Ab initio/DFT electronic structure calculations, spectroscopic studies and normal coordinate analysis of 2-chloro-5-bromopyridine

Hiremath, Chidanandayya S.; Yenagi, Jayashree; Tonannavar, J.; Sundius, Tom

doi:10.1016/j.saa.2010.06.033

Cited by 21 publications

(6 citation statements)

References 22 publications

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“…3b), the C-H out of plane bending vibrational mode was observed at 899 cm -1 . These assignments very well agree with the reported values [11,26].…”

Section: C-h Vibrationssupporting

confidence: 93%

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Vibrational spectroscopic and DFT calculation studies of 2-amino-7-bromo-5-oxo-[1]benzopyrano [2,3-b]pyridine-3 carbonitrile

Premkumar¹,

Jawahar²,

Mathavan³

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…3b), the C-H out of plane bending vibrational mode was observed at 899 cm -1 . These assignments very well agree with the reported values [11,26].…”

Section: C-h Vibrationssupporting

confidence: 93%

“…3b) spectra. This assignment agrees well with the literature value[26]. The calculated C-C≡N stretching vibration of the molecule was obtained in the region of 1210-1125 cm -1 .…”

supporting

confidence: 91%

Vibrational spectroscopic and DFT calculation studies of 2-amino-7-bromo-5-oxo-[1]benzopyrano [2,3-b]pyridine-3 carbonitrile

Premkumar¹,

Jawahar²,

Mathavan³

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…The optimized molecular structures of the 3-Br-2-HyP monomer and dimer with the numbering scheme of the atoms are presented in Figure 2 , whereas the optimized geometrical parameters of the 3-Br-2-HyP monomer and dimer were calculated using the HF and B3LYP method with the 6-311++G(d,p) basis set. The corresponding results of the geometrical parameters are gathered in Table 1 and compared with those of available similar systems [ 13 , 42 ]. Similar to what was as observed in Figure 2 for dimer structure and by analyzing the theoretical data obtained, it was found that a strong intermolecular O–H···N hydrogen bond of 1.7163 Å has appeared between the N5(17) and H10(22) atoms.…”

Section: Resultsmentioning

confidence: 99%

“…The solid phase FTIR and FT-Raman spectra of di- and tri-halopyridines were represented [ 11 , 12 ]. 2-Chloro-5-bromopyridine was investigated by spectroscopic studies, normal coordinate analysis and electronic structure analysis [ 13 ]. The ultraviolet absorption spectrum in the vapor and solution phase has been measured for 2-fluoro-5-bromopyridine [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Molecular Structure, Spectral Analysis, Molecular Docking and Physicochemical Studies of 3-Bromo-2-hydroxypyridine Monomer and Dimer as Bromodomain Inhibitors

et al. 2023

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In this paper, both methods (DFT and HF) were used in a theoretical investigation of 3-bromo-2-Hydroxypyridine (3-Br-2HyP) molecules where the molecular structures of the title compound have been optimized. Molecular electrostatic potential (MEP) was computed using the B3LYP/6-311++G(d,p) level of theory. The time-dependent density functional theory (TD-DFT) approach was used to simulate the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) on the one hand to achieve the frontier orbital gap and on the other hand to calculate the UV–visible spectrum of the compound in gas phase and for different solvents. In addition, electronic localization function and Fukui functions were carried out. Intermolecular interactions were discussed by the topological AIM (atoms in molecules) approach. The thermodynamic functions have been reported with the help of spectroscopic data using statistical methods revealing the correlations between these functions and temperature. To describe the non-covalent interactions, the reduced density gradient (RDG) analysis is performed. To study the biological activity of the compound of the molecule, molecular docking studies were executed on the active sites of BRD2 inhibitors and to explore the hydrogen bond interaction, minimum binding energies with targeted receptors such as PDB ID: 5IBN, 3U5K, 6CD5 were calculated.

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“…Due to their cost-effectiveness in computational analyses, density functional theory (DFT) implementations, which are based on the Kohn–Sham partitioning scheme, have emerged as a pivotal approach for the investigation of electronic structure and properties, especially for medium to large-sized molecules. ,− Indeed, DFT functionals have been widely applied to explore the electronic structures and molecular properties of numerous tetrazole derivatives. − This includes the study of their molecular and electronic characteristics including highest occupied molecular orbital (HOMO)–lowest unoccupied molecular orbital (LUMO) levels, natural bond orbital analysis, dipole moments, and electrostatic potential distributions. Furthermore, spectroscopic properties, such as NMR, mass fragmentation patterns, and electronic and vibrational spectra, have also been studied, alongside investigations into their photochemical behavior, particularly concerning tautomeric processes. − ,− Many of these investigations included comparisons with ab initio methods such as Hartree–Fock and second-order perturbation theory, in addition to experimental results. Electronic structure methodologies were also employed to assess the energy profiles of these highly nitrogen-rich compounds with the aim of unraveling structure–property relationships.…”

Section: Introductionmentioning

confidence: 99%

From Molecules to Devices: Insights into Electronic and Optical Properties of Pyridine-Derived Compounds Using Density Functional Theory Calculations

Mahmood,

Akram,

Chen

et al. 2024

J. Phys. Chem. A

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In this study, we delve into the electronic structure, spectroscopic, and optical properties of five benzo derivatives of pyridine, namely, 5-(4-chlorophenyl)-2fluoropyridine (1), 2-fluoro-5-(4-fluorophenyl)pyridine (2), 4-(2-fluoropyridin-5-yl)phenol (3), 5-(2,3-dichlorophenyl)-2-fluoropyridine (4), and 5-(5-bromo-2-methoxyphenyl)-2-fluoropyridine (5). Utilizing quantum chemical density functional theory calculations at the B3LYP and Perdew−Burke−Ernzerhof levels of theory combined with the 6-311G(d,p) and 6-311++G(d,p) basis sets, we investigated the electronic and optical characteristics of these compounds. Band structure calculations were conducted for their crystalline structures, revealing a direct band gap varying from 3.018 to 3.558 eV, with the valence band maximum and conduction band minimum located at the G point in the Brillouin zone. The optical properties were analyzed, including the dielectric functions, reflectivity, and refractive index. Notably, reflectivity was found to be minimal in the photon energy range of 0.0−3.0 eV, and the static refractive index, n(0), ranged from 1.55 to 1.70. The research also involved assessing the reactivity of the compounds through calculation of the frontier orbital energy gaps (ΔE), indicating a significant charge transfer and high reactivity. Additionally, we performed frequency analysis to unveil the Fouriertransform infrared spectra of compounds 1−5 at room temperature. Molecular electrostatic potential surfaces of the optimized structures were employed to map the electrophilic and nucleophilic regions of the compounds. This investigation provides a comprehensive understanding of the electronic and optical properties of these pyridine derivatives, shedding light on their potential applications in optoelectronics.

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Ab initio/DFT electronic structure calculations, spectroscopic studies and normal coordinate analysis of 2-chloro-5-bromopyridine

Cited by 21 publications

References 22 publications

Vibrational spectroscopic and DFT calculation studies of 2-amino-7-bromo-5-oxo-[1]benzopyrano [2,3-b]pyridine-3 carbonitrile

Vibrational spectroscopic and DFT calculation studies of 2-amino-7-bromo-5-oxo-[1]benzopyrano [2,3-b]pyridine-3 carbonitrile

Molecular Structure, Spectral Analysis, Molecular Docking and Physicochemical Studies of 3-Bromo-2-hydroxypyridine Monomer and Dimer as Bromodomain Inhibitors

From Molecules to Devices: Insights into Electronic and Optical Properties of Pyridine-Derived Compounds Using Density Functional Theory Calculations

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