived using the edge partition method. Additionally, we determined the spectral diameters, delocalization energies, resonance energies, and HOMO-LUMO gaps to assess these compounds' thermodynamic and kinetic stabilities. We also utilized NEWGRAPH and MATLAB software to predict the NMR patterns for the CGNRs. The shallow HOMO-LUMO gaps in these calculations suggest that CGNRs are promising candidates for topological spintronics applications. • This manuscript reports the topological entropy measures and various properties of CGNRs. • Optoelectronic properties of CGNRs which would serve as important reference for future CGNR design and synthesis. • NMR signals and intensity patterns. [ABSTRACT FROM AUTHOR]

• Solvent free multicomponent protocol for novel 2-amino-4 H -chromene derivatives. • Structure determination by IR, mass, 1H & 13C NMR spectroscopy and elemental analysis. • Significant in vitro antidiabetic activity with more than 50 % α-amylase inhibition at the dose of 10 µg/mL and competitive inhibitor of enzyme. • Compound 5b more potent than acarbose with IC 50 of 3.60 ± 0.01 µg/mL. • In silico properties of compound 5b regarded as non-toxic and safer antidiabetic agent. Despite a wide range of kinase inhibitory activities exhibited by 2-amino-4H-chromenes, their potential application towards α-amylase inhibition remained rarely explored to date. For that purpose, a series of new 2-amino-7-(bis(2-hydroxyethyl)amino)-4(phenyl)-4H-chromene-3-carbonitrile derivatives has been synthesized via piperidine catalyzed solvent-free protocol and evaluated for their antidiabetic activity as potential α-amylase inhibitors. The dose-dependent in vitro α-amylase inhibition study revealed that, most of these compounds exhibited significant antidiabetic activity having more than 50 % α-amylase inhibition at the dose of 10 µg/mL. Among these, compound 5b was more potent than acarbose with 91 % inhibition of α-amylase and IC 50 of 3.60 ± 0.01 µg/mL. Enzyme kinetic studies to estimate mode of inhibition showed that inhibition of α-amylase by compound 5b was competitive type with a Ki value of 0.97 µg/mL. Further, in silico studies of targeted compounds reinforced the results being involved in favorable binding interactions within the active site of α-amylase. Moreover, the in silico predicted properties of compound 5b regarded as a non-toxic and safer antidiabetic agent. [Display omitted] [ABSTRACT FROM AUTHOR]

• Furazan - triazole compounds with multiple amino groups are stable and have good detonation performances. • Rapid preparation of azo compound by one step and get two azide groups. • Metal-free azo compound is potential substitute compound of lead azide. To balance the properties and stability of the energetic materials, the synthesis of the new energetic materials 3-amino-4-(4-amino-5-hydrazine-1,2,4-triazole-3-yl) furazan and its energetic salts were reported which show excellent performance and safety. Also, the azo compound 1,2-bis(4-(5-azido-1,2,4-triazol-3-yl) -furazan-3-yl) was prepared and got two -N 3 groups unexpectedly. All the new compounds were fully characterized by nuclear magnetic resonance spectroscopy (NMR) and infrared spectroscopy (IR), elemental analysis (EA), and differential scanning calorimetry (DSC). In addition, the structure of compounds 2, 4, 7 were confirmed by single crystal X-ray diffraction analysis. The X-ray date shows that energetic salts have extensive hydrogen bonds which are good to the stability of these energetic salts, and it also shows that azo compound has two conformations. In order to get detonation properties of these synthesized compounds, EXPLO5 was used to calculate. According to the calculated results, all ionic salts are inductive energetic materials with good detonation performances (D= 8064-8698m s−1, P= 25.8-31.8GPa) and azo compound has the detonation speed of 8190 m s−1 and achieved the detonation pressure at 24.9GPa. Additionally, the azo compound was tested through the initiation test which shows that it has good detonation ability, has the chance to be the green metal-free primary explosive. [Display omitted] [ABSTRACT FROM AUTHOR]

• A series of platinum (II) dihalides complexes employing a scorpinate ligand have been synthesized and characterized. • The molecular structure of all platinum (II) complexes displays one Pt•••H δ –C(sp3) anagostic interaction. • The platinum atom in all complexes adopts a square pyramid geometry. The platinum complexes 1 – 3 derivates of the ligand 2,2–bis(3,5–dimethylpyrazol–1–yl)–1– p –tolylethanol (L1) revealed the existence of one Pt•••H δ –C(sp3) anagostic interaction which was elucidated in solution by NMR spectroscopy, in solid state by single crystal X–ray diffraction analysis and by Bader's quantum theory of atoms in molecules (QTAIM) and non–covalent interaction (NCI) analysis. The molecular structure of complexes 1 – 3 shown that ligand L1 acts towards the metal center with a κ 3– NN H tridentate fashion via two nitrogen atoms and one δ –anagostic interaction (Pt•••H δ). The metal center adopts a square pyramid geometry. The distances of the Pt•••H δ anagostic interactions are having values from 2.625 to 2.635 Å. [Display omitted] [ABSTRACT FROM AUTHOR]

• The coordination ability of 1,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)butane ligand toward dichloride palladium (II) and platinum(II) has been investigated. • The molecular structure of palladium (II) and platinum(II) complexes displays two M•••H γ –C(sp3) anagostic interactions. • The palladium (II) and platinum(II) atoms in the complexes adopt a trigonal prism geometry. Two nine-membered metallocycles of PdII (1) and PtII (2) containing 1,4-bis(3,5-dimethyl-1H-pyrazol-1-yl)butane ligand (L1) have been prepared and their structures were determined by IR, NMR spectroscopy, and by single-crystal X-ray diffraction analysis. The molecular structures of L1 display that the pyrazolyl groups adopt an anti -conformation, while in 1 and 2 a discrete nine-membered monometallic macrocycle is generated by the assembly of one ligand and one metal atom, and the ring adopts a twist-chair-boat conformation. The ligand L1 in complexes 1 and 2 acts as cis- chelating ligand via a κ2 N,N coordination mode by the nitrogen atoms of the pyrazolyl rings. In compounds 1 and 2 the metal center adopts a planar geometry. The molecular structure of 1 and 2 also revealed two intramolecular anagostic interactions M•••Hγ–C(sp3) (M = Pd and Pt) with M•••H distances between 2.689 and 2.780 Å, which are important to stabilize the nine membered ring formed. Considering those two M•••Hγ interactions, the ligand L1 generates a κ4 N,N,H,H coordination mode and the metal centers adopt a trigonal prism geometry. The crystal packing of L1, 1 and 2 displayed supramolecular networks promoted mainly by C–H•••π interactions, which were analyzed by Hirshfeld Surface Analysis [Display omitted] [ABSTRACT FROM AUTHOR]

• Rimonabant lactam metabolite was first identified by single-crystal X-ray study. • The distribution of Rimonabant metabolites were tested in-vivo by LC–ESI–MS. • BBB permeability of lactam metabolite was lower than Rimonabant. • Oxidized lactam metabolite was more stable and reduced brain penetrance. The convenient oxidation was carried out to Rimonabant and its analogue with m CPBA for the formation of their reactive biological metabolites. The lactam oxidized Rimonabant metabolite was first successfully synthesized for demonstrating the construction and characterized by NMR spectroscopic methods and the single-crystal X-ray diffraction study. Through metabolism study of Rimonabant in vivo in mice, the lactam metabolite belongs to one of many high levels of reactive oxidized Rimonabant metabolites. On the other hand, the lactam metabolite is the most stable form in snapshot PK test and displays markedly reduced brain penetrance. [Display omitted] [ABSTRACT FROM AUTHOR]

• A promising strategy for high-energy insensitive materials. • An energetic salt with excellent performance based on furazan derivate. • Abundantly strong hydrogen bond network. • Sufficient structure characterization and analysis. • Visual analysis of weak interaction. Exploring new energetic materials with high energy and high stability is a long-term goal in the field of energetic materials. Crystal engineering is recognized to be a promising strategy for balancing energy capability and safety. In this study, newly designed 1:1 energetic salt (compound 2) constructed by pairing 3-amino-4-(4,5-diamino-1,2,4-triazole-3-yl)-furazan with 4-amino-1,2,5-oxadiazole-3-carboxylic acid was achieved by the simple acid−base reaction method. The structure of target compound was determined and characterized by nuclear magnetic resonance (NMR) spectrometers, Infrared (IR) spectroscopy, differential scanning calorimetry (DSC), simultaneous thermal analyzer (TGA-DSC) and single-crystal X-ray diffraction. It was found that compound 2 possesses desirable face-to-face π-stacking, which promote molecular stability. The structure-property relationship was investigated from experimental results and quantum chemical calculations. The ideal structure gives rise to high energetic performances (D = 8545 m s−1; P = 30.4 GPa), good thermal stability (T d = 236.6 ℃) and low sensitivity (IS = 34 J, FS = 350 N). These fascinating results suggesting that two dimension (2D) planar stacking could effectively modulate energy and safety. [ABSTRACT FROM AUTHOR]

• Herein, we reported the synthesis of nine new PEPPSI-Pd(II)–N-heterocyclic carbene (NHC) complexes 3a-h containing benzimidazole core and examined their catalytic activities in the direct arylation of heteroaromatic species with aryl bromides and arylchlorides. • Their structures were elucidated by 1H and 13C NMR spectroscopy, FT-IR spectroscopy, and elemental analysis methods. • Further, direct arylation reaction, using KOAc as base and DMAc as solvent under inert conditions, were carried out with the synthesized complexes in the presence of various aryl bromides and chlorides. Herein, we reported the synthesis of nine new PEPPSI-Pd(II)–N-heterocyclic carbene (NHC) complexes 3a-h containing benzimidazole core and examined their catalytic activities in the direct arylation of heteroaromatic species with aryl bromides and arylchlorides. Nine new Pd benzimidazole complexes were synthesized and their structures were elucidated by 1H and 13C NMR spectroscopy, FT-IR spectroscopy, and elemental analysis methods. In the 13C NMR spectra, N C HN peaks of Pd(II) complexes were observed between 159.7–161.5 ppm. Further, direct arylation reaction, using KOAc as base and DMAc as solvent under inert conditions, were carried out with the synthesized complexes in the presence of various aryl bromides and chlorides, and 2-acetyl furan, and furfuryl acetate 2-acetylthiophene and N-methylpyrrole-2- carboxaldehyde. Moreover, moderate to hig yields were obtained in the direct arylation of heteroarenes and aryl bromides under 1 mol% catalyst loading at 150 °C for 2 h loading conditions. The results showed that electron-donating and electron-withdrawing substituents on the aryl halides might produce coupling products in good yields in the presence of complexes 2a-d. Taken together, our findings are expected to contribute to the synthesis and design of palladium complexes containing benzimidazole core structures. [ABSTRACT FROM AUTHOR]

• Supramolecular self-assembly between cyclopentanocucurbit[6]uril and 1 H -benzotriazole. • Supramolecular framework of BTA@CyP 6 Q[6] has obvious pore structure. • CyP 6 Q[6] combines with TBA through an enthalpy driven process to enhance the thermal stability of TBA. In this paper, the host-guest supramolecular interactions between cyclopentanocucurbit[6]uril with 1 H -benzotriazole (BTA) have been investigated using 1H NMR spectroscopy, isothermal titration calorimetry (ITC), HPLC-QTOF mass spectrometry, IR spectroscopy, thermogravimetric analysis and single crystal X-ray diffraction. The results show that there is a 1:1 mode of inclusion in BTA@CyP 6 Q[6], which forms a supramolecular framework through hydrogen bonds and dipole interactions. In addition, the benzene ring of the BTA molecule entered the cavity of CyP 6 Q[6], while the triazole part resided at the port of the CyP 6 Q[6]. According to the ITC data, the complexation process for BTA with CyP 6 Q[6] is mainly driven by enthalpy. [Display omitted] [ABSTRACT FROM AUTHOR]

• The molecular structure characteristics of 3 different rank coals were explored. • Three coal molecules of different coal grades were constructed. • The molecular models of three different coal grades were optimized. To investigate the structural properties of coal molecules with different degrees of metamorphism, in this study, we used Fourier transform infrared spectroscopy (FT-IR), X-ray photoelectron spectroscopy (XPS), X-ray diffraction (XRD), and solid-state nuclear magnetic resonance carbon spectroscopy (13C NMR) to investigate the structural properties of three coal molecules with different degrees of metamorphism and finally constructed and optimized the coal molecular model. The experimental results showed that with the deepening of the deterioration degree, the proportion of oxygen-containing functional groups in the coal molecules was gradually reduced, the long fatty chains were shortened and reduced, and the aromaticity was enhanced. With increasing coalification, pyridine nitrogen and thiophene sulfur are becoming important components of the nitrogen- and sulfur-containing organic matter in coal. Coal metamorphism promotes the aromatization and condensation degree increase of coal molecular structure, which makes the coal molecular structure evolve into a microcrystalline structure with higher order degree. With this increase of coal rank, the carbon ratio around the bridge (X BP) increased from 0.12 to 0.47. The low-rank coal was dominated by benzene rings with low polymerization degree, and the high rank coal was dominated by aromatic structures, such as tetracene with a high degree of polymerization. The molecular formula of lignite finally constructed was C 219 H 159 O 21 N 3 , that of coking coal was C 235 H 164 O 7 N 4 S, and that of anthracite was C 286 H 108 O 5 N 4 S. The coal molecules constructed in this study provide a theoretical basis for the study of the molecular structure properties of coal with different degrees of metamorphism. [ABSTRACT FROM AUTHOR]

• A potentially genotoxic impurity E (Imp-E) of avanafil was synthesized, and its single crystal was cultivated by solvent volatilization method. • The structure of Imp-E was analyzed by HRMS, NMR and XRD, its absolute configuration was determined as S configuration. • Imp-E molecules have intramolecular / intermolecular hydrogen bonds, which make the molecules maintain a stable arrangement in space. In the classical route of synthesizing of avanafil, the last step of the reaction uses EDCI and HOBT as an acid and amine binding agent. HOBT may contain residues of hydrazine, and potential mutagenic impurities containing acylhydrazide structures may be formed. The intermediate product (M6) of avanafil was synthesized by 6 steps using diethyl ethoxylmethylmalonate and S-methyl isothiourea semisulfide as starting materials. The potentially genotoxic impurity E (Imp-E) of avanafil was given by the reaction of M6 and hydrazine sulfate acid amine, yield of 20%. The single crystal of Imp-E was cultivated by solvent volatilization method, and its structure was analyzed by high resolution mass spectrometry (HRMS) and nuclear magnetic resonance spectroscopy (NMR). The Flack parameter of Imp-E was -0.03(3) by X-ray single crystal diffraction analysis, and the absolute configuration of Imp-E was determined as S configuration. The intramolecular / intermolecular hydrogen bonds of Imp-E make the molecules maintain a stable arrangement in space. Molecular structure perspective of Imp-E (S configuration) [Display omitted] [ABSTRACT FROM AUTHOR]

• Synthesis of unexpected products utilized Biginelli reaction. • FT-IR, NMR and MS spectral data are used to confirm the structure of the synthesized amidopyridines. • Molecular docking study was used to investigate the antimicrobial effectiveness against E. coli, S. pneumoniae, G. candidum , and A. flavus. • DFT analysis of the Biginelli reaction mechanism and optimization of synthesized heterocycles was studied utilizing B3LYP/6–311(G) basis set. The Biginelli reaction of 3-oxo- N -(2-pyridyl)butanamide with thiourea (or urea) and some aromatic aldehydes afforded new chemical skeletons containing tetrahydropyrimidine, pyridine, and carboxamide pharmacophoric moieties. The expected products of this reaction were not isolated in the case of 4-nitrobenzaldehyde, pyridine-2-carbaldehyde, and thiophene-2-carbaldehyde; rather the corresponding acrylamide derivatives were obtained. Chemical structures of the newly synthesized hybrids were elucidated by FT-IR, NMR spectroscopy in addition to mass spectrometry and elemental analyses. The in-vitro antimicrobial activity showed that the products were highly active against the tested pathogens that were confirmed through molecular docking simulation with different proteins such as PDBID: 3t88, 2wje, 1tgh, and 4ynt which showed a different binding affinity with attraction of amino acids of proteins. Furthermore, the optimization of different pyridine carboxamides utilized a DFT/B3LYP-6311(G) basis set to know the cyclization of butanamide 1 with thiourea and different aldehydes in the presence of electron-donating/withdrawing groups which affected of the expected products with different transition states. Moreover, the determination of the energy gap and physical descriptors of these pyridine carboxamide derivatives showed the stability of tetrahydropyrimidines 2a,b due to the presence of donating groups which enhanced the activity and stability. Determination of the ESP and MEP of compounds 2a,b confirmed a correlation with biological evaluations. [Display omitted] [ABSTRACT FROM AUTHOR]

• Straightforward synthetic access to α-functionalized β-enamino γ-sultams. • NMR, IR, and X-ray diffraction study. • DFT calculations. • Formulated rules of structure‒activity relationship. Herein we describe the reaction of 2-methyl-2-(methylamino)propanenitrile and 1-(methylamino)cyclobutane-1-carbonitrile with α-functionalized sulfonyl chlorides and the reactivity of resulting α-functionalized β-enamino γ-sultams. The nature of the substituent or the functional group in the α-position has a decisive impact on the reactivity of β-enamino γ-sultams. In particular, α-unsubstituted β-enamino γ-sultams and those possessing either electron-donating substituents or phenyl group are prepared through the two-step procedure and are prone to acid-mediated hydrolysis. Contrary to that, a strong electron-withdrawing group in the α-position enables the synthesis of the corresponding β-enamino γ-sultams in a one-pot manner and makes them tolerate the acid-mediated hydrolysis. The analysis of the results of a complex study involving physical methods (NMR and IR spectroscopy, X-ray diffraction study) and DFT calculations (performed at PBE0 QZVP level of theory) allowed us to rationalize and formulate the rules of structure‒activity relationship for the discussed sultams. It turned out, that the simplest way to predict the reactivity of α-functionalized β-enamino γ-sultams is the 1H NMR spectroscopy: if the NH 2 group appears in the spectrum as a two-proton singlet the compound is highly likely can be further modified while the appearance of two separated one-proton singlets indicates a low reactivity of β-enamino γ-sultams. [Display omitted] [ABSTRACT FROM AUTHOR]

• The host-guest interactions modes of fully substituted cyclopentanocucurbit[5]uril (CyP 5 Q[5]) with p -aminophenol and p -nitroaniline. • [Z n C l 4 ]2– ion participates in ion-dipole interactions with the outer surface of CyP 5 Q[5] to form supramolecular frameworks. • Two supramolecular frameworks have obvious holes and layered structure. The host-guest interactions modes of fully substituted cyclopentanocucurbit[5]uril (CyP 5 Q[5]) with p -aminophenol (G1) and p -nitroaniline (G2) were investigated by X-ray single crystal diffraction, 1H NMR spectroscopy, mass spectrometry, infrared spectroscopy and thermogravimetric analysis. The results shows that G1 and G2 interact with CyP 5 Q[5] to form host-guest complexes, which can enhance the thermal stability of G1 and G2. The crystal structure shows that G1 and G2 act on the carbonyl-fringed portals of CyP 5 Q[5] via ion-dipole interactions and hydrogen bond interactions, respectively. [ZnCl 4 ]2- ion participates in ion-dipole interactions with the outer surface of CyP 5 Q[5] to form supramolecular frameworks. [ABSTRACT FROM AUTHOR]

• Thioparacetamol was obtained in high yield by microwave thionation of paracetamol. • Conformational equilibrium was revealed through NMR spectroscopy. • A single anti conformer of thioparacetamol was found in the infrared spectra. • Conformational equilibrium ratio varies with solvent polarity. The search for analogs of compounds with proved pharmacological activity frequently starts by obtaining those that result from simple chemical substitutions, have structural and mechanical characteristics suitable for inclusion in a formulation and close similarity with related lead compounds. With this aim, the isosteric replacement of the carbonyl functional group of paracetamol to obtain solid thioparacetamol was achieved through microwave mediated thionation of parent compound in very good yield (85 %). A thorough characterization of the compound prepared was performed by GC/MS spectrometry, FTIR and NMR (1H, 13C, COSY, HSQC and HMBC) spectroscopies and quantum chemical calculations derived from density functional theory. From the experimental and theoretical spectra, it was evidenced that the structural, vibrational and conformational properties of this compound vary whether the sample is solved in a solvent or not. The anti form (anti of the C S and N H bonds) was the preferred conformational isomer in the solid phase, while a conformational equilibrium of anti and syn forms was found for samples solved in different solvents. As polarity of solvents increased, proportion of the anti isomer increased as well. [Display omitted] [ABSTRACT FROM AUTHOR]

• influence of the substitution decoration in ferrocenyl selenophen-2-yl thioketone and ferrocenyl furan-2-yl thioketone utilized as a proligand in complexation reactions with Fe 3 (CO) 12. • Electrochemical investigation of [FeFe]-hydrogenase mimics. • Investigate the catalytic activity of [FeFe]-hydrogenase mimics in the presence of acetic acid. In this report, the influence of the substitution decoration in ferrocenyl selenophen-2-yl thioketone (1) and ferrocenyl furan-2-yl thioketone (2) utilized as a proligand in complexation reactions with Fe 3 (CO) 12 was examined. As a result, three new complexes, considered [FeFe]-hydrogenase mimics, were prepared and characterized by IR, 1H, 13C{1H}, and 77Se{1H} NMR spectroscopy, mass spectrometry, elemental analysis, and X-ray single-crystal diffraction methods. Moreover, the obtained complexes were compared with the analogous ferrocenyl α-thienyl thioketone as a starting material. Respectively, the reaction of compound 1 with Fe 3 (CO) 12 is found to give two complexes that have similar structures to those obtained in analogous reactions with ferrocenyl α-thienyl thioketone. Conversely, compound 2 gives only an α,β-unsaturated aldehyde moiety as a result of the furan ring being opened. Furthermore, the electrochemical properties of the resulting complexes were investigated using cylic voltammerty in the absence and presence of acetic acid (AcOH) as a proton source and compared with their structurally related thiophene derivative. Accordingly, the nature of the linkage of these synthetic approaches has a significant effect in determining its redox properties. [Display omitted] [ABSTRACT FROM AUTHOR]