X-ray, tautomeric preference, vibrational spectra, and density functional studies on benzoxazole and benzoxazoline derivatives

Altun, Ahmet; Dursun, Serkan; Agh-Atabay, Naz M.

doi:10.1016/j.vibspec.2015.09.001

Cited by 8 publications

(4 citation statements)

References 57 publications

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“…two tautomers are lying significantly higher than BI-NMeS with too high transition barriers that connect the tautomers to each other, the comparison of the experimental and calculated room temperature vibrational and NMR spectra suggests that they also exist in the solid and solution phases as minor species. These results are quite analogous to the previous findings on the sulfur derivatives of the benzoxazole and benzothiazole isomers [16,17].…”

Section: Resultssupporting

confidence: 91%

“…Optimized gas-phase structures/energetics and vibrational/ NMR spectral characteristics of the isomers were obtained at the B3LYP/6-311++G** level by using Gaussian03 program package [15]. Since the computational methods overestimate the vibrational frequencies systematically, the frequencies have been scaled with the previously derived factors [16,17]. These factors are 0.955 and 0.988…”

Section: Computational Detailsmentioning

confidence: 99%

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Structural Elucidation of Sulfur Derivatives of Benzimidazoles by Density Functional Calculations, and Vibrational and NMR Spectral Analyses

Altun¹,

Azeez²

2015

Pharm Anal Acta

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The room temperature structural as well as vibrational (IR and Raman) and NMR (1 H and 13 C) spectral studies have been performed on 1-methyl-benzimidazole-2-thione, 2-(methylthio)benzimidazole, and 1-methyl-2mercaptobenzimidazole tautomers at B3LYP/6-311++G** level of theory. 1-methyl-benzimidazole-2-thione is the most stable tautomer with significant energetic separations than the other two tautomers and with too high transition barriers to the other tautomers. This suggests that 1-methyl-benzimidazole-2-thione is the main species at the room temperature. Comparison of experimental and calculated room temperature vibrational and NMR spectra suggests the presence of the 2-(methylthio)benzimidazole and 1-methyl-2-mercaptobenzimidazole tautomers in the solid and solution phases as minor species.

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Section: Resultssupporting

confidence: 91%

Section: Computational Detailsmentioning

confidence: 99%

Structural Elucidation of Sulfur Derivatives of Benzimidazoles by Density Functional Calculations, and Vibrational and NMR Spectral Analyses

Altun¹,

Azeez²

2015

Pharm Anal Acta

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“…2 Transition metal ions have different binding forces with N and O atoms. 3 Commonly, N-donor oxazole groups have demonstrated excellent coordination ability with the first-row transition metal ions. 4 Due to the variety of coordination modes and configurations, N-heterocyclic ligands are typically used as neutral ligands in the synthesis of metal complexes.…”

Section: Introductionmentioning

confidence: 99%

Zinc(II) Complex Containing Oxazole Ring: Synthesis, Crystal Structure, Characterization, DFT Calculations, and Hirshfeld Surface Analysis

Ali

Mohamad

Gerber

et al. 2022

ACSi

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A new complex of Zn(II), with 5-chloro-2-methylbenzoxazole ligand (L), has been synthesized by the reaction of zinc dichloride with the ligand (L= C8H6ClNO) in ethanol solution: dichloridobis(5-chloro-2-methyl-1,3-benzoxazole)-zinc(II), C16H12Cl4N2O2Zn. The synthesized complex has been fully characterized by elemental analysis, molar conductivity, FT‑IR, UV‑Vis, and single-crystal X-ray diffraction (XRD). The XRD analysis reveals that the complex has a 1:2 metal-to-ligand ratio. The zinc(II) complex has a distorted tetrahedral geometry with two coordinated nitrogen atoms from the ligand. Density Functional Theory (DFT) calculations were performed at the B3LYP level of theory using the LANL2DZ basis set for metal complex and the 6–31G(d) basis set for non-metal elements to determine the optimum geometry structure of the complex, and the calculated HOMO and LUMO orbital energies were presented. A natural bond orbital (NBO) analysis was carried out on the molecules to analyze the atomic charge distribution before and after the complexation of the ligand. The Hirshfeld surface mapped over dnorm, shape index, and curvature exhibited strong H... Cl/Cl...H and H...H intermolecular interactions as the principal contributors to crystal packing.

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“…Benzoxazole is a five-membered ring compound containing both nitrogen and oxygen fused to a benzene ring and the benzoxazole ring is one of the most common heterocyclics in medicinal chemistry. [19] Benzoxazoles have found applications as intermediates for organic synthesis. [20] In recent years, there have been some interesting developments in the pharmacology of benzoxazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Fe₃O₄‐magnetic nanoparticles using clover leaf aqueous extract: Green synthesis of 1,3‐benzoxazole derivatives

Shafaei

Babaei

Shahvelayati

et al. 2019

J Chinese Chemical Soc

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In this research, magnetic Fe 3 O 4 -NP nanoparticles were synthesized employing a green biosynthetic procedure by reduction of ferric chloride solution with clover leaf water extract. The nanoparticles prepared via this biosynthesis method can potentially be valuable for different purposes such as organic synthesis. In this research, 1,3-benzoxazole derivatives were generated via a multicomponent reaction of α-bromo ketones, isothiocyanate, and propiolate in the presence of a catalytic amount of bio-Fe 3 O 4 MNPs and sodium hydride in water at 50 C in good yields. The catalyst was reused five times with a minor decrease in its catalytic activity. K E Y W O R D S 1,3-benzoxazole, alkyl (aryl) isothiocyanates, clover leaf, Fe 3 O 4 MNPs, isothiocyanates

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X-ray, tautomeric preference, vibrational spectra, and density functional studies on benzoxazole and benzoxazoline derivatives

Cited by 8 publications

References 57 publications

Structural Elucidation of Sulfur Derivatives of Benzimidazoles by Density Functional Calculations, and Vibrational and NMR Spectral Analyses

Structural Elucidation of Sulfur Derivatives of Benzimidazoles by Density Functional Calculations, and Vibrational and NMR Spectral Analyses

Zinc(II) Complex Containing Oxazole Ring: Synthesis, Crystal Structure, Characterization, DFT Calculations, and Hirshfeld Surface Analysis

Biosynthesis of Fe₃O₄‐magnetic nanoparticles using clover leaf aqueous extract: Green synthesis of 1,3‐benzoxazole derivatives

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X-ray, tautomeric preference, vibrational spectra, and density functional studies on benzoxazole and benzoxazoline derivatives

Cited by 8 publications

References 57 publications

Structural Elucidation of Sulfur Derivatives of Benzimidazoles by Density Functional Calculations, and Vibrational and NMR Spectral Analyses

Structural Elucidation of Sulfur Derivatives of Benzimidazoles by Density Functional Calculations, and Vibrational and NMR Spectral Analyses

Zinc(II) Complex Containing Oxazole Ring: Synthesis, Crystal Structure, Characterization, DFT Calculations, and Hirshfeld Surface Analysis

Biosynthesis of Fe3O4‐magnetic nanoparticles using clover leaf aqueous extract: Green synthesis of 1,3‐benzoxazole derivatives

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Biosynthesis of Fe₃O₄‐magnetic nanoparticles using clover leaf aqueous extract: Green synthesis of 1,3‐benzoxazole derivatives