Vibrational Characterization and Molecular Electronic Investigations of 2-acetyl-5-methylfuran using FT-IR, FT-Raman, UV–VIS, NMR, and DFT Methods

Bassey, Victoria M.; Apebende, Chioma G.; Idante, Precious S.; Louis, Hitler; Emori, Wilfred; Cheng, Chun‐Ru; Agwupuye, John A.; Unimuke, Tomsmith O.; Asogwa, Fredrick C.

doi:10.1007/s10895-022-02903-8

Cited by 28 publications

(13 citation statements)

References 31 publications

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“…The hardness of a species, atom, ion, or molecule is a qualitative indication of how polarizable it is, that is, how much its electron cloud is distorted in an electric field. Chemical hardness is perceived as the capacity to resist electron density transfer with surrounding species. − Thus, CHP and FCHP are termed species with less propensity to exchange electron density with the immediate electronic environment by their high global hardness and low global softness values; this also shows that these species will likely be more reactive toward hard bases and generally more reactive. Thiepane has the highest softness and lowest hardness value and as such is the least reactive of the studied compounds toward soft bases based on Pearson’s hard–soft acid–base theory.…”

Section: Results and Discussionmentioning

confidence: 96%

Meta-Hybrid Density Functional Theory Prediction of the Reactivity, Stability, and IGM of Azepane, Oxepane, Thiepane, and Halogenated Cycloheptane

et al. 2022

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The application of plain cycloalkanes and heterocyclic derivatives in the synthesis of valuable natural products and pharmacologically active intermediates has increased tremendously in recent times with much attention being paid to the lower cycloalkane members. The structural and molecular properties of higher seven-membered and nonaromatic heterocyclic derivatives are less known despite their stable nature and vast application; thus, an insight into their structural and electronic properties is still needed. Appropriate quantum chemical calculations utilizing the ab initio (MP2) method, meta-hybrid (M06-2X) functional, and long-range-separated functionals (ωB97XD) have been utilized in this work to investigate the structural reactivity, stability, and behavior of substituents on cycloheptane (CHP) and its derivatives: azepane, oxepane, thiepane, fluorocycloheptane (FCHP), bromocycloheptane (BrCHP), and chlorocycloheptane (ClCHP). Molecular global reactivity descriptors such as Fukui function, frontier molecular orbitals (FMOs), and molecular electrostatic potential were computed and compared with lower members. The results of two population methods CHELPG and Atomic Dipole Corrected Hirshfeld Charges (ADCH) were equally compared to scrutinize the charge distribution in the molecules. The susceptibility of intramolecular interactions between the substituents and cycloalkane ring is revealed by natural bond orbital analysis and intramolecular weak interactions by the independent gradient model (IGM). Other properties such as atomic density of states, intrinsic bond strength index (IBSI), and dipole moments are considered. It is acclaimed that the strain effect is a major determinant effect in the energy balance of cyclic molecules; thus, the ring strain energies and validation of spectroscopic specificities with reference to the X-ray crystallographic data are also considered.

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Section: Results and Discussionmentioning

confidence: 96%

Meta-Hybrid Density Functional Theory Prediction of the Reactivity, Stability, and IGM of Azepane, Oxepane, Thiepane, and Halogenated Cycloheptane

et al. 2022

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“…The estimated frequency is between 1740 to 1720 cm ‐1 . [ 28 ] The conjugation from the benzene ring attached to the C=O functional group lowers the frequencies by about 30 cm ‐1 . The C=C symmetric and asymmetric stretching vibrations are observed between the C=C of the benzene ring.…”

Section: Resultsmentioning

confidence: 99%

“…By generating an infrared absorption spectrum, Fourier Transform Infrared Spectroscopy (FT-IR) findings shows information about the chemical bonds, functional groups, and vibration modes of atoms and molecules. [27,28] The detail vibrational modes, FT-IR frequencies, and functional group assignment of CPHO and NPHO structure in four solvent phases are shown in table 3.…”

Section: Ft-ir Vibrational Analysismentioning

confidence: 99%

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Hydrazineylidene‐3‐oxopropanal derivatives as antiviral agents for treatment of HBV and HCV: Experimental, DFT, and molecular docking studies

Benjamin,

Louis,

Udoikono

et al. 2023

Vietnam Journal of Chemistry

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In this study, two derivatives of hydrazineylidene‐3‐oxopropanal: chlorophenyl (CPHO) and Nitrophenyl (NPHO) substituted hydrazineylidene compounds were synthesized, spectroscopically characterized using (FT‐IR, UV, and NMR), and theoretically modelled as a potential drug for the treatment of antiviral hepatitis (HBV and HCV) using in‐sillico molecular docking approach. Electronic structure investigation based on density functional theory (DFT) at the B3LYP/6‐311++G(d,p) level of theory was conducted for the investigation of the structural, reactivities, and electronic properties of the studied compounds. The FT‐IR analysis in gas, water, ethanol and DMSO indicates a maximum stretching vibrations frequencies of C‐H in NPHO between 3249.38 to 3254.77 cm‐1 and 3236.04 to 3240.66 cm‐1 for CPHO, N‐H for NPHO is 3309.81 to 3336.37 cm‐1, and CPHO is 3330.11 to 3331.18 cm‐1, C=O in NPHO to be 1685.55 to 1705.60 cm‐1, and 1700.31 to 1679.15 cm‐1 for CPHO. The C‐N stretching vibrations in NPHO were 1519.98 to 1562.06 cm‐1 and 1430.05 to 1460.33 cm‐1 for CPHO. The UV‐Vis analysis indicates that NPHO wavelength absorption spectrum showed high excitation energy bands between 369.74 to 440.60 nm and CPHO at 178.95 to 434.08 nm. The highest stabilization energy of NPHO is LP (1) N12 donor and LP*(1) H10 acceptor with a value of 417.54 kcal/mol compared to πC17 ‐ O18 donor and π*C19 ‐ C28 acceptor with a value of 108.33 kcal/mol for CPHO. The molecular binding affinity of CPHO and NPHO had a high mean binding affinity of ‐5.83 and ‐6.05 kcal/mol, compared to the standard antiviral drugs with ‐5.00 kcal/mol. Therefore, the compounds show excellent reactivity based on the electronic structure, spectroscopic characterization and represent a potential antiviral agent treatment for HBV and HCV.

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“…To obtain deeper understanding of the reactivity and stability of the studied compounds and their levels of interaction, frontier molecular orbital (FMO) analyses were employed using the log file from the geometric optimization of the respective compounds [ 22 ]. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital are the central orbitals that constitute the frontier molecular orbital.…”

Section: Resultsmentioning

confidence: 99%

Ti3C2Tx-Modified PEDOT:PSS Hole-Transport Layer for Inverted Perovskite Solar Cells

et al. 2022

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PEDOT:PSS is a commonly used hole-transport layer (HTL) in inverted perovskite solar cells (PSCs) due to its compatibility with low-temperature solution processing. However, it possesses lower conductivity than other conductive polymers and metal oxides, along with surface defects, limiting its photovoltaic performance. In this study, we introduced two-dimensional Ti3C2Tx (MXene) as an additive in the PEDOT:PSS HTL with varying doping concentrations (i.e., 0, 0.03, 0.05, and 0.1 wt.%) to tune the electrical conductivity of PEDOT:PSS and to modify the properties of the perovskite film atop it. We noted that the grain size of the CH3NH3PbI3 (MAPI3) perovskite layer grown over an optimal concentration of MXene (0.03 wt.%)-doped PEDOT:PSS increased from 250 nm to 400 nm, reducing charge recombination due to fewer grain boundaries. Ultraviolet photoelectron spectroscopy (UPS) revealed increased work function (WF) from 4.43 eV to 4.99 eV with 0.03 wt.% MXene doping, making the extraction of holes easier due to a more favorable energy level alignment with the perovskite. Quantum chemical investigations based on density functional theory (DFT) were conducted at the ωB97XD/6-311++G(d,p) level of theory to provide more insight into the stability, bonding nature, and optoelectronic properties of the PEDOT:PSS–MXene system. The theoretical investigations revealed that the doping of PEDOT:PSS with Ti3C2Tx could cause a significant effect on the electronic properties of the HTL, as experimentally demonstrated by an increase in the electrical conductivity. Finally, the inverted PSCs employing 0.03 wt.% MXene-doped PEDOT:PSS showed an average power conversion efficiency (PCE) of 15.1%, up from 12.5% for a reference PSC employing a pristine PEDOT:PSS HTL. The champion device with a 0.03 wt.% MXene–PEDOT:PSS HTL achieved 15.5% PCE.

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Vibrational Characterization and Molecular Electronic Investigations of 2-acetyl-5-methylfuran using FT-IR, FT-Raman, UV–VIS, NMR, and DFT Methods

Cited by 28 publications

References 31 publications

Meta-Hybrid Density Functional Theory Prediction of the Reactivity, Stability, and IGM of Azepane, Oxepane, Thiepane, and Halogenated Cycloheptane

Meta-Hybrid Density Functional Theory Prediction of the Reactivity, Stability, and IGM of Azepane, Oxepane, Thiepane, and Halogenated Cycloheptane

Hydrazineylidene‐3‐oxopropanal derivatives as antiviral agents for treatment of HBV and HCV: Experimental, DFT, and molecular docking studies

Ti3C2Tx-Modified PEDOT:PSS Hole-Transport Layer for Inverted Perovskite Solar Cells

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