Synthesis, X-ray structure analysis, thermodynamic and electronic properties of 4-acetamido benzaldehyde using vibrational spectroscopy and DFT calculations

Jasmine, N. Jeeva; Arunagiri, C.; Subashini, A.; Nithianantham, Stanley; Muthiah, Packianathan Thomas

doi:10.1016/j.molstruc.2016.10.023

Cited by 14 publications

(8 citation statements)

References 43 publications

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“…The results (Figure 4 and Table S4) show that the heat capacity, enthalpy, and entropy all increase with the increasing temperature. 40,41 The entropy and enthalpy of the complex changes demonstrated that the compound possesses more flexibility in changing its own thermodynamic system with the influence of temperature. 42 These results clearly showed that the temperature strongly affects the chemical reactivity as well as the stability of the PVPP−phenol complex.…”

Section: Theoretical Results 221 Potential Energy Curve (Pes)mentioning

confidence: 99%

Two-Dimensional Infrared Correlation Spectroscopy, Conductor-like Screening Model for Real Solvents, and Density Functional Theory Study on the Adsorption Mechanism of Polyvinylpolypyrrolidone for Effective Phenol Removal in an Aqueous Medium

et al. 2021

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The discharge of industrial effluents, such as phenol, into aquatic and soil environments is a global problem due to its serious negative impacts on human health and aquatic ecosystems. In this study, the ability of polyvinylpolypyrrolidone (PVPP) to remove phenol from an aqueous medium was investigated. The results showed that a significant proportion of phenol (up to 74.91%) was removed using PVPP at pH 6.5. Isotherm adsorption experiments of phenol on PVPP indicated that the best-fit adsorption was obtained using Langmuir models. The response peaks of the hydroxyl groups of phenol (OH) and the carboxyl groups (i.e., CO) of PVPP were altered, indicating the formation of a hydrogen bond between the PVPP and phenol during phenol removal, as characterized using 1D and 2D IR spectroscopy. The resulting complexes were successfully characterized based on their thermodynamic properties, Mulliken charge, and electronic transition using the DFT approach. To clarify the types of interactions taking place in the complex systems, quantum theory of atoms in molecules (QTAIM) analysis, reduced density gradient noncovalent interaction (RDG-NCI) approach, and conductor-like screening model for real solvents (COSMO-RS) approach were also successfully calculated. The results showed that the interactions that occurred in the process of removing phenol by PVPP were through hydrogen bonding (based on RDG-NCI and COSMO-RS), which was identified as an intermediate type (∇2ρ(r) > 0 and H < 0, QTAIM). To gain a deeper understanding of how these interactions occurred, further characterization was performed based on adsorption mechanisms using molecular electrostatic potential, global reactivity, and local reactivity descriptors. The results showed that during hydrogen bond formation, PVPP acts as a nucleophile, whereas phenol acts as an electrophile and the O9 atom (i.e., donor electron) reacts with the H22 atom (i.e., acceptor electron).

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Section: Theoretical Results 221 Potential Energy Curve (Pes)mentioning

confidence: 99%

Two-Dimensional Infrared Correlation Spectroscopy, Conductor-like Screening Model for Real Solvents, and Density Functional Theory Study on the Adsorption Mechanism of Polyvinylpolypyrrolidone for Effective Phenol Removal in an Aqueous Medium

et al. 2021

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“…Generally, the stretching vibrations of the C=N and C−N groups are occurred in the region 1672–1566 cm −1 and 1625 cm −1 respectively [53] . For the azo molecules ( A 1 –A 4 ) the experimental stretching frequency of the C=N is observed at the range 1595, 1596, 1597, and 1598 cm −1 and their respective theoretical bands are appeared at 1531, 1567, 1574, and 1581 cm −1 .…”

Section: Resultsmentioning

confidence: 93%

“…The aromatic CH vibrational peak is generally appeared in the region 3100–3000 cm −1 [53] . The theoretical IR absorption band of aromatic CH of the azo molecules ( A 1 –A 4 ) is appeared at 3144, 3030, 3092, and 3044 cm −1 .…”

Section: Resultsmentioning

confidence: 96%

“…The IR vibrations modes of the À NH group and hydroxyl group generally appeared in the region 3500-3000 cm À 1 [53] and 3700-3550 cm À 1 [54] respectively. In the experimental IR spectra of the A 1 azo molecule, the À NH vibrational frequency is observed at 3270 cm À 1 , its corresponding theoretical value is appeared at the region 3582 cm À 1 .…”

Section: Nh and Oh Vibrationsmentioning

confidence: 99%

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Synthesis, Solvatochromic Studies, DFT Calculations, Characterization, and In Silico Molecular Docking Studies of Azo Dyes of 3‐Methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine

Shakuntala,

Keshavayya,

Pampapathi

2024

ChemistrySelect

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In this work, the four azo dyes (A1–A4) were synthesized using 5‐amino‐3‐methyl‐1‐phenyl pyrazole with four different coupling components by the conventional, simple diazo‐coupling method. These synthesized azo molecules were confirmed by various spectroscopic methods viz, FT‐IR spectra, HR‐MS spectra, 1H NMR spectra, and 13C NMR spectra. The electronic absorption and fluorescence spectra of synthesized azo compounds were recorded at room temperature, with different solvents. The DFT calculations were performed using 6‐311++G (d, p) basis set to evaluate the global reactive parameters of the synthesized azo dyes. The anti‐microbial activities were studied; the compound A1 exhibited a good antibacterial and anti‐fungal activities. The study of in silico molecular docking of the azo compounds revealed that all the compounds found to possess were extraordinary binding affinity as compared to the standards. The anti‐tuberculosis study was carried against mycobacterium tuberculosis and the results have shown that, the compound A2 showed good sensitivity to the studied azo compounds.

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“…The parameters of optimized structures are very much similar to X‐ray structural results. DFT studies have been successful in providing theoretical insights into the chemical reactivity and selectivity in terms of popular qualitative chemical concepts like electronegativity (χ), global Hardness (η), global softness (S), chemical potential (μ), and electrophilicity index (ω) . To understand the properties associated with molecular orbitals, HOMO‐LUMO plots were generated from the optimized molecular structures.…”

Section: Resultsmentioning

confidence: 99%

Cocrystals of Gallic Acid with Urea and Propionamide: Supramolecular Structures, Hirshfeld Surface Analysis, and DFT Studies

Jyothi

Gautam

Swain

et al. 2019

Crystal Research and Technology

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The exploitation of new crystal forms with controlled properties of the active pharmaceutical ingredients (APIs) has a significant role in the pharmaceutical industry. Cocrystallization technique is a powerful strategy to modify the physicochemical properties of APIs. In the present work, two pharmaceutical cocrystals-gallic acid-urea (GA-UR) and gallic acid-propionamide (GA-PR)-have been obtained by mechanochemical grinding method. Novel cocrystals are characterized by powder X-ray diffraction, Fourier-transform infrared spectroscopy, and their structures are confirmed by single crystal X-ray diffraction method. The structural analysis confirms the formation of various supramolecular architectures. Thermal gravimetric analysis is carried out to investigate the presence of water/solvent molecules in the cocrystals. Further, the intermolecular interactions in stabilizing the cocrystals are analyzed using Hirshfeld surfaces. Furthermore, the coordinates of cocrystals are optimized by density functional theory (DFT) calculations using B3LYP hybrid functional with 6-31+G(d,p) level basis set. Frontier molecular orbitals (HOMO-LUMO), energy gap, and related molecular properties are also analyzed.

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Synthesis, X-ray structure analysis, thermodynamic and electronic properties of 4-acetamido benzaldehyde using vibrational spectroscopy and DFT calculations

Cited by 14 publications

References 43 publications

Two-Dimensional Infrared Correlation Spectroscopy, Conductor-like Screening Model for Real Solvents, and Density Functional Theory Study on the Adsorption Mechanism of Polyvinylpolypyrrolidone for Effective Phenol Removal in an Aqueous Medium

Two-Dimensional Infrared Correlation Spectroscopy, Conductor-like Screening Model for Real Solvents, and Density Functional Theory Study on the Adsorption Mechanism of Polyvinylpolypyrrolidone for Effective Phenol Removal in an Aqueous Medium

Synthesis, Solvatochromic Studies, DFT Calculations, Characterization, and In Silico Molecular Docking Studies of Azo Dyes of 3‐Methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine

Cocrystals of Gallic Acid with Urea and Propionamide: Supramolecular Structures, Hirshfeld Surface Analysis, and DFT Studies

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