A Comprehensive Study of N-Butyl-1H-Benzimidazole

Imidazole derivatives have found wide application in organic and medicinal chemistry. In particular, benzimidazoles have proven biological activity as antiviral, antimicrobial, and antitumor agents. In this work, we experimentally and theoretically investigated N-Butyl-1H-benzimidazole. It has been shown that the presence of a butyl substituent in the N position does not significantly affect the conjugation and structural organization of benzimidazole. The optimized molecular parameters were performed by the DFT/B3LYP method with 6-311++G(d,p) basis set. This level of theory shows excellent concurrence with the experimental data. The non-covalent interactions that existed within our compound N-Butyl-1H-benzimidazole were also analyzed by the AIM, RDG, ELF, and LOL topological methods. The color shades of the ELF and LOL maps confirm the presence of bonding and non-bonding electrons in N-Butyl-1H-benzimidazole. From DFT calculations, various methods such as molecular electrostatic potential (MEP), Fukui functions, Mulliken atomic charges, and frontier molecular orbital (HOMO-LUMO) were characterized. Furthermore, UV-Vis absorption and natural bond orbital (NBO) analysis were calculated. It is shown that the experimental and theoretical spectra of N-Butyl-1H-benzimidazole have a peak at 248 nm; in addition, the experimental spectrum has a peak near 295 nm. The NBO method shows that the delocalization of the aσ-electron from σ (C1–C2) is distributed into antibonding σ* (C1–C6), σ* (C1–N26), and σ* (C6–H11), which leads to stabilization energies of 4.63, 0.86, and 2.42 KJ/mol, respectively. Spectroscopic investigations of N-Butyl-1H-benzimidazole were carried out experimentally and theoretically to find FTIR vibrational spectra. © 2022 by the authors

Catalytic sulfation of betulin with sulfamic acid : experiment and DFT calculation

Betulin is an important triterpenoid substance isolated from birch bark, which, together with its sulfates, exhibits important bioactive properties. We report on a newly developed method of betulin sulfation with sulfamic acid in pyridine in the presence of an Amberlyst(®)15 solid acid catalyst. It has been shown that this catalyst remains stable when being repeatedly (up to four cycles) used and ensures obtaining of sulfated betulin with a sulfur content of ~10%. The introduction of the sulfate group into the betulin molecule has been proven by Fourier-transform infrared, ultraviolet-visible, and nuclear magnetic resonance spectroscopy. The Fourier-transform infrared (FTIR) spectra contain absorption bands at 1249 and 835–841 cm(−1); in the UV spectra, the peak intensity decreases; and, in the nuclear magnetic resonance (NMR) spectra, of betulin disulfate, carbons С3 and С28 are completely shifted to the weak-field region (to 88.21 and 67.32 ppm, respectively) with respect to betulin. Using the potentiometric titration method, the product of acidity constants K(1) and K(2) of a solution of the betulin disulfate H(+) form has been found to be 3.86 × 10(–6) ± 0.004. It has been demonstrated by the thermal analysis that betulin and the betulin disulfate sodium salt are stable at temperatures of up to 240 and 220 °C, respectively. The density functional theory method has been used to obtain data on the most stable conformations, molecular electrostatic potential, frontier molecular orbitals, and mulliken atomic charges of betulin and betulin disulfate and to calculate the spectral characteristics of initial and sulfated betulin, which agree well with the experimental data

Self assembly of a novel Cu(II) complex, (C6H9N2)(2)[CuCl4]: experimental, computational, and molecular docking survey

International audienceIn the title salt complex (C6H9N2)(2)[CuCl4] symbolized along this work by (2A5PCuCl(4)), the Cu2+ cation is coordinated by four chloride anions and adopts a distorted tetrahedral geometry. This compound has been crystallized in the monoclinic space group C2/c and the following parameters obtained are a = 13.0244(19) angstrom, b = 8.3149(11) angstrom, c = 16.001(2) angstrom, beta = 93.730(6)degrees, Z = 4, V = 1729.2(4) angstrom(3) at 150 K. In the crystal structure, the atomic arrangement consists of isolated tetrahedral entities connected to the organic groups by weak hydrogen bonds N-H horizontal ellipsis Cl and C-H horizontal ellipsis Cl forming a three-dimensional network. The Hirshfeld surface analysis shows on two-dimensional fingerprints maps the great dominance of H horizontal ellipsis Cl and H horizontal ellipsis H contacts in the crystal packaging. The geometrical optimization, electronic, topological and biological properties of 2A5PCuCl(4) were theoretically studied using DFT. The HOMO and LUMO analysis are used to decide the charge transfer within the structure. Natural bond orbital analysis was carried out to study hyperconjugative interactions. Optical transmission measurements investigated by UV-visible and photoluminescence spectroscopy are carried out on a crystalline thin-film of 2A5PCuCl(4) show the detection of two absorption bands centered at 316 and 519 nm coherent with those observed in the perovskites based on CuCl4. Photoluminescence measurements showed two peaks at around 433 and 472 nm. The unaided-eye-detectable blue luminescence emission comes from the excitonic transition in the CuCl4 anions

Non covalent interactions and molecular docking studies on morphine compound

The (5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol (morphine)molecule has been studied using the density functional theory and molecular docking methods and non covalent interactions. The conformational analysis of the molecule at the B3LYP/6−311++G** and HF/6−311++G** levels has been made. The comparison of the structural parameters computed using the B3LYP function with the experimental data has revealed their good agreement. The weak intermolecular interactions in the morphine structure have been analyzed using several techniques. The Hirshfeld surface study has been carried out to identify the diverse intermolecular interactions (mainly hydrogen bonds) and the … π stacking interactions. The analysis of the topological (AIM, ELF, LOL) and non covalent (RDG, IRI, DORI) interactions has revealed different categories of inter- and intramolecular contacts on the basis of the electron localization density and color scale indicator, respectively. The molecular docking study has been carried out to examine the possibility of biological application of the title conformer using the 1DLO (cancerous), 2BK3 (Parkinson), 3LN1 (inflammatory), 4HOE (microbial), and 5 K95 (schizophrenia) enzymes. The analysis has shown that the morphine structure can be used not only in analgesia, but also in the treatment of diseases. The investigated compound has shown good results with monoamine oxidase B (MOAB) at a score of −105.04 kcal/mol

Synthesis, experimental and computational study of a non-centrosymmetric material 3-methylbenzylammonium trioxonitrate

International audienceThis paper shall address the synthesis and characterization of the novel non-centrosymmetric inorganic-organic hybrid material 3-methylbenzylammonium nitrate with general chemical formula C8H12N(NO3) (3MBAN), this compound has been synthesized via slow evaporation method at room temperature and it is structurally characterized by single-crystal X-ray diffraction, crystallized to the monoclinic system with space group Cc and the following parameters 7.574(3), 29.494(10), 5.1894(15), β = 128.669(11)°, Z = 4, V = 905.1(5) Å3 at 150 K and its crystal structure was determined and refined down to R = 0.057 and wR = 0.140. The monoprotonated 3-methylbenzylammonium cations are linked to the trigonal (NO3−) anions by multiple bifurcated N—H…(O,O) and weak C—H…O hydrogen bonds forming R44(12) and R32(6) motifs. The paper discusses also quantitatively the intermolecular interactions using the Hirshfeld surfaces (HS) associated with 2D fingerprint plots. The optimized molecular structure and the vibrational spectra were calculated by the density functional theory (DFT) method using the B3LYP function. Good consistency is found between the calculated results and the experimental structure; IR spectra confirmed the presence of the principal bands assigned to the internal modes of the organic cation and nitrate anion. Topological approaches such as reduced density gradient (RDG), atoms in molecules (AIM), electron localization function (ELF), endorse the occurrence of intermolecular hydrogen bonds that are responsible for the stabilization of the title compound leading to high nonlinear optical (NLO) activity. The analyses of HOMO and LUMO have been used to explain the charge transfer within the molecule. The thermal analysis of the title compound indicates its melting at 395 K follows a rapid decomposition appearing around 495 K. Finally Optical absorption reveals an important band gap energy indicating stability of the title compound

Study of a new piperidone as an anti-Alzheimer agent : molecular docking, electronic and intermolecular interaction investigations by DFT method

In this work, experimental spectroscopic and theoretical methods as quantum chemical calculation were performed for 3-chloro-r(2),c(6)-bis(4-fluorophenyl)-3-methylpiperidin-4-one (abbreviated as CFMP). The CFMP was synthesized and analysed using FT-IR, 1H NMR, 13C NMR, and UV–Vis spectroscopy. Standard functional B3LYP/6–311++G(d,p) density functional theory (DFT) calculations were utilized for the CFMP compound. Molecular electrostatic potential, non-linear optical, and natural bond orbital studies were performed. The charge transfer inside the molecule was demonstrated using HOMO-LUMO energy calculations and Mulliken atomic charges. The vibrational frequency was computed using the DFT/B3LYP/6–311++G(d,p) method. The non-covalent interactions were investigated using the Hirshfeld surface analysis. Furthermore, molecular docking was studied to discover novel inhibitors and drugs in treating Alzheimer's diseases. Further, docking studies were performed to predict and describe the interactions of four proteins with the ligand. This result demonstrates that the CFMP has an inhibitor effect against Alzheimer's diseases

Insight into non-covalent interactions in a tetrachlorocadmate salt with promising NLO properties: Experimental and computational analysis

International audienceThis paper deals with the crystal structure of the new non-centrosymmetric organic-inorganic hybrid material, (C6H14N)2[CdCl4]. Single crystal X-ray diffraction analysis shows that this compound crystallizes in the orthorhombic system, with the space group Cmc21 and the following parameters a = 27.257 (2) Å, b = 8.3560 (6) Å, c = 7.8872 (5) Å, V = 1796.4 (2) Å3 and Z = 4. The structure provides a new interesting example of infinite inorganic chains of [CdCl5]n following the c→ crystallographic direction. The monoprotonated cyclohexylammonium cations are linked to the anions via electrostatic, multiple bifurcated N—H…Cl hydrogen bonds and van der Waals interactions. To support experimental results, DFT calculations have been accomplished via the B3LYP method with 6–311++G(d,p) and LANL2DZ basis set on molecular geometry, vibrational and electronic properties. The non-covalent interactions were studied through AIM and RDG analysis and quantitatively using the Hirshfeld surfaces (HS) associated with 2D fingerprint plots. The NLO properties have been also investigated by DFT and compared to the urea referenc