Synthesis of 4-Trialkylsilyl(Germyl)-1H-1,2,3-Triazolecarbaldehyde Oximes*

Медведева, А. С.; Демина, М. М.; Kon'kova, T. V.; Vu, Tran D.; Ларина, Л. И.

doi:10.1007/s10593-014-1551-y

Cited by 10 publications

(7 citation statements)

References 18 publications

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“…Functionalized triazoles are used as high-energy materials, ionic liquids, dyes, universal bases in peptide nucleic acids, synthons for fine organic synthesis, and precursors for nanomaterials [9,11,13]. Such a various use of 1,2,3-triazoles requires an understanding of the features of their electronic and stereochemical structure, spectral properties, and tautomeric transitions [113][114][115][116].…”

Section: Functional 123-triazole Derivativesmentioning

confidence: 99%

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

Ларина

2022

Magnetochemistry

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This review summarizes the data on the stereochemical structure of functionalized azoles (pyrazoles, imidazoles, triazoles, thiazoles, and benzazoles) and related compounds obtained by multipulse and multinuclear 1H, 13C, 15N NMR spectroscopy and quantum chemistry. The stereochemistry of functionalized azoles is a challenging topic of theoretical research, as the correct interpretation of their chemical behavior and biological activity depends on understanding the factors that determine the stereochemical features and relative stability of their tautomers. NMR spectroscopy, in combination with quantum chemical calculations, is the most convenient and reliable approach to the evaluation of the stereochemical behavior of, in particular, nitrogen-containing heteroaromatic and heterocyclic compounds. Over the last decade, 15N NMR spectroscopy has become almost an express method for the determination of the structure of nitrogen-containing heterocycles.

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Section: Functional 123-triazole Derivativesmentioning

confidence: 99%

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

Ларина

2022

Magnetochemistry

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“…Table 2. The 35 Cl NQR frequencies at 77 K (ν, MHz) and signal-to noise ratio (s/n) in the NQR spectra of chloro-containing benzimidazoles and benzothiazole (13)(14)(15)(16)(17)(18) these compounds are transformed into an ionic form. The generation of a cation induces a higher rearrangement of the chlorine electron density than that which is observed upon transition to the anion.…”

Section: Chloro-containing Benzazolesmentioning

confidence: 99%

“…We studied 35 Cl NQR spectra at 77 K of the chloro-containing benzimidazole derivatives (13)(14)(15)(16)(17)(18) (Table 2) [46,83]. Table 2.…”

Section: Chloro-containing Benzazolesmentioning

confidence: 99%

“…Table 2. The 35 Cl NQR frequencies at 77 K (ν, MHz) and signal-to noise ratio (s/n) in the NQR spectra of chloro-containing benzimidazoles and benzothiazole (13)(14)(15)(16)(17)(18) Calculations of the 2-trichloromethylbenzimidazole molecule have been carried out for three possible orientations of the trichloromethyl group relative to the benzimidazole ring plane (Scheme 3, conformation A, B, C) [38,46,83]. If the situation is realized when the dihedral angle ϕ = 0° (conformation A), then in the 35 Cl NQR spectrum should expect one low frequency signal and two high-frequency signals (possibly only one, but double intensity).…”

Section: Chloro-containing Benzazolesmentioning

confidence: 99%

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Nuclear Quadrupole Resonance Spectroscopy: Tautomerism and Structure of Functional Azoles

Ларина

2019

Crystals

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The Nuclear Quadrupole Resonance spectroscopy data of functionalized azoles (imidazoles, triazoles and corresponding benzazoles) are reviewed and critically discussed. The possibility of studying the tautomerism of azoles by the NQR method is considered.Crystals 2019, 9, 366 2 of 12 transfer of a chlorine atom between 1-chlorobenzimidazole and benzimidazole in a CCl 4 /CH 3 OH/K 2 CO 3 medium [52,53]. A similar chlorotropic rearrangement was observed in the equilibrium exchange process between 1-chloroindole and 3-chloro-3H-indole, i.e., the fast intermolecular transformations of 1-chloroindole to 3-chloroindole in the related media were detected [53]. The base-promoted intermolecular mechanism rationalizes chlorotropic processes in N-chlorosubstituted azoles. NQR spectroscopy data are missing.X-ray single-crystal analysis of 1,2,4-triazole (Scheme 1) have revealed a crystalline state of the asymmetric 1H(2H)-tautomer (A, C) [54,55]. Quantum-chemical (ab initio) calculations of 1,2,4-triazole tautomers suggest the prevailing of 1H(2H)-1,2,4-triazole in gas phase as compared to 4H-1,2,4-tautomer by~7 kcal/mol [56][57][58][59], that agrees with experimental data [60,61].

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“…In light of the above, it should be noted that theoretical calculation of NMR chemical shifts is a powerful tool for determining the structure of organic molecules, natural products, and other biochemicals. − Continuing our recent reviews of biologically active azoles, , the present study focuses on a series of functionalized 1,2,3-triazoles, − which are shown in Scheme . A preliminary report regarding a conformational study of the first representative of this series was published in the Structural Chemistry .…”

Section: Introductionmentioning

confidence: 99%

Stereochemical and Computational NMR Survey of 1,2,3-Triazoles: in Search of the Original Tauto-Conformers

Semenov,

Larina

2024

J. Phys. Chem. A

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The conformational analysis of nine functionalized 1,2,3-triazoles was carried out by the correlation of calculated and experimental high-level nuclear magnetic resonance (NMR) chemical shifts. In solution, the studied triazoles are in exchange dynamic equilibrium caused by their prototropic tautomerism of the NH-proton. The experimentally unresolved NMR signals were assigned for most of the compounds. A more thorough survey was conducted for 4-t-butyl-1,2,3-triazole-5-carbaldehyde oxime. The analysis performed within the framework of the DP4+ formalism completely confirmed the hypothesis of the predominance of the 2H-tautomer. Thus, the methodology for estimating stereochemical structures in the absence of some experimental data allowed the most stable conformations for dynamic systems with different tautomeric ratios to be reliably identified.

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Synthesis of 4-Trialkylsilyl(Germyl)-1H-1,2,3-Triazolecarbaldehyde Oximes*

Cited by 10 publications

References 18 publications

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry

Nuclear Quadrupole Resonance Spectroscopy: Tautomerism and Structure of Functional Azoles

Stereochemical and Computational NMR Survey of 1,2,3-Triazoles: in Search of the Original Tauto-Conformers

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