Study on conformational stability, molecular structure, vibrational spectra, NBO, TD-DFT, HOMO and LUMO analysis of 3,5-dinitrosalicylic acid by DFT techniques

Sebastian, S.; Sylvestre, S.; Jayabharathi, Jayaraman; Ayyapan, S.; Oudayakumar, K.; Herman, Ignatius A.

doi:10.1016/j.saa.2014.09.135

Cited by 40 publications

(11 citation statements)

References 40 publications

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“…The outcomes of ultraviolet spectrum are represented in Table 7. 27 The highest occupied molecular orbital is denoted by HOMO and lowest unoccupied molecular orbital is denoted by LUMO, which are considered substantial orbitals of frontier molecular orbitals (FMOs). Usually, the HOMO vitality demonstrates the capacity of donating an electron, though, the LUMO vitality speaks to the capacity of picking up an electron.…”

Section: Uv-visible Analysismentioning

confidence: 99%

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Khalid¹,

Ali²,

Aslam³

et al. 2017

IJPSR

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N-heterocyclic compounds have extensive biological and pharmaceutical applications. 8-Hydroxyquinoline (8-HQ) also plays a significant role in many fields of life. The excellent biological significance of the 8-HQ prompted us to extend the DFT based studies. The frontier molecular orbitals (FMOs), UV-VIS and solvation model based studies remained unknown. Therefore, we intended to study the natural bond orbital, FMOs, UV-VIS, thermodynamic properties and medium influence on solvation energies, dipole moment, FT-IR and FT-Raman using polarizable continuum model (PCM) and density-based solvation model (SMD). The electronic properties of molecule were calculated by M06-2X/6-31G (d,P) and B3LYP/6-31G (d,p) level of theories. The solvent influence on the geometric parameters, FT-IR and FT-Raman were studied by B3LYP /6-31G(d) method. A good correspondence is found between the optimized parameters and the reported X-ray data. Natural bond orbital reveals that the maximum stabilization energy reached up to 39.64kJ/mol which is responsible for extra stability of the molecule. In solvated 8-HQ, a significant medium effects on FT-IR and FT-Raman intensities is observed. The intensities enhanced from gas to solvent phase. The solvation free energies are found to be -28.710 and -39.456 kJ/mol in PCM and SMD models respectively. FMOs suggested that this molecule contain less hardness and larger softness values. These findings reveal that the molecule might be bioactive.

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Section: Uv-visible Analysismentioning

confidence: 99%

Untitled

Khalid¹,

Ali²,

Aslam³

et al. 2017

IJPSR

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“…The HOMO/LUMO energy gap controls many chemical reactivity descriptors, such as hardness, electrophilicity, quantum chemistry terms, chemical potential, electronegativity, and local reactivity. [25][26][27][28] For example, the nucleophilicity of the ligand can be evaluated by its ability to donate electrons, which is associated with the HOMO energy level, while the electron affinity is characterized by the LUMO. Fig.…”

Section: Frontier Molecular Orbital Calculationsmentioning

confidence: 99%

Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N₃S₂ Schiff base ligand and its [CuN₃S₂]²⁺ complexes

et al. 2020

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“…Intra-molecular hyperconjugative interactions can be used as a measure of the interaction intensity between electron-acceptor orbitals. In fact, the larger the value of the hyperconjugative interaction, the more intensive the interaction between the donor and acceptor, and the greater the extent of conjugation of the whole system is [19].…”

Section: Computational Detailsmentioning

confidence: 99%

Topological Analysis and Frequency Dependent Hyperpolarizability Calculations of FDDNP: a DFT Study

Akhtari¹,

Hassanzadeh²,

Fakhraei³

et al. 2016

ChemJMold

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Abstract. The topological and fi rst-hyperpolarizability properties of 2-(1-{6-[(2-fl uoroethyl)(methyl)amino]-2-naphthyl}ethylidene)malononitrile (FDDNP) were studied using DFTB3LYP method. The static and dynamic electronic (hyper)polarizabilities of conformers were calculated and a simple two-state model was employed to explain the fi rst hyperpolarizability differences in two conformers. The second harmonic generation property was evaluated at the typical wavelengths of Cr:forsterite, Nd:YAG(neodymium-doped yttrium aluminium garnet) and Ti:sapphire lasers to predict the compound conformers potency for second harmonic generation imaging in biological studies.Keywords: second-harmonic generation, FDDNP, near-infrared, QTAIM. IntroductionOptical imaging techniques based on nonlinear optical phenomena have been widely incorporated in microscopy using ultra-fast pulsed lasers. There have been described many applications in cellular and tissue imaging due to the ability to spatially resolve subcellular details with high molecular contrast [1].The employed near-infrared (NIR) wavelengths reduce scattering and maximize tissue penetration. These characteristics boost nonlinear microscopy as an elective method for imaging cells with micrometer-resolution deep into the living tissues. Both labeled and label-free second harmonic generation (SHG) imaging techniques have been employed in biological studies. For example, the non-centrosymmetric structure of fi brillar collagen is the major source of the SHG signals in different tissues [2,3], and for cellular and subcellular samples. For this purpose, several SHG labels have been used [4,5].The 2-(1-{6-[(2-fl uoroethyl)(methyl)amino]-2-naphthyl}ethylidene)malononitrile (FDDNP) is a functional fl uorescent biomarker belonging to the family of dicyanovinyl naphthalene labels, which binds to its ligand through hydrophobic interactions [6]. FDDNP also binds to amyloid plaques with high affi nity [7]. Fluorescence imaging microscopy of amyloid aggregates has a key role in diagnosing Alzheimer's disease and other neurodegenerative diseases [8,9].According to the importance of second-harmonic generation, as one of the nonlinear excitation families with deep imaging, 3D capabilities and intrinsic contrast in certain tissues, the study of nonlinear optical properties of biomaterials and their labels plays an essential role in development of medicinal optic devices. So far, only a few electronic structure studies on FDDNP and other dicyanovinyl naphthalene biomarkers, based on ab initio calculations have been performed. Petrič et al.[6] performed a combined experimental and theoretical study on FDDNP and its analogs to explain the chemical modifi cation effects on binding affi nity of biomarkers to amyloid plaques and their fl uorescence Quantum yields. Given the close relationship between the structure and nonlinear activities, and the functional importance of default molecule, it is necessary to develop a deeper vision on electron-topological properties, in order to predict its di...

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Study on conformational stability, molecular structure, vibrational spectra, NBO, TD-DFT, HOMO and LUMO analysis of 3,5-dinitrosalicylic acid by DFT techniques

Cited by 40 publications

References 40 publications

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Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N₃S₂ Schiff base ligand and its [CuN₃S₂]²⁺ complexes

Topological Analysis and Frequency Dependent Hyperpolarizability Calculations of FDDNP: a DFT Study

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Study on conformational stability, molecular structure, vibrational spectra, NBO, TD-DFT, HOMO and LUMO analysis of 3,5-dinitrosalicylic acid by DFT techniques

Cited by 40 publications

References 40 publications

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Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N3S2 Schiff base ligand and its [CuN3S2]2+ complexes

Topological Analysis and Frequency Dependent Hyperpolarizability Calculations of FDDNP: a DFT Study

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Synthesis and physicochemical, DFT, thermal and DNA-binding analysis of a new pentadentate N₃S₂ Schiff base ligand and its [CuN₃S₂]²⁺ complexes