An efficient synthesis, structural (SC-XRD) and spectroscopic (FTIR, 1HNMR, MS spectroscopic) characterization of novel benzofuran-based hydrazones: An experimental and theoretical studies

Khalid, Muhammad; Arshad, Muhammad Nadeem; Tahir, Muhammad Nawaz; Asiri, Abdullah M.; Naseer, Muhammad Moazzam; Ishaq, Muhammad; Khan, Muhammad Usman; Shafiq, Zahid

doi:10.1016/j.molstruc.2020.128318

Cited by 40 publications

(13 citation statements)

References 51 publications

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“…Organic materials are also used in optical fiber telecommunications due to their delocalized electronic systems and the ability to transmit intramolecular charge. 53 Therefore, we calculated the linear polarizability, dipole moment, and second-order hyperpolarizability of our compounds, and the results are tabulated in Table S6 . The investigations presented in Table S6 show that MFIP exhibited the higher value of dipole moment (μ total = 2.35 a.u.)…”

Section: Computational Proceduresmentioning

confidence: 99%

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

et al. 2022

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This investigation is focused on the synthesis of two halo-functionalized crystalline Schiff base (imine) compounds: ( E )-2-methoxy-6-(((3-(trifluoromethyl)phenyl)imino)methyl)phenol ( MFIP ) and ( E )-1-(((2-fluorophenyl)imino)methyl)naphthalen-2-ol ( FPIN ) by the condensation reaction of substituted benzaldehydes and substituted aniline. The crystal structures of MFIP and FPIN were determined unambiguously by single-crystal X-ray diffraction (SC-XRD) studies. Intermolecular interactions and the role of fluorine atoms in the stabilization of the crystal packing are explored for both compounds using Hirshfeld surface analysis. Accompanied with experimental studies, quantum chemical calculations were also performed for comprehensive structure elucidation at the M06/6-311G(d,p) level of theory. A comparison of experimental and density functional theory results for geometrical parameters exhibited excellent agreement. Interestingly, Frontier molecular orbitals and natural bond orbital (NBO) findings revealed that intramolecular charge transfer and hyper-conjugation interactions had played a significant role to stabilize the molecules. Both compounds exhibited a relatively larger value of hardness with a smaller global softness, which, as proposed by the SC-XRD and NBO study, shows a higher stability. Nonlinear optical (NLO) findings showed that FPIN manifested a larger value of linear polarizability (< a > = 293.06 a.u.) and second-order hyperpolarizability (<γ> = 3.31 × 10 5 a.u.) than MFIP (< a > = 252.42 and <γ> = 2.08 × 10 5 a.u.) due to an extended conjugation. The above-mentioned findings of the entitled compounds may play a crucial role in NLO applications.

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Section: Computational Proceduresmentioning

confidence: 99%

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

et al. 2022

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“…46,47 The ionization potential and electron affinity might be utilized to depict the electron gaining and losing capacity of molecules, which interrelated with HOMO/LUMO energies. 48,49 The data tabulated in Table S17 indicate that the values of ionization potential are noticed to be higher than electron affinity, which disclosed that all compounds have better capability to accept an electron. Furthermore, the molecules with the least energy gap were soft exhibiting tunable character, least kinetic stability, and high reactivity and vice versa.…”

Section: Global Reactivity Parametersmentioning

confidence: 99%

An Efficient Synthesis, Spectroscopic Characterization, and Optical Nonlinearity Response of Novel Salicylaldehyde Thiosemicarbazone Derivatives

et al. 2021

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In this study, seven derivatives of salicylaldehyde thiosemicarbazones (1–7) were synthesized by refluxing substituted thiosemicarbazide and salicylaldehyde in an ethanol solvent. Different spectral techniques (UV–vis, IR, and NMR) were used to analyze the prepared compounds (1–7). Accompanied by the experimental study, quantum chemical studies were also carried out at the M06/6-311G(d,p) level. A comparative analysis of the UV–visible spectra and vibrational frequencies between computational and experimental findings was also performed. These comparative data disclosed that both studies were observed to be in excellent agreement. Furthermore, natural bond orbital investigations revealed that nonbonding transitions were significant for the stability of prepared molecules. In addition, frontier molecular orbital (FMO) findings described that a promising charge transfer phenomenon was found in 1–7. The energies of FMOs were further used to determine global reactivity parameters (GRPs). These GRP factors revealed that all synthesized compounds (1–7) contain a greater hardness value (η = 2.1 eV) and a lower softness value (σ = 0.24 eV), which indicated that these compounds were less reactive and more stable. Nonlinear optical (NLO) evaluation displayed that compound 5 consisted of greater values of linear polarizability ⟨α⟩ and third-order polarizability ⟨γ⟩ of 324.93 and 1.69 × 105 a.u., respectively, while compound 3 exhibited a larger value of second-order polarizability (βtotal) of 508.41 a.u. The NLO behavior of these prepared compounds may be significant for the hi-tech NLO applications.

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“…The bandgap of HOMO/LUMO is used to understand the global reactivity parameters (GRP) such as ionization potential (I), [57] electronegativity (X), electron affinity (A), [58] global hardness (η), [59] chemical potential (μ), [28] global electrophilicity (ω), [58] and global softness (σ). [60] By utilizing Equations 2-8, these factors are determined, and results are tabulated in Table 3.…”

Section: Global Reactivity Descriptorsmentioning

confidence: 99%

“…[28] The blue and red color regions in the MEP diagram indicated electron rich and electron poor regions, respectively; however, green color region refers to nearly neutral part. [58] Herein, representative surfaces of entitled complexes are investigated via Argus lab software as shown in Figure S2. These MEP maps reported that oxygen atoms of o-sulfamoylbenzoato ligand that possesses the negative potential as shown by red color indicate a site for electrophilic attack.…”

Section: Molecular Electrostatic Potential (Mep)mentioning

confidence: 99%

Antibacterial metal complexes of o‐sulfamoylbenzoic acid: Synthesis, characterization, and DFT study

Siddiqui

Khalid

Ashraf

et al. 2021

Applied Organom Chemis

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Herein, antibacterial transition metal complexes of ML 2 type having osulfamoylbenzoic acid as ligand were synthesized from saccharin. All characterization techniques confirmed the syntheses of non-ionic transition metal Mn II (3), Co II (4), Ni II (5), Cu II (6), and Zn II (7) complexes, where monoanionic o-sulfamoylbenzoic acid acts as a weak field ligand. The FT-IR, elemental analysis, and magnetic susceptibility studies suggested octahedral and square pyramidal geometries depending on the nature of metal ions. Biological activity of these complexes was studied by using six bacterial strains.Interestingly, the bacterial strains Escherichia coli and Klebsiella aerogenes were inhibited to the maximum level by 6. Among aforementioned five complexes, 4 and 6 were found in crystalline form. Apart from experimental study, DFT study was also performed for entitled complexes at the M06/6-311G(d,p) level. A comparative investigation was performed for geometrical parameters and vibrational analysis, and an agreement was obtained. Natural bonding orbital investigations expressed larger value of stabilization energy 21 kcal/mol for 3, 4, and 6 while 42 kcal/mol for 5 and 7. Furthermore, global reactivity findings also disclosed higher value of hardness (2.44-3.09 eV) for entitled chromophores, hence, showed more stability. Moreover, frontier molecular orbital This research work is attributed to the late Prof. Hamid Latif Siddiqui.

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An efficient synthesis, structural (SC-XRD) and spectroscopic (FTIR, 1HNMR, MS spectroscopic) characterization of novel benzofuran-based hydrazones: An experimental and theoretical studies

Cited by 40 publications

References 51 publications

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

An Efficient Synthesis, Spectroscopic Characterization, and Optical Nonlinearity Response of Novel Salicylaldehyde Thiosemicarbazone Derivatives

Antibacterial metal complexes of o‐sulfamoylbenzoic acid: Synthesis, characterization, and DFT study

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