Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-<i>a</i>]pyridine

Khamees, Hussien Ahmed; Chaluvaiah, Kumara; El-Khatatneh, Nasseem; Swamynayaka, Ananda; Chong, Kwong Huey; Dasappa, Jagadeesh Prasad; Mahendra, M.

doi:10.1107/s2056989019013410

Cited by 19 publications

(5 citation statements)

References 64 publications

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“…The stability of compounds is subjected to the energy of HOMO and LUMO orbitals (i. e., the highest occupied‐ electron donator ‐and lowest unoccupied molecular‐ electron acceptor‐ orbitals) which are known as frontier molecular orbitals (FMOs). The energy gap ▵E gap (i. e., E HOMO ‐E LOMO ) has been considered as powerful parameter for defining the kinetic stability and chemical reactivity descriptors including hardness (η), softness (ζ), electronegativity (χ), electrophilicity (ψ) and Chemical potential (μ) of the compound . Figure represents the surfaces of HOMO and LUMO of different DFT functionals.…”

Section: Resultssupporting

confidence: 89%

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

et al. 2020

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Structure, Hirshfeld surface, spectra and photophysical properties of boronic acid‐based carbohydrate sensor (5‐fluoro‐2‐methoxyphenyl) boronic acid (BA8) has been reported by experimental methods (XRD/FT‐IR/UV/steady state fluorescence) and theoretically by Density functional theory (DFT) model with most accurate functionals (B3LYP/CAM−B3LYP/ M06‐2X). The comparison of theoretical and experimental data exhibited good agreement. Natural bond orbital (NBO) and frontier molecular orbitals (FMOs) have been analysed. The sensing ability of the compound with carbohydrates (D‐glucose and D‐fructose) were studied by UV/fluorescence spectra. The variation of absorbance and fluorescence on pH was rationale with the estimated acid‐base dissociation constants (pKa). Quantum yield (Φ) and fluorescence lifetimes (τ) for the compound and its esters with sugars were calculated. The results of absorbance, fluorescence measurements and calculated photophysical properties indicated fairly selectivity of BA8 with fructose more than the glucose, which is ascertained from both experimental and theoretical results.

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Section: Resultssupporting

confidence: 89%

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

et al. 2020

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“…1). The Br1-C1 bond length [1.887 (2) A ˚] is in good agreement with other structures containing a bromophenyl moiety (Khamees et al, 2019;Arif Tawfeeq et al, 2019). The bond length between C1-C2 [1.363 (4) A ˚], is the shortest among all the bond lengths in the phenyl group, possibly due to the inductive effect of bromine.…”

Section: Structural Commentarysupporting

confidence: 81%

Crystal structure of 4-bromo-N-(propylcarbamoyl)benzenesulfonamide

Bookwala¹,

Patel²,

Flaherty³

et al. 2022

Acta Cryst E

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The title compound, C10H13BrN2O3S, 1, contains a sulfonyl urea moiety, which possesses potential therapeutic functions (e.g., anti-diabetic and herbicidal). The geometry of 1 is similar to its closely related analogues, chlorpropamide and tolbutamide. This compound crystallizes in the monoclinic space group C2/c, having one molecule in its asymmetric unit. The crystal structure of 1, recorded at 296 K, shows intermolecular N—H...O and C—H...O-type infinite hydrogen-bonded chains involving the sulfonyl urea moiety. Hirshfeld surface analysis and the two-dimensional fingerprint plots confirmed hydrogen bonding as the dominant feature in the crystal packing.

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“…To explore the intermolecular interaction energies, an analysis of the energy frameworks obtained from the single point energy calculations at the B3LYP/6-311G** level was carried out using CrystalExplorer17.5 (Spackman & Jayatilaka, 2009). In these calculations, a cluster of 3.8 A ˚radius was generated around the molecule by seeking suitable crystallographic symmetry operations with respect to the central molecule, and then this cluster was taken for the energy calculations (Chebbi et al, 2018;Khamees et al, 2019). The energy frameworks are envisioned in a 3 Â 3 Â 3 unit cell.…”

Section: Hirshfeld Surface Enrichment Ratio and Energy Frameworkmentioning

confidence: 99%

Salt formation, hydrogen-bonding patterns and supramolecular architectures of acridine with salicylic and hippuric acid molecules

Suresh¹,

Saravanan²,

Ramakrishnan³

et al. 2021

Acta Crystallogr C

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The intermolecular interactions and salt formation of acridine with 4-aminosalicylic acid, 5-chlorosalicylic acid and hippuric acid were investigated. The salts obtained were acridin-1-ium 4-aminosalicylate (4-amino-2-hydroxybenzoate), C13H10N+·C7H6NO3 − (I), acridin-1-ium 5-chlorosalicylate (5-chloro-2-hydroxybenzoate), C13H10N+·C7H4ClO3 − (II), and acridin-1-ium hippurate (2-benzamidoacetate) monohydrate, C13H10N+·C9H8NO3 −·H2O (III). Acridine is involved in strong intermolecular interactions with the hydroxy group of the three acids, enabling it to form supramolecular assemblies. Hirshfeld surfaces, fingerprint plots and enrichment ratios were generated and investigated, and the intermolecular interactions were analyzed, revealing their quantitative contributions in the crystal packing of salts I, II and III. A quantum theory of atoms in molecules (QTAIM) analysis shows the charge–density distribution of the intermolecular interactions. The isosurfaces of the noncovalent interactions were studied, which allows visualization of where the hydrogen-bonding and dispersion interactions contribute within the crystal.

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Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine

Abstract: The molecular system displays a planar conformation between the phenyl and imidazo[1,2-a] pyridine rings. Weak C—H⋯π and π–π interactions as well as short contacts consolidate the three-dimensional network structure.

Cited by 19 publications

References 64 publications

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

Crystal structure of 4-bromo-N-(propylcarbamoyl)benzenesulfonamide

Salt formation, hydrogen-bonding patterns and supramolecular architectures of acridine with salicylic and hippuric acid molecules

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Crystal structure, DFT calculation, Hirshfeld surface analysis and energy framework study of 6-bromo-2-(4-bromophenyl)imidazo[1,2-a]pyridine

Abstract: The mol­ecular system displays a planar conformation between the phenyl and imidazo[1,2-a] pyridine rings. Weak C—H⋯π and π–π inter­actions as well as short contacts consolidate the three-dimensional network structure.

Cited by 19 publications

References 64 publications

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

Structural, Quantum Chemical and Spectroscopic Investigations on Photophysical Properties of Fluorescent Saccharide Sensor: Theoretical and Experimental Studies

Crystal structure of 4-bromo-N-(propylcarbamoyl)benzenesulfonamide

Salt formation, hydrogen-bonding patterns and supramolecular architectures of acridine with salicylic and hippuric acid molecules

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Abstract: The molecular system displays a planar conformation between the phenyl and imidazo[1,2-a] pyridine rings. Weak C—H⋯π and π–π interactions as well as short contacts consolidate the three-dimensional network structure.