Vibrational spectroscopic study and NBO analysis on tranexamic acid using DFT method

Muthu, S.; Prabhakaran, Annadurai

doi:10.1016/j.saa.2014.03.050

Cited by 88 publications

(17 citation statements)

References 34 publications

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“…On the MEP plot, the blue part represents the highest positive potential and is a more appropriate place for the attack of a nucleophile, while the red color indicates the highest negative potential and is a suitable site for electrophile attack. MEP can be calculated with the help of eq . where V ( r ) is the electrostatic potential, ρ( r ′) is the electron density, and Z A is the nuclear charge that is placed at R A . , The MEP maps of studied compounds ( 3a and 3b ) are displayed in Figure , which explain that the red color in maps is due to the O and S atoms in 3a and 3b . Thus, it is an electron-rich area and a suitable site for electrophilic attack.…”

Section: Methodsmentioning

confidence: 99%

“…where V(r) is the electrostatic potential, ρ(r′) is the electron density, and Z A is the nuclear charge that is placed at R A . 76,77 The MEP maps of studied compounds (3a and 3b) are displayed in Figure 5, which explain that the red color in maps is due to the O and S atoms in 3a and 3b. Thus, it is an electron-rich area and a suitable site for electrophilic attack.…”

Section: Synthesis Of Coumarin-based Thiosemicarbazonesmentioning

confidence: 96%

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Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

et al. 2020

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By the condensation of thiosemicarbazide with coumarin aldehyde, two novel substituted thiosemicarbazones with chemical formulae C24H25N3O3S (3a) and C26H23N3O3S (3b) have been synthesized. The synthesized compounds were resolved using SC-XRD, and structure elucidation was carried out using 1H NMR, 13C NMR, UV–visible, and FT-IR spectroscopic analyses. Computational calculations at the B3LYP/6-311+G(d,p) level of theory were performed to countercheck the experimental (UV–vis, FT-IR) findings and explore the electronic (FMO, NBO, MEP) properties of 3a–b. The nonlinear optical (NLO) properties of 3a–b were estimated using B3LYP, HF, LC-BLYP, CAM-B3LYP, M062X, and M06 functionals in combination with the 6-311+G(d,p) basis set. The crystallographic data revealed that compounds were crystallized as an orthorhombic crystal lattice with the Pbcn space group and the triclinic crystal lattice with the P̅1 space group. A good concurrence among experimental SC-XRD-generated bond lengths, bond angles, FT-IR, UV–vis, and corresponding DFT results was found, which confirms the purity of both compounds. The NBO analysis confirmed the presence of intramolecular hydrogen bonding and hyperconjugative interactions, which not only were the pivotal cause of stability of the investigated compounds but also led to an overwhelming NLO response. The energy differences calculated for HOMO/LUMO are 3.053 and 3.118 eV in 3a and 3b, respectively. The crystal 3b showed a higher value of first-order polarizability at all levels of theory than 3a. Overall results show that the crystals under investigation are polarized in nature with a good dipole moment. A comparative analysis with urea molecules clearly indicates that the studied compounds are acceptable NLO candidates and they can be used for future technological applications.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of Coumarin-based Thiosemicarbazonesmentioning

confidence: 96%

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

et al. 2020

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“…For an aromatic ring, CC vibrations belong to the region 1300-1000 cm −1 while other CC vibrations are present in a range of 1650–1000 cm −1 [ 31 , 32 , 33 ]. For 2BMN, the theoretical peaks corresponding to CC stretching were at 1610, 1573, 1390, 1354, 1204 and 1041 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

Experimental and theoretical spectroscopic (FT-IR, FT-Raman, UV-VIS) analysis, natural bonding orbitals and molecular docking studies on 2-bromo-6-methoxynaphthalene: A potential anti-cancer drug

Saji¹,

Prasana²,

Muthu³

et al. 2021

Heliyon

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The vibrational, electronic and charge transfer studies on 2-bromo-6-methoxynaphthalene (2BMN) were done using DFT method with B3LYP/6-311þþG(d,p) theory using GAUSSIAN 09W software. Theoretical and experimental investigations on FT-IR and FT Raman were executed on 2BMN. The calculated vibrational wavenumbers were scaled using suitable scaling factors and vibrational assignments were done to all modes of vibrations using Potential Energy Distribution (PED). Frontier Molecular Orbitals were calculated using TD-DFT method and the HOMO-LUMO energy gap was also obtained. Other electronic properties and global parameters for 2BMN were found using the HOMO-LUMO energy values. An energy gap of 4.208 eV shows the stability of the molecule. The reactive sites were predicted using Molecular Electrostatic Potential (MEP), Electron Localization Function (ELF) and Fukui calculations. Hence all electrophilic sites and nucleophilic areas of the molecule were determined. The delocalization of electron density was studied using NBO calculations. The intramolecular transitions and stability of structure were explained using in detail using the former. As the compound satisfies drug-like properties and has a softness value (indicating its less toxic nature), it may be used as a pharmaceutical product. Molecular docking studies were made and the protein-ligand binding properties were discussed. It was found out that title compound exhibits anti-cancer activities. The low binding energy predicts that the compound may be modified as a drug for treating Cancer.

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“…The three dimensional (3D) plot of entire electron density of investigated system is known as a molecular electrostatic potential (MEP) which can be evaluated by equation .

normalV ((), r) = \sum ((), \frac{Z_{normalA}}{R_{normalA}} - r) - \int ((), p ((), r^{'}) / r^{'} - r) d r^{'}

Where; the V(r) is molecular electrostatic potential, Z A stands for the magnitude of charge density over nucleus, A placed at R A , ρ (r’) defines the electronic density function and r’ is the integration variable . The applicability of MEP is to understand the reactivity such as electrophilic and nucleophilic attack as well as to explain the non‐covalent interactions .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

Rafiq

Khalid

Tahir

et al. 2019

Applied Organom Chemis

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Present study advocates the joint experimental and computational studies of two potent benzoimidazole-based hydrazones with chemical formula C 23 H 18 F 2 N 4 O (5a) and C 25 H 22 FN 5 O 3 (5b). Both 5a and 5b were synthesized and resolved into their crystal structures using SC-XRD for the assessment of bond lengths, bond angles, unit cells and space groups. The structures of 5a and 5b were chemically characterized using infrared (FT-IR), UV-Visible, nuclear magnetic resonance ( 1 H-NMR and 13 C-NMR), EIMS and elemental analysis. DFT at M06-2X/6-31G(d,p) level of theory was performed to get optimized structures and countercheck the experimental findings. Overall, DFT findings show excellent concurrence with the experimental data which confirms the purity of both compounds. FMO, NBO analysis, MEP surfaces and nonlinear optical (NLO) properties were explored at same level of theory. UV-Vis analysis at TDDFT/M06-2X/6-31G(d,p) level of theory showed that 5b is red shifted with λ max 331.69 nm as compared to 5a with λ max 240.25 nm. Global reactivity parameters were estimated using energy of FMOs indicated the greater harness value than the softness values of 5a and 5b. NBO analysis confirmed that the presence of non-covalent interactions, hydrogen bonding and hyper conjugative interactions are pivotal cause for the existence of 5a and 5b in the solid-state. NLO results of 5a and 5b were observed better than standard molecule recommended the NLO activity of said molecules for optoelectronic applications. Highlights• Two novel benzoimidazole-based hydrazones were synthesized.• XRD, NMR, FT-IR, UV-Vis, EIMS and elemental analysis were performed for the characterization.

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Vibrational spectroscopic study and NBO analysis on tranexamic acid using DFT method

Cited by 88 publications

References 34 publications

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

Exploration of Chromone-Based Thiosemicarbazone Derivatives: SC-XRD/DFT, Spectral (IR, UV–Vis) Characterization, and Quantum Chemical Analysis

Experimental and theoretical spectroscopic (FT-IR, FT-Raman, UV-VIS) analysis, natural bonding orbitals and molecular docking studies on 2-bromo-6-methoxynaphthalene: A potential anti-cancer drug

Synthesis, XRD, spectral (IR, UV–Vis, NMR) characterization and quantum chemical exploration of benzoimidazole‐based hydrazones: A synergistic experimental‐computational analysis

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