Natural Bond Orbital (NBO) Population Analysis of 1-Azanapthalene-8-ol

Gangadharan, Rubarani P.; Krishnan, S. Sampath

doi:10.12693/aphyspola.125.18

Cited by 139 publications

(39 citation statements)

References 29 publications

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“…Some conflicts are detected with the assignment of the C10 reported by R. P. Gangadharan et al (2014) in which the C10 containing LP(1) with high stabilization energy as 81.91 kJ/mol was reported.7 In the recent study, same reported method as B3LYP/6-31G(d,p) and new M06-2X/6-31G(d,P) method are used to clear this confusion from the literature. Anyway, there is no carbon of the molecule showed any lone pair [LP(1)] see Table 2 and 3.…”

Section: Fig 1: Structural Representation Of 8-hudroxyquinolinementioning

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: Fig 1: Structural Representation Of 8-hudroxyquinolinementioning

confidence: 99%

“…8 Krishnakumar et al (2005) also reported FT-IR and FT-Raman spectra in gas phase. 9 R. P. Gangadharan et al (2014) reported NBO using B3LYP with 6-31G (d, p) basis set, 10 however, some discrepancies have been observed regarding the assignment of NBO analysis.…”

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confidence: 99%

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Khalid¹,

Ali²,

Aslam³

et al. 2017

IJPSR

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“…Bond orbital analysis remains one of the most important parameters in the determination of electron density, charge transfer and atomic charge differences [35]. The orbital analysis was executed using the NBO program [36] implemented in the Gaussian 16 package.…”

Section: Natural Bond Orbitals (Nbos) Analysismentioning

confidence: 99%

Understanding the Hsp90 N-Terminal Dynamics: Structural and Molecular Insights into the Therapeutic Activities of Anticancer Inhibitors Radicicol (RD) and Radicicol Derivative (NVP-YUA922)

et al. 2020

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Heat shock protein 90 (Hsp90) is a crucial component in carcinogenesis and serves as a molecular chaperone that facilitates protein maturation whilst protecting cells against temperature-induced stress. The function of Hsp90 is highly dependent on adenosine triphosphate (ATP) binding to the N-terminal domain of the protein. Thus, inhibition through displacement of ATP by means of competitive binding with a suitable organic molecule is considered an attractive topic in cancer research. Radicicol (RD) and its derivative, resorcinylic isoxazole amine NVP-AUY922 (NVP), have shown promising pharmacodynamics against Hsp90 activity. To date, the underlying binding mechanism of RD and NVP has not yet been investigated. In this study, we provide a comprehensive understanding of the binding mechanism of RD and NVP, from an atomistic perspective. Density functional theory (DFT) calculations enabled the analyses of the compounds’ electronic properties and results obtained proved to be significant in which NVP was predicted to be more favorable with solvation free energy value of −23.3 kcal/mol and highest stability energy of 75.5 kcal/mol for a major atomic delocalization. Molecular dynamic (MD) analysis revealed NVP bound to Hsp90 (NT-NVP) is more stable in comparison to RD (NT-RD). The Hsp90 protein exhibited a greater binding affinity for NT-NVP (−49.4 ± 3.9 kcal/mol) relative to NT-RD (−28.9 ± 4.5 kcal/mol). The key residues influential in this interaction are Gly 97, Asp 93 and Thr 184. These findings provide valuable insights into the Hsp90 dynamics and will serve as a guide for the design of potent novel inhibitors for cancer treatment.

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“…The stabilization energy E 2 associated with i → j delocalization for a donor NBO ( i ) and an acceptor NBO ( j ) is calculated according to

\begin{matrix} T1 \\ E_{2} = q_{i j} \frac{F^{2} (i, j)}{ε_{j} - ε_{i}}, \end{matrix}

where q ij represents the i th donor orbital occupancy and ε i and ε j are diagonal elements and F ( i , j ) off-diagonal elements, respectively, linked to NBO Fock matrix [31]. …”

Section: Computational Details and Theoretical Backgroundmentioning

confidence: 99%

A DFT Study of Structural and Bonding Properties of Complexes Obtained from First-Row Transition Metal Chelation by 3-Alkyl-4-phenylacetylamino-4,5-dihydro-1H-1,2,4-triazol-5-one and Its Derivatives

Nono

Mama

Ghogomu

et al. 2017

Bioinorganic Chemistry and Applications

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Density functional calculations were used to explore the complexation of 3-alkyl-4-phenylacetylamino-4,5-dihydro-1h-1,2,4-triazol-5-one (ADPHT) derivatives by first-row transition metal cations. Neutral ADPHT ligand and mono deprotonated ligands have been used. Geometry optimizations have been performed in gas-phase and solution-phase (water, benzene, and N,N-dimethylformamide (DMF)) with B3LYP/Mixed I (LanL2DZ for metal atom and 6-31+G(d,p) for C, N, O, and H atoms) and with B3LYP/Mixed II (6-31G(d) for metal atom and 6-31+G(d,p) for C, N, O, and H atoms) especially in the gas-phase. Single points have also been carried out at CCSD(T) level. The B3LYP/Mixed I method was used to calculate thermodynamic energies (energies, enthalpies, and Gibb energies) of the formation of the complexes analyzed. The B3LYP/Mixed I complexation energies in the gas phase are therefore compared to those obtained using B3LYP/Mixed II and CCSD(T) calculations. Our results pointed out that the deprotonation of the ligand increases the binding affinity independently of the metal cation used. The topological parameters yielded from Quantum Theory of Atom in Molecules (QTAIM) indicate that metal-ligand bonds are partly covalent. The significant reduction of the proton affinity (PA) observed when passing from ligands to complexes in gas-phase confirms the notable enhancement of antioxidant activities of neutral ligands.

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Natural Bond Orbital (NBO) Population Analysis of 1-Azanapthalene-8-ol

Cited by 139 publications

References 29 publications

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Understanding the Hsp90 N-Terminal Dynamics: Structural and Molecular Insights into the Therapeutic Activities of Anticancer Inhibitors Radicicol (RD) and Radicicol Derivative (NVP-YUA922)

A DFT Study of Structural and Bonding Properties of Complexes Obtained from First-Row Transition Metal Chelation by 3-Alkyl-4-phenylacetylamino-4,5-dihydro-1H-1,2,4-triazol-5-one and Its Derivatives

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